• 专利附录
  • 专利说明
  • 权利要求
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    • 专利摘要:
    The present invention relates to novel compounds of the formula (I) <IMAGE> (I) wherein R1 and R2 are the same or different and stand for alkyl having 1 to 4 carbon atoms optionally substituted by one or more halogen atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, phenyl or lower alkoxy-alkyl group, R3 stands for alkyl having 1 to 6 carbon atoms or alkenyl having 2 to 6 carbon atoms, R4 and R5 are the same or different and represent hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, phenyl, benzyl, phenyl substituted by one or more alkyl having 1 to 3 carbon atoms and/or by one or more halogen atoms, lower alkoxy-alkyl, a group of the formula -(CH2)n-R6, wherein n is an integer between 0 to 3 and R6 stands for a 3 to 7 membered saturated or unsaturated ring comprising 1 to 3 heteroatoms, said heteroatoms can be selected from the group of nitrogen and/or oxygen and/or sulphur, and R4 and R5 can together form with the adjacent nitrogen atom a hexamethylene-imino group. The compounds of the invention exhibit acaricidal, insecticidal and fungicidal activity.
    公开号:SU1588266A3
    申请号:SU853962797
    申请日:1985-09-25
    公开日:1990-08-23
    发明作者:Балог Карой；Домбаи Жолт；Фодор Карой；Грега Эржебет；Лерик Ерне；Мадьяр Магдолна；Надь Йожеф；Пастор Карой；Шанта Пал；Тарпа И Дьюла；Тот Иштван；Урсин Эстер
    申请人:Эсакмадьярорсаж Ведьимювек (Инопредприятие)；
    IPC主号:
    专利说明:

    The nanic phase is dried over sodium sulphate, after which the solvent is distilled off on a rotary evaporator. As a result, 26.8 g , n |, ° 1.4964. The yield is 78%. I The degree of purity of 96.8% (according to gas chromatography). Pure data: 96.8% (according to gas chromatography).
    Calculated,%: N 9.38; S 9.58. Found,%: N 8.64; S 10.01. PREMIR 2. In a round bottom flask (500 ml) equipped with a stirrer, a thermometer and an addition funnel, 18.6 g of N-ethyl-N, N-di-f Propyl-glycine-amide was placed, which was dissolved in a mixture of consisting of 150 ml of toluene and 10.0 g of triethylamine. To the prepared solution with stirring at room temperature was added - 18.9 g of chlorohydride O, 0-diethylthiophosphoric. acid. After the completion of the spin-off, the reaction mixture is stirred for 2 hours at a temperature of 40-50 ° C. After the completion of the reaction, the organic phase is washed with water, suLat over sodium sulfate, and then the solvent is removed. The result is 29.2 g of H-ethyl-L- (0,0-diethylthiophosphoryl) -N ,, N-di (n-propyl) -glycinamide, m.p. 34-35 ° C. The yield of 88%. The degree of purity 99., 8% (according to gas chromatography).
    Calculated,%: N, 8.28; S 9.46. Found,%: N 8.34; S 9,51.
    Example 3. By analogy with the method described in examples 1 and 2, the compounds listed in Table 1 are obtained, corresponding to the general formula
    So
    RiO R, 0
    -N-CH2C-NC
    Iiiv-f
    (I)
    P p and M e p 4. Emulsion concentrate - centrate (1 O EK).
    Put 10 flasks in a flask equipped with a stirrer. (10%), N-ethyl-N7 (0,0-diztiltiofosforil) -N-ethyl-N-phenyl- .. glycinamide, 60 ma.ch, (60%) xylene, 22 ma.h, (22%) dimethylformamide, 5 May. including (5%) octylphenol polyglycol Y 15 20 25,,
    45
    50
    - .. -, of the main air (Tenziofiks AS) and, 3 May. including (3%) nonylphenol polyglycolic ether (Ten sifix TS). The mixture is cleaned up until it becomes completely transparent. After homogenization and filtration, an emulsion concentrate is obtained - a preparation with a biologically active substance content of 10%.
    Stability of emulsion in water with a hardness of 2 and 19.2 (international degree of hardness); in a concentration of 1% after 2 h there is no sedimentation; after 24 hours reversible sedimentation.
    Example 5. Emulsion concentrate (80 EC).
