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    • 专利摘要:
    The method of obtaining imidae derivatives of the general formula ORi. To Rg-dH -l / Jrl-KT J CN where R is phenyl, unsubstituted, mono-or disubstituted with halogen, Ci-C4 alkyl or -alkoxy, R-Ci-Cj-alkyl, -alkenyl or a phenylalkyl residue, or their organic or inorganic acid salts, characterized in that the compound of the general formula OKiO RC - 5H1O / C 1H 3 dN O where R and R have the indicated values, is reacted with imidASol in dimethylformamide to freeze the desired product in free form or in the form of organic salt or neor anicheskoy acid.
    公开号:SU1114334A3
    申请号:SU823456111
    申请日:1982-06-25
    公开日:1984-09-15
    发明作者:Баумерт Дитрих；Скеч Карло；Крэмер Хансйерг；Пиро Эрнст
    申请人:Шеринг Аг (Фирма)；
    IPC主号:
    专利说明:

    four
    9
    The invention relates to a process for the preparation of novel imidazolylpropinitrile derivatives with a total NR-C-CiH-lfj 1. CN where R is phenyl, unsubstituted, mono or disubstituted with halogen, alkyl, or C, -C-alkoxy, R — C —Cg-alkyl, C, -Cd-alkenyl or phenylalkyl residue, or their organic or inorganic salts thereof. CnocoiS is known obtaining imidazole derivatives by acidifying imidazole with alkyl ethers of methanesulfonic acid ll. Imidazolyl propionitriles are produced that have fungicidal activity, for example, 3 - (imidazol-1-yl) -2-phenyl-3-butyl-propionitrile nitrate, which has fungicidal action 2. However, these compounds have a relatively low activity and a narrow spectrum of action. The purpose of the invention is a method for the preparation of new imidazolshgar derivatives of pionitriles of the general formula of their salts of organic or inorganic acids with a broad spectrum of fungicidal action. This goal is achieved by the method of obtaining imidazolylpropionitriles of the general formula I or their salts of organic or inorganic acids, in that the compound of the general formula Re-cJNzOfiKJHa I II dN about where Neither RI have the indicated values is reacted with imidaEOL in dimethylformamide with the isolation of the target product in free form or in the form of a salt of an organic or inorganic acid. The resulting salts are partially dissolved in water, well soluble in polar organic solvents such as acetonitrile, N, N-dimethylformamide, lower alcohols, chloroform, and netylene chloride. Example 1. 3- (Imidazol-t-yl) -2-phenyl-2-propioxypropionitrile nitrate (compound 1). 15 g (0.053 mol) of Z-methylsulfonyl oxy-2-phenyl-2-propoxypropionitrile and 17.89 g (0.263 mol) of imidazole with the addition of 1 ml of dimethylformamide are incubated for 16 hours at 140 ° C, excluding the ingress of moisture. After this, the reaction mixture is drunk in ice water, extracted twice with 75 ml of methylene chloride, washed twice with methylene chloride phase with water, dried over magnesium sulfate and after filtering, evaporated in vacuo. The remaining dark oil is dissolved in isopropanol and mixed with 100% nitric acid, taken in an amount somewhat larger than the theoretical one. In order to completely precipitate the precipitate, a small amount of diethyl is added. The precipitated product is sucked off and dried. Yield 12 g (71% of theory). M.p. 168-171 C (decomposition). Example 2. 3- (Imidazol-1-yl) -2-feshch-2-propoxypropionitr1 (compound I). 6.2 g (0.0193 mol) of nitrate are dissolved in methanol and, while cooling on an ice-bath, the reaction mixture is alkalinized with a dilute ammonia solution. After dilution with water, it is extracted with ethyl acetate, the organic phase is washed with water and then loaded onto magnesium sulphate. After filtering, the solution is evaporated in vacuo. An oil is obtained as a residue, which is dried under vacuum. The output of 4.85 g (97% of theory), p 1,5260. Similarly, sledce compounds are obtained. 3. 2-Butoxy-3- (imidazol-1-yl) -2-phenylpropionitrile nitrate, m.p. 1.155 (decomposed). 4.2-Butoxy-3- (imidazess-1-yl) -2-fench1SH) opionitrile, Pd 1.5208. 5. Nitrate 2-all-1-oxy-3- (imidazol-1-yl) -2-phenylpropionitrile, m.p. 1662164 C (decomposed). 6.2-Allylokei-3- (imvdazol-1-sh1) -2-fensh1 propionitrile, h 1,5402. 7. 2-ethoxy-3- (imidazol-1-yl) -2-phenylpropiocitryl nitrate, T.1Sh.18218bc (decomposed). 8.2-Ethoxy-3- (imidazol-1-l) -2-phenylpropionitrile, t, 524 7. 9. 3- (imidazol-1-yl) -2-methoxy-2-phenstropionitrile nitrate, t.p. 189191 s (decomposed)
    10.3- (Imidazol-1-yl) -2-methoxy-2-phenylpropionitrile, m.p. 57-60 C.
