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    • 专利摘要:
    1,2,3-thiadiazole-5-carboxylic acid derivatives having herbicidal and growth regulating activity and having the formula <IMAGE> I in which R1 is hydrogen or is alkyl of which the chain may be interrupted in one or several places by oxygen or sulfur or which may be substituted by halogen and in which X is (a) -Y-R2, wherein R2 is hydrogen, alkyl which may be substituted, aryl which may also be substituted, aryl-C1-C2-alkyl which may also be substituted, or a univalent metal equivalent and wherein Y is oxygen or sulfur, or (b) wherein X constitutes the residue <IMAGE> wherein R3 and R4 may be the same or different and have the meaning further defined in claim 1 of the accompanying specification. The compounds are soil- or leaf-applicable herbicides with a high activity against seed weeds and resistant weeds.
    公开号:SU816401A3
    申请号:SU782625900
    申请日:1978-06-16
    公开日:1981-03-23
    发明作者:Арндт Фридрих；Крюгер Ханс-Рудольф；Руш Райнхарт
    申请人:Шеринг Аг (Фирма)；
    IPC主号:
    专利说明:

    (54) METHOD FOR OBTAINING DERIVATIVES OF 1,2,3-TIADIAZOL-5-CARBIC ACID
    1,2,3-thiadiaaol-B-carbne formula
    P1
    Ifle R has the indicated values, is reacted with Compound III HX, where X has the indicated values at a temperature from to room temperature in an organic solvent medium and in the presence of an acid binding reagent.
    The proposed compounds are characterized by soil and / or foliar herbicidal action against weed seeds and against germinated weeds. The action is partially systemic. The fight against wildcorn and binocular weeds is particularly effective, such as Digitalis, Trifolium, Portulaca, Papaver, Oancus, Kochia, Gypsophyia, Lactuca, So 1anum, Escho1 tzia, Cheiranthus, Phace1 ia, Euphorbia Linum, Brant, Brant, Brant, Brands, Brands, Brands, Brands, Brands, Brands, Brands, Brands, Brands, Brands, Brands , Jpomoia, Se ta ria, Ag ros tis, Phleum, Alopecurus, Phalaris, Dactylis, Festuca, A g rhe.na te r urn, Lo 1 i urn, Bromus., Aveno, Allium, Cucumis, Medicago, Stellaria, Seneclo, Matricaria, Lanuiem, Centaurea, Aroarantus, Galeum Chrysathemum, Polygonum, Sorghum, Alopecurus, Echiuochloa, Digitaria, Cyperus. Poaund andere.
    Expenditure amounts for weed control range from 0.5 to 5 kg of effective substance per hectare.
    Selective weed control is possible, for example, in cereals, cotton, soybeans and plantation crops. These substances are most effective when they are sprayed onto weed seeds or their germinated parts. These cultures can be sown in rows a few days after spraying.
    The proposed compounds may also alter the natural development of plants to enrich various agricultural or horticultural properties.
    The interaction of the components of the reaction takes place in the temperature range 0-120 ° C, however, as a rule, at room temperature and the reflux temperature of the corresponding reaction mixture,
    Approximately equimolar amounts of reagents are used to synthesize new compounds. Suitable reaction media are solvent inert to the reagents. As such, the following should be mentioned: halogenated hydrocarbons, aliphatic and aromatic hydrocarbons such as petroleum ether, cyclohexane, benzene, toluene and xylene, methyl isobutyl ketone and
    isophorone, ether, like diethyl ether, tetrahydrofuran and dioxane, and nitriles of carboxylic acids, like acetonitrile.
    Organic bases, such as triethylamine, N, N-dimethylaniline and pyridine bases or inorganic bases, such as oxides, hydroxides and carbonates of alkali and alkaline earth metals, are suitable as acid acceptors. Liquid bases like pyridine can be used simultaneously as a solvent.
    The compounds obtained by the method described above are taken out of the reaction medium by conventional methods, for example, by distilling off the used solvent under normal or reduced pressure, by precipitating with water or by fractional distillation.
    Example 1. 4-Methyl-1,2,3-thiadiazole-5-ethyl ester of carbonic acid (compound 1) CH
     s-os, n,
    about 25 o
    101.2 g (1.0 mol) of triethylamine dissolved in 500 ml of tetrahydrofuran, treated at room temperature with 46.1 g (1.0 mol) of ethanol. With constant stirring and cooling, 162.6 g (1.0 mol) of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid chloride are added dropwise over one hour. Stir at room temperature for 4 hours, finally the precipitate is filtered off and the filtrate is evaporated. The pulp is treated in methylene chloride. After washing with water, the methylene chloride phase is dried over magnesium sulfate, the solvent is removed, and the remaining product is subjected to distillation under reduced pressure.
    The yield of 159.0 g (92.5% of theoretical).
    Colorless liquid with boiling point bb-69 C / O, 5 torr.
