HU189497B - Herbicide compositions containing derivatives of 2-halo-acetanilides as active substances - Google Patents

Abstract

The invention relates to a group of N-hydrocarbylox-methyl-2-haloacetanilide compounds, herbicidal preparations which contain these compounds as active ingredient, and to methods of using these herbicides in various crops, in particular maize and soybeans, but also other crops such as e.g. Cotton, peanuts, oilseed rape, bush beans, wheat and sorghum. The herbicides of the present invention are particularly effective against heavy-killers of several years old such as Wheatgrass and Cyperaceae, but are also effective against annual weeds.

Description

FIELD OF THE INVENTION The present invention relates to herbicidal compositions containing the 2-haloacetanilide derivatives of formula (I) as an active ingredient.

Numerous publications have already been published in the art regarding 2-haloacetanilide derivatives. These 2-haloacetanilide derivatives may be substituted or unsubstituted on the anilide nitrogen atom and / or the anilide ring, for example with alkyl, alkoxy, alkoxyalkyl or halogen atoms.

Compounds closely related to the active ingredients of the herbicidal compositions of the present invention which contain a hydrocarbyloxymethyl group on the anilide nitrogen atom, a trifluoromethyl group in one ortho position and a methyl group in the other ortho position are described in Belgian Patent 810,763. disclosed. This patent describes N-alkoxyethyl or alkyl substituted alkoxyethyl 2-chloroacetanilides which may be substituted in the ortho and meta position of the anilide ring by one or more groups which are halogen, alkyl, alkoxy or trifluoromethyl groups (-CF ₃ ). II. Table I provides compounds that are substituted with -CF _{3 in} one ortho position and unsubstituted in the other ortho (compounds 37-48) and also contain compounds that contain a -CF ₃ substituent at one meta-position. they are unsubstituted at the ortho position and substituted at the other ortho position with a methoxy group (compounds 22-25) or a chlorine atom (compounds 33-36). However, Belgian Patent 810,763 does not mention 2-haloacetanilide derivatives which are substituted in one ortho position by a -CF ₃ group and in another ortho position by a methyl or ethyl group, as in the compounds of formula I . In addition, the compounds disclosed in Belgian Patent No. 810,763 are characterized in that an alkoxyalkyl group replaces the nitrogen atom of the anilide in which the alkylene moiety must have at least two carbon atoms between the nitrogen atom and the oxygen atom of the alkoxy moiety. In contrast, the compounds constituting the active ingredient of the herbicidal compositions of the invention are further characterized in that they are partially substituted by alkoxymethyl on the nitrogen atom of the anilide. The significance of the differences between the compounds disclosed in Belgian Patent No. 810,763 and the active ingredients of the herbicidal compositions of the invention becomes apparent when considering the comparative herbicidal data provided in the patent, which fully substantiate the beneficial effects of the active ingredients of the herbicidal compositions. selectivity, spectrum of herbicides, and crop protection.

Other references which are less closely related to Belgian Patent No. 810,763 include U.S. Patent Nos. 3,966,811 and 4,152,137, German Patent 2,402,983, British Patent 2,013,188, and U.S. Pat. 0767th South Africa. Although these descriptions are 2-halo2 '

-acetanilides which contain -CF ₃ substituents on the anilide ring, among other substituents, are referred to only in U.S. Pat. No. 3,966,811 and 74/0767. U.S. Patent Nos. 5,198,198 to 5,198. However, it is noted that neither U.S. Pat. No. 3,966,811 nor U.S. Pat. South African Patent Application No. 3,244,198 does not cover compounds which are substituted in the ortho position by trifluoromethyl in general or in particular which are substituted in the other ortho position by methyl or ethyl, the only CF ₃ substituted compounds being those derivatives, which are in the meta-position substituted by -CF ₃ . In addition, as in Belgian Patent 810,763, both U.S. Patent No. 3,966,811 and 74/0767. The South African Patent No. 5,123,125, requires that there be at least two carbon atoms between the nitrogen of the anilide and the oxygen of the alkoxy moiety. This is a requirement included in all prior art patents except U.S. Patent 4,152,137, which, as mentioned, does not contain CF ₃ substituted compounds.

Of the closest patents mentioned, only Belgian Nos. 810,763 and 74/0767. U.S. Patents Nos. 5,768,198 to 9,101,115 and 4,102,115 contain herbicidal data on N-alkoxyalkyl-2-haloacetanilides substituted with -CF ₃ on the anilide ring. These descriptions are also vague, indefinite and incomplete, for example, Belgian Patent No. 810,763 has limited herbicide data for only one CF _3- substituted derivative, compound 37 (shown in Fig. 2). 2-trifluoromethyl-N- (2'-methoxyethyl) -2-chloroacetanilide. Belgian patent application No. 810 763, Part II. Table 37 shows that active ingredient 37 kills or severely damages certain unnamed Cyperus varieties, Setaria, Digitaria and Echinochloa, lesser damage to Avena fatua weeds and unnamed Lolium varieties in certain crop plants. The fact that five of the six weeds used in the study were not named does not allow an evaluation of the herbicidal activity of Compound 37.

Similarly, in 74/0767. only provide a limited herbicidal data and those substituted compound only one _CF3 group, namely No. 78 2,6-dimethyl-3-trifluoromethyl-N- (2'-methoxy as well South African patent No. ethyl) -N-2-chloroacetanilide. Herbicide data for Compound 78 is described in Example 5, wherein Compound 78 is claimed to exhibit high growth inhibitory activity against four grass weeds. In addition, neither laboratory nor field test results are reported in 74/0767. South African Patent Application No. Ha-21

189 497, nor the selective control of weeds between crops, which makes it impossible to evaluate this active substance on the basis of such limited data. In addition, those closest to those references, while talking about herbicidal activity against a wide variety of weeds, do not provide any data on N-alkoxyalkyl-substituted CFCs that are shown to inhibit or inhibit either It is suppressed by hard weeds that live among one or more crop plants, such as common wheat, yellow and purple slabs, as well as annual broadleaf weeds and hardy weeds such as sorghum, shredded reed, texas and wild millet), red rice and itch (Raoulgrass), while suppressing or inhibiting other harmful perennial and annual weeds such as kelp, peppermint, goose, porcupine, brushwood, kujjas foxtail, barnyardgrass, morningglory, velvetleaf, tarlófű, purslane, hemp, silk, prickly sida, and the like increase.

Herbicides would have the very useful and desirable property of being able to maintain their herbicidal activity over long periods of production. The herbicidal formulations mentioned above are able to maintain their herbicidal activity for only 2 or 3 weeks, or in some extreme cases 4-5 weeks, before the active ingredient loses its phytotoxic properties. Accordingly, one of the disadvantages of prior art herbicidal compositions is that they remain relatively short-lived in soil.

Another disadvantage of the herbicidal compositions described above, in addition to their short-term action in soil or their action under normal weather conditions, is that their herbicidal activity is lost in the event of heavy rainfall, i.e. the herbicidal compositions are inactivated.

A further disadvantage of the aforementioned herbicidal compositions is that their use is limited to certain types of soils, for example, some herbicidal compositions are effective only in soils with low organic matter content, while they are ineffective in soils with high organic matter content and vice versa. Therefore, it is preferred that a herbicidal composition be used in all types of soil, such as light organic soil to heavy soil, including compost soil.

A further disadvantage of the herbicidal compositions mentioned in the preceding patents is that they are effective only in certain actual applications, such as pre-emergence surface application or soil mixing, pre-emergence and / or post-emergence application. Very advantageous are herbicidal compositions which are effective for any application, both for topical application and for application in soil.

Finally, some herbicidal compositions are disadvantageous because they require certain treatments because of their toxic nature. Therefore, it is a further requirement that herbicidal formulations be safely handled.

The present invention thus relates to herbicidal compositions which do not suffer from the above-mentioned disadvantages and which offer a variety of advantages within a single herbicidal composition.

The compositions according to the invention have the advantage, inter alia, of controlling and / or suppressing the aforementioned perennial and annual weeds, while not adversely affecting the crop or a substantial part thereof, in particular harm to maize and soybeans and other crop plants such as cotton. , peanuts, rape, beans, wheat and / or sorghum.

A further advantage of the herbicidal compositions according to the invention is that they remain active in the soil for up to 12 weeks.

The herbicidal compositions according to the invention are also advantageous because they are resistant to washing away and expansion due to high humidity, such as heavy rainfall.

A further advantage of the compositions of the invention is that they retain their herbicidal action over a long period of time in a variety of soils, including light organic matter, heavy clay soil and compost soil.

Advantages of the herbicidal compositions of the invention include that they are well suited for a variety of applications, such as surface application prior to emergence and incorporation into soil.

Finally, the advantageous property of the herbicidal compositions of the invention is that they are safe and do not require any special treatment.

The present invention relates to a herbicidal composition comprising 2-haloacetanilide derivatives as an active ingredient. The invention also relates to the control of live weeds between crop plants by the compositions of the invention.

It has now been found that herbicides containing a selective group of 2-haloacetanilide derivatives as active ingredients which contain a hydrocarbyloxymethyl group on the anilide nitrogen, but also contain a trifluoromethyl group at one ortho position and containing a methyl or ethyl group or a halogen in the other ortho position, they exhibit unexpected superior herbicidal properties as compared to herbicidal compositions known to date and described in the literature, including the closest herbicidal compositions.

