Diethylethanolamine salt of 2-methoxycarbonyl-n-[(4 - methoxy-6-fluoro - 1,3 - pyrimidine-2-yl) aminocarbonyl] - benzosulfimide with herbicide activity and herbicide composition based on it

 

(57) Abstract:

Usage: in agriculture as having a weed-killing activity. The inventive diethylethanolamine salt of 2-methoxycarbonyl-N-[(4 - methoxy-6 - fluoro-1,3 - pyrimidin-2-yl) aminocarbonyl]benzosulfimide with herbicide activity and herbicide composition based on it containing the following components, wt. diethylammonium salt of 2-methoxycarbonyl-N-[(4 - methoxy-6 - fluoro-1,3-pyrimidine-2-yl) aminocarbonyl]benzosulfimide 10; stabilizer diethylethanolamine 4,3; emulator ethoxylated ALKYLPHENOLS, such as OP 7, OP-10, 2,5; solvent (triethylene glycol water at a ratio of 1 to 1) rest. 2 S. p. f-crystals, 6 PL.

The invention relates to a new derived arylsulfonamides diethylammonium salt 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3 - pyrimidine-2-yl)aminocarbonyl] benzene - sulfonamida with herbicide activity, as well as herbicide composition based on it, which can find application in agriculture.

There are known various sulfonylpiperidinylmethylene as herbicides, having a pyrimidine part as Deputy-chloro. However, these compounds is inadequate the Oli-2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3-pyrimidine-2-yl)-aminocarb - Neil]-benzosulfimide (compound II).

The connection is mainly used in the dose 0,125 kg/ha of nutrient content

However, the known compound has low solubility, which makes the development of preparative liquid forms. The water soluble forms of sulfonylation known 5% solution of sodium salt of 2-chloro-N-[(4-methoxy-6-methyl-1,3,5%triazine-2-yl)aminocarbonyl] benzosulfimide (chlorsulfuron), 5% of clorsulon and 95% water. This solution however has low stability.

Known stable aqueous suspension based chlorsulfuron. As stabilizing additives were used salts of carboxylic and inorganic acids diamoni phosphate, ammonium acetate, lithium, sodium or potassium thiocyanate sodium in the composition of the drug also wetting and dispersing additives, thickeners, content of active substance to 34%

However, the suspension is inferior to the true solutions when spraying precipitation, clogged nozzle sprayers, hence the uneven processing plants. In addition, the drug with many components to it and roads, decomposes within 2-3 weeks at 45aboutWith 0.4 0.47% of

Tasked with the search for new derivatives in a number of arylsulfonamides with high selectivity and good the problem is solved by the described diethylammonium salt of 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3-Piri - midin-2-yl)aminocarbonyl]Pensacola - foreign formula I:

(C2H5)2NCH2CH2OH have a weed-killing activity and herbicide composition containing as an active start diethylammonium salt of 2-methoxy-carbonyl-N-[(4-methoxy-6-fluoro-1,3-pyrimidine-2-yl)amino - carbonyl]benzosulfimide, as a stabilizer-diethylethanolamine, as an emulsifier is ethoxylated ALKYLPHENOLS, as solvent triethylene glycol and water in the ratio 1:1 with the following content, wt.

Diethylammonium salt

2-methoxycarbonyl-N-

[(4-methoxy-6-fluoro-1,3-

pyrimidine-2-yl)amino-

the carbonyl] Pensacola - Mead 10 Diethylethanolamine 4,3 Ethoxylated ALKYLPHENOLS (OP-7 and OP-10) 2.5 triethylene glycol:water in the ratio 1:1 Rest

OP-7 and OP-10 ethoxylated alkyl phenols of the formula

where R is alkyl (C8-C12)

OP-7, n=7-9

OP-10, n=10-12

The described salt as opposed to their acidic components, which is poorly soluble in water (at 25aboutC, pH=7-2,82 g/100 ml), infinitely soluble in water, which allows the use of compounds in aqueous solutions by the method of ultra-low volume and low volume spraying, and, consequently, the minimum to spend the drug, gently, vestiti in the rotation other cultures without negative impacts of herbicide.

Described herbicide composition is stable for more than 1.5 years, he has also shown high herbicide activity in flax crops of corn, barley.

While it is rapidly degraded in soil, practically non-toxic to subsequent crops.

P R I m e R 1. Diethylethanolamine salt of 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3-pyrimidine-2-yl)aminocarbonyl]Benz of rsulfed.