    Example 2. 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid (compound 2)
    U-
    by
    32.5 g (0.2 mol) of 4-methyl-1,2 3-thiadiazole-5-carboxylic acid is treated with 160 ml of 3 N sodium hydroxide in methanol and stirred at room temperature for 2 hours. Then the methanol is evaporated under vacuum and the resulting salt mixture is washed with ether. Finally, the salt is dissolved in 200 ml of water and acidified with a weak solution of hydrochloric acid. The solution is filtered and taken up with pentane. Recrystallization is carried out with ethyl acetate and hexa. The yield is 27.9 rf97% of theoretical, colorless crystals with a melting point of 174-175 s. Example 3, 4-Methyl 1,2,3 thiadiazole-5 carboxylic acid (compound 3) 4 (9.4 g (0.075 mol) 4-fluorobenzylamine dissolved in 100 ml of tetrahydrofurm, mixed at room temperature 10 , 4 ml 0.075 mol) three ethylamine. Under stirring and cooling at 10 ° C, 12.2 (0.75 mol) of 4-methyl chloride 1,2, 3-thiadiazole-5-carboxylic acid chloride with a melting point of 48-50 s at 0.5 mm Hg are added dropwise. The solution was dissolved in 50 ml of tetrahydrofuran in. The mixture was stirred for another 4 h. After the residue was aspirated, the filtrate was evaporated and mixed with ether. The mixture was recrystallized from ethanol. The yield was 14.2 g (75.5% of the theoretical). Colorless crystals with m.p. 106107 C. Example 4. 4-Methyl-1,2,3-thiadiazole-5-carboxylic acid (cyclohexylmethyl) amide (compound 4) 16.3 g (0.1 mol) 4-metil-1,2 , 3-thia diaeol-5-carboxylic acid chloride solution with stirring and cooling, add dropwise to a solution of 11, 3g (0, .1 mol) aminomethylcyclohexane in 50 ml of pyridine. Stir for 3 hours. The reaction mixture is poured into ice. the water that forms the oily substance separates with and is degenerated with isopropyl ether, Recrystallization is carried out by means of cyclohexane. Yield 22.9 g (96% of theoretical). Colorless crystals with a melting point of 79-80 ° C. The starting material for the preparation of compound 3 is 4-methyl -1,2 chloride, 3-thiadiazole-5-carboxylic acid. 103.6 g (0.72 mol) of 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid are added in portions to 280 ml of thionyl chloride. Then the reaction mixture is heated for 3.5 hours under reflux and then the thionylide is distilled off and the remaining residual is distilled off under reduced pressure. Obtain 102 g of 2% of theoretical) in the form of a demon's liquid with T.kip. 48-5 ° C 0.5 mm Hg The following compounds can be obtained taxically: 4-methyl-1, 2,3-thiadiazole-5-carbonot anilide. pl.116-117 0 EOI KI SLOTS 4-methyl-1,2,3-thiadiazol-5- 2-chlorohydride carboxylic acid; Same as 106-107С lots of 3-chloroanilide 4-methyl-1, 2,3-thia-diazol-5-carboxy- 137-138C of new acid 3,4-Dichloroanilide 4-methyl-1,2, 3-thiadiazole -5carboxylic acid 145-136 0 lots of 4-chloro-2-methylanilide 4-methyl-1, 2,3-thiadiazole-5-carbonic 142-143 ° 0 acid of 2-methyl-aniline-4-methyl-1, 2.3 -thiadiazole-5-carboxylic acid 115-11bots of 3-methylanilide 4-methyl-, 2,3-thiadia ol-5-car116-I7 0 bonoic acid 4-methyl anilide 4-methyl-1,2,3-thiadiazole-5-carboxylic118-119 0 3-Trifluoromethylanilide acid 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 123-124 0 4-fluoroanilide acid 4-methyl-1, 2,3-thia-diazole-5-carboxy YV About new acid 4-Nitroanilkd 4-methyl-1, 2,3-thiadiazole-5-carbonoo-179-180o acid N-MethylaniLschd 4-methyl-1, 2,3-thiadiazole-5-carbono-84-85 0 of acid dimethylamide 4 -methyl-1, 2,3-thiadiazolt-5-car6oT. pl. 120-125 with. New acid N-Benzyl-N-2-propionyl 4-methyl-1 2, 3-thiadiazole-5-carbo. 20
    1.5848 new acid
    9.4-Chloranilide 4-methyl-1, 2,3-thiadiazole-5-carbon
    M.p.121-122C acid
    0.3,5-dichloroanilide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid 195-196 C lots
    1. Benzyl amide 4-methyl-1, 2,3-thiadiazole-5-carbono63-64 With howl acid
    2. Ethyl ether
    1,2,3-thiadiazole-5-carboxylic
    T.kip.55-57
    acid at) (about, 5 mm hg.
