• 专利附录
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  • 权利要求
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    • 专利摘要:
    The invention relates to new compounds of the general formula I <IMAGE> (I) wherein R1 is a straight or branched chained alkyl having 1 to 13 carbon atoms, optionally substituted with halogen, alkoxyalkyl containing 1 to 5 carbon atoms in the alkoxy and 1 to 4 carbon atoms in the alkyl moiety or phenyl; R2 is alkyl having 6 to 20 carbon atoms; alkoxyalkyl, phenoxyalkyl, furfuryl, cyclopropyl-alkyl, cyclopentyl, cycloheptyl, thiazolyl, triazolyl, thiazolinyl, pyridinyl, picolyl, benzimidazolyl, piperonyl, pirimidinyl, chlorobenzothiazolyl, benzyl, phenyl substituted with chloro and/or amino, or amino and alkyl, or amino and nitro groups, alkenyl, alkinyl, aminoalkyl, dialkylamino-alkyl, alkylaminoalkyl, alkylphosphonateammoniumalkyl, 3,5-dichlorophenyl-hidantoinyl, or thiadiazolyl optionally substituted with alkyl; R3 is hydrogen, phenyl, benzyl, alkenyl, alkyl, hydroxy, alkoxy or alkoxyalkyl; or R2 and R3 together stand for a 3,5-dichlorophenyl-hidantoinyl group; R4 is hydrogen or alkyl optionally substituted with hydroxyl. The new phosphoric acid monoester salts of the general formula I show fungicidal activity. The fungicidal compositions containing said compounds as active ingredients are also within the scope of the invention. According to a further aspect of the invention there is provided a process for the preparation of the new compounds.
    公开号:SU1273363A1
    申请号:SU823440451
    申请日:1982-04-01
    公开日:1986-11-30
    发明作者:Герег Каталин；Боднар Ласло；Дудар Эржебет；Кочиш Мария；Гаал Шандор；Ташнади Марта；Эдьхази Ева；Варга Валерия；Кайати Иштван；Киш Дьердь；Молнар Янош；Тот Берталан；Черхати Илона；Капташ Тибор；Чете Шандор
    申请人:Боршоди Ведьи Комбинат (Инопредприятие)；
    IPC主号:
    专利说明:

    This invention relates to the chemistry of organophosphorus compounds, namely, salts of phosphorous acid monoesters of the general formula where, when R, is lower alkyl, R and R2 are furfuryl, 3-isonyloxypropyl, 3-ethoxypropyl, 3-methoxypropyl, 3-butoxypropyl, cyclopentyl, allyl , 1-propinyl-3, 3-dimethyl, 2-thiazolyl, 2-, 3-or 4-pyridinyl, 3-picolyl, 4-thiazolin-3-yl, 3,4-dichlorophenyl, 2-benzimidazolyl, methoxyethyl, 1,254 -triazol-3-yl, 2- or 3-aminopropyl, b-aminohexyl, 3,3 dimethylaminopropyl, nonyl, tetradecyl, hexadecyl, octadecyl, pentadecyl, decyl, piperonyl, cycloheptyl, 2-ethyl xylyl, aminophenyl, 2-pyrimidinyl, geksametilenammoniyetilfosfo tension, 1,2 (or 1,3) -ppopanammoniyetil focfonat, 4-chloro-benzothiazol-2yl, tridecyl, dodecyl, benzyl, tridetsilOksipropil; or H, Rj, and R are allyl, methoxy ethyl, ethylhexyl; or R is benzyl, RO is methyl, isopropyl, or R4 is methyl, R and Rj are allyl, tridecyl (or R is 2-ethylhexyl, R is methyl; or, at R, is tridecyl, Rj is amino-pheni. P, RJ and R are H which possess fungicidal activity and can be used in agriculture. The aim of the invention is finding compounds with increased fungicidal activity. The invention is illustrated by the following examples. Example 1. Amononyl Oxypropyl-ammonium methyl phosphonate (Compound D ) To a mixture of 11 g (0.1 mol) of dimethylphosphite, 20 MP of water and 20 mp of methanol is added dropwise at room temperature in for 15 minutes a solution of 20.13 g (0.1 mol) of 3-isononyloxypropylamine in 30 ml of methanol.The reaction mixture is boiled for 4 hours under reflux, after which the solvent and the ethylene formed are distilled off under reduced pressure. 28.2 g of the target compound in the form of an oily liquid. Yield 94.8% of theoretical. Calculated,%: C, 52.49; H, 10.84; N, 4.71; G, 10.42. 52.29; H 10.68; N 4.57, P 10.30. According to thin-layer chromatography, the resulting product does not contain impurities. The IR spectrum of the compound obtained corresponds to its structural formula, and it contains the following characteristic lines: 2900 (broad line) NH, 1210 2320 PH 1115 C-C-C 16301055 aS P-O-C 1540 NH; 990 P-0 1380 CH CHE 1460 770 S P-O-C 1365 EXAMPLE 2, 2-Ethoxypropylammonium methyl phosphonate (compound 2). A mixture of 11 g (0.1 mol) of dimethyl phosphite, 20 ml of water and 20 ml of methanol and a mixture of 10.30 g (0.1 mol) of 3-ethoxypropylamine and 30 ml of methanol is carried out, as described in Example 1 As a result, 19.7 g of target compound are obtained. The output of 98.9% of theoretical, p 1.4425. Calculated,%: C, 36.17; H 9.10; N 7.03; R 15.56. Found,%: C 35.20; H 9.05; N 6.94; R 15.37. According to thin-layer chromatography, the resulting product does not contain impurities. PRI me R 3. 3-Methoxy-propylammonium methyl phosphonate (compound of formula 3). The reaction is carried out as in example 1, using as starting materials a mixture of 11 g (0.1 mol) of dimethyl phosphite, 20 ml of water and 20 ml of methanol and a mixture of 8.91 g (0.1 mol) of 3methoxypropylamine and 30 ml of methanol . 