PL125385B1 - Herbicide - Google Patents

Description

The subject of the invention is a herbicide containing 2-haloacetanilides as an active substance and conventional auxiliaries. The state of the art related to this invention includes numerous publications relating to 2-haloacetanilides unsubstituted or substituted with various substituents on the anilide nitrogen atom and on the anilide ring, including alkyl, alkoxy, alkoxyalkyl, halogen, etc. groups, in particular U.S. Patent Nos. 3,442,945 and 3,547,620. Particularly relevant disclosures contained in Patent Nos. 3,442,945 and 3,547,620 are the compounds 2 '-III-butyl-2-chloro-N-methoxymethyl-6'-methoxyacetanilide and its grommet analogue (examples 16 and 34 in patent description no. 3,547,620, 18 and 36 in patent description no. 3,442,945, respectively. United States Patent Nos. 4,070,369 and 4,152,137 disclose a general chemical formula which covers compounds of the type disclosed in said Patent Nos. 3,442,945 and 3,547,620. However, the only type of compound known from these patents is one having an alkyl group at one position. ortho and an alkoxy group in the second ortho position - has an alkoxyethyl radical on the anilide nitrogen atom; compounds of this type are discussed in more detail below. Other, less important prior art is described in Belgian Patent No. 810,763 and German Patent No. 2,402,983. The solutions known from these publications include compounds of the type discussed in the mentioned United States Patent Nos. 4,070,369 and No. 4152137 and are characterized by having an alkoxyalkyl group with two or more carbon atoms between the anilide nitrogen atom and the oxygen atom of the alkoxy residue. The more important elements of the disclosure from the Belgian patent description No. 810,763 and the German patent description No. 2,402,983 seem to be compounds having an ethoxyethyl group on the anilido nitrogen atom, a methoxy or ethoxy group in one ortho position and a methyl, ethyl or isopropyl group in the other position ortho (see Belgian patent no. 810763 compounds numbered 7, 13, 18-20 and 26, and others, of less importance - their homology, for example compounds numbered 6, 9, 16 and 17, which have methoxyethyl groups or methoxypropyl substituted at the nitrogen atom and a methoxy or ethoxy group in one ortho position and a methyl group in the other ortho position). The above United States Patent No. 3,442,945 covers certain data on the properties of the compounds mentioned above having a chemical configuration more closely related to the active compounds used in the invention and data on their homologues and analogues, for example for the compounds mentioned above - 3,125,885 4 in Belgian Patent Specification No. 810,763, numbered 6 and 9. More specifically, this most relevant information regarding herbicidal activity against various weeds does not disclose any data for any of the compounds described in this specification with additional and/or simultaneous herbicidal properties in relation to difficult-to-destroy narrow-leafed weeds, field foxtail, black oats and roof brome and other weeds such as trichinella, annual rye, common weed and red fingerweed, despite the fact that the mentioned Belgian patent no. 810763 gives data showing good control of black oats and unspecified species of various other weeds in sugar beets. A further disadvantage of many prior art herbicides is that they are limited in their applicability to particular soil types, i.e. some herbicides are effective ' in soils having a low content of organic substances, and at the same time they are ineffective in other soils with a high content of organic substances, or vice versa. It is therefore advantageous that the herbicide can be used on all types of soil, ranging from light to heavy clay and peat soils. Yet another disadvantage of some known herbicides is their lack of sustained weed control effectiveness during heavy rainfall, causing washout. herbicide from the soil. Finally, the disadvantage of some known herbicides is the need to develop and use special methods of handling due to their toxic properties. Hence, a further requirement is that the herbicide is safe during its use. Thus, The purpose of the invention is to develop a herbicide devoid of the above-mentioned disadvantages and disadvantages of known herbicides with various advantageous features compared to known herbicides, in particular a agent selectively combating various weeds, especially annual grass, including difficult-to-destroy narrow-leafed weeds such as foxtail, black oat and roof brome, as well as annual grasses such as hairwort, common weed, red fingerlings and annual rye, especially in sugar beets, effective in a wide range for various soils, from light soils to heavy clay and peat, and at the same time resistant to washing out in heavy downpours and safe, not requiring special methods of handling. The herbicide according to the invention contains at least one compound as an active substance having the general formula given in the attached drawing, in which R stands for an ethyl, n-propyl, isopropyl, isobutyl, allyl or butenyl group, Ri stands for a methyl, n-propyl, isopropyl, n-butyl, isobutyl group va or isoamyl