The method of producing thiazolecarboxamide

 

(57) Abstract:

Usage: new derivatives of thiazolecarboxamide exhibit fungicidal activity and can be used in agriculture. The inventive thiazolecarboxamide be obtained by interaction between the methyl ether of methylenedioxyphenol acid with 2-ethyl(2, 4-betasol)-4-yl-2-(S)-fluoro-propanoic acid. table 1.

The invention relates to the synthesis of new derivatives of thiazolecarboxamide, in particular, relates to a method of obtaining compounds of General formula I:

R

(I) where R1and R2the same or different hydrogen atom, an alkyl radical, thiazolyl.

and double bonds have an E or Z configuration or a mixture of E and Z configurations.

In the definition of the various substituents, preferably alkyl radicals methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secondary butyl or tertbutyl.

The proposed method differs from the known fact that the compound of formula II:

R (II) where R1and R2have the specified values, or a functional derivative of this compound is subjected to interaction with the compound of the formula III:

(III) where lc1the alkyl radical, sodiu means remove the rest of the alcohol l1IT to obtain the compounds of formula I:

R

I

In a preferred embodiment of the proposed method used the functional derivative of the acid (II) is an acid chloride. The removal of residual alcohol lc1-OH is conducted by heating in an acidic medium, for example, in the presence of para-toluensulfonyl,

Used as initial products of the compounds of formula II can be obtained as described below in the experimental part, these products are new and are the subject of the invention. Obtaining compounds of formula III, which are also used as starting materials, are known. The compounds of formula IV obtained during the execution of the proposed method, are new and are thus the subject of invention.

The compounds of formula I exhibit interesting fungicidal properties, which can be used for protection against pathogenic fungi, plant protection, protection of the premises or animals. These properties can also be used for hygiene purposes of medicine and veterinary medicine.

Proposed connections allow you to fight against many phytopathogenic fungi, in particular against risypne graminis, Sphaerotheca macularis, Sphaerotheca fuliginea, Podosphaera leucotricha, Uncinula necatortis cinerea, Alternaria spp. Venturia inaequalis, Plasmopara viticila, Bremia lactucae, Peronospora. spp. Pseudoperonospora humuli, Pseudoperonospora cubensis, Phytophthora spp. infestans, Phytophthora spp. hanatephorus cucumeris, Rhizeoctonia spp. and also against fungi or yeast, health-related people, such as Candida albicans or rychophyton spp. Thus, the compounds of formula can be used for preparing fungicidal compositions containing as an active start, at least one compound of formula I.

The compounds of the proposed method are prepared in the usual ways agrochemical industry. These compounds may be in the form of powders, granules, suspensions, emulsions, solutions or other preparations commonly used in such cases.

In addition to acting beginning, these formulations usually contain a carrier and/or ionic or non-ionic surfactant which enables uniform dispersion of the constituent substances of the mixture. Used carrier may be a liquid, such as water, alcohol, hydrocarbons or other organic solvents, mineral, animal or vegetable oil, powder, such as talc, clay, silicates, diatomaceous earth or solid combustible substance, the composition can also contain one or more other insecticidal or acareedrach of creds> Stage A. Methyl ether [2'-ethyl(2,4'-betasol)-4-yl]-2-fluorine(F)propanolol acid.

The solution to 5.56 g of lithium bromide in 55 cm3of tetrahydrofuran, cooled to -30aboutC, add 4.5 cm3Diisopropylamine. Cooled to -60aboutAnd add, not exceeding -55aboutC, 4 g [2'-ethyl(2,4'-betasol)-4-yl]carbaldehyde and is 5.18 g of methyl ester diethylphosphonate-ethanol acid in 50 cm3tetrahydrofuran (THF). Stirred for 1 h at -60aboutWith, and then poured to 2 N. the solution of hydrochloric acid. Sucked off and dissolving the product in chloroform, dried, filtered and distilled to dryness. Get a 5.1 g of the target product. So pl. 140aboutC.

IR-spectrum (l3on RE 580): 0 1731 cm-1WITH OCH3with CH31438 cm-1C=C 1668 cm-1C=N 1652 cm-1Heteroaromatic compound 1540 cm-1< / BR>
1500 cm-1< / BR>
Stage b [2'-ethyl(2,4'-betasol)4-yl]2-(S)-fluoro-Papanova acid.

Stirred for 16 h at 20/25aboutWith 5.1 g of product obtained above in stage A, 100 cm3methanol and 20 cm31 N. sodium hydroxide solution. Washed with methylene chloride, acidified aqueous layer was then extracted with methylene chloride, R> OH the region 3000 to 2000 cm-1With=0, the complex 1730 cm-1C=C 1642 cm-1C=N 1635 cm-1heteroaromatic compound.

P R I m e R 1. Methyl ester 2-{N-[3-[2'-ethyl-(2,4'-betasol)-4-yl]-1-oxo-2-(Z)-fluoro-propenyl]methylamino-3-methoxy(Z)propanolol acid.

Stage A: methyl ester of 2-{N-[3-[2'-ethyl(2,4'-betasol)4-yl]-2-(Z)-fluoro-1-oxopropyl]methylamino}-33-dimethoxy - benovoy acid.

