NL8006568A - UREA DERIVATIVE, METHOD FOR PREPARING IT, HERBICIDE PREPARATIONS CONTAINING THE UREA DERIVATIVE AND METHOD FOR CONTROLLING WEEDS USING THE DERIVATIVE. - Google Patents

Description

* * 4 • 6 UEEUMERIYATE, WEEKLY PREPARING ERVM, HERBICIDE PREPARATIONS CONTAINING THE UREA DERIVATIVE AND METHOD TO CONTROL WEED USING THE DERIVATIVE 1 8006568

The present invention relates to a urea derivative, a process for its preparation, herbicidal compositions containing the urea derivative and a method of weed control using the derivative.

5 From U.S. Pat. 2,655 a very wide range of urea derivatives with herbicidal properties is known. In the period of more than 25 years that has elapsed since these compounds were prepared, much research has been done with regard to the use of urea derivatives, as herbic XO cides. The main urea derivative is probably the compound 3- (H-isopropylphenyl) -1,1-dimethylurea, which is commercially available under the name "Isoproturon" - This compound is widely used in Europe to control winter grain weeds. The main advantages of this compound are the very high effectiveness against a wide range of weeds and the fact that the compound can be applied both in autumn and in the spring before and after the emergence of the crop. The main drawback of the compound is that it has no "efficacy" against "certain commercially" important weeds, particularly "perennial broadleaf weeds, perennial grassy weeds, sticky weeds and speedwell. It has now been found that a particular phenylurea derivative, which is disclosed in U.S. Pat. 2,655 ΛΗΤ is not specifically mentioned and the phenyl ring of which contains two specific substituents has particularly useful herbicidal properties.

The invention therefore relates to the compound of the formula: GH

-M-co-1KcH 2 (o) 10 or 3- (3-methyl-k-isopropylphenyl) -1,1-dimethyl-urea. This compound is particularly suitable for combating weeds that are between cereals, such as maize, barley or, especially, wheat, before or after the crop has emerged. As can be seen from the data reported in Examples U and 5 below, this compound provides clear benefits for the weed control between wheat plants compared to the commercial herbicide Isoproturon.

The invention further relates to a process for the preparation of the compound of the formula 0 ", wherein the aniline 20 of the formula I or a hydrohalide salt thereof: 1 Va · s'WO) -12 (is reacted with: a) a dimethylcarbamoylhalide , preferably the chloride, or b) phosgene (CQClg), to prepare the isocyanate of the formula: 8006568 f if 3

V

ί-Ο Ξγ- ^ (^ Ο -®C0 (II) and at least a portion of left isocyanate with dimethylamine reacted Hccdt. Method (a) lan network cf Zander .oplosmiddel -warden lit stirred.

Suitable solvents are hydrocarbons and halogenated hydrocarbons, for example, henzene, toluene or carbon tetra-chloro. The process is preferably carried out under substantially anhydrous conditions. Since the reaction is a condensation reaction in which hydrogen halide is removed, it is preferably carried out in the presence of a dehydrohalogenating agent; organic or inorganic bases 10 can be suitably used; sodium acetate has proved particularly useful when operating without a solvent, and organic bases such as triethylamine or pyridine are suitable when a solvent is used. The reaction is preferably carried out at a temperature of 0-80 ° C, preferably at room temperature, and the reaction mixture can be worked up by conventional means.

Process (b) is suitably carried out in the presence of a solvent, for example, a hydrocarbon, such as toluene, at a temperature of 30-120 ° C; it is advantageous to allow the reaction to proceed at the reflux temperature of the solvent used. The obtained isocyanate of formula II can be separated from the reaction mixture if desired, but is preferably reacted in situ with dimethylamine. This reaction is conveniently carried out at a temperature of 0-3 ° C, preferably at room temperature. The desired product can be separated by any suitable method.

The invention further relates to a herbicidal composition containing the compound of formula 0 as well as a suitable carrier. The invention also relates to a

P ^ P P

k method for preventing unwanted plant growth in a field, wherein the compound or a preparation according to the invention is applied to the field.