The primary characteristic of the herbicidal compositions of the present invention is to control a wide range of weeds, including weeds that have not been able to control the herbicidal compositions used so far, and to control most of the weeds which are individually and / or collectively not vol3

189,497 can be controlled with agents of a single class of known herbicidal formulations, while being safe to handle and not harmful to crop plants such as corn and soybeans, but not to other crops such as cotton, peanuts, rape, wheat and bush beans. The herbicidal compositions protected in these patents have been found to be useful in inhibiting the development of a number of weeds, including certain resistant weeds, and the herbicidal compositions of the present invention also greatly inhibit the growth of resistant perennial and annual weeds. Examples of perennial weeds are black wheat, yellow and purple slate, broadleaf weeds such as spiny marshmallow, silk hemp, peppercorn, goose, hen and wild grasses such as gorse, sycamore, sycamore, silkworm, other harmful perennial and annual weeds, such as fallow millet, wormwood, cockroach and similar weeds. The resistance of the weeds can also be reduced by the herbicidal agents of the invention, such as ragweed, marshmallow, duckweed, stubble grass, and porcine.

The active compounds of the herbicidal compositions according to the invention are 2-haloacetanilide derivatives of the formula I. In this formula

- R is an alkyl, alkoxyalkyl, alkenyl or alkynyl group containing from 1 to 5 carbon atoms, and

- R, hydrogen, methyl or ethyl, provided that when R 1 is hydrogen, R is isopropyl and when R 1 is ethyl, R is ethyl, n-propyl or isopropyl.

Preferred compounds of formula (I) are those wherein, in formula (I), R is methyl or ethyl and R ₂ is C 2 -C 4 alkyl.

Among the active compounds of the formula I, the following compounds are preferably used in the herbicidal compositions according to the invention:

N- (ethoxymethyl) -2 '- (trifluoromethyl) -6'-ethyl-2-chloroacetanilide,

N- (n-propoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide,

N- (isopropoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide,

N- (isobutoxymethyl) -2'-trifluoromethyl-6'-fluorophenoxy) methyl-2-chloroacetanilide,

N- (ethoxymethyl) -2 '- (trifluoromethyl) -6'-ethyl-2-chloroacetanilide,

N- (n-propoxymethyl) -2 '- (trifluoromethyl) -6'-ethyl-2-chloroacetanilide, and

N- (isopropoxymethyl) -2 '- (trifluoromethyl) -6 ^, ethyl-2-chloroacetanilide.

Other agents of the herbicidal compositions according to the invention of the formula I will be described below.

The use of herbicidal formulations containing the active compounds of formula (I), their composition and methods of administration are described below.

The active compounds of the formula I according to the invention may be prepared by N-alkylation of the anion of a suitable secondary 2-haloacetanilide derivative under alkaline conditions. The preparation is exemplified in Example 1. A modified version of the N-alkylation process consists in the preparation in situ of halomethyl alkyl ethers which are used as starting materials in the N-alkylation process. This variation of the process is exemplified in Example 2 and thus illustrates other methods of preparing the active ingredients.

Example 1

This example describes the preparation of N- (ethoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide. In a 500 mL round bottom flask equipped with a mechanical stirrer and thermometer, 4.02 g (0.016 mol) of 2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide, 3.02 g (0.032 g) were mixed. mole) of chloromethylethyl ether and 2.0 g of benzyltriethylammonium bromide (which acts as a phase transfer catalyst) in 75 ml of methylene chloride. Then, 15 ml of a 50% strength aqueous sodium hydroxide solution were added with vigorous stirring. The exotherm causes the temperature to rise to 26 'C. Gas chromatography indicated that the reaction was complete in about 5 minutes. After 15 minutes, ice and water were added to the reaction mixture, the layers were separated, the organic layer was washed with 2.5% sodium chloride solution, dried and the solvent was evaporated. This gives a dark residue which is distilled using a ball-cooler. The resulting 3.4 g of a yellow oily fraction, boiling at 110 ° C to 115 ° C, is collected. This fraction was taken up in cyclohexane and purified by high performance liquid chromatography using 20% ethyl acetate in cyclohexane. The main fraction was further distilled using a ball-cooler to give 3.2 g (65% yield) of a colorless oil, b.p. 100-110 ° C (13.3 Pa), which crystallized as a white solid upon standing.

OP. 41-13 'C.

Analysis for C ₁₃ H ₁₅ ClF ₃ NO ₂ (%)

Calculated: C, 50.41; H, 4.88; N, 4.52;

Found: C, 50.02; H, 4.81; N, 4.38.

Example 2

This example illustrates another embodiment of the compounds of formula (I). A feature of the process variant is that the alkylating agent is formed in situ to provide a more efficient, economical and simple method.

7.3 g (0.096 mol) of ethylene glycol monomethyl ether and 1.44 g (0.048 mol) of para-formaldehyde are slurried in 100 ml of methylene chloride and the suspension is cooled in an ice-water bath and 5.9 g (0.048 mol) are added. mole) of acetyl bromide was added. Else-41. Stir 189,497 g for 45 min, then add 4.03 g (0.016 mol) of 2'-trifluoromethyl / -6'-methyl-2-chloroacetanilide and 2.0 g of benzyl triethylammonium chloride.

To the resulting mixture was then added 50 ml of 50% aqueous sodium hydroxide solution all at once. ® The reaction is complete in about 5 minutes by gas chromatography. Ice and water are then added to facilitate phase separation. The organic layer was separated, dried, filtered and the solvent was evaporated. Thus mO Don ¹⁰ 4.2 g of a clear, colorless oil having a boiling point of 150-160 ° C / 6.7 mmHg Analysis for C ₁₄ H ₁₇ C1F ₃ NO ₃ Found (wt%)

Calculated: C, 49.49; H, 5.04; N, 4.12;

Found: C, 49.33; H, 5.04; N, 4.08. ¹⁵

The product was identified as N- (2-methoxyethoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide.

In the case where ²⁰ vé- gauze then various pollutants may be formed at the N-alkylation is too high or too low a temperature, e.g., secondary anilide, corresponding imidate, amide or α-alkoxy-diketo-piperazines. These impurities can be removed from the organic layer by washing with dilute aqueous saline or acid, preferably 2-3% aqueous sodium chloride or 51% hydrochloric acid.

3-13. example

Substantially following the procedure described in Example 1 or 2, using the same amount of reagents and working under the same reaction conditions, the secondary anilide and the alkylating agent are varied according to the desired products to give other derivatives of formula (I). These agents are summarized in Table I below.

/. spreadsheet

The serial number of the example Identification of the active substance Experience formula Fp, C (Pa) Element Analysis calculated found 3 N- (isopropoxymethyl) -2 '- (trifluoromethyl) -2-chloro- C ₁₃ H _1S F ₃ C1NO ₂ 100-101 C 50.41 50.52 acetanilid (6.7) H 4.88 4.89 N 4.52 4.46 4 N- (n-propoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2- C ₁₄ H ₁₇ C1F ₃ NO ₂ 110-120 C 51.94 51.80 chloroacetanilide (13.3) H 5.29 5.17 N 4.33 4.28 5 N- (isopropoxymethyl) -2 '- (trifluoromethyl) -6' C ₁₄ H ₁₇ C1F ₃ NO ₂ 110-120 C 51.94 51.69 methyl 2-chloro-acetanilide (13.3) H 5.29 5.23 N 4.33 4.22 6 N- (isobutoxymethyl) -2 '- (trifluoromethyl) -6'-methyl C 'H ₁₉ C1F ₃ NO ₂ 130-140 C 50.34 53.07 2-chloroacetanilide (13.3) H 5.67 5.61 N 4.15 4.01 7 N- (methoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2- C ₁₂ H ₁₃ C1F ₃ NO ₂ oil C 48.47 49.94 chloroacetanilide H 4.43 4.44 N 4.74 4.70 8 N- (n-butoxymethyl) -2 '- (trifluoromethyl) -6'-methyl- C, _s H ₁₉ C1F ₃ NO ₂ 135-138 C 53.34 53.32 2-chloroacetanilide (6.7) H 5.67 5.68 N 4.15 4.14 9 N- (sec-butoxy) -2 '- (trifluoromethyl) -6' c ₁₅ h ₁₉ cif ₃ no ₂ 135-142 C 53.34 53.23 methyl-2-chloroacetanilide (6.7) H 5.67 5.67 N 4.15 4.13 10 N- (allyloxy) methyl-2'-trifluoromethyl) -6'-inetíI-2- c ₁₄ h ₁₅ cif ₃ no ₂ 123-125 C 52.27 52.11 chloroacetanilide (13.3) H 4.70 4.74 N 4.35 4.34 11 N- (propargyloxy) -2 '- (trifluoromethyl) -6' C _I4 H, jC1F ₃ NO ₂ oil C 52.59 52.44 methyl-2-chloroacetanilide H 4.10 4.14 N 4.38 4.34 12 N- (isoamyl oxy-methyl) -2 '- (trifluoromethyl) -6' c ₁₉ h ₂₁ cif ₃ no ₂ 150 C 54.63 64.66 methyl-2-chloroacetanilide (6.7) H 6.02 6.03 N 3.98 4.00 13 N- (ethoxymethyl) -2 '- (trifluoromethyl) -6'-ethyl-2-chloro- c ₁₄ h ₁₇ cif ₃ no ₂ 133-135 C 51.94 51.32 acetanilid (2.7) H 5.29 5.26 N 4.33 4.39 14 N- (n-propoxymethyl) -2'-trifluoromethyl (6'-ethyl-2- C _1s H ₁₉ C1F ₃ NO ₂ colorless C 53.34 53.74 chloroacetanilide oil H 5.67 5.77 N 4.15 4.16 15 N- (isopropoxymethyl) -2 '- (trifluoromethyl) -6'-ethyl c ₁₅ h ₁₉ cif ₃ no ₂ 100-105 C 53.34 53.74 2-chloroacetanilide (1.3) H 5.67 5.77 N 4.15 4.16

189,497

Preparation of compounds of general formula I according to Table (I) used in the preparation according to the above examples the secondary anilide starting materials the corresponding primary amine is carried out in a conventional chloro-acetylation as illustrated in Example 14 ^5.

