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    • 专利摘要:
    The invention provides thiazole derivatives of general formula I; <CHEM> or an acid-addition salt or metal salt complex thereof, in which R represents an optionally substituted aryl group; R<1> represents a hydrogen atom or an optionally substituted alkyl, alkenyl or alkynyl group; R<2> represents a hydrogen or halogen atom or an alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, hydroxyl, cyano, nitro, amino, alkylamino, dialkylamino or morpholine group; X represents an oxygen or sulphur atom, a carbonyl group or a group -CR<4>R<5>- where R<4> and R<5> independently represent a hydrogen atom or an alkoxy group; Y represents an oxygen or sulphur atom; n represents an integer from 0 to 6; m is 0 or 1; and Z represents a phenyl group; processes for their preparation; compositions containing such compounds and their use as fungicides.
    公开号:SU1579458A3
    申请号:SU884355953
    申请日:1988-06-23
    公开日:1990-07-15
    发明作者:Роберт Хай Вильсон Джон；Хаддок Эрнест
    申请人:Шелл Интернэшнл Рисерч Маатсхаппий Б.В. (Фирма)；
    IPC主号:
    专利说明:

    The invention relates to a method for producing new chemical compounds.
    namely, thiazole derivatives, which have fungicide properties, and can be used in agriculture for controlling fungal diseases of cultivated plants.
    1-bromo-2- (2,4, b-trichlorophenoxy) ethane (20.0 g, 0.066 mol), triethylamine (6.7 g, 0.066 mol) and propylamine
    The purpose of the invention is to obtain new (3.9 g, 0.066 mol) in ethanol (500 ml)
    heated overnight. After udaamides of heterocyclic acids, which have an increased fungicidal activity against a number of fungal diseases of cultivated plants.
    Example 1. A. Preparation of methyl-JQ is boiled over, MgSO4. After evaporation of the thiazole-5-carboxylate; the solvent remains an oil, which
    Methyl 2-aminothiazole-5-carboxylate (79 g, 0.5 mol) was introduced into a boiling solution of nitrate amyl (117.0 g, 1.0 mol) in dioxane 1l for 2 hours. from the eluent forms N-nponnn-N-2- (2). After heating with refluxing-4,6-trichlorophenoxy) ethylamine as a nickname for another half hour, the solvent is distilled off under reduced pressure and the residual product is distilled off with water, steam . The result is boxed amide.
    This oil, which with stirring of Thiazole-5-carboxylic acid (4.8 g), with petroleum ether, gives the desired product as a white solid (32.0 g), mp. 68 ° C.
    dissolving the solvent by evaporation, the residual product is dissolved in ether, washed with water and then evaporated over silica gel using chloroform as
    oils (12.6 g).
    D. Preparation of N-nponmi-N- 2- (2,4, 6-trichlorophenoxy) ethyl-thiazol-5-kap0, 037 mol), obtained in B, is heated under reflux with an excess of thionyl chloride (100 ml) per teB The preparation of thiazole-5-carboxylic 25 for 2 h is cooled, and the excess chloro-acid of thionyl is removed in vacuo. Os.
    A solution of sodium oxide hydrate (6.3 g), the product is suspended in dry water (100 ml) and introduced into a solution of methiridine (30 ml) and cooled in ice of thiazole-5-carboxylate (15.0 g bath for 10 minutes. A solution of 0.1 mol), obtained in A, in ethanol 30 M-propyl-M-2- (2,4,6-trichlorophenoxy) (100 ml) s After 10 minutes, ethanol ethylamine (10 , 7 g, 0.038 mol), is half distilled under reduced pressure, and the residual product is acidified with hydrochloric acid to a pH value of 1. As a result, the thiazole-5-carboxylic pyridine is removed by evaporation, and the residue is white solid. the substances the exact product is dissolved in chlorofor- (12.1 g), so pl. 218 C.
    C. Preparation of L-propyl H-2- (2,4, 6-trichlorophenoxy), ethylamine.
    A solution of sodium hydroxide (7.8 tel is removed. As a result, 0.195 mol) in water (20 ml) is added to a light brown oil, which is a clear solution of 2,4,6-trichlorophenol (38.0 g, 0.192 ml). mol) in ethanol (200 ml). Then 1,2-dibromoethane (47 g,
    0.25 mol) and the resulting mixture is heated to give the desired reflux over the course of the product as a white solid. After cooling, the solid is filtered and the filtrate is concentrated under reduced pressure. Ether is added to the residue, and then the solution is washed with a dilute solution of sodium hydroxide, ri, and dried over anhydrous magnesium sulfate. After removal of the solvent by evaporation, the residual product is recrystallized from ethanol and in the solution.