    In the device described in example 4, placed 80 May. including (80%) N-ethyl-N- (0,0-diethylthiophenophenyl) -N, N-di-allylglycinamide, 12 wt.h. (12%) dichloromethane, 4 mch. (4%) octylphenol-polyglycol ether (Tenziophics AS) and 4 wt.h. (4%) nonylphenol polyglycol ether (Tenziofix IS). As described in Example 4, an emulsion is obtained with an emulsion concentrate with an active compound content of 80%.
    Stability of emulsions in water with a network of 2 and 19.2 ° (international hardness rigidity): at a concentration of 1% after 2 hours reversible sedimentation j reversible in 24 hours.
    Example 6O Emulsion concentrate (50 eq.
    In the device described in example 4 - re 4, placed 50 mach. (50%) N-ethyl-N- (0,0-diethylthiofo eforil) -N, N - di- (n-propyl) -glycinamide, 42 wt.h. (42%) xylene, 5.6 wt. Parts (5.6%) alkylphenol polyglycol ether (emulsifier IR-400) and 2.4 wt.h. (2.4%) arylphenol polyglycol ether (emulsogen EC-400). Further, the method is described in analogy with the method described in Example 5. As a result, an emulsion is obtained. concentrate with the content of biologically active substance 50%.
    Stability of emulsions in water with a hardness of 2 and 19.2 ° (international grade is the same): at a concentration of 1% after 2 hours there is no elution .; after 24 h, reversible sedimentation is minimal.
    Example 7. Determination of acaricidal activity on Tetranyebus ur- ± ± ial (arachnoid mite with two tons).
    The Tetranychus infected with tick urinary bean plants are dried, after which fresh bean plants are placed next to these plants. Viable mites move - with during the day. Infection,
    The fifth and sixth leaves of four-week leguminous plants are cut together with the short part of the leaf stem, after which a square (4x4 CM) is surrounded on the reverse side with the help of strips with the addition of ointment. 40-50 ticks are placed on the final surface of the leaf; they are taken from cut and freshly infected plants. Experience preparation.
    The bottom of a Petri bag (10 cm in diameter) is lined with a layer of cellulose wool, after which only the amount of water that cellulose wool can absorb is introduced into the cup.
    The implementation of the spray.
    For the test, 0.5 and 0.1% spraying liquids, obtained from the emulsion concentrates described in examples 5-7, 10, 25, 35, 50 and 80 as a result of dilution, are used for the experiment, and the experience with each concentration is repeated. four times. Spraying is carried out using a laboratory sprayer with a high pressure balloon. The treated leaves are immediately placed in prepared and containing a layer of cellulose cotton wool Petri dishes.
    Evaluation.
    48 h after treatment, the percent mortality is determined. With a statistical assessment of results based on the consideration of mortality, expressed as a percentage of untreated control pests, it is corrected.
    The beginning of the experience: February 14, 1983
    Experience grade: February 16, 1983.
    During the test, the average air temperature was 20 ° C and the humidity was 75%. Results.
    The average of the four measurements is given in Table 2 (the sequence numbers of the compounds are taken from Table 1).
    Example 8. Determination of acaricidal activity as a function of dose.
    The experience of experiment i corresponding to Example 7 is such that the concentration of the preparation applied during the spraying is reduced from 1000 to 25 million
    The moment of the beginning of the experience: January 26, 1984.
    The moment of evaluation experience: January 28, 1984.
    During the test, the average air temperature was 22 ° C and the humidity was 75%. Results.
    Table 3 shows the sequence number of the compound used in the test, the content of biologically active substance in the spray liquid, as well as the percentage mortality of mites Tetranychus urtical. The serial numbers of the compounds used in the test are taken from Table 1.
    PRI me R 9. Determination of acaricidal activity in blond gardens against Panonychus ulmi KOCH (red spider mite infecting fruit trees).
    The mite Panonychus ulmi KOCH is a dangerous blight pest, and as a result, the control of it is very important.
    The experiment was carried out in a Jonathan variety garden planted in 1963 (size m). The purpose of the experiment is to determine the extent to which, as a result of spraying with the preparations according to the invention, fruit trees can be protected from the harm caused by the said tick.