18.5 g of the desired compound are obtained. The output of 99.9% of theoretical, p. 1,4449. Calculated,%: C 32.42; H 8.70; N 7; 56; P 16.73. Found,%: C 31.20; H 8.63; N 7.14; R 16.45. According to thin-layer chromatography, the resulting product does not contain impurities. The IR spectrum of the compound obtained corresponds to its structural formula. Moreover, it has the following characteristic lines: 2900 (wide line) NHg 1210 cm P O 2320 PH 1115 C-O-C 1630 NH, 1055 aS P-O-C 1540 990 P-0 1380 CH, CHj S P-O -C 1365 P R i m e R 4. H-Butyloxypropyl ammonium meth-phosphonate (compound The reaction is carried out as in Example 1 using a mixture of 11 g (0.1 mol) of dimethyl phosphite, 20 MP of water and 20 ml of methanol and a mixture of 13.12 g (0.1 mol) of 3-butyloxypropylamine and 30 ml of methanol. 22.6 g of the target compound are obtained,. The yield is 99.4% of the theoretical, Pr 1.4420, Calculated ,%: C 42.27; H 9.75; N 6.16; P 13.64. Found: C 41.30; H 9.54; N 6.06; P 13.63. According to thin layer chromatography, the obtained product does not contain impurities. The IR spectrum of the obtained compound corresponds to its structural formula and contains the following characteristic lines: 2900 (wide line) NH 1210 P-0 2320 cm PH 1115 C-O-C 16301055 aS Р-О-С 1540 NH 1460990. 1380 CH СНд 770 S Р-О-С 1365 P P and m E P 5. 3-Ethoxypropylammonium-ethyl-phosphonate (compound 5 Reaction, carried out as in Example 1, and the initial product was a mixture of 13.81 g (0.1 mol) of diethyl phosphate, 20 MP of water and 20 ml of ethanol, and a mixture of 10.31 g (0.1 mol) of 3-ethoxypropyl pilamine and 30 ml of ethanol. As a result, 21.3 g of the title compound are obtained. The output of 99.9% of theoretical, p 1.4445. Calculated,%: C 39.42; H 9.45; N 6.56; R 14.53. Found,%: C 39.40; H 9.30; N 6.69; R 14.05. According to thin-layer chromatography, the resulting product does not contain impurities. Example 6 3-Methoxy-propylamine-ethyl phosphonate (compound 6). The reaction is carried out according to Example 1, using as starting materials a mixture of 13.81 g (0.1 mol) of diethyl phosphite, 20 ml of water and 20 ml of ethanol and a mixture of 8.91 g (0.1 mol) of 3-methoxypropylamine and 30 ml ethanol. 18.8 g of the desired compound are obtained. Output 94.3% of theoretical, pp 1.4450. Calculated,%: C, 36.17; H 9.10; N7.03; R 15.56. Found,%: C 35.97; H 9.28; N 7.17; R 15.48. According to thin-layer chromatography, the resulting product does not contain impurities. Example 7. 3-Isononyloxypropyl ammonium ethyl phosphonate (compound 7). The reaction is carried out as in Example 1, using as starting materials a mixture of 13.81 (0.1 mol) diethyl phosphite, 20 ml of water and 20 ml of ethanol and a mixture of 20.13 g (0.1 mol) of 3-isononyl-oxypropylamine and 30 ml ethanol. The target compound is obtained with a yield of 97.9% of the theoretical, p .. 1,4485. Calculated,%: C, 53.99; H 11.00; N 4.49; R 9.95. Found,%: C 53.80; H 10.97; N 4.28; R 9.73. According to thin-layer chromatography, the resulting product does not contain impurities. P 1 and m e P 8. 3-Butyloxypropylammonium-ethyl-phosphonate (compound 8). The reaction is carried out as in example 1, using as starting materials a mixture of 13.81 g (0.1 mol) of diethyl phosphite, 20 ml of water and 20 ml of ethanol and a mixture of 13.12 g (0.1 mol) of 3-butyloxypropylamine and 30 ml of ethanol. 23.1 g of the desired compound are obtained. The output of 95.7% of theoretical, p 1,4438. Calculated,%: C, 44.79; H 10.02; 5.80; R 12.84. Found,%: C 43.87; H 9.72; 5.27; R 12.85. According to thin layer chromatography, the resulting product does not contain remittances. PRI me R 9. Furfuryl ammonium methyl phosphonate (compound 9). The reaction is carried out as described in Example 1, using as the starting material a mixture of 11 g (1.0 mol of dimethyl phosphite, 20 ml of water and 20 mp of methanol and a mixture of 9.71 g (0.1 mol) of furfurylamine and 30 methanol. As a result, 17.3 g of the desired compound are obtained. Yield: 90.5% of theoretical. Mp: 112-115 ° C. Calculated,%: C, 37.30; H, 6.26; N, 7.25; P, 16.04. Found,%: C 37.02; H 6.23; N 7.14; P 15.97. According to thin-layer chromatography, the resulting product does not contain impurities. Example 10. Cyclopentyl ammonium methyl phosphonate (compound 10) The reaction is carried out as described in Example 1, using This product contains a mixture of 11 g (0.1 mol of dimethylphosphite, 20 np of water and 20 ml of methanol and a mixture of 8.51 g (0.1 mol) of cyclopentylamine and 30 ml of methanol. This gives 18.0 g of the desired compound. Yield 99 % of theoretical, p 1.4463. Calculated,%: C 39.76; H 8.90; N 7.73; P 17.10. According to thin-layer chromatography data, the resulting product does not contain impurities. 