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  • 专利说明
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    • 专利摘要:
    Tetrahydro-s-triazine thiones, process for their preparation and acaricidal compositions containing them. Compounds of formula: …<CHEM>… wherein R is alkyl, cycloalkyl, adamantyl, lower alkenyl, or a lower-alkynyl or a substituted-lower alkyl wherein the substituent is hydroxy, lower alkoxy, lower alkanoyloxy, carbamoyloxy, N-lower alkyl-carbamoyloxy, N-cycloalkyl-carbamoyloxy, N-aryl-carbamoyloxy, thiocarbamoyloxy, N-lower alkyl-thiocarbamoyloxy, N-cycloalkylthiocarbamoyloxy, N-aryl-thiocarbamoyloxy, aryl-sulphonyloxy, mono- or di-lower alkyl-amino or aryl;… R<1> is lower alkyl or hydroxy-methyl;… and X is hydrogen or lower alkyl;… and acid addition salts thereof. …<??>A process for their preparation and acaricidal compositions.
    公开号:SU753359A3
    申请号:SU782640406
    申请日:1978-07-21
    公开日:1980-07-30
    发明作者:Раймонд Грейвз Лиминг Майкл；Нараянасвами Сабраманиян；Боллиголл Пенроуз Александр
    申请人:Пфайзер Корпорейшн (Фирма)；
    IPC主号:
    专利说明:

    the sulphonir is either reacted with potassium isocyanate or isothiocayate, or when R is hydrogen, it is reacted with formaldehyde.
    The desired products are squeezed in free form or as acid addition salts.
    The process is preferably carried out in an aqueous organic solvent at 45 -.
    The reaction is usually carried out in the presence of an aqueous organic solvent, for example aqueous dioxane, aqueous propanol or aqueous ethyl anglycol, or by adding amine to an excess of formaldehyde aqueous solution and then adding; thiourea, preferably in the form of a solution in an organic solvent such as dsoxane. The reaction can be carried out at a temperature from room temperature to the reflux temperature of the solvent, the reaction can proceed from several hours to several days to complete completion, depending on the nature of the reagents and the temperature used (preferably at 45-50 ° C), for in order to avoid decomposition and formation of by-products, which sometimes occurs at high temperatures. It usually takes two or three days to complete the process at that temperature. In other cases, when P. and R mean lower alkyl (e.g. methyl groups), the reaction can be conducted at a higher temperature, e.g. by heating on a steam bath. In this case, it usually ends within 1.5-3 hours. The product crystallizes when the solution is cooled, and it is also convenient to isolate it by evaporating the solvent or adding a large excess of water to precipitate. The product is collected by filtration or extraction in an organic solvent, for example diethyl ether, and removal of the solvent. In any case, the crude product can be further purified by known techniques, for example, recrystallization or chromatography.
    Compounds of formula I, where ft means C, -C4-alkyl, seen with -C-alkanoyl, can be obtained by acylation of the corresponding hydroxy-lower alkyl-substituted compound, for example, using an acid chloride. Compounds of formula I, where R is -alkyl, substituted carbamoyloxy, or thiocarbamoyloxy, can also be obtained from the corresponding oxyalkyl substituted compound using potassium isocyanate or isothiocyanate or a corresponding lower alkyl, cycloalkyl or aryl isocyanate, or isothiocyanate, respectively. Compound. Formula I, where R is. -eshkyl substituted with an arylsulfonyloxy group, may be obtained from the corresponding hydroxy, C, -C-alkyl compound by sulfonation, for example, using sulfonyl chloride.
    Compounds of formula I where R is a hydroxymethyl group may be prepared.
    Q FROM a compound of formula I, wherein R is hydrogen, prepared as above, using a thiourea of formula I, where R is hydrogen. Thus, by reaction with formaldehyde, a compound of formula I is obtained
    5 where R is hydroxymethyl.
    Salts of compounds of formula I with acids can be obtained in a known manner, for example, by mixing a solution of the free base in a suitable
    0 solvent, diethyl ether, with a solution of the corresponding salt - hydrochloric acid, in a suitable solution (ie, for example, diethyl ether, and isolation of the salt as a precipitate.
    5 The starting compounds of the thiourea of formula I are known, or they can be easily obtained by known reactions by reacting the derivative of aniline substituted in the ring with an alkyl isothiocyanate. The original thiourea is not necessary. It can be isolated, and the reaction mixture can be processed directly with formaldehyde and amine.
     formula RNHr to obtain the final product of formula I in one stage.