    11. 2- (2-chlorophenyl) -3- (imidazol-1-yl) -2-propoxypropionitrile nitrate, m.p. 162-165 ° C (decomposed).
    12. 2-Butoxy-2- (4-chlorophenyl) -3- (imidazol-1-yl) propionitrile nitrate m.p. 178-181 ° C (decomposed).
    13. 2-buloxy-2- (2-chlorophenyl) -3- (imidazol-1-yl) propionitrile nitrate, m.p. 177-178 ° C (decomposed).
    14. 2-allyloxy-2- (2-chlorophenyl) -3- (imidazol-1-yl) -propionitrile nitrate, m.p. 153-155 ° C (decomposed).
    15. Nitrate of 2- (4-hlLrphenyl) -3- (imidazol-1-yl) -2-propoxypropionitrile, m.p. 170-177C (decomposed).
    16. Nitrate 2-all-10 Xi-2- (4-chlorophenyl) -3- (imidazol-1-yl) propionitrile so pl. 152-155 ° C (decomposed).
    17.2- (2-Chlorophenyl) -3- (imidazol-1-Il) -2-PROPOXIPROPIONITRIL, P jj
     1.5343.
    18.2-Butoxy-2- (4-chlorofensh1) -3- (imidazol-1 -yl) propionitrile, p
     1.5288 ..
     19. 2-Butoxy-2- (2-chlorophenyl) -3- (imidazol-1-yl) propionitrile, Pd 1.5329.
    ; 20. 2-Apl1-oxy-2- (2-chlorophenyl) -3- (imidazol-1-yl) propionitra1, nl 1.5490.
    21.2- (4-Chlorophenyl) -3- (imidazol-1; Sh1) -2-propoxypropionitrile, n1 "1.5337.
    22.2-All-1X-2- (4-chlorophenyl) (imidazol-1-yl) propionitrile, 1.5476 g.
    23. 2-benzsh10ksi-3- (imidaZSM1-1-yl) -2-phenylpropionitrile nitrate,
    m.p. 166-168 ° C (decomposed).
    24.2-Benzyloxy-3- (imidazol-1-yl) -2-feshpropyronitrile, p 1,563.
    25. 3- (imidazol-1-yl; -2-isopropyloxy-2-phenylpropionitrile nitrate, m.p., 165-168 ° C. (decomposed)).
    26.3- (Imidazol-1-sh1) -2-isopropyloxy-2-yeni propionic acid 1, 11d 1.5254.
    27. 2- (4-chlorophenyl) -2-hexyloxy-3- (imidazol-1-yl) propionitrile nitrate, m.p. 152-154 ° C (decomposed).
    28.2- (4-Chlorophenyl) -2-hexyloxy-3- (nmid sol-1-yl) propionitrile, p
     1.5197.
    29. yntrate 2-allyloxy-3- (imidazole.-1-yl) -2- (2-methylphenyl) propionitrile, so pl. (decomposed).
    30. 2- (3,4-dichlorophenyl) -3- (imidazol-1-yl) -2-propoxypropionitrile nitrate, m.p. 169-170s (decomposed
    31. Nitrate of 2-aplyloxy-2- (2,4-dichlorophenyl) -3- (imidazol-1-yl) propionitrile, so pl. 158-160 ° C (decomposed).
    32. 2-Butoxy-2- (2,4-dichlorophenyl) -3- (imidazol-1-yl) propionitrile nitrate, m.p. 148-150 C.
    33. 2-ethoxy-2- (3,4-dichlorophenyl) -3- (imidazol-1-yl) propionitrile nitrate m.p. 105-10bs (decomposed).