Example 14

This example illustrates the preparation of the secondary anilide used as starting material for the preparation of the compound of Example 13.

6.0 g (0.03174 mol) of 2- (trifluoromethyl) -6-ethylaniline are dissolved in the solution was carefully added to 75 ml of toluene and chloroacetyl chloride (3.77 g; ¹⁵ 0.033 mol). The resulting slurry was heated to reflux and maintained at this temperature for 4 hours. The mixture was then diluted with an equal volume of hexane and allowed to stand. ²⁰ The product crystallized on standing, the crystalline solid was collected by filtration and air dried. 5.8 g (69%) of product are obtained. The filtrate was evaporated to give an additional 2.7 g of a white solid.

121-124 ° C (closed tube).

Analysis for C _n H _n ClF ₃ NO (t%)

Calculated: C 49.73; H, 4.17; N, 5.27;

Found: C, 49.36; H, 4.09; N, 5.38. ³⁰

The product was identified as 2 '- (trifluoromethyl) -6'-ethyl-2-chloroacetanilide by standard methods.

Primary amines of the type obtained by haloacetylation of secondary anilides as described above ³⁵ are known in the art, for example from the aforementioned U.S. Patent Nos. 3,966,811 and 2,013,188.

As noted above, the compounds of formula (I) may REN ⁴⁰ tially active ingredients and herbicidal compositions herbicidal properties. These herbicidal compositions are particularly useful as pre-emergence herbicides, but can also be used effectively as post-emergence herbicides. The pre-emergence effect was examined in both greenhouse and field experiments. In greenhouse studies, the herbicidal composition was applied to the soil surface after sowing the seeds or planting the vegetative propagation organs, or in the amount of soil needed to cover the seeds in the pots. In field experiments, the herbicidal composition may be introduced into the soil prior to planting the seeds (PPI pre-plant incorporation), for example by applying the herbicidal composition to the soil surface, then applying the mixing method and then sowing the seeds. The product is applied to the soil surface after planting the seeds (SA surface application). 60

The surface application (S.A.) test method in a greenhouse is carried out as follows:

Dishes, such as 24.13 cm x 13.34 cm x 6.99 cm aluminum dishes or 9.53 g x 93.53 cm x 7.62 cm plastic bowls, were filled to the brim with Ray's sedimentary marl. Drain openings are made at the bottom of the dishes. The soil is then compacted to a height of 1.27 cm from the top of the pots; the seeds of the plants used for the experiment are sown in the soil in the pots and covered with soil at a thickness of 1.27 cm. The herbicidal composition is applied as an acetone solution to the soil surface, for example by spraying at a rate of 187 L / ha (2.11 kg / cm ² ). Each pot is watered to a depth of 0.64 cm with water from above and then placed in a glasshouse and, if necessary, watered from below. Alternatively, top irrigation may be omitted. The degree of herbicidal activity is determined approximately three weeks after treatment.

The soil incorporation method (S.I. soil incorporation) is carried out in the greenhouse as follows:

The top layer of high quality soil is filled into aluminum pots and compacted to a depth of one and a half cm from the top of the pots. A predetermined number of seeds or vegetative propagating material of different plant species are placed on the soil surface. After sowing the seeds or planting the vegetative propagation material, the pots are filled to the brim with soil, which is prepared by thoroughly mixing a known amount of the active ingredient, either in acetone solution or as a wettable powder according to Formulation IVA, to cover the seeds. . After treatment, water with a volume of 0.64 cm rain is watered from above and then moistened from below to provide the water needed for germination and growth. Alternatively, the upper watering may be omitted. Evaluation is carried out 2-3 weeks after sowing and treatment.

The results of the tests for the determination of the pre-emergence herbicidal activity of the herbicidal compositions of the present invention are shown in Table II. and III. are summarized in Table. In these experiments, the herbicides were applied by soil mixing and the soil was only wetted from below. The herbicidal activity is expressed as a percentage of damage on a fixed scale. The scale is as follows:

% damage 0-24 25-49 50-74 75-100 indefinite scale 0 1 2 3 5

Values for experimental plants used in one series are shown in Table II. Table. The experimental plants used are identified by letters as follows:

G yellow slate H wheat I sorghum J hairy rye K cockfoot

The ace of the field B sea buckthorn C silk mallow D morning gluten E libatop F peppercorn

189,497

II. spreadsheet

Pre-emergence application

Example number of compound Heaven. kg / ha THE plant Variety THE B C D E F G H I J K I 11.2 5 3 3 3 3 3 3 3 3 3 3 5.6 5 2 2 3 3 3 3 3 3 3 3 2 11.2 2 1 1 3 2 2 3 3 3 3 3 5.6 3 2 1 3 2 3 0 2 2 3 3 3 11.2 3 1 2 3 3 3 3 3 2 3 3 5.6 2 0 2 3 3 2 3 3 1 3 3 4 11.2 5 3 2 3 3 3 3 3 3 3 3 5.6 5 2 1 2 3 3 3 3 3 3 3 5 - 11.2 5 3 2 3 3 3 3 3 3 3 3 5.6 5 0 0 3 3 3 3 3 1 3 3 6 11.2 5 2 1 3 3 3 3 3 3 3 3 5.6 5 2 0 1 3 3 3 3 3 3 3 7 11.2 3 1 2 2 3 0 2 3 1 3 3 5.6 1 0 I 1 3 0 1 3 1 3 3 8 11.2 3 2 0 2 3 3 3 3 3 3 3 5.6 3 1 0 3 3 3 3 3 . 2 3 3 9 11.2 3 2 2 3 3 3 3 3 3 3 3 5.6 3 2 1 2 3 3 3 3 1 3 3 10 11.2 3 2 1 3 3 3 3 3 3 3 3 5.6 3 1 1 2 3 3 3 3 0 3 3 11 11.2 3 1 1 3 3 3 3 3 0 3 3 5.6 3 1 1 2 3 3 1 3 1 3 3 12 11.2 3 2 0 2 3 3 3 3 0 3 3 5.6 3 1 0 2 1 2 3 3 3 3 3 13 11.2 3 2 2 3 3 3 3 3 3 3 3

The active ingredients were further tested by the above procedure, using the following plant species:

L soy-bean R silk hemp M sugar beet E pigweed N wheat F peppermint bitter grass SHE rice C velvetleaf B cocklebur S millet Q nuts bitter grass K barnyardgrass D morning glory T Muhammad

The results obtained are shown in Table III. are summarized in Table.

III. spreadsheet

Example number of compound

Heaven.

kg / ha

Pre-emergence application Varieties of plants

L Μ N Ö P B Q D R E F C Ϊ S K T

5.6

1.12

0.28

0,056

.0112

5.6

1.12

0.28

0,056

.0112

5.6

1.12

0.28

0,056

.0112

5.6

1.12

0.28

0,056

.0112

5.6

1.12

0.28

0,056

.0112

5.6

1.12

0.28

0,056

.0112

2

1

1

0

0

3

3

2

1

0

3

1

0

0

0

3

3

1

I

1

2

2

2

1

1

3

1

2

2

2

3 1 2 0 2 0 0 0 0 2 3

3 0 1 0 0 0 0

3

3 0 2 0 1 0 0 3 3

3 2 2 1 1 0 0

3

3 1 3 0 1 0 0

3 0 3 0 2 0 1 0 1

0 3 0 1 0 0 0 0 0 3 1 2 0 1 0 0 0 0 0 3 1 3 1 2 0 0 0 0 0 3 2 3 1 1 0 2 2 0 0 3 1 3 0 3 2 2 1 0 1 3 2 3 1 2 2 2 1 0 2

3 1 2 1 0 0 0 0 0 '3

3 0 1 0 0 0 0

3 0 3 0 0 0 0 0 0 3 3 3 2 1 0 1 0 0 0 3 3

0

3 2 0 1 0

3 3 3 2 · 1 2 2 2 2

3

3 '3 1' 1 Ó 1 3 3 1 2 1 1 0 0 0 0 3 3 1 3 0 3 0 2 C 1 3 3 3 3

3

1 0 1 3 3 2 3

3 1 3 0 3

3

3 3 3

3 2 3

2 2 0 3 0 1 0 1 0 3 0 2 0 0 0 0 0 0 0 3 1 0 0 0 0 3 0 0 0 3 1 3 1 3 0 1 0 0 0 3 1 3 0 3 0 1 0 1 0 3 1 3 0 3 0 1 0 1 0

