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    • 专利摘要:
    1,2,3-Thiadiazole-5-carboxylic acid amide derivatives of the formula <IMAGE> wherein R1, R2 and R3 have the meaning indicated in the specification. Preferably, R1 is methyl and R2 is acetyl, chloroacetyl, propionyl, valeryl, cinnamoyl, cyclohexylcarbonyl, dichlorophenoxyacetyl, benzoyl, halobenzoyl, dichlorobenzoyl or methylbenzoyl, and R3 is benzyl, halobenzyl, cyclohexyl, methyl-cyclohexyl or cyclohexylmethyl. The compounds have herbicidal, growth regulating, defoliating and fungicidal activity, although not all of these activities will be present in each of the compounds. The compounds are in addition highly selective against agriculturally valuable plants such as various grains, cotton, soybeans and plantation cultures.
    公开号:SU965355A3
    申请号:SU802903448
    申请日:1980-04-01
    公开日:1982-10-07
    发明作者:Крюгер Ханс-Рудольф；Арндт Фридрих；Баумерт Дитрих；Руш Райнхарт
    申请人:Шеринг Аг (Фирма)；
    IPC主号:
    专利说明:

    carboxyl chloride of the general formula N-C-CHs II II where R has the indicated meanings, is reacted with the carboxylic acid of the general formula R COOH in which R has the indicated meanings, in a polar solvent, in the presence of triethylamine. . Delivery is also achieved by the fact that compounds of the general form are obtained. (G), where R is cyclohexylmethyl; R-methyl, by the interaction of an amide 1,2,3-thiadiazole of 5-carboxylic acid of general formula N. C-CONH-R g / where R is cyclohexylmethyl, with propenyl ester of acetic acid in the presence of an acid catalyst,. The xapiaKTepHsSMTC compounds are remarkably effective land-herbicides and / or foliage-herbicidal drugs in relation to the weeds and in the case of germinated weeds, and are superior to known compounds that are similar in structure to the same spectrum of action. The action is partially systemic. Particularly advantageously amenable to the action of the compounds and di koltilnye monokotilnye weeds such as Digitalis, TrifoEium, PortuKaca Papavqr, Daucas, Kochia, GypsophiEa, Lactuca, -Souanum, Esch- hoCtzia, cheiranthus, PhaceEia, Euphorbia, Linum, ConvoBvuCus, Bras sica. Datura / Cichorium, JpomoSa, Setaria, Agrostis, Phytera, Avenium, Averio, Averio oa, Digitaria, Surezpdz, Poa und audere, Expenditure standards for weed control are approximately O ,, 5-5.0 kg of effective substance per hectare, - Selective control with 1Mk is possible, for example, the following crops of cereals, cotton , soybeans and gourds,. The proposed substances have the greatest effect if they are spread on the available weed shoots or before their germination by These cultures can also be sown several days after the spray, no,. The proposed compounds can also alter the natural development of the plants to the achievement of various properties required in agriculture or horticulture. However, not every compound causes such a regulating effect in each type of plant, regardless of the method and duration of its use or concentration. The proposed compounds can be applied to seeds, embryos before or after germination, on roots, stem, leaves, flowers, fruits, or other parts of plants. The management of natural growth can be observed visually by changing the size, shape, color, or structure of the treated plants or its parts ,. For example, the following changes in plant development caused by the proposed compounds may be named: an increase in leaves, a slowdown in vertical growth, a slowdown in the development of the ROOT, an impetus to the formation of buds or shoots, an intensification, the formation of dyes in a plant, defoliation, .. In addition, The proposed compounds are effective against various harmful fungi, for example Gattungeu Botrytis, Cercosroga, Erysiphe, HeEminthosporum, PiricuEaria, PEasmoparpa, Tieeetia, and others. Simultaneously with the regulation of plant growth, it is possible to combat atogennymi plant fungi, which is of particular technical significance, reaction of the reaction components ocsptsectvl out at 0-120 seconds, but is usually in the range from room temperature to the reflux boiling temperature of the corresponding reaction mixture. For the synthesis of new compounds, reagents are used in approximately equimolar amounts. Inert solvents are suitable for the reaction components. The choice of solvent or suspending agent depends on the use of appropriate acyl halides, acid acceptors or metal compounds. Esters (distilty, tetrahydrofuran and dioxane are used as solvents or suspending agents) ), aliphatic and aromatic hydrocarbons (petroleum zfir and cyclohexane, benzene, toluene and xylene), carbonyric acid nitriles (acetonitol, reel), etony (acetone)
    Suitable acid acceptors are organic bases, for example, triethylamine or Y, M-dimethylaniline, and pyridine bases or inorganic bases, such as oxides, hydroxides and carbonates of alkali and alkaline earth metals. Liquid bases, for example, pyridine, in, can simultaneously serve as a solvent.