and Rs is a methyl, ethyl or isopropyl group, wherein when R* is an isopropyl group, then R is a methyl, ethyl group and Ri is an n-butyl group, when Ra is an ethyl group, then R is an ethyl, n-propyl or allyl group and Ri denotes an n-butyl or isobutyl group when R denotes an n-propyl group, then Ri denotes an n-butyl or isobutyl group when Ri denotes an n-propyl group, then Ri represents an n-butyl or isobutyl group, when R represents an isopropyl group, then Ri represents an isobutyl group, when R represents an isobutyl group, then Ri represents an n-propyl, isopropyl group, isobutyl or isoamyl and when R is a butenyl group, then Ri is a methyl group. Compounds with the above formula are preferred: where R is an alkyl group with 2-4 carbon atoms, preferably an ethyl, n-propyl or allyl group, Ri is an alkyl group with 3 or 4 carbon atoms, preferably an n-butyl or isobutyl group, and Rt is a methyl or ethyl group. tf Particularly preferred active compounds used in the agent according to the invention are: N - (isobutoxymethyl)-2'-isopropoxy-6'-methyl-2-chloroacetanilide; N-(isobutoxymethyl)-2'-isoamyloxy-6'-methyl-2-chloroacetaniUd; N-(n-propoxymethyl)-2'-isobutoxy-6'-methyl-2-chloroacetanilide; N-(ethoxymethyl)-2'-n-butoxy-6'-isopropyl-2-chloroacetanilide; N-(isobutoxymethyl)-2'-isobutoxy-6'-methyl-2-chloroacetanilide; N-(isopropoxymethyl)-2'-isobutoxy-6'-methyl-2-chloroacetanilide; N-(isobutoxymethyl)-2'-n-propoxy-6'-methyl-2-chloroaceanilide; (2-butynyl-1-oxymethyl)-2'-methoxy-6'-methyl-2-chlorpacetanilide; N-(n-propoxymethyl)-2'-n-butoxy-6'-ethyl-2-chloroaceta-nilide; N-(allyloxymethyl)-2'-n-butoxy-6'-ethyl-2-chloroacetanilide; N-(ethoxymethyl)-2'-isobiitoxy-6'-ethyl-2-chloroacetanilide and N-(allyloxymethyl)-2'-isobutoxy-6'-ethyl-2-chloroacetanilide. It has now been found that the selected group 2- haloacetanilides of the given general formula, characterized by a specific connection of alkoxymethyl or alkenyloxymethyl groups at the anilide nitrogen atom, specific alkoxy groups in one ortho position and an alkyl group with 1-3 carbon atoms, i.e. a methyl, ethyl or isopropyl group , in the second ortho position, shows unexpectedly better and excellent selective herbicidal properties against weeds in sugar beet crops, compared to known herbicides, including the most significant known homologous compounds. Basic A characteristic feature of the herbicide 60 according to this invention is its ability to combat narrow-leafed weeds in sugar beets, especially difficult-to-destroy species such as black oats and foxtail, as well as less resistant species such as trichinella, common weed. 385 6 sided, red fingerlings, and other harmful weeds. Active compounds with the given general formula used in the product according to the invention can be prepared in various ways. For example, these compounds can be obtained by azometination as described in the above-mentioned patents. No. 3,442,943 and No. 3,547,620. In the azomethine process, the appropriate primary aniline 10 is reacted with formaldehyde to obtain the corresponding methyleneaniline (substituted phenylazomethine), which is then reacted with a haloacetylating agent such as chloroacetyl chloride or chloroacetic anhydride, which in turn is reacted with an appropriate alcohol to obtain the actual N-alkoxymethyl-2-chloroacetanilide as the final product. Another process for preparing active compounds of the given general formula requires N-alkylation of the anion the appropriate secondary 2-haloacetanilide with an alkylating agent under basic conditions. Example I illustrates the use of the above N-alkylation process to prepare one compound of the general formula given. A different N-alkylation process is described in Example II, which illustrates the preparation of another compound of the general formula given. The N-alkylation method described in Example II consists in the in situ preparation of halomethyl alkyl or halomethyl alkenyl ethers, used as starting materials in the N- n -alkylation process. Example I. 5.0 g (0.022 mol) were mixed in 250 ml of methylene chloride while cooling. 2'-isobutoxy-6'-methyl-2-chloroacetanilide, 4.75 g (0.44 mol) chloromethyl n-propyl ether and 2.0 g benzyl triethylammonium chloride. To the mixture, maintaining the temperature at 15°C, 50 ml of 50*/© NaOH solution was added immediately and stirred for 2 hours, then 100 ml of cold water was added. The layers were separated, washed with water, dried with 45 MgSO4, then evaporated and ground in keel mill, obtaining 6.5 g (90% yield) of light oil with a boiling point of 150°C at 5.33 Pa. Elemental analysis for C17H14CINO9 C/o): M Calculated: C-62.26; H-7.99; Cl-10.61; Found: C-62.27; H-Sfil; Cl-10.81. The product was identified as N-(n-propoxymethyl)-2)-isobutoxy-6,-methyl-2-chloroacetanilidt. Example II. This example describes a variation of the N-alkylation process described in Example 1. In this process, the alkylating agent is prepared in situ, which makes the process more effective, economical and simple to operate. 