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    • 专利摘要:
    1425621 Fungicidal application of cyano substituted acetamide derivatives EI DU PONT DE NEMOURS & CO 15 March 1973 [15 March 1972 7 Feb 1973] 12458/73 Heading A5E A composition for combating fungus disease in plants comprises an inert diluent and a compound of the general formula: wherein R is hydrogen; alkyl of 1 to 13 carbon atoms; alkyl of 1 to 13 carbon atoms substituted with alkoxycarbonyl of 2 to 4 carbon atoms, acyl of 2 to 4 carbon atoms. acyloxy of 2 to 4 carbon atoms or cyano: acyl of 1 to 4 carbon atoms; alkoxycarbonyl of 2 to 4 carbon atoms; aralkyl of 7 to 10 carbon atoms; or a non-phytotoxtic metal; R, is alkoxy of 1 to 4 carbon atoms or -NR2R3; R2 is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxycarbonyl of 2 to 4 carbon atoms or R3 is hydrogen or alkyl of 1 to 4 carbon atoms with the proviso that R3 is H when R2 is alkoxycarbonyl or formula III shown above R4 is hydrogen or alkyl of 1 to 4 carbon atoms; R5 is hydrogen or alkyl of 1 to 4 carbon atoms; and X is oxygen or sulfur; with the proviso that when R<2> is hydrogen, alkyl or alkoxycarbonyl, said composition is not a simple solution of said compound in water or an organic solvent. Typical compounds used are 2-cyano-2-hydroxyiminoacetamide, 2-cyano-2-methoxyiminoacetamide, N- carbamoyl-2-cyano-2-methoxyacetamide, 2-acetoxyimino-2-cyano-N-methyl acetamide, and N- (methyl - carbamoyl) -2-cyano-2-methoxyimino acetamide. Optional composition ingredients are surfactants, film forming polymers, humectants, non-phytotoxic oils, insecticides, miticides, bactericides, nematicides, fruit-set agents, fruit thinning compounds, fertilizers and other fungicides (especially benomyl, maneb, captafol, metiram, chlorothalonil, daconil and zineb).
    公开号:SU736856A3
    申请号:SU731890161
    申请日:1973-03-14
    公开日:1980-05-25
    发明作者:Хэйес Дэвидсон Сидней
    申请人:Е.И.Дюпон Де Немур Энд Компани (Фирма)；
    IPC主号:
    专利说明:

    one
    The invention relates to chemical plant protection agents, specifically, to a method of controlling fungal plant diseases by treating them or their biotope with oxime derivatives.
    A fungicide is known, the active substance of which is the manganese ethylene bis-dithiocarbamic acid salt (maneb) 1.
    It is also known that oxime derivatives, for example, 1-cyano-O-carbomoylformaxim 2, N-aryl-substituted oxime carbamates exhibit pesticidal activity 3.
    However, the activity of these compounds at low doses of the drug consumption is insufficient.
    The aim of the invention is to find a new method of controlling fungal diseases of plants with enhanced efficiency.
    /
    This is achieved by treating them or their biotope with an active substance of the formula
    S "(f
    (1) R — O — N — C — C — R
    2
    where r
    hydrogen, alkyl s, acyl containing 2-4 carbon atoms, ethylacetate, etiloxy, alkoxy, Icarbonylmethyl methyl cyano, propyl cyano, hexyl cyano, alkylenephenyl, a metal selected from the group consisting of sodium, calcium, manganese /
    Yu
    RJ is a group, NR2R3 / where Rj is hydrogen or a group
    I,
    WITH/
    15
    R is hydrogen,
    R4 is hydrogen, alkyl,
    RP is hydrogen, methyl;
    2 &
    X - oxygen, sulfur, in the amount of 0.1-20 kg / ha.
    The compounds of formula 1 are processed into various preparative forms: wettable powders, water-soluble powders, suspensions, emulsifiable, concentrates, dusts, solutions, granules, tablets. They are prepared by conventional methods - common in the manufacture of pesticide preparative forms.
    Predpagay (compounds can be obtained by various methods, for example, by nitro-oxidation of cyanacetic acid with sodium nitrite and acetic acid; from the corresponding hydroxyamyl porous and silk cyanide or c &amp; 1 of its own mineral.