    The new compounds obtained by the proposed method can be isolated from the reaction mixture by conventional methods, for example, by distilling off the used solvent under normal or reduced pressure or by precipitating with water.
    The new compounds are usually colorless, odorless crystalline crystals or colorless, odorless liquids that are strongly soluble in water, relatively soluble in aliphatic hydrocarbons, {petroleum ether and cyclohexane), well soluble in halogenated hydrocarbons (chloroform and carbon tetrachloride) , aromatic hydrocarbons (benzene, toluene, xylene), ethers (diethyl, tetrahydrofuran and dioxane), carboxylic acid nitriles (acetonitrile), ketones (acetone), alcohols (methanol and ethanol), am dach carboxylic acids (dimethylformamide), sulfoxides (dimethyl sulfoxide).
    Cyclohexane, acetonitrile and di-eopropyl ether are particularly suitable solvents for Recrystallization.
    The starting materials for the preparation of the new compounds are known substances or can be obtained by known methods.
    Example 1. (N-Acetyl-Y-diclohexylmethyl) -amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid.
    (N-Acethyl-N-cyclohexylmethyl) amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid in the amount of 16.8 g (0.07 mol) is suspended in 35 ml (0.32 mol) of propenyl ether acetic acid and mixed with 0.04 mp of concentrated sulfuric acid. Immediately thereafter, it is heated for 28 hours at reflux temperature, then the remaining oil is introduced into 50 MP of pentane for crystallization. Recrystallized from cyclohexane. The yield of 14.7 g (74.6% of theoretical). 7374 ° C (colorless crystals).
    PRI mme R 2. (L-Benzoyl-N-cyclohexylmethyl) -amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid.
    A solution of 23.9 g (0.1 mol) of cyclohexylmethylamide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid in
    200 ml of tetrahydrofuran are incubated for 2 hours with 2.4 g (0.1 mol) of sodium hydride at reflux temperature. Then at O-10 ° C, 14.06 g are added with cooling.
    5 (0,) benzoyl chloride. After a two-hour reaction, the solution is evaporated and the final residue is carefully mixed with water. Immediately after this, shake again.
    10 with ether.
    The ether extract, dried over sodium sulfate, is evaporated and the final crystals are recrystallized from isopropyl ether. Yield 13.0 g
    5 (° theoretical). Trl 89-91 ° C
    (colorless crystals).
    PRI me R 3. (N-Isobutyryl-Ncyclohexylmethyl) -amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid.
    20 4.7 ml (0.05 mol) of isobutyric
    50 ml of tetrahydrofuran acid is added together with 7.1 ml (0.05 mol) of triethylamine. At the temperature of reflux boil, 12.9 g are added dropwise.
    25 (0.05 mol) 4-methyl-1,2,3-thiadiazole 5- (N-cyclohexylmethyl) -carboximid chloride, dissolved in 100 ml of tetrahydrofuran. Immediately thereafter, it is heated for another 15 minutes at reflux temperature. After that it is cooled, the precipitate is filtered off and the organic phase is evaporated. The remaining oil is added to the ether and shaken repeatedly with water. Essential
    The 35 phase, dried over magnesium sulfate, is evaporated and the remaining oil is dried at 40 ° C with Et vacuum. The output of 11.0 g (71.2% of theoretical), 1,5291 (colorless oil).
    The following compounds can be prepared in a similar manner: (L-Benzoyl-Kbenzyl) 4-methyl-1,2,3-thiadiazole-5-carboxylic acid amide, 97 ° C; Sy-benzoyl-Y- (4-fluorobenzyl), amide-4-methyl-1,2,3-thiadiazol-5-kAE bonic acid, mp mp 143-1440G; K-benzoyl-K- (2-methylcyclohexyl) amide 4-methyl-1,2, 3-thiadiazole-5-carbrinoic acid, Trl 99-102 ° C; n-acetyl-N- (2-fluorobenzyl) -amide
