The method of obtaining ethyl--2-dichloro-5-[4-(deformity)-4,5 - dihydro-3-methyl-5-oxo-1h-1,2,4-tr eazol-1-yl]-4 - ferbinteanu

 

(57) Abstract:

Describes an improved method of obtaining a known herbicide - ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl] -4-ferbinteanu by diazotization of 4-deformity-4,5-dihydro-3-methyl-5-oxo-1-(5-amino-2-fluoro-4-chlorophenyl)-1H-1,2,4-triazole and arilirovaniya of acrylate obtained diazonium salt, the diazotization and atilirovanie carried out simultaneously, to the derived 1,2,4-triazole in 10 to 30 equivalents of acetone successively added 0.05 to 0.5 equivalents of copper chloride (I), hydrochloric acid, acrylate and sodium nitrite. 2 C. p. F.-ly, 2 tab.

This invention relates to an improved method of carrying out the last stage. receiving herbicide ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4 triazole-1-yl] -4-ferbinteanu reaction of diazotization of Meerwein and arilirovaniya.

The herbicide, which has the following structure

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described and claimed in U.S. patent 5125958.

In normal practice, the reaction of diazotization of Meerwein and arilirovaniya carried out in two stages. First arylamine diasterous in aqueous solution, for example, nutritive.

In U.S. patent 5125958 the last stage of the receipt of the herbicide involves diazotization of the amine 4-deformity-4,5-dihydro-3-methyl-5-oxo-1-(5-amino-2-fluoro-4-chlorophenyl)-1H-1,2,4-triazole. However, it was later discovered that when he tried to diisocyanate this amine in aqueous solution, 2-persemester was lost due to hydrolysis to the corresponding phenol. In accordance with this diazotization described in this patent, spent two conventional stages, but in non-aqueous environment, with tert-butylnitrite as a source of nitrite. Diazotized amine was then added to the acrylate (atilirovanie) to obtain the target of the herbicide. Although this procedure is satisfactory for laboratory obtain in small quantities, it is unsatisfactory for large-scale production and commercial reception. Not only too limited supply of tert-butylnitrite, but getting on a large scale requires the handling of large quantities of diazocompounds - undesirable dangerous surgery.

Unexpectedly, it was found that in suitable conditions, diazotization and atilirovanie can be carried out simultaneously aqueous sodium nitrite without loss 2 of forsometimes and unexpectedly good is oops:

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As described above, in conventional practice, first get the diazonium salt and then add it to the connection that must be areliano. In the method according to this invention cleaners containing hydrochloride salt of the amine (A) diazotised with sodium nitrite in the presence of acrylate material, which must be allerban. Vasodilated (D) obtained by diazotization of the amine hydrochloride with sodium nitrite reacts with the acrylate in the presence of catalytic amounts of copper chloride (I). The reaction is carried out at low temperature in acetone. The use of acetone as a solvent allows the use of sodium nitrite in a minimum amount of water. Acetone also facilitates recycling of used as a catalyst of copper chloride (I). Another advantage of this method is the fact that the reaction of diazotization/arilirovaniya held at the same time, minimize the probability of a reaction product of diazotization with himself.

The method starts with obtaining the solution of amine And acetone, preferably in an atmosphere of inert gas, for example nitrogen. Acceptable ratio of acetone to amine is in the range from 10 to 30 equivalents of acetone to one equivalent is to remove any insoluble material, which may be present. To a solution of amine added under stirring catalyst arilirovaniya of Meerwein, for example, chloride, copper (I) or copper chloride (II), preferably the chloride copper (I), and again preferably in an atmosphere of inert gas stirring is continued throughout the reaction).

