• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
  • 法律状态
  • 优先权
    • 专利摘要:
    Microbicides are described which contain, as active ingredient, at least one novel compound of the formula I <IMAGE> where the substituents in formula I have the meanings defined in Claim 1. There is also described a process for the preparation of the novel active substances, which is characterised in that a compound of the formula II <IMAGE> is reacted with a carboxylic acid of the formula III <IMAGE> or an acid anhydride or acid halide thereof, the substituents being as defined above. Moreover, a process is described for controlling phytopathogenic fungi and for preventing fungal attack with the aid of these novel active substances.
    公开号:SU725542A1
    申请号:SU2595003
    申请日:1978-03-27
    公开日:1980-03-30
    发明作者:Экхардт Вольфганг；Кунц Вальтер；Хубеле Адольф
    申请人:Циба-Гейги Аг (Фирма)；
    IPC主号:
    专利说明:

    (54) FUNGICIDE MEANS
    one
    The invention relates to chemical agents for controlling fungal diseases of plants, namely, to a fungicidal agent based on adetanilide derivatives.
    Known N- (1-methoxycarbonylethyl) -K- ((b-chloroethylcarbonyl) -2,6-dimethylaniline, which has fungicidal activity 1.
    This goal is achieved by the formation of a compound of the general formula
    .
    f
    Nc-C "-eH-K ;;
    ABOUT .
    R-,
    2 methyl,
    De
    chlorine or
    ethyl. bromine; B. Carboxylic acid formula. ° - -HLG (br) or acid anhydride or acid halide, or since p-alkoxy-targeted compounds with, CH and H, CH and Rg C -Cj alkoxy are desirable, they are obtained by reacting an intermediate of the formula -SN-CK- L; -jt,. CO-CH-CH-HoI (V) Rj &amp; 7 CO with alcohol or alkali or alkaline earth metal alcohols of the formulas M - KB C. As a result of the addition of alcohol according to Michaelol or his agaogate at ° C f (i-unsaturated anilide of formula 3) Gu CH-Ya5 (vn I II RI, Rg R7 d. As a result of the addition of an elemental halogen, preferably chlorine, bromine or iodine, to a substituted, acrylanilide of the formula of cnc I and further replacement of both halogen atoms in the side chain -CO- CH-CH-HOI Hot at least 2 mol of alcohol (or its alcohol) of the formula V, in which in this case% f-Rg In formulas II-VII, the formula is The values given for formula D, while Na stands for halogen and M represents hydrogen or the metal cation mentioned. Reactions can be carried out in the presence or in the absence of an inert component, the reaction of growth of IL or the diluent. Therefore, the following compounds: aliphatic or aromatic hydrocarbons, such as benzene, toluene, xylenes, petroleum ether, halo hydrocarbons, such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, ether, or ether type compounds, such as diethyl ether p dyo.ksan tetrahydrofuran; nitriles, like acetonitrile; K, N-dialkylated hyine, such as dimethylformamide, dimethyl sulfoxide; ketones, such as methyl ethyl ketone and mixtures of such solvents. Reaction temperatures range from about 0 to preferably between 20 and 120 ° C. In some cases, it is advantageous to use acid or condensation agents. As such, tertiary amines, such as trialkylamine (e.g., triethylamine), pyridine and pyridine bases, or inorganic bases, such as oxides or hydroxides, acid carbonates and carbonates of alkali and alkaline earth metals, such as sodium acetate, should be kept in mind. The preparation of compounds according to method A, in which they originate from compounds of the formula II, can also be carried out without and :: an acid-containing agent, and in some cases (using an acid halide) nitrogen is passed to transmit nitrogen to remove the formed hydrogen halide, in other cases it is it is advantageous to add dimethylformate as a catalyst for the reaction. The compounds of formula I have an asymmetric carbon atom adjacent to x Rg in the side chain and can be split in the usual way into optical antipodes. Since directional synthesis is not carried out to isolate pure isomers, usually the product of fsSmuly I is isolated as a mixture of these possible isomers. Example 1 (according to a variant of method A). V Getting MN rt, 3 rz L; СН-СООСНз / ССНгСНаОСНз с.н N (1-methoxycarbonyl-ethyl) -N-3-methoxypropionyl-2, b-dimethylaminil (compound I). 20.7 g of N- (l-methoxycarbonylethyl) -2, b-dimethylaniline in 150 ml of toluene are mixed at room temperature with 13.5 g of 3-methoxypropionic acid chloride. After boiling for 16 hours under reflux with flowing nitrogen during this time, the reaction solution after cooling is washed with an aqueous solution of soda, dried over sodium sulfate, filtered and the solvent is evaporated. The oily residue is purified by distillation; bp 128-13b ° C / 0.1 mm Hg Example 2 (according to embodiment C). Preparation of N- (l-methoxycarbonylethyl) -Y-3-methoxypropionyl-2, 6-dimethylaniU {yna. 0.23 g of sodium (0.01 mol) races, fucked y in 100 ml of methanol. To this solution, a solution of 13 (0.05 mol) N- (l-methoxycarbonylethyl) -Y-acryl-2,6-dimethylaniline in .50 ml of methanol is added dropwise to the thief at room temperature. The reaction mixture is then immediately boiled for 20 hours with a reflux condenser and evaporated after cooling. The oily residue is introduced into methylene chloride and washed with water. The methylene chloride solution is dried over sodium sulfate, filtered and evaporated. The oily residue is fractionally distilled. Your product boils at 130 136 ° С / 0, 1 mm Hg. Art. Example 3 (according to embodiment c). Preparation of N- (-methoxycarbonylethyl) -Y-3-methoxypropionyl-2, b-dimethylaniline. 