    3.4-Chlorobenzylamide 4-methyl-1, 2,3-thiadiazole-5-carbonot Tpl.109-110 ° С
    4.2-Chloro-6-methylamide-4-methyl-1, 2,3-thiadiazole-5-carboxylic
    133-134 ° C acid
    5.N-Cyanmethyl-3, 6-dimetylanilide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid, 118-119s lots
    6 .. 2, .b-dimethylanilide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid 100-101 C lots
    7.2,6-Dichloroanilide 4-methyl1,2, 3-3-thiadiazole-5-carbonoib-IV With howl acid
    28.Distilamide 4-methyl-1,2,3-thiadiazole-5-carboxy 111-114 with a new acid
    29. 2-Pyridylmethylamide 4-methyl-1,2, 3-thiadiazole-5-car75-76 C of boic acid
    30.3-Pyridylmethyl 4-methyl-1,2,3-thiadiazole-5-carT. Mp. 95-96 With bonoic acid
    31.2-Chlorobenzylamide 4-methyl-1,2,3-thiadiazole-5-car68 0 bonoic acid
    32.3,4-Methylenedioxybenzylamide 4-methyl-, 2,3-thiadiazole-5-carbon-87-88c acid
    33. Diisopropylamide
    4-methyl-1,2,3-thiadiazole-5-carbo89-91 C nova acid
    34. M-Venzyl-Y-methylamide-4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid, 1.5838 lots
    D
    35.2,4-Dichlorobenzylamide 4-methyl-1,
    2, 3-thiadiazole-5-carboxylic acid T.pl.1L9-111 with lots
    36.3,4-Dichlorobenyl 3-4-methyl-1, 2,3-thiadia-3-5-carboxylic
    109-110С acid
    0 37. 3-Chlorobenzylamine 4-methyl-1, 2,3-thiadiazole-5-carbo 64-65 With a new acid
    38.2-methoxybenzylamide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid 96-97 with lots
    39.3-Methoxy-benzylamide 4-methyl-1,2, 3-thiadiazole-5-car-75-75c of boic acid
    40.4-Methoxybenzylamide 4-methyl-1,2, 3-thiadiazole-5-car115-117 C of boic acid
    41.4-Methylbenzylamide 4-methyl-1,2,3-thiadiazole-5-carbonyl 115-116 0 acid
    42.2-Fluorobenzylamide 4-methyl-1,2,3-thiadiazole-5-car108-109 C bonoic acid
    43.N-Ethyl-N-benzylamide 4-methyl-1,2,
    3-thiadiazole-5-carboxylic acid
    1,5751 lots
    44.Y-Banzil-Y-isopropylamide 4-methyl-1, 2,3-thiadiazole-5-carboxylic
    20 3)
    1.5695 acid
    45.P-5enzyl-P-butylamide-4-meth il.
    1,2, 3-thiadiazole-5-carboxylic acid 20
    1,5623 lots
    46.3-Methylbenzylamide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid. Mp. 52-53 C lots
    47.2-Naphthyl-methylamide-4-methyl-1, 2,
    five ; Z-thiadiazole-5-carbonrva to lots 48.3,5-Dimethylbe zylamid 4-met -1,2,3-thiadia-5-carboxylic lots 49.4-t-butylbazylamid-4-1-1, 2,3-thiadiazole-5bonic acid 50 . Cyclohexyl 4-methyl-1,2,3-thiadiazal-5-caroic acid 51. 4-methyl-1, 2,3-thialium-5-carboxylic acid cyclooctylamide 52. Cycloheptyl 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid 53. 4-methyl-1, 2,3-thiadisole-5-carbonic acid cyclopentyl amide 54. 4-methyl-1, 2,3-thiadiasol-5-carbonic acid cyclopropylamide 55. Butylamide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 56.2-Methylpropyl amide 4-methyl2, 3-thiadiazole-5- carboxylic acid 57.1,1-dimethylethylamide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 58.2-4-methyl-1 propenylamide, 2,3-thiadiazole-5-carboxylic acid 59. ethoxycarbonylmethylamide 4-methyl- 1,2,3-Thiadiazole-5-carboxylic acid 160. 2-Ethoxyethylamide 4-methyl-1, 2,3-thiadisole-5-carbonic acid 1,1-DIETHYL-2-propylamide 4-m &amp; 1, 2,3-thiadiazole-5-carboxylic acid m.p. 74-75c acid 2,2-diethoxyethylamide 4-methyl-1, 2,3-thiadiazole-5-carbop 1.5089 nova acid 3-dimethyl-aminopropylamide 4-methyl-1, 2,3-thiadiazole-5-carboxy 1 , 5290 iovoy acid Diphenylamide 4-methyl 1,2,3-thiadiazole-5-karboT. Pl.116-119 With new acid 1-Ethinyl-cyclohexylamide 4-methyl-1, 2,3-thiadiazole-5-carbono91-93 C BOrt acid (4-Methyl-1,2,3-thiadiazol-5-yl) p 1.5618 pyrrole and n o on n (. 4-Methyl-1,2,3-thiadiazol-5-yl) p 1.5550 piperidine ketone 2-furfurilamide-4-methyl-1, 2, .3-thiazolol-5-kapT. 49-50 With bonovoy acid (4-Methyl-1,2,3-thiadiazol-5-yl) 85-86 ° C morpholinoketone Cyclopropylmethylamide 4-methyl-1, 2,3-thiadiazole-5 - "arbonic nj 1,5470 acids Morpholinoamide 4-methyl-1., 2, 3-thiadiazole-5-carboxylic acid. pl.184-185 C lots Piperidinoamide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 155-156 C you N -Benzyl anilide 4-methyl-1,2,3-thiadiazap-5-carboxylic acid83-84 C lots Propylamide 4-methyl-1, 2,3-thiaiazole-5-carboxylic acid 1.5360 you zopropylamide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 72-73 C
    2,3-thiadiazole-5-carboxylic
     1.5838
    acids
    1. Cyclohexylmethyl 4-3THJJ-1, 2,3-thiadiazole-5-car6onop 1.5352 acid
    2. Ethyl ester of 4-ETHYL-1,2,3-thiadiazop-5-carbonic acid; bp 74-75 C lots
    at Hg
    4-Propyl-1,2,3-thiadiazole-5-carboxylic
    M.p.101-103 C
    acids {1,2-diphenyl-.