In the method according to the present invention is set to the number of copper chloride (I). If it is used too low, the reaction proceeds more slowly and the yield of the final product below. Too much chloride copper (I) in the reaction mixture leads to the dechlorination end product. Therefore, an acceptable ratio of copper chloride (I) to amine is in the range from 0.05 to 1.0 equivalent of chloride of copper (I) one equivalent of amine, preferably from 0.1 to 0.15 equivalent to one equivalent. The reaction mixture is then cooled to a temperature below 0oWith, preferably to about -10oWith, and an amine salt is produced by adding concentrated hydrochloric acid or anhydrous hydrogen chloride, preferably anhydrous hydrogen chloride is injected below the surface of the reaction mixture. During the addition the reaction mixture was kept at a temperature of from -20oWith do min, preferably from about 45 to 90 minutes is set to the number of acrylate, which is then added to a suspension of amine salt. For optimal outputs in this way requires a large excess of ethyl acrylate. If the excess is reduced, the yield of the final product decreases. It was found that an acceptable ratio of acrylate to amine ranges from 5 to 20 equivalents of acrylate to one equivalent of the amine, preferably from 10 to 15 equivalents to one equivalent. The time required to add acrylate, relatively not important. However, the temperature of the reaction mixture is kept lower than 10oWith within just adding and regulate to some extent the addition of acrylate. The temperature of the reaction mixture is then brought to about 0oWith and to the reaction mixture an aqueous solution of sodium nitrite. This stage is a critical stage in the method of the present invention. Reaction of diazotization/arilirovaniya are at the same time.

During the stage of diazotization amount of water should remain minimal. A large amount of water causes hydrolysis of the diazo intermediate product, giving phenolic by-product. To minimize obnovlencev sodium nitrite to one equivalent of the amine, preferably from 1.4 to 1.7 equivalents to one equivalent. To maintain a minimum amount of water beneficial use for stage diazotization of concentrated aqueous solution of sodium nitrite. A saturated aqueous solution of sodium nitrite contains about 40% (wt. /Mac. ) of sodium nitrite. Acceptable concentration of an aqueous solution of sodium nitrite, therefore, is approximately 20 to 40% (wt. /Mac. ) sodium nitrite, preferably from 35 to 40% sodium nitrite. The temperature of the reaction mixture also important in optimizing the reaction of diazotization/arilirovaniya. Temperature above 10oTo increase the probability of formation of side product. Acceptable temperature range of the reaction mixture to optimize stage of the method is between -10 and 20oC, preferably from 0 to 10oC. the Speed of adding an aqueous solution of sodium nitrite is also important to optimize the output. High speed add in the method according to the present invention leads to lower outputs of the product. Optimal speed add requires approximately 1 to 6 hours, preferably from 2 to 3 p.m Adding an aqueous solution of sodium nitrite is carried out below the surface mixed reaction CME is, to complete the reaction. At this point receive the outputs of the crude product in the range of 80-88%. Product purity can be improved by washing, followed by distillation. During the stage of leaching temperature support from about -10 to 20oWith, preferably from 5 to 10oWith, and in the preferred sequence of washing the reaction mixture is washed first with dilute aqueous acid, for example 5% hydrochloric acid, then dilute aqueous base, such as 5% sodium hydroxide, and finally with a solution of sodium chloride. After completion of the stages of the leaching of volatile materials in the reaction mixture, i.e., acetone/acrylate, can be removed at a temperature in the reaction vessel 30 to 80oC, preferably from 40 to 65oC, under reduced pressure of 20 to 70 mm Hg, preferably from 45 to 55 mm Hg. Removal of volatile material is considered complete when the concentration of the acrylate below about 5%. It is known that under certain conditions, the acrylate is polymerized. As a precautionary measure to the system of the upper shoulder strap add antioxidant and inhibitor of free radicals. However, there is no evidence that in the reaction vessel during the reaction, statuetki product containing non-volatile material is the reaction product can distill in an evaporation apparatus with a short by passing the product or distillation apparatus with a flowing liquid film. To improve the efficiency of the process of distillation, the reaction product can be skipped (stage degassing) through distillation apparatus when the evaporator temperature from 100 to 140oC and a pressure of from 10 to 20 mm Hg, preferably from 120 to 130oC and a pressure of from 13 to 18 mm Hg to remove any remaining amount of the acrylate or other low-boiling materials. Degassed the reaction product can then pass once through evaporator unit when the evaporator temperature from 160 to 180oC and a pressure of from 1.0 to 5.0 mm Hg, preferably from 170 to 180oC and a pressure of from 1.0 to 2.0 mm Hg. Non-volatile material from the first run through the evaporating device, you can then skip the second time through evaporation apparatus when the evaporator temperature from 160 to 200oC and a pressure of from 0.03 to 1.0 mm Hg, preferably from 160 to 180oC and a pressure of from 0.03 to 0.5 mm Hg. The transmission rate through the evaporator apparatus will be determined by the size of the evaporator. It is clear that the conditions degasification and distillation will vary depending on the device. Operation in the preferred conditions gives a typical output in percent distilled ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl] -4-fluoro-benzoylpropionic high pressure).