In some cases it may be desirable to mix the compound of the invention with one or more other compounds having herbicidal activity, for example, to modify the spectrum of activity. The compound of the invention can therefore be mixed with other herbicides, the activity of which has a broad spectrum, such as 2- (chloro-10-6-ethylamino-s-triazin-2-ylamino) -2-methylpropionitrile (the commercial herbicide "cyanazine "), or with more specialized narrow spectrum herbicides, such as herbicides to control alanine wild oats, as described in British Patent ITo. I.16U.160, for example ethyl 15 H-benzyl-H- (3, dichlorophenyl) -2-aminopropionate (the commercial herbicide "benzoylpropethyl") and the racemic mixture or (-) isomer of isopropyl or methyl H benzoyl-N- (3-chloro-1-fluorophenyl) -2-aminopropionate (the commercial herbicides "flampropisopropyl" and "flampropmethylM).

A carrier for a preparation according to the invention can be any material with which the active ingredient has been mixed for the purpose of applying it to the crop, seed, soil or other object to be treated, or the storage, transport or facilitate its processing. A carrier can be a solid or liquid material, as well as a material which. is gaseous under normal conditions but has been compressed into a liquid, and any carrier material commonly used in formulating herbicidal compositions.

Suitable solid carriers are natural and synthetic clays and silicates, for example natural silicas, such as diatomaceous earth, magnesium silicates, for example talc, magnesium aluminum silicates, for example, attapulgites and vermiculites; aluminum silicates, for example kaolinites, montmorillonites and micas; calcium carbonate; calcium sulfate; 8 0 0 6 5 6 8 5

1 J

synthetic hydrated silicon oxides and synthetic calcium or, ιπτπm "iimm'Ti <? atem; elements such as carbon and sulfur; natural and synthetic resins such as coumarone resins, polyvinyl chloride and styrene polymers and copolymers; solid poly-5 chlorine &noJen;bitumen; waxes such as beeswax, paraffin and chlorinated mineral paraffins, as well as solid fertilizers, for example, superphosphates.

Examples of suitable liquid carriers are water, alcohols such as isopropanol and glycols; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; ethers; aromatic or araliphatic hydrocarbons, such as benzene, toluene and xylene; petroleum fractions, such as kerosene, light mineral oils; chlorinated hydrocarbons, such as carbon tetrachloride, perchlorethylene, trichloroethane. Mixtures of different liquids are often suitable.

Agricultural preparations are often prepared and transported in a concentrated form, after which they are diluted by the consumer before application. This dilution is facilitated by the presence of small amounts of a carrier, which is a surfactant. In a composition according to the invention, therefore, at least one carrier is a surfactant.

For example, the composition may contain at least two carriers, at least one of which is a surfactant.

* «

The surfactant can be an emulsifying agent, a dispersing agent or a wetting agent; the substance can be nonionic or ionic. Examples of useful surfactants are the sodium or calcium salts of polyacrylic acids and lignin sulfonic acids; the condensation products of fatty acids or aliphatic amines or aides with at least 12 carbon atoms per molecule with ethylene oxide and / or propylene enzyme; the fatty acid esters of glycerol, sorbitan, sucrose or pentaerythritol; condensates thereof with ethylene oxide and / or propylene oxide; condensation products of fatty alcohols or alkyl phenols, for example octylphenol or p-ethylcresol, with ethylene oxide and / or propylene oxide; 8006568 6 sulfates or sulfonates of these condensation products; alkali or alkaline earth metal salts, "preferably sodium salts of sulfuric or sulfuric acid esters containing at least 10 carbon atoms per molecule, for example sodium lauryl sulfate, secondary sodium alkyl sulfate, and sodium salts sulfonated castor oil and sodium alkylaryl sulfate, such as sodium dodecylbenzyl; polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

The compositions obtained by the method according to the invention can be formulated in the form of spray powders, dusts, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates and aerosols. Spray powders usually contain 25, 50 or 75% by weight of active material and in addition to solid inert carrier usually 3-10 wt% of a dispersant and, if necessary, 0-10 wt% of one or more stabilizers and / or other additives such as penetrants or. adhesives. Dusting powders are usually formulated in the form of a dusting powder concentrate with a composition similar to that of a wettable powder, but without dispersant, and are diluted on site with a further amount of solid carrier to a formulation usually 0.5-10% by weight of active material. contains. Granules are usually prepared in a size of 1,676-0,152 mm using agglomeration and impregnation techniques. Granules generally contain 0.5-25% by weight of active material and 0-10% by weight / s of additives such as stabilizers, slow release agents of the active material, and binders. Emulsifiable concentrates contain, in addition to the solvent and, if required, auxiliary solvent, 10-50 w / v / s active material, 2-20 w / v / w emulsifiers and 30-20 w / v / w. Other additives, such as stabilizers , penetrating agents and anti-corrosion substances. Suspension concentrates are usually formulated to provide a stable, non-sediment-forming free-flowing product and usually contain 10-75 wt.% Active material, 0.5-15 wt.% 8 0 0 6 56 8 & 7 dispersants 0.1-10% by weight of suspending agents, such as protective colloids and thixotropic agents, 0-10% by weight of other additives, such as anti-foaming agents, anti-corrosion agents, stabilizers, penetrating agents and adhesives, and water or an organic liquid in which the active material is practically insoluble; certain organic solids or inorganic salts theirs are dissolved in the formulation to help prevent sedimentation or as antifreeze agents for water.