60 To a cooled mixture of 4.0 g (0.1 mole) of ethanol, 1.5 g (0.5 mole) of anhydrous paraformaldehyde and 100 ml of methylene chloride was added 6.1 g (0.05 mole) of acetyl bromide , and then the mixture was stirred until the raformaldehyde dissolved completely. Then 5.1 g (0.018 mol) of 2'-n-butoxy-6'-isopropyl-2-chloroacetanilide, 2.0 g of benzyl triethylammonium chloride and 40 ml of methylene chloride were added to the mixture. The mixture was cooled to 15°C and 50 ml of 50% NaOH solution was added immediately, then stirred for 2 hours. The layers were separated, washed with water, dried with MgSO4, then evaporated and ground in a ball mill, obtaining 4.0 g (77% yield) of a yellow liquid with a boiling point of 125°C at 6.66 Pa. Elemental analysis for CisHasCINOf (%): Calculated: C-63.24; H-8,26; Cl-10.37; Found: C-63.23; H-8,29; Cl-10.37. The product was identified as N-(ethoxymethyl)-2(-n-butoxy-6)-isopropyl-2-chloroacetanilide. Examples III-XII. Proceeding in essentially the same manner and under the conditions described in Examples 1 or 2, but substituting the appropriate secondary anilide and alkylating agent as starting materials and amounts thereof, the actual n-(alkoxymethyl or alkenyloxymethyl)-2-haloacetanilides were prepared, These compounds are identified in Table 1, along with their specific physical properties. The secondary anilides used as starting material in the above examples are prepared in a known manner, for example by haloalkylating the appropriate primary amine with a haloalkylating agent such as halide or haloacetyl anhydride. Typically, an appropriate amount of the appropriate primary amine is dissolved in a solvent such as methylene chloride containing a base, e.g. 10% NaOH, and mixed vigorously with a solution of the haloacetyl halide, e.g. chloroacetyl chloride, while cooling externally for e.g. temperatures 15-25°C. The layers are separated and the organic solvent layer is washed with water, dried and evaporated under reduced pressure. The primary amines used to prepare the secondary anilides can also be prepared in a known manner, for example by catalytic reduction of appropriate, suitably substituted nitrobenzene, for example 2 -alkoxy-6-alkylnitrobenzene, in a solvent such as alcohol, for example ethanol, using a platinum oxide catalyst. As noted above, the active compounds used in the composition according to the invention have been found to be herbicidally active, especially as pesticides before the plants emerge, although the activity of these compounds towards plants after their emergence has also been demonstrated. Pre-emergence testing relevant here includes greenhouse and field testing. In greenhouse tests, the herbicide is applied topically to sown seeds or to vegetative shoots, or by introducing the agent into a certain amount of soil to use as a covering layer for test seeds previously sown in test containers. In field tests, the herbicide may be6125 385 Table 1 Example No. III IV V VI VII VIII IX 2'-isobutoxy-6'-methyl-2-chloroacetanilide N-(2-butenyl-1-oxymethyl)-2'-methoxy-6'-methyl--2-chloroacetanilide N-(isobutoxymethyl)-2'- -isopropoxy-6'-methyl- -2-chloroacetanilide N-(isobutoxymethyl)-2'- -isoamyloxy-6'-methyl-2- -chloroacetanilide N-(isobutoxymethyl)-2'- -n-propoxy-6'- methyl-2- -chloroacetanilide N-(n-propoxymethyl)-2' - -n-butoxy-6'-ethyl-2- -chloroacetanilide N-(alloxymethyl)-2'- -n-butoxy-6'-ethyl- 2- -chloroacetanilide N-(ethoxymethyl)-2'- -isobutoxy-6'-ethyl~2- -chloroacetinilide N-(affloxymethyl)-2'-isobutoxy-6'-ethyl-2- -chloroacetanilide Empirical formula dsH^ ClNO, Q7HMClNOa C16HMC1N0, C17HaflClN03 C19HMCLNO, C17HI6C1N0, dgHMClNOa C18HMC1N0, Cl7H2flClNO, C18H26C1N0, Boiling point °C/Pa 115 (2.66 Pa) 120 (3.99 Pa) 114 (1.33 Pa) 1 20 (3.33 Pa ) 127 (10.66 Pa) 117 (2.66 Pa) 123 (5.33 Pa) 132 (9.33 Pa) 124 (2.66 Pa) Element C H Cl CH H Cl c H Cl c H N Cl c H Cl c H Cl c H Cl c H Cl c H Cl c H Cl Analysis ¦ Calculated value 63.24 8.26 10.37 62.28 7.99 10.81 60.50 6.77 11.91 62, 28 7.99 4.27 10.01 64.12 8.50 9.96 62.28 7.99 10.81 63.24 8.26 10.37 63.61 7.71 10.43 62.28 7 .99 10.81 63.61 7.71 10.43 Value 1 found 63.19 8.30 10.38 | 62.26 7.99 10.81 | 60.18 6.83 11.85 62.33 8.04 4.27 10.82 63.98 8.57 10.03 62.20 8.06 10.88 63.31 8.27 10.42 63, 60 7.74 10.42 62.27 8.02 10.82 63.61 7.71 10.45 applied before introducing the plant into the soil ("P.P.I"), i.e. the herbicide is applied to the soil surface , and then incorporated into the soil, after mixing, the seedlings or seeds, or the herbicide may be surface applied ("S.A.", surface application) after the introduction of the crop seeds. The surface application ("S.A") test method used in the greenhouse is the course is as follows: Containers, i.e. aluminum trays with typical dimensions of 24.13 cm X 13.34 cm cm, having drainage holes in the bottom, are filled to an even level with sandy-clay soil according to Ray, then compacted to a level of 1.27 cm from the upper edges of the vessels. Then the vessels are sown with the tested plant species and covered with layer 1 .27 cm of prepared soil. Then, the herbicide is applied to the soil surface, for example using a sprayer at a rate of 167 l/ha, at a pressure of 206.9 kPa. Each vessel receives 0.64 cm of water as necessary hydration, after which the vessels are placed in the greenhouse on shelves adapted, if necessary, for further subsoil irrigation, as an alternative