    As a result, 1-bromo 2- (2,4,6-tris (12.43 g, 0.104 mol)) is obtained in tetrahydrochlorophenoxy) -ethane in the form of white tverrofuran (400 ml) at -78 ° C in the atmosphere - Dog substance (39.4 g). Then mix
    50
    55
    in C, pyridine (60 ml) was added dropwise to the cooled suspension with simultaneous stirring. Then
    IU (250 ml) and washed with water (6 ml). The organic layer was dried over magnesium sulfate, filtered, and dissolved in a chromatographic column using a mixture of hexane ethyl ethyl acetate in a ratio of 75:25 l as eluent (8.6 g).
    Calculated,%: With 45.7; H 3.8; N 7.1.
    C, 5H (5C1, H2Og8
    Found,%: С 45.6; H 3.9; N 7.2.
    And pm. 2. A. Preparation of M-propyl-thiazole-5-carboxamide.
    Butyl lithium (2.4 mol, 50 ml) in hexane is introduced into a solution of nitrogen 2-chlorothiazosphere. The resulting
    dissolving the solvent by evaporation, the residual product is dissolved in ether, washed with water and the dried element forms N-nponnn-N-2- (2, 4,6-trichlorophenoxy) ethylamine as boxamide.
    after evaporative chromatographic separation on silica gel using chloroform as
    eluent forms N-nponnn-N-2- (2 4,6-trichlorophenoxy) ethylamine in the form of boxamide.
    oils (12.6 g).
    D. Preparation of N-nponmi-N- 2- (2,4, 6-trichlorophenoxy) ethyl-thiazole-5-kap Thiazole-5-carboxylic acid (4.8 g,
    0.037 mol), obtained in B, is heated under reflux with an excess of thionyl chloride (100 ml) in the tetasum product is suspended in dry pyridine (30 ml) and cooled in an ice bath for 10 minutes. A solution of M-propyl-M-2- (2,4,6-trichlorophenoxy) ethylamine (10.7 g, 0.038 mol), semi-pyridine is removed by evaporation, the residual product is dissolved in chloroformate.
    in C, pyridine (60 ml) was added dropwise to the cooled suspension with simultaneous stirring. Then
    The solid is suspended in dry pyridine (30 ml) and cooled in an ice bath for 10 minutes. A solution of M-propyl-M-2- (2,4,6-trichlorophenoxy) ethylamine (10.7 g, 0.038 mol), semi-pyridine is removed by evaporation, the residual product is dissolved in chloroformate.
    the body is removed. As a result, a light brown oil remains, which has
    IU (250 ml) and washed with water (6 ml). The organic layer was dried over magnesium sulfate, filtered, and the solvent was removed. As a result, a light brown oil remains which
    chromatographic column using a mixture of hexane ethyl acetate 75:25 l as eluent, the result is the desired product as a white solid
    va (8.6 g).
    Calculated,%: With 45.7; H 3.8; N 7.1.
    C, 5H (5C1, H2Og8
    Found,%: С 45.6; H 3.9; N 7.2.
    And pm. 2. A. Preparation of M-propyl-thiazole-5-carboxamide.
    Butyl lithium (2.4 mol, 50 ml) in hexane is introduced into a solution of 2-chlorothiazole (12.43 g, 0.104 mol) in tetrahydrofuran (400 ml) at -78 ° C in atm.