    4. ethyl) -amide-4-methyl-, 2,3-thiadiazole-5-carbono-158 carbonic acid
    IN- (2-cyanoethyl) -benzyl-amide-4-methyl-1, 2,3-thiadia ol-5-carbo83 C
    new acid
    1- (4-Fluorophenyl) -ethyl-4-methyl-1, 2,3-thiadiazole-5-carboxylic
    acids
    (N-methylcyclohexylmethyl) -amide-1, 2, 3-thiadiazole-5-carboxylic
    p 1,5414 acids
    (4-Methylbenz yl) amide-propyl-1,2, 3-adiazole-5-carboxylic acid. Mp. 78 C lots
    (4-Chlorobenzyl) 9; -amide-4-propyl-1, 2,3-thiadiazole-5-carbono102-103 of C acid. (4-fluorobenzyl)
    00 amide 4-propyl-1, 2,3-thiadiazole-5-carbonon-n-is c acid. (3,4-Dichloroben101 3 yl) propyl-1, 2,3-thiadiazole-5-carboxylic
    97-98 With acid
    02
    4-PROPIL-1,2,3-thiadiazol-5-car-75-75 C-cyclohexylamide of bovic acid. 2-Methyl cyclic hemol 4-propyl-1, 2,3-thiadia-3 el-5-carbne
    acids 104.3-methylcyclogelamide 4-propyl-1, 2,3-thiadiazole5-carboxy; a new acid-105,4-methylcyclohexylamide 4gp drank-1,2,3-thiadiazole-5-carboxylic acid 106. (cycloheptylmethyl) amide- 4-propyl-1, 2,3-thiadiazole-5-carboxylic acid 107. (Cycloooctylmethyl) amide-4-propyl-1, 2,3-thiadiazole-5-carboxylic acid 108.3-4-methyl-1,2-hydroxyanilide, 3-thiadiazole-5-carboxylic acid 109.4-Chlorophenyl ester 4-methyl-1, 2.3 thiadiazole-5-carboxylic acid 110. (Cyclohexylmethyl) amide-1,2-thiadiazole-5 carboxylic acid 111.3 / 4-Dichlorophenyl ester 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid, 112.1 enyl The th ester of 4-methyl-1,2,3-thiadiazole-5-carboxylic acid is 113 (1,3-Dimethylbutyl) amide-4-methyl-1, 2,3-thiazolol-5-carboxylic acid 114. ( 3-Methylbutyl) amide-4-methyl-1 2, 3-thiadiazolecarboxylic acid 115. (1-Oxycyclohexylmethyl) amide-methyl-1, 2,3-t diazole-5-carboxy acid of 116. (2- Dimvitylamine ethyl) amide-4-methyl-1,2,3-thiad aeol-5-carboxylic acid 117. (3,3-Dimethylbutyl) -amide-4-mvtil-1, 2,3-thiadiazole-5-carboxylic acid m.p. 50-52 C 118.3-Phenoxybeneyl ester 4-methyl-1,2, 3-thiadia ol-5-carbono1, 5989 acrylic acid 119.3-Methyl rbamoyloxy-1Nilide 4-methyl-1,2,3-thiadiazole-5-carboxylic So pl . acids (Rael.) Compounds 1 are generally colorless, odorless, crystalline substances or odorless, colorless liquids that are difficult to dissolve in water, relatively soluble in aliphatic hydrocarbons like petroleum ether and diclohexane, readily soluble in halogenated hydrocarbons like chloroform and carbon tetrachloride as benzene, toluene and xylene, ethers like diethyl ether, tetrahydrofuran and dioxane, in nitriles of carboxylic acids like acetonitrile, ketones like acetone, alcohols like methanol and ethanol, in amides of carboxylic acids such as dimethylformamide, and sulfoxides such as dimethyl sulfoxide. Cyclohexane, acetonitrile and alcohol are particularly suitable solvents for recrystallization. 1,2, 3-Thiadiazole-5-carboxylic acids and their salts are well soluble in water and, on the contrary, poorly dissolved in organic solvents. The starting materials for the preparation of the new compounds are known compounds or can be obtained by known methods. Example 5. In the greenhouse, the compounds listed in table. 1, emulsified, 5 kg of an effective substance per hectare in 600 l of water sprayed onto test subjects, synapis (Si), solar tSoJ, 6eTa (Be), gossypium (Co), chordium (Ho), Cea mais (Ze), lolium (LO) and setari (Se) in the experiments before and after germination. 3 weeks after the treatment, the scenes are staged; ku, and take the following notation: O - no action, 1-2 - eff; growth control effect in the form of intensive coloring of primary leaves / growth retardation, formation of buds and processes, depression and growth of leaves, slight development of roots} 3-4 - plantine are no longer viable Y - experience before germination N experience after germination . Example 7. 