    34.2-Allyloxy-3- (imidazol-1-IL) -2- (2-methylphenyl) propionitrile, njj
     1.5383.
    35.2- (3,4-Dichlorophenyl) -3- (imidazol-1 -yl) -2-propoxypropionitrile, 1.5360.
    36.2-Allyloxy-2- (3,4-dichlorophenes1-3- (imidazol-1-yl) propionitrile, p
     1,5500.
    37.2-Butoxy-2- (2,4-dichlorophenyl) -3- (imidazol-1-yl) propionitrile, rt
     1.5381.
    38.2-ALLYLOXI-2- (2,4-dichlorophenes 1 -3- (imidazol-1-yl) propionitrile, n1 ° "
     1.5531.
    39.2-Ethoxy-2- (3,4-dichlorophenyl) -3- (imidazol-1-yl) propionitrile.
    40. Nitrate of 3- (imidazol-1-yl) -2-fench1-2- (1,2,2-trimethylpropoxy) -propionitrile, so pl. 168-173 ° C (fold | pagaets).
    41. Nitrate 3- (imidazol-1-yl) -2 (2-metho, xyethoxy) -2-phenylpropionitrile, so pl. 158-160 ° C (decomposed).
    4 2. 2- (2,2-dimethylpropoxy) -3- (imidazol-1-yl) -2-fench1-propionitrile nitrate, m.p. 168-171 ° C (decomposed).
    43.2- (2,2-Dimethylpropoxy) -3- (imidazop-1-yl) -2-phenylpropionitrile, m.p. 89-91 ° C.
    44. 2- (2-FluorophenylU-3- (imidzol-1-yl) -2-propoxypropionitrile nitrate, mp. 170-172 ° C (decomposed).
    45. 2-Butoxy-2- (2-fluorophenl) -3- (imidazol-1-yl) propionitrile nitrate, mp. 173-176 ° C (decomposed).
    46. 2- (4-Fluorophenyl) -3- (imidazol-1-yl) -2-propoxypropionitrile nitrate, m.p. 150-152s.
    47. 2-Butoxy-2- (4-fluorophenyl) -3- (imidazol-1-yl) propionitrile nitrate, m.p. 162-165 ° C (decomposed).
    48. 2-Allyloxy-2- (2-fluorophenyl) -3-midazol-1-yl) propionitrile nitrate, t, Sh1. 169-171 ° C (decomposed). 49, 2-ethoxy-2- (2-fluorophenyl) -3- (imidazol-1-yl) propionitrile nitrate m.p. 172-175 ° C (decomposed). 50, 2- (2-fluorophenyl) -3- (dazol-1-yl) -2-methoxypropionitrile nitrate, Vtnn. 177-170 ° C (decomposed). 51, (Imidazol-1-yl) -2-phenyl-2- (1,2,2-trimethylpropoxy) prO1aonitri so pl, 113-T16 ° C, 52. 3- (Imidazol-1-yl) -2- (2-methox ethoxy) - 2-phenylpropinitrile, P -1.5212. 53.2- (2-Fluorophenyl-3- (imidazol-1-yl) -2-propoxypropionitrile, Pd 1.5143. 54.2-Butoxy-2 (2-fluorophenyl) -3- (imidazol-1-yl) propionitrile, p. 1,5108. 55.2- (4-Fotofenil) -3- (nmidazol-ShI) -2-proproG Hippopiononyl, P 1,5115. 56.2-Nutoxy-2- (4-fluorophenyl) -3- (imidazol-1-yl) propionitrol, D) 1.5085. 57.2- (2-Fluorophenyl) -3-imidazol-1 -yl) -2-methoxypropionitrile, lip 1.5280. 58.2-Ethoxy-2- (2-fluorophenyl) (imidazol-1-yl) propionitrile, n 1.5187. 59.2-Allyloxy-2- (2-fluorofensh1) - (imidazol-1-sh1) propionitrSh1, h 1,5258. 60. 2-Allnloxy-2- (4-fluoro-phenyl) -3- (imidazol-1-yl) -propionitri nitrate mp. 159-161 ° C (decomposed). 61. 2-ethoxy-2- (4-fluorophenyl-3 - (imide a 3 ol-1-yl) propionyl) nitrate, mp 182-184 ° C (decomposed). 62, 2- (4-fluorophenyl nitrate ) -3- (im zasol-1-sh1) -2-methoxy-propionitra1a, mp 194-196 ° C (decomposed). 63.2-Ethoxy-2- (4-fluorophenl) -3- (imidazol-1-sh1 ) propionitrile, mp 54-57 C. 64.2- (4-fluorophenyl) -3- (imidazol-1-yl) -2-methoxy-propionyl, mp. 65.2-Allyloxy-2- (4-fluorophenol) -3- (imidazol-1-yl) propionitrile, 0-1.1,5219. 66, 2-decyloxy-3- (imidaz -1-yl) -2 nitrate, propyl nitrile, mp 126-128 ° C (decomposed 67. Nitrate 2- (3,3-dimethylbutoxy-3- (imidazol-1-yl) -2-phenylpropionyl, so pl. 196-198 ° C (decomposed) 68.3- (Imidazol-1-yl) -2 o Kyloxy-2-phenylpropionitrile, According to 1.5055. 69.2 (3,3-Dimethoxybutoxy) -3- (imidazol-1-yl) -2-phenylpropionitrile, P 1.5093.70. 