To 40 ml of water is added to 38.4 g (0.1 mol) 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1, 3-pyrimidine-2-yl)-aminocarbonyl] Ben-calcultated and with stirring was added dropwise 1.7 g (0.1 mol) of diethylethanolamine. Then the reaction mass is heated to a temperature of 40-45aboutC and maintained at this temperature for one hour. Cooled to room temperature, water is evaporated under reduced pressure, dried in vacuum desiccator. Get to 50.1 g, yield 100% transparent substance light yellow color in the form of butter.

Found, WITH 47,83; N 5,43; N 13,94; F 3,75; S 6,41; C20H20FN5O7S

Calculated With 47,90; N 5,59; N 13,97. F 3,79; S 6,39;

IR-spectrum (PL. CVG): 1700 cm-1,WITH=0 1660 cm-1with=1600 cm-1,SO2=1375 cm-1, 1165 cm-1.

PMR (CH CL3-dI), : 1,16 with CH3(C2H5<>OCH3, 6,40 with IT, 7,30 m 8.00 per Ar.

P R I m m e R 2. An aqueous solution diethylethanolamine salt 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3-pyrimidine-2-yl)- aminocarbonyl]-benzosulfimide.

It is 40.4 ml of water is added 103 g diethylethanolamine salt 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3-pyrimidine-2-yl)-aminocarbonyl] benzosulfimide, stirred until dissolved, add 1.2 g of diethylethanolamine, of 40.4 g of triethylene glycol, 5 g of OP-10.

Get part 1 light yellow color.

The resulting composition had the following physicochemical properties: pour point -28aboutWith, a surface tension of 45 nm/m, is stable for 1.5 years.

P R I m e R 2A. It is 40.4 ml of water, add 10 g of 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3-pyrimidine-2-yl)-aminocarbonyl] benzosulfimide and with stirring was added dropwise 1.2 g of diethylethanolamine. The reaction mass is heated to 40-45aboutC and kept at this temperature for 1.0 hours Then the reaction mass is then cooled and added with stirring to 40.4 g of triethylene glycol and 5 g of OP-10, stand 0.5 hours

Part II.

Physico-chemical characteristics of the composition:

Pour point 28aboutWITH

Surface is salammoniac salt 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3 - pyrimidine-2-yl)-aminostyrene] Ben - calcultated, stir until dissolved, add 1.2 g diethanolamine, of 40.4 g of triethylene glycol, 5 g of OP-7.

Get the structure of a light yellow color.

Physico-chemical characteristics of the composition:

Pour point 28aboutWITH

The surface tension of 45 nm/m

Stable for 1.5 years.

P R I m e R 3. Determination of contamination and yield of barley in the application diethylethanolamine salt 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3-pyrimidine-2 - yl)-aminocarbonyl]-benzosulfimide.

Culture spring barley, variety "Zatorski 85". Experience small-plot field, the area of the experimental plots 35 m2the area accounts plots 13.7 m2.

The herbicide treatment I and II were carried out in phase 3 leaf and tillering stage. The rate of fluid flow 300 l/ha dose of 5 and 10 g/ha of nutrient content, Method of application spraying solid with the help of knapsack sprayer "garden". Form of application of the water-glycol solution in accordance with example 2 or 3.

During the growing season were used to define the contamination of barley weeds according to the methods of their control (before treatment with the drug and before harvest) and yield of barley (see table.1).

In the control variabletype weeds, grass weeds were 4%

From table. 1 shows that herbicide activity of the composition containing the compound I was high during the whole vegetation period. Despite almost the same reduction of impurity in the different phases of processing, the yield reduction of contamination in the different phases of processing, the yield of barley reaches a maximum value at a dose of 10 g/ha, suggesting a stimulating effect of the herbicide on barley. The composition containing the compound II are less effective.

Analysis of productivity elements confirms the presence of a catalyst effect on barley. Basically stimulating effect was aimed at the ears, so increased such important components of yield, as the grain number in ear ears and the weight of 1000 seeds (see tab. 2).

P R I m e R 4. Determination of the effect of herbicides on yield of flax.

The tests were carried out on flax grades K-6. Experience small-plot field. The herbicide was made in the development phase, linen herringbone backpack sprayer. The herbicide was applied in the form of a 10% aqueous-glycolic solution of compounds I and II.

The results are given in table. 3.

NDS05=0,2 kg/ha.

When applied to the Jena linen are of high value the profitability of the use of herbicide is high enough. The herbicide containing the compound II, less effective.

P R I m e R 5. The definition of a weed-killing activity of compound I on corn.