procedure, additional subsoil irrigation may be omitted. Observations of herbicide effectiveness are made within approximately three weeks after application of the herbicide. Treatment with herbicide by soil incorporation ("S.I.") in greenhouse trials is as follows: Topsoil of good quality is placed with a small excess in aluminum containers and compacted to a depth of 0.95 to 1.27 cm from the upper edge of the container. A previously counted amount of seeds of vegetative suckers of various plant species is placed on top of the soil. After sowing the seeds or planting, the shoots of the uzu ¬ soil is filled to the required level in the trays. The soil and the known amount of the active ingredient used in a solvent or in the form of a wettable powder suspension are mixed carefully and used as supplementary soil in the prepared trays. After introducing the herbicide, 125 385 9 killing trough is initially sprinkled with water equivalent to 0.64 cm of rainfall, and then, if necessary for germination and development, the water supply is supplemented by irrigation of the soil. As an alternative treatment, additional subsoil irrigation may be omitted. Observations are carried out 2-3 weeks after sowing and applying the herbicide. Tables 2 and 3 present a summary of the results of the tests carried out to determine the herbicidal activity of the active compounds used in the herbicide according to the invention before the plants emerge. In these studies, herbicides were applied by applying them to the soil and irrigating only the subsoil; a dash (—) means that the indicated plant has not been tested. The herbicidal effectiveness rating was obtained using a 10-15-10 rating scale based on the percentage of destruction of each plant species. The indices are defined as follows: °/o destruction Indicator 0-24 0 25-49 1 50-74 2 « 75-100 3 Plant species used in one set of tests, data from which are presented in Table 2, are marked with the letter , as follows: A field thistle B burrow C woolly wheatgrass D purple quinoa E white quinoa F Ostrogorse knotweed G chaingrass H common couch grass I Aleppine millet J roof brome K unilateral weedgrass Table 2 Pre-emergence herbicidal effectiveness Compound from example no. I I H III IV V VI VII VIII IX 2 5.6 11.2 5.6 - 11.2 5.6 11.2 5.6 11.2 5.6 11.2 5.6 | 1 Plant species A 3 3 1 0 0 0 0 3 2 2 1 2 2 3 2 3 3 3 3 — — 3 2 3 2 | B 1 0 1 " — 0 0 0 1 1 0 1 1 0 0 1 2 0 1 0 0 1 1 — 0 1 1 c 2 2 2 2 1 ¦ 0 0 2 2 0 0 1 1 1 2 0 0 0 0 1 0 2 2 0 1 | D 2 2 2 1 0 3 0 2 2 1 3 1 2 1 1 2 2 and 0 0 1 0 2 2 1 1 | 1 E 3 3 3 3 1 2 2 3 2 3 1 3 3 3 3 3 3 2 2 2 3 3 3 3 1 1 1 F 3 2 3 2 1 3 1 3 2 2 1 3 3 2 2 3 3 1 1 2 2 2 2 3 1 1 ° 3 3 3 3 1 2 3 1 3 3 3 3 3 3 3 3 3 1 3 3 3 3 2 3 3 3 3 | 1 H 3 1 3 3 3 1 3 3 3 3 3 3 3 3 3 3 3 3 2 2 3 3 3 3 3 2 | I 3 3 3 3 0 1 3 2 1 1 0 3 0 0 1 3 3 1 0 3 3 1 1 3 1 1 1 J 3 3 3 3 3 3 3 3 - 3 3 3 3 3 3 3 3 1 3 3 3 3 3 3 3 3 3 1 1 K 3 13 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 3 1 The compounds were further tested using the above procedure on the following plant species: L soybean M sugar beet N wheat O rice P sorghum B turnip Q field buckwheat D purple grasshopper R hemp sesbania E white quinoa F Ostrogorse knotweed C woolly milkweed J roof brome S millet spp. pre-emergence herbicide Compound from example No. I II III IV V VI VII VIII ix 06 0.01 5.6 1.12 0.28 0.06 5.6 1.12 0.28 0.06 0.01 0.006 5.6 1.12 0.28 0.06 0.01 5.6 1.12 0.28 0.06 5.6 1.12 0.28 0.06 5fi 1.12 0.28 0.06 0.01 5.6 1.12 0.28 0.06 0.01 5fi 1, 12 0.28 0.06 0.01 5.6 1.12 0.28 0.06 0.01 5.6 1.12 0.28 0.06 0.01 Plant species L ~T 0 0 0 0 , 1 0 0 0 0 0 0 0 0 1 0 0 0 0 0 2 0 0 0 0 1 0 0 0 0 0 0 0 2 0 0 0 1 1 0 0 0 0 0 — 0 0 0 1 0 0 0 0 0 0 0 0 0 M r~ 1 0 0 0 2 1 0 0 0 1 0 0 0 2 1 1 0 0 0 2 2 1 1 1 2 1 1 0 2 1 1 1 2 1 0 1 0 2 0 0 0 0 2 1 1 0 0 2 1 1 0 0 3 1 1 0 0 N 3~~ 0 0 0 0 3 2 2 0 0 2 1 0 0 3 3 1 0 0 0 3 2 1 0 0 3 1 1 0 3 1 0 0 3 1 0 0 0 3 2 0 0 0 3 2 1 0 0 3 3 2 0 0 3 3 2 1 0 O 3~~ 3 2 2 1 3 3 2 1 0 2 3 0 0 3 3 2 1 0 0 3 3 3 0 0 3 1 1 0 3 2 1 0 3 1 0 0 0 3 3 1 0 0 3 2 2 0 0 3 3 2 1 1 3 3 1 1 0 P 3 3 3 2 0 3 3 2 0 0 3 3 0 Ó 3 3 3 1 0 0 3 3 1 0 0 3 3 2 0 3 2 0 0 3 3 1 1 0 3 2 1 0 0 3 1 1 0 0 3 3 2 0 0 3 3 0 0 0 B 0 0 0 0 0 3 0 0 0 — 0 0 0 0 0 0 0 0 0 0 2 3 3 1 0 1 0 0 0 2 0 0 0 2 1 0 — 1 0 0 0 0 0 0 0 0 0 0 1 0 0 0 — 1 0 0 0 0 Q 3 1 2 0 0 2 0 0 0 0 0 0 0 0 1 0 0 0 0 0 2 3 3 0 0 2 3 0 0 2 2 0 — 2 2 0 1 0 3 2 0 0 0 3 1 0 0 0 2 2 1 0 0 3 2 1 0 0 D 0 0 0 0 0 3 1 0 0 0 3 0 0 1 1 1 0 0 0 0 3 2 3 3 0 0 0 0 0 2 0 0 0 2 1 0 0 0 1 0 0 0 0 0 1 0 0 0 3 1 0 0 0 1 0 0 0 0 R 3~~ 1 0 1 — 2 2 0 — 0 2 0 0 0 3 3 0 0 — 0 3 2 1 2 3 2 0 0 0 2 0 0 0 3 3 1 1 0 2 2 0 0 0 1 0 0 0 0 3 3 3 0 3 3 2 0 0 0 E 3~~ 3 0 0 2 2 2 1 0 0 0 0 0 0 2 1 0 0 0 0 2 2 1 0 0 3 3 0 0 3 3 0 1 3 2 3 0 0 3 0 0 0 0 3 2 1 0 0 3 2 2 1 0 3 2 2 2 2 2 F ~3~ 2 1 0 1 3 2 1 0 0 0 0 0 0 1 0 0 0 0 0 2 2 0 0 0 3 3 0 0 3 2 0 0 3 2 2 1 0 3 1 0 0 0 3 1 0 1 0 3 2 0 3 — 3 1 3 3 3 C r~ 0 0 0 0 1 0 0 0 0 0 0 0 0 1 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1 0 0 0 0 2 2 0 0 0 1 0 0 0 0 T J 3 3 3 3 0 3 3 3 1 0 3 3 1 0 3 3 2 1 1 0 3 3 3 2 0 3 3 1 0 3 3 1 1 3 3 1 0 0 3 3 3 1 1 3 3 3 0 0 3 3 3 3 0 3 3 3 1 1 S 3 3 2 0 3 3 2 1 0 3 3 1 3 1 3 3 1 0 0 3 3 3 1 0 3 3 2 2 3 2 1 2 3 3 3 0 0 3 3 3 0 0 3 3 3 0 0 3 3 3 