    Example 1. The active substance is dispersed in water in an amount sufficient to obtain a coaceum of the active compound equal to 400. A portion of the resulting dispersion is diluted to a concentration of 80. The dispersion is sprayed on the ground where plants and tomatoes are planted in the growing pot and allowed to dry. Both treated and untreated plants are infected with a suspension of spores of Ptra-cbphfhbrQ ihtestans and kept for a day in a chamber with saturated. ton moisture. After five days of additional va aurge in feittMite, all loose tomatoes perish due to blight. Plants that were treated with a suspension with a concentration of 80 million active compound had occasional limited damage to f, while plants treated with a suspension of 400 million concentration were healthy without any signs of disease.
    EXAMPLE 2 Tomato seedlings grown in a vegetative vessel in a greenhouse are contaminated by spraying them with a suspension of PhijiopVi-lViora in estan &apos; t 4 plants incubated for eight hours in a chamber with saturated humidity. Infected tomato plants are removed from the incubator of the cell chamber and sprayed with various active compounds, 1) add to the disease, as well as; by the formation of these compounds, dispersants, with a concentration of the active compound, 400 million, containing 2-cyio-2-hydroxyimoacetamide. Similar dispersions are prepared from fungicides with the trade name: maneb, capt. Atop, metiram /
    AT . 1 shows the degree of inhibition of late blight in s &amp; from the active active principle of the formula,
    9 {R-O-I-C-C-NH
    : At a concentration of 80. In 2 shows the degree of pressure of late blight, depending
    736856
    from the active principle active formula
    C o
    -o-ss: mnsmie „
    . at a concentration of 80 million
    In tab. 3 shows the degree of suppression of late blight, depending on the active principle of the active formula
     9
    H-0-N-C-CNH CNHCH
    at a concentration of 80 million
    In tab. 4 shows the degree of suppression of late blight depending on the active active principle 0 of the formula
    CN (about
    R-0-N-C-C-NHCNHC, jH5
    5 at a concentration of 8b million
    Table 5 shows the degree of suppression of late blight, depending on the active principle of the formula
    Hq-N-C-CNHCNHC H and
     9
    K-O-N C-CNHCNHCjHq
    -i
    at a concentration of 80 million
    5c table. 6 shows the degree of suppression of late blight, depending on the active principle, formula
     9 L CH ON-C-NHCN
    at a concentration of 80 million 45 For the active acting formula
    CN S
    I-C-C-NH ,, t.pl., 163-165 C,
    70%; for benomyl, 0% damage.
    In tab. 7 shows the degree of suppression of the fungal infection: pain in dependence, on the active action
    at the concentration
      g
    400 million
    Example 3. Healthy, non-infected plants: tomato spray bi-suspensions and mixtures prepared for testing in a similar manner.
    Example 2. Treated plants were kept in a greenhouse for five days, then infected with a spore suspension of Pll iopVrtliova infestatis. After the plants grow, they are treated with foliage.
    . .
    After incubation, untreated plants die because of late blight. Fungicide trading measures ensure good foliar destruction,; however, new foliage is unprotected and severely affected. The results of the experiments are given in table.3.
    In tab. 8 shows the degree of suppression of a fungal disease, depending on the active principle at a concentration of 400 ppm.
    Example 4. Potato field infected with late blight ,. uniformly treated with the composition containing 4-N-carbamoyl-2-cnano-2-methoxyiminoacetamide. The old foliage of each plant has one or two spores of PVi topbtViora infestans. At this stage, the damage to the plants is insignificant, but there is a danger of spreading the Disease. There were deeds of five rows wide and 20 meters long. Plots randomly process the entire field, leaving the raw areas as buffers between the treated plots. In cases after treatment, artificial irrigation conditions are usually created that lead to the spread of the disease. After 7 days, the extent of damage to the plants is determined. The results are shown in table E.,.
    In tab. 9 shows the dependence of the degree of suppression of the disease depending on the concentration and the species.