The tests were carried out on maize variety Hybrid DZA in the phase of 2-3 leaves. The processing performed by the connection I and II at a dose of 10 and 20 g/ha of nutrient content in the form of a 10% aqueous-glycolic solution manual knapsack sprayer with a flow rate of 300 l/ha Biometrics of the corn crop was determined before harvest.

After treatment with herbicides increased biometrics: plant height, number of cobs, lots of plants and cobs and accordingly the yield of cobs. The composition comprising the compound II are less effective.

Experience has shown that the residues of compound I in the soil and the products of its decomposition effect on plants as growth stimulants.

P R I m e R 6. Definition aftereffect diethylethanolamine salt 2-methoxycarbonyl-N-[(4-methoxy-6-fluoro-1,3-pyrimi - DIN-2-yl)aminocarbonyl]benzosulfimide - Yes (compound I) on the test culture of the peas.

To study soil aftereffect of compound I investigated the reaction of peas on soil obtained after UBO is for example 2, at a dose of 30 g/ha of nutrient content in the phase of 2-3 leaves of barley and in the phase of tillering.

Determined the increase in length of roots of pea (% of control). Were compared with compound II.

When prirashenii length pea roots was increased by options. The maximum stimulatory effect was noted for germinating peas in the lower soil layer (20-30 cm), length of roots was increased by 68-86% vs. control. In the layers 0-10 and 10-20 cm stimulating effect of the drug was less pronounced. The connection moves down through the soil, but the number that survived to harvest, were concentrated in the upper 0-20 cm, where less pronounced growth-stimulating effect than 20-30 cm.

P R I m e R 7. Determining the duration of the biological activity of compound I on the test culture of cucumber.

After harvesting barley in the application of the compound I in a dose of 10 g/ha of nutrient content in the phase of tillering barley selected soil layer (0-10 cm) and had experience with the test culture of cucumber variety "far East". The experiment was carried out in growth chamber.

During vegetation the test culture was determined by the length of the stem, the weight of the stem and root 10 days after germination.

The results of determining the length biologicly, what in soil collected at the sites making the compound I in a dose of 10 g/ha seed germination was 100% the length of the stem of the cucumber exceeded the control, and vegetative mass cucumber was 2-2 .5 times higher than in the control.

Carried out tests to determine the effectiveness of compound I showed that it does not detrimentally impact on culture in rotation.

1. Diethylethanolamine salt of 2-methoxycarbonyl N ((4 - methoxy-6-fluoro-1,3-pyrimidine-2-yl) aminocarbonyl) benzosulfimide formula

< / BR>
have a weed-killing activity.

2. Herbicide composition based on a derived arylsulfonamides as active substance and a stabilizer, emulsifier and solvent, characterized in that as a derivative arylsulfonamides contains diethylethanolamine salt of 2-methoxycarbonyl-N-(4-methoxy-6-fluoro-1,3-pyrimidine-2-yl) aminocarbonyl)-benzosulfimide, as a stabilizer diethylamino-amine, as an emulsifier ethoxylated ALKYLPHENOLS, such as OP 7, OP 10, the solvent triethylene glycol and water in the ratio 1:1 with the following content, wt.

Diethylethanolamine the ethanolamine 4,3

Ethoxylated ALKYLPHENOLS 2,5

Triethylene glycol and water in the ratio of 1 to 1 Else

 

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FIELD: organic chemistry, herbicides, agriculture.

SUBSTANCE: invention describes a synergistic composition of herbicides comprising components (A) and (B) wherein (A) represents herbicide taken among the group of the formula (I):

wherein R1 means (C1-C4)-alkyl; R2 means (C1-C4)-alkyl; R3 means hydrogen atom; X and Y mean (C1-C4)-alkoxy-group; (B) represents one or two herbicides taken among the group of compounds or their acceptable forms: alachlor, metolachlor, acetochlor, dimetenamide, atrazine, cyanasin, metribusin, fluthiamide, nicosulfuron, rimsulfuron, primisulfuron, pendimetalin, sulcotrion, dicamba, mesotrion, isoxachlortol, metosulam, anilofos, fenoxaprop-ethyl, setoxydim, diclofop-methyl, MCPA, bromoxynil, pyridat, clopyralid, iodosulfuron-methyl, ethoxysulfuron, amidosulfuron, gluphosinat-amminium, isopropylammonium-glyphosate, imasetapir wherein components (A) and (B) are taken in the effective doses. Also, invention describes a method for control of weeds by using above indicated herbicide composition. Invention provides the development of the synergistic herbicide composition eliciting high activity.