2- (4-bromophenyl) nitrate -2-butyroxy-3- (imidazol-1-yl) propionitrile, mp 171-174 ° C (decomposes). 71. Nitrate 2- (4-br of fencil) -3- (and shdazol-1-yl ) -2-propoxypropionitrile, mp 162-165 ° C (decomposed) 72. 2- (4-Bromophenyl) -2-hexyloxy-3- (imidazol-1-yl) propionitron nitrate, m.p. 135-138 ° C (decomposed). 73. Nitrate of 3- (yuvadazol-1-yl) -2- (2-methylphenyl) -2-propoxypropionitrile, m.p. 180-183 0 (decomposed). 74. 2-Hexyloxy-3- (imidazol-1-yl) -2- (2-methylphenyl) propionitrile nitrate, m.p. 170-173 ° C. 75.2- (4-Brompheyl) -2-butoxy-3- (imidazrl-1-yl) propionitrile, pJ 1.5405. 76.2- (4-Bromophenyl) -3- (imidazol-1-yl) -2-propoxypropionitrile, n 1.5418. 77.2- (4-Bromophenyl) -2-hexoxy-3- (imidazol-1-yl) propionitrile, h t, 5274. 78.2-Butoxy-3- (imidazol-1-np) -2- (2-methylphenyl) propionitrile, ntj 1,5248. 79. 2-Butoxy-3- (imidazol-1-yl) -2- (2-methyl 1-phenyl) -propionitrile nitrate, m.p. 184-18bs. 80.2-Hexloxy-3- (imidazol-1-yl) -2- (2-methylphenyl) propionitrile, n15 "1.5163. 81.2-Decicycloxy-3- (imidazol-1-yl) -2-phenylpropionitrile, Pr 1.5020. 83.3- (Imidazol-1-ylT-2- (2-metsh1fensh1) -2-propoxypropionitrile, Fri 1.5276, 84.2-Butoxy-2- (3-chlorophenyl) -3- (imidazol-1-1i1) propionitrnl, p - 1.5282. 85. 2- (3-chlorofensh1) -2-hexethoxy-3- (imidazol-1-yl) propionitrile nitrate, m.p., 162-165 ° C (decomposed). 86.3- (ImidazL-1- yl) -2- (2-metsh1fe NILE) -2-octyloxypropionic 1, nig-1,5173. 87.2-Dets1shoksi-3- (imchdazol-1-yl) -2- (2-methylphenyl) propionitrile, p - 1,5139 , 88. 2-Butoxy-3- (imndazol-1-yl) -2- (4-methoxyphenyl) propionitrile nitrate, t, br1 163-167 ° C (decomposed). 89.2-Butoxy-3- (imidazol-1- yl) -2- (4-methoxyphenyl) propionitrile, pp 1.5228. 90. Acid oxalate 2- (4-chlorophenyl) -2-hexyloxy-3- (imidazol-1-yl) pro-5-lyonitrile, mp 195-197 ° C (decomposed) 91. Acidic sulfate 2- (4-chlorophenyl) -2-hexyloxy-3- (imidazol-1-yl) propionitrile , mp 158-163 C (decomposed) "The starting 3-methylene 14 onyl-3-phenyl-2-propoxypropionitrile is obtained as follows. Example 3.3 - Methylsulfonyl-5 -2-phenyl-2-propoxypropionitrile. 27 g ( 0.154 mol) of 2-fensch-2-propoxy-acetonitrile is dissolved in 120 ml of pyridine and mixed with 18.5 g (0.614 mol) of paraformaldehyde. To 20 of this suspension is added, while cooling with ice, 7.7 ml of tetrabutylammonium hydroxide and stirred vigorously for 17 hours. After that, the reaction mixture is poured into ice water and twice extracted with ether. The ether phase is washed twice with an aqueous solution of sodium chloride and dried over magnesium sulfate. After evaporation and evaporation in vacuo 30, a colorless oil remains, which, according to thin layer chromatography, is a pure compound and can be further processed without further purification. The output of 28.4 g of 35, 90% of theory. The compounds of general formula I have a broad spectrum of fungicidal action. Example 4. The effectiveness of the treatment of seeds of seeds against Helminthosporium gram. The seeds of barley with the natural burning of Helminthosporium gram are sown in untreated and treated pots as indicated in Table 1, and they germinate at 16 ° C. After germination, the plants are illuminated every day for 12 hours with artificial light. After approximately 5 weeks, all germinated plants, as well as plants affected by fungi, are counted. In the future, except specifically stated nyl cases, the fungicidal effect is calculated by the formula. 11143 1 Pr 0.001 0.025 About 005 0.001 0.025 0.005 0.001 0.025 0.005 0.001 0.025 0.005 0.001 0.025 0.005 0.0002 12 Continued table. 2 L ± 0,0002 0,0002 0,0002 0,0002 0,0002 0.001 0,0002 0,0002 0,0002 0,0002 0,0002 0.001 0,0002 0,0002 0,0002 0,0002