Example 1

Getting ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl] -4-ferbinteanu, laboratory scale

Flask of polymer in 2 liters of a shirt provided with a thermometer, a tube for input of nitrogen, an output tube connected to the carbon trap (to minimize leakage smell of acrylate and a device consisting of a coated Teflon needle length 203.2 mm (8 inch) and larger diameter attached to the syringe 50 ml, which, in turn, is connected with the piston of the syringe. In a separate vessel 140,4 g (0.46 mol-1,0 EQ. ) 4-deformity-4,5-dihydro-3-methyl-5-oxo-1-(5-amino-2-fluoro-4-chlorophenyl)-1H-1,2,4-triazole are dissolved in 600 g (10,33 mol - 22.5 EQ. ) acetone. The solution is cooled to 0oC and filtered in a polymer flask. Under stirring a solution of triazole/acetone bubbled 56,2 g (1.54 mol - 3,4 EQ. ) anhydrous hydrogen chloride over a period of 15-20 minutes After addition was added to 6.1 g (0.06 mol - 0.13 EQ. ) chloride copper(I). With continued stirring, the reaction mixture was cooled to 0oC in nitrogen atmosphere and add 640,4 g (6,33 mol - 13,8 EQ. ) ethyl acetate. The reaction mixture was again cooled to 0oAnd add a solution of 48.1 g (0.69 mol, 1.5 EQ. ) of sodium nitrite dissolved in 88,1 agodnym hole of the needle below the surface of the reaction mixture. Fully the addition requires about 3.75 hours, then the reaction mixture was stirred for additional 45 min at 0oC. the Reaction is then quenched with 200 ml of water, after which the reaction mixture is stirred for about 15 minutes the Organic layer was separated and washed with one portion of each of 200 ml of aqueous 1N hydrochloric acid, 200 ml of water and a mixture of 1: 1 aqueous 5% sodium hydroxide and ethyl acetate, where each of the volumes of sodium hydroxide solution and ethyl acetate equal to the volume of the organic layer. The organic layer is then concentrated at 70oWith in a vacuum, getting 193.3 M. g (analysis to 84.6%, crude yield - 86,4%) ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl] -4-fluoro-benzoylpropionate. The concentrated product is passed through the distillation apparatus Pope with flowing liquid film size 50.8 mm (2 inch), 0,2322 m2(0,25 ft2) at 160 and 0.8 mm Hg to remove low-boiling impurities. Non-volatile material is passed a second time through the distillation apparatus with a flowing liquid film in 220oC/1 mm Hg for distillation product from high boiling impurities, getting 134.9 g (analysis - 92%, the yield of distilled product - 65,6%) ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl-5-oxo-1 H-1,2,4-triazole-1-yl] -4-ferbinteanu, scale pilot plant