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6 cl, 26 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: claimed mixture from herbicides and antidotes contains (A) herbicidically active substance based on phenylsulfonylureas of formula I and salts thereof (in formula R1 is hydrogen or C1-C6-alkyl; R2 is C1-C3-alkyl; R3 is C1-C3-alkoxy; R4 is hydrogen or C1-C4-alkyl; Hal is fluorine, chlorine, bromine, or iodine); and (B) antidote of formulae II or III , wherein X is hydrogen, halogen, C1-C4-alkyl; C1-C4-alkoxy, nitro or C1-C4-haloalkyl; Z is hydroxyl, C1-C8-alkoxy, C3-C6-cycloalkoxy, C2-C8-alkenyloxy, C2-C8-alkynyloxy; R5 is C1-C2-alkandiyl chain optionally substituted with one or two C1-C4 alkyl residues or (C1-C3-alcoxy)carbonyl; W is bivalent heterocyclic residue; n = 1-5; in weight ratio herbicide/antidote of 100:1-1:100. Also disclosed is method for protection of cultural plants against phytotoxic side effect of herbicidically active substance of formula I. Claimed method includes antidote application of formulae II or III on plant, plant parts, plant seeds or seeding areas before or together with herbicidically active substance in amount of 0.005-0.5 kg/hectare in weight ratio of 100:1-1:100.

EFFECT: mixture for effective selective weed controlling in cultural plant, particularly in maize and grain cultures.

8 cl, 2 ex, 7 tbl

FIELD: agriculture, in particular herbicide compositions.

SUBSTANCE: invention relates to weed controlling method for tolerant grain crops using (A) road spectrum herbicides selected from group (A1) glufosinate (salt) and related compounds; (A2) glyphosate (salt) and related compounds; and (B) one or more herbicides selected from group containing (B1) herbicides selectively effecting in grain crops especially against monocotyledonous weeds effecting on folia and/or soil (residual benefit); or (B2) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting especially on folia; or (B3) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia or soil; or (B4) herbicides selectively effecting in grain crops against monocotyledonous or dicot weeds effecting on folia; wherein components (A) and (B) are used in synergic ration. Also are described herbicide compositions containing (A1) ) glufosinate (salt) and related compounds and herbicide from group (B); as well as herbicide compositions containing(A2) glyphosate (salt) and related compounds and herbicide from group (B); wherein components (A) and (B) are used in synergically effective ration.

EFFECT: effective controlling of weeds in grain crops.

6 cl, 70 tbl, 3 ex

FIELD: organic chemistry, agriculture, herbicide composition.

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EFFECT: effective composition and method for weed controlling.

5 cl, 11 tbl, 7 ex

FIELD: agriculture, in particular method for controlling of weeds.

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EFFECT: effective controlling of weeds in tolerant maize cultures.

6 cl, 55 tbl, 3 ex

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to new substituted thienyl(amino)sulfonylureas of formula I ,

wherein A represents nitrogen or methane; Q represents direct bond or imino; R1 represents fluorine, chlorine, bromine, unsubstituted C1-C4-alkyl, C1-C4-alkoxyl optionally substituted with halogen, unsubstituted C1-C4-alkylthio, or di(C1-C4-alkyl)amino; R2 represents hydrogen or C1-C4-alkyl. Compounds of present invention are useful as herbicide agents.

EFFECT: new compounds with herbicide activity.

5 cl, 11 tbl, 5 ex

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EFFECT: effective controlling of weeds in cotton crops.

9 cl, 12 tbl, 3 ex

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EFFECT: valuable properties of herbicide composition.

4 cl, 2 tbl, 9 ex

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EFFECT: herbicidal composition of increased activity and deferred hydrolysis in wetted powder.

3 cl, 6 ex, 2 tbl

FIELD: organic chemistry, agriculture.

SUBSTANCE: invention relates to selective herbicidal compositions, containing customary auxiliary substances, as well as: a) herbicidal effective amount of compound of formula I or agriculture acceptable salt thereof wherein R are independently C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alcoxy-C1-C4-alkyl, or C1-C4-alcoxy-C1-C4-alcoxy-C1-C4-alkyl; m = 2; Q is group of formula wherein R23 is hydroxyl and Y is C1-C4-alkylen bridge; and b) synergetically effective amount of one or more herbicides; and methods for controlling of undesired plants in tame cultures using the said composition. Also disclosed is composition containing customary auxiliary substances, as well as herbicidal and synergetically effective amount of 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one of formula 2.2 and herbicidal antagonistically effective amount of antidote of formula 3.1. Compositions based on 4-hydroxy-3-(2-methyl-6-trifluoromethylpyridine-3-carbonyl)bicyclo[3.2.1]octo-3-ene-2-one and herbicidal antagonistically effective amount of antidote, as well as methods for controlling of weeds and cereal grasses in tame cultures also are described.