2.3 g (0.1 mol) of sodium is dissolved in 100 ml of methanol and 17.1 g (0.05 mol) of N- (l-methoxycarbonylethyl) -N-3-bromopropionyl-g2, 6-dimethyl aniline, dissolved in 50 ml of methanol, is added dropwise at room temperature to a TeMnepatype. The reaction mixture was stirred at this temperature overnight. After evaporation on a rotary evaporator, the oily residue is dissolved in ether and washed with water. The ether solution is dried over sodium sulfate, filtered, and evaporated. The target product is distilled at 129-135 ° C / 0.1 mm Hg. PRI and e p 4. Getting SchNz (jHj / y / sc co-CнCHj-SNOSНОC CHjCHj j jj N- (-methoxycarbonylethyl) -N-3 -megoxybutyryl-2, 3,5, 6-tetramethylaniline (compound 43 ) 7.05 g (0.03 masl) of N- (2,3,5,6-tetramethylphenyl) alanyl methyl ether in 90 ml of toluene are charged into a flask. To this mixture, 4.5 g (0.033 mol) are added dropwise at room temperature. A) 3-methoxy-butyryl chloride dissolved in 10 ml of toluene. While slowly passing nitrogen, the mixture is boiled for 16 hours with a reflux condenser. After cooling and evaporation of the solution in vacuum, a semi-solid residue is added to 60 ml of methylene chloride and this solution is passed through once with 30 ml of 1N NaOH solution and then twice dissolved in 100 ml of water.The organic phase is then separated, dried over Na, SQj, filtered and freed in a small vacuum from methylene chloride. The final product is obtained as a dark brown oil and purified as a result of short-term distillation, bp 131 131 ° C / O, 06 mm Hg. Similarly, using one of the above methods, the following compounds of general formula CH3 are obtained. SI-with OSI, / ic) presented in table. 1. Similarly, the following compounds can be obtained with the formula, CHCP5 (not presented in Table 2. Example 5, Action against Plasmopara viticola (Bert, et Curt) (Berl et De Ton) on a vine. Residual-preventive action. In the greenhouse Shchasla cultivar grapevine seed At the development stage of 10 leaves, 3 plants are sprayed with a broth containing the active substance with a concentration of 0.06% prepared from an effective substance in the form of a wettable powder. After drying the applied layer, the plants are internally infected with a suspension of p fungus. Immediately thereafter, the plants are kept for 8 days in a humid chamber. After that, the obvious symptoms of the disease on the control samples. The number and size of infected sites of the treated plants serve as a measure of the effectiveness of the tested compounds. No. 1, 9, 11, 18, 23, and 26, fungal infection was completely prevented. (Example b) Action against PhytopKtora Infestahs on tomatoes. 1. Curative action. After a three-week germination, plants of the Red Dwarf tomato variety are sprayed with a suspension of spores of the fungus, then they are kept in a chamber at a temperature of 18-20 seconds and saturated air humidity. Moistening is stopped after 24 hours. After the plants have dried, they are sprayed with broth, which contains an effective substance, in the form of a wetting powder with a concentration of 0.06%. After the applied layer has dried, the plants are again placed in the greenhouse for 4 days. The number and magnitude of typical spots on the leaves that have occurred during this time serves as a method for assessing the effectiveness of the test substances.
    Ii. Preventive systemic action.
    An effiguous substance in the form of a smechiagiedegss powder with a concentration of about, 006% (calculated on the volume of the earth) is applied to the ground grown for 3 weeks in pots of tomato plants of the variety Red Leprechaun. After keeping for 2 days, the inside of the plant is sprayed with spores / Phytophtora Infestans. Then, for 5 days, plant notiieiiaraT in a humidified cabin at 18–20 ° C and saturated air humidity. After this time, typical spots appear on the leaves, the number and size of which serve to evaluate the effectiveness of the tested compounds.
    In both experiments, the known compound N- (1-methylthiocarbonyl ethyl) - f-meccylacetyl-2, 6-dimethylaniline (compound A) was used as a comparison.
    Test 1: the fungal infection was completely prevented by compounds I 2,9,11,12,18,21 and 23, and compounds (19 and 23, also at a concentration of 0.02%. For compound A, the fungal damage was 5 -20%.