In accordance with the following method has received several portions of the product. In the reactor 757 l (200 gallon) with a shirt load through pressure drop acetone, 207,472 kg (457,4 pound (3578,8 g-mol (7,89 lb-moles), 22 EQ. ), then 48,534 kg (107 pounds) (163,29 g-mol (0,36 lb-mole), 1,0 EQ. ) 98% 4-deformity-4,5-dihydro-3-methyl-oxo-1-(5-amino-2-fluoro-4-chlorophenyl)-1H-1,2,4-triazole. The mixture is stirred and optionally filtered at room temperature to remove solid impurities. The solution is to overload the reactor 757 l (200 gallon), stirred and blown off with nitrogen. To it then add 2,086 kg (4,6 pounds) (22,68 g-mol (0,05 lb-mol), 0.13 EQ. ) chloride copper(I). After complete addition, the mixture is cooled to approximately -10oCirculation of cold brine through the jacket of the reactor. The reactor is closed and the nitrogen purge is stopped. Then anhydrous hydrogen chloride, 14,832 kg (32,7 pounds) (408,23 g-mol (0,9 lb-mole), 2,5 EQ. ) bubbled below the surface of the reaction mixture at a rate of about 249,5 g (0,55 lb/min, while the temperature of the reaction mixture support between -10 and 10oC. Complete the addition requires about one hour. After complete addition, the reactor is opened for communication with atmospheric pressure. The temperature of reactio is. ethyl acrylate. After adding add 16,828 kg (37,1 pounds) (2195,4 g-mol (4,84 lb-moles, 1.5 EQ. ) of sodium nitrite in 31,298 kg (69 pounds) (1737,2 g-mol (3,83 lb-moles), 10.6 EQ. water at a rate of about 272,2 g (0,6 pound/min below the surface of the reaction mixture. The temperature of the reaction mixture support between 0 and 5oC. Complete the addition requires about three hours, after this time the reaction mixture is stirred for 30 minutes while the temperature of the reaction mixture support between 5 and 10oC, the reaction mixture was washed in turn 66,678 kg (147 pounds) of water, 66,587 kg (146,8 pounds) of aqueous 5% hydrochloric acid, 69,399 kg (153 pounds) of aqueous 5% sodium hydroxide and 68,038 kg (150 pounds) of water. The ethyl acetate and acetone is then removed from the reaction mixture by distillation at about 65oWith/50 mm Hg. To prevent polymerization of the distilled mixture of ethyl acetate and acetone stabilizing solution comprising of 81.6 g (0,18 pound) 4-methoxyphenol, to 81.6 g (0,18 pound fenotiazina and 25,401 kg (56 pounds) of toluene, which circulates through the condenser and distillate receiver. The temperature of the product residue is supported approximately at 45oWhen it salariat in the drum for future use. The yield of crude product, ethyl--2-dichloro-5[4-(deformity)-4,5-dihydro-is isano above, pooled. The product of combining passed through the distillation apparatus with a flowing liquid film first at low vacuum to remove low-boiling material (degassed), then twice under high vacuum to obtain the distilled product. Distillation in a distillation apparatus with a flowing liquid film using the conditions listed in the table. 1.

Percent of distilled ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro)-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl] -4-ferbinteanu is 65% (based on amount of starting amine), purity 91% (as determined using liquid chromatography high pressure).

Example 3

Getting ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl] -4-ferbinteanu, scale pilot plant

In accordance with the following methodology has received several portions of the product. The reactor 3785 l (1000 gallon) with face blown off with nitrogen and was charged to the reactor 231,331 kg (510,0 pounds) (775,7 g-mol (1,71 lb-moles), 1,0 EQ. ) 98% 4-deformity-4,5-dihydro-3-methyl-5-oxo-1-(5-amino-2-fluoro-4-chlorophenyl)-1H-1,2,4-triazole. It then downloads 9,979 kg (22,0 pounds) (99,79 g-mol (0,22 lb-mole), 0.13 EQ. ) chloride copper(I). The reactor is sealed and again rinsed AZ is l (37,57 lb-moles), 22,0 EQ). After complete addition, the mixture is stirred and cooled to a temperature of between -10 and 0oWith by circulating cold brine through the jacket of the reactor. Then anhydrous hydrogen chloride 70,669 kg (155,8 pounds) (1936,83 g-mol (4,27 lb-mole), 2,5 EQ. ) bubbled below the surface of the reaction mixture at a rate of about 1133,97 g (2.5 lb)/min, while the temperature of the reaction I support below 10oC. Adding anhydrous hydrogen chloride usually ends at time one to two hours. After completion of the feed of hydrogen chloride reactor open for communication with atmospheric pressure. The temperature of the reaction mixture is then adjusted to approximately 0oWith and into the reactor by means of the delivery piston pump load 1045,6 kg (2305,2 pounds) (10477,9 g-mol, (23,1 lb-moles), 13,5 EQ. ) acrylate. When you are finished adding loads below the surface of the reaction mixture 200,396 kg (441,8 pounds) water 40 wt. % (1161,2 g-mol (2,56 lb-mole), 1,5 EQ. ) solution of sodium nitrite at a rate of about 816,5 g (1,8 lbs)/min. and the Temperature of the reaction mixture support between 0 and 5oC. Complete the addition requires about four hours, after this time the reaction mixture is stirred for 30 minutes the Reaction is considered zainee than about 0.5% of the area when the determination by gas chromatography. After completion of the reaction, the reaction mixture is maintained at a temperature of from 5 to 10oC and washed with two portions of 317,513 kg (700 pounds) of aqueous 5% hydrochloric acid, the two portions of 330,667 kg (729 pounds) of aqueous 5% sodium hydroxide solution and one portion 324,317 kg (715 pounds) of aqueous 10% solution of sodium chloride. The ethyl acetate and acetone is then removed from the reaction mixture by distillation at a temperature between 65 and 75oWith less than 10 mm Hg as long as the concentration of the acrylate in solution is less than about 5 %. To prevent polymerization of the distillate is a mixture of acrylate and acetone stabilizing solution consisting of 95,2 g (0,21 pound) 4-methoxyphenol, is 95.2 g (0,21 pound fenotiazina and 12,700 kg (28 pounds) of toluene, which circulates through the condenser and distillate receiver. The temperature of the product residue is supported approximately at 45oWhen it salariat in the drum for future use. The yield of crude product, ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl] -4-ferbinteanu this reaction at this point usually around 82%. The number of servings obtained as described above, unite. The product of combining passed through evaporation apparatus with a short path p is vital under high vacuum to obtain the distilled product. Distillation in SPE using the conditions listed in the table. 2.