     4-methyl-1., 2,3-thiadiazole-5-carboxylic acid, n1 ° 1.5627; N-acetyl-N- (4fluorobenzylT-4-methyl-1,2,3-thiadiazole-5-carboxylic acid amide, Pp 1.5625 y-acetyl-N- (4-chlorobenzyl) amide 4-methyl-1,2 , 3-thiadiazole-5-carboxylic acid, Trp 66-68 ° C; N- (4-chlorobenzyl) -Y-cyclohexylmethyl amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid, Tp I5-116 ° C; (N-npo60 pionyl-N-cyclohexylmethyl) -amide 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid, Tfl, 64-65 ° C; W- (4-ft, orbenzoyl) N -cyclohexylmethyl -amide 4-methyl1, 2,3-thiaviazole; 5-carboxylic acid, mp 110 111 ° C; (L-chloroacetyl-Micyclohexylmethyl) amd 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, mp 111-112 ° C; Gy- (3-chlorobenzoyl) - L-cyclohexylsylmethyl-amide 4-methyl-1,2,3-thiadiazole-5-cargoxylic acid, T (, d 95-97 C; K- {3-metshlbenzoyl) -N-cyclohexylmethyl-amide 4-methyl1, 2,3-thiadiazole -5-carboxylic acid, Tpd 73-74 Cf, L- (4-methylbenzoyl) -Ncyclohexylmethyl-4-methyl-1,2,3-thiadiazole-5-carboxylic acid amide, T, d 71-72C; (L-valeryl- N-cyclohexylmethyl) -amide-4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 4647C; N- (2,4-dichlorophenoxyacetyl) N-cyclohexylmethylJ-amide 4-methyl1, 2,3-tsadiazol5- carboxylic acid, Tr. 87-89 ° C; . (K-benzoyl-L-cyclohexyl) -amide 4-methyl-1,2,3-thiadiazole 5 -carboxylic. acids, T-PL 81-83C; (N-acetyl-N-cyclohexyl} -amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid, T "d 82-83 ° C; N- (2-chlorobenzoyl) -M-cyclohexylmathy-amide 4-methyl-1, 2,3-thiadiazole-5-carbonic acid., Tpd 5 3-5 5 C; (N-cyano-N-cyclohexylmethyl) -amide 4-methyl 1, 2, 3-thiadiazole-5-carboxylic acid , 1.5947; (N-cyclohexylcarbonyl-M-cyclohexylmethyl) -amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid, TPA 96-97 0; (N-cyclorexylmethyl-E-diclopropylcarbonyl) amide 4 -methyl-1,2, 3-thiadiazole-5.-carboxylic acid (nj) 1.5411; N-cyclohexylmethyl-N- (2 6-dichlorobenzoyl) amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid, Tpd 81-8Z C (N-cyclohexylmethyl-N-dichloroacetyl) -amide 4-methyl- 1,2,3-tig1 diazole-5-carboxylic acid, m.p. 84-86 ° C; (N-crotonoylM-cyclohexylmethyl) -amide 4-methyl1, 2, 3-thiadiazole-5-carboxylic acid, n2) ° 1.5478; N-cyclohexylmethyl- (2-furyl) -amide 4-methyl-1,2,3. -Thiadiazole-5-carboxylic acid. Tol 80-81 ° C; tN-cyclohexylmethylN- (2,4-dislsorbenzoyl) -amide 4-methyl1, 2, 3-thiadiazole-5-carboxylic acid, TPA 87-88 ° C; N-cyclohexylmethyl-Y (2-trifluoromethylbenzoyl) -amide 4-methyl 1,2, H-thiadiazole-5-carboxylic acid, mp 63-64 ° C; fN-cyclohexylmethylN- (2,6-dichloro-2-methylbenzoyl) -amide 4-1ethyl-1,2,3-thiadiazs-5-carboxylic K1 slot, Mp 76-77 ° C; N-cyclohexylmethyl-N- (3-trifluoromethylbenzoyl) aidide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, Trp 92-93 C; N-diclohexylmethyl-N- (3-furoyl) -amide 4-methyl-1, 2,3-thiadiazole-5-carboxylic
    acid, Mp 8b-88 ° C; tN-cyclohexylmethyl-N- (2,5-dichloroben zoyl) amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, TPd 67-69 C M-cyclohexylmethyl-N- {3, 5-dichlorobenzoyl ) 4-me1 amide; yl-1,2,3-thiadiazole-5-carboxylic acid, Tpd 67-69 ° C; L-cyclohexylmethyl-M- (2-phenoxy. Benzoyl) -amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, Tp 9193 C; Cm-cyclohexylmethyl-N-4-methyl-1, 2,3-thiadiazol-5-yl-carbrnyl) amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 64-67 ° C; N-diclohexylmethyl-L- (.3,4-dichlorobenzoyl) -amide 4-methyl-1,2,3-tadi
    azole-5-carboxylic acid, Trd 113114C; Cm-acetyl-L- (3-methylcyclohexyl) -amide 4-methyl-1,2, H-thiadiazole 5 -carboxylic acid, TPA .68-70 ° C. One of the original products for
    5 to obtain the proposed compounds. may be better, for example. as follows ..
    4g-Methyl-1,2,3-thiadiazol-5 -. (L-. Cyclohexylmethyl) -carboximid chloride.
    47.8 g (0.2 mol) of diclohexyl-4-methyl-1,2,3-carboxylic acid tilamide, dissolved in 100 ml of toluene, are extracted with 41.6 g (0.2 mol) of phosphorus pentachloride at. rooms-,
    5 o'clock and immediately thereafter heated to reflux. After this, the solution is evaporated and the remaining oil is mixed with cyclohexane. Re-crystallized from cyclohexane. The output of 49.0 g (77.5% of theoretical). Mpd 51-52 ° С (colorless crystals),.