    7Ц14334
    continuation of the table. 3
    18
    Continued table. four
    P. Example 7. The effectiveness of the prophylactic treatment of the leaves of tomato plants in a greenhouse against Botry tis cinerea. Young tomato plants are sprayed with drops of the active compounds listed in Table. 4 concentrations. After the sprayed layer has dried, the treated plants, as well as untreated control plants, are infected with a spore suspension dispersion (about 1 million in 1 ml of fruit juice solution) of the pathogens with the gray mold of Botrytis cinerea and kept in the wet state approximately at the greenhouse. After a complete failure of the untreated control plants, the scientific research institute (100% of the lesion) determines the extent of the lesion of the treated samples. Table
    12 13
    0.075
    90 95 0.025
    14
    0.025
    60
    eleven
    0.025
    89
    12
    0.026
    93.3 Compare the substance: 1 (4-Chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazole) -1-yl) -I-butanone Example 8. Effectiveness of prophylactic treatment of leaves (Grapevine against Plasmopasa Viticola. Young vines at the stage of development of about 5-8 leaves are sprayed with drops of the compound indicated in Table 5, after the sprayed layer has dried, the reverse side of the leaves is sprayed with an aqueous suspension of fungal spores (about 20,000 per ml) and immediately incubated in a greenhouse at 22-24 ° C in an atmosphere of saturated humidity. From the second day for 3-4 days Air purity is maintained normal (30-70% saturation) and then maintained for an atmosphere of saturated steam.The percentage of the spots affected by the fungus is immediately noted on each sheet and, depending on the treatment, an average is calculated to determine the fungicidal effect. . c g 5 T a b l and
    Continued table. 5 Example 9. In the laboratory, seeds of cress are treated with aqueous emulsion containing 100 ppm of the substance. For this, a seed carrier is placed in a 200 ml glass tube with 10 ml of emulsion. On him impose a paper filter. When the filter paper is impregnated with the solution, 10 cress seeds are evenly spread onto it. Then put a Petri dish on the nozzle. Two nozzles are used for each substance. In order to assess the effectiveness of the compounds in germinated seeds, the length of shoots and roots is determined after 7 days. 6 shows the values in relation to the control plants. The compound test has a strong effect on the growth of shoots and roots. This can be seen in acceleration (100%) or growth inhibition (-1100%) of individual parts. Table 6
    Sales tab. 6
    In tab. 7 shows the results compared to control plants. The data show that the compounds obtained by the proposed method cause a reduction in growth more than the reference compound. : Example 10. Cotton plants are grown under greenhouse conditions up to the stage of budding. The studied compounds spray plants with consumption of 1 and 2 kg of the substance and hectares. Three weeks after the application of the compounds, the total plant size and the first shoot seed are measured.