    The amines of the formula RNHj are readily available compounds.
    The compounds of the formula I possess aka rycidic activity, especially against all stages in the life cycle, including pregnant female ticks, mites that live on the horned cattle BoophlEus micropBus, HacmophysaEis Bongi-cornus, RhipicephaEus 5 appendicu6atus u BoophiEos decoeotoecto
    For trials, five pregnant Boophitus micropEus adult females
    n ticks are used for each acaricidal compound. Using a micropipette, 10 µl of a solution containing 10 µg of the acaricidal compound in ethanol or acetone is applied to the dorsal surface of each mite. The processing pliers are placed in a glass dish, weighed and stored at 26 ° C and 80% humidity in plastic boxes for two weeks. The tongs are then removed from the dishes and the dishes are weighed to obtain the weight.
    tick-laying eggs. Any decrease in the number of deposited eggs of treated ticks is calculated as a percentage of eggs laid with untreated ticks for control.
    Eggs are returned to the incubator for storage for an additional 3 weeks, after which the percentage of exported eggs is calculated. The percentage of efficacy is calculated as the total decrease in the predicted reproduction of mites using the weight of the deposited and hatching eggs. The experiment can be repeated using a smaller amount of the acaricidal compound.
    In another test, 0.5 ml of a solution containing 0.5 mg of an acaricidal compound in ethanol or acetone was uniformly pipetted onto Whatman filter paper No. 1, measuring 8 x 6.25 cm / 5 O cm, to obtain a dose of 100 mg / m . The treated paper is dried at room temperature, rolled up with the treated surface inward, and the two short edges are joined tightly with a crimping machine. An envelope with open edges is placed in a jug pitcher containing wet cotton in a plastic jug, and stored in an incubator at 26 ° C for 24 hours. 20-50 Boophitus micrptfus larvae that were removed 8–14 days ago are placed in an envelope using a small spatula. The open edges of the envelope are sealed to form a bag. The treated paper containing the larvae is returned to the Pickle vessel and kept for another 48 hours in an incubator, 20-50 larvae are taken as a control and placed in an untreated paper envelope in the same way. At the end of the experiment, the period of which is equal to 48 h, mortality was recorded as a percentage (after adjusting for any mortality) among untreated control ticks.
    The experiment can be repeated using a smaller amount of the acaricidal compound.
    In addition to the data on the percentage efficiency, you can get ED5O results when measuring doses, using any of the described experiments.
    Activity against the HacmaphysaEiS Eongicornus nymphs can be measured in the same way as described for larvae.
    The activity of certain compounds of the examples of the present invention against the tick Boophi &amp; micropEus is given in Table 1.
    T a b l and c a
    Acaricidal activity against
    adults (local use) BoophiEus micropBus
    ten
    15
    20
    25
    thirty
    35
    40
    45
    50
    55
    Thus, the proposed acaricidal composition contains an effective amount of a compound of formula I together with a diluent or carrier. Thinner or carrier
    60 may be solid or liquid, if desired, together with an antioxidant, dispersing agent, emulsifier or wetting agent. The compositions of the invention may
    65
    OfciTb, not only in a suitable form for application, but also in the form of concentrated primary formulations, which must be diluted with an appropriate amount of water or other diluent before application. Typical compression. inventions include, nonshrimer powdered powders, particulate powders, solutions, emulsion dispersions and emulsified concentrates.
    Dusty powders can be obtained by mixing a corresponding amount of finely powdered active compound with a solid powdered diluent or carrier, such as talc, clay, feces, pyrophyllite, diatomaceous earth, nut shell flour, silica gel, hydrated alumina or calcium silicate. Alternatively, a diluent or carrier is mixed with a solution of the active compound in a volatile organic solvent, such as toluene. The solvent is then removed by evaporation. Typically, the active compound is present in the powder in an amount of from 0.25 to about 4 weight.
    Dispersible powders to be sprayed are prepared by adding a suitable dispersing accent to the active compound or to a pulverized powder containing the active compound so that a stable aqueous dispersion of the active compound is formed when the powder is mixed with water. Dispersible sweets preferably contain from 25 to 75% by weight of active compound.