    EXAMPLE 4 In a greenhouse, compounds (see Table 1) in the form of aqueous emulsions or suspensions are sprayed at a consumption rate of 5 kg of an effective substance per hectare in 600 liters of water per hectare per test plants.
    Q Sinapis (Si), Soeonuin (So), Beta
    vuRgaris (Be), Gossypium (Go), Hordeiim, (Ho), Zea mays (Ze), Loeium (Lo), Setaria (Se), in the plate before and after germination. Three days after treatment, the results are evaluated. At.
     This is accepted: O - no action; 1-2 - effect of regulating growth in the form of intense leaf color, slowing, slowing growth and decreasing or increasing leaves, slight development of the root; 3-4 - plants are not viable or they give uv. Table 1 shows the following substances:. :
    1. (M-Acetyl-K-cyclohexylmethyl) 5-amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid.
    2. (K-Benzoyl-L-cyclohexylmethyl) amide 4-methyl-1,2,3 thiadiazole-5-carboxylic acid.
    0 3. (K-Isobutyryl-N-cyclohexylmethyl) -amide 4-methyl-1,2; 3-thiadiazole 5-carboxylic acid.
    4. (N-Venzoyl-L-benzyl) -methyl 4-methyl-1, 2, 3-thiadiazole-5-carboxylic
    5 acids ..
    5. N-Nenzoyl-N- (4-fluorobenzyl) amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid.
    6, GM-Benzoyl-L- (2-methylcyclohexyl) -amide 4-methyl-1,2,3-ty diazole 5-carboxylic acid.
    7 M-Acetyl-H- (2-fluorobenzyl) amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid.
    8 and 9. tN-Acethyl-N- (4-chlorobenzylamide. 4-methyl-1,2,3-thiadiazole-5-carboxylic acid.
    10. (4-Chlorobenzoyl) -N-cyclohexymethyl-4-methyl-1,2,3-thiadiazole-5-carboxylic acid amide.
    11. (L-Propionyl-M-cyclohexylmethyl) -amide 4-methyl-1,2, 3-thiadiazole-5carboxylic acid.
    12.fN- (4-Fluorobenzoyl) -N-cyclohexylmethyl-4-methyl-1,2,3t amide of adiazol-5-carboxylic acid.
    13. {N-Chloroacetyl) -Y-cyclohexylmethyl-amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid.
    14.tw- (3-Chlorobenzoyl) -N-cyclohexylmethyl-4-methyl-1,2,3-thiadiazole-5-carboxylic acid amide.
    15. (3-J-methylbenzoyl) -N-cyclohexyl-methyl-4-methyl-1,2,3-thiadiazole-5-carboxylic acid amide.
    16. (4-Methylbenzoyl) -Y-cyclohexylmethyl-4-methyl-1,2,3-thiadiazole-5-carboxylic acid amide.
    17. (Y-Valeryl-Y-cyclohexylmethyl) -amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid.
    18. (2,4-Dichlorophenoxy-acetyl) -N-cyclohexylmethyl) -amide 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid.
    19. (N-Benzoyl-N-cyclohexyl) amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid.
    20 .. (N-Adethyl-N-cyclohexyl) amide 4-methyl-1,2, 3 thiadiazole-5-carboxylic acid.
    21. (2-Chlorobenzoyl) -N-cyclohexylmethyl - 4-methyl-1,2,3-thiadiazole-5-carboxylic acid amide.
    22. (N-Tsinamoyl-N-cyclohexylmethyl) -amide 4-methyl-1,2,3-thiadia of ol 5-carboxylic acid.
    23. (N-Cyclohexylcarbonyl-N-cyclohexylmethyl) -amide 4-methyl-1,2,3tIc1Diazl-5-carboxylic acid.
    24. (N-Cyclohexylmethyl-N-cyclopropylcarbonyl) -amide 4-methyl-1,2,3thiadiag5-carboxylic acid.
    25. M-Cyclohexylmethyl-H- (2,6 dichlorobenzoyl) -amide 4-methyl-1,2,35 thiadiazole-5-carboxylic acid.
    26, (N-Cyclohexylmethyl: - N-dichloroacetyl) -amide 4-methyl-1,2, 3-thiadiazole 5-carboxylic acid.
    27. (L-Crotonoyl-L-cyclohexyl 10 methyl) -amide 4-methyl-1,2, 3-thiadiazole 5-carboxylic acid.
