• 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:
    1500581 Substituted amides CIBA-GEIGY AG 8 April 1975 [9 April 1974 14 March 1975] 14380/75 Heading C2C The invention comprises compounds of the Formula I wherein R 1 represents a halogen atom or a C 1 to C 4 alkyl or alkoxy group R 2 and R 7 independently represent hydrogen or halogen or a C 1 to C 3 alkyl or a C 1 to C 4 alkoxy group and R 8 represents hydrogen or methyl and the total number of carbon atoms in the substituent groups R 1 , R 2 , R 7 and R 8 on the phenyl ring does not exceed 8; X represents the group -CH 2 - or -CH(CH 3 )-; R 3 represents a group of formula -COOR<SP>1</SP> or -CON(R<SP>11</SP>)(R<SP>111</SP>) (wherein each of R<SP>1</SP>, R<SP>11</SP> and R<SP>111</SP> independently represents hydrogen, methyl or ethyl; Y represents a group of formula (wherein Hal represents a halide ion) or (b) -OR 4 or (c) -SR 4 (wherein R 4 represents a C 1 to C 6 alkyl, a C 3 to C 6 alkenyl or alkynyl, optionally substituted by halogen or R 4 represents benzyl or phenyl optionally substituted by halogen or C 1 to C 4 alkyl or (d) (wherein R 5 and R 6 independently represent C 1 to C 4 alkyl). The compounds of Formula I are used as fungicides and compositions for such use are also described. The compounds of Formula I wherein Y represents OR 4 or SR 4 may be prepared by acylating a compound of formula with a compound of formula (wherein R 4 is as defined above and Hal<SP>1</SP> represents a halogen atom) respectively. The compounds of formula wherein Y represents SR 4 may be prepared by acylating a compound of formula wherein R 2 represents halogen, or C 1 to C 4 alkyl or alkoxy R 2 represents hydrogen, halogen or C 1 to C 3 alkyl and X represents -CH 2 or with a compound of formula Hal-COCH 2 SR 4 wherein R 4 represents C 1 to C 6 alkyl and Hal represents halogen.
    公开号:SU730268A3
    申请号:SU752124200
    申请日:1975-04-09
    公开日:1980-04-25
    发明作者:Хубеле Адольф
    申请人:Циба-Гейги Аг (Фира)；
    IPC主号:
    专利说明:

    (54) FUNCTIONAL MEANS
    one
    This invention relates to chemical plant protection products, specifically fungicidal agents based on acetanilide derivatives.
    The known trade preparations possessing fungicidal properties are ethylene bis-dithiocarbamate manganese (maneb), N-trichloromethylthiophthalimide (phthalan) 1, However, the known drugs with low concentrations of active substances have insufficient activity.
    In addition, it is known that N- (l-ethoxycarbonylethyl) -H- (a.pcanryl) -2-methyl-4-chloroaniline derivatives exhibit herbicidal properties 2.
    Chemically similar to the proposed compounds and ts11 and having fungicidal properties are known fungicidal agents based on N- (1-methoxycarbonylethyl) -N- (halomethylcarbonyl) -2,6-methylaniline and conventional additives 3, However, at low doses, the compound has insufficient fungicidal activity.
    The aim of the invention is to find new fungicidal agents based on acetanilide derivatives having a high activity.
    This goal is achieved by using an agent containing acetanilide derivatives of the general formula
    Sh
    15
    where R "is alkyl ;, - C ,, allyl, quinil, unsubstituted or substituted benzyl by chlorine,
    20
    moreover, the content of the active substance in the medium is 0.01- 90 wt.%.
    Forms of application of the usual. Solutions, wetting powders, granules, emulsions. They are prepared by conventional methods, used in the manufacture of preparative pesticides.
    The method of obtaining compounds of this formula is based on the acylation of the correspondingly substituted aniline. EXAMPLE 1 Preparation of N- (1-methoxycarbonylethyl) -N-methoxy acetyl 2, 3-dimethyl-6-ethylaniline. IOQ g2,3-dimethyl-b-ethylaniline, 223 g of 2-bromopropionic acid methyl ester and 84 g of NaHCO3 are stirred for 17 hours at 140 ° C, then filled, diluted with 300 ml of water, and extracted with diethyl ether. The extract is washed with a small amount of water, dried over sodium sulfate, filtered and the ether is evaporated. After distilling off the excess methyl ester of 2g-bromopropionic RI dys, j CH-COO with c-scgacid, the crude product is distilled under a high vacuum, mp. 88 800С / 0, 04 mm Hg. Art. 11 g of the ester obtained, 6.5 g of methoxyacetyl chloride, 2 ml of dimethylformide and 250 ml of absolute toluene are stirred for 3 hours at room temperature and boiled for 1 hour under reflux. After evaporation of the solvent, the crude product is distilled in vacuum, i.p. 126 - 132 ° C / 0.08 mm Hg. Art. The remaining compounds listed in Table. 1, 2 and 3 are prepared in a similar manner. Table 1
    Continued table. one
    B, f
    - CH-COOCHj
    table 2
    CHjTable
    ON,
    Example 2. Action against Phytophthora infestans on tomatoes.
    A. Kurative-action. After three weeks of cultivation, the sprouts of tomato varieties Roter Gnom are sprayed with a suspension of fungus zoospores and commemorated into a cabin with a temperature of 18–20 ° C and moisture-saturated air; A break in moisture after 24 hours. After drying the plants, 5 of them each are sprayed with a spray solution containing the active principle concentration of 0.06%. After drying the sprayed plants, they are again placed in a cabin with moist air for 4 days. The number and magnitude of the typical spots on the leaves by this time is a measure of the effectiveness of the test substances.