EFFECT: compositions useful in effective controlling of many weeds both in pre-spring and post-spring phases.

5 cl, 63 tbl, 12 ex

FIELD: chemistry, pharmacology.

SUBSTANCE: invention relates to novel compounds of formula (I), its pharmaceutically acceptable salts, possessing qualities of chemokine receptor modulators. Compounds can be applied for asthma, allergic rhinitis, COLD, inflammatory intestinal disease, irritated intestine syndrome, osteoarthritis, osteoporosis, rheumatoid arthritis, psoriasis or cancer. In compound of formula (I) , R1 represents group selected from C1-8alkyl, said group is possibly substituted with 1, 2 or 3 substituents, independently selected from -OR4 , -NR5R6 , phenyl, phenyl is possibly substituted with 1, 2 or 3 substituents, independently selected from halogeno, -OR4,-NR5R6,-SR10,C1-6alkyl and trifluoromethyl; R2 represents group selected from C1-8alkyl, said group is substituted with 1, 2 or 3 substituents, independently selected from hydroxy, amino, C1-6alkoxy, C1-6alkylamino, di(C1-6alkyl)amino, N-(C1-6alkyl)-N-(phenyl)amino; R3 represents hydrogen, R4 represents hydrogen or group selected from C1-6alkyl and phenyl, R5 and R6, independently, represent hydrogen or group selected from C1-6alkyl and phenyl, said group being probably substituted with 1, 2 or 3 substituents, independently selected from -OR14, -NR15R16, -COOR14,-CONR15R16, or R5 and R6 together with nitrogen atom, to which they are bound, form 4-7-member saturated heterocyclic ring system, possibly containing additional heteroatom, selected from oxygen and nitrogen atoms, ring possibly being substituted with 1, 2 or 3 substituents, independently selected from -OR14, -COOR14,-NR15R16,CONR15R16 and C1-6alkyl; R10 represents hydrogen or group selected from C1-6alkyl or phenyl; and each from R7, R8, R9, R14, R15, R16 independently represents hydrogen, C1-6alkyl or phenyl; X represents hydrogen, halogeno; Rx represents trifluoromethyl, -NR5 R6 , phenyl, naphtyl, heteroaryl, heteroring can be partly or fully saturated, and one or more ring carbon atoms can form carbonyl group, each phenyl or heteroaryl group being possibly substituted with 1, 2 or 3 substituents, independently selected from halogeno, cyano, -OR4, -NR5R6, -CONR5R6, -COR7, -COOR7, -NR8COR9, -SR10, -SO2R10, -SO2NR5R6, -NR8SO2R9, C1-6alkyl or trifluoromethyl; or Rx represents group selected from C1-6alkyl, said group being possibly substituted with 1, 2 or 3 substituents, independently selected from halogeno, -OR4, -NR5R6, phenyl or heteroaryl, where heteroaryl represents monocyclic or bicyclic aryl ring, containing from 5 to 10 ring atoms, from which 1, 2 or 3 ring atoms are selected from nitrogen, sulfur or oxygen. Invention also relates to methods of obtaining compounds, versions, pharmaceutical composition and application for manufacturing medications using compounds of invention.

EFFECT: obtaining novel compounds of formula (I), its pharmaceutically acceptable salts, possessing properties of chemokine receptor moduators.

25 cl, 138 ex

FIELD: chemistry.

SUBSTANCE: method of obtaining water-soluble diethylamine salts of aryl sulphonylureas by formula (1): , where R1-Cl, CF3, COOCH3, COOC2H5, CH2CH2CF3, OCH2CH2Cl, OCH2CH2OCH3, SO2CH2CH3, CON(CH3)2;R2-CH3, OCH3, OCHF2, OC2H5; R3-CH3; OCH3, OCHF2, Cl, NHCH3; R4-H, CH3; X-N, CH; Y-N, CH; M-(C2H5-NH-C2H5), includes interaction of equimolar quantities of proper aryl sulphonylurea and diethylamine in water medium with further separation of target product. As a rule interaction of initial reagents is carried out mainly at temperature 30-45C, if necessary, in mother liquor medium, obtained after separating target product in previous cycle. Separation of product is usually realized by target product crystallisation or salting-out at temperature not more than 20C.

EFFECT: possibility to use in agriculture as herbicidal means or in herbicidal compositions.

3 cl, 1 tbl, 7 ex

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