Heated to reflux for 1 h 30 min 4.7 product obtained in stage B of preparation 1, and 50 cm3chloride tiomila. Again bring to 20/25aboutWith and remove excess chloride tiomila. Absorb 50 cm3chloroform and added to this solution under stirring at 20/25aboutTo a mixture of 7,09 methyl ether of methylenedioxyphenol acid and 100 cm3the chloroform. Stirred for 30 min, evaporated to dryness and chromatographic the residue on silica (eluant hexane ethyl ester acetic acid 1:1). Obtain 3.2 g of the target product.

IR-spectrum (l3on RE 580):=0 complex 1740 cm-1S-OMe 1439 cm-1O C= 0 + C=C 1660 cm-1< / BR>
1649 cm-1< / BR>
1538 cm-1Conjugated system 1498 cm-1CH32840 cm-1< / BR>
Stage b Methyl ester 2-{N-[3-"ptx2">

Heated to reflux for 1 h 30 min, removing the formed methanol, a mixture of 3.2 g of the obtained product in stage a and 50 cm3toluene with 30 mg of paratoluenesulfonyl. Poured into water, extracted with methylene chloride, dried, filtered and brought to dryness. The remainder chromatographic on silica (eluant hexane ethyl ester acetic acid 1:1) and gain of 1.76 g of the target product, So pl. 99aboutC.

Analysis17H18N3O4S2F

Calculated With 49,62; N To 4.41; N Of 10.21; S 15,58; F 4,62.

Found, For 49.8; H 4,4; N 9,9; S 15,4; F 4,5. Preparation 2 3-(4-thiazolyl)-2-fluoro-2-(E)-Papanova acid.

Stage And Methyl ester 2-fluoro-3-(4-thiazolyl)-2-propanolol acid, isomer E.

Act as in stage a of preparation 1, but on the basis of 6 g of 4-formulate, eating and 15.3 g of methyl ester diethylphosphonoacetate acid. After chromatography on silica (eluant hexane ethyl ester acetic acid 9:1) obtain 6.4 g of the target product used in this form in the next stage.

MK-range: C=0 1734 cm-1-C=C - 1438 cm-1Conjugated system 1656 cm-1CH3belonging to SOON31440 cm-1< / BR>
Stage B: 3-(4-thiazolyl)-2-fluoro-2-Papanova of product. Gain of 5.2 g of the target product.

IR spectrum (liquid paraffin on Nicollette) the Total absorption OH/NH-C=C - 1641 cm-1C=0 complex: 1712 cm-1Conjugated system 1575 cm-1< / BR>
1551 cm-1< / BR>
P R I m m e R 2: Methyl ester (Z,Z)-2-[(2-fluoro-1-oxo-3-(4-thiazolyl)2-propenyl)N-methylamino]3 - methoxy-2-propanolol acid.

Stage A. the Methylene ether of 2-[N-[3-(4-thiazolyl)-1-oxo-2-(Z)-fluoro-propenyl]methylamino]3,3-dimethoxypropionate acid.

Stage A. Obtain the acid chloride.

Stirred with reflux for 2 h 30 min of 5.2 g of the product obtained in stage B of preparation 2, and 20 cm3chloride tiomila. Evaporated to dryness, redistilled hexane and obtain 6.6 g of the acid chloride.

Stage B. Condensation.

At room temperature, stirred for 15 g of the hydrochloride of the methyl ether methylamino dimethoxy propanoic acid 150 cm3chloroform and 13.1 g of sodium bicarbonate. After the evolution of gas added sodium sulfate and filtered. To the resulting solution was added to 13.1 g of sodium bicarbonate and then for 30 min was added a solution of 6.6 g of the acid chloride obtained in stage a, 100 cm3the chloroform. Stirred for 16 h at room temperature, and then mililitres and evaporated to dryness. The remainder chromatographic on silica (eluant hexane ethyl ester acetic acid 4:6) and obtain 5.9 g of the target product.

IR-spectrum (HCl3on RE 580):

C=0 type-With-och3unpaired 1739 cm-1< / BR>
tertiary amide + -C=C - 1639 cm-1< / BR>
CH31439 cm-1< / BR>
Stage b Methyl ester (Z,Z)2-[(2-fluoro-1-oxo-3-(4-thiazolyl)-2-propenyl)N-methylamino]-3-methoxy-2-p romanovas acid.

When 130aboutWith stirred 5 h 30 min, turning the formed methanol, a mixture of 5.9 g of the product obtained in stage a, with 60 cm3toluene and 60 mg paratoluenesulfonyl. After 1 h, add 200 mg of para-toluenesulfonic acid. After 16 h of rest was added 600 mg of paratoluenesulfonyl and stirred for 1 hour and 30 minutes with reflux, driving the formed methanol. Cooled, washed with water and evaporated to dryness under reduced pressure. Chromatographic on silica (eluant methylene chloride: ethyl ester acetic acid 1:1) and obtain 1.55 g of the target product, which is dissolved in methylene chloride, filtered and brought to dryness under reduced pressure. Obtain 1.1 g of the target product.