    The experiment was carried out with four repetitions. The processing time:
    July 29, 1983 The amount of spray to spray is 1660 l / ha for concentrations of 0.1% or 0.2%.
    At the time of processing, the temperature was 55% humidity, the RW wind force and 0% cloudiness. Time of evaluation: August 1, 1983 (i.e. after processing July 29, 1983).
    For each plot, an estimate was made by counting the number of ticks five times on 20 leaves of almost the same size.
    Activity is calculated using
    Henderson-Tilton formula (activity-mortality,%):
    Mortality, 2
    , oo. ()
    Tb xca
    where Ta is the number of live ticks at the time of evaluation (after treatment);
    Tb is the number of live ticks at the time of the start of the experiment: (before treatment); Sa - the number of live ticks in
    control experience, carried out without treatment, at the time of evaluation; CH is the number of live ticks in
    control experiment, carried out without treatment, at the time of the beginning of the experiment. The preparations used and the results obtained are presented in Table 4. The numbers of the compounds used in the test are taken from Table 1.
    (serial numbers of the applied compounds are taken from table 1).
    in me
    Example II Determination of acaricidal activity in apricot seed in relation to Vasates sp. The experiment described in Example 9 was carried out in an apricot orchard planted in 1963 with the difference that the fruit trees were not sprayed, but watered with the preparation appropriate for the invention.
    With different amounts of biologically active substances, the experiment was repeated four times. Activity,%, calculated using the Abbott formula:
    ACTIVITY,%
    xuo,
    Example 10. Definition; acaricidal activity in the plum orchard of the Beszterce variety in relation to Ra- nonychus ulmi KOCH (red spider mite infecting fruit trees).
    The experiment in example 9 was carried out in a plum orchard planted in 1963 (size 9K5 m) -. The purpose of the experiment is given in table 6. Example 12. Determination of a ricid activity with respect to
    determination of the extent to which lepitrimezus vitis (affecting
    This mite Panonychus ulmi can be exterminated by spraying with the means according to the invention. Co spraying liquid, cerit 35 EK emulsion concentrate at a concentration of 0.2%. The amount of spray liquid is 890 L / ha.
    At the time of processing - August 30, 1983, the weather conditions are as follows: lp temperature 21 ° С, humidity 67%, wind strength, cloudiness 0%.
    Moments of evaluation: August 30, I983 (before processing), September 2, 1983 (grape mite).
    For the experiment, shade grapes (variety Opporto) are used. processing of grape plants at the time of budding (April 18
    1985) and at the stage of 3-5 small leaves (May 9, 1985). Parameters of 25 EC, which are prepared with the amount of 1000 l / ha, were applied to plants with a quench of 1.2 or 1.8 l / ha.
    The evaluation is carried out under the conditions of
    ca (on the 3rd day after treatment), a covered plantation in front of Geschem (27 May. 6 September 5983 (on December 1, 1985) four times, with each le treatment).
    The value of each plot is estimated by counting five times the number of living mites on twenty leaves of almost the same size. Acaricidal activity calculated using Henderson-Tilton formula
    50
    times on five shoots. On individual shoots, all leaves are rated according to the following scale: O, no infection; 1 - 0-20% (on leaves 1-5 of the remaining tracks); 2 - 21-40% (on the leaves of the remaining tracks, initial leaf deformation may occur); 3 - 41-60% (on leaves 15-25 of the remaining tracks, the deformation of the leaves increases); 4 - 61-80% (on leaves 25-30 of the remaining traces, leaf deformation is strong, beginning to lag behind in development); 5 - 81-100%, (on leaves
    Results.
    The sequence numbers of the compounds used in the test, the number of live, ticks (the average of four repeated experiments), as well as the percentage expressed activity, are listed in Table 5.
    where C is the number of live ticks in the control experiment at the time of assessment:
    ABOUT
    the number of live mites on the treated trees at the time of assessment.
    The results are shown in table 6. Example 12. Determination of acaricidal activity with respect to
    lepitrimezus vitis (striking
    grape leaves mite).
    Vine plants (variety Opporto) are used for the experiment. The processing of grape plants was made at the time of budding (April 18
    1985) and at the stage of 3-5 small leaves (May 9, 1985). Preparations 25 EC, corresponding to the invention, prepared with water in the amount of 1000 l / ha, were applied to the plants at rest in doses of 1.2 or 1.8 l / ha.