    Emulsified concentrates comprise a solution of the active compound mainly in a water-immiscible non-toxic organic solvent containing an emulsifying agent. Suitable solvents include, for example, toluene, xylene, petroleum oil and alkylated naphthalenes. Preferably, the concentrate contains 5-75 g of active compound per 100 MP solution. Concentrates can be diluted with water before use, in order to obtain a typical concentration of the active compound in an aqueous medium. From 0.01 to 0.1% by weight (volume g / 100 ml), or from about 100 to 1000 parts per ppm. Volatile solvents, such as toluene and xylene, are evaporated after spraying to obtain the remainder of the active ingredient. The resulting sprinkler or maker will usually be in the form of an emulsion.
    The compositions of the invention may be applied to the ground, for example around dairy farms, to protect against cattle ticks. However, it is preferable to treat the animals by spraying the composition on them according to isoretenie or by passing them through a dipping device.
    In this way, it is possible to protect animals, especially cattle, from acarids, in particular from ticks.
    The compositions of the present invention may also contain a pesticide, a fungicide, an additional acaricide, or others.
    Example 1 .Tpem -butylamine (0.88 g, 12 mmol) was added dropwise with stirring to a cooled solution of aqueous form (dehydride) (20 ml). After 15 min, a solution of N-2,4-dimethylphenyl-N-methylthiourea (1.94 g, 10 mmol) in dioxane (5 ml) is added and the mixture is heated at 45-50 ° C for 48 hours. The solvent is removed by evaporation under reduced pressure to obtain an oil, which is washed with water and then extracted with methylene chloride (2 x 50 ml). The extracts are combined, otiate over MgSO4 and evaporated. The residue is isolated in diethyl ether (20 ml) and cooled to obtain a crystalline precipitate which is collected by filtration, washed with a small amount of cold hexane, and dried under vacuum to obtain amp-tre1t-butyl-1- (2, 4-dimethylphenyl) -3- methyltetrahydro-5-triazin-2 (1H) -thion as a white crystalline solid (1.35 g, 46%), so pl. 111-112s.
    Found,%: C 66.4, H 9.0, N 14.6.

    Calculated,%: C 66.0, H8.6,
    N 14.4. M / e found 291, calculated 291.
    Example 2 A solution of 2,4-xylidine (121 g, 90% purity) in ethylene glycol (195 gl) is added over 5 minutes to a mixture of methyl isothiocyanate (73 g) in ethylene glycol (195 ml). Mixture stirred and heated on the steam bath for 1/2 hour. Then an aqueous formaldehyde solution (330 ml, 37%) was added for 5 minutes and then an aqueous solution of methylamine (230 ml 25% w / v), and the reaction mixture again stir and heat on the steam bath for another 1.5 hours. The resulting clear solution is cooled to room temperature with stirring. The resulting crystalline precipitate is collected by filtration, washed and dried. After recrystallization from chloroform-hexane, 1- (2,4-dimethylfanyl) -3,5-dmethyltetrahydro-5-triazin-2 (1H) -thion is obtained (200 g, 87 % yield), so pl. 107-108 0.
    Found,%: O 62.7, H 7.7; N 17.0.
    Citri-.N and
    calculated%: C 62.3; H 7.6; N 16.9. m / e found 249, required 249. Examples 3-2 (4. The following tetrahydro-5-triazine 2C1H) -ions are obtained by the 0.6th method described in Example 1 with the initial thiourea and amine given in Table 2. table 2
