DK154502B - PHENYLURINE INGREDIENTS, HERBICIDE PREPARATIONS CONTAINING THAT, AND A PROCEDURE TO COMPLETE WEEDS UNDER ITS USE - Google Patents

Description

DK 154502 B

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The present invention relates to a phenylurea derivative, herbicidal compositions containing it, and to a method of controlling weeds using it.

U.S. Patent No. 2,655,447 discloses an extremely broad class of 5 urea derivatives with herbicidal properties. In the more than 25 years since these compounds were made, much research has been conducted on the use of urea derivatives as herbicides. The most significant urea derivative is probably the compound 3- (4-isopropylphenyl) -1,1-dimethylurea sold under the name "Isoproturon". This compound is widely used in Europe for the control of weeds in winter areas. Its main advantages are that it is extremely active against a wide range of weeds and can be used for both pre- and post-emergencies in both autumn and spring. Its main disadvantage is that no commercially important 15 weeds, especially perennial large-leaf weeds, perennial grass weeds, cages and honorary awards are not combated.

It has now been found that a particular phenylurea derivative not specifically described in U.S. Patent No. 2,655,447 and which carries in the phenyl ring two specific substituents has particularly useful herbicidal properties.

The present invention therefore relates to the compound of the formula CH 3 iso-C 3 H 7 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea. This compound is particularly useful for the control, either pre- or post-emergence, of weeds that grow in cereal crops such as corn, barley 25 or, in particular, wheat. As can be seen from the data set out in Examples 4 and 5, this compound has particular advantages over the commercial herbicide isoproturon for weed control in wheat.

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Crops. Thus, the compound has been found to have improved selectivity in wheat compared to "Isoproturon" and other known urea herbicides, as well as improved efficacy in controlling cage nests and honorary prices compared to "Isoproturon". The compound of the above formula is prepared by the aniline of formula I

or a hydrohalide salt thereof is reacted with either a) a dimethylcarbamoyl halide, preferably the chloride, or

b) phosgene (COC3) to form the isocyanate of formula II

-A> - at least part of the isocyanate is reacted with dimethylamine.

Process variant a) can be performed in the presence or absence of a solvent. Suitable solvents include hydrocarbons and halogenated hydrocarbons, e.g. benzene, toluene or carbon tetrachloride. It is preferably carried out under substantially anhydrous conditions. Since the reaction is a condensation reaction involving the elimination of hydrogen halide, it is preferably carried out in the presence of a dehydrohalogenating agent; organic or inorganic bases are suitable; Sodium acetate has been found to be particularly useful when working without a solvent, and organic bases such as triethylamine or pyridine are useful when using a solvent. The reaction is preferably carried out at a temperature in the range of 0 to 80 ° C, conveniently at room temperature, and the reaction mixture can be worked up in conventional manner.

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Process variant b) is conveniently carried out in the presence of a solvent, e.g. a hydrocarbon such as toluene, at a temperature in the range of 80 to 120 ° C; The reaction may conveniently be carried out at the reflux temperature of the solvent used.

The resulting isocyanate of formula II may, if desired, be isolated from the reaction mixture, but it is preferably reacted in situ with dimethylamine. The reaction is conveniently carried out at a temperature in the range of 0 to 30 ° C, suitably at room temperature. The desired product can be isolated by any convenient method.

The present invention further relates to a herbicidal composition containing the above compound 3- (3-methyr-4-isopropyl-phenyl) -1,1-dimethylurea together with a suitable carrier. The invention also relates to a method for controlling undesirable plant growth 15 at a site by applying to the site a herbicide active compound or herbicide composition, comprising the compound or composition of the present invention.

In some cases, it may be desirable to mix the compound of the present invention with one or more other compounds having herbicidal activity, e.g. to change the spectrum of activity. Thus, the compound of the present invention can be admixed with other broad-spectrum herbicides such as 2- (4-chloro-6-ethylamino-5-triazin-2-ylamino) ~ 2-methylpropionitrile (the commercial herbicide "cyanazazine") or with more specialized narrow-spectrum herbicides such as fly oat herbicides of the alanine type described in British Patent Specification No. 1,164,160, including ethyl N-benzyl-N- (3,4-dichlorophenyl) -2-aminopropionate (the commercial herbicide "benzoylprop ethyl ") and the racemic mixture or (-) - isomer of isopropyl or methyl N-benzoyl-N- (3-chloro-4-fluorophenyl) -2-aminopropionate (the commercial herbicides" flamprop isopropyl "and" flamprop methyl ") .