4-Dichloro-phenyl ammonium-ethyl-phosphonate (compound 2 Conducts a reaction between 12.00 g (0.05 mol) of 3,4-dichloro-aniline-hydro bromide and 21.0 g (0.15 mol) of diethyl phosphite , dissolved in 50 ml of tolu ol, at 108 ° C. The resulting diethyl bromide is distilled off. After removing the solvent and excess of diethylphosphite from the reaction mixture under reduced pressure, the viscous oily liquid remains, from which the objective compound crystallizes with the addition of ether. Output 72.5% of theoretical. M.p. 64-66 C. Calculated,%: C 35.31; H 4.44; R 11.39; C1 26.02; N 5.14. Found,%: C 35.09; H 4.08; R 11.12; SG 25.97; N 5.11. According to thin-layer chromatography, the resulting product does not contain impurities. Example 12. 3,4-Dichloro-fensh1 ammonium ethyl phosphonate (compound of formula 23). A mixture of 6.08 g (0.044 mol) of diethylphosphite and 1.56 g (0.019 mol) of phosphonic acid at 150 ° C is stirred for 3 minutes, after which a solution of 4.86 g (0.003 mol) of 3,4-dichloroaniline is added to it in 50 ml of anhydrous toluene. The reaction mixture was kept for 1.5 h under reduced pressure at 60 ° C, and then subjected to vacuum distillation. The residue, an oily liquid, is triturated with a small amount of ether. The precipitated crystals are filtered and dried under reduced pressure. The result is the target compound with a yield of 52.8% of theoretical. M.p. 66-67 ° C. Calculated,%: C 35.31; H 4.44; N 5, 14; C1 26.06; R 11.39. Found,%: C 35.18; H 4.42; N 5.11; .C1 26.02; R 11.07. According to thin-layer chromatography, the resulting product does not contain impurities. Example 13. 2-Benzimidazolyl ammonium ethyl phosphonate (compound 2). To a mixture of 27.62 g (0.2 mol) of diethylphosphite and 20 ml of water was added 13.31 g (0.1 mol) of 2-aminobenzimidazole and 150 ml of ethanol. The reaction mixture is heated under reflux for 5 hours, after which the solvent and excess diethyl phosphite are distilled off under reduced pressure. The crystalline precipitate is dried over phosphorus pentoxide. The result is the target compound with a yield of 95% of theoretical. M.p. 155-160 C. Calculated,%: P 12.74; N 17.27. Found,%: P 12.25; N 16.90. According to thin-layer chromatography, the resulting product does not contain impurities. Example 14. Cyclopentyl ammonium phosphonate (compound 22). The reaction is carried out as described in example 1, using as starting materials a mixture of 13.81 g (O, 1 mol) of diethylphosphite, 20 mp of water and 20 MP of ethanol and a mixture of 8.51 g (0.1 mol) of cyclopentylamine and 30 ml of ethanol. 17.9 g of the expected compound are obtained. Output 91.7% of theoretical, p. Calculated,%: P 15.87; N 7.17. Found,%: P 15.69; N 7.19. 7 According to thin-layer chromatography, the resulting product does not contain impurities. Example 15 Tetradecyl ammonium ethyl phosphonate (compound 33). To a mixture of 34.6 g (0.23 mol) of diethyl phosphite, 50 MP of water and 50 mp of ethanol was added a mixture of 53.4 g (0.24 mol) of tetradecylamine and 70 ml of ethanol. The reaction mixture is boiled under reflux for 4 hours. After distillation under reduced pressure of the solvent, 80.7 g of the expected compound are obtained. The output of 99.8% of theoretical. M.p. 45-56 ° C. Calculated,%: P 9.58; N 4.33. Found,%: P 10,12; N 4.50. According to thin layer chromatography, the resulting product does not contain impurities. , P P and m e R 16. Hexadecyl ammonium ethyl phosphonate (compound 34). To a mixture of 34.6 g (0.25 mol) of diethyl phosphite, 50 ml of water and 50 ml of ethanol, a mixture of 60.4 g (0.25 mol) of texadecylamine and 70 ml of ethanol is added. The reaction mixture was heated under reflux for 4 hours. After distilling off the solvent under reduced pressure, 85.2 g of the expected compound are obtained. Output 97.0% of theoretical. M.p. 50-52 ° C. Calculated,%: P 8.82; N 3.98. Found,%: P 8.92; N 4,10. According to thin layer chromatography, the resulting product does not contain impurities. Example 17. Octadecyl-ammonium ethyl phosphonate (compound 35). To a mixture of 34.6 g (0.25 mol) of diethyl phosphite, 50 MP of water and 50 ml of ethanol, a mixture of 67.3 (0.25 mol) of octadecylamine and 70 ml of ethanol is added. The reaction mixture is boiled under reflux for 4 hours, after which the solvent is distilled off under reduced pressure. 88.5 g of the desired compound are obtained. Output 93.2% of theoretical. M.p. 54 Calculated,%: P 8.17; N 3.69. Found,%: P 8,69; N 3.68. According to thin layer chromatography, the resulting product does not contain impurities. Properties of the compounds obtained are presented in Table. 