    Experience II; the fungal infection was completely prevented by compounds 1-11, 14-27, and by compounds nos. 1.2, 4.5, 6, 9, 11, 17, 21, and 23, also at a concentration of 0.002%. For compound A, the fungal injury was 0-5%. Example 7. Action against Erysiphe gremlin is on barley.
    Residual-protective action.
    Barley plants about 8 cm long are sprayed with broth (0.06% of active substance) prepared from a wettable powder of an effective substance. After 48 hours, the treated plants are sprayed with spores of the fungus. Infected barley plants are placed in a 5th greenhouse and are maintained approximately for 10 days and the fungal damage is assessed.
    Compounds Nos. 20 and 34, with full 0, prevent fungal infection.
    For compounds 3, 11, 23, and 27, the lesion by fungi is 10%.
    As a comparison, compound B, N- (l-methoxycarbo5 nilethyl) -Y-ethoxyacetyl-2,6-dimethylaniline, was used, which under these conditions remained ineffective.
    Thus, the proposed fungicidal agent has an enhanced effect ..
    Table 1 of aqueous acetanilides and an additive selected from the group of: carrier, diluent and filler, characterized in that, in order to enhance the fungicidal effect, it contains as a derivative of acetanilide a compound of the general formula cc, cc, CH -bt 4 rf-f- 1 O a, c, Rrt - methyl, ethyl, chlorine or bromine;
    ten
    725542, Continued on. tags (and; R7 - hydrogen or methyl; Rg - methsgie or ethoxy, in an amount of 0.1 - 90 wt.%. Sources of information taken into account during the examination 1.Patent of France No. 2265727, cl. 07 C 103 / 4bu published 28.11.75. 2.Patent of Great Britain No. 1445387, class C 07 C 103/46, published state, 11.08.76. 3. Order I 2407098/05, class A 01 N 9/12, C 07 C 87/56, 30.09.76, according to which the decision was made to grant a patent (prototype),
    权利要求:
    Claims (1)
    [1]
    Claim
    R 3 and R +
    A fungicidal agent containing 40 active principles based on derivatives of acetanilides and an additive selected from the group: carrier, diluent and excipient, characterized in that, in order to enhance the 45 fungicidal action, it contains, as derivatives of acetanilide, a compound of the general formula Where
    - methyl, ethyl, chlorine or bromine;
    -a R 5 R 6 - independently from each other, hydrogen or methyl;
    - COOCH-j or COSCH 3 ;
    - hydrogen, methyl or methoxy;
    Rf is hydrogen or methyl; Rg methoxy or ethoxy, in an amount of 0.1 to 90 wt.%.
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    同族专利:
    公开号 | 公开日
    DE2812957A1|1978-10-12|
    FR2385687B1|1980-07-04|
    NL7803275A|1978-10-02|
    JPS53119836A|1978-10-19|
    GB1596343A|1981-08-26|
    AT356458B|1980-04-25|
    CA1121376A|1982-04-06|
    CH627343A5|1982-01-15|
    FR2385687A1|1978-10-27|
    LU79324A1|1978-11-03|
    IL54365D0|1978-06-15|
    AU514793B2|1981-02-26|
    AU3480378A|1979-10-11|
    JPS629105B2|1987-02-26|
    IT7821653D0|1978-03-24|
    SU725542A3|1980-03-30|
    BE865293A|1978-09-25|
    IL54365A|1981-07-31|
    ZA781698B|1979-03-28|
    ATA209778A|1979-09-15|
    IT1095492B|1985-08-10|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    JPS5028496B2|1972-02-02|1975-09-16|
    SE397191B|1972-10-13|1977-10-24|Ciba Geigy Ag|N- -N-HALOACETYL-2,6-DIALKYLANILINES FOR USE AS FUNGICIDE|
    JPS5119020B2|1973-02-16|1976-06-14|
    OA04979A|1974-04-09|1980-11-30|Ciba Geigy|New aniline derivatives useful as microbicidal agents and their preparation process.|
    CH623458A5|1975-09-30|1981-06-15|Ciba Geigy Ag|CH637368A5|1978-10-27|1983-07-29|Ciba Geigy Ag|ANILINE DERIVATIVES AND Pesticides Manufactured From Them.|
    CH639940A5|1978-12-05|1983-12-15|Ciba Geigy Ag|Substituted N-alkoxycarbonylethyl-N-acylanilines, microbicides containing them, and process for the preparation of the compounds|
    CH639643A5|1979-03-21|1983-11-30|Ciba Geigy Ag|Pesticides|
    FR2455574B1|1979-05-03|1983-10-21|Ciba Geigy Ag|
    CH643815A5|1979-10-26|1984-06-29|Ciba Geigy Ag|N-Acylated N-phenyl and N- derivatives having a microbicidal action|
    US4377587A|1980-07-25|1983-03-22|Ciba-Geigy Corporation|Arylamine derivatives and use thereof as microbicides|
    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    CH388577A|CH627343A5|1977-03-28|1977-03-28|Microbicide|
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