3 3 3

3 0 2 0 1

3 3 3 3 3 1 1 0 0 3 3 3 3

3 0 3 0 3 3 3 3 3

3 0 2 0 3

3 3 3 3 3

3 1 2

3 3 3 3 3 2 3 1 1

3 3 3 3 3

3 2 2

5 3 5 3 5 3 5

5 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3

3

3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3, 189,497

Example number of compound Heaven. kg / ha Pre-emergence application plant Variety L M N She P B Q D R E F C 3 S K T 7 5.6 0 3 2 2 3 0 2 2 2 3 0 0 3 3 3 3 1.12 0 1 0 0 1 0 1 0 0 2 0 0 0 2 3 3 0.28 0 0 0 0 0 0 1 2 0 0 0 0 0 2 2 3 0,056 0 1 0 1 0 0 0 0 0 3 2 0 0 0 2 3 8 5.6 2 3 Λ 3 3 2 3 3 3 3 3 1 3 3 3 3 1.12 1 2 3 3 3 0 2 0 1 3 3 0 3 3 3 3 0.28 0 1 2 1 2 0 2 0 2 1 1 0 2 3 3 3 0,056 0 0 1 1 1 0 0 0 0 1 1 0 1 3 3 3 · .0112 1 0 0 0 0 1 0 0 I 0 0 0 1 0 2 3 9 5.6 2 2 3 3 3 2 3 3 3 2 3 1 3 3 3 3 1.12 1 2 3 3 1 1 3 1 2 2 2 0 3 3 3 3 0.28 1 2 2 3 2 0 1 1 2 1 1 0 3 3 3 3 0,056 0 0 0 0 0 0 0 0 0 2 1 0 2 3 3 3 .0112 0 0 0 0 0 0 0 0 0 0 0 0 0 0 3 3 10 5.6 3 3 3 3 3 2 3 3 3 3 3 0 3 3 3 3 1.12 1 2 3 3 3 0 3 3 2 2 3 0 3 3 3 3 0.28 0 2 2 2 2 0 1 0 2 3 2 0 3 3 3 3 0,056 0 1 0 1 0 0 0 0 1 0 0 0 0 3 3 3 .0112 0 0 0 0 0 0 0 0 0 0 0 0 0 1 2 3 11 5.6 0 3 3 3 3 1 3 3 3 3 3 2 3 3 3 5 1.12 0 3 1 3 1 1 1 2 1 2 2 0 3 3 3 5 0.28 0 2 1 2 1 0 0 0 1 1 1 0 3 3 3 5 0,056 0 1 0 0 0 0 0 0 5 0 0 0 1 2 3 5 .0112 0 1 0 0 0 0 0 0 0 0 0 0 0 1 3 5 12 5.6 1 2 2 3 3 1 2 2 0 2 1 0 3 3 3 3 1.12 1 2 1 2 3 0 2 2 1 2 2 0 3 3 3 3 0.28 0 1 0 J 0 0 1 0 0 1 0 0 1 2 3 2 0,056 0 5 0 0 0 0 5 0 0 0 0 0 0 0 2 0 13 5.6 2 3 3 3 3 2 3 3 3 3 3 2 3 3 3 3 1.12 1 2 3 3 3 0 2 2 3 2 3 0 3 3  3 3 0.28 2 2 3 3 1 0 1 0 3 1 3 0 3 3 3 3 0,056 0 1 1 1 0 0 1 0 0 0 0 0 2 3 3 3 .0112 0 0 0 0 0 0 0 0 1 5 5 0 0 0 2 2

We have found that the herbicidal compositions of the invention show unexpectedly superior herbicidal properties as pre-emergence herbicidek- ^35, particularly difficult to control the selective control of annual and perennial weeds. Such perennial weeds are milled wheat, yellow and purple slate, and annual broadleaf weeds, spiny mildew, silk hemp, pear ⁴⁰ , goose and porcine, herbaceous reeds, thistle, wild millet, red rice, itchy bitter grass (Raoulgrass; Rottboellia exaltata), brush lawns such as green, yellow and giant brush lawns, ⁴ ® cocksfoot and toad muh. It has also been possible to reduce the resistance of other resistant varieties, such as ragweed, mulberry, dandelion, buckthorn, porcini and similar weeds, with the herbicidal compositions of the present invention. ⁵⁰

It has also been found that the aforementioned weeds can be selectively controlled and their development greatly suppressed among various crop plants, particularly in soybean, corn and other crops such as cotton, peanut, rape, bean, wheat and sorghum according to the invention. herbicidal preparations.

However, the latter two crop plants are less tolerant to the herbicidal compositions of the invention than the other crop plants mentioned. However, such reduced resistance can be enhanced by the administration of antibodies, such as herbicidal antidotes.

Throughout the specification and tables, herbicide applicability values "GRi _S " and "GR _8J " will be referred to hereinafter. These values are expressed in kilograms / hectare (kg / ha). GR _ls denotes the maximum amount of herbicidal active ingredient which is 15% or less harmful to the crop, while GR ₈₅ denotes the smallest amount of herbicidal active ingredient necessary to control weeds at 85%. The terms GR ₁₅ and GR _{85 are} used in the art as a measure of effective performance. Commercially available herbicides may have greater or lesser harmful effects on plants within reasonable limits.

The so-called "selectivity factor" for crops and weeds applied to a herbicide is used to indicate the selective herbicidal activity of the active substances. The selectivity factor is denoted by "SF" (selectivity factor), which is expressed as the ratio of the degree of safety of the crop to the damage of the weed, the ratio GR _ls / GR _gs , ie the GR ₅ for the crop is divided by the GR ₈₅ values, each in kg / ha. In the following tables, selectivity factors are given in brackets after GR ₈₅ . The symbol "NS" indicates a non-selective property. The dash (-) indicates indeterminate selectivity.

Since crop tolerance and weed control are related, a brief discussion of this relationship with respect to the selectivity factor is advantageous. Generally, it is desirable that crop safety factors, such as tolerance values, be high,

189,497 since it is often necessary to increase the concentration of the herbicide for some reason. However, it is expedient to have a low weed dose, for example a herbicide having high unit activity due to economic and ecological considerations. The use of a small amount of herbicide is not sufficient to control certain weeds and a larger amount is required. Therefore, the best herbicidal agents are those which control as many weeds as possible using the smallest amount of herbicides and at the same time guarantee the safety of the crop, i.e., its tolerance. Therefore, the selectivity factors given above are determined to quantify the relationship between crop safety and weed control. For the selectivity factors shown in the tables, the higher the numerical value, the greater the selectivity of the herbicidal composition for a given herbicide in a given crop.

In order to demonstrate the unexpected excellent properties of the herbicidal compositions of the present invention, both in absolute and relative terms, comparative studies were conducted in the greenhouse using the herbicidal active ingredients closest to those of the herbicidal compositions of the invention. Known herbicidal agents are designated by the following letters; in addition, the nomenclature used for naming the active ingredients of the compositions of the invention is followed.

N- (methoxyethyl) -2 '- (trifluoromethyl) -2-chloroacetanilide, and

B N- (ethoxyethyl) -2 '- (trifluoromethyl) -2-chloroacetanilide.

The IV. Tables V and V show pre-emergence herbicidal activity comparing the relative potency of the active compounds of the herbicidal compositions of the present invention with known active substances which act as selective herbicides on soybean and maize-resistant perennial wheatgrass and yellow slate weeds. against. These weeds mainly live with maize and soybean crop plants. The IV. The experimental data summarized in Tables I and V below were obtained under the same conditions and as an average of two experiments, except for the active ingredient of Example 13, which was the result of one experiment. The test procedure was the same as in Annex II. and III. with the exception that initially water was applied at a height of 0.64 cm, but then only the soil was wetted from below. "NS" means that the herbicide is not selective under experimental conditions and test limits.

JV. spreadsheet

The exam! agent Gru value (Kg / ha) soy-bean GR _e value of j (kg / ha) quitch yellow salary THE > 2.24 > 2.39 (NS) 1.13 (1.98) B 1.96 0.61 (3.21) 0.44 (4.45) Example 1 2.67 0.17 (15.6) 0.17 (15.6) Example 3 1.68 0.27 (6.22) 0.19 (8.84) Example 4 1.12 0.13 (8.62) 0.17 (6.59) Example 5 1.46 0.26 (5.62) 0.26 (5.62) Example 13 2.13 0.20 (10.65) 0.17 (12.53)

The IV. Table 1 shows that the herbicidal compositions of the present invention exhibit superior selectivity factors (values in parentheses) over the active ingredients of the prior art formulations against soybean wheat and yellow slate. In addition, it is noted that the unit activity (relative phytotoxicity / unit herbicidal active ingredient) of the active ingredients of the herbicidal compositions of the invention is significantly better than that of the active ingredients used for this purpose, while being safe against crop plants. The selectivity factors of the active compounds of Examples 1 and 13 are particularly good.

The relative efficacy of the herbicidal compositions of the present invention against the active compounds described in the literature and described above is shown in Table V. Data were obtained from comparative studies on maize wheat and yellow slate.

Table V.

Test substance GR _ls value (kg / ha) GRgs value (kg / ha) quitch yellow salary THE > 2.24 > 2.39 (NS) 1.13 (1.98) B 0.81 0.61 (1.33) 0.44 (1.84) Example 1 0.76 0.17 (4.47) 0.17 (4.47) Example 3 1.94 0.27 (7.19) 0.19 (10.2) Example 4 0.75 0.13 (5.85) 0.17 (4.47) Example 5 1.83 0.26 (7.04) 0.26 (7.04) Example 13 2.24 0.20 (11.2) 0.17 (13.18)

From the data in Table V, it can be seen that the active ingredients of the herbicidal compositions according to the invention have much better selectivity factors than the active ingredients of the prior art formulations against live corn and yellow slate. In addition, it is noteworthy that the unit activity of the active ingredients of the herbicidal compositions according to the invention is significantly better against the common wheat and yellow slate than the above-mentioned herbicidal active ingredients, while being safe against crop plants. The selectivity factors of the active compounds of Examples 3, 5 and 13 compared with known herbicidal agents are particularly beneficial.

AIV. It is clear from the comparative data in Tables I and V of the present invention that the active ingredients of the herbicidal compositions of the present invention exhibit remarkably better and unexpected good herbicidal activity against two major crop plants, soybean and maize-91.