1. 63 The fungicidal activity of the proposed compounds was determined by the method of partially infected agar plates on Botrytis cineria and Fusarium oxisporum. The experiment is carried out as follows. Solutions or suspensions of various concentrations are prepared from the test compound. To the resulting solutions or suspensions, add a spore suspension of the corresponding fungus in accordance with 1: 1. As a result, the test compound suspension and spore together give the desired concentration of the fungicidal agent. For example, in determining the fungicidal activity of an agent with a concentration of the active ingredient of 1600 pp.m, 1 ml of a spore suspension is added to 1 ml of a solution with a concentration of the test compound 3200 pp.m. Nutrient medium from potatoes and dextrose is prepared in the usual way and cooled to 60 ° C. 40 ml of the nutrient medium are mixed in an Erlenmeyer flask with a solution of the test compound (the concentration of the solution of the test compound is twice the concentration of the solution, the fungicidal activity of which is: repeated four times) and pour the mixture into Petri dishes (4 cups with a diameter of 10 cm). From agar plates with single-week cultures of the fungi Fusarium oxisporum and Botrytis cineria grown on them, extract the circles with a diameter of 5 mm using a drill for the stoppers and place 4 circles in each of the Petri dishes. Petri dishes are placed in a thermostat and held in it at 25 ° C for 6 days. Evaluation of the fungicidal activity of the tested compounds was carried out according to the diameter of the colonies (in the control experiment, the colonies almost grew together). The results are shown in Table. 2 and 3. It follows from the above results that the proposed fungicidal agents can be used to combat harmful plant fungi. In their fungicidal activity, they are superior to manufactured products, tested for action on Phytophtora (see Table 4). From the top and second and third sources of seedlings grown in the greenhouse
    Tomatoes at the stage when the plants had 4-6 leaves, cut out circles with a diameter of 15-18 mm, which are placed on filter paper and sprayed with the test preparation at the beginning with one, and after drying the sprayed liquid on the other side.
    Petri dishes are placed in two layers of filter paper, placed on it across the microscope slide and sterilized at 100 ° C.
    After cooling, the filter paper is sprayed with sterile distilled water. The circles cut out from the leaves are placed on a glass slide and sprayed with an exciter suspension.
    Petri dishes were incubated for 48 hours at 10 ° C and then at 20-22 ° C until symptoms appeared.
    On the fourth day after treatment, the extent of damage to the seedlings is determined. The effectiveness of the tested compounds is characterized using the following scoring system: O - no damage; 1 - degree of damage 130%; 2 - degree of damage 31-60%; 3 - damage rate 61-90%; 4 degree of lesion 91-100%.
    Formula of invention
    Salts of phosphorous monoesters of the general formula
    R2
    n
    I €
    HNP P-0
    II O R
    where with R, is lower alkyl R and
    Rj furfuryl, 3-isononyloxypropyl, 3-ethoxypropyl, 3-methoxypropyl, 3-butoxypropyl, cyclopentyl, allyl, 1-propins-3,3-dimethyl, 2-thiazolyl, 2,3- or 4-pyridinyl, 3-picolyl, 4-thiazoline- Z-il; 3,4-dichlorophenyl, 2-benzimidazolyl, methoxyztil, 1,2,4-triazol-3-yl, 2- or 3-aminopropyl, 6-aminohexyl, 3,3-dimethylaminopropyl, nonyl, tetradecyl, hexadecyl, octadecyl, pentadecyl , decyl, piperonyl, cycloheptyl, 2-methylhexyl, aminophenyl, 2-pyrimidinyl, hexamethylene ammonium isylphosphonate, 1,2- (or 1,3) -propanammonium ethyl phosphonate, 4-chloro-benzothiazol-1-yl, tridecyl, tridecyl, 4-chloro-benzothiazole, 2-yl, tridecyl, 2-pyrimidinyl
    or when, R and R are allyl, methoxyethyl, ethylhexyl, or R2 benzyl, R is methyl, isopropyl,
    or t is methyl, R and R are allyl, tridecyl;
    or R 2-ethylhexyl, R methyl; or with R, tridecyl, Rj aminophenyl, R, and R4-H, having fungicidal activity.
    Table 1
    Z-Isononyl Oxypropylammonium Methyl Phosphonate
    3-Ethoxypropyl ammonium methylphosphonate
    3-Methoxypropylammonium methylphosphonate
    3-Butosyloxypropyl ammonium methyl phosphonate
    3-Ethoxypropyl ammonium-ethylphosphonate
    94.8 n - 1.4482
    98.9 n - 1, A427
    99.9 n - 1.4A49
    99.4 p - 1.4420
    99.9 p - 1.4445 14.53 14.05 6.56 6.69 8) 3-Butyloxypropylammonium-ethylphosphonate95, 7 9) Furfuryl ammonium methylphosphonate90.5 10) Cyclopentyl-ammonium methyl-phosphones 99 11) Diallylammonium ethylphosphonate93, 4 12) Aplylammonium ethyl phosphonate 73.0
    13) 1-Propinyl-3-dimethylammonium ethylphosphonate, 60 p.