    (71.5) (10.2) (10.4) 17 -CH, - (CHj) g CH 4 Adamantyl 418 gSN, -CH. - (CH2) 5CH5 20 -CH; i, - (CH) jOH 21 -CHj -CH, j-Ca.CH 422 -CH, 23 -CHj, - (CH) 40H 24 -CHj, - (CH2) 20CHj Example 25, Formaldehyde (4.86 g, 37% solution, 30 mmol) is added to a solution of 2,4-dimethylphenyl thiourea (4.5 g, 24 mmol) in dimethylformamide (40 ml). Stir for 15 minutes at room temperature. Methylamine (3.72 g, 30 mmol) is added dropwise with stirring and the mixture is heated under reflux at 100 ° C for 4 hours. The solution is cooled and the solvent is removed under vacuum to obtain an oil. It is diluted with diethyl ether and cooled in the refrigerator to give 1- (2,4-dimethylphenyl) -5-methyltetrahydrogen-S-tripiazin-2 (lH) -thione as a white crystalline solid that is collected, washed with a small amount of cold diethyl ether and dried (4.5 g, 77%), so pl. 140143 ° C. The product (1.18 g, 5 mmol) is dissolved in dioxane (5 ml) under heating, the solution is cooled to room temperature, and formaldehyde (0.41 g, 37% solution, 5 ml) is added. The solution is stored at 4. for 6 weeks. Then the solvent was removed under vacuum, and the product was washed with water, dissolved in dichloromethane, dried over MHZOD. The solvent is evaporated. Continuation of table 2 - 70,2519,011,6 (70,4) (9,9) (11,2) 151-2 71,48,611., 3 (71,2) (8,9) (11, 3) oil 67,69,513,2 (67,7) (9,1) (13,2) 110-115 60,67,713,0 (61,4) (7,8) (14,3) 98-99 65,457 , 0115.04 (65.93) (6.96) (15.38) 119-121 67.288.4413.94 (67.25) (8.30) (13.85) oil 60,117.7612.66 (60 , 75) (8,22) (13,29) 91-93 60,917,8213,51 (61,43) (7,85) (14,33) to obtain a clear oil, which is removed by stirring with diethyl ether ( 50 ml). The product is recrystallized from hexane-dichloromethane to give 1- (2,4-dimethylphenyl) -3-oxymethyl-5-methyltetrahydro-5-triazin-2 (1H) -thion as a white crystalline solid (0, 40 g, 30%) m.p. 121122 ° C. Found,%: C 58.5, H 7.1, N 15.65. C, sN19Ms05Calculated,%: C 58.9, H 7.2, N 15.85. Example 26. Acetyl chloride (0.168 g, 1.5 mmol) was added dropwise with stirring to a cooled solution of 1- (2,4-dimethylphenyl) -5- (2-hydroxyethyl) -3-methyltetrahydro-5-triazine-2 (1H) -thione (0.06 g, 1 mmol) in dry toluene (30 ml). After 10 minutes, the solution is warmed to room temperature and stirred for 3 hours. The solution is filtered and the solvent is removed in vacuo. The product is chromatographed on a silica column, diluted with dichloromethane containing 2% methanol to give an oil. Trituration with diethyl ether gives 5- (2-acetoxyethyl) -1 - (2,4-dimethylphenyl) -3-methyltetrahydro-5-triazin-2 (1H) -thione (0.24 g, 35%), m.p. 80-83 C.
    Found: C 59.7 H 7.3, N 12.95.
    Cq Iga 05.5
    Calculated,%: C 59.8 | H 7.2 N 13.1
    Example 27. The method of Example 22 is repeated using pivaloyl chloride to obtain 1- {2,4-dimethylphenyl) -3-methyl-5- (2-pivaloyloxyethyl) -tetrahydro-5-triazin-2 (1H) -thion as oils.
    Found,%: C 62.35, H 8.1, N 10.9.
    CjfoHjgNjO S
    Calculated,%: C 62.8, H 8.0, N 11.6.
    Example 28. Phenyl isocyanate (0.62 g, 5.2 mmol) is added to a stirred solution of 1- (2,4-dimethylphenyl) -5- (2-hydroxyethyl) -3-methyltetrahydro-5-triazin-2 (1H) -thion (1.0 g, 3.5 mmol) and triethylamine (0.31 g, 5.2 mmol) in dry toluene (40 ml). The mixture was stirred at room temperature for 2 hours and the solvent was removed in vacuo. The remaining resin is triturated with petroleum ether (bp 60BO C) to give 1- (2,4-dimethylphenyl) -3-methyl-5- (2-K-phenylcarbamoyloxyethyl) -tetrahydro-5-triazin-2 ( 1H) -thione (1.18 g, 84%), so pl. 60-65 ° C.
    Found,%: C 64.0, H 6.6, N. 13.5.
    .
    Calculated,%: C 63.3, H6.5,
    N 14.1 ..
    Example 29. The procedure of Example 24 was repeated using methyl isocyanate to obtain 1- (2,4-dimethylphenyl) -3-methyl-5- (2-E-methylcarbamoyloxyethyl) -tetrahydro-S-triazin-2 (1H) -thion, t .pl. IO-FROM
    Found,%: C 57.1, H 7.1, N 16.8.
    C, bN24 4025 Calc,%: C57.1, H7.1,
    N 16.6.
