1-{[o-(cyclopropanecarbonyl)-phenyl]-sulfamoyl}-3-(4,6 - dimethoxy-2-pyrimidinyl)urea

 

(57) Abstract:

Usage: as a herbicide. Essence: 1-{[O-(cycloalkylcarbonyl)phenyl] sulfamoyl} -3-(4,6-dialkoxy-2 - pyrimidinyl)urea. Reagent 1: on-aminophenylacetylene. Reagent 2: 2-amino-2,4-dimethoxypyridine. Reaction conditions: dichloromethane solution 2 with the addition of chlorosulfonylisocyanate at 0.5oWith and reagent 1 in dichloromethane in presence of triethylamine at room temperature. 11 table.

The invention relates to methods seleting suppression of undesirable plant species in the presence of crops.

The aim of the invention is a derivative of 1-{[O-(cycloalkylcarbonyl)phenyl] sulfamoyl} -3-(4,6-dialkoxy-2 - pyrimidinyl)urea, which is a highly effective herbicide and can be used for selective suppression of undesirable plant species in the presence of crops.

The aim of the invention is also selectively acting herbicide 1-{ [O-(cycloalkylcarbonyl)phenyl] sulfamoyl} -3-(4,6-dialkoxy-2 - pyrimidinyl)urea, having at least twice the margin of safety when used against broad-leaved weeds and secutirty a margin of safety when used as a means to control broadleaf weeds and sedges in the presence of seed paddy-rice.

Another aim of the invention is a method for the selective suppression of undesirable vegetation in the presence of cereal crops using 1-{ [O-(cyclopropanecarbonyl)phenyl] sulfamoyl}-3-(4,6-dimethoxy-2 - pyrimidinyl)urea. Among the unwanted weeds suppressed above sulfamoylbenzoic include Cassia tupolisty (wall-cress canadian, Cassia anobtusifolita annual sedges, yperaceal nual; ryppa Cyperus esculentus flat sedge, yperus serotinus the arrowhead Sagittaria pygmaca; sedge round yperus rotundus; bulrush, Scirpus species; morning glory, type Ipomoca and hemp Sesbania exalta.

It was found that the above compound is effective for the selective inhibition of various weed species in the presence of cereal crops and is especially effective for combating broadleaf weeds and sedges in the fields with seed paddy-rice.

In addition, it was found that such a connection as 1-{ [O-(cyclopropanecarbonyl)phenyl] sulfamoyl} -3-(4,6-dimethoxy-2 - pyrimidinyl)urea, is unique among sulfamoyl-derivatives of urea due to extremely high security for agricultural crops, especially rice, and in particular for seed paddy-rice.

In line is through the reaction of 2-amino-4,6-dimethoxypyrimidine with chlorosulfonylisocyanate in the presence of methylene chloride followed by treatment of the thus prepared mixture of o-aminophenylacetylene and triethylamine in the presence of methylene chloride, in the result, get the target connection.

Established fact that the selectivity in respect of the grains of cereals, especially rice, is achieved by introducing cyclopropenes groups in the phenyl nucleus sulfamoyl-derived urea, is unexpected. Moreover is also surprising that such a substitution achieve selective inhibition of various unwanted weeds, especially broadleaf weeds and sedges in the presence of barley, wheat, oats and rye, and rice. In addition, a significant advantage is that the development and/or maturation of some unwanted weeds, such as chicken millet and Elytrigia repens, significantly slowed down or suppressed completely in contact with 1-{ [O-(cyclopropanecarbonyl)phenyl] sulfamoyl}-3-(4,6-dimethoxy-2 - pyrimidinyl)urea during herbicide applications, leading to suppression of broadleaf weeds and sedges in the presence of crops.

In practice, processing of agricultural crops specified sulfhemoglobin can be used in solid or liquid herbicide compositions comprising an effective concentration of sulfanilamide in an inert solid or ako in the case of processing rice more efficiently to make the above compounds, preferably in granular form, planting to emergence, that is, to bring the soil or flood water after planting rice, but before or immediately after germination of weeds. The compositions also can be done during pre-processing.