1 0 3 3 3 0 0 K 3~~ 3 3 3 2 3 3 3 3 1 3 3 3 1 3 3 3 3 1 1 3 3 3 3 3 3 3 3 2 3 3 3 1 3 3 3 3 2 3 3 3 3 0 3 3 3 3 0 3 3 3 3 0 3 3 3 3 ¦ 1 T 3~~ 3 3 3 3 3 3 3 1 0 3 3 3 2 3 3 3 3 2 1 3 3 3 3 3 3 3 3 2 3 3 3 2 3 3 3 3 3 — — — — — — — — -r — — — — — — 3 3 3 3 111 125 385 12 It has been discovered that the active compounds used according to the invention show unexpectedly better pre-emergence herbicidal properties when used against weeds in sugar beets, and more particularly in the selective control of difficult-to-destroy weeds. narrow-leafed grass, including foxtail, black oat and brome grass, and other weeds such as trichinella, annual rye, common weed and creeping fingerweed. Selective control and eradication of the above-mentioned and other weeds with the herbicide of the invention has been found in a variety of other crops, including soybeans, cotton, peanuts, green beans (bush beans), canola, cucumbers and tomatoes. However, the outstanding herbicidal properties of the active compounds of the given general formula are more obvious in the selective control of annual grasses in sugar beets. In order to illustrate the surprisingly improved properties of the active compounds used in the composition according to the invention, both on the basis of direct and relative tests, comparative tests were carried out in the greenhouse: (1) with known homologous compounds having a structure similar to the structure of the compounds of the general formula indicated above and used in the composition according to the invention and (2) with other compounds which, although not homologues, are within the scope of the state of the art and one of them has better properties as an active compound used in sugar beet herbicides, and two of them are industrial herbicides. All compounds in the above comparative tests are generally specified as substituted phenyl- N-hydrocarbyloxyalkyl-2-halo-acetanilides. As indicated in the tables, the known compounds compared therein are identified as follows: A. N-(methoxymethyl)-2'-methoxy-6'-ni-butyl-2-chloroacetanilide. (Example 18 in United States Patent Nos. 3,547,620 and 3,442,945). B. N-(methoxymethyl)-2'-methoxy-6'-tertiary-butyl-2-bromoacetanilide. (Example 34 of United States Patent No. 3,547,620 and Example 36 of United States Patent No. 3,442,945). C. N-(isobutoxymethyl)-2',6'-dimethyl-2-chloroacetanilide; common name "delachlor". (Example 31 of US Pat. No. 3,442,945 and Example 24 of US Pat. No. 3,547,620). D. N-(allyloxymethyl)-2'-dimethyl-2-chloroacetanilide (Example 47 of US Pat. No. 3,547,620) E. N-(methoxymethyl)-2',6'-diethyl-2-chloroacetanilide (Example 5 of US Pat. No. 3,547,620 and No. 3,442,945); common name "alachlor", active ingredient in the industrial herbicide "Lassoc" (registered trademark of Monsanto Co.). F. N-(methoxyethyl)-2'-methoxy-6'-methyl-2-chloroacetanilide. ( Compound No. 6 in the description of the mentioned Belgian patent No. 810763; also mentioned in the German patent No. 2402983). G. N-(ethoxyethyl)-2'-methoxy-6'-methyl-2-chloroacetanilide (Compound No. 7 of the Belgian patent No. 810,763.) 10 H. N-(1-methoxypropyl-2)-2'-methoxy-6'-methyl-chloroacetanilide. (Compound No. 9 of the said Belgian patent No. 810763). I. N-(methoxyethyl)-2'-ethoxy-6'-methyl-2-chloroacetanilide. (Compound No. 10 of said Belgian patent No. 810,763). J. N-(ethoxyethyl)-2'-ethoxy-6'-methyl-2-chloroacetanilide. (Compound No. 18 of said Belgian patent No. 810,763). K. N-(methoxyethyl)-2'-methoxy-6'-isopropyl-2-*-chloroacetanilide. (Compound No. 26 of said Belgian patent No. 810,763). L. N-(isopropoxyethyl)-2'-methoxy-6'-methyl-2-chloroacetanilide.M. N-(1-methoxypropyl-2)-2'-ethyl-6'-methyl-2- n -chloroacetanilide. (US patent no. 3,937,730 and German patent application no. 2,402,983); common name "metols-chlorine", active ingredient in the industrial herbicide "Duala (registered trademark of Ciba Geigy Corporation). Although the above-mentioned compound C is less similar in structure than the pesticidal homologues listed in the above descriptions, United States of America patent Nos. 3,442,945 and 3,547,620 because it does not have an alkoxy substituent in the ortho position, it was nevertheless included in these research trials because it showed better properties as a sugar beet herbicide compared to other compounds mentioned in US patents. No. 3,442,945 and No. 3,547,620. Likewise, compounds E and M are covered by this study because these compounds are within the scope of the prior art and have achieved industrial importance. Compounds F - L are included in the tests due to their certain similarity in structure with respect to some active compounds used in the composition according to the invention. In pre-emergence herbicidal tests, the active compounds used in the composition according to the invention were compared with the known compounds A - M regarding the effectiveness of controlling various weeds, with emphasis on the effect on annual narrow-leaved species, which are widespread weeds in sugar beets. The results of the research trials are presented below. The discussion of the data below is based on the dosage rates for the test compounds represented as "GRu" and "GRw". These dosages are given in kilograms