Aqueous dispersions and emulsions, for example, preparations obtained by diluting a spray powder or a concentrate according to the invention with water also fall within the scope of the present invention. The said emulsions may be of the water-in-oil or oil-in-water type and may have a thick, mayonnaise-like consistency.

The preparations obtained according to the method according to the invention can also contain other ingredients, for example other compounds with insecticidal or fungicidal properties.

The invention is further illustrated in the following Examples.

EXAMPLE I - Preparation of 3- (3-methyl-1-isopropylphenyl) -1-dimethyl-urea-3-methyl-4-isopropylaniline (7.1 µg) and anhydrous sodium acetate (0.5 g) were used as a solid mixture stirred together and dimethylcarbamoyl chloride (5Λg) was added over 15 minutes. The mixture was allowed to stand at room temperature overnight, after which it was treated with water and extracted with methylene chloride. After it was dried over magnesium sulfate, the solvent was evaporated and the solid obtained was recrystallized from a mixture of hexane and toluene. 3.5 g of the desired product, m.p. 153 DEG-15 DEG C., were obtained.

Analysis C Η N

Calculated for G ^ H ^ NgO 70.9 9 * 1 12.7

Found 69.9 9 * 1 12.1 8006 56 8 8 EXAMPLE 2 - Other "Preparation Method for the Compound of the Invention" 3-Methyl-4-isopropylaniline (5g »purity QO%) in toluene (150ml) was added to the reflux temperature was heated while COCl 2 gas was passed through the solution for about 1.5 hours, then dry nitrogen was passed through the solution to remove excess COCl 2. After the solution was cooled to room temperature, dimethylamine (5 g ) in toluene (20 ml) added to the reaction mixture The toluene was evaporated, hexane was added to the residue and the precipitate, 5 * 5 g of the desired product, was filtered off After recrystallization from a mixture of hexane and toluene, the desired product had a melting point of 15 ° C.

EXAMPLE 3

This Example illustrates the preparation of the starting material 3-methyl-isopropylaniline.

3-Methylaniline (186 g) was dissolved in 600 ml of 85% by weight sulfuric acid. The mixture was heated to 80 ° C, then isopropyl alcohol (120 g) was added. The mixture was stirred at 80 ° C for 6 hours. After this period, the mixture was poured out on ice and ammonium hydroxide was added until the mixture was neutral. Diethyl ether was added and the ether extract was evaporated. The residue was distilled to give 110 g of the desired product which had a boiling point of 100 ° C at a pressure of 2.5 mm Hg.

EXAMPLE k - Selective herbicidal activity of the compound according to the invention;

Comparative test a)

In this experiment, the selective herbicidal activity in wheat of 3- (3-methyl-1-isopropylphenyl) -1,1-dimethylurea was compared to that of the commercial wheat herbicide isoproturon 3 - (^ - iso-30-propylphenyl) -1,1-dimethyl urea. Tests for the emergence of the plants were carried out with wheat, Triticum vulgare. type sapo, and post-emergence trials of the plants were performed on Maris Huntsman. The following weeds were tested:, 8 00 6 5 6 8 9 culture, Agronyron repens (Co); wild oats, Avena fatua / ludovi-ciana (Wo); ryegrass, Lolium multif lorum (Eg); annual meadow grass, Poa annua (Pa); brush grass, Agrostis tenuis (Bt); black grass, Alopecurus myosuroides (Am); wind blade, Apera spica venti 5 (Wg); wall, Stellaria media (St); speedwell, Veronica persica (Sw); cleavers, Galium aparine (Gg); knotweed, Polygonum lapathifolium (Pp); dead-nettle, Bami urn purpureum (Dn); herik,

Sinapis arvensis (Ck); fetid chamomile, Matricaria spp (Mw); shepherd's purse, Capsella bursa pastoris (Sp); poppy, 10 Papaver rhoeas (Po).