    23I I
    Example 11, ELF treatment of seeds against mildew cereal Erysiphe graminis.
    The seeds of the game barley are untreated | Ny or pickled with consumable rates 100 g of the effective substance per 100 kg of seeds are sown in pots with the ground and germinated at a temperature of about in the greenhouse. After the formation of the first green leaf, the plants are infected with the help of plants affected by the mildew. After a week, note what percentage of the leaf surface is affected by the mildew.
    Possible incompatibility obra-. , bots are evaluated after growing plants. Evaluation is carried out according to the following scheme: About complete destruction, 1–90% destruction, 2–80% destruction, 3–70% destruction, 4–60% destruction, 5–50% destruction, 6 - 40% destruction, 7 - 30% destruction, 8 - 20% destruction, 9 - 10% destruction, 10 - not damaged. I -
    The compounds of general formula 1 under study are not only effective against Erysiphe graminis, but are also fully compatible with barley plants (see,
    Table 8).
    Table B
    100
    ten
    100
    ten
    24
    Continued table. eight
    Example 12, Effectiveness of prophylactic treatment of sugar beet leaves against pathogens of spots on leaves (Cercospora beticola).
    Plants of sugar beet with 4 well-developed green leaves are sprayed with drops of the studied substances in the table below, 9 concentrations.
    After the sprayed layer has dried, the treated as well as untreated plants are uniformly sprayed with a suspension (15,000 spores per ml). At 26 ° С and in the atmosphere of saturated air
    The plants are kept for 4 days in a greenhouse and after that at approximately 22 ° C, an additional 1-0 days are required. Then the number of affected leaf surfaces is determined. results
    are presented in table. 9
    T a b l and c a 9
    0.05
    100 Continued table. U Compare, 01 my remedy: Ethylene-bis-0.05 -thiocarbamate Manganese
    Example 13. Inhibition of growth of Penicilliim digltatura fungi on nutrient solution.
    20 MP of a nutrient solution from grape juice and water (1: 1) are placed in a glass flask with a volume of 100 MP and mixed with a powdered final preparation of the active compound. Immediately after 111433 5 O
    27
    28
    29 26 this is described in Penicillium spores. digitatum. After development for 5 days at 22-24 C, the development of fungi on the surface of the nutrient solution is evaluated. Assessment: O - no growth of mushrooms, 1 - individual mushrooms on the surface, 2 - 5 - 10% of the surface is covered with mushrooms, 4 - 30 - 60% of the surface is covered with mushrooms, 5 - 60 - 100% of the surface is covered with mushrooms. Effective substances, their concentration in the nutrient solution and the results are shown in Table. 10. Table 1C
    the percentage of leaves affected by melddy, the phylactic processing of leaves is measured, and the Venturia inaeguy fungicidal efficiency is calculated. Result-alls in the open area, tats are presented in Table. 11. Time-Blon shoots, in growth, live untreated plants reaching the MM-TOB variety are treated with capping agent. 0.1% of the test compound. After drying, the applied layer is sprayed with a suspension of spores (330,000 per ml) of leaves, and immediately thereafter, the shoots are covered with plastic bags for 3 days to infect the plants with fungi. After that, the bags are removed. After 2.5 weeks, the percentage of damaged surface is determined as percentage. Untreated control plants show damage. Compound efficacy,%: Compound 18100 1985 Example 16. Effectiveness of the curative treatment of plants against Venturia inaeguali8 block scabs in the open area. Blon shoots, which are in growth variety MM-106, are sprayed with a suspension of spores (330,000 per 1 ml), covered with a plastic bag, and kept wet. The plants are in the penumbra. After three days the bags are removed. After 7 days, the plants are treated with drops of the active substances by spraying at a concentration of the test substance O, 1%. After the next 1.5 weeks, the number of scabs on the affected leaf surface is determined, which in the case of untreated samples is 99%. Compound efficacy,%: 293 18100 19100 Comparable compound: 2-Butyl-3- nitrate (imidazol-1-yl ) -2-Phenylpropionitrile 90 Example 17. Prophylactic treatment of barley leaves against Venturia inaegualis. The barley plants at the development stage of the first leaf are sprayed with the indicated ft in table. 12- substances with a certain concentration when adding alkarylpolyglycolic acid as a wetting agent (0.05%). After the applied layer dries, these plants, as well as untreated control plants, are uniformly treated with infected mildew barley plants and placed in a greenhouse and incubated. Example 18. The effectiveness of the leaf refining treatment of leaves against seed leaves (green beans) in the greenhouse. Plants of bushy beans at the stage of development of half of the first leaf are sprayed with active substances with a concentration of 100 ppm. After the applied layer dries, the treated plants and untreated control samples are sprayed with a suspension
    3) IU
    dispute Uromyces appendiculatus. The plants are then kept for 2 days in a humid chamber at and after that under greenhouse conditions at approximately 22 sec. 11 days after spraying, the number of rust sites was calculated (an average of 253 per leaf of untreated samples). Fungicidal effectiveness is calculated by the formula.