    nitrogen sphere. The resulting
    the solution is stirred for 5 minutes, after which isocyanate (11.25 ml, 0.12 mol) is added and the reaction mixture is stirred for another 10 minutes, after which it is hydrolyzed with water (100 ml). The solvent is removed in vacuo and the residue is extracted with ethyl acetate (2x400 ml). The combined organic extract is then washed with a saturated solution of sodium chloride, dried over magnesium sulfate and the solvent is evaporated. Acetic acid (110 ml) is added to the evaporation residue and the solution is heated to about 100 ° C, then zinc dust (11.8 g) is added and the mixture is heated under reflux for 1 hour. After
    The reaction mixture was basified with ammonium hydroxide and then extracted with ethyl acetate (4 x 250 ml). The combined organic extract was washed with a saturated solution of chloro-Butyl lithium (1.6 mol, 7.5 ml) in hexane and introduced into a solution of M-propylthiazole-5-carboxamide (1.7 g, 10 mmol) obtained in A, in tetrahydrofuran ( 80 ml) at -78 ° C in a nitrogen atmosphere. 15 The resulting solution is stirred for 10 minutes and then heated to room temperature, after which 2- (4-chlorophenoxy) -1 - (4-chlorophenol-sulfonyloxy) ethane (5.20 g, 15 mmol), obtained in stage B, dissolved in tetrahydrofuran (40 ml). The resulting solution is then heated under reflux for 5 days. After cooling, the solvent is evaporated and
    Yes, sodium, dried (MgSOt) and then the 25 ° daily production of GHT solution is concentrated. After evaporating si water: ethyl acetate in a ratio of 1: 4 of chromatographic separation of the residual product in a column of silica (500 ml). The organic layer is washed with a saturated solution of sodium chloride, dried (MgSO4), the N-propyl type is obtained as the eluent is evaporated, and as a result, ostazol-b-carboxamide (12.2 g) is
    gel using ethyl acetate in
    an oil which, after flash chromatography on silica gel using an ethyl acetate / petrolline ether mixture in a 1: 2 ratio, gives the desired product (2.42 g). Mass spectroscopy showed that the mass / charge ratio of the related molecular ion, K, is 324, which confirms that the molecular weight of the product is 324.
    pale yellow solid with so pl. 86 ° C.
    B. Preparation of 2- (4-chlorophenoxy) -1- - (4-chlorophenylsulfonyloxy) ethane.
    A mixture of 4-chlorophenol (28.3 g, 0.22 mol), ethylene carbonate (19.4 g, 0.22 mol) and tetraethylammonium iodide (10 g; 3.6 mmol) is heated at 160 ° C for 3 hours and then cooled to room temperature. The output of chloroform is 500 ml and the resulting solution is washed with water and then dried over anhydrous sodium sulfate. After evaporation of the solvent, 2- (4-chlorophenoxy) ethanol (40.0 g) is obtained, which is dissolved in ether (400 ml) containing triethylamine (20 g, 0.2 mol) A solution of 4 is added dropwise -chlorophenylsulfonyloxychloride (42.0 g, 0.2 mol) in ether (150 ml) and the resulting mixture is heated under reflux for 40 hours and then cooled. The precipitated product is filtered and thoroughly washed with dichloromethane. and washing is dried over anhydrous sodium sulfate. After removal of the solvent by evaporation, the residual product
    0
    recrystallized from ethyl acetate to afford 2- (4-chlorophenoxy) -1 - (4-chlorophenylsulfonyloxy) ethane as a white solid (34.6 g, mp. 108 ° C).
    C. Getting S-Propyl-M- | 2- (4- -chlorophenoxy) -ethyl thiazole-5-carboxamide.
    Butyl lithium (1.6 mol, 7.5 ml) in hexane is introduced into a solution of M-propylthiazole-5-carboxamide (1.7 g, 10 mmol) obtained in A, in tetrahydrofuran (80 ml) at -78 ° C in nitrogen atmosphere. 5 The resulting solution was stirred for 10 minutes and then warmed to room temperature, after which 2- (4-chlorophenoxy) -1 - (4-chlorophenol-sulfonyloxy) ethane (5.20 g, 15 mmol) obtained in B dissolved in tetrahydrofuran (40 ml). The resulting solution is then heated under reflux for 5 days. After cooling, the solvent is evaporated and
    0
    5 o daily production of GHGSTM mixture: ethyl acetate in a ratio of 1: 4
    |
    an oil which, after flash chromatography on silica gel using an ethyl acetate / petrolline ether mixture in a 1: 2 ratio, gives the desired product (2.42 g). Mass spectroscopy showed that the mass / charge ratio of the related molecular ion, K, is 324, which confirms that the molecular weight of the product is 324.