    The assessment is carried out under open plantation conditions before Geschem (May 27, 1985) four times, each
    times on five shoots. On individual shoots, all leaves are rated according to the following scale: O, no infection; 1 - 0-20% (on leaves 1-5 of the remaining tracks); 2 - 21-40% (on the leaves of the remaining tracks, initial leaf deformation may occur); 3 - 41-60% (on leaves 15-25 of the remaining tracks, the deformation of the leaves increases); 4 - 61-80% (on leaves 25-30 of the remaining traces, leaf deformation is strong, beginning to lag behind in development); 5 - 81-100%, (on leaves
    more than 50 remaining tracks, shoots are far behind in development).
    The infection rate (F;) was calculated by the scale values determined during the assessment, the following formula: a, -,
    Fj
    P
    where a. - the value of the scale of the individual
    infection;
    f. - frequency number belonging to a separate value of the scale;
    , j, n t the number of all investigated 1 / Tny leaves.
    The sequence numbers and doses of the compounds used in the test, as well as the values of the infection rates are presented in Table 7.
    Simultaneously with the assessment made on an open plantation, for laboratory research, samples are collected by removing five leaves from the top of each bush, the Cites are washed with 25% of the leaves collected in the laboratory with a 0.1% ion exchanger solution, the resulting solution is filtered through filter paper. what is calculated under the microscopic amount of ticks The percentage expressed activity is calculated using the Abbot formula. The number of ticks and activity expressed in percentages are shown in Table. (serial numbers of the compounds used in the test are taken from Table 1).
    Example 13. Determination of acaricidal activity with respect to two-spot spider mites.
    Grape plants (Orrogto varieties) are treated on 14 May 1985 with the corresponding 25 EC preparations in accordance with the invention. Biologically active substances are applied to plants with the application of 700 liters of Pl spray liquid per 1 ha at a dose of 1.8 l / ha.
    The biological activity of the preparation is evaluated on the 3rd and 7th day after the treatment, taking into account the contamination of the leaves collected from the treated and untreated small areas. Tick infestation is determined five times on twenty leaves before treatment and on the 3rd and 7th day after treatment.
    The percentage expressed activity is calculated using the Henderson-Tilton formula. This activity is indicated in table 8.
    Example 14. Determination of acaricidal activity on papn plants.
    8826610
    polyphogotaonemus latus (wide mite).
    The above pest primarily damages paprika plants. The flowers fall, the leaves and shoots deform, the fruit narrows or even bursts, the skin tissue turns into a crust.
    The sprouting paprika plants (variety) were planted on November 10, 1984,
     . r-j - f o-i
    ten
    15
    .20
    thirty
    the presence of bushes: 6.6 bushes / m) is treated with the appropriate means of the proposed invention with the preparations of 25 EC on March 8, 1985 Paprika plants are sprayed with a knapsack sprayer with a high-pressure balloon (Marum type) with a npi-pressure of 1000 l / ha of spray liquid at a concentration of 0.2%.
    At the time of processing, the temperature is 27 ° Cf and the humidity is 60% ,.
    Evaluation.
    Each three times on 25 leaves, count the number of ticks before treatment and three and seven days after treatment. Activity is calculated using (Henderson-Tilton law).
    The serial numbers of the compounds used in the test (taken from Table 1), the number of live ticks (average value of three repeated experiments) and the percentage expressed in the activity of the pre-. put in table.9.
    five
    From table 9 it can be seen that the assessment made on the third and seventh days shows that the duration of action is well distinguished, since the life cycle of the pest is very small (4-5 days).
    In particular, on the back of the upper leaves .; bucket-shaped, there were ticks. In all forms of application of the pest control agent, these parts of plants were only weakly coated with the spray applied liquid. Thus, good activity values, expressed as a percentage, indicate high absorption.
    Example 15. Determination of acarcidal activity on plants; stalk relative to Aculops lycopercici (affecting tomato mite leaves).
    A mite that affects tomato leaves primarily damages plants when 0
    five
    appropriate to the potato crop family. The pest lives and parasitizes leaves, stems and fruits of tomato plants. Damaged leaves have a yellow-brown color, the opposite side at first gives off a silvery sheen and finally the foliage dries out. Until now, the protection against these mites has not been satisfactory.