The proposed formulations can also be made by foliar processing circuit crops post-emergent weeds, and they are especially suitable for combating weeds in barley, wheat, oats, rye and right-seeded rice.

Preferably 1-{ [O-(cyclopropanecarbonyl)phenyl] sulfamoyl}-3-(4,6-dimethoxy-2 - pyrimidinyl)urea can be used in the form of wettable powders, liquid flowable or granular form suitable for application fields of crops on which you want to destroy the weeds.

Wettable powder can be prepared by the joint grinding about 65 wt. /Mac. 1-{[O-(cyclopropanecarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2 - pyrimidinyl)urea; 25,7 wt./wt. bentonite clay; 6.0 wt. /Mac. sodium sulfonates modified Kraft lignin containing no sugars (dispersant); 3.0 wt./wt. anionic surfactants, such as dioctylsulfosuccinate (wetting agent); maciveys powder crops and weeds, the growing of crops, the powder is usually dispersed in water and sprayed in the form of water jets. As a rule, for the selective control of unwanted vegetation, in particular broad-leaved weeds and sedges in the presence of cereals spraying carried out on the basis of making about 0,016-1.0 kg/ha and preferably from 0.01 to 0.20 kg/ha above 1-{ [O-(cyclopropanecarbonyl)phenyl] sulfamoyl}-3-(4,6-dimethoxy-2 - pyrimidinyl)urea.

Above sulfamoylbenzoyl urea can also be prepared in the form of a granular composition by dissolving whether dispersion of active compound in a solvent such as acetone, dichloromethane, or a similar solvent, and processing toxic mixture with the solvent granular forms with absorption capacity, such as Atta-pulpit, Mont-morillonite, crushed corn cobs, bentonite and the like. Usually when handling toxic granules with a solution of the latter has such a concentration of toxic substances, to ensure that the herbicide content of the drug in granules of about 0.20 to 2.0 wt./about. If necessary, can be used and a higher concentration of herbicide preposed in soil or water, which grow crops, about 0,016-1.0 kg/ha and preferably about 0.02 to 0.20 kg of herbicide/ha cultivated area occupied by crop.

Ordinary concentrated fluid composition is prepared by co-grinding about 20-60 wt. sulfhemoglobin, 1-5 wt. sodium salt of condensed naphthalenesulfonic, 2-4 wt. swelling clays, 2 wt. propylene glycol and about 30-55 wt. water.

Fluid concentrate is usually dispersed in water before processing of land under crops in the quantity, ensure the introduction of herbicide at the rate of about 0,016-1.0 kg/ha and preferably about 0.02 to 0.20 kg/ha.

Example 1. Obtaining on-aminophenylacetylene

To 100 ml odnopolyarnogo solution of boron chloride in dichloromethane and 100 ml of dichloroethane was added 9.3 g (0.1 mol) of aniline at 0-5oC. After addition of aniline in a mixture was made of 10.0 grams (0.15 mol) of cyclopropylamine and then dropwise to 14.4 g (0.11 mol) AlCl3. The mixture was allowed to spontaneously warm to room temperature and placed into the distillation. From a mixture drove dichloromethane until the temperature of the bath 70oC. the Remaining is th bath and to the cooled mixture were added water. The amount of added water is sufficient to dissolve the solid mass in the mixture, and then the whole mixture was twice extracted with dichloromethane portions of 100 ml. Organic extracts were combined, dried over anhydrous magnesium sulfate and was evaporated in vacuum, obtaining 9.3 g of a yellow oil (70% yield). The reaction scheme is shown below:

< / BR>
Example 2. Obtain 1-{ [O-(cyclopropanecarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2 - pyrimidinyl)urea