    II p and measure 3. Preparation of M-propyl-N-2- (4-chlorophenoxy) ethyl) -thiazole-5-β-thiocarboxamide.
    |
    A mixture of M-propyl-H-2- (4-chlorophenoxy) ethyl thiazole-5-carboxamide (0.9 g, 3 mmol) obtained in example 2B and Lossen's reagent 2,4-bis (4-methoxyphenyl) -1,3-dithia-2,4 diphosphetan-2,4-disulfide (1.2 g, 3 mmol) is heated under reflux for 20 hours and then cooled to room temperature. Water (100 ml) was added and the residual product was extracted into ether (2 x 200 ml). The combined organic extract is washed with a saturated solution of sodium chloride (50 ml) and dried over sulfate
    magni. After evaporation of the solvent, an oil remains which, after flash chromatography on silica gel using ethyl acetate-petroleum ether in a 1: 1 ratio as eluant, gives the desired product as a yellow oil (0.75 g); 340.
    II groups 4 - 43. Having carried out the procedures similarly to the description of examples 1-3, other compounds are obtained by the proposed method described in detail in Table. 1. In this table, compounds are defined with a drop on formula I. The characteristics of these compounds are given in table. 2
    The compound of example 25 table. 1 and 2 are obtained as follows.
    Example 25. Obtaining N- (4- -chlorophenylcarbonyl) orthophenylene-thiazole-5-carboxamide.
    A solution containing 5-thiazolecarboxylic acid (1.5 g) in thionyl chloride (40 ml) is heated under reflux for 2 hours and then cooled to room temperature.
    The excess thionyl chloride is removed under reduced pressure and the residue is dissolved in pyridine (20 ml) and poured into a solution of 2-amino-4-chlorobenzophenone (2.7 g) in pyridine (20 ml). After heating under reflux for 1 hour, the reaction mixture is concentrated, suspended in water and then extracted in dichloromethane.
    The organic extract is then dried over magnesium sulfate, filtered and concentrated. The residual solid is recrystallized from ethanol to give M- (4-chlorophenylcarbonyl) orthophenylene-thiazole-5-carboxamide, m.p. 168-169 ° C.
    The structure and elemental analysis of the compound are also given in Table. 1 and 2.
    Example 44. The fugcicide effect of the compounds obtained by the proposed method was studied by carrying out the following tests.
    but). Activity as anti-sporula nta against grape powdery mildew (Plasmopara viticala; Pva). This test is a direct test for antisporulating action by spraying the foliage. Lower leaf surfaces of grape plants (cv Cabernet Sauvignon)
    Q $
    0
    five
    0 5
    0
    five
    0
    five
    was inoculated by spraying with an aqueous suspension containing 10 zooporangia / ml for 2 days. before treatment with the test compound. Inoculated plants were maintained for 24 hours in a chamber with high humidity, then for 24 hours in a greenhouse at room temperature and humidity. Infected leaves were sprayed on their lower surface with a solution of the active material in a water / acetone mixture in a 1: 1 ratio containing 0.04% Tween 20 (Trade mark; polyoxyethylene sorbitan ester surfactant). Spraying was performed using a sprayer with a dose of 1 kg / ha. After spraying, the plants were again placed in normal greenhouse conditions for 96 hours, then transferred to a high humidity chamber for a period of 24 hours in order to induce sporulation prior to taking measurements. The determination is based on the measurement of the percentage of leaves spore-plated compared to control leaves.
    c) Direct protective action against downy mildew of grapes (Plasmopara viticola; Pvp).
    This test is a direct protective action using foliar spray. The bottom surfaces of the leaves of grape plants (cv Cabernet Sauvignon) were sprayed with the test compound at a dose of 1 kg of active material per hectare using a sprayer driven as described in Section A, and after the next 24 hours of exposure under normal greenhouse conditions, the lower surfaces of the leaves were inoculated by their spraying with an aqueous solution containing 10 zoospores / ml. Inoculated plants were maintained for 24 hours in a chamber with high humidity, 5 days under normal greenhouse conditions, and then placed again for another 24 hours under conditions of high humidity. The determination is based on the measurement of the percentage of leaf area covered by the sporulation compared with control leaves.
    with) . Direct 4 protective action against gray mold of grapes (Botrytis cinerea; Ver).
    This test is a direct protective action using foliar spray.