189,497 rica live wheat and yellow slate against perennial weeds as active ingredients A and B, which are closest to those of the herbicidal compositions of the invention.

Pre-emergence herbicidal data from other studies also demonstrate that the herbicidal compositions of the present invention selectively kill common wheat, yellow logs and / or other weeds on one or more crop plants such as cotton, bush bean, peanut, wheat, sorghum and / or rape. between. The following is a description of VI. Table selective herbicidal effects of formulations containing the active compounds according to the Examples 1 and 3 in rape, snap beans, sorghum and wheat against quackgrass sheet ⁵ weave. VI. The results of the data shown in Table 1 are from experiments performed in a greenhouse, the herbicidal compositions were applied to the soil by soil mixing, initial surface irrigation followed by bottom ⁰ irrigation as described above.

VI. spreadsheet

Test substance Gru value (Kg / ha) GR value ₈ (kg / ha) rape snap beans sorghum wheat quitch Example 1 0.85 - 0.12 (7.2) - 0.90 - - 0.12 (7.5) Example 1 - - 0.24 - 0.12 (2.0) - - - 0.21 0.12 (1.8) Example 3 1.9 - - - 0.28 (6.8) - 2.24 - - 0.28 (8.0) - - 0.84 - 0.28 (3.0 - - - 0.28 0.28 (1.0)

The active ingredient of Example 1 was also tested in the open field to determine its pre-emergence selective herbicidal activity against brush crops, cocksfoot and white millet among various crops. The results (which are the average of three replicates) are shown in Table VII. Table II is used for both surface application (S.A.) and pre-emergence soil mixing (PPI = preplant incorporation). The seeds were seeded in a medium moisture, fine mesh sedimented marl at a depth of 5.08 cm. The first irrigation was done 0.51 cm deep on the day after the treatment and the second irrigation was 0.64 cm deep two days after the treatment. The amount of irrigation water after treatment is total on day 22

It was 4.57 cm. Evaluation was performed 6 weeks after treatment.

VII. % inhibition

Example number of compound Application Heaven. feed mány- research work korica dessert corn ca soy- puppet ground- hazelnut imposes cotton sorghum bush- puppet rape brush- lawn rooster. foot grass white millet mode (Kg / ha) 1 S.A. 0.56 0 0 0 0 0 0 0 0 62 63 63 1.12 0 0 5 0 13 3 8 0 92 93 83 2.24 0 7 0 8 20 17 20 5 93 93 95 4.48 15 27 13 22 25 77 32 33 98 98 97 P.P.I. 0.56 0 0 5 17 13 32 23 0 75 75 23 1.12 0 3 7 13 32 53 10 0 90 93 58 2.24 5 27 20 15 37 92 37 15 98 98 80 4.48 32 40 40 28 ' 82 98 43 40 100 100 85

VII. The data in Table I show that the herbicidal compositions of the invention containing the active ingredient of Example 1 generally exhibit better selective activity when applied to the soil than when applied to soil. For herbicidal applications, the herbicide was selective for three weeds at 0.58 kg / ha, while the crop was not damaged by ⁶⁰ , and up to 15% for maize and up to 4.48 kg / ha for soybean. Crop damage, such as sweet corn, peanuts, and rape, has been found to be less than 65 mg / ha even in cotton, sorghum and bush beans.

There was no damage at 2.24 kg / ha. At pre-emergence soil mixing, the active ingredient of Example 1 selectively inhibited the development of muhar and moths at less than 1.12 kg / ha, but did not damage maize, peanuts and rape at 2.24 kg / ha. , or slightly

Less than 2.24 kg / ha in soybean.

The results of field trials with the herbicidal formulation containing the active ingredient of Example 1 show that the formulation is a grafting agent.

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189 497 has selective control against other weeds in soybean, maize, cotton and / or peanut crop. Such weeds are purple slate, giant muhara, yellow muhara, goatop, dawn, meadow grass, mulberry, peppermint, spiny marshmallow, porchin, red-toothed muffin, goose pimple, texas millet, floridae orb. It will be appreciated by those skilled in the art that this herbicidal composition does not selectively eliminate all of the aforementioned weeds that live among the aforementioned crop plants, in all climatic zones and conditions, but depends on the particular soil, moisture and / or application method. Experimental results for the selective control of weeds between different crops, such as soybeans, maize, cotton and peanuts, are shown in Sections VIII to XI. are summarized in tables. These results are obtained under various outdoor conditions, in different locations, on different soils and vm.

we got it under humidity. In the tables, the term "WA i (week after treatment)" refers to the number of weeks after treatment for both surface application (SA) and soil application (PPI). The amounts used are given in GR _1S and GR ₈₅ , and the GR _1S / GR ₈₅ ratio, as known above, results in a selectivity factor. The designation "NS" means that the active ingredient is non-selective while the dash (-) indicates low or undetermined selectivity since the actual GR ₁₅ and GR _8J values were greater or less than the highest or lowest value used in the assay. VIII-XI. the blank space in the tables indicates that the plant variety in question has not been tested, yielded or is insignificant. For example, some WAT evaluations, such as certain 3-week evaluations, were omitted for the 6-week evaluation, or 3-week evaluations were preferred because they were more decisive and the 6-week evaluations were omitted.

Example number of compound Crop / weed combination application mode WAT gr _{15 to} gr ₈₅ ratio S. F. 1 soybean / giant muhar S.A. 3 S.A. 5 > 4.48 / <1.12 (> 4.0) P.P.I. 3 5 > 4.48 / <1.12 (> 4.0) 8 > 4.48 / <1.12 (> 4.0) soybeans / yellow muhar S.A. 6 2.52 / 2.9 (NS) ppm 6 1.4 / <1.12 (> 1.3) Soybean / Iibatop spp S.A. 6 2.52 / 2.52 (1.0) P.P.I. 6 1.4 / 2.8 (NS) Soybean / knotweed ppm 8 4.48 / 2.52 (1.8)

VIII. The results in Table I show that the herbicidal composition containing the active ingredient of Example 1 selectively kills giant and yellow moor, goatop and borage beans in soybean 6-8 weeks after treatment in both S.A. and P.P.I. treatment mode.

IX. spreadsheet

Example number of compound Crop / weed combination application Sewage mode WAT gr _{15 to} gr ₈₅ ratio S. F. 1 corn / giant muhar S.A. 6 4.48 / <1.12 (4.0) S.A. 6.5 > 7.84 / 8.4 (NS) ppm 6 4.76 / 1.96 (2.5) ppm 6.5 > 6.72 / 4.48 (1.5) maize / morningglory S.A. 3 > 4,48 /> 4,48 (-) S.A. 6 > 4,48 /> 4,48 (-) ppm 3 4.76 /> 4.48 (-) ppm 6 4.76 /> 4.48 (-) maize / tarlófű S.A. 3 > 4,48 /> 4,48 (-) S.A. 6 > 4,48 /> 4,48 (-) P.P.I. 3 4.76 /> 4.48 (-) P.P.I. 6 4.76 /> 4.48 (-)

IX. The results in Table show that the herbicidal composition containing the compound of the Example 1 of controlling the óriásmuhart maize 5-6.5 weeks after treatment, all ⁶⁰

S.A., both P.P.I. application mode. The selectivity for seaweed and stalactite could not be determined at the test values used, but damage to these weeds was also observed.

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Table X.

Example number of compound Crop / weed combination application mode WAT GR _1S / GR ratio S. F. 1 cotton / purple wages S.A. 6 3.64 / 1.68 (2.17) S.A. 9 3.36 / 2.24 (1.5) P.P.I. 6 3.36 / 4.2 (NS) cotton / spiny mildew S.A. 6 3.64 / 3.08 (1.18) S.A. 9 3.36 / 4.76 (NS) P.P.I. 6 3.36 / 4.76 (NS) cotton / purslane S.A. 9 3.36 / 1.96 (1.7) cotton / red-toed muhar S.A. 7 1.4 / ≤ 1.12 (> 1.25) (smooth and hairy) P.P.I. 7 0.84 / 1.12 (NS) cotton / silverweed cinquefoil P.P.I. 7 0.84 / <l, 12 (-)

The results summarized in Table X show that the herbicidal composition containing the active ingredient of Example 1 selectively kills purple log and powdery mildew 9 weeks after treatment, spiny marshmallow after 6 weeks, and red-toed muffin after 7 weeks. damage to the goose pimple ₂ remains weak and undetermined.

The XI. Table 1 below shows the pregelatinisation effect of the herbicidal composition containing the compound of Example 1 as an active ingredient in three resistant

XI. teas in the case of annual weeds, namely Texas millet, spiny thistle and Florida weed on peanut plantation for 12 weeks after treatment.

The XI. Experimental data in Table 1 represents the average of three replicates. The experiments were carried out on sandy-marl soil containing 1.3% organic matter, 79.2% sand and 10% clay. The herbicidal agent was applied to the surface.

Percent inhibition

Example number of compound Heaven. kg / ha peanuts texas millet spiny thistle florida fuel gas 4 WAT 8 12 4 WAT 8 12 4 WAT 8 12 4 WAT 8 12 1 2.24 5 0 0 50 60 40 78 40 0 95 3.36 10 0 0 68 63 55 85 60 0 4.48 17 7 0 85 88 78 95 100 0 85 95

The XI. The test results in Table I show that herbicidal compositions containing the active ingredient of Example 1 selectively kill the peanut Texas millet for 8 weeks and exhibit a high degree of pesticidal activity 12 weeks after application at a rate of about 4.48 kg / ha. Selective eradication of spiny thistle is achieved at 3.36 kg / ha for 8 weeks and the overall eradication effect is maintained for 12 weeks at 4.48 kg / ha. Selective eradication of the Florida typewriter is achieved using less than 2.24 kg / ha of active ingredient for 8 weeks, while 4.48 kg / ha of active ingredient produces 95% selective eradication 12 weeks after treatment.