In an ice bath cooled to 0.5oC a solution of 1.78 g (0,0114 mole) 2-amino-4,6-dimethoxypyrimidine in 50 ml of dichloromethane and then added 1.0 ml (1,62 g, 0,114 mol) chlorosulfonylisocyanate. The reaction mixture was stirred 30 min and then slowly added 2.66 g of o-aminophenylacetylene (70% 0,114 mol) and 2.6 ml of triethylamine (0,0187 mol) in 50 ml of dichloromethane. The resulting solution was stirred at ambient temperature for 18 h

The reaction mixture then was evaporated in vacuo and the resulting residue was dissolved in 50 ml of methanol. PH of the resulting solution adjusted to a pH of about 1 to 10% solution of hydrochloric acid, and the solution was kept. From the solution precipitated white precipitate, which was filtered and dried, obtaining 3.8 g (70% ) of the desired product with a point of plavini the tailings making

Resistance (tolerance) of rice to the connection according to the invention with pre-emergence making is illustrated by the following experience: grain rice (Tebonnet) were planted in steamed sand loam from under Lavra American, containing 15% organic matter. Loamy soil were placed in a 10 cm square plastic vessels. Spent three parallel experiments. After landing vessels watered until complete absorption and then sprayed using a laboratory sprayer. The test compound was made in a water-acetone mixture of about 50/50. /about. in quantities equivalent to the rate of flow of 1,0; 0,5; 0,25; 0,125; 0,063; 0,032; 0,016 and 0.008 kg/ha Treated vessels are then placed in the greenhouse on irrigated shelves under normal greenhouse conditions. Each vessel was observed within three to four weeks and were evaluated herbicide effect of visual condition determination, size, vigor, chlorosis, curvature and General appearance of the plants. Used the following grading scale (see table.1).

While presenting results of the present example uses the following abbreviations.

Reducing the Content

PE pre-emergence

POST-T After landing

BYG Chicken millet

CYPSE Cyperus serotinus

g/ha g / ha

Sustainability of rice in the processing after landing and flood irrigation, see table.3.

The stability of seed rice to the post-transplantation making herbicide was determined as follows: two Rostock ten seedlings of rice (Tebonnet) were planted in the muddy sangineto soil 900 gram containers with a diameter of 10.5 cm and do not have drainage holes. After disembarking the vessel was filled with flood water and maintain the water level by 1.5-3 cm above the soil surface. Three days after transplantation, the filled surface of the soil in the containers was treated with a water-acetone mixture of about 50/50./about. containing compound in amounts that provided the rate of flow of 1,0; 0,5; 0,25; 0,125; 0,063; 0,032; 0,016 and 0.008 kg/ha active ingredient. Processed herbicide containers were placed on the shelves of the greenhouse, watered so that the water level was maintained at the level indicated above, and kept at normal greenhouse conditions. After three or four weeks after treatment, the tests were stopped, examined every capacity.

Pre-emergence control of weeds in irrigation of flood waters

The following image was determined by pre-emergence herbicide activity under conditions arosenius in the top layer of silty loam soil to a depth of 0.5 cm and 900 gram plastic containers with a diameter of 10.5 cm and do not have drainage holes. Was added in the tank water so that she was on 1.5-3 cm above the soil surface throughout the experiment. Compound was injected directly into the flood water in the form of iodoacetamide a mixture of 1:1 vol./about. from the rate of consumption of the active component 1,0; 0,5; 0,25; 0,125; 0,063; 0,032; 0,016 and 0.008 kg/ha Herbicide treated tanks were installed on the shelves in the greenhouse and kept at normal conditions in the greenhouse. 3-4 weeks after treatment, the experiment was stopped and carried out the inspection of each tank. Herbicide effect was evaluated according to the scale.

Safety assessment for rice and the control value of the weeds

Safe rates for rice meets the highest consumption rate (g/ha), in which the herbicide effect is equal to 0 or 1. The rate of application for the control of weeds is the amount (g/ha), in which the herbicide effect on the above scale corresponds to 8 or 9. see tab. 4.

The limits of the selectivity table.5.