per hectare (kg/ha). Gru means the maximum amount of herbicide required to cause 15*/# or es less crop damage, and GRii means nil-125 385 13 14 the minimum amount of herbicide required to achieve 85Vo weed inhibition. GR15 and GR8s are used as a measure of ¬ potential industrial action, understanding, of course, that suitable commercial herbicides may cause more or less damage to the plant within acceptable limits. A further indication of a chemical's effectiveness as a selective herbicide is the "selectivity coefficient" ("SF") for the herbicide in a given crop and weed. The selectivity coefficient is a measure of the relative degree of safety of yield and weed damage and is expressed as the GRis/GRss ratio, i.e. it is expressed by the ratio of the GRi5 index for the yield and the GRss index for the weed, both in kg/ha. In the tables below, the selectivity coefficients are given in brackets: the symbol "NS" indicates "non-selective"; a dash (—) after the weed used indicates marginal or indeterminate selectivity, that is, the actual GR15 and Aub GRM rates were higher or lower than the maximum or minimum rates used in the indicated samples. Since crop tolerance and control are related to themselves, the discussion of this relationship on the basis of the selectivity coefficient is significant. In general, it is desirable that crop safety factors, i.e., pesticide tolerance values, be high, since high herbicide concentrations are often desirable for one reason or another. Conversely, it is preferable that the weed control rates are low, i.e. that the herbicides have a high individual activity, from an economic and possibly ecological point of view. However, low herbicide application rates may not be sufficient to control some weeds and higher rates may be required. As a result, the best herbicides are those that kill the greatest number of weed species at the lowest herbicide dose and provide the highest degree of crop security, i.e., crop tolerance. Accordingly, selectivity coefficients (defined above) were used to quantify the relationship between crop security and weed destruction. With respect to selectivity factors listed in the tables, higher numerical values indicate greater selectivity of the herbicide in controlling the weed in a given crop. In the tables below, unless otherwise noted, data for compounds that have been tested in numerous trials have been average value for typical application rates, ranging from 0.14 to 2.24 kg/ha. Otherwise, different tables include data from single test trials for application rates as low as 0.07 kg/ha or as high as 4.48 kg/ha. Table 4 Compound GR15 Index (kg/ha) GRM Index ( kg/ha) .07 (- <0.14 O 7.2) < 0.14 ( 14.6) < 0.14 (16.0) < 0.14 O 11.0) Field foxtail 0.07 (8.0) 0.07 (40) 0.28 (3.0) 0.14 (NS) 0.07 (NS) 0.07 (NS) 1.87 (NS) <0.14 O 14.6) < 0, 14 O 16.0) < 0.81 O 1.9) 8 'i o A B O F G L M Example P Example ni* Example 0.56 0.28 0.84 <0.07 0.07 <0.07 1.01 2fi5 2M 1.54 0.56 (1.0) 0.14 (2.0) 0.80 (1.1) 0.28 (NS) 0.28 (NS) 0.38 (NS) 1.68 (NS ) 0.44 O 4.7) 0.84 (2,T) 0.70 (2.2) 0.14 (4.0) <0.07 O 4.0) <0.14 ( 6.0 ) <0.07 (-) <0.07 (-) <0.07 (-) < 0.14 O 7.2) <0.14 O 14.6) <0.14 ( 16.0) < 0.14 011.0) 0.08 (7.0) <0.07 O 4.0) 0.14 (6.0) <0.07 (-) <0.07 (-) <0.07 (-) <0.14 O 7.2) <0.14 O 14.6) 0.14 (16.0) <0.14 O H,Q) * Data are the average of two repetitions. b The data are the average of three repetitions.125 15 In the first series of tests, the data for herbicidal activity before dew emergence are . presented in Table 4, which compares the relative effectiveness of the active compounds used in the present invention with similar compounds known as selective herbicides against particular weeds commonly associated with sugar beets. l Weeds used in these research trials are identified in the tables with the following abbreviations; owTies deaf, one-sided weedweed, red milkweed, field foxtail and trichinella. Regarding the data in Table 4, it can be noted that in terms of crop safety (as demonstrated by the GR15 index for sugar beets), the active compounds used in the product according to the invention show distinctive superiority compared to the known compounds that are most similar in terms of structure, i.e. compounds A and B having the N-alkoxy-methyl-2'-alkoxy-6'-alkyl-2-haloacetanilide configuration. In the research sample, the active compounds used in the agent according to the invention were from 5.8 to more than 8.0 times safer for sugar beets than compound B and from about 2.8 to more than 4.0 times safer than compound A. Even more noteworthy is that the active compounds used in the present invention were 22 to more than 32 times safer for sugar beets than the homologous compounds of the known prior art compounds F, C and L, each of which caused more than 15% of dyes in sugar beets at a very low dose, less than 0.07 kg/ha. Although it is not a homolog of the active compounds used in the product according to the invention, compound C is known for its distinctive properties as a herbicide adapted to the cultivation of sugar beets. as compared to the other compounds discussed in the above-mentioned United States Patent Nos. 3,442,945 and 3,547,620, which also discuss compounds A and B. Similarly, although