    Example 30. A solution of 1- (2,4-dimethylphenyl) -5- (2-hydroxyethyl) -3-methyltetrahydro-5-triazin-2 (1H) -thione (1.0 g, 3.6 mmol) in dimethylformamide ( 10 ml) is added slowly to a stirred suspension of sodium hydride (0.172 g, 3.6 mmol, 50% dispersion in oil) at room temperature. When hydrogen production ceased, a solution of cyclohexyl isothiocyanate (0.74 g, 5.3 mmol) in dimethylformamide (5 mp) was slowly added and the mixture was stirred at room temperature for 3 hours. The solution is then poured into water (50 mp) and the product is extracted into ether. The ether layer is separated, washed with water, dried and the solvent is removed to obtain an oil. After trituration with petroleum ether (bp 60-80 C), 5- (2-N-UHKnoreKsylthiocarbamoyloxyethyl) -1- (2,4-dnmethylphenyl) -2-methyltetrahydro-5-triazin-2 (1H) are obtained. -thion as a white solid (0.18 g, 12%), so pl. 68-72 C.
    Found,%: with 59.8, H 7.7, N 13.1.
    Calculated,%: C 60.1, H 7.4, N 13.4.
    Example 31. The procedure of the example is repeated using methyl isothiocyanate with. Preparation-0 of 1- (2,4-dimethylphenyl) -3-m-ethyl-5- (2-Y-methylthiocarbamoyloxyethyl) -tetrahydro-5-triazin-2 (1H) - Thiona, m.p. 82-90 0.
    Found,%: C 55.1, H7.0, 5 .N.
    Calculated,%: C 54.5, H 6.8, N 15.9.
    Example 32. The method of the example. 26 is repeated using phenyl isothiocyanate to obtain 1- (2,4-dimethylphenyl) -3-methyl-5- (2-M-phenyl thiocarbamoyloxyethyl) -tetrahydro-5-triazin-2 (1H) -thione, mp. 64-70 C.
    5 Found: c 60.9, H 6.3, N 13.7. (G4 2Calculated,%: C 60.9, H 6.3, N 13.5.
    Example 33. Solution p-tolu. Olsulfonyl chloride (3.0 g) in pyridine (5 ml) is slowly added to a cold stirred solution of 1- (2,4-dimethylphenyl) 5- (2-hydroxyethyl) -3-methyltetrahydro-5-triazin-2 (1H) - thios on (1.5 g, 1.8 mmol) in pyridine (10 ml). Stirring is continued for another 10 minutes and the solution is left to stand overnight at. The solution is poured into a mixture of ice and water (400 ml and the product is extracted with ether (2x100 ml). The combined ether extracts are washed with dilute hydrochloric acid and water and dried. The solvent is removed and the residue in the form of a resin is isolated with ethyl acetate. The solvent is cooled and slowly Petroleum ether, bp 40-60 ° C, is added, 1 -. (2, 4-dimethylphenyl) -3-methyl-5- (p-toluenesulfonyloxyethyl) -tetS rahydro-5-triazin-2 (1H) - Thion in the form of a white solid (0.9 g, 58%), mp. 82–85 ° C.
    Found,%: C 58.4, H 6.3, 5 N 9.6.
    C,;, HjT NJ $ 2.
    Calculated,%: C 58.2, H 6.2, N 9.7.
    Example 34. An aqueous formaldeac guide (3.6 g, 4 mmol) is added in
    suspensions of N-2,4-dimethylphenyl-N-methylthiourea (1.76 g, 2 mmol) in ethylene glycol (500 ml), followed by the slow addition of a solution of M, M-di5 K5 ethylethylenediamine (1.76 g, 2.)
    in a small amount of ethylene glycol. The mixture is heated for 1 hour with eo-EO C. It is then cooled and poured into water. The product is extracted in ether, the ether layer is separated, washed with water, dried and evaporated. The crude product is subjected to chromatography with silica diluent with dichloromethane containing 3% methanol to give an oil that solidifies upon trituration with petroleum ether (m.p. 40-60Pc to obtain 1- (2,4-dimethylphenyl) -) 3-methyl-5-dimethyl N-ethyl-tetrahydro-S-tri-aaine-: 2 Cn) -thione (0.6 g, 20%), so pl. 65-70 C.
    Found,%: C 65.25, H 8.6, N 17.8.
    C 62.7, H 8.5,
    Calculated,%: 18.3.
    N
    35. Chloride solution. Example of hydrogen in ether is added to an ethereal solution of 1- (2,4-dimethylphenyl) -3, 5-dimethyltetrahydro-5-triaz-2 (1J) -thion. The mixture is left to stand in the cold for 1 hour and the precipitated hydrochloride salt, the salt in the form of hydrochloride, is collected, washed with water, a small amount of cold ether and dried, m.p. 164165 ° C.