    The bottom surfaces of the separated leaves of a grape plant (cv Cabernet Sauvignon) were sprayed with the test compound at a dose of 1 kg / ha using a spray gun as shown in section A. After spraying for 24 hours, the leaves were inoculated with water droplets containing 105 conidia / ml. After another 5 days of exposure to high humidity conditions, the percentage of leaf area subjected to the disease was determined.
    (d) Activity against leaf leafiness (Leptosphaeria sinus; Ln).
    This test is a direct therapeutic test using foliar spray. Leaves of wheat plants (cv Mardler) at the stage of appearance of a single leaf were inoculated by spraying with an aqueous suspension containing K10 ° spores / ml. The inoculated plants were kept for 24 hours in a high-humidity chamber, after which they were treated. The plants were sprayed with a solution of the test compound with a dose of 1 kg of the active material on a drying of a sprayer with a drive, as described in section a). After drying, the plants were kept for 6-8 days.
    ten
    15
    up to 7 days, after which the determination was made.
    The determination is based on the percentage of leaf area covered by sporulation compared with the leaves of control plants.
    f) Active against brown wheat rust (Piccinia recondita; Pr).
    This test is a direct protective action using a foliar spray. Wheat hay seeds (cv Brigand) were grown to a stage of appearance of 1-1 and 1/2 sheets. Then the plants were sprayed with the test compound at a dose of 1 kg / ha using a sprayer with a drive,
    as described in section 20 a). The test compounds were used in the form of solutions or suspensions in a mixture of acetone and water (50: 50 v / v) containing 0.04% surfactant (Tween 20).
    25 18-24 hours after treatment, the seedlings were inoculated by spraying the plants from all sides with an aqueous spore suspension containing approximately 105 spores / ml. 18 hours after inoculation, the plants were kept in high humidity at 20-22 ° C. After that, the plants were kept in normal greenhouse conditions, i.e.
    under moderate relative conditions
    og
    at 20-25 ° C and under moderate conditions
    moisture, after which it was carried out out of Disease measurement. The determination is based on a density of 10 days after inoculation of damage per leaf in comparison with the leaves of control plants.
    e) Activity against barley powdery mildew (Erysiphe JQ m. graminis f. sp. hordei; Eg). g) action against blas This test is a direct theory of rice leaf (Pyricularia ory- therapeutic test using foliar spray. The leaves of barley seedlings (cv. Golden Promise) 45 were inoculated by spraying with conidia of downy mildew 1 day prior to treatment with the test compound. The inoculated plants were kept overnight in the greenhouse conditions of §0 at room temperature and humidity,
    based on the percentage of plant covered with sporulating blistering, compared to control plants zae; Po).
    This test is a direct therapeutic test with foliar spray application. A leaf of rice seedlings (approximately 30 seedlings per pot) was sprayed with an aqueous suspension containing 10 5 spores / ml for 20-24 hours before treatment.
    test compound. The inoculated plants were kept overnight in high humidity conditions and then dried, then sprayed with the test compound 1 kg of active material per hectare using a sprayer with a drive as described in section a). After processing
    after which they were processed. Plants were sprayed with the test compound at a dose of 1 kg of active material per ha using a spray gun as described in section a). After drying, the plants are again placed in a chamber with a temperature of 20-25 ° C and with moderate humidity for a period of
    up to 7 days, after which the determination was made.
    The determination is based on the percentage of leaf area covered by sporulation compared with the leaves of control plants.
    f) Active against brown wheat rust (Piccinia recondita; Pr).
    This test is a direct protective action using a foliar spray. Wheat hay seeds (cv Brigand) were grown to a stage of appearance of 1-1 and 1/2 sheets. Then the plants were sprayed with the test compound at a dose of 1 kg / ha using a sprayer with a drive,
    as described in the wet room and at. The disease was identified 10 days after inoculum.
    mi g) Activity against blasting based on the percentage of plant covered with sporulating blistering, compared to control plants on rice leaf plants (Pyricularia ory-
    zae; Po).