    Planted tomato plants (cultivar Belcanto; planted on January 20, 1985; presence of bushes: 3, b bite / m) are treated with the preparations of 25 EC on March 11, 1985 corresponding to the present invention. Spraying was carried out using a knapsack sprayer with a high-pressure balloon (type D-3) using 1000 l / ha of water, and spraying was performed with a 0.2% solution of the biologically active substance. The temperature at the time of treatment was 25 C. Evaluation.
    The number of live mites before treatment and 24 hours and 72 hours after treatment are counted for each α-small area on the five leaves. The percentage expressed activity is calculated using the Henderson-Tilton formula.
    Table 10 shows the order number of the applied biologically active substance (taken from Table 1), the number of living ticks (average value of three measurements) and the expressed percentage in activity.
    Example 16. Determination of acaridid activity on cucumber plants with respect to Tetranychus telarius (arachnid mite with two spots).
    Planted cucumber plants (cultivar Tosca-69) planted on February 15, j985, were treated in the I metrigen state of cucumbers at the time of the beginning of their color. On a plot of 10 m, the number of plants was 1.2 pcs / m. Spraying is carried out using a knapsack sprayer (Maru type) using water in an amount of 100 l / ha. Compound 17 according to Table 1 (25 EC) is used in solution form with concentrations of 0.025-0.4%. At the treatment time, the temperature is a humidity of 657.
    five
    ten

    15
    20
    Evaluation.
    Before treatment and 3, 7, 14 and 21 days after treatment, the leaves for each site were examined five times with a microscope. After determining the number of live ticks using the Henderson-Tilton formula, the propentated activity is calculated.
    Table 11 shows the numbers and doses of the compounds used and the activity expressed as a percentage.
    Example 17. Determination of acaricidal activity on soybean plants with respect to various developing forms of Tetranychus urtical KOCH (spider mite)
    The experiments were carried out with a tick-borne tick (the Gyor region), a strain that is resistant to dimethoate and chloropropylate, in accordance with the proposed test methods, respectively, is sensitive to amy-, -tras-, dienochloro- and cyhexatin-compounds. 3566 mobile individuals are observed in experiments; 2234 females, 215 dytonymphs, 390 larvae and 4031 eggs.
    Individuals of the common spider mite are grown on soybean plants.
    Leaves infected with the test tick strain are cut into strips and applied to uninfected plants. Spider mites quickly move to fresh soybean leaves. The leaves of soybean plants infected by this method are kept for 2A h in an artificial climate chamber, MQ TOM, in which, with the aim of contributing to the deposition of eggs, under constant illumination, the temperature is maintained at 25 + 2 ° С and the humidity at
    25
    thirty
    35
    90-95%.
    45 I
    After the end of the holding time
    The leaves are detached from the bush, after which all forms, except the eggs, are removed under a stereomicroscope with a brush.
    50 Remaining on the leaves of the egg of the same age. Petri buckets are put back into the artificial climate chamber, and the leaves containing the form that is in the state of the prototypes of the nymphs are transferred to fresh plants. In living plants, mites develop to reach puberty. The moment of deposition of the first eggs is taken on the first day, and for the experience of using
    13
    They have 3-5 day old females.
    Daytonymphs for 10 days after deposition of eggs, dipping for 8 days, the larvae for 6 days and eggs for 1 and 5 days were treated with 50 EC solutions of compound 9 in various doses.
    In the case of mobile forms, the infected leaves are again cut into strips, the strips are placed on fresh plants, and the treatment with acaricidal preparation is carried out 2–3 hours after the movement of the mites.
    When testing the leaves, the leaves are treated with vagat after removal of the females.
    Of the methods for determining the stability recommended by the PAO (BUDVINE, 1980), the leaf immersion method is used. From the compound used in the test by diluting with distilled water, a series of diluted solutions consisting of brushes of members is prepared,%: 0.28; 0.14; 0.07; 0.035 0.01775 and 0.00875. In all cases, treatment begins with an aqueous control sample containing only distilled water, and the most recent experience is with a sample having the highest concentration. The treatment is performed in a room with a temperature of approximately. Infected and severed leaves are kept immersed in the solution (temperature 22 ° C) for 10 seconds while carefully moving them. The leaves are then gently shaken in order to remove large drops from them. The leaves are then placed in Petri dishes on cotton wool moistened with water, and the edges of the leaves are treated with lanolin in order to prevent the migration of mites. When the drug on the leaves dries, the Petri hats are placed in an artificial climate chamber. The temperature in the artificial climate chamber is 24 ± 2 ° C, the duration is 16/18 hours per day, the illuminance is 800 lx, and the relative air humidity is in the range of 90-95%.