A carrier in a composition of the present invention is any material with which the active ingredient is formulated to facilitate application to the site to be treated as

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4 e.g. may be a plant, seed or soil, or to facilitate storage, transport or handling. A carrier may be a solid or a liquid, including a material which is normally gaseous, but which is compressed to form a liquid, and any of the carriers normally used to formulate herbicidal preparations may be used. .

Suitable solid carriers include natural and synthetic clays and silicates, e.g. natural silicon dioxides such as diatomaceous earth, magnesium silicates such as talc, magnesium aluminum silicates such as atomic grits or vermiculites, aluminum silicates such as kaolinites, mont-morillonites or mica species, calcium carbonate, calcium sulfate, synthetic hydrated silicas or alumina, natural and synthetic resins such as coumarone resins, polyvinyl chloride and styrene polymers and copolymers, solid polychlorophenols, bitumen, waxes such as beeswax, paraffin waxes or chlorinated mineral waxes and solid fertilizers such as superphosphates.

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

25 Agricultural preparations are often formulated and transported in a concentrated form which is then diluted by the user before use. The presence of small amounts of a surfactant carrier facilitates this dilution process. Thus, preferably at least one carrier in a composition according to the present invention is a surfactant. The composition may e.g. contain at least two carriers, at least one of which is a surfactant.

A surfactant may be an emulsifier, dispersant or wetting agent, it may be nonionic or ionic. By way

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Suitable surfactants are the sodium and calcium salts of polyacrylic acids and lignin sulfonic acids, the condensation products of fatty acids or aliphatic amines or amides having at least 12 carbon atoms in the molecule with ethylene oxide and / or propylene oxide, fatty acid esters of glycerol, sorbitan, pentaerythritol, condensates thereof with ethylene oxide and / or propylene oxide, condensation products of fatty alcohols or alkyl phenols such as p-octylphenol or p-octylcresol with ethylene oxide and / or propylene oxide, sulfates or sulfonates of these condensation products, alkali metal salts, alkaline earth metal or alkaline earth metals, of sulfuric or sulfonic acid esters containing at least 10 carbon atoms in the molecule, e.g. sodium lauryl sulfate, sodium sec alkyl sulfates, sodium salts of sulfonated castor oil or sodium alkylarylsulfonates such as sodium dodecylbenzenesulfonate, and polymers of ethylene oxide and copolymers of ethylene oxide and propylene oxide.

The compositions of the present invention may e.g. are formulated as wettable powders, powders, granules, solutions, emulsifiable concentrates, emulsions, suspension concentrates or aerosols. Wettable powders usually contain 25, 50 or 75 weight percent active ingredient and usually contain, in addition to solid inert carrier, 3-10 weight percent dispersant and, if necessary, 0-10 weight percent stabilizer (s) and / or other additives such as penetrating agent. or adhesives. Powders are usually formulated as a powder concentrate having a similar composition to a wettable powder, but without a dispersant, and diluted by the use of additional solid carrier to form a composition which usually contains 0.5-10% by weight of active ingredient. Granules are usually prepared with a size of between 10 and 100 BS mesh (1.676 - 0.152 mm) and can be prepared by agglomeration or impregnation techniques. In general, granules contain 0.5 - 25% by weight of active ingredient and 0 - 10% by weight of additives such as stabilizers, slow release modifiers or binders. Emulsifiable concentrates usually contain, in addition to solvent and, if necessary, co-solvent 10 - 50 35 w / v% active ingredient, 2-20 w / v% emulsifiers and 0 - 20 w / v% other additives

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6 such as stabilizers, penetrants or corrosion inhibitors. Suspension concentrates are usually formulated to provide a stable, non-settling liquid product and usually contain from 10 to 75% by weight of active ingredient, from 0.5 to 15% by weight, 5% dispersants, from 0.1 to 10% by weight of suspending agents such as protective colloids or thixotropic agents, 0-10% by weight of other additives such as anti-foaming agents, corrosion inhibitors, stabilizers, penetrants or adhesives and water or an organic liquid wherein the active ingredient is substantially insoluble, with certain organic solids or inorganic salts being present dissolved in the formulation to help prevent sedimentation or as antifreeze agents for water.

Aqueous dispersions or emulsions, e.g. compositions prepared by diluting a wettable powder or concentrate of the present invention with water are also within the scope of the present invention. These emulsions may be water-in-oil or oil-in-water type and have a thick "mayonnaise" -like texture.