    This test is a direct therapeutic test with foliar spray application. A leaf of rice seedlings (approximately 30 seedlings per pot) was sprayed with an aqueous suspension containing 10 5 spores / ml for 20-24 hours before treatment.
    those leaves of rice (Pyricularia ory-
    test compound. The inoculated plants were kept overnight in high humidity conditions and then dried, then sprayed with the test compound 1 kg of active material per hectare using a sprayer with a drive as described in section a). After processing
    one
    The plants were kept in a rice chamber at 25-30 ° C and under conditions of high humidity. The determination was carried out 4–5 days after treatment and were based on data on the density of necrotic lesions per leaf compared to control plants.
    h) Active against early tomato rot (Alternaria solani; As).
    In this test, the contact prophylactic activity of the test compounds applied to the foliage by spraying was measured.
    Tomato saplings (cv Outdoor Girl) were grown to the stage where the second true leaf was completely dissolved. The plants were treated using an atomized sprayer as described in section a). Test compounds were applied as solutions or suspensions in a mixture of acetone and water (50:50 v / v) containing 0.04% surfactant (Tween 20).
    One day after this treatment, the seedlings were inoculated by spraying the upper leaf surfaces with a suspension of A.solani conidia containing 104 spores / ml. After 3 days after inoculation, the plants were moistened in a greenhouse with a relative humidity of about 100% (RH) and with a temperature of 21 ° C. The plants were then kept under wet, but not saturated conditions.
    The disease was determined 7 days after inoculation; it was based on the density and distribution of damage.
    i) Active against the orbital staining of wheat under in vitro conditions (Pseudo ccosporella her- 45 potrichoides; Phi).
    In this test, the conditions of activity
    po compounds against fungi, challenges
    glacial stains of wheat. The test compound was dissolved or suspended in acetone, injected into molten half-strength potato dextrose agar, and a final concentration of 100 ppm and 3.5% acetone was obtained. After agar formation, the plates were inoculated with 6 mm diameter agar / mycelium swabs taken from

    ten
    15
    20
    25
    thirty
    35
    - dd 1
    14-day culture P. herpotrJchoi- des. The plates were incubated at 20 ° C for 12 days and the radial growth from the inoculation tag was measured.
    j) ACTIVITY action against Fusarium under in vitro conditions (Fusarium species, Fsl).
    In this test, the activity of these compounds was measured under in vitro conditions against seeing Fusarium, which cause stem and root rot.
    The compound was dissolved or suspended in acetone and introduced into molten half-strength potato dextrose agar, so that the final concentration was 100 ppm of the compound and 3.5% acetone. After agar formation, the plates were inoculated with 6-mm-diameter tampons of agar and mycelium, taken from a 7-day culture of Fusarium sp.
    The plates were incubated for 5 days and the radial growth from the swab was measured.
    The degree of disease reduction in all the above tests was assessed by comparison with the degree of disease reduction without treatment, and with the degree of disease reduction with a diluent-spraying according to the following criteria:
    O - reduced disease less than
    by 50%;
    decrease in disease approximately
    by 50-80%;
    decrease in disease more than
    by 80%.
    The test results are shown in Table. 3
    1 o
    II p and mep 45. Comparative tests of the fungicidal action of the compounds obtained by the proposed method in comparison with the closest analogues in structure and action
    Compound A
    OS1
    C-N-CH2-CH2--0-xЈ3 PS3N7
    Compound B
    ch3
    N o
    Ct v
    N
    ff V-C-N-CH-rCHf (HI
    i-i ../
    nc3H7
    Cl
     J1
    fush the FUNG activity of compounds A and B against Pyricul-aria ogukae (Ro) Erysiphe graminis (Kg) and Lcptosphaeria modorum (Ln) were compared with the activity of the compound of example 1 according to the methods of example 44 (g), (e) and (d), but using a dosage interval and rating scale in the range of 0-9, where
    0-0-9% disease control; .
    1-10-19% disease control; Up to 9 - 90-100% disease control.
    The test results are given in Table 4.
    The compound of Example 1 has a higher activity against Pyricularia oryzae (Po) than the compounds A and B, has a higher activity than the compound A against Erysiphe graminis (Eg) and Leptosphaeria nodorum (Ln) and has at least equal activity Compound B versus the last two diseases. The comparative data presented demonstrate the desired positive effect of the compounds of the invention.
    Thus, the proposed compounds are promising for the creation of new highly effective fungicides.