compound M is not a homologue of the active compounds used in the present invention, is listed in German Federal Patent Application No. 2,402,983 which also discloses compounds F and G and generally includes compound L. Compound M is the active ingredient in an industrial herbicide as indicated above. Regarding the GRi5 dose data in Table 4 for C IM compounds, it should be emphasized that these compounds are characterized by a higher safety factor than other compounds from the state of the art. However, Compound C was only about one-third to one-half as safe as the active compounds used in the present invention and Compound M was only about one-third to two-thirds as safe as the active compounds used in the present invention. invention. Simultaneously with the indicated higher degree of safety for cultivation, the active compounds 385 16 used in the composition according to the invention provide unit activities (for example, phytotoxicity per unit of herbicide substance) against the tested weeds (as indicated by the dose values of 5 GR65) more or less comparable with the appropriate activities of known compounds. A high yield safety index and high individual activity against weeds guarantee unexpectedly higher selectivity indices for the active compounds used in the agent according to the invention compared to the selectivity indices for known compounds, with one exception 15 From the entry given in Table 4, comparing the selectivity indices of known compounds with the same indices for the weed of Example 1, in relation to the corresponding weeds in sugar beets, the compound of example I 10 was more selective than the known compounds, which is expressed in factors ranging from about 2.4 to more than 4.7 for deaf oats, from about 2.1 to more than 14.6 for yellow oat and from 1.8 to above 14.6 against the red foxtail and foxtail. Additional tests with selected active compounds used in the product according to the invention showed their effectiveness in combating the red foxtail weed, the sour foxtail, the foxtail and the trichinopsis, by these compounds in at doses as low as or even lower than 0.07 kg/ha. Thus, the compound of Example I is characterized by effective control of each of the above weeds at a dose of 0.07 kg/ha or less. The compound of Example IV is characterized by effective control of single-sided weed, red fingerlinger and trichinopsis at a dose of less than 0.07 kg/ha, and the compound of Example VI is characterized by effective control of single-sided weed and red-tailed weed at a dose of 0.07 kg/ha or less. In other comparative studies, the pre-emergence herbicidal activity and selectivity indices of the compounds from the state of the art: C, E, H and M were determined and the data for the compounds from Examples I-VIII were compared with them. The obtained results are presented. in Table 5. Regarding the data in Table 5, it is emphasized that each active compound used in the agent according to the invention showed a significantly higher safety index in sugar beets than all known compounds. Special attention is paid to the safety indexes of the compounds from Examples I, III , VI-VIII, which for the active compounds used in the agent according to the invention are higher by 2.2 to more than 16 times. Moreover, apart from having higher safety indices, the active compounds used in the agent according to the invention show only examples, uniformly significantly higher selectivity coefficients than known compounds. Thus, the selectivity coefficients of compound C were slightly higher than the coefficient for the compound from Example VII towards dry oats, and slightly higher than the coefficient for the compound from Example 17 125 385 18 Table 5 Compound O B H MP ~ Example Ib Example II 1 Example III Example IV Example V Example VI Example VII Example VIII Dose GR15 (kg/ha) Sugar beets 0.84 <0.14 < 0.14 1.01 2.05 1.12 2.24 1.54 1.12 2.24 2.24 2.24 * Hollow oats 0.80 (1.1) 0.56 (NS) 0.86 (NS) 1.68 (NS) 0.44 O 4.7) 0 .56 (2.0) 0.84 (2.7) 0.70 (2.2) 0.42 ( 8.0) 1.12 (2.0) 2.24 (1.0) 1.68 (1.3) GR85 dose (kg/ha) 8 1 Chwastni unistro < 0.14 O 6.0) < 0.14 (-) < 0.14 (-) < 0.14 ( 7.2) <0 ,14 O 14.6) <0.14 O 8.0) <0.14 O 16.0) <0.14 O n,o) <0.14 O 8.0) <0.14 O 16, 0) <0.14 O 16.0) <0.14 O 16.0) Red fingerlingus < 0.14 ( 6.0) < 0.14 (-) < 0.14 (-) < 0.14 O 7.2) < 0.14 O 14.6) < 0.14 ( 8.0) < 0.14 O 16.0) < 0.14 O n,o) <0.14 O 8.0) < 0.14 O 16.0) <0.14 O 16.0) <0.14 O 16.0) K Grasshopper 0.28 (3.0) 2.24 (NS) 1.12 (NS) 1 .87 (NS) <0.14 (14.6) 0.14 (8.0) <0.14 O 16.0) 0.81 O 1.9) 0.42 O 8.0) 0.38 (3.0) 0.56 (4.0) 0.56 (4.0) Trichinella lutea 0.14 (6.0) < 0.14 (-) < 0.14 (-) < 0.14 O 7.2) < 0.14 O 14.6) < 0.14 O 8.0) < 0.14 O 16.0) < 0.14 O n,o) <0.14 O 8.0) < 0.14' O 16.0) < 0.14 ( 16.0) 0.14 (16.0) | The data represent the average of two replicates of clade IV and are equal to the coefficient for the compound from Example VI in relation to foxtail. It should be noted that the known compounds E, H and M do not show yield selectivity towards deaf oat and foxtail and compound selectivity. E and H for the remaining weeds were questionable or marginal at best; in any case, the low safety factors of these compounds make them