The compositions of the present invention may also contain 20 other ingredients, e.g. other compounds that have insecticidal or fungicidal properties.

The present invention is further illustrated by the following examples: EXAMPLE 1 Preparation of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea 7.4 g of 3-methyl-4-isopropylaniline and 0.5 g of anhydrous sodium acetate is stirred. together as a solid mixture and over 15 minutes 5.4 g of dimethylcarbamoyl chloride are added. The mixture is left at room temperature overnight and then treated with water followed by extraction with methylene chloride. After drying over magnesium sulfur 7

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The solvent is evaporated off and the resulting solid is recrystallized from a mixture of hexane and toluene. There is obtained 3.5 g of the desired product, mp 153 - 154 ° C.

Calculated for C 70.9 H 9.1 N 12.7

Found: C 69.9 H 9.1 N 12.1 Example 2

Alternative preparation of the compound of the present invention 10 g of 3-methyl-4-isopropylaniline (80% purity) in 150 ml of toluene are heated at reflux while passing COC gas through the solution for approx. For 1 1/2 hour, then dry nitrogen is passed through the solution to remove excess COC 2. After cooling to room temperature, 5 g of dimethylamine are added in 20 ml of toluene to the reaction mixture. The toluene is evaporated, to the residue is added hexane and the precipitate, 5.5 g of the desired product, is filtered off. After recrystallization from a mixture of hexane and toluene, the desired product has a melting point of 154 ° C.

EXAMPLE 3

This example illustrates the preparation of the starting material 3-Methyl-4-isopropylaniline 186 g of 3-methylaniline is dissolved in 600 ml of 85% by weight sulfuric acid. The mixture is heated to 80 ° C and then 120 g of isopropyl alcohol is added. The mixture is stirred at 80 ° C for 6 hours. At the end of this time, the mixture is poured onto ice and 25 ammonium hydroxide is added until the mixture is neutral. Diethyl ether is added and the ether extract is evaporated. The residue is distilled to give 110 g of the desired product, boiling point 100 ° C / 2.5 mm Hg.

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EXAMPLE 4

Selective herbicidal action for the compound of the present invention

Comparative Test (a) 5 This test compares the selective herbicidal action of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea in wheat with the action of the commercial wheat herbicide isoproturon, 3- (4-isopropylphenyl) - 1, 1-dimethylurea. Pre-emergent tests are performed on wheat, Triticum vulgare variety sappo, and post-emergent tests 10 are performed on the variety Manis Huntsman. The weeds tested are as follows: mercury, Agropyron repens (Co); flying oats, Avena fatua / -ludoviciana (Wo); ryegrass, Lolium multiflorum (Rg), annual grasses, Poa annua (Pa), when. Agrostis tenuis (Bt), Aiopecurus myosuroides (Am); Apera spica venti (Wg), bird grass, Steliaria media 15 (St); honorary award, Veronica persica (Sw); wall cage, Galium aparine (Gg); pale peach herb, Polygonum lapathifolium (Pp); dead nettle,

Lamium purpureum (Dn); agar mustard, Sinapis arvensis (Ck); Matricaria spp (Mw); shepherd's bag, Capseila bursa pastoris (Sp); poppy, Papaver rhoeas (Po).

The active test ingredients are prepared as emulsifiable concentrates containing 20% by weight of active ingredient, 10% by weight of a mineral oil, emulsifiers and xylene as solvent. Each concentrate is diluted with water and the test plants are sprayed at doses of 6.0, 2.0, 0.6, 0.2, 0.06 and 0.02 kg / ha of active material. Twenty-five tests are performed for each dose, and both pre- and post-emergent tests are performed. In the pre-emergent tests, untreated sown soil and in the post-emergent tests untreated soil containing seedlings are used as controls. After 21 days in the post-emergent test and 28 days in the pre-emergent test, the efficacy of the active ingredients is assessed visually on a 0 - 9 scale; where a rating 0 indicates growth as with untreated control, and a rating 9 indicates death. With this rating scale, an increase of 1 unit on the linear scale corresponds to approx. 10% increase in the level of effect.

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The results obtained are subjected to a probit analysis whereby a computer estimates the parameters a and b in a relation with the form:

Probit (% response) = a + b log (dose).