    28. G Y-Cyclohexylmethyl-Y- (2-furoyl) -amide 4-methyl-1,2-, 3-his1 diazole 5 -carboxylic acid.
    5 29. n-Cyclohexylmethyl-N- (2,4dichlorobenzoyl) -amide 4-L1ethyl-1,2,3thiadiazole-5-carboxylic acid,
    30. n-Cyclohexylmethyl-M- (2 trifluoromethylbenzoyl) -amide 4-methyl 0 1,2, 3-thiadiazole-5-carboxylic acid.
    31. C-Cyclohexylmethyl-M- (3,6 dichloro-2-methoxybenzoyl) -amide 4-.
    5 methyl-1,2,3-thiadiazole-5-: carboxylic acid.
    32. G1-Cyclohexylmethyl-M- (3-trifluoromethylbenzoyl) -amide 4-letyl-1,
    2, 3-thiadiazole-5-carboxylic acid.
    33. n-Cyclohexylmethyl-K- (3-fu
    0 royl) -amide 4-methyl-1,2, 3-thiadiazole5-carboxylic acid.
    34 tN-Cyclohexylmethyl -Y- (2,5dichlorobenzoyl) -amide 4-methyl-1,2,3-5 thiadiazole-5-carboxylic acid.
    35. N-Cyclohexylmethyl-K- (3,5dichdorbenzoyl) -amide 4-methyl 1, 2, 3-thiadiazole-5-carboxylic acid.
    36. s-Cyclohexylmethyl-H- (20 phenoxybenzoyl) -amide 4-methyl-1,2,3-tiazol-5-carboxylic acid.
    37. n-Cyclohexylmethyl-H- (4methyl-1, 2,3-thiadiazol-5-yl-carbo5-nyl) -amide 4-methyl-1,2, 3-thiadiazole-5 carboxylic acid.
    38. n-Cyclohexylmethyl-L- (3,4 dichlorobenzoyl) -amide 4-methyl-5-carboxylic acid.
    0
    39.1 | Y-Acetyl-Y- (3-methylcyclohexyl)} -amide 4-methyl-1,2, 3-sischiazol5-carboxylic acid.
    40. Unprocessed samples.
    Table 1
    Continued table. one
    Continued table. one
    Note. 40 N P and measures 5. In the greenhouse, the above plants are treated before germinating with the proposed means with a consumable Hopf "3ft 1 kg of effective substance per hectare. For application, a suspension is applied with 500 ml of water per hectare evenly over the ground. The results (Table 2) show that the proposed remedy destroys the most important weeds, while the important agricultural soybean bo (remains intact. The proposed remedy is {N-acetylM-cyclohexylmethyl) -amide 4-methyl-1,2, . Z-thiadiazole-5-carboxylic acid. Complete destruction; 10 - no damage. Untreated; V - before the start of r after sprouting.
    33
    I am a N o w a l o l w w w imer 6. In a greenhouse, cucumbers are treated with a consumable compound of 0.3, before sprouting; 1 and 3 kg per hectare. For this purpose, an effective substance is used in the form of a 20% emulsion concentrate in the form of an aqueous emulsion with a liquid flow rate of 500 liters of broth for a rabbi% per hectare. Three weeks after treatment, the effect of regulating plant growth is established by measuring the length and width of the first green leaf (Table 3). Measurement results are consistent with results obtained with untreated samples. As can be seen from the measurement results, the treatment with the proposed compound causes a strong increase in the leaves. In addition, the treated plants have a more intense, green color. Table 3 (N-Acetyl-Ncyclohexyl-IO / 107 methyl) -amide
    100 122lD9P ®4 6 W. 25E5521 jyo2 25B22 E1 Yorazhёna specimens of samples The substances are made up in the form of a 20% wettable powder. 1. (N-Benzoyl-N-cyclohe1 silmethyl) - 40-amide 4-methyl-1,2,3-thiad (azole5-carboxylic acid. - 2 "(K-Benzoyl-N-benzyl) -amide 4-methyl- 1,2, 3-thiadiazole-5-carboxylic acid. 3. L-Benzonl-M- (2-methylcyclohexyl) -amide 4-methyl-1,2,3-thiadiazole 5-carboxylic acid. 4. L-Acetyl- L-(2-fluorobenzyl) amide 4-methyl-1,2,3-bis-1-diazole-5-carboxylic acid 5. S-Acetyl-L- (4-fluorobenzyl) -amide 4-methyl-1,2, 3-thiadiazod -5-carboxylic acid. 6.SY-Acetyl-L- (4-chlorobenzyl) - 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid amide 7. (N-Chloroacetyl-N-cyclohexylmethyl) -amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid. 8. (N-Valeryl-Y-cyclohexylmethyl) -amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid, 9. (2-Chlorobenzoyl) -N-cyclohexylmethyl-amide 4-methyl-1,2,3-thiadiazole - 5-carboxylic acid. Effects of efficacy 5 Continued Table 3 Example: Efficacy of p, preventive p6paj6oTKH leaves against a plasma pair of viticola on a vine in a greenhouse. Young vines with about 3-8 leaves are sprayed with a drop of a pointer. after concentration, after dispersion of the spray layer, the back side of the sheet is sprayed with water suspension of the fungus spores ( and approximately 20,000 to 1 ml), and immediately incubated in a greenhouse at 22–24 ° C in an atmosphere, possibly with water saturated with vapors. From the second day, the humidity of the air to 3-4 days is maintained normal (30-70% of saturation) and then one day is kept on the water surface. Immediately thereafter, the percentage of the spots damaged by the fungi is evaluated on each sheet and the average value is calculated depending on the treatment of the fungicidal action (Table 4). . l 10. (K-Zinnamoyl-M-cyclohexylyl) -amide 4- "ethyl-1,2,3-thiadiazolar of a carboxylic acid,. 