    The number of diseased sites in the treated samples
    100.:
    The number of diseased sites in the untreated samples
     % efficiency.
    The compounds show an efficacy of more than 90%. Efficiency of connections,%: 1 2
    91
    96
    3
    95
    four
    9A
    12
    100
    15
    99.5
    sixteen
    95
    17
    99.4
    18
    99.9
    nineteen
    98
    21
    98.6
    22
    95
    27
    95
    28
    97
    Example 19, the effectiveness of prophylactic treatment of leaves of barley against Helminthosporium teres, the causative agent of diseases of the net spots
    Young barley plants at the stage of development of the first leaf are sprayed with drops of active substances with a specified concentration. After the sprayed layer has dried, the treated plants and untreated control plants are sprayed with a suspension of Helminthosporium teres spores and placed in a greenhouse for 2 days at 20-22 C. A week after infection, the percentage of leaves of tufts is noted. Fugicidal activity is calculated according to the formula of Example 4 in tab. 13.
    32
    EXAMPLE 20: Effectiveness of prophylactic treatment of barley leaves in a climate chamber growing plants against yellow rust. Puccinis Ariformis. Young barley plants at the stage of development of the first leaf are sprayed with active compounds with the indicated; l4 concentrations After the sprayed layer has dried on, the plants and untreated control samples are sprayed with a suspension of Puccinis Ariformis in 1,1,2-trifluoro-1, 2,3-trichloroethane and incubated .3 the plant trapping chamber at. air is close to aasa (enoia. After 15 days, the percentage of leaf surface affected is determined; rust. Fungicidal activity is determined by the formula of Example 4. T a b i c a 14 Example 21 climate chamber growing plants anti-Helmintosporium sativum.The seeds of barley at the artificial attack of H. sativum are pollinated with a compound with the consumption rate fSO g compound per 100 kg of seed 06. working or untreated seeds are sown 2 g in plastic pots of 6.5 X 6.5 cm Sand is used as a substrate. Each experiment is repeated twice. The pots are placed in a plant growing chamber at 16.degree. C. After 4 weeks, the germinated plants determine the percentage of steels. From the average obtained from the experimental results, the fungicidal efficacy is calculated according to the formula of Example 4. Compound efficacy,%: Compound Comparable compound: 2-Butyl-3- (imide3ol-1-yl) -2-phenylpropionitrile 98.5 Nitrate 2-butyl -3- (imidazol-1-yl) -2-phenylpropionitrile 98 Example 22. Action against jpseudomonas phascolicola fatty pathogen in vitro in peas. After sterilization by heating, bio-malt agar is cooled before and then mixed with the test substance to form an aqueous finished preparation, after which it is drunk in a polymer petri dish. After the culture medium is solidified, the plates with the treated and untreated agar as the control samples are infected with a suspension of the Pseudomonas phascolicola fatty agent pathogen in the center using a vaccination. The plates are then incubated at. After 2.5 weeks, the radial spread of the grown bacterial colonies is measured. From the average obtained from two repetitions for each sample, calculate the inhibitory effect according to the formula Radial growth in processed-. "100 Radial growth in untreated% inhibitory effect Braking effect of 250 pps of effective substance in agar against Pseudomonas phascolicola,%; 371 471 1167 1286 1378 1575. 1767
    37111433438
    (Organic or inorganic acids can be used to treat seeds against lots of the general formula J, which are abnormal diseases carried by seeds. They cover a wide spectrum of biocidal activity, and: aean compounds act and exceed the known compounds i.e. they absorb the same structure and direction with the roots of plants, for example, after the action has been introduced.