    The evaluation is made under a stereomicroscope, and the number of living and dead individuals is counted. Evaluation of females, age 3-5 days produced on the 1st, 3rd and 7th dec after treatment, and | Deutonymph, protonymph and larvae are evaluated on day 1 and 3 after treatment. When evaluating a killing egg

    ten
    20
    25


    15
    . "
    88266 ..
    four
     the activities separately calculate the ratio of extruded eggs / larvae (living and dead) and the same for proto-and deutonyphs.
    When determining the contact residual effect, the leaves of soybean plants are immersed in a 0.28% solution of compound 17. After 4, 12, 24 and 48 hours after treatment, leaves are placed on the leaves using a lanceolate cannula of a female 3-5 days old. Evaluation was performed seven times a day. In assessing mortality, individuals treated with distilled water are taken into account. The mortality expressed as a percentage is calculated according to the Henderson-Tilton formula.
    Tables 12, 13, and 14 present the results obtained for the various phases of development. Table 14 gives the effect of a 0.28% solution of compound 9 on females (contact residual action).
    Example 18. Determination of acaricidal activity on ornamental plants with respect to Tarsonemus pallidus BNKS (infecting the earth mite).
    It was only in 1968 in Hungary that the land mite was found to cause damage, but until recently this mite was a dangerous pest of landowners. Since the mid-seventies, the Tarsonemus pallidus BAHKS mite has been damaging ornamental plants, and the damage rate and the number of plants that feed this pest have increased from year to year. For this reason, finding effective protection against it is of great importance.
    The experiments were carried out in the metropolitan zoological and botanical garden. Compounds of the present invention 25 EC at a dose of 2.8 p / ha are applied to plants using a hand sprayer (type Pricalica K-12). The temperature in the greenhouse is 0–21 ° C. The following plants are subjected to treatment: Saintpaulia ionantha ( the plants experienced initial symptoms of damage caused by an earth mite), Saxifraga saraentosa (young leaves were severely deformed,
    thirty
    35
    ) jI-1 -. v
    , Fitlania verschaffelta (leaves have already been deformed).
    The assessment is made on the third and seventh days, in both cases from
    - l 51 58
    The plants used in the experiment are separated by five of the youngest leaves, after which the laboratory, using a stereo microscope, calculates the number of living and dead on these leaves, as well as moving individuals (females, males, larvae). In each case, five of the youngest leaves are selected for the reason that the land mite directs its harmful effect only on young leaves and cannot feed on old leaves,
    Knowing the number of all individuals and dead individuals, the mortality is calculated in percent. The results are presented in table 15. The serial numbers of the compounds used in the test correspond to the numbers given in Table I.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    An acaricidal agent containing the active substance - N alkyl-N- (thio-4-pyropyl) -N-substituted aminocarbonic acid amide, solvent and -. superficially active substance, about t - l and h and y, e e with the fact that, in order to enhance, acaridin activity, it as H-alkyl-K- (thiophospho-) zyl) -K-substituted amide of amino carboxy- New acid contains a compound of the general formula
    B o
    H “1
    xP-N-CHgC-l
    Rii
    35