    14) Methyl-diallylammonium-ethylphosphonate66, 4
    15) Thiazolyl-2-ammonium ethylphosphonate 95.1
    16) Pyridinyl-2-ammonium-ethylphosphonate 95.5
    17) Pyridinyl-4-ammonium ethyl phosphonate 84
    18) Pyridinyl-Z-ammonium-ethylphosphonate 98.9
    19) 3-Picolyl ammonium ethyl phosphonate 98.9
    20) Thiazolyl-2-ammonium ethylphosphonate 97.0
    21) Cyclopentyl ammonium ethyl phosphonate 91.7
    22) 3,4-Dichlorophenyl-ammonium-ethylphosphonate72, 5
    23) 2-Benzimidaeolyl-ammonium ethylphosphonate 95.0
    24) 2-Methoxyethylammonium-ethylphosphonate. 84.5
    25) 1,2,4-Trea-3-ammonium ethyl phosphonate89, 6
    26) Furfuryl-ammonium-isopropylphosphonate95, 4
    27) 3-Aminopropl-ammonium-ethylphosphonate95, 5
    28) 2-Aminopropyl-ammonium-ethylphosphonate95, 1
    1,4481
    14.76 14.57 13.3213.2
    15.18 15.05 13.7213.6
    15.18 15.02 13.7213.60
    15.18 15.03 13.7213.60
    14.20 14.03 12.8312.34
    14.60 14.22 13.2013.07
    15.87 15.69 7.177.19
    11.39 11.12 5.145.11
    52,8
    11.39 11.07 5.145.11
    12.74 12.25 17.2716.90
    P 1.4425 16.73 16.38 7.56 7.42
    15.96 15.07 28.85 29.30
    Front - 1.4648
    14.01 14.27
    p - 1.4688
    16.82 16.70 15.20 14.90
    p - 1.4642
    16.82 16.90 15.20 n - 1, A438 12.8412.055,805.27 16.0415.977.257.14 Plavits at 112-1t5 Pd - 1.4463 17.1016.93.7.737.35 14.9515 , 026,756.05 Pd 1.4562 4 "1.4517 18.5418,408,378.52
    iZT;:: ;; i :: ii: i: i: z
    1 29) 6-Aminohexyl-ammonium-ethyl 98, 9 p phosphonate 30) 3 Dimethylamopropyl-ammonium 94, 6 p ethylphosphonate 97.5 p. 31) Nonyl-ammonium-reference phosphonate 32) Tetradecyl-ammonium-ethyl 99, 845 phosphonate 33) Hexadecyl ammonium ethyl 97, 050 phosphonate 14) Octadecyl ammonium ethyl 93, 254 phosphonate 35) Pentadecyl ammonium ethyl 99, 548 phosphonate 36) Decyl ammonium ethyl phosphonate 98.7 p 37) Piperonyl ammonium ethyl ethyl ethyl ethyl eth ethyl ethyl ammonium ethyl phosphonate 98.7 p. Bis- (2-methoxyethyl) ammonium92, 0 p ethylphosphonate 39) Cycloheptyl-ammonium ethyl 99, 0 p phosphonate 40) 2-Etkl-1-hexesh1-ammonium 98, 3 at phosphonate 41) .- Vis- (2- ethylhexyl) -ammonium89, 2 Pd ethyl phosphonate 42) 4-Amine phenyl ammonium ethylphosphonate 94.0 19 43) 3-Lm) 1-phenyl-ammonium-tridecylfdsonate 53.7 A4) Pyrimidinyl-3-ammonium-ethylphosphonate 96.0-5 A5) 4-Aminophenyl-ammonium-trid93, 5 9 cylphosphonate 46) Hexamethylene-di-ammonium-ethylphosphonate96, 3 47) 1,2-propane-di-ammonium-ethyl 99, 8 p phosphonate 48) 1, 3-propane-di-ammoii-ethyl 98, 9 p phosphonate 49) NN-dialll-2-ethnylhexyl-monmonium-ethyl-phosphonate 85, 7 50) 4-Hlrp-benoothiaeolyl-2-ammo 54, 5-nium-ethyl phosphonate
    Continuation of the table.1 8 1,4678 13,6913,1112,38 12,10 1,4536 14,6014,7813,19 12.90 1,443 12,24,105,53,53 9,5810,124,38 4,50 6 8,828,923,98 4,10 2 8.178,693,69 3,68 6 2 9,189,044,15 4,11, 4472 11,5911,555,23 4,99 11,8711,605,36 5.26 9 1, 4460 12.74 12.73 5.76 5.86 13.8613.816.27 6.20 1.4736 1.4472 12.9512.815.85 5.92 8.828.863.98 3.92 1.4530 -194 14,2114,0012,84 12,80 -91 8,328,287,52 7,44 -60 15,1014,9020,48 20,30 -102 8,328,227,52 7,20 18,4318, -208,32 8,10 1 , 4609 21,0620,909,52 1,4655 21,0620,409,52 9,709,204,38 90-9310,51 10,42 9,50 9,11
    Test compound
    Metaksanin
    0,1-N- (2,6-dime tylphenyl)
    N- (2-methoxyacetyl) alanine-methyl ether
    Efosite - A1
    Aluminum Trisethyl Phosphonate
    Connection 1 2 3
    four
    The average diameter of colonies, mm, based on the concentration of the active substance, pp.ga
    16.6
    1.68 17.2
    17
    1273363
    18
    Continuation of table 2 -
    test compound Average diameter of colonies, mm, in
    5300m 1,5
    54O m m 1,7
    Untreated control culture16, 5
    The growth begins, but does not develop further.