11, (N-Cyclohexylmethyl-Y-cyclopylcarbonyl) -amide 4-methyl-1,2,3-diazole-5-carboxylic acid, 12, N-cyclohexylmethyl-Y- (2,6orbenzoyl) -amide 4-methyl-1,2 3dazole-5-carboxylic acid,. 1 T a l i c a 4 Continued table. 4 Percentage efficiency Compound after treatment with active substance, wt.% 100-Defeat in an image of an LLP in "mv1. In" vivv "-" eeeieeeeeeee ee J Defeat in neurosis. Determination in vii 20%. Substances make up in vii 20%. I wetting powder. 1. (n-Acetyl-L-cyclohexylmethyl) amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid. 2. (N-Benzoyl-L-cyclohexylmethyl amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid. 3. (k-Isobutyryl-N-cyclohexylmethyl) -amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid. 4. (L-Propionyl C-cyclohexylmethyl) -amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. 5. (s-Chloradethyl-S-cyclohexylmethyl) -amide 4-methyl -1,2,3-thiadiazole 5-carboxylic acid. B. (S-Valeryl-L-cyclohexylmethyl) -amide 4-methyl-1,2, 3-thiadiazole 5-carboxylic acid. 7. tN- (2, -4 -Dichlorophenoxyacetyl) H-cyclohexylmethyl-amide. 4-methyl100-Defeat obra, 100 —the expression of the throat of the substance. Substances are in the form of a 20% solution. of powdered powder. 1. (H-Benzoyl-H-diclohexylmethyl) -amide 4-methyl-1,2, H-thiadiazole-5-carboxylic acid 2. (L-Benzoyl-H-benzyl) -amide 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid 3. n-Benzoyl-M- {2-methylcyclohexyl) -amide 4-methyl-1,2, 3-thiadiazole 5-carboxylic acid. 4. (N-gHloroacetyl-K-cyclohexylme trl) -amide 4-methyl-1,2,3-thiadiazole5 carboxylic acid. Table Example. The effectiveness of prophylactic treatment of leaves against Erysiphe Cichoracearum on pumpkin plants in a greenhouse. Pumpkin plants are sprayed with the indicated concentrations of effective substances and after drying the applied layer with the dried spore flour of Erysiphe Cichoracearxira sprayed on it, they are incubated at 24 ° C. After a week, the affected surfaces were meleded as a percentage of the total leaf surface (Table 5). The fungicidal effect is calculated according to the formulas of the azts, now the efficiency samples ... i hr CHT 1,2, W-thiadiazole-5-carboxylic acid. 8, (N-Cyclohexylmethyl-N-cyclopropylcarbonyl) -amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid. Example 9. Leaf treatment efficiency against PiricuQaria oryzae in rice seedlings in a greenhouse. Young rice plants are sprayed with drops of the effective substance at the indicated concentration. B. After the sprayed layer has dried, the treated plants, as well as untreated control plants, are inoculated by spraying with cus-. Spore's pensions (approximately 200,000 / ml) of the pathogen of deciduous trees are PiriCaria oryzae and wet incubated at 25-27 ° C in a greenhouse. After 5 days, the percentage of hardwood lesion is determined. From this number of injuries, the fungicidal activity is calculated according to the formula of 6 times the fraction of the effectiveness of the cells. Continuation of the table., Percentage of effectiveness. The compound after treatment with the active substance, wt.%
    Table
    The percentage of effectiveness after treatment of 0.1 wt.% The active substance
    75
    90
    75
    90 100 Survival of about 2 AZNDs 100 - PREVENTION of no samples 6
    Compounds are designed as
    (M-acetyl-H-cyclohexylmethyl) -amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid
    Methoxyethyl mercury silicate (for comparison)
    Example 11. Treatment efficiency of wheat seeds against TiEEetia caries. .