    Found; C 54, 45, H 7, 6, N 15, S 12.6.
     her
    Calculated,%: C 54.6, H 7.0, N 14.7, 5 12.4.
    权利要求:
    Claims (2)
    [1]
    1. Method of producing tetrahydro-S-triazinethions of general formula I
    SNS S .. Hch / - -K /
    where R is alkyl, C —C-cyclo-alkyl, adamantyl, C -, —C-alkenyl or
    Cs-Ce, -alkynyl or substituted C, -C-alkyl, where the substituent is oxy, C -C-alkoxy, C, -C {-alkanoyloxy, carbamoyloxy, M-C, -C; (-alkylcarbamoyloxy, N- cycloapkylcarbamoyloxy, N-phenylcarbamoyloxy, thiocarbamoyloxy, (-alkylthiocarbamoyloxy, N-cycloalkylthiocarbamoyloxy, N-phenylthiocarbamoylyloxy, toluene SULPHONYLOXY, MONO- or CI -yI-CI-CI-CI-CI-CI-CI-CI-CI-I-3, toluene-SULFONYLOXY, MONO- or DI-CI-CI-CI-CI-I,
    R is methyl, ethyl or hydroxymethyl;
    X is an atom of hydrogen or meTHJ or their acid addition salts, which is different in that the thioureas of the formula
    S NH-C-UHR
    where R is hydrogen or
    C, -C4 alkyl and X is as defined above.
    It is reacted with an amine of the formula RNH2, where R is as defined above, in the presence of formaldehyde, and the resulting compound is isolated, or in the case when R is oxy-C-C-apkyl, acylated, sulphonated or reacted with potassium isocyanate or isothiocyanate or when R is hydrogen, it is reacted with formaldehyde, and the target products are isolated in free form or as acid addition salts.
    [2]
    2. The method according to claim 1, characterized in that the reaction is carried out in an aqueous organic solvent at 45-100 ° C.
    Sources of information taken into account in the examination
    1. US patent No. 3505323, cl. 260-248, publ. 1970.
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    同族专利:
    公开号 | 公开日
    EG13455A|1981-12-31|
    IE781452L|1979-01-22|
    JPS5424884A|1979-02-24|
    IE47161B1|1984-01-11|
    PH15775A|1983-03-24|
    FI782192A|1979-01-23|
    AU509780B2|1980-05-22|
    FI66179C|1984-09-10|
    AU3825378A|1980-01-24|
    AR220140A1|1980-10-15|
    ZM6178A1|1980-03-21|
    CA1110622A|1981-10-13|
    DK236878A|1979-01-23|
    US4193994A|1980-03-18|
    ATA522978A|1980-05-15|
    YU160978A|1982-08-31|
    BR7804727A|1979-04-17|
    EP0000640A1|1979-02-07|
    ES471872A1|1979-10-01|
    AT360033B|1980-12-10|
    IL55182A|1983-05-15|
    NZ187927A|1981-03-16|
    IT1097334B|1985-08-31|
    PT68326A|1978-08-01|
    EP0000640B1|1981-06-03|
    IT7826001D0|1978-07-21|
    JPS5826912B2|1983-06-06|
    ES479261A1|1979-12-16|
    CS212231B2|1982-03-26|
    ZA784164B|1979-07-25|
    MX5559E|1983-10-10|
    FI66179B|1984-05-31|
    IL55182D0|1978-09-29|
    IN148647B|1981-04-25|
    DE2860744D1|1981-09-10|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3505057A|1962-03-22|1970-04-07|Du Pont|Method for the control of plants|
    US3505323A|1963-12-06|1970-04-07|Du Pont|Tetrahydro-s-triazin-2--ones and thiones|CA1251294A|1983-04-22|1989-03-14|Mobay Chemical Corporation|Polyether polyurethane prepolymers and castelastomers made therefrom|
    JPH0565579B2|1983-08-25|1993-09-20|Otsuka Kagaku Kk|
    EP0938480A1|1996-11-14|1999-09-01|American Home Products Corporation|Substituted tetrahydro-1,3,5-triazin-2 1h]-thiones as anti-atherosclerotic agents|
    US6160114A|1996-11-14|2000-12-12|American Home Products Corporation|Substituted tetrahydro-1,3,5-triazin-2[1H]-thiones as anti-atherosclerotic agents|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB3099877|1977-07-22|
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