    Compound Average diameter of colonies,
    Metaksanin
    0.1 N- (2,2-dimethylphenyl) -n-2 (methoxyacetin) -alanine methyl ether EfositeTrisethylphosphonate
    aluminum
    Connection 1
    2
    3
    4 Compound 5
    6
    7
    8 10
    18
    Continuation of table 2
    based on the concentration of the active substance, pp.m
    1600 I 800 400 I 100
    Table 3 based on the concentration of the active substance, p.p. m
    1600 I 800 G 400 100
    16.5 17.4 21.2
    13,018,5
    00
    15.815.8
    15.315.3
    ram m
    m
    m
    m
    m
    m
    m
    m
    m
    m
    12.5 12.5
    21
    127336322
    Continuation of table 3
    23

    Known compound - diphenylammonium ethylphosphonate
    Growth begins, but does not continue.
    127336324
    Continuation of table 3
    Table 4
    Continuation of table 4
    权利要求:
    Claims (2)
    [1]
    1,2
    2.6
    1,2
    1,2
    1,5
    Continuation of Table 2
    Test subject gcompound The average diameter of the colonies, based on the concentration of the substance, r.sh mm, in asset1600 | 800 | 400 100 53 0 0 m 1,5 54 0 m m 1.7 Untreated control culture 16.5 - • * Growth begins, but not develops further. T a b l Ts a 3 Compound The average diameter of the colonies, based on the concentration of the substance, p.p. m mm, in asset1600 | 800 400 100
    Metaxanine
    0.1 N- (2,2-dimethylphenyl) - ^ - 2 (methoxyacetin) -alanine-meth-
    ether Efosite-a1 16.6 16.5 17.4 21,2 Aluminum Trisethyl Phosphonate 12.5 12.5 13.0 18.5 Compound 1 0 0 0 0 2 14.6 14.6 15.8 15.8 3 13.9 13.8 15.3 15.3 4 w * m m m Compound 5 m tn m m 6 m Yu m m 7 0 0 m m 8 m m m m 10 m m m m 18 10,2 10,2 12.5 12.5
    2!
    Continuation of table.Z
    Compound y -—-——— ~ ----------------The average diameter of the colonies, mm, calculated on the concentration of the active substance, p.p. m 1600 I 800 I 400 | 100 19 8.7 9.2 9.8 10,2 20 5.3 5.8 6.2 • 7.8 21 m m m m 22 m m 5.7 8.2 23 3,5 4.2 5.2 5,4 24 m m 2.7 8.8 25 m 5.2 5.7 9.8 26 5.5 6.7 7.7 9.5 27 4.7 6.1 6.1 7.2 28»♦ 5,0 6.1 6.7 6.9 29th 2.1 3,5 3,7 4.1 thirty 3.2 3,5 3,7 3,7 31 1,5 3.0 3.6 4.2 32 3.0 5.2 5.8 5.9 33 5,0 5.7 6.2 7.5 34 6.1 6.7 6.9 7.3. 35 2.9 3,5 3.9 4,5 36 m 2.2 3,5 4.1 39 m 3.0 3,5 4.1 40 5.1 6.5 6.7 8.2 44 5,6 6.7 7.8 8.0 42 5.7 6.5 6.9 7.1 41 0 0 0 5.7 45 2,3 2.7 3,1 3,5 Compound 46 5.5 6.7 8.3 8.5 47 3,5 3,7 5.7 4,5
    Continuation of table.Z
    Compound The average diameter of the colonies, mm, calculated on the concentration of the active substance, p.p. m 1600 | 800 400 | 100
    Untreated control culture
    3,7 3.9 2.6 3,1 2.7 3.8 τη m 0 m 0 m m m 2,5 4, .1 2,8 5,6 2.0 2,5 3,5 4.2 3,7 4.1 4,5 5.7 2,3 4.1 2,5 2,8 2.0 4.1 12.5
    5.7 5.9 3,5 4,5 4.2 5.3 2,5 3,7 m 2.7 m ID 2,8 6.5 5,0 5.7 4.2 4.8 3,5 3,7 5.3 3,1 4.7 5.2 8.2 10.5 4,5 5.7 2.9 10.1 4,5 5.1
    ** *
    Known compound-diphenylammonium ethylphosphonate Growth begins, but does not continue.