4-methyl-1t2, 3-thiadiazole-5-carboxylic acid 4-methyl-1t2, 3-thiadiazole-5-carboxylic acid and 4-methyl-1, 2.3 tig "iazole-5-carboxylic acid 4-methylcarboxylic acid" emulsified in 500 liters of water per hectare with consumable rates of 1 kg of an effective substance per hectare per plant the following weeds: Stel1ag1a, Senecio, Matricaria, Lamium, Centaurla, Amaranthus, Galium, Chrysanthemum, Lponoca, Polygomem, Brassica, Sblamum, Alllum, Ptsuom, Portulaca, Kachia, Dususus, Saneuma, Sblamum, Alllum, Ptsuom, Portulaca, Kusia, Dusususa, Saneuma, Sblamum, Alllum Euphorbia, Datura, Cbehorium. Bee the indicated plants were destroyed. After 2 days after that in about. the cultivated land is sown by crops of corn, cotton and soybeans. Cultures remained intact and could develop freely, not suppressed by weeds. Example 8, In the greenhouse, the above plants are treated with cyclohexylmethylamide 4-methyl-1,2, 3-tia diazole-5-carboxylic acid at 1 kg of effective substance per hectare. For this purpose, the equipment is sprayed uniformly on spreads in the form of an emulsion in 500 liters of water per hectare. The results show that the cultivated plants, rice and maize remain intact while the most important weeds are destroyed. A similar effect also has the following compounds: N-ethyl-M-benzylamide-4-methyl-1, 2, 3-thiadia. Ash-5-carboxylic acid, N-benzyl-N-isopropylamide-4-methyl-1, 2, 3-tia d1} azole-5-carboxylic acid, N-ben Ben-zyla-M-butylamide 4-methyl-1,2,3-thiadiazole - $ - carboxylic acid, .3-methyl Lymethyl 4-methyl-1,2, 3-thiadiazole-B-carboxylic acid, 2 (naphthylmethyl) -amide-4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid, 3,5-dimethylbenzyl-amide 4-methyl-1,2,3- thiadiazole-5-carboxylic acid, (4-tert-butylbenzyl) -amnd-4-methyl-1,2, 3-thiadiazole-5-carboxylic acid. Example E. In the greenhouse, the plants before the shoots are treated with the proposed means (Table 2, 3} with the consumption norms of 1 kg of the effective substance per hectare. For this purpose, means are used in the form of a suspension with 500 liters of gas per hectare, evenly spread on the ground). The results show that the proposed remedies destroy a large number of plant weeds, while the important crops — corn and cotton — remain intact. EXAMPLE 10 Cotton plants grown in flower pots at the flower development stage buds are treated with the effective substances indicated in Table 4 at the indicated dosage (the experiments were repeated 4 times.) The amount of water used was 500 liters per hectare. After a few days, the percentage of the leaves was set as a percentage. Table 4 shows the superiority of the proposed compounds in relation to the known.
    4-Methyl-1,2,3-thiadiazole-5-carboxylic
    O 413 acid, 3
    00 00
    Oh oh
    0313 03
    About 4
    0304
    0.003 03 11 03
    About 20,000 00 00
    O 0.01-00 23 03
    O 1 02 00 02 03 781640, 1.T2TzTGG5TbTG 3-1 etla1Hln-methyl-1,2,3-thiadiazole-5-carboxylic acid 04.04 04 04 4-Methylanilide 4-methyl-1, 2,3-thiadiazole- 5-carboxylic acid 00 00 00 4-Fluoro-anilide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 040204 3-Trifluoromethyl anilide 4-methyl-1,2,3-..-tyadiazole-5-carboxylic acid O 3 O 003 N-Benzyl. -N-2-ppinylamide-4-methyl-. -1,2,3-thiadiazole-5-carboxylic acid 100203 4-chloroanilide-4-methyl-1, 2,3-thiadia-3ol-5-carboxylic acid000001 3,5-dichloroanilide 4-methyl-1,2,3-thia- . diazol-5-carboxylic acidO 1 O OO 1 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid benzylamide 4 23 33 4-methyl-1,2,3-tyadiazole 5-carboxylic acid 4-chlorobenzylamide 44 43 44 - Xpor-6-methylanilide-4-methyl-1 2, 3-thiadiazole-5-carboxylic acid 32 32 00 2,6-Dichloroyl-nitz 4-methyl-1,2,3-thiadiazole-5-carboxylic acid 1 4 2 302 Diethylamide 4 -methyl-1, 2,3-thiadiazole-5-carboxylic acid 00 0100 2-Pyridylmethyl. amide-4-methyl-1,2,3-. -thiadiazole-5-carboxylic acid O 1 O 110 18 Continued table. l 1ГГГо ГГТГ2 1ГГГЛГ5Т1б 1Г --J - i-J 00 0002 1133 О 200 00 00 01. About About About .0 About About 12 03 About About 00 About 01 About About 3. 00 О 3 00 00 04 0 00101 00 01 00.0, 1 О 1 О 00 1. 2 3 3331 33 34, 34322 43 44. 0 000 00 00 23 О .111 00 О 1 2. 0100 00 00 00 010 00 О О О О О О 19816401. 