Percent of distilled ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl] -4-ferbinteanu is 80% (based on amount of starting amine), purity 91% (as determined by liquid chromatography high pressure).

1. The way to obtain ethyl--2-dichloro-5-[4-(deformity)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole-1-yl] -4-ferbinteanu formula I

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including the diazotization of 4-deformity-4,5-dihydro-3-methyl-5-oxo-1-(5-amino-2-fluoro-4-chlorophenyl)-1H-1,2,4-triazole and atilirovanie of acrylate obtained diazonium salt, wherein the diazotization and atilirovanie carried out simultaneously, to stir a solution of 4-deformity-4,5-dihydro-3-methyl-5-oxo-1-(5-amino-2-fluoro-4-chlorophenyl)-1H-1,2,4-triazole in 10 to 30 equivalents of acetone added from 0.05 to 0.5 equivalents of copper chloride (I), cool the solution to a temperature of from -20 to 30oC and maintain the temperature in this range under stirring and adding hydrochloric acid in an amount of not more than 3.4 equivalents per one mol. equivalent 4-deformity-4,5-dihydro-3-methyl-5-oxo-1-(5-amino-2-fluoro-4-chlorophenyl)-1H-1,2,4-trinil)-1H-1,2,4-triazole, while maintaining the temperature below 10oC and stirring, add 5 to 20 equivalents of acrylate, then bring the temperature of the stirred reaction mixture to about 0oWith and add 1.0 to 2.0 equivalents of sodium nitrite for 1-6 h while maintaining the temperature below approximately 20oWith and continue stirring for 15-90 min, followed by separation of the target product.

2. The method according to p. 1, characterized in that the stage of processing of the sodium nitrite should be at least one stage of washing.

3. The method according to p. 2, characterized in that the addition of the catalyst and treated with sodium nitrite is carried out in an atmosphere of inert gas; adding the catalyst used is from 20 to 25 equivalents of acetone; the temperature after addition of the catalyst support from -10 to 30oWith and use of anhydrous hydrochloric acid; the amount of added ethyl acrylate is from 10 to 15 equivalents; sodium nitrite is added in an amount of from 1.4 to 1.7 equivalents in the form of an aqueous solution containing 20-40 wt. % of sodium nitrite at a temperature below about 10oC, and the temperature of the at least one stage of washing support in the interval 0-20othe

 

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The invention relates to herbicide compositions containing herbicide derived sulfonylureas and at least one serviced, choose from a wide range of serviceof

FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention relates to new substituted benzoylketones of the general formula (I): , all possible tautomeric forms and possible salts that can represent active substance as a component of herbicide agent. In the formula (I) A means (C1-C4)-alkyl; R1 means cyclo-(C3-C6)-alkyl; R2 means hydrogen atom (H), cyano-group (CN); R3 means hydrogen atom (H), halogen atom, CF3, (C1-C4)-alkylsulfonyl; R4 means halogen atom; X means groups: or wherein R5 means (C1-C4)-alkyl, (C1-C4)-alkoxy-group, (C1-C4)-alkylthio-group, di-(C1-C6-alkyl)-amino-group; R6 means (C1-C4)-alkyl, (C1-C4)-alkoxy-group, cyclo-(C3-C6)-alkyl; n = 0 or 1 including all possible tautomeric forms and possible salts. Compounds of the formula (I) elicit herbicide activity and can be used in herbicide composition.

EFFECT: valuable properties of compounds.

3 cl, 1 sch, 3 tbl, 13 ex

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