    Continuation of table 4
    T a b l and c a 4 ‘Active Rating in points at time-Active substance personal concentration ak-substance active substance rr. 52000 1000 | 500100 Methyl Compound10 high air formula 1 0 0 0.41,0 0,1-N (2,6-di 7 0 0.4 0.41.4methyl-' phenyl)- .8 1,6 2.0 0.23.2 fifteen N- (2-Me-toxic 19 0 0 12acetyl)- alanine 20 0 0 0.40.8 20 Efosite- 53 0 0 0.41Trisethyl Phosphonate 41 0 0 00.7aluminum
    • A1
    Score in points at different concentrations of the active substance, r.t
    2000 jlOOO j 500 рОО
    0.6
    1.68 17.2
    Efosite - A1
    Aluminum Trisethyl Phosphonate
    MININ w R 11.5 14.3 Compound 1 0 0 0 1,5 2 11.5 11.7 11.7 12.7 3 11.3 11.3 11.5 12.5
    5.3
    Continuation of Table 2
    Test compound
    1600
    The average diameter of the colonies, mm, calculated on the concentration of the active substance, pp
    800
    400
    100
    Compound 11
    Compound 35
    t t t 2.1 0 0 0 0 0 0 0 0 t> t t t 5,6 9.0 9.0 12.3 t t 8.7 10.5 5.3 5.8 5.8 10,2 t t 8.7 8.9 t t 10,2 12.3 t 8.7 8.9 10.5 8.7 9.2 10.5 13,2 5.8 8.5 8.7 8.9 10,2 10.7 10.7 10.7 t t t t t 6.5 7.2 8.5 t t 2.7 8.5 t 6.5 6.7 8.5 t 2,3 3,5 4.2. t 2.0 2,5 3,7 t 6.5 6.7 8.2 t 5.3 6.5 7.8 τη 3 3,5 4 t t 3.0 5.1 0 0 0 2.7
    0 0
    1 2 3 4 5 6 . 7 51) N N-diallyl-ethanol-ammonium ethyl phosphonate 98.7 n * - 1.4726 12.33 12.05 5.57 5.40 52) Tridecyl ammonium ethyl phosphonate 99.0 40-41 10.02 9.98 4,53 4.37 53) Dodecyl ammonium ethyl phosphonate 95.0 31-33 10.49 10.30 4.74 4.38 54) N-benzyl-isopropyl-ammonium ethyl phosphonate 94.5 4 ’- 1.5035 11.95 11.87 5.40 5.67 55) Dibenzyl ammonium ethyl phosphonate 91.7 82-88 10.08 9.96 4,55 4,53 56) Benzyl ammonium ethyl phosphonate 95.7 Pr - 1.5145 14.27 14.12 6.44 6.34 57) Ν-Μβτκπ-Ν, N-di-tridecyl-ammonium-ethylphosphonate 97.2 rip’- 1.4598 6.13 .6.05 2.77 2.85 58) N M-dimethyl-2-ethylhexyl-ammonium-ethylphosphonate 71.9 Pr’- 1.4465 11.59 11.40 5.24 5.20 59) Di-tridecyl ammonium ethyl phosphonate 96.7 Pr’- 1.4585 6.30 6.20 2.85 2.80 60) 3-Tridecyloxypropylammonium ethylphosphonate 98.9 Ex * ’- 1.4555 8.43 8.47 3.81 3.92 61) Tri-hexyl ammonium ethyl phosphonate 99.5 nJ * - ’1.4505 8.17 8.10 3.69 3.85 62) Di-hexyl-ammonium-ethylphosphonate 99.5 Pr - 1.4450 10.49 10.57 4.74 4.65 Table and c 2
    Test compound Average diameter colonies, mm, in based on the concentration of active substance, r.sh 1600 800 400 | 100
    Metaxanine
    O, 1-N- (2,6-dimethylphenyl)
    N- (2-methoxyacetyl) alanine methyl ether 16.6
    16.6
    fifteen
    Continuation of table 1
    1) 3-Isononyloxypropylammonium
    tilphosphonate 94.8F 1,4482 10,42 10.30 4.71. 4,57 Z-Ethoxypropyl ophylammonium methylphosphonate 98.9 % . F 1.4427 15,56 15.37 7.03 6.94 3-Me current cypr opilammonium methylphosphonate 99.9P R well 1,4449 16.73 16.45 7.56 7.14 3-Butosyloxypropylammonium - methylphosphonate 99,4F _70 p - 1.4420 13.64 13.63 - 6.16 6.06 3-Ethoxypropylammonium ethylphosphonate 99.9 „N p and well 1.4445 14.53 14.05 6.56 6.69
    And 1273363 12
    Continuation of Table D
    ........ g ------ 4 I 51 ' 7 6) 3-Methoxypropylammonium ethylphosphonate 94.3‘1.4440 15,56 15.48 7.03 7.17 7) 3-Isononyloxypropylammoniumethylphosphonate 97.9 S ' '1,4485 9.95 9.73 4.49 4.28 8) 3-Butyloxypropylammonium ethylphosphonate 95.7 % ’ 1,4438 12.84 12.05 5.80 5.27 9) Furfuryl ammonium methylphosphonate 90.5 Melts at 112-115 16.04 15.97 7.25 7.14 YU) Cyclopentyl ammonium methyl phosphonate 99P P “ 1.4463 17.10 16.93 7.73 7.35 eleven) Diallylammonium ethylphosphonate 93,4 % =1.4562 14.95 15.02 6.75 6.05 12) Allylammonium ethyl phosphonate 73.0 25% ’ 1.4517 18.54 18.40 8.37 8.52 thirteen) 1-propinyl-3-dimethylammoniumtylphosphonate 60.5 % n x> w1,4481 - - - - 14) Methyl diallylammonium ethyl phosphonate 66,41.4462 - - - - fifteen) Thiazolyl-2-ammonium ethylphosphonate 95.11,5068 14.76 14.57 13.32 13,2 16) Pyridinyl-2-ammonium ethylphosphonate 95.5 n 2 ; - 1,5092 15.18 15.05 13.72 13.6 17) Pyridinyl-4-ammonium ethylphosphonate 841,5312 15.18 15.02 13.72 13.60 18) Pyridinyl-3-ammonium-ethylphosphonate 98.9p e ' 1,5213 15.18 15.03 13.72 13.60 19) Z-Picolyl-ammonium-ethylphosphonate 98.9 2 P © “ 1.5130 14.20 14.03 12.83 