    Example 51 Suspension with a concentration of 400 million active acting containing
    2-cyano-2-dodecyl-aminoacetamide is dispersed in water. Part of it is diluted to a concentration of 80 ppm. Dispersions mist the areas where the planted blond plants are dredged and allow them to dry. Both treated and untreated plants are infected with a suspension of Ventuvia inaecj.uotis spores and 6 are kept in a chamber with saturated humidity for one day. The degree of inoculation is assessed after 10 days. The results of the experiment are given in table. ten.
    Example b. Tomato plants planted in a vegetative vessel are contaminated by spraying them with a spore suspension of phytop Vititora in estar3. The plant is placed in a chamber with saturated Humidity at 20 ° C for eight hours. : 3 infected tomato plants, removed; cabins from the incubation chamber, spray them with the test compound.
    0 Plants are returned to the chamber with a saturated effect for 24 hours. After an additional p) day-long incubation in the greenhouse, the percentage of healthy foliage in the treated plants is determined.
    In tab. 11 shows the degree of inhibition of the disease. Depending on the structure of the active principle of the formula
    0
    T C-C-CN n O
    at a concentration of 80 million
    Thus, the compounds proposed have a high fungicidal action.
    Table 1
    Continued table. one
    47-49
    163-165
    86-87
    - (CH); NB - (CH) S, N ..
    C H
    --fl 2L
    CH (CH),
    / I CH (CHj) CCH
    (CHj) CN
    O (skid
    CH (CH.j) (H {CH) CN
    OK
    140.5-142
    . CH, jCH (CH, j) 90.5-92
    "For the Ca and Mp salts of the compounds of formula 1, the absorption bands of the IR spectra are shown in microns.
    100
    60
    70
    90,100,100
    70
    80 90 70
    .80 70 70
    70 20
    Table
    Continued table. 2
    Table 3
    eleven
    736856
    Continued table. four
    Table 5,
    Table 6
    13
    .Compound
    Raw control
    2-Cyano-2-oxyiminoacetamide
    Maneb.
    Captafsl
    Metiram
    Raw control
    4-M-Car bamoyl-2-cyano-2-methoxy-amino acetymide
    Maneb Captafol Metiram Chlorotalonil
    Raw control
    2-Cyano-2-dodecyl iminoacetamide
    .Maneb
    Unprocessed
    14 Table 1
    Degree of suppression f%
    Table 8
    95
    ten
    15
    five
    T a b l and c a 9
    95
    90
    20 15 10 25
    ABOUT
    -Tables 10
    95
    100
    100 100
    Table 11
    权利要求:
    Claims (1)
    [1]
    Claim
    A method for controlling fungal diseases of plants by treating them or their biotope with an active substance, characterized in that, in order to increase the efficiency of the method, the treatment is carried out with an active substance of the general formula
    С1Ч x ron = ccr 4 where R is hydrogen, alkyl СС -С13 .., acyl containing 2-4 carbon atoms, ethylacetyl, ethyloxy, alkoxycarbonylmethyl С ^ -Су., Methylcyano, propylcyano, hexylcyano., Alkylene phenyl C 4 -Cj , a metal selected from the group consisting of sodium, calcium, manganese;
    - - the group NR ^ Rj, where Ro · - hydrogen or the group CN'f * 4 ", * 5 • R ;, - hydrogen ,,
    TSNIIIPI Order 2455/49
    Cd is hydrogen, alkyl-C + , Rg. -. hydrogen, methyl;
    X ° - oxygen, sulfur. . in the amount of 0.1-20 kg / ha.
    40 Priority on grounds; 03/15/72 at. R is hydrogen, ί-13 alkyl, acyl., Containing 2-4 - carbon atoms, alkoxycarbonylmethyl C ^ -C £, a metal selected from the group
    45 consisting of sodium, calcium, manganese, R ^ - NR ^ R 3 , where Rj is hydrogen or the group _CN VR5 , Rj is hydrogen, R 4 is hydrogen, Ry is hydrogen.
    50 07.02., 7 3 at R - ethylacetyl, ethyloxy ·, methylcyano, propylcyano, hexylcyano, alkylene phenyl C ^ -Cj, Rj - alkyl C 4 -Cd, Ry - methyl ..
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    引用文献:
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    US23499772A| true| 1972-03-15|1972-03-15|
    US33045773A| true| 1973-02-07|1973-02-07|
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