In other greenhouse studies, the herbicidal compositions of the invention have shown selective control against annual and perennial weeds living on different crop plants. For further proof, the herbicidal formulations containing the active ingredient of Example 1 selectively eradicated purple log in both corn and soybean at a crop to weed ratio of GR ₁₅ / GR ₈₅ (in kg / ha) of 0.67 / 0.25. was (SF = 2.7) in corn and 1.12 / 0.25 (SF = 4.5) in soybean. All. The herbicidal formulations containing the active ingredient of Example 1 to 5 were selectively eliminated for yellow log and corn wheat in maize and soybean. The right crop / yellow slate weed GR ₁₅ /

The GRg _S ratio was greater than 2.24 / 0.95 (SF = 2.4) for maize, and soybean ratio was 2.24 / 0.5 (SF = 4.5). In the case of wheat wheat, the corresponding GRu / GR ₈₅ ratios were found to be> 2.24 / 0.5 (SF = 4.5). The control effect on cotton yellow yellow slate was favorable as the mean of two replicates, with a GR / 5 / GR ₈₅ ratio of 1.96 / 0.95 (SF = 2.1). Herbicidal formulations containing the active ingredient of Example 13 showed selective extermination against yellow slate cultivated between cotton and wheat live on wheat. The corresponding GR ₁₅ GR ₈₅ values were 0.7 / 0.47 (SF = 1.7) for cotton and 0.58 / 0.47 (SF = 1.2) for wheat.

In a multi-crop study in a greenhouse, the herbicidal formulations containing the active compounds of Examples 13, 14 and 15 were used against yellow slate in cotton, soybean, corn and rice. In the case of rice, none of the active ingredients were selective against yellow logs, but showed very good selective control against yellow logs in rice. The corresponding GR _I5 and GR ₈₅ values are shown in Table XII. Table. The selectivity factor is indicated in parentheses after each crop.

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XH. spreadsheet

Example number of compound gr, ₅ (kg / ha) yellow wages cotton gr ₁₅ (kg / ha) soy- puppet maize rica 1 0.24 1.96 (9.2) 0.87 (3.6) 0.69 (2.9) 13 0.21 2.52 (12.0) 1.96 (9.3) 2.52 (12.0) 14 0.39 2.8 (7.4) 2.24 (5.9) 1.68 (4.4) 15 0.44 2.8 (6.4) 1.96 (4.5) 1.96 (4.5)

1 and 13-15. The herbicidal compositions containing the active compounds of Examples 1 to 5 were further investigated against wheat in wheat, soybean and corn crop plants. None of the active ingredients were found to be selective in wheat. The results on selectivity against corn wheat in soybean and maize are shown in Table XIII. are summarized in Table.

XIII. spreadsheet

Example number of compound GRG; (Kg / ha) quitch gr ₁₅ (kg / ha) soy-bean maize 1 0.07 0.81 (11.6) 0.69 (9.9) 13 0.36 1.68 (4.7) 1.68 (4.7) 14 0.45 1.46 (3.2) 2.52 (5.6) 15 0.75 1.96 (2.6) 2.24 (3.0)

In further greenhouse studies, the herbicidal formulations containing the active compounds of Examples 1 and 3 were tested against a number of herbaceous grasses, including resistant weeds such as Texas millet, sorghum sprout, shredded reed, spiny dogwood, panicum milica. against itching. The results of the tests are shown in Table XIV. are summarized in Table. Selectivity factors are given in brackets. The dash indicates low or indefinite selectivity.

XIV. spreadsheet

Example number of compound GR, _s value (kg / ha) soybean GR _e5 value (kg / ha) Texas millet fenyér- sorghum splintery reed szálka- peije prosecution- millet reptile- millet red- rice viszke- tofu 1 > 1.12 1.12 0.14 0.28 0.56 1.12 <0.07 0.2 1.12 (> L, 0) (> 8.0) (> 4.0) (> 2.0) (> L, 0) (> 16.0) (> 5.6) (> 1.0) 3 > 1.12 > 1.12 0.28 0.93 > 1.12 1.12 <0.07 0.14 > 1.12 (-) (> 4.0) (> 1.2) (> L, 0) (-) (> 16.0) (> 8.0) (-)

XIV. The data in Table II show that the herbicidal composition containing the active ingredient of Example 1 selectively eliminated all the annual weeds tested in soybean. The herbicidal composition containing the compound of Example 3 have potent selective disinfestation ³⁵ against all weeds, except Texas millet, fall panicum and itchgrass, the maximum 1.12 kg / ha amount. In order to investigate the selective action against these three weeds, a higher amount of active ingredient would be required as no selective extermination was observed at the applied amount.

A distinctive advantage of a herbicidal composition is that it can exert its effects on a wide variety of soil types. Accordingly, the XV. Table III shows data demonstrating the efficacy of the herbicidal composition containing the active ingredient of Example 1 against soybean wheat in different soils, such as organic soil and clay soil. The herbicide treatment was carried out using a soil mixing method, the seeds were sown to a depth of 0.95 cm and then the soil was watered to a depth of 0.64 cm. Evaluation was performed three weeks after treatment. In the table, selectivity factors are shown in bracketsXV. spreadsheet

Example number of compound Soil type Organic matter% Clay t% Gru value (Kg / ha) soy-bean _Grain wheat GR _8S value (kg / ha) 1 Ray's sedimentary marl 1.0 9.6 1.12 0.22 (5.1) Sarpy sedimentary clay 2.3 30.35 > 2.24 0.28 (> 8.0) Wabash sedimentary clay 4.3 33.0 - 0.28 (-) Drummer sedimentary clay 6.0 37.0 2.24 0.11 (20.0) florida sand 6.8 1.8 1.96 0.2 (9.8) Florida compost 60 - > 2.24 0.58 (> 3.9)

In the XV. Table 1 shows that herbicidal formulations containing the active ingredient of Example 1 are not at all sensitive to the type of organic matter in the soil varieties and selectively eradicate wheat soybean in soil types containing 1.0-601% organic matter and 1, They contain 8-37% by weight of clay.

In the case of soybeans in Wabash sedimentary clay soils, the data obtained in this experiment were inconclusive. In addition, the selectivity factors for Sarpy and Drummer sedimentary clay soils and for compost in Florida are minimum values, since the highest amount tested

Was 2.24 kg / ha and the herbicidal composition proved to be safe for soybean at the same amount of 2.24 kg / ha.

Laboratory tests were performed to determine the inventive properties

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189 497 rinse herbicidal compositions against soil leaching and determine the resulting herbicidal activity. In these assays, Figs

4-6. The formulations of Examples 1 to 8 were formulated in acetone and then sprayed at various concentrations on Ray sedimentary marl and Drummer sedimentary marl in vessels equipped with filter paper-covered irrigation openings. The pots containing the treated soil were washed by placing the pots on a rotating table and rotating the table under a water tank whose two nozzles sprayed 2.5 cm of water per hour to simulate rainfall. The amount of rain was controlled by adjusting the rotation time of the turntable. Water was applied to the surface of the soil in the pots and allowed to seep through the filter paper and the

XVI.

watering holes. The dishes were then allowed to stand for three days at room temperature. The treated soil in the pots was removed from the pots, rubbed and placed on top of pots filled with said soils and planted with cocksfoot seeds. The pots were then taken to a greenhouse, watered from below, and kept there for 2-3 weeks to allow the plants to develop. Percent inhibition of growth was observed at ⁰ % relative to control (untreated) vessels. Control data are from the mean of six replicate assays, while the test results for the active ingredients are from the mean of 3 replicates for each of the ⁵ replicates. The results of the tests are shown in Table XVI. are summarized in Table. The fresh weights of the weed were not measured in experiments in Drummer's sedimentary marl.

spreadsheet

Example number of compound Heaven. (Kg / ha) Rain (Cm) Percent inhibition Fresh weight (g) Ray soil Drummer soil Ray soil Drummer soil control 0 0 4.37 0 1.27 3.88 0 5.08 4.14 0 10.16 3.98 average 4.10 1 2.24 0 100 100 0 1.27 100 100 0 5.08 95 100 0.20 - 10.16 35 100 2.65 - 0.56 0 100 100 0 1.27 100 100 0 - 5.08 70 100 1.21 10.16 33 100 2.73 1 0.14 0 95 100 0.20 1.27 96 97 0.17 - 5.08 58 95 1.74 10.16 20 20 3.26 4 2.24 0 100 100 0 1.27 100 100 0 5.08 100 100 0 10.16 95 100 0.22 0.56 0 100 100 0 - 1.27 100 100 0 - 5.08 94 100 0.24 10.16 52 100 1.97 - 4 0.14 0 99 81 0.05 - 1.27 95 99 0.22 - 5.08 63 94 1.53 10.16 14 54 3.15 - 5 2.24 0 100 100 0 1.27 100 100 0 5.08 '92 100 0.31 - 10.16 71 100 1.18 - 0.56 0 99 100 0.02 - 1.27 100 100 0 - 5.08 89 100 0.44 - 10.16 17 96 3.41 - 5 0.14 0 98 70 0 1.27 90 96 0.41 - 5.08 38 85 2.77 - 10.16. 12 47 3.62 - 6 2.24 0 100 100 0 - 1.27 100 100 0 5.08 99 100 0.03 - 10.16 84 100 0.64 -

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Example number of compound Heaven. (Kg / ha) Rain (Cm) Percent inhibition Fresh weight (g) Ray soil Nier-drum soil Ray soil Drummer soil 0.56 0 99 50 0.04 1.27 99 100 0.02 5.08 90 93 0.41 10.16 72 84 1.17 6 0.14 0 84 12 0.66 1.27 90 26 0.43 5.08 58 20 1.72 10.16 29 12 2.92

XVI. The data in Table II show that the herbicidal compositions ₃ according to the invention containing the compounds of the formula I as active ingredients are well resistant to leaching into soil under various rain conditions. For example, at 2.24 kg / ha of active ingredient, each of the specified active compounds exterminated cocksfoot in 10.16 cm rainfalls in Ray sedimentary marl and _{2 in} Drummer sedimentary marl.