Selective limit represents the value of the security norms of consumption of rice (g/ha) divided by the consumption rate for the regulation of every species of weeds (barnyard millet and yperus serotinus). The amount rasschityvayuschei. Although the pre-emergence method of planting was not used in irrigated floodwater conditions, this method is more extreme to assess the physiological tolerance of rice to these herbicides, as the rice plants exposed to herbicides from the moment of germination.

Example 4. Regulation of broadleaf weeds and resistance in wheat and barley during post-harvest processing

The following experiment demonstrates how post-harvest herbicide activity and selectivity for barley and wheat. Seeds or reproductive organs of each plant species were planted in separate pots with artificial soil for greenhouses, consisting of peat moss, vermiculite, sand and charcoal (Metromix 350). Plants were placed approximately two weeks in the greenhouse. Then the plants were sprayed with aqueous acetone solution containing test compound in the amount corresponding to the consumption rate of about 0,004-2.0 kg/ha Solutions also contained about two molar equivalent of diethylamine on the molar equivalent of the test compound to facilitate solubility of the test compound in a water-acetone solution. The solutions also contained 0.25% activator p is

After spraying, the plants were placed on the shelves in the greenhouse and maintained standard conditions in the greenhouse. After 3-5 weeks after treatment was controlled every pot and above the scale was evaluated herbicide effect.

To determine the endurance of crop plants for each treatment were used for three of the pot. The following data are averages of three measurements.

Used in the experiments, the crops of weeds

Crops

Household name and type Scientific name

Rice variety Tebonnet Oryze sativa

Barley, winter wheat, variety Barberouse Hardeum sulgare

Barley spring, kind Bonawza -"-

Winter wheat, variety Fidel Triticum aestivum

Spring wheat, variety of Katepwa -"-

Durum wheat, variety Walooma -"-

Types of weeds, see table. 6.

The resilience of crops and their varieties with post-harvest treatment of 1-{[O-(cyclopropanecarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2 - pyrimidinyl)urea.

Visual assessment of the effectiveness of the herbicide in accordance with the scale efficiency above (see tab. 7).

Regulation of correcaminos.

The evaluation system according to example 3 (see tab. 8).

Next, a comparative assessment of herbicide action and phytotoxicity against rice known and declared compounds (see table. 9).

Species see table.10

Classification system, see table. 11.

1. 1-{[O-(Cyclopropanecarbonyl) -phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea.

2. Connection O-aminophenylacetate.

3. Herbicide composition comprising a derivative sulfhemoglobin and an inert carrier, characterized in that as sulfanilamide using 1-{[O-(cyclopropanecarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea in an amount of 0.2 to 65 wt. inert media - the rest.

 

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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.

EFFECT: improved method for control, valuable properties of composition.

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

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EFFECT: effective controlling of weeds in grain crops.

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EFFECT: effective composition and method for weed controlling.

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SUBSTANCE: claimed method for controlling of weeds in tolerant maize cultures includes application of composition comprising (A) road spectrum herbicide from group (A1) glufosinate (salt) and analogs, (A2) glyfosate (salt) and analogs; (B) one or more herbicides from group (B1) cyanazin, alachlor, nicosulfurone, rimsulfurone, sulkotrion, mesotrion, and penthoxamid; (B2) pendimethalyne, methosulam, isoxaflutol, metribuzin, chloransulam, flumetsulam, linuron, florasulam, and isoxachlorotol; and (B3) bromoxinyl, chlorpyralid, tifensulfuron, MCPA (2-methyl-4-chlorophenoxyacetic acid), halosulfuron, and sulfosulfuron, wherein (A) and (B) components are in synergic effective ration. Also disclosed are herbicidal compositions including compound from group (A1) or )F2) and herbicide from group (B).

EFFECT: effective controlling of weeds in tolerant maize cultures.

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

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EFFECT: new compounds with herbicide activity.

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EFFECT: effective controlling of weeds in cotton crops.

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