The active ingredients to be tested were processed into emulsifiable concentrates containing 20 wt. Active ingredient, 10 wt.% Of a mineral oil, emulsifying agents and xylene as a solvent. Each concentrate was diluted with water and test plants 15 were sprayed at doses of 6.0, 2.0, 0.6, 0.2. 0.06 and 0.02 kg / ha of active ingredient. For each dose, the test was repeated four times both before and after the emergence of the plants. The pre-emergence trials used untreated seeded soil for comparison, and the post-emergence trials used untreated soil in which seedlings were planted. The activity of the active components was visually determined in the post-emergence test after 21 days and in the pre-emergence test after 28 days and recorded on a 0-9 ascending scale. The rating 0 means no effect on the treated plants and the rating 9 indicates the death of the plants. At this scale, an increase of one unit on the linear scale corresponds to an increase of approximately $ 10 in efficacy.

The results obtained were subjected to a probit analysis, where parameters a and b were estimated by computer using the following formula:

Probit (f response) = a + b log (dose) 3006568 10

Using the obtained curve, dosages corresponding to a particular response can be calculated. In this Example, a G3U, -q, i.e. the dose at which a 50% response to the active ingredient 5 is obtained, was calculated for each weed.

The selectivity factor for wheat was calculated from the values obtained for each weed: (HD ^ q wheat selectivity factor 1 n-i + S -, ----, 'GIDj-g weeds

The higher the selectivity factor, the greater the selectivity of the herbicide.

Finally, the ratio of the selectivity factor for the compound of the invention to the selectivity factor for isoproturon was calculated. A value of more than 1 indicates that the compound of the invention is more selective than 15 isoproturon. The results are shown in Table 1, wherein the compound of the invention is indicated with A and isoproturon with I.

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8006568 12

Table 1 "shows that: 1. The compound of the invention is more selective than iso-proturon in 9 of the 12 weeds emerging from the plants and eleven out of 5 weeds tested after emergence.

2. The compound according to the invention has a much greater activity than isoproturon with regard to the commercially important weeds cultivated grass (a perennial grass), sticky herb and speedwell.

3. The compound according to the invention is on average 1.8 times. as selective as isoproturon when the pre-emergence compound is used and 2.5 times as selective as isoproturon when it is applied after the plants emerge.

Comparative test b)

A second trial was conducted comparing the selective herbicidal activity in wheat of 3- (3-methyl-1-isopropyl-phenyl) -1,1-dimethyl-urea with two other commercial urea herbicides, 3- (3-chloro- 1-methylphenyl) -1,1-di-20 methyl urea (chlorotoliron) and 3- (3-chloro-4-methoxyphenyl) -1,1-dimethyl urea (Metoxuron). The test performed prior to the emergence of the plants was made special, with the exception of the one below. said changes, the same method used as in the above comparative test a) carried out before the emergence of the plants. The following weeds were tested: * culture, Agropyron repens (Co); wild oats, Avena fatua / ludovi-ciana (Wo); raw grass, Lolium mult if lorum (Rg); annual meadow grass, Poa annua (Pa); witbol, Holcus lanatus (Yo); black grass, Alopecurus myosuroides (Am); sugar beet, Beta vulgaris (Sb); 30 wall, Stellaria media (St); speedwell, Veronica persica (Sw); convolvulus, Convolvulus arvensis (Cv); knotweed, Polygonum lapathifolium (Pp); herik, Sinapis arvensis (Ck). In this test, the results of the treatment after 20 days were visually determined and converted into selectivity factors, 8 006 56 8 13 as described in the above comparative test a), but now Chlortoluron was used as the standard material. That is, the selectivity factor The results obtained for Chlortoluron at each weed soil were divided into the values obtained for the other two compounds in the test, the ratio for Chlortoluron was set at 1. The results are shown in Table 2, the compound of the invention again with A, Chlortoluron with C and Metoxuron with M is indicated.

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As shown in Table 2, the compound of the invention is, on average, more than twice as selective as Chlorotoluron or Fluiduron when the compounds are tested for activity in wheat before plant emergence.

5 EXAMPLE 5 - Evaluation of the Efficacy of 3- (3-methyl-1 * -isonropylphenyl) -1,1-dimethylurea v

The efficacy and spectrum of the efficacy of 3- (3-methyl - ^ - isopropylphenyl) -1,1-dimethylurea and 3- (U-iso -propylphenyl) -1,1-dimethylurea (isoproturon) when enL emergence of the plants were compared in the UK on the basis of seven field trials in winter cereals. The tests were carried out on normal commercial winter wheat and winter barley, between which grass-like weeds and / or broad-leaved weeds grow naturally.