1 | 2 | 3 | 4 | 51b | 7 2-Chlorbeneyl amide 4 methyl-1,2,3-thiadiaeol-3-carboxylic acid 22 32 21 (Cyclohexylmethyl) amide-4-methyl-1, 2, 3-thiadiazole-3 carbonic acids 44 44 44 3,4-methylenedioxybenzylamide 4-methyl-1, 2,3-thadiazole-5-carboxylic acid 2121000 2,4-dichlorobenzylamide 4-methyl-1,2,3-thiadiaeol-5-carboxylic acid 0300 02 3,4- Dichlorobeneyl-4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 01 00 01 3-Chlorobenzylamide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid 01 00 01 2-Methoxy-benzylamide-4-methyl -1, 2,3-thiadiazole-5-carboxylic acid00 00 10 4-Fluorobenzylamide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid4444 44 4-methyl-1,2,3-tya 4-methylbenzylamide. diazap-5-carboxylic acid31 33 10 2-Fluorobenzylamide. 4-methyl-1,2,3-thiadna-3ol-5-carboxylic acid 44 4444 Cyclohexylamide 4-methyl-1,2,3-thiadiazole-5-car-. bonic acid44 43 44 Cyclooctylamide 4 methyl-1, 2,3-thia-. diazole-5-carboxylic acid 24 4 3 .2 f. 20 Continued table. 1 lo | ll I 12 | l3 I 14 | l5 j 1bM 8 | 91lOlll I 12 | l3 I 14 | 15 I I6 | l7 012000 4131 4 4 4242 44 44. 0111001111 O O 0000 11 04. 0100 01 00 01 О 1 01 01 00 01 о о 000000 00. 3 4 42 31-44 .44 1 2 200031 32 4 4 44 20 44 44 3 33 33 32 44 44 2 332 22 32 13 2181640 1 IjTiI Cyclo-hyptypamine 4-methyl 1,2,3-thiadiazo-3-carboxylic acid 44 4344 Cfclope 11 tnla | "| D. 4-methyl-1,2,3-thiad azo-5-carboxylic acid 121001 Cyclbpropylamide 4-mvtil-1; 2,3-tnadiazo "-5-carboxylic acid; 11 10 01 Butyl" d 4-methyl-1, 2.3 α-tigschiaeol-5-carbonic acid 33 21-43 {2-Furfur1) -a id-4-methyl-1, 2.3 thiadiazop-b-carboxylic acid 00 00 01 (1-Phenyl9-methyl) -amide-4-methyl-1, 2, 3-thiadiazole-5-kapboxylic acid00 00 01 Cyclopropylmethyldad 4-metsh1-1,2,3-thiadiazole-5-carboxylic acid 01 00 03 Morpholinoamide-4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 1000 1000 Piperidinogsid-4-methyl-1,2,3thiadiazal-5-carboxylic acid 00 00 00 H-Benzyl 4-methyl-1, 2,3-thia-. diazol-5-carboxylic acid 00 00 01 4-methyl propyl amide, 2,3-thiadiaz. ap-5-carboxylic acid 00 00 00 4-methyl-1 isopropylamide, 2,3-tiadea-5-carboxylic acid 00 00 00 Cyclohexylmethyl ester 4 -methyl-1, 2 3-thiadia; ash-5-carboxylic acid00 0301 22 Continuation of the pressure .. 1 2 33. 2 203331 0000.001000. 0/0 01 00 0000 2 3110011 2 (-2 0001 00 00 {). .. 00 00 O 100 0000: 00 0 O 00 00 00 00 0.0 00 30 00 00 O O 03 00 0000, O O 03 0000 00 O 1 01 00-00 00, O 1 010001 00 23816401 11 G I 1 1 4 -Methyl-1,2, 3-thiadiazol-5 yl-morpholinoketone 00 00 01 4-Chlorobenzyl ester 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid.02 03 03 Benzyl 4-methyl-1,2 , 3-thiadiazole-5-carboxylic acid01. 03 02 Amide 4-methyl-1,2, 3-thiadiazole-5-carboxylic acid 01 01 00 2-Methylcyclohexylamide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 44 44 44 Z.-Methylcyclohexylamide 4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid 44 44 44 4-Methylcyclohexylamide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid22 42 20 Tesgrahydrofurfuryl amide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 442232 Cycloheptylmethylamide 4-methyl-1,2,3-thiadiazole-5-carboxylic acid 4444 44 Cyclohexylmethylamide 4-PROPYL-1,2, 3-thiadiazap-5-carboxylic acid 02 00 00 1,2, 3-Trimethylpropylamide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid loty020200 Feniletilamid 2-4-methyl-1,2,3-thiadiazole-5-carboxylic kisloty020202 Continued Table 24. 1 I lajia lulls leli O O 01 01 00 01 O 2 01 00 01 01 O 2 02 00 01 01 O O 00 00 00 00. 00 42 20 44 44 О О 44 44 44 44 00 20 00 22 24 0000003221 О О 44 44 44 44 0000 00 00 00 0000000000 0000000000 2581640 i 2ТШ1ППТШ Cyclohexylmethyl-. 