With the exception of the active compounds of Example 5, where the eradication effect was maintained at a rainfall of 5.08 cm. Herbicidal formulations containing the active compounds of Examples 1, 4 and 5, even at very low application rates of ₂ to 0.14 kg / ha, eradicated cocksfoot in Drummer sedimentary clay with a rainfall of 5.08 cm.

The compound of Example 1 showed toxicity study of that the active substance ₃ is completely safe. Although the drug has a slightly toxic effect (OLD ₅₀ = 2300 mg / kg; MLD _S0 > 5010 mg / kg) and slightly irritates the eyes, it does not irritate the skin. ₃ does not have any special handling procedures required in addition to the normal precaution.

See the detailed description described above to advance the herbicidal compositions of the invention are unexpected and have very good herbicidal properties, both in absolute terms, in particular, agents of the herbicides compared ^four most closely related to drugs. Herbicide containing the compound of formula (I) as an active ingredient proved composition to provide excellent selective herbicidal agents, especially difficult to control annual and perennial ⁴ weeds soybean and corn crops, but peanuts, cotton and other crops as well. Especially good herbicidal activity against the herbicidal compositions according to the invention perennial weeds, such for instance the ^TA-5 rack wheat and Cyperus species and resistant annual grasses such as Texas millet, itchgrass, fall panicum, szálkaperje, johnsongrass, splintered cane, and / or and also inhibit or reduce the development and growth of other less resistant perennials and perennial weeds.

The compositions of the invention ideszámítva concentrates which require dilution prior to use - ^{contain the active ingredient and a liquid or solid excipients. The formulations are prepared by admixing the active ingredient with an excipient such as diluent, excipient, carrier, and conditioning agent, and finely divided (solids, granules, pellets, solutions, dispersions or emulsions), for example, using the excipient, e.g. a finely divided solid, an organic liquid, water, a wetting agent, a dispersing agent, an emulsifying agent, or any suitable combination thereof.

The compositions of the present invention, particularly liquids and wettable powders, preferably contain one or more surfactants in an amount sufficient to render the composition readily dispersible in water or oil. The incorporation of surfactants into the compositions greatly enhances their effectiveness. By "surfactant" is meant wetting agents, dispersing agents, suspending agents, and emulsifying agents. Anionic, cationic and nonionic materials can be used.

Preferred wetting agents include alkyl benzene and alkyl naphthalene sulfonates, sulfonated fatty alcohols, amines or acid amides, long chain acid esters of sodium isothionate, sodium sulfosuccinate esters, sulfated or sulfonated esters, , sulfonated vegetable oils, ditertiary acetylene glycols, polyoxyethylene derivatives of alkyl phenols (especially isooctylphenol and nonylphenol), and polyoxyethylene derivatives of hexitol anhydride mono-chain fatty acids (e.g. sorbitan). Preferred dispersants are methyl cellulose, poly (vinyl alcohol), sodium lignin sulfonates, polymer alkyl naphthalene sulfonates, naphthalene sulfonate sodium salt and polymethylene bisnaphthalenesulfonate.

Wettable powders are water-dispersible formulations containing one or more active ingredients, an inert solid filler and one or more wetting and dispersing agents. Inert solid fillers are usually of mineral origin, such as natural chalk, diatomaceous earth, silica-derived synthetic minerals and the like. Examples of such fillers are kaolinites, attapulgite chalk and synthetic magnesium silicate. The wettable powder compositions of the present invention are usually about 0.5 to 60 parts by weight, preferably 5 to 20 parts by weight, of active ingredient, about 0.25 to 25 parts by weight, preferably

From 1 to 15 parts by weight of a wetting agent, from about 0.25 to 25 parts by weight, preferably from 1.0 to 25 parts by weight, of a dispersing agent and from about 5 to 95 parts by weight, preferably

5-50 parts by weight of an inert solid filler

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They contain 189,497. If desired, about 0.1 to about 2.0 parts by weight of a solid, inert filler may be replaced by an anti-corrosion agent, an antifoam agent, or both.

Other formulations are powder concentrates containing 0.1-601% of active ingredient with suitable excipients. These powders may be diluted to a desired concentration in the range of about 0.1 to about 10% by weight prior to use.

Aqueous suspensions or emulsions may be formulated by mixing the aqueous mixture of a water-insoluble active ingredient and an emulsifier until homogeneous and subsequently homogenizing to obtain a very fine particle size stable emulsion. The resulting concentrated aqueous slurry is characterized by an extremely fine particle size so that after dilution and spraying it gives a very uniform coating. Suitable concentrations of these formulations are in the range of about 0.1 to about 60% by weight of the active ingredient, but the upper limit is determined by the solubility of the active ingredient in the solvent.

Other aqueous suspensions are prepared by encapsulating a water-immiscible herbicidal active ingredient to form a microencapsulated phase dispersed in the aqueous phase. In another embodiment, mini-capsules are formed by mixing the aqueous phase containing the lignin sulfonate emulsifier and the water-insoluble active ingredient and the polymethylene polyphenyl isocyanate, dispersing the water-immiscible phase in the aqueous phase and then adding mix. The isocyanate and the amine react with each other to form a solid urea shell around the water-immiscible active ingredient to form microcapsules. The concentration of the microencapsulated material is generally in the range of about 480-700 g / l, preferably 480-600 g / l.

Concentrates are generally solutions of the active ingredient in water-immiscible or partially miscible solvents and a surfactant. Suitable solvents for dissolving the active ingredients of the herbicidal concentrates of the invention include dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, hydrocarbons and water-immiscible ethers, esters or ketones. In addition, other high concentration liquid concentrates may be prepared by dissolving the active ingredient in a solvent and then diluting the solution to the desired concentration, e.g., kerosene, to achieve a sprayable concentration.

The concentrated compositions contain from 0.1 to 95 parts by weight, preferably from 5 to 60 parts by weight, of the active ingredient, from 0.25 to 50 parts by weight, preferably from 1 to 25 parts by weight, of a surfactant and optionally from 4 to 94 parts by weight of solvent.

Granules are physically stable formulations containing the active ingredient bound to a finely divided filler. In order to facilitate delivery of the active ingredient from the particles, a surfactant as mentioned above is included in the composition. Mineral fillers include natural chalk, pyrophyllite, illite and vermiculite. Aqueous front fillers include porous, absorbent preformed particles such as preformed and screened particulate attapulgite or heat-expanded particulate vermiculite and finely divided chalk such as kaolin, hydrated attapulgite or bentonite. These fillers are sprayed or mixed with the active ingredient to form a herbicidal granulate.

The granular compositions of the present invention contain from 0.1 to 30 parts by weight, preferably from 3 to 20 parts by weight, of active ingredient per 100 parts by weight of chalk and up to 5 parts by weight of surfactant per 100 parts by weight of particulate chalk.

Other additives such as fertilizers, other herbicides, pesticides, crop protection agents and the like, as well as other additives listed above, may also be incorporated into the compositions of the present invention. Compounds which may be used in combination with the active compounds of the formula I include triazines, urea derivatives, carbamates, acetamide, acetanilide, uracil, acetic acid or phenol derivatives, thiolcarbamates, triazoles, benzoic acid derivatives, nitriles, biphenyl ether derivatives and the like, e.g. nitrogen / sulfur derivatives:

2-chloro-4-ethyl-amino / -6- (isopropylamino) -s-triazine,

2-chloro-4,6-bis (isopropylamino) -s-triazine,

2-chloro-4,6-bis (ethylamino) s-triazine,

3-isopropyl-1H-2,1,3-benzothiadiazin-4- (3H) -one-2,2-dioxide,

3-amino-1,2,4-triazole,

6,7-dihydro-dipyrido- (1,2-a: 2 ', l'-c) -pyrazidinium salt,

5-bromo-3-isopropyl-6-methyluracil 1,1'-dimethyl-4,4'-bipyridinium.

sulfonylureas:

N '- (4-chlorophenoxy) phenyl-N, N-dimethylurea, N, N-dimethyl-N' - (3-chloro-4-methylphenyl) urea, 3- (3,4-dichloride) h -phenyl) -1,1-dimethylurea, 1,3-dimethyl-3- (2-benzothiazolyl) urea, 3- (p-chlorophenyl) -1,1-dimethylurea .

butyl-3- (3,4-dichlorophenyl) -1-methylurea.

Carbamate thiocarbamates:

2-chloroallyl diethyldithiocarbamate, S- (4-chlorobenzyl) -N, N-diethylthiolcarbamate, isopropyl-N- (3-chlorophenyl) carbamate, S-2,3-dichloro- allyl N, N-diisopropylthiolcarbamate, ethyl Ν, Ν-dipropylthiolcarbamate, S-propyldipropylthiolcarbamate.