    权利要求:
    Claims (1)
    [1]
    Invention Formula
    The method of producing thiazole derivatives of general formula I
    Y
    35
    Q - (CH) m - X - R
    four
    where R, X and p have the indicated meanings;
    JWSVC N-tZ) m-tCHlV-X R U) 40Q - group (Z) №NHR4,
    | l for I, where R, ta and Z have the indicated values - N RT. - ni;
    where R is phenyl, substituted by one mixture; Q is a group of the formula —O — SO —R., where a titanium selected from the atom 4 is a halogen-substituted phenyl, with us-halogen, C — C-alkyl, cyano- “(Lovia, P is a halogen atom, then Q is a group, cyclohexyl and phenyl, the group is - (, or if P is a group-phenyl substituted by two atoms -pah-NHR2, then Q is the group -D-SC -R., Mi halogen, phenyl , substituted-and the resulting compound of three substituents, select-formula I, where Y is oxygen, isolated from halogen atoms and JQ, or it is subjected to the interaction of the nitro group, or naphthyl, with a thiecting agent obtaining displacements with a halogen atom; the desired product Niemi, wherein Y - sulfur.
    Q
    five
    S
    14
    C. is hydrogen, (1 - (- alkyl, possibly substituted by a methoxy group, or C is alkynyl;
    R, is hydrogen or chlorine, C-Cf-alkoxy-, or C4-C 4 alkylthio, or morpholino; X is oxygen or sulfur; t O or X is carbonyl or di (C -C-alkoxy) methylene; m 1;
    Y is oxygen or sulfur; n is an integer from 0 to 3; Z - pheny en
    characterized in that the compound of general formula II
    W-p
    where K3 has the indicated meanings; P - halogen atom or group
    -NHR, where R2 has the indicated meanings,
    subjected to interaction with the compound of the formula
    35
    Q - (CH) m - X - R
    four
    The structure of the compounds of formula 1
    b p p 1
    T a b l
    and c
    one
    0.1 0.1 0.1
    one
    0.1
    0.5
    0.01
    0.1
    0.5
    0.01
    0.1
    /, 3
    1.0 8.0
    Eg 3.6 3.6 8.0 9.0 9.0 9.0 9.0 9.0
    21
    example 1
    0.1
    0.25
    0.5
    1.0
    0.1
    0.25
    0.5
    1.0
    0.03
    0.1
    1579458 Continuation of table 4
    22
    rotiv Ln
    . 3.4 4.0 4.0 6.0 9.0 9.0 9.0 9.0 9.0 9.0
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    US4670451A|1987-06-02|Benzoxazolone-2 compounds and fungicidal use thereof
    RU2049782C1|1995-12-10|Thiazole derivatives, method of their synthesis, method of struggle against fungi
    JP2007084566A|2007-04-05|Agricultural and horticultural disease controller and method of using the same
    EP0404498A2|1990-12-27|Novel halo propargyl compounds, and uses and processes of preparation thereof
    IL24814A|1971-04-28|N&#39;,n&#39;-disubstituted-thiono carbamyl thiolo-imides and process for their preparation
    RU2066320C1|1996-09-10|Thiazole derivatives, processes for preparation thereof, and method for controlling fungi
    CS212230B2|1982-03-26|Fungicide means and method of making the active agent
    SU373915A1|FUNGICIDE
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    US5945436A|1999-08-31|Pyridylmethyl nitriles, amides and thioamides useful as fungicides
    同族专利:
    公开号 | 公开日
    EP0296673B1|1994-03-09|
    DK346788D0|1988-06-23|
    AU1832988A|1989-01-05|
    US4877802A|1989-10-31|
    DE3888245D1|1994-04-14|
    JPS6426572A|1989-01-27|
    CA1328867C|1994-04-26|
    KR890000449A|1989-03-14|
    DE3888245T2|1994-06-16|
    EP0296673A1|1988-12-28|
    GB8714920D0|1987-07-29|
    ES2061628T3|1994-12-16|
    DK346788A|1988-12-26|
    AU615658B2|1991-10-10|
    CN1022015C|1993-09-08|
    CN1033626A|1989-07-05|
    AT102611T|1994-03-15|
    DK169743B1|1995-02-13|
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    法律状态:
    优先权:
    申请号 | 申请日 | 专利标题
    GB878714920A|GB8714920D0|1987-06-25|1987-06-25|Thiazole derivatives|
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