Using the resulting curve, doses corresponding to a given response level can be calculated. In this example, a GID ^ q value, i.e. the dose required to give a 50% response to the active ingredient for each species.

From the values obtained, a selectivity factor for each weed plant is calculated in comparison with wheat: 10 GID ^ Q value (wheat) seed activity factor = GID ^ Q value (weed plant)

The greater the selectivity factor, the more selective the herbicide is.

Finally, the ratio of the selectivity factor of the compound of the present invention to the selectivity factor of isoproturon is calculated. A value greater than 1 indicates that the compound of the present invention is more selective than isoproturon. The results are listed in Table I, where the compound of the present invention is designated "A" and isoproturon is designated as 20 Ί ".

Table I

Pre-erncrgens test

Plant species GID value Value Selection factor Selection factor ratio I A I A

25 _______

Wheat 1.23 1, Q7

Co 1.99 1.05 0.6 1.6 2.7

Wed 0.60 0.59 2.1 2.8 1.3 30 Rg 0.07 0.16 17.6 9.3 0.5

Pa 0.06 0.08 20.5 20.9 1.0

Table continued

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Bt 0.02 0.02 61.5 83.5 1.4

Am 0.10 0.18 12.3 9.3 0.8

Wg - - - 5 St 0.11 0.14 11.2 11.9 1.1

Sw 0.48 0.18 2.6 9.3 3.6

Gg 1.87 0.91 0.7 1.8 2.6

Pp 0.37 0.24 3.3 7.0 2.1

Dn 0.15 0.10 8.2 16.7 2.0 10 Ck 0.17 0.08 7.2 20.9 2.9

Mw '-

Sp - -

Po - 15 Mean 1.8

Post-emergence test GID value g Selection factor Selection factor

Wheat 1.69 1.67 - 25 Co 0.93 0.61 1.81 2.7 1.5

Wed 0.14 0.19 12.1 8.8 0.7

Rg 0.16 0.21 10.6 8.0 0.8

Pa 0.05 0.03 33.8 55.7 1.7

Bt 0.08 0.02 21.1 83.5 4.0 30 Am 0.04 0.06 42.3 27.8 0.7

Wg 0.04 0.07 42.3 23.9 0.6

St 0.08 0.06 21.1 27.8 1.3

Sw 1.10 0.27 1.5 6.2 4.0

Gg 2.42 0.46 0.7 3.6 5.2 35 Pp 0.25 0.07 6.8 23.9 3.5

Dn 0.41 0.18 4.1 9.3 2.3

Ck 0.011 0.006 96.7 176.2 1.8 11

Table continued

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Mw 0.12 0.5 14.1 33.4 2.4

Mp 0.11 0.015 14.2 105.7 7.5

Po 0.001 0.001 - 5 ______-

Average 2.5

It can be seen from Table I: 1) The compound of the present invention is more selective 10 than isoproturon in 9 of the 12 pre-emergent tested weeds and 11 of the 15 post-emergent tested weeds.

2) The compound of the present invention is far more active than isoproturon on the commercially important weed plants of mercury (a 1-year-old weed plant), cage seed and honorary price.

3) The compound of the present invention is on average 1.8 times as selective as isoproturon when used pre-emergent, and 2.5 times as selective as isoproturon when applied post-emergent.

Comparison test b).

Another test is performed in which the selective herbicidal action in wheat of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethylurea is compared with two other commercial urea herbicides, 3- (3-chloro-4-methane). thoxyphenyl) -1,1-dimethylurea (Chlorotoluron) and 3- (3-chloro-4-methylphenyl) -1,1-dimethylurea (Metoxuron). The method used in this pre-emergent test is identical to that described in Comparative Test (a) above for the pre-emergent test except for the modifications specified below. The tested weed species are the following: mercury, Ag ropy ron repens (Co), flying oats, Avenafatua / Ludoviciana (Wo), ryegrass, Lolium multiflorum (Rg), 30 annual meadow grass, Poa annua (Pa), velvet grass, Holcus lanatus (Vo ),

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Alopecurus myosuroides (Am), sugar beet, Beta vulgaris (Sb), bird grass, Stellaria media (St), honorary prize, Veronica persica (Sw), convolvulus, Convolvulus arvensis (Cv), pale peach-herb, Polygonum lapathifolium (Pp), agar , Sinapis arvensis (Ck). In this test, treatment results are visually assessed after 20 days and these test results are converted to selectivity factors as described in Comparative Test (a) above except that in this case Chlorotoluron is used as standard. That is, the selectivity factor obtained for each weed species with Chlorotoluron is divided up by 10 into the values obtained with the other two compounds in the test; the ratio of Chlorotoluron is then added to 1. The results are given in Table II, where the compound of the present invention is again referred to as "A", Chlorotoluron as "C" and Metoxuron as "M".