    The compounds have a broad spectrum against pathogens. Danrom fungicidal action. When the compounds also regulate the growth of the i5oTKe of the ground part of the plants, they plant plants and provide bactericidal protection against pathogens, action.
    aboveground part of plants and protect.
    权利要求:
    Claims (1)
    [1]
    A method of obtaining derivatives of imidazolylpropionitriles of the General formula
    OKx rd-dH dN monogda where R is phenyl, unsubstituted, clis disubstituted by halogen, C ^ -C 4 alkyl or C ^ -C 4 alkoxy, R (- C | -C {0 -alkyl, C ^ -Cg-alkenyl or phenylalkyl residue, or their salts of organic or inorganic acids, characterized in that the compound of General formula
    Okt 0
    Rd - dN 2 ojSdH 3 dN о where Rh R | have the indicated values; they are reacted with imidazole in dimethylformamide medium to isolate the desired product in free form or as a salt of an organic or inorganic acid.
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    同族专利:
    公开号 | 公开日
    BR8203803A|1983-06-28|
    TR21402A|1984-05-22|
    DD202977A5|1983-10-12|
    PL129716B1|1984-06-30|
    PL237145A1|1983-02-14|
    IL66164D0|1982-09-30|
    SE8204027D0|1982-06-29|
    BG37373A3|1985-05-15|
    CH655311A5|1986-04-15|
    FI822033A0|1982-06-08|
    RO85277B|1984-10-30|
    FR2519635A1|1983-07-18|
    BE893696A|1982-12-29|
    DK291582A|1982-12-31|
    AR231440A1|1984-11-30|
    AU8546482A|1984-01-05|
    MA19512A1|1982-12-31|
    KR840000506A|1984-02-22|
    IT8221939D0|1982-06-18|
    IT1151802B|1986-12-24|
    GB2101995B|1985-05-22|
    ATA247082A|1986-04-15|
    RO85277A|1984-09-29|
    ZA824688B|1983-04-27|
    GB2101995A|1983-01-26|
    PT75147A|1982-07-01|
    SU1245251A3|1986-07-15|
    PH19047A|1985-12-11|
    SE8204027L|1982-12-31|
    ZW13182A1|1982-10-20|
    NL8202339A|1983-01-17|
    FI822033L|1982-12-31|
    CA1186317A|1985-04-30|
    JPS588070A|1983-01-18|
    DE3125780A1|1983-01-13|
    HU189598B|1986-07-28|
    YU125882A|1985-03-20|
    FR2519635B1|1985-02-01|
    ES8304092A1|1983-03-16|
    ES512949A0|1983-03-16|
    GR81396B|1984-12-11|
    IL66164A|1985-06-30|
    LU84246A1|1983-01-20|
    PT75147B|1984-05-25|
    NO822231L|1983-01-03|
    CS236480B2|1985-05-15|
    JPS6055070B2|1985-12-03|
    NZ200967A|1985-07-12|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US4167576A|1977-10-06|1979-09-11|Rohm And Haas Company|Cyanoaralkylheterocyclic compounds|
    DE3175673D1|1980-11-19|1987-01-15|Ici Plc|Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them|DE3329213A1|1983-08-10|1985-02-21|Schering AG, 1000 Berlin und 4709 Bergkamen|AZOLYL PROPANNITRILE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE BIOCIDES CONTAINING THEM|
    DE3644616A1|1986-12-29|1988-07-07|Lentia Gmbh|IMIDAZOLE DERIVATIVES, METHOD FOR THE PRODUCTION AND USE THEREOF|
    JPS63120362U|1987-01-28|1988-08-04|
    JPH0624355U|1991-07-12|1994-03-29|株式会社三輝産業|Battery charger|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19813125780|DE3125780A1|1981-06-30|1981-06-30|IMIDAZOLYL-PROPIONITRILE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE BIOCIDES CONTAINING THEM|
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