4-ethyl-1,2,3-thiadiazole-5-carboxylic acid amide 34 42 44 4-ethyl-1,2,3-thiadiazole-5-carboxylic acid ethyl ester00 0011 4-Propyl 1,2,3-thiadiazole- 5-carboxylic acid00 33 00 (4-Methylbenzyl) -amide 4-propyl-1, 2,3-thiadiazole-5-carboxylic acid 11 OOOO (4-Chlorobenzyl) -amide-4-propyl-, 2,3-thiadiazole - - karbrnovoy. Acids 11 0000 (4-Fluorobenzyl) -amide-4-propyl-1 ,, th, 3-thiadiazole-5-carboxylic acid 1100 00 (2,4-Dichlorobenzylamide) 4-propyl-1, 2,3-thiadiazole 5-carboxylic acid 110000 4-Propyl-1,2,3-thiadiazole-5-carboxylic acid cyclohexylamide 11 00 00 2-Methylcyclohexylamide 4-propyl-1, 2,3-thiadiazole-5-carboxylic acid 11 0000 2-Methylcyclohexylamide 4-propyl-1, 2, 3-thiadiazole-5-carboxylic acid 1100 00 3-Methylcyclohexylamide 4-propyl 1,2,3-thiadiazole-5-carboxylic acid11 00 00 4-Methylcyclohexylamide 4-propyl-1, 2,3-thiadiazole-5-carboxylic acid 11 0011 26 Continued table. one --.--. About 2 0000 02 02. O O 00 00 00 00. 0 О 00 00 00 00 О 00 00 00 00 О 00000 00 00 О О 00 00 00 00 0000000000 00 00 00 00 00 0000 0000 00. About 000 00 0000. . О О 00 00 00 00 00 00 0000 00 278164 11 2 Гз 1 4 Гз 1 6 Г ----- i. ---- ..- | -, - 1 J1-J-L ™ (Tsi KLOOKT ilmet il ) -ami d-4-prop pi l-1, 2,3-thiadiaeol-5-carboxylic acid33 00 00 (Cycloheptyl) -amide-4-propyl-l, 2, 3-thiadiaerl-5-carboxylic acid 331100 (1, 2-Diphenylethyl) -amide-4-methyl-1g 2, 3-thiadiazole-5-carboxylic acid 00 00 00 N-2 (cyanoethyl) benzyl-Jamide-4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid 110000 1 - (4-Fluorophenyl) -ethylZ-amide-4-methyl-l, 2, 3-thiadiazole-5-carboxylic acid 440000 (N-methylcyclohexylmethyl) -amide-4-methyl-1, 2.3 thiadiazole-5-carboxylic acids 44 44 44 3-hydroxyanilide 4-methyl-1, 2,3-thiadiazole-5-carboxylic acid 11 00 00 ( 1-Hydroxy-cyclohexylmethyl) -amide-4-methyl-1, 2,3-thiadiazole-5-carboxylic acid444444 4-methyl-1,2,3-thiadiazole-5-carboxylic acid phenyl ester -2 -2 -1 ( 1,3-Dimethylbutyl) amide-4-methyl-1, 2,3-thiadiazole-5-carboxylic acid-3-2-2 (3-Methylbutyl) -amide 4-methyl-1,2, 3-thiadiazole-5 -carboxylic acid 44 44 44 (2-Dimethylaminoethyl) -amide-4-methyl-1, 2, 3-thiadiazole-5-carboxylic acid - 28 Continued table. I 8 G 9 Gyutp ri2Tl3 GGBB L ----, - J14 .. O 00 000000 0000000000 O 6 00 00 00 22 0000000000. 0011000044 О 2 00 00 00 02 О О 00 00 00 00 443434343 -1 -1 -2 -3-3-0-0-3 l,, -, -, ii l i 4 4 32 32 41 --.-- --- 3-Phenoxybenzyl ester 4-methyl1,2, 3-3-thiadiazole-5-carboxylic acid
    3-methylcarbamoyloxyanilide-4-methyl-1, 2,3-thiadiazole-5-carboxylic acid
    (3,3-Dimethylbutyl) -amide-4-methyl-1, 2,3-thiadiazole-5-carboxy acid, 4
    3 32 11 41 42
    4 4
    4 4
    sch
    l tf
    to
     Choi "
    "41
    4-Methyl-1,2,3-thiadiaeol-5-carboxylic acid (cyclohexylmethyl) -amide. ,
    4-Fluorobenzylamine-4-methyl-1, 2,3-thiadiaeol-5-carboxylic
    Compounds
    The proposed Cyclohexylmethyl amide 4-methyl-1,2,3-thiadiazole-5-carboxy Formula of the invention. A method for producing 1,2, 3-thiadiazole-5-carboxylic acid derivatives of general formula a. where R - plp alkpl i l - - hydrogen or alkyl with "-C-, X residue -OR2 or -NCn |; Rj hydrogen alkyl, cyclohexylmethyl, benzyl, zyl, chlorbeisyl, phenoxybenzyl, phenyl, chlorophenyl, dichlorophenyl, Rj hydrogen, alkyl C | -C, cyanmethyl, cyan ethyl, propinyl, benzyl, phenyl, R4 - hydrogen, alkyl, ethoxyethyl, diethoxy Teal, Dime tilami Noetus, dimetilash NAAL saws, ethoxycarbonylmethyl, propenyl, dietilpropinil, cycloalkyl Cj-Cg, methylcyclohexyl, ethynylcyclohexyl, cycloalkylmethyl having from 3 to carbon 8 atoms in the ring cycloalkyl, gidroksitsiklogeksilmetil, benzyl, alkylbenzyl having from 1 to 4 Table 3
    J
    "Jf- jf 10101000
    Table 4
    Effective substance, kg / ha
    Defolitsi , tvtrahydrofuryl pyridylmethyl, piperidino morflino, R and R, together with the nitrogen atom, represent the morpholine pipesmidine or pyrrolidine group, consisting in that the acid chloride 1,2, H-t iadiazole-5-carboxylic acid of formula. -L flT where R2 has the indicated values, is subjected to a chemical reaction with a compound of the general formula Ml HX, where X has the specified values, at a temperature of 3581640136
    pe from room to room in the environment of the organization- 1. vigand Hilgeta. Methods of expingential solvent and in the presence of in organic chemistry. M.,
    in the acid and associated reagent. Chemistry, 1968, about. 349, 431.