IR-spectrum (l3on RE 580): C=0, the region of conjugate complex ester 171SUP>-1< / BR>
1630 cm-1< / BR>
Analysis: WITH12H12FN2O4S

Calculated With 47,99; N 4,36; F 6,33; N Was 9.33; S Is 10.68.

Found, With 47,7 N 4,3; F 6.0; N 9,1; S 10,4.

P R I m e R 3. On the basis of relevant connections and working in this procedure, obtain methyl ester (Z,E)of 3-methoxy-2-(methyl)2-fluoro-1-oxo-3-[2-(trifluoromethyl)4-thiazolyl] -2-propenyl-(amino)-2-propanolol acid.

Biological fungicide activity

a) Experience trytis cinerea in the vineyard.

Young seedlings of the vineyard, derived from cuttings (sort Grenache N, clone 70) are grown in the greenhouse (day temperature 30aboutTemperatures at night 25aboutWith the mixture of earth /topsoil/sand/ 1/3-1/3-1/3), two days before the experiment, the seedlings are transferred into the chamber cultivation (the same conditions of temperature, humidity 60% during the day, 80% at night). The product dissolves in the matrix And" at a concentration of 500 thousand hours before use. Treatment is performed by spraying the solution on the leaves to a maximum retention. Spores of Botrytis cinerea suspension in dilute carrot juice, 50000 dispute ml. Contamination is the deposition of a suspension of spores in the form of drops (20 Ál) on abaxial leaf surface. In precautionary experience processing proizvodid is explained above. The countdown is nine days after infection by measuring dead surfaces. The effectiveness of the product is calculated relative to the untreated control sample.

b) Experience on Plasmopara viticola

Plants are the same as were used in experiment a), and bred in the same conditions. The processing is the same as in experiment a). The infection is produced by suspension zoosporangium inside host Plasmopara viticola, is taken directly to the experience (50000 zoosporangium inside host per ml). Drops of the suspension (20 Ál) was deposited on abaxial side of leaves. Then the seedlings incubated 24 h in a saturated humidity atmosphere, and then re-adjusted to the humidity chamber cultivation (60% day, 80% at night).

The countdown is ten days after infection by measuring the development of processes conidiophore on abaxial leaf surface. The effectiveness of the product is calculated relative to the untreated control sample.

C) Experience rysiphe graminis horde.

Grains of barley (variety Presslon) leave for germination on a mixture of land-soil-sand /1/3-1/3-1/3/ and grown in the greenhouse. The products are dissolved in the matrix And" directly before the experiment at a concentration of 500 hours per thousand. Treatment is performed by spraying the solution on plants is the processing. Seedlings kept in air-conditioned room (temperature day 23aboutTemperatures at night 18aboutC), within seven days after infection measure the distribution of skolachivaniya conline on the first and second leaf of each seedling. The effectiveness of the product is considered in relation to the untreated control sample.

g) Experience of Gaeumannomyces graminis tritici

The preparation of vaccines. 200 g of autoclaved grain oats infect Gaeumannomyces graminis tritici and retain for five weeks at a temperature in the 22aboutAnd in the dark. Vaccination is then dried into a powder and store in this form. On the day of the experience flushed and damp Vermiculite infect inoculation (1 wt. vaccinations) and distribute the boxes for growing (100 g per box). The layer thickness of 2 cm uninfected Vermiculite is placed on the surface of the boxes.

Grain grain bread (sort ppelle) sow in this upper layer. The analyzed products are dissolved in the matrix And" at a concentration of 50 hours per thousand. The treatment is carried out by pouring each box 30 ml of product. The boxes are kept in the premises for cultivation (temperature day 21aboutC, night temperature 16aboutC). The mass of the aerial parts and root portions of each seedling was measured three weeks after probochnoi control sample.

d) the Experience of Puccinia recondita tritici

Grain grain bread (sort of Festival germinated in a mixture of earth-soil-sand/1/3, 1/3, 1/3/. The seedlings grown in the greenhouse. The products are dissolved in the matrix And" immediately before the experience, at a concentration of 500 hours per thousand. The treatment is carried out by spraying the solution of the investigated product on the seedlings of corn bread at the age of 9 days, up to a maximum deduction. Infection uredospore Puccinia recondita tritici lead on the next day after treatment. Seedlings kept in air-conditioned room (temperature day 22aboutTemperatures of the night 18aboutC). Seven days after infection measure the density of spores on the first two leaves of each seedling. The effectiveness of the product is calculated relative to the untreated control sample.

The results are summarized in table.

The METHOD of producing THIAZOLECARBOXAMIDE General formula

< / BR>
where R1and R2the same or different, hydrogen, alkyl, thiazolyl, and the double bond has - or Z-configuration or a mixture of e - and Z-configurations

characterized in that the compound of General formula

< / BR>
where R1and R2have the specified values,

or a functional derivative of this compound machining
to obtain compounds of General formula

< / BR>
where R1, R2and Alk have the above values,

which is then exposed to the remove remaining alcohol Alk-OH and share if necessary for the isomers.

 

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