12.34 20) Thiazolyl-2-ammonium ethylphosphonate 97.0 ηϊ- 1,5202 14.60 14.22 13,20 13.07 21) Cyclolentyl Ammonium Ethyl Phosphonate 91.7n D “ 1.4622 15.87 15.69 7.17 7.19 22) 3,4-Dichlorophenyl-ammonium-ethlphosphonate 72.564-66 11.39 11.12 5.14 5.1152.866-67 11.39 11.07 5.14 5.11 23) 2-Benzimidazolyl ammonium ethyl phosphonate 95.0 1 55-160 12.74 12.25 17.27 16.90 24) 2-Methoxyethylammonium ethylphosphonate 84.5 in - 1.4425 16.73 16.38 7.56 7.42 25) 1,2,4-Triazolyl-3-ammonium ethylphosphonate 89.6- 15.96 15.07 28.85 29.30 26) Furfuryl ammonium isopropyl phosphonate 95.4 eo P 1) - 1,4648 14.01 14.27 - 27) 3-Ani nopropln-ammonium-e tylphosphonate 95.5 26 p x> - 1,4688 16.82 16.70 15,20 14.90 28) 2-aminopropyl-ammonium-ethylphosphonate 95.1n l - 1,4642 16.82 16.90 15,20
    Continuation of Table I
    ----- G --- G—---, --T] ”7T 6 7 29) 6-aminohexyl ammonium ethyl phosphonate 98.9 Pr »1,4678 13.69 13.11 12.38 12.10 thirty) 3-Dimethylaminopropylammoniumethylphosphonate 94.6 η * ”1, 4536 14.60 14.78 13.19 12.90 31) Nonyl ammonium ethyl phosphonate 97.5 p ”- 1,443 12.24 12.10 5.53 - 32) Tetradecyl ammonium ethyl phosphonate 99.8 45-46 9.58 10.12 4.38 4,50 33) Hexadecyl ammonium ethyl phosphonate 97.0 50-52 8.82 8.92 3.98 4.10 34) Octadecyl ammonium ethyl phosphonate 93.2 54-56 8.17 8.69 3.69 3.68 35) Pentadecyl ammonium ethyl phosphonate 99.5 48-52 9.18 9.04 4.15 4.11 36) Decyl ammonium ethyl phosphonate 98.7 p ”- 1.4472 11.59 11.55 5.23 4.99 37) Piperonyl ammonium ethyl phosphonate 97.6 57-59 . 11.87 11.60 5.36 5.26 38) Bis- (2-methoxyethyl) -ammoniumethyl phosphonate 92.0 Pr - 1.4460 12.74 12.73 5.76 5.86 39) Cycloheptyl Ammonium Ethyl Phosphonate 99.0 p “- 1.4736 13.86 13.81 6.27 6.20 40) 2-Ethyl-1-hexyl-ammonium ethylphosphonate 98.3 p g p '- 1.4472 12.95 12.81 5.85 5.92 41). Vis- (2 ~ ethylhexyl) ~ ammonium ethyl phosphonate 89.2 p ”“ 1.4530 8.82 8.86 3.98 13.92 42) 4-aminophenyl-ammonium-ethyl-phosphonate 94.0 190-194 14.21 14.00 12.84 12.80 43) 3-Lamino-phenyl-ammonium-tridecylphlsulfate 53.7 87-91 8.32 8.28 7.52 7.44 44) Pyrimidinyl-3-ammonium ethylphosphonate 96.0 - 57-60 15.10 14.90 20.48 20.30 45) 4-aminophenyl-ammonium-tridecylphosphonate 93.5 98-102 8.32 8.22 7.52 7.20 46) Hexamethylene di-ammonium ethidophosphonate 96.318.43 18, '20 8.32 8.10 47) 1,2-Propane di-ammonium ethylphosphonate 99.8 = 1,4609 21.06 20.90 9.52 - 48) 1, 3-Propane-di-ammonium-ethylphosphonate 98.9 4 ° = 1.4655 21.06 20.40 9.52 - 49) N. K-diallyl-2-ethylhexylammonium ethyl phosphonate 85.79.70 9.20 4.38 - fifty) 4-Chlorrbeneothiaeolyl ~ 2-ammonium ethylphosphonate 54.5 90-93 10.51 10,42 9.50 9.11
    [2]
    2.6
    Metaxanine
    Control plants
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    同族专利:
    公开号 | 公开日
    RO92074A|1987-07-30|
    AU541337B2|1985-01-03|
    NZ198178A|1985-05-31|
    BE890114A|1982-03-01|
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    SE8105046L|1982-02-28|
    FR2489332B1|1986-09-05|
    PT73578B|1982-11-10|
    ATA370081A|1984-07-15|
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    RO83311A|1984-04-02|
    YU48450B|1998-07-10|
    LU83584A1|1981-12-01|
    CA1255323A|1989-06-06|
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    ES505472A0|1983-01-01|
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    FR2489332A1|1982-03-05|
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    RO83311B|1984-04-30|
    NO812901L|1982-03-01|
    JPS5772994A|1982-05-07|
    JPH0314040B2|1991-02-25|
    CS232717B2|1985-02-14|
    CH649076A5|1985-04-30|
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    BG36787A3|1985-01-15|
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    SE447533B|1986-11-24|
    AU7463581A|1982-03-04|
    YU205981A|1983-12-31|
    ES8302012A1|1983-01-01|
    引用文献:
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    US2824113A|1953-04-06|1958-02-18|Atlas Powder Co|Quaternary ammonium phosphites|
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    SE446595B|1982-11-19|1986-09-29|Chemmar Associates Inc|SELF-INFECTIVE CARPET WITH AN ALKYL PHOSPHATE INFORLIVATE IN THE BACKPROOF|
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