Table II

15 Plan- GID50 value. Selection factor Selection factor ratio tea rt____

CMACMA CMA

Wheat 2.11 1.54 2.13 - - - 1 1 1 20 ____

Co 1.71 3.23 1.36 1.23 0.48 1.57 1.00 0.39 1.28

Wed 1.58 0.82 0.58 1.34 1.88 3.67 1.00 1.40 2.74

Rg 0.51 0.49 0.44 4.14 3.14 4.84 1.00 0.76 1.17

Pa 0.19 0.22 0.11 11.11 7.00 19.36 1.00 0.63 1.74 Yo 0.19 0.19 0.14 11.11 8.11 15.21 1, 0.73 1.37

At 0.33 0.87 0.26 6.39 1.77 8.19 1.00 0.28 1.28

Sb 0.54 0.46 0.17 3.91 3.35 12.53 1.00 0.86 3.20

St 0.03 0.03 0.03 70.33 51.33 71.00 1.00 0.73 1.01

Sw 0.45 0.29 0.19 4.69 5.31 11.21 1.00 1.13 2.39 30 Cu 0.25 0.15 4.48 8.44 10.27 0.48 1, 00 1.22 0.06

Pp 1.28 0.64 0.90 1.65 2.41 2.37 1.00 1.46 1.44

Ck 0.67 0.24 0.10 3.15 6.12 21.30 1.00 2.04 6.76

Mean 1.00 0.97 2.04 __: __

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As shown in Table II, the compound of the present invention is on average more than twice as selective as either chlorotoluron or methoxuron when applied pre-emergent in wheat.

EXAMPLE 5 Market study of 3- (3-methyl-4-isopropylphenyl) -1,1-dimethyl-urea

The efficiency and spectrum of activity of post-emergent application of 3- (3-methyl-4-isopropylphenyl) 1,1-dimethylurea and 3- (4-isopropylphenyl) -1,1-dimethylurea (isoproturon) are compared by a total of 7 10 field trials in winter cereals In the UK. The experiments are carried out in normal commercial crops of winter wheat and winter barley, in which common occurrences of grass weeds and / or broadleaf weeds are present.

The formulations of the compound of the present invention, 15,500 g / liter suspension concentrate, and of isoproturon, 500 g / liter suspension concentrate (Hytane 500L), are diluted with water and each applied in a corresponding amount of 4 doses in each experiment. The doses used are 1.58, 2.10, 2.63 and 4.2 kg of active material / ha, which is equivalent to 3/4, 1, 1 1/4 and 2 times the commercially recommended dose of 2, 1 kg of active material / ha of isoproturon applied as a post-emergent herbicide in winter crops in the spring. In three experiments (5, 6 and 7), the compound of the present invention is applied together with a spray adjuvant to improve the formulation properties. The syringe adjuvant is applied as a tank mixture with the compound of the present invention in a ratio of 2 parts compound (active ingredient) to 1 part syringe adjuvant on a weight / volume basis.

Pots with dimensions of 10 m x 3 m are used and each treatment is repeated three times in a randomized block trial. The applications are performed on each soil using a small soil spray below.

30 gas pressures at a spray volume of 417 liters / ha. Details of crop stages and application conditions are given for each experiment in Table III.

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Crop condition assessments and chemical treatment efficacy on grasses and broadleaf weeds are performed between 1 and 3 months after treatment. The crop impact is assessed visually on the 1 - 9 scale according to the EWRC (European Weed Research Counsil), where the value 0 equals no effect and value 9 corresponds to the death of the crop. The weed assessments include estimation of the percentage total coverage of broadleaf weeds and of species for the dominant weed species obtained on all the test plots. The weed species are evaluated by counting the number of tufts in six or eight equal soil plots-10 at 0.5 x 0.5 meters and translating these into numbers of small flowers in each lot. The weeds considered are: (a) broadleaf weeds, honorary awards, Veronica persica (Sw), bird grass, Stellaria media (St), Matricaria spp. (Mw), cucumber nettle, Galium aparine (Gg), twig, Laminium purpurea (Dn) and b) grass weed - Alopecurus myrosuroides (Am), 15 flying oats, Avena spp. (Wo). Depending on climatic conditions, the crops are harvested between 138 and 169 days after treatment using a combine harvester and the grain weight of the harvested crops is determined.

