• 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:
    The invention provides novel N-amino-2-oxo-3-oxazo-lidine derivatives, e.g. 2-methoxy-N-(2,6-dimethylphenyl)-N-(2-oxo-3-oxazolidinyl)-acetamide, which are useful as fungicides. Other objects of the invention are fungicidal compositions comprising such novel compounds and methods of combating phytopathogenic fungi in plants, seeds or soil with the aid of said novel compounds.
    公开号:SU1069624A3
    申请号:SU802962000
    申请日:1980-08-15
    公开日:1984-01-23
    发明作者:Харр Йост；Зандмайер Рудольф；Шеллинг Ханспетер
    申请人:Сандос Аг (Фирма)；
    IPC主号:
    专利说明:

    This invention relates to a process for the preparation of the derivatives of M- (2-oxo-3-oxazolidinyl) cetamides of the total formula and O V / G uCH yN-O O kN 0 WV 5% where R and, („is independently of each other methyl, ethyl orio chlorine or bromine, hydrogen or MwTIl, Chlo or bromine in position 4 or chlorine or bromine in position 3, p4. group SP.OCH., CH, jOC2Hj, CH20-I-CjH. -CHjCi, -oi , base (si2ij, - CHjS-n-, OH-CjHj CH-aij, CHOCHj, CH20CHC2H, j ,,. Bh Y. GM.O. Ijl tlr. R- and R, - independently of each other hydrogen or methyl which possess a fungicidal active bone and can be used in agriculture. oxazolinone derivatives of the general formula o where R is alkyl, which consists in that the compound of the general formula K — CH — CH 2 —TNIH.2 O — CO — 1 H, where R — has the indicated values, is subjected to intramolecular cyclization in a solvent medium at heating 1. Compounds of general formula II possess physiological activity. The aim of the invention is to obtain new oxazolinone derivatives to expand the range of application of oxazolinone class compounds. This objective is achieved by the preparation of compounds of general formula 1, based on cyclization reaction 1, which consists in carrying out the intramolecular condensation of a compound of general formula. isr-c-o-c-c-HaiI where R to Rj have the indicated meanings. Example 1. 2-Methoxy-M- (2,6-dimethylphenyl-N- (2-oxo-3-oxazolidinyl) acetamide. 1G, 8 g (0.0375 mol) of 2-chloroethyl-2- (methoxyacetyl) -2 - (2,6-dimethylphenyl) hydrous zinc carboxylate is added at room temperature under a nitrogen atmosphere in portions to a suspension of 2.0 g of sodium hydride (as a 55% w / w% solution) in a mineral oil in 100 ml of absolute toluene. During the addition process, the temperature as a result of the reaction gradually increases to 40 ° C. After the addition is complete, the reaction mixture is stirred, not cooled, for 30 minutes, and then cooled to 10 ° C. H The reacted sodium hydride is decomposed, ethanol is added to the reaction mixture.The resulting solution is washed with water, dried with magnesium sulfate and the solvent is distilled off in vacuo.The result is a target compound, which after recrystallization from ethanol gives colorless crystals, t: pl. -104 ° C. Example 1a. 2-Chloroethyl 2- (methoxyacetyl) -2- (2,6-dimethylphenyl) hydrazinecarboxylate. The compound used as the starting material of example 1 is prepared as follows. A mixture of 14.7 g (0.06 mol) of 2-chloroethyl-2- (2,6-dimethylphenyl) -hydrazinecarboxylate and 16.2 g (0.1 mol) of methoxy acetoacetic anhydride (CO) Oj is mixed in a medium of dry toluene in for one hour at 80 ° C. After cooling, the solution is washed with water, then with a 5% aqueous solution of NaHCCj and again with water. The solution is dried with and the solvent is distilled off in vacuo. The result is the target compound. Example 1.G, 2-CHLORETHYL-2- (2,6-dimethylphenyl) hydrazinecarboxylate. To a mixture of 127 g (0.935 mol) of 2,6-dimethylphenylhydrazine, -102.5 g (1.3 mol) of pyridium, and 400 ml of water are added at 0-5 ° C 133.5 g (0.935 mol of p, chloroethyl ether After the addition is complete, the mixture is stirred for 2 hours at room temperature, the precipitate is filtered off, washed with water and dried. The resulting compound is recrystallized from toluene. Colorless crystals with mp 74-75c are obtained. a preferred embodiment of the method according to examples 1, la and 1 process d t as follows PRI and ME p 2. 2-MeTOKCH-N (2, -dimethylphenyl) -N- (2-oxo-3-oxazole dinyl) acetamide. 