    Wheat seeds are mixed with TIE etia caries spores, and they are added in an amount of 3 g per 1 kg of grain. Untreated or processed as indicated in Table 8, grains with a shaggy tip are put in. Substances are drawn up in the form of 20%
    Compound
    (N-Chloroacetyl-L-cyclohexyl) amide 4-methyl-1,2,3-thiadiazole 5 -car6anoic acid
    (N-Valeryl-Y-cyclohexylmethyl) amide 4-methyl-1,2,3-thiadiazole 5-carboxylic acid
    Note. The plants treatment did not hurt.
    I'll try it on. Eff «efficacy of processing seeds nchmen against HePminthosporun spec.
    Barley seeds with natural piggy Her minthosporum spec / untreated or treated as indicated in Table 7 are sown in a pot with soil and kept at 16 ° C to
    0 germination. After germination, shoots are illuminated with artificial light every day for 12 hours. After 5 weeks, all germinated plants, as well as plants affected by fungi. are counting. Fungicidal action
    5 was calculated by the formula
    20% wettable powder. T a b l and c a 7
    70
    100
    86
    96
    70
    Petri's cups with clay and clay: cubed at 12 ° С for 3 days. Immediately after this grain
     Take out and Petri dishes with the remaining spores are incubated further at about 12 ° C. After 10 days, spores are examined for germination. Fungicidal efficacy of tallying,
    45 whether by the formula
    Percentage efficiency with 20 g effective substance / 100 kg seeds
    75
    75 YuO-Percentage of the Poeoustats 1 of the Ob-educated ObaTs .. „„ ,. -55515t pr5Y5ta555 untreated samples of the effectiveness of the effectiveness of wetting powder. Table 8
    N- (2,4-Dichlarphenoxyacetyl) N-cyclohexylmethyl-4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid amide
    H -. {2-Chlorobenz9yl) -N-cyclohexylmethyl-4-methyl-1,2,3-thiadiazole-5-carbonic acid acid amide
    (M-Zinnamoyl-N-cyclohexylmethyl) -amide 4-methyl-1,2,3-thiadiazole-5-carbonose acid
    (N-Cyclohexylcarbonyl-N-cyclohexylmethyl) -4-methyl amide, 2, 3-thiadiazole-5-carboxylic acid
    (N-Cyclohexylmethyl-N-cyclo-11-propylcarbonyl) -amide 4-methyl 1, 2, 3-thiadiazole-3-carboxylic acid Example 12. The plants of the cotton plant are sprayed with the proposed effective substances in the form of an aqueous emulsion or suspension with expendable a norm of 500 l of water per hectare Compound (L-Acetyl-K-cyclohexyl amide 4-methyl-1,2, Z-thiadi of 5-carboxylic acid.
    Three -n-butyltrithiophosphate (for comparison)
    Example 13. Cotton plants at the deployment stage of a 5-6 leaf are sprayed with the proposed effective substances in the form of an aqueous emulsion or suspension with a consumption rate of 0.5 kg per 500 l of water
    (K-Chloroacetyl) -amide 4-methyl1,2, 3-3-thiadiazole-5-carboxylic acid
    (N-Valeryl-N-cyclohexylmethyl) 4-methyl-1,2,3-thiadiazole 5-carboxylic acid amide
    (N-Ieobutyryl-Y-cyclohexylmethyl-amide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid
    Continued table. 8 I
    75
    84
    80
    82
    90
    0.5
    65.4
    per hectare (repeat 4 times). The counting of fallen leaves 14 days after application of the layer is given as a percentage of all leaves available at the time of treatment (Table 10).
    权利要求:
    Claims (3)
    [1]
    Table 10 (repetition 4 paaia), Counting of fallen leaves 9 days after, the application of the effective substance is carried out as a percentage change of all initially available leaves / as indicated in table 9. Table 9 I Contents, Percentage L kg / ha of defoliation) 0, 5 76.9 Claim 1. Investigation method for amide derivatives 1,2, З-thiadiazole-5-carboxylic acid of general formula I, C c-CON-COR -CON A “S / 4l where cyclohexyl, methylcyclohexyl, cyclohexylmethyl, benzyl, fluorobenenl, chlorobenzyl R is alkyl with 1-4 carbon atoms, cyclopropyl, cyclohexyl, propenyl, styryl, chlorine methyl, dichloromethyl, dichlorophenoxymethyl, phenyl methylphenyl, phenoxyphenylphenyphoxyphenylphenylphenylphenylphenylene, , trifluoromethylphenyl, chlorophenyl, dichlorophenyl, methoxy dichlorophenyl, furyl, 4-methyl 1,2, 3-thiadiazol-5-yl, consisting In that the alkali metal amide of the general formula is HCl-Nl N c-c-N® R B® / where K has the specified Zygcheni; B is an alkaline metal, which is reacted with an acyl halide of the general formula R -CO-X, where the R has the indicated values, in a polar solvent. . .