     Ii;
    RS40
    de R j and R, 2 are the same Cc, C (j-alkyl, ethyl chloride, ethyl bromide, ethylene, allyl, cyclohexyl, phenyl, ethoxymethyl, methoxyethyl; C, -C, -alkyl; allyl;
    CL alkyl
    allyl, cyclohexyl, benzyl ,, 3-chlorophenyl, 4-bromophenyl, 4-50 fluorophenyl, 4-methylphenyl, 2,6-diethylphenyl, 2-methyl-6-3 tetylphenyl;
    sixteen
    R is hydrogen, C |, C ,, Sc-alkyl, allyl, cyclohexyl, methoxymethyl, ethoxymethyl, phenyl, thienyl-2, pyrrolidinyl, pyranyl, 2-imidazolyl, 2-imidazo-LIL-4-IL, oxazolyl, . morpholinyl; R4 and Rg together with nitrogen form a hexamethylene-amino group,
    the solvent contains a mixture of xylene and dimethylformamide at a mass ratio of 60:22, or dichloromethane, or xylene, and as a surfactant, a mixture of Tenziofix AS based on octylphenol polyglycol ether and Tenziofix IS based on nonylphenolpolyglycolic ether at a mass ratio 5: 3 or 4: 4 or a mixture of emulsogen EC-400 based on alkylphenol polyglycol ether and emulsogen EC-400 based on arylphenyl polyglycol ether at a mass ratio of 5.6: 2.4 in the following ratio of components, wt.%:
    Active Substance Solvent Surfactant
    Priority featured:
    26.09.84 with R and Rg. - the same C 4, Cj, C (-alkyl, methyl chloride, ethyl bromide, RJ-C-Cg-alkyl, allyl, C-Cd-alkyl, allyl, cyclohexyl, benzyl, 3-chlorophenyl, 4-bromophenyl, 4 fluorophenyl, 2,6-diztilphenyl, 2-methyl-6-methylphenyl, hydrogen, C, C, C-alkyl, allyl, cyclohexyl, phenyl, and R together with nitrogen form a hexamethylene group,
    ZH.U / .OJ lip 11. l P 1 i nrKiixijjsu.si
    ethylene, allyl, cyclohexyl, phenyl, ztoxymethyl, methoxyethyl, R5-- methoxymethyl, ztoxy1-methyl, thienyl-2, pyrrolidinyl, pyranyl, 2-imidazolyl, 2-imidazolin-4-yl, oxazolyl, morpholinyl.
    Compound
    Mortality,%, with concentration, million G
    gooo
    5000
    .21
    1588266 Continuation of table 2
    (C, H, S) (qH.p) P (0) N (,) C (0) NH ()
    22
    Compound
    Mortality,%, with concentration, mln. 100 I 500 150 I 125 100 T 50
    100 100 100
    100 100 100
    100,100 97
    Number of live mites on 5x20 leaves
    before processing
    1105,699 29.8
    1234 242 78.2
    1172 70 93.4
    1093 45 95.4
    1025 645 30
    1086 195 80
    1053 47 95
     - 100
    1201 649 40
    Continuation of table 3
    25
    100 100 93
    100 100 90
    100 00 90
    Table 4
    Mortality,
    after processing
    Serial number and dose applied in compound test
    0.2% spray liquid
    25 35EK
    0.1% sprayer spray
    25 35EK
    0.2% spray liquid
    Untreated control plants
    Continuing tablo
    The number of live mites on the leaves
    before processing
    after processing
    1075
    174
    82
    1250
    34
    97
    1236
    100
    1131
    1019
    ine
    Dose, l / ha
    Infection rate

    , 2 1.8 1.8 1.2 1, 8
    0.95 0.43 0.43 0.12 0.08
    :,four
    T a b a 8
    Connection G Activity
    on the 3rd on the 7th day
     - - - .- .., -., ™., „J
    100,100
    129395
    1696100
     300,100
    239998
     -l i-§-. a 9
    e- Number of live ticks, Activity, W1; / sheet
    before the treatment through the 3rd on the 3rd „and the 7th day of treatment 3 days 7 days a day after the treatment
    38.59 0.16 0.28 99.46 99 76
    ll ll - °: 1о6о
    38 sQn ° 00.0
    - ° "° 0 00.0
    38.5929.93 12K52
    ; - -1-§-5 l dI y and 7,
    Activity,
    eskolzh
    alive mites, pieces on 25 leaves
    92
    100
    100
    95
    100
    291
    ny delight bath
    1st day after deposition of eggs
    Day before hatching
    1st day of early spring