236.1 g (0.75 mol) 2-CHLORETHYL - (methoxyacetyl) -2- (2,6-dimethylphene hydrazinecarboxylate, 275 ml of xylo and 187 ml of water are peanut, cooling the mixture, and 82.5 ml (0.82 mol) of an aqueous solution of sodium hydroxide is added to it , 4 g of NaOH (in ml) at a rate such that the temperature of the mixture was approximately 20 ° C. After the end of the addition, the mixture is stirred for one hour at 20 ° C and then for another 2 hours at 0 ° C. The precipitate is filtered off, washed with 150 ml of water and dried ayut. The result is the target compound in the form of slightly colored crystals with so pl. 102-103 ° C. Example 2a 2-Chloroethyl-2- (methoxyacetyl) -2- (2, b-dimethylphenyl) hydrazinecarboxylate. 200 g (0.825 mol) of 2-chloroethyl-2- (2,6-dimethylphenyl) hydrazinecarboxylate in 500 ml of xylene is heated and added to a hot (at) solution of 2-methoxyacetyl chloride in 250 ml of xylene, obtained in situ by reacting 73 , 5 g (0.826 mol) of thionyl chloride at 80 ° C for 2 hours. The mixture was kept for 30 minutes at, and then the same operations were carried out as in example 1a. Example 26, 2-Chloroethyl-2- (2,6-dimeti phenyl) hydrazinecarboxylate. A mixture of 17.7 g (0.1 mol) of 2,6-dimethylphenyl hydrazine hydrochloride, 21.2 g (0.2 mol) of sodium carbonate in 50 ml of water and 50 ml of xylene is stirred for 30 minutes at room temperature and then cooled. are up to. 14.3 g (0.1 mol) of 2-chloroethyl chloroformate are added to the cooled mixture over 1 hour, maintaining its temperature at 5 ° C. The mixture is stirred at this temperature for another hour and at the end of stirring 100 ml of water is added to it. The resulting precipitates are filtered, washed with water and dried. Further, the same operations are carried out as in example 15. According to a method similar to that described in examples 1 and 2, the compounds of formula 1 obtained in the table are obtained. Test A. Fungicidal activity against Phytophthore infestans. Potted young plants of potatoes (at the stage of their appearance, 3-5 leaves of Ji are sprayed with an aqueous suspension containing 0.003% (w / v) of the compound of the form; ly 1, for example 2-methoxy-M- (2,6- dimethylphenyl) -m- (2-oxo-3-oxazolium ynyl) acetamide. After 2 h, the plants treated in this way are infected with a suspension of Phytophtho and infestans spores, after which they are transferred to a greenhouse and kept at a relative humidity of 100% and duration days -16 hours. The extent of plant damage is assessed after 4-5 days by comparison with the same way infected shadows, which, however, do not undergo pretreatment. The test compound substantially inhibits the development of fungal disease without having a phytotoxic effect on the host plant. Test B. Fungicidal activity against Plasmopara viticola. Young planted in pots grape plants: vino. (at the stage where they appear 3-6 leaves / sprayed with an aqueous suspension containing 0.0008% (w / v) of a compound of formula 1, for example, 2-methoxy-M- ( 2,6-diphenyl) -N- (2-oxo-3-oxazolidinyl) acetamide. After 2 hours, the plants treated in this way are infected with a suspension of spores of Plasmopara viticol, after which they are transferred to a greenhouse and kept at 15-22 s (oscillations with a 24-hour period) and a relative humidity of 100% for a duration of 16 hours. The extent of plant damage is assessed 6 days after infection by comparison with the same but infected, untreated plants. The test compound substantially suppresses the development of a fungal disease without having a phytotoxic effect on the plant farm. Test D. Therapeutic fungicidal action against PlasmoparaV i t i col a. Young young grapes of vinorous grapes planted in pots - (in tadia developed 3-6 Ugistvs) are bred in the same way as in Teyi B. Compound treatment, for example 2-methoxy-M- (2,6-dimethylphenyl) -N- (2 -oxo-3-oxazolidinyl) acetamide, carried out only three days after infection. The incubation conditions are the same as in test B. The extent of the damage is assessed as in test B. The test compound largely suppresses the fungal disease. Test G. Destroying action in relation to Rlasraopara viticola. Evaluation of this type of activity is carried out in the same way as in test B with the difference that the treatment of plants with the test compound is carried out 6 days after infection, when sporulation is observed on the underside of the leaves. The extent of the