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189,497

Cetamidoclacetanyldecanylecllamides:

2-chloro-N, N-diallyl acetamide,

N, N-dimethyl-2,2-diphenylacetamide,

N- (2,4-dimethyl-5 - {[(trifluoromethyl) sulfonyl] amino} phenyl) acetamide,

N-isopropyl-2-chloroacetanilide,

2 ', 6'-diethyl-N- (methoxymethyl) -2-chloroacetanilide,

2'-methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide, a, a, a-trifluoro-2,6-dinitro-N, N-dipropyl- p-toluidine,

N- (1,1-dimethyl-propinyl) -3,5-dichlorobenzamide. Acids / Esters / Alcohols:

2,2-dichloro-propionic acid,

2-methyl-4-chlorophenoxyacetic acid,

2,4-dichlorophenoxyacetic acid, methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propionate,

3-amino-2,5-dichlorobenzoic acid,

2-methoxy-3,6-dichlorobenzoic acid,

2.3.6-trichlorophenylacetic acid,

N-l-naphthyl-phthalic acid,

5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate sodium salt,

4.6-dinitro-o-sec-butyl-phenol,

N- (phosphonomethyl) glycine and its _C-16 -monoalkil amine and alkali metal salts, and combinations thereof.

Ethers:

2,4-dichlorophenyl-4-nitrophenyl ether,

2-chloro-a, a, a-trifluoro-p-tolyl-3-ethoxy-4-nitro-diphenyl ether.

Other compounds:

2,6-dichlorobenzonitrile, monosodium salt of methanesulfonate, disodium salt of methanesulfonate.

Fertilizers that can be used in combination with the herbicidal compositions of the invention include, for example, ammonium nitrate, urea, potassium salt and superphosphate. Other useful additives are those in which the plants take root and develop. These include compost, farmyard manure, humus, sand.

Formulation of herbicidal compositions of the type described above is illustrated by the following examples.

I. Emulsifiable concentrates by weight

Example 1 is an active ingredient calcium dodecylbenzenesulfonate / polyoxyethylene ether mixture 50.0 (Atlox 3437F) calcium dodecylbenzenesulfonate 4.85 (FloMO 60H) 0.15 C ₉ aromatic solvent 45.00

100.00% by weight

B) The active ingredient of Example 4 is calcium dodecyl sulfonate / alkyl. 85.0 aryl polyether alcohol mixture 4.0 C ₉ aromatic hydrocarbon solvent 11.0 100.0 C.) Example 6 is an active ingredient calcium dodecylbenzenesulfonate / polyoxyethylene ether mixture 5.0 (Atlox 3437F) 1.0 xylene 94.0 100.0 Ti.Liquid concentrates THE) Example 4 is an active ingredient 10.0 xylene 90.0 100.0 B) Example 5 is an active ingredient 85.0 dimethylsulfoxide 15.0 100.0 C.) Example 6 is an active ingredient 50.0 N-methylpyrrolidone 50.0 100.0 D) Example 7 is an active ingredient 5.0 ethoxylated castor oil 20.0 Rhodamin B 0.5 dimethylformamide 74.5 100.0 III. emulsions THE) The active ingredient of Example 12 is a block copolymer of polyoxyethylene / polyoxypropylene with butanol. 40.0 (Tergitol XH) 4.0 water 56.0 100.0 B) The active ingredient of Example 13 is polyoxyethylene / polyoxypropylene 5.0 butanol block copolymer 3.5 water 91.5 100.0 ARC. Wettable powders THE) Example 1 is an active ingredient 25.0 Sodium ligninsulfonate 3.0 sodium N-methyl-N-oleyl taurate 1.0 amorphous silica (synthetic) 71.0 100.0 B) Example 12 is an active ingredient 80.0 sodium dioctyl sulfonate 1.25 calcium lignosulphonate 2.75 amorphous silica (synthetic) 16.00

100.00

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189,497

C) The active ingredient of Example 13 is sodium lignin sulphonate sodium N-methyl-N-oleyl taurate kaolinite chalk V. Porok A) The active ingredient of Example 7 is attapulgite weight% 10.0 3.0 1.0 86.0 100.0 2.0 98.0 100.0 B) The active ingredient of Example 8 is montmorillonite 60.0 40.0 100.0 C) The active ingredient of Example 9 is bentonite 30.0 70.0 100.0 D) The active ingredient of Example 10 is diatomaceous earth 1.0 99.0 100.0 VI. granules A) The active ingredient of Example 1 is granular attapulgite (20/40 mesh) 15.0 85.0 100.0 B) Diatomaceous earth (20/40 mesh) of Example 6 30.0 70.0 100.0 C) The active ingredient of Example 12 is bentonite (20/40 mesh) 0.5 99.5 100.0 D) The active ingredient of Example 13 is pyrophyllite (20/40 mesh) 5.0 95.0

100.0

VII. microcapsules

A) The active ingredient of Example 1 encapsulated in a polyurea shell 49.2 Sodium lignin sulfonate (Reax 88B) 0.9 Water 49.9

100.0

An effective amount of the herbicidal compositions of the invention is applied to the area in which the unwanted weeds are to be controlled. The amount of active ingredient to be used will depend on a variety of factors such as the species of plant and its stage of development, the type and condition of the soil, the amount of rain and the type of active ingredient used. In the case of selective application before emergence on plants or soil, the application rate is 0.02 to 11.2 kg / ha, preferably 0.04 to 5.6 kg / ha and 1.12 to 5.6 kg / ha, respectively. is in range.

% by weight

B) The active ingredient of Example 1 encapsulated in a polyurea shell 90.0 Sodium lignin sulfonate 0.5 water 95

100.0

C) The active ingredient of Example 12 encapsulated in a polyurea shell 10.0 potassium lignin sulfonate (Reax C-21) 0.5 water 89.5

100.0

D) The active ingredient of Example 13 encapsulated in a polyurea shell 80.0 lignin sulfonate magnesium salt (Treax LTM) 2.0 water 18.0

100.0

The herbicidal compositions of the invention containing the active ingredient acetanilide derivatives of the formula (I) as an active ingredient are applied in an effective amount to the soil or any aqueous medium used in the plants in a conventional manner. Liquid and particulate solid formulations are applied to the soil by conventional means, such as by machine spray, motorized or hand-held sprayers, and by spraying. The formulations may also be applied in the form of a powder or spray from an aircraft as they are effective in small doses. The herbicidal compositions of the present invention are used to treat the aquatic plants by adding them to the water in the area where it is desired to inhibit the development of the aquatic plants.

Claims (19)

Patent claims CLAIMS 1. A herbicidal composition comprising from 0.01% to 951% of the 2-haloacetanilide derivative of formula (I) as an active ingredient. R is C 1-5 alkyl, alkoxyalkyl, alkenyl or alkynyl; and - R, hydrogen, methyl or ethyl; with the proviso that in the event that Rj is hydrogen, R is isopropyl, and if R is ethyl, R is ethyl, n-propyl or isopropyl, solid carriers and diluents - preferably kaolin, attapulgite and diatomaceous earth - liquid diluents and solvents - preferably xylene and dimethylsulfoxide and surfactants, preferably sodium and calcium lignin sulfonates, N-methyl-N-oleyl taurate and ethoxylated castor oil. Composition according to Claim 1, characterized in that it contains an active ingredient in which R 2 is C 2 -C 4 alkyl. -181 189,497 Second 3. The herbicidal composition according to claim 2, characterized in that it contains an active ingredient having the formula: wherein R is methyl. The herbicidal composition according to claim 3, wherein the active ingredient is N-ethoxymethyl-2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide. 5. The herbicidal composition according to claim 3, wherein the active ingredient is N- (n-propoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide. 6. The herbicidal composition according to claim 3, wherein the active ingredient is N- (isopropoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide. 7. The herbicidal composition according to claim 3, wherein the active ingredient is N- (isobutoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide. 8. The herbicidal composition according to claim 2, wherein the active ingredient is a compound of formula (I) wherein R 1 is ethyl. The herbicidal composition according to claim 8, wherein the active ingredient is N- (ethoxymethyl) -2 '- (trifluoromethyl) -6'-ethyl-2-chloroacetanilide. 10. The herbicidal composition according to claim 8, wherein the active ingredient is N- (n-propoxymethyl) -2 '- (trifluoromethyl) -6'-ethyl-2-chloroacetanilide. 11. The herbicidal composition according to claim 8, wherein the active ingredient is N- (isopropoxymethyl) -2 '- (trifluoromethyl) -6'-ethyl-2-chloroacetanilide. 12. A herbicidal composition according to claim 2, characterized in that it contains as active ingredient a compound was ⁵ having formula (I) wherein R is hydrogen. 13. A herbicidal composition according to claim 12, wherein said compound is N- (isopropoxymethyl) -2 '- (trifluoromethyl) -2-chloroacetanilide ¹ 0 contains. 14. The herbicidal composition according to claim 1, wherein the active ingredient is a compound of formula (I) wherein R is a C 5 -alkenyl group. ¹⁵ 15. The herbicidal composition according to claim 14, wherein the active ingredient is N- (allyloxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide. 16. A herbicidal composition according to claim 1, ²⁰ characterized in that the active ingredient comprises a compound having the formula (I) wherein R up to 5 carbon atoms, alkynyl. 17. The herbicidal composition according to claim 16, wherein the active ingredient is N- (prop25 argyloxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide. 18. The herbicidal composition according to claim 1, wherein the active ingredient is a compound of formula (I) 30 R is an alkoxyalkyl group having up to 5 carbon atoms. 19. The herbicidal composition according to claim 18, wherein the active ingredient is N- (methoxyethoxymethyl) -2 '- (trifluoromethyl) -6'-methyl-2-chloroacetanilide.