    B. Priventive Systemische-action. The active principle in the form of a spray solution with a concentration of 0.006% based on the volume of the soil is applied to the soil surface under every 5 Rpter Gnom tomato plants of three weeks old, planted in mountaineers. After three days, the underside of the leaves of the plants is sprayed with a suspension of zoospores of Phytophthora Infestans. Then the plants are kept for 5 days in a cabin with saturated moisture with air at 18-20 ° C. The typical spots on the leaves formed by this time are used to evaluate the effectiveness of the test substances. Score action score:
    0– lesion 0–5%,
    1 lesion of 5-20%
    five
    2 - defeat 20-50%,
    3 is the same defeat as in
    control experience - not tested. The results are shown in Table. four.
    0
    Table 4
    2 1
    1 O 1 O 2 1 1 1
    2 About About About
    about
    note j. Compound II Example 3. Effect against Plasmopara viticola on grapes. A. Residual-preventive action. In the greenhouse grown cuttings grapes varieties Chasselas. By the time of the formation of the tenth leaf, three plants are sprayed with a spray solution containing the active principle (O concentration, 02%). After drying the sprayed plants, infection is applied to the underside of their leaves in the form of a fungal spore suspension. Then put the plants for 8 days in a humid chamber. By this time, distinct disease symptoms appear compared to control plants. The number and size of lesions serve as a criterion for assessing the effectiveness of the test substances.
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    2 O O
    about. Ltd
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    Continued table. four
    O 1 2 O 2 1 1 O
    1 1 1 1
    one
    3
    Compound 1-Maneb,
    CNH-co-CO2H-CHjCl.
    15 16 17 18 20 21 24 26 B, Kurative-action. The cuttings of Chasselas grapes are grown in the greenhouse and, at the stage of formation of the tenth leaf, infect the lower side of their leaves with a suspension of Plasmopara viticola spore. After 24 hours of stay of these plants in a humid chamber, three sections are sprayed with a spray solution containing the active principle in a concentration of 0.006%. After this, the plants are kept in a humid chamber for 7 days. By this time, symptoms of the disease appear compared to control plants. The number and size of lesions on treated plants serve as a criterion for assessing the effectiveness of deist-. VIA is testing 1st substances. The results are shown in Table. 5. Table 5
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    2 2 1 2 2 3 О О О О About
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    Note III - known compound, 1 and 11, see table. four,
    Example 4. Action against Pythium Debaryanum on sugar beet. .
    Fungi grown on sterile oat grains are introduced into a mixture of earth and sand. Infected land is poured out in flower pots.
    1 About About About
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    1 1 о о о 1
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    ABOUT
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    1 3 3 3
    ki, where sugar beet seeds are then sown. Immediately after the shoot, the tested preparations are poured onto the ground in the form of aqueous suspensions (0.002% of the active principle based on the volume of the ground). The results are shown in Table. 6
    Bromine table; R is hydrogen; Rj is hydrogen; Y is SRg, where Rg is alkyl 14.03.75 with R4 is alkyl Q-Cj, chlorine, bromine; Rg is methyl; Y - OR “, where R is alkyl, allyl, alkynyl Cj-C, unsubstituted or substituted with benzyl chlorine. Sources of information taken into account during the examination 1. Melnikov N.N. Chemistry and pesticide technology. M., Chemistry, 1974, p. 358, 406. 2. US Patent 3598859, cl. 260-471, publ. 08.08.71. 3. German patent W 2212268, cl. C 07 C 103/48, off 08/15/74 (prototype).
    权利要求:
    Claims (1)
    [1]
    Fungicidal agent containing
    acetanilide derivatives as an active substance, as well as an additive selected from the group of diluent, dispersant, characterized in that, in order to enhance the fungicidal activity, it contains a compound of the general formula as an acetanilide derivative
    CH-1 I
    ^ .СН-СООСНз ^ е-енг-х,
    Kg 0
    where Ed is methyl, halogen;
    - hydrogen, alkyl With < -C 2 , chlorine, bromine, iodine;
    - hydrogen, alkyl C £ -C 2 , chlorine, bromine;
    - hydrogen or methyl;
    At 0 K or ZK 3 3 where cd -
    alkyl C £ , allyl, alkynyl Cd — C ^, benzyl unsubstituted or substituted by chlorine,
    moreover, the content of the active substance is 0.01-90 wt.%.
    Priorities by featured;
    04/09/74 at K { - methyl, halogen;
    - hydrogen, alkyl With <- <" 2 , chlorine,
    17
    730268
    18
    bromine; Η, is hydrogen; K 5 is hydrogen;
    Υ - 8K 3, where R a - alkyl, C l -C 4;
    14.03.75 at K d - alkyl C4-C 5 , chlorine, bromine; K5 is methyl; Υ is OH where K & is alkyl C4-Cd, allyl, alkynyl C ^ -Cd, benzyl unsubstituted or substituted by chlorine.
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    CH499574A|CH592410A5|1974-04-09|1974-04-09|n-Substd. acetanilides - microbicides useful for treating phytopathogenic fungi, prepd. by acylation of substd. anilines|
    CH325975A|CH608690A5|1975-03-14|1975-03-14|Microbicidal composition|
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