    [2]
    2. A process for the preparation of amide derivatives of 1,2, 3-thiadiazole-5-carboxylic acids of the general formula I N-C-CGH II II N C-CGN-COR / .A where R is cyclo-hexyl ,. methylcyclohexyl, cyclohexylmethyl, benzyl, benzyl FCS, hlorbenR - alkyl having 1-4 carbon atoms, cyclopropyl, cyclohexyl, propenyl, styryl, chloromethyl, dichloromethyl, dichlorophenoxymethyl, phenyl, methylphenyl, phenoxyphenyl, fluorophenyl, trifluoromethylphenyl, chlorophenyl, dichlorophenyl, metoksidihlorfenil, furyl, 4-methyl-1,2, 3-thiadiazol-5-yl, ... consisting in that 1,2,3-thiadiazole-5-carboximide chloride of the general formula ill, N is C NR "/ I, S., its where R has the indicated meanings, is reacted with a carboxylic acid of the general formula R CO-OH in a polar growth medium Oritel in the presence of triethylamine.
    [3]
    3. A process for the preparation of 1,2,3-thiadiazole-5-carboxylic acid amide derivatives of the general formula I, N-C-CH,. N C-CON-dOR N / A where R is cyclohexylmethyl; R is methyl, consisting of 1,2,3-thiadiazole-5-carboxylic acid amide of the general formula AND N-HC-CHj N C-COTiH-B where R is cyclohexylmethyl, is reacted with propenyl ester of acetic acid in the presence of an acid catalyst. Sources of information taken into account in the examination 1. Weigand Hilgetag. Experimental methods in organic chemistry. M., Himi, 1968, p. 453.
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    同族专利:
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    IT8021094D0|1980-04-01|
    AT367603B|1982-07-26|
    ZA802033B|1981-04-29|
    BR8001999A|1980-11-25|
    HU185216B|1984-12-28|
    NL8001477A|1980-10-07|
    IT1148809B|1986-12-03|
    LU82326A1|1980-07-02|
    US4314839A|1982-02-09|
    BG32418A3|1982-07-15|
    IL59737A|1984-03-30|
    IL59737D0|1980-06-30|
    IE800680L|1980-10-05|
    AU5715280A|1980-10-09|
    DE2913977A1|1980-10-23|
    ES490069A0|1980-12-01|
    FR2453165B1|1983-06-10|
    BG32415A3|1982-07-15|
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    GR66675B|1981-04-08|
    BG32414A3|1982-07-15|
    CA1142945A|1983-03-15|
    ATA180780A|1981-12-15|
    IE49980B1|1986-01-22|
    AR223705A1|1981-09-15|
    JPS55133368A|1980-10-17|
    CS220326B2|1983-03-25|
    AU535236B2|1984-03-08|
    GB2047695B|1983-04-20|
    GB2047695A|1980-12-03|
    PL223230A1|1981-02-13|
    引用文献:
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    DE2728523C2|1977-06-23|1986-02-27|Schering AG, 1000 Berlin und 4709 Bergkamen|4-Methyl-1,2,3-thiadiazole-5-carboxylic acid amide, agents having a herbicidal and growth-regulating action, containing this compound and a process for its preparation|
    US4163784A|1978-03-09|1979-08-07|Pfizer Inc.|Heterocyclylcarbonyl derivatives of urea, agents for dissolution of gallstones|DE3030736A1|1980-08-14|1982-03-25|Basf Ag, 6700 Ludwigshafen|N-DISUBSTITUTED ANILINE DERIVATIVES, THEIR PRODUCTION, THEIR USE AS MICROBICIDES AND AGENTS THEREFOR|
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    EP0976326B1|1998-07-30|2003-05-02|Nihon Nohyaku Co., Ltd.|Fungicidal composition containing a 1,2,3-tiadiazole derivative and its use|
    KR100700964B1|2000-03-15|2007-03-28|니혼노야쿠가부시키가이샤|Fungicidal and insecticidal compositions and method for using the same|
    AR056882A1|2006-02-01|2007-10-31|Bayer Cropscience Sa|DERIVATIVES OF THE FUNGICIDE N- CICLOALQUIL- BENCIL- AMIDA|
    CN101250168B|2008-03-28|2011-12-14|南开大学|Thiadiazoles imine derivative as well as synthesis and uses thereof|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    DE19792913977|DE2913977A1|1979-04-05|1979-04-05|1,2,3-THIADIAZOLE-5-CARBONIC ACID AMIDE DERIVATIVES, METHOD FOR PRODUCING THESE COMPOUNDS, AND THEIR CONTAINING AGENTS WITH HERBICIDES, GROWTH REGULATIVE AND DEBELIFIERING AND FUNGICIDAL EFFECT|
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