    Sources of information taken into account in the examination 2. US Patent I 2,954,407.
    权利要求:
    Claims (1)
    [1]
    Claim
    The method of obtaining derivatives of 1,2, 3-thiadiaol-5-carboxylic acid of the General formula
    41)>
    Η 0 where R 4 is hydrogen or C ^ -C alkyl , X residue —OR 2 or R a — hydrogen alkyl Qj-Cj, cyclohexylmethyl, ben-, zyl, chlorobenzyl, phenoxybenzyl, phenyl, chlorophenyl, dichlorophenyl, R 3 hydrogen, alkyl C ^ -C ^, cyanmethyl, cyanethyl, propynyl, benzyl, phenyl, R4 - hydrogen, alkyl C 4 -Cg, ethoxyethyl, diethoxyethyl, dimethyl noethyl, nopropyl dimethyl, ethoxycarbonylmethyl, propenyl, diethylpropynyl, cycloalkyl Cj-Cg, methylcyclohexyl, ethylcyclohexyl, cycloalkyl, cycloalkyl carbon atoms in the cycloalkyl ring, hydroxycyclohexylmethyl, benzyl, alkylbenzyl containing from 1 to 4 atoms of 50 carbon in alkyl chain dimetilbe'nzil, methoxybenzyl, methylenedioxybenzyl, halobenzyl, dichlorobenzyl, phenylethyl, diphenylethyl, ftorfeniletil, phenylpropyl, naphthylmethyl, phenyl, methylphenyl, dimethylphenyl, halophenyl, chloromethylphenyl, dichlorophenyl, trifluoromethylphenyl, nitrophenyl, hydroxyphenyl, metilkarbamoiloksifenil, furfuryl, tetrahydrofuryl pyridylmethyl, piperidino morphlino, R 3 and R 4 together with a nitrogen atom represent a morpholine piperidine or pyrrolidine group, which consists in the fact that the acid chloride of 1,2, 3-thiadiazole-5-carboxylic acid of the formula μ - meaning: compound X of the name 65, is reacted with a general formula 111 HX,
    It is as defined, at temperatures higher by 10 C to room e in an organic solvent and in the presence kislotosvyazyvakadego reagent.
    类似技术:
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    同族专利:
    公开号 | 公开日
    GB2001623A|1979-02-07|
    DE2728523C2|1986-02-27|
    ES471078A1|1979-10-01|
    FI64361B|1983-07-29|
    FR2395263B1|1984-04-27|
    DE2728523A1|1979-01-11|
    FI781926A|1978-12-24|
    ZA783615B|1979-06-27|
    IN148754B|1981-06-06|
    PT68208A|1978-07-01|
    IL54930A|1983-03-31|
    PL110342B1|1980-07-31|
    BG29864A3|1981-02-16|
    IE781241L|1978-12-23|
    DD137317A5|1979-08-29|
    DK284078A|1978-12-24|
    IL54930D0|1978-08-31|
    AU3737478A|1980-01-03|
    BR7803932A|1979-02-28|
    GB2001623B|1982-03-03|
    IT1096813B|1985-08-26|
    NO782175L|1978-12-28|
    YU40335B|1985-12-31|
    BE868417A|1978-12-27|
    RO75256A|1980-11-30|
    IT7824835D0|1978-06-22|
    JPS549272A|1979-01-24|
    HU180986B|1983-05-30|
    AU523321B2|1982-07-22|
    NL7805470A|1978-12-28|
    CH636092A5|1983-05-13|
    MX5582E|1983-10-27|
    US4177054A|1979-12-04|
    EG13412A|1982-06-30|
    IE47000B1|1983-11-30|
    SE7805723L|1978-12-24|
    PL207788A1|1979-03-12|
    NO147987C|1983-07-20|
    SE429861B|1983-10-03|
    ATA445578A|1980-01-15|
    AT358323B|1980-09-10|
    NZ187506A|1979-12-11|
    CA1096872A|1981-03-03|
    YU127478A|1983-01-21|
    NO147987B|1983-04-11|
    LU79854A1|1978-12-07|
    FR2395263A1|1979-01-19|
    AR217850A1|1980-04-30|
    SU733503A3|1980-05-05|
    TR20600A|1982-02-18|
    PH14496A|1981-08-14|
    FI64361C|1983-11-10|
    CS200159B2|1980-08-29|
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    申请号 | 申请日 | 专利标题
    DE2728523A|DE2728523C2|1977-06-23|1977-06-23|4-Methyl-1,2,3-thiadiazole-5-carboxylic acidamide, agents having a herbicidal and growth-regulating action, containing this compound and a process for its preparation|
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