damage is assessed 7 days after treatment of the plants with a TestNyeMM compound, for example, 2-meTQKCH-N- (2, b-dimethylphenyl) -N- (2-oxo-3-oxazolidinyl) acetamide. As a result, it was established that such treatment leads to a complete cessation of sporulation of the affected zones. Test D. Translocation of vine leaves; The lower side of the cut vine leaves is treated with an aqueous suspension containing 0.012% of a compound of formula 1j, for example, 2-methoxy-M- {2,6-dimethyl-Lphenyl} N- (2-oxo-3-oxazolidinyl) acetamide. After 2 hours, the leaves are completely infected with a suspension of spores of Plasmopara viticola, after which they are kept at a relative humidity of 100% under the same conditions as in test B. Despite the fact that only the underside of the leaves is treated with the test compound, its fungicidal effect appears on both sides of the infected leaves. The same effect is observed when processing
    Physicist e-chemical characteristics of compounds total
    test formula 1}. with a compound, subject only the upper side of the leaves. Thus, 1LOGNZZ conclude that the valid | 2-MeTOKCH-N- (2, 6-dimethylphenyl) (oxo-3-oxazolidinyl) acetamide on the leaf is distributed both acropetally and basipetally. Test E. Tillage. In ViVO experiments using Pythium apharv. These mushrooms are grown in a sterilized mixture of sand and wheat flour (in a volume ratio of 91: 3), to which water is added in the ratio (by volume). 1: 4, for 4 days, at. The resulting culture is mixed with a semi-sterile mixture of peat and sand and the resulting substrate is treated with a suspension of the test compound in such a way that the concentration of the active ingredient is 100-160 ppb. {for example, 10, 40 and 160 r.r.go) of the active component in one volume of the substrate. The substrate treated in this way is filled with pods 5 cm in diameter and ca.)) cucumber seeds are placed in them. The pots are placed in a greenhouse and kept in it for 7 days at 24 ° C and relative air humidity of 6070%. Thereafter, the extent of damage to the plants is evaluated, the number of healthy plants that have emerged is determined, and the results obtained are compared with the results of a control experiment in which the plants were grown in the same infected but untreated soil. The compound obtained in accordance with Example 1 (tested as a wettable powder J completely inhibits the development of a fungal plant disease.
    Table continuation
     Continuation of the table
    权利要求:
    Claims (1)
    [1]
    METHOD FOR PRODUCING N- (2-OXO-3-OXAZOLIDINYL) ACETAMIDES DERIVATIVES .total: formulas where R ^ and R 2 are independently methyl, ethyl or chlorine, or bromine
    R 3 - is hydrogen or methyl, chloro or bromo in the po-; position 4, or chlorine; or bromine at position 3, cd. - Group - '= CH 2 OCH 3, CH 2 = (w 2 n * c ^ o ^ n T | CH ^ 31 ^ c.
    -C V CH ( C1 $ l2 , -th '* /,
    Z. 5 · and - independently from each other hydrogen or methyl;
    Lin M s
    N-c-o-c-c-Hai Yang
    G 4 '<have the indicated meanings.
    SU,. „1069624
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    同族专利:
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3591601A|1967-10-30|1971-07-06|Dow Chemical Co|N-chloro or bromo-2-oxazolidinones|
    US3931213A|1974-12-18|1976-01-06|Interx Research Corporation|3-Chloro-2-oxazolidinones|
    US4097262A|1977-04-22|1978-06-27|E. I. Du Pont De Nemours And Company|Herbicidal acetamides|IT1123564B|1979-09-07|1986-04-30|Montedison Spa|N-ARIL-N-ACIL-3-AMINO-OSSAZOLIDIN-2-ONI FUNGICIDES|
    US4771063A|1985-06-06|1988-09-13|Montedison S.P.A|Fungicidally active N--N-methoxyacetyl-3-amino-1,3-oxazolidin-2-one|
    US5665679A|1995-10-18|1997-09-09|Griffin Corporation|Method of desiccating potato vines with copper alkylenediamine|
    CA2393988A1|1999-12-13|2001-06-21|Bayer Aktiengesellschaft|Fungicidal combinations of active substances|
    DE10019758A1|2000-04-20|2001-10-25|Bayer Ag|Fungicidal combinations containing known methoxyimino-acetic acid amide derivatives useful for the control of phytopathogenic fungi|
    DE10349501A1|2003-10-23|2005-05-25|Bayer Cropscience Ag|Synergistic fungicidal drug combinations|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB7928603|1979-08-16|
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