The results of the test are shown in Table IV below. Results 20 are given as average or mean values for each of the evaluated effects in the different field experiments, ie. the results from all the different field trials midies together to form a mean in each case. The crop impact indicated is the mean on an EWRC scale for the actual visual assessments made in the seven experiments. The values for efficacy against weeds stated are in percent reduction of weed growth over that obtained in control weights by measurement by the technique described above. The efficacy values for all broadleaf weeds in the test are also indicated, and this mean for all weeds in all tests 30 is given under the heading (total two-leaf foliage) as the percentage reduction in weed growth relative to control. The crop weight is expressed as a percentage of the crop weight yield from the control weights, with the control soil yield being set to 100%.

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Table III

For- Crop- Variety Such Soil- Crop- Tem-% Moisture-soil search they (business- Establishment- Soil-% no. No. Date, date of humidity 5 years) (cf. by tig-equivocation applied to addiction, lent

for) ° C

10 1 winter- Sports 26. 26. C, D 10.7 27.1 26.0 34 wheat man Sept. March 2 winter- Sonja 10. 28. A, F 6 28.1 23.5 29 barley oct. February

3 winter- M. Hob- 9. 3. A, D 5 28.3 31.2 44 15 wheat bit oct. March 4 Winter- Hustler 17. 3. A, E 4.5 22.3 33.5 41 Wheat Oct. March 5 Winter- Flan- Oct. 3. A 9.9 38.6 36.1 52 wheat April 20 6 winter Flan- 11. 3. C, D, G 10.0 18.6 16.9 18 wheat October. April 7 winter- Mitob 18. 3. B, D 10.0 16.1 16.8 16 wheat bit Oct. April 25 Crop stage key: A - 5 leaves unfolded (seedling) B - 5 leaves unfolded (seedling) C - 7 leaves unfolded (seedling) D - head shoots and 2 tillers (tiller) (30 shoots) F - head shot and 4 bite shoots (staging stage) G - pseudo stalk extension (stem extension stage).

Lose! IV

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Test Do-Off- Weed Efficiency Crop-Combined Crop Grasses Broad-leaved weed crop (kg de-:: weight 5 am / effect- Am Wo Sw St Mw Gg Dn Two% of ha) counted con - EWRC totrol scale germinated 3- (3-meth 1.58 2.2 79.1 19.4 75.3 95.3 93.4 56.0 65.2 82.2 129.9 yl-4-iso-2.10 2.3 87.2 27.6 80.2 95.5 94.1 70.6 53.8 85.0 138.8 propyl 2.63 2.2 93.2 33.0 85.5 98.9 94.5 67.0 66.8 90.1 141.8 phenyl) - 4.20 2.4 97.7 53.2 89.7 99.6 98 0 92.8 77.3 94.4 136.1 1.1-Dimethylurin Substance 3- (3-Iso-1.58 2.2 85.9 21.7 45.1 96.2 95.1 8 , 0 49.8 70.1 134.8 Propyl 2.10 2.1 90.3 34.0 50.0 97.6 99.2 2.5 43.4 72.9 136.6 Phenyl) - 2.63 2.0 93.5 36.1 43.6 98.8 100.0 20.3 45.5 73.4 130.1 1.1-di-4.20 2.2 97.9 48.9 52 , 9 99.8 87.7 21.072.078.7134.5 Methyl urea Control - 2.6 - - - - - - - 100

Claims (4)

Herbicidal composition, characterized in that it contains the compound of claim 1 together with at least one suitable carrier. Composition according to claim 2, characterized in that it contains at least two carriers, at least one of which is a surfactant. Composition according to claim 2 or 3, 10, characterized in that it further contains one or more herbicides selected from 2- (4-chloro-6-ethylamino-s-triazine-2-ylamino) -2-methylpropionitrile, ethyl N-benzyl-N- (3,4-dichlorophenyl) -2-aminopropionate and the racemic mixture or (-) - isomer of isopropyl or methyl N-benzoyl-N- (3-chloro-4-fluorophenyl) -2 aminopropionate. A method for controlling undesirable plant growth at a site by applying to the site a herbicidal active compound or herbicide composition, characterized in that the compound is according to claim 1 and the composition is according to any of claims 2 to 5. 4th