The formulations of the compound of the invention, 500 g / l suspension concentrate, and of isoproturon 500 g / l S.C.

(Hytane, 500 L) were diluted with water and each used in a similar series of four doses per test. The dosages used were 1.58, 2.10, 2.63 and k92 kg of active material / ha, corresponding to 3 / h, 1.11 / k and 2 times the commercially recommended dose of 2.1 kg am / ha isoproturon applied as a herbicide to winter cereals in the spring after the emergence of the plants. In three experiments (Hes. 5, 6 and 7), the compound of the invention was used with the addition of a spray agent to improve the properties of the formulation. The spraying agent was placed in a tank * with the compound of the invention mixed in a ratio of 2 parts of compound (a.m.) to 1 part of spray on a weight / volume basis.

Plots of land of 10 x 3 m were used and each treatment was repeated three times in a random block pattern.

The pesticide was applied to each plot using a gas pressurized sprayer with a spray volume of ^ 17 1 / ha. Details of the condition of the crop 8006568 16 and the conditions prevailing during each test during the application of the pesticide are listed in Table 3.

The health of the crop and the effect of the chemical treatment on grasses and grass weeds were established 1-3 months after treatment. The effect on the crop was determined visually and recorded on an ERWC scale from 0-9, with the rating 0 showing no effect and the rating 9 indicating the death of the crop. In the evaluation of the weed activity, a percentage was determined for the estimated effect against the weed weed, both for the total amount and per weed species most common on all plots. The results for the grassy weeds were determined by counting the number of tufts in 6 or 8 equal plots, measuring 0.5, and expressing these numbers for each plot 15 in flowers 0.5 m. For the following weeds and the results were determined: (a) crustaceous weed - speedwell, Veronica persica (Sw); wall, Stellaria media (St); stinking chamomile, Matricaria spp. (Mw); cleavers, Galium aparine (Gg); dead net el, Daminium purpurea (Dn) and h) grassy weeds 20 - black grass, Alopecurus mvosuroides (Am); wild oats, Avena spp. (Wed). Depending on the weather conditions, 138-169 days after the treatment was harvested using a combine and the grain weights of the crops harvested were determined.

The results of the field tests are reported in Table U 25 below as the average values of the results determined in the various field tests, ie the average of the results of all the different field tests was determined, so that in any case the average wiarde was obtained The reported result for the crop is the average value on the EWRC scale of the actual visual assessment made in the seven tests The reported action against weeds is expressed in the percentage decrease in weed growth. relative to those obtained in the comparison plots, as determined by the above techniques. The values for 8 006 56 8 17 "efficacy against all broadleaf weeds during the test were also reported, and the average value for all weeds in all tests is reported below head "Total dicots", if the rate of decline in the growth of the weeds relative to d The comparison plant. The harvest weight is expressed as a percentage of the harvest weight of the comparison plots * whose yield was set at $ 100.

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♦ 8006568

Claims (7)

1. 3- (3-Methyl-4-isopropylphenyl-1,1-dimethylurea. Process for the preparation of a compound according to claim 1, characterized in that the aniline of formula I or a hydrohalide salt thereof: V \ i * -c3HT-ί Q \ NH2 (I) 5 is reacted with: a) a dimethyl carbamoyl halide; or b) phosgene, to prepare the isocyanate of formula II: SCO (II) and at least part of the isocyanate is reacted with dimethylamine. Process according to claim 2, characterized in that process (a) is carried out in the presence of a dehydrohalogenating agent. t k. Process according to claim 2 or 3, characterized in that process (a) is carried out using dimethyl carbamoyl chlorofide. Herbicide preparation, characterized in that the preparation contains the compound according to claim 1, as well as a suitable carrier. 6. Preparation according to claim 59, characterized in that the preparation contains at least two carriers of which at least one is a surfactant. 8 00 6 5 6 8 3 7. Preparation according to claim 5 or 6, characterized in that the preparation also comprises one or more of the herbicides cyanazine, bnoylprop ethylflampropisopropyl or flampropmetbyl. contains. 8. Method for preventing unwanted plant growth in a field, characterized in that a compound according to claim 1 or a preparation according to any one of claims 5-7 is applied to the field, the plant, etc. *. t 8006568