    Day before poured out of it
    1st day after deposition of eggs
    Day before hatching
    1st day after deposition of eggs
    The day before he received
    1st day after deposition of eggs
    Day before hatching
    1st day after deposition of eggs
    The day before he received
     day after deposition of eggs
    Day before hatching
    T a1 3
    h
    2 h
    4 h
    eight
    2 3 4 5 6 7
    one
    2 3 4 5 6 7
    1 2 3 4 5 6 7
    one
    2 3
    4 5 6 7
    100 00 100 100 100 100 100
    100 100 100 100 100 100 100
    100 100 100 100 100 100 100
    100 100 100 100 100 100 100
    92
    97
    100
    100
    100
    100
    100
    72 90 95 98 99 99 99
    40 61 72 85 85 85 85
    12 31 54 66 66 66 66
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    同族专利:
    公开号 | 公开日
    DK434285A|1986-03-27|
    JPS61171492A|1986-08-02|
    AT387577B|1989-02-10|
    AR242796A1|1993-05-31|
    FI79326C|1989-12-11|
    AU573036B2|1988-05-26|
    AU4790785A|1986-04-10|
    NL8502605A|1986-04-16|
    DK434285D0|1985-09-25|
    PL146597B1|1989-02-28|
    BE903304A|1986-01-16|
    FR2570704B1|1989-03-03|
    PT81202A|1985-10-01|
    PL147098B1|1989-04-29|
    NO167575C|1991-11-20|
    PL255529A1|1987-04-06|
    SE8504346L|1986-03-27|
    US4870065A|1989-09-26|
    RO93594B|1988-01-31|
    SE464029B|1991-02-25|
    ATA271985A|1988-07-15|
    CH662814A5|1987-10-30|
    RO93594A|1988-01-30|
    FI853685A0|1985-09-25|
    FR2570704A1|1986-03-28|
    NO853760L|1986-04-01|
    CN85108113A|1987-02-11|
    CA1240992A|1988-08-23|
    SE8504346D0|1985-09-19|
    NO167575B|1991-08-12|
    PL262520A1|1988-01-07|
    JPH0450318B2|1992-08-13|
    IT8522273D0|1985-09-25|
    TR22719A|1988-05-03|
    PT81202B|1987-09-30|
    IT1214632B|1990-01-18|
    FI853685L|1986-03-27|
    FI79326B|1989-08-31|
    LU86096A1|1986-03-11|
    IL76415D0|1986-01-31|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US3280226A|1964-02-05|1966-10-18|Velsicol Chemical Corp|Bis- alkyl amides of phorphorus acid esters|
    DD95374A1|1971-07-05|1973-02-12|
    AT387577B|1984-09-26|1989-02-10|Eszakmagyar Vegyimuevek|METHOD FOR PRODUCING N-ALKYL / EN / -N- / O, O- DISUBSTITUTED THIOPHOSPHORYL / -N'N'DISUBSTITUATED-GLYCINAMIDES AND ACARICIDES, INSECTICIDES AND FUNGICIDES CONTAINING THESE COMPOUNDS|
    US4691500A|1986-07-18|1987-09-08|Packaging Systems International, Inc.|Lid sealing machine|AT387577B|1984-09-26|1989-02-10|Eszakmagyar Vegyimuevek|METHOD FOR PRODUCING N-ALKYL / EN / -N- / O, O- DISUBSTITUTED THIOPHOSPHORYL / -N'N'DISUBSTITUATED-GLYCINAMIDES AND ACARICIDES, INSECTICIDES AND FUNGICIDES CONTAINING THESE COMPOUNDS|
    HU202728B|1988-01-14|1991-04-29|Eszakmagyar Vegyimuevek|Synergetic fungicide and acaricide compositions containing two or three active components|
    CA2054054C|1990-10-31|2002-11-26|Richard David Houghton|Propanil dispersible granule formulation|
    US5714439A|1990-10-31|1998-02-03|Rohm And Haas Company|Propanil dispersible granule|
    DE4342621A1|1993-12-14|1995-06-22|Bayer Ag|Phosphoric acid derivatives|
    MX2013010824A|2011-03-23|2013-10-17|Dow Global Technologies Llc|Phosphorous-containing flame retardants for polyurethane foams.|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    HU843631A|HU194258B|1984-09-26|1984-09-26|Acaricide, insecticide, fungicide compositions and process for producing new n-alkyl-/ene/-n-/0,0-disubstituted-thiophosphoryl/-n-comma above-n-comma above-disubstituted-glycin-amides as active components|
    HU1509285|1985-07-24|
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