unsuitable as herbicides for use in sugar beet cultivation. Since the herbicidal data for pre-emergence applications given in Tables 4 and 5 were obtained according to identical established methods procedure, comparison of the herbicidal effectiveness of the active compounds used in the product according to the invention from Table 4 with the effectiveness of known compounds listed in Table 5 and not listed in Table 4 and vice versa. Here again, it has been clearly demonstrated that each of the active compounds used in this invention has surprisingly outperformed without exception all of the most significant prior art compounds in terms of yield safety and selective kill. from three replicates of the weed, as demonstrated by the selectivity coefficients, except in isolated cases. Thus, the selectivity coefficient of a particular known compound for some weeds may be higher than for the particular active compound used in the composition according to the invention, but in each In this case, the low safety factor for sugar beet makes the known compound unsuitable as a herbicide for use in sugar beet cultivation. For example, the selectivity factor (2.0) for compound B (Table 4) towards deaf oats in sugar beet is higher than for the compound of Examples 7 and 8 (1.0 and 1.3, respectively, as indicated in Table 5). However, the safety coefficients for sugar beets of both compounds from Examples 7 and 8 are 8 times higher than the coefficient for compound B, and the selectivity coefficients of the compounds mentioned according to the invention are at least 4 times higher than those of compound B towards the weed weed, red foxtail and trichinella and are equivalent to the selectivity coefficient of compound B towards foxtail. In yet another comparative study for herbicidal activity, the compound of Example I and compounds I and J were tested against black oat, weedwort. unilateral, red fingerling, foxtail and trichinella. The test results (showing the average of two trials) are given in Table 6. Observations were made approximately 18 days after treatment. Selectivity coefficients are shown in parentheses below the GR85 dose for each weed. 10 Data from test trials show that the known compounds I and J were harmful to sugar beet at rates as low as 0.07 or lower and that compound I was non-selective on brome grass and annual rye, however, compound J was non-selective towards brome grass. On the contrary, the compound of Example I was safe for sugar beet at a dose of 1.12 kg/ha (the maximum dose in the trial) and selectively controlled the roof brome grass. Table 6 Compound Example I * J Dose GR15 (kg/ha") Sugar beets < 1.12 <0.28 < 0.21 Hollow oats 0.35 (3.2) ~ 0.99 (NS) 0.28 (NS) GRe dose, (kg/ha) S § Chwastnia unistro 0.14 O 8.0) < 0.14 (-2.0) <0.14 (- 1.5) Red fingerlings <0.14 O 8.0) < 0.14 (-2.0) <0.14 ( ~ 1.5) « Grasshopper <0.14 O 8.0) 0.21 (-1.3) 0.21 (NS) Yellow foxtail < 0.14 O 8.0) < 0.14 (-2) ,0) < 0.14 (-1.5) and The distinctive advantage of the compound from Example I over compounds I and J is revealed when comparing the yield security index and selectivity towards each weed in the test sample. Compound J was non-selective in sugar beets in relation to foxtail oats and foxtail, and compound I was non-selective in relation to deaf oats and selective to a narrow extent in relation to foxtail. In one of the subsequent tests, the compound from Example I and compounds I and J were additionally tested in sugar beets in relation to brome grass, prickly amaranth and annual rye, using doses ranging from 0.07 to 1.12 kg/ha. Observations were made 18 days after administration of the compound. The results from this trial are presented in Table 7; selectivity coefficients are given in brackets under each weed. Table 7 40 45 Compound Example I I J GRu dose (kg/ha) Sugar beets 1.12 0.07 <0.07 GR66 dose (kg/ha) Roof brome 0.07 ( 16.0) 0.14 (NS) <0.09 (NS) Prickly amaranth 1.12 (-) 0.07 (1.0) <0.07 (-) Rye 1 annual | 0.09 (12.0) 0.28 (NS) (-) 1 69 and annual rye with selectivity coefficients of about 16.0 and 12.0, respectively, although control of the prickly amaranth was little or insignificant at the dose above 1.12 kg/ha. Further testing was carried out in a greenhouse in order to compare the active compounds used in the product according to the invention from Examples II and V with compounds K and D, respectively, i.e. the most similar compounds from the state of the art. Compound from Example II and compound K is characterized by an isopropyl radical in the ortho position and an alkoxy radical at the anilide nitrogen atom. Compound D and the compound from Example V are characterized by alkenyloxymethyl radicals attached to the nitrogen atom and a methyl radical in one ortho position. The herbicidal compounds were applied to the plants at doses ranging from 0.07 to 1.12 kg/ha. Observations were made 19 days after treatment with the compounds. The results are presented in Table VIII. Comparison of the data in Table 8 clearly indicates a distinctive feature. advantage of the active compounds used in the product according to the invention over compounds D and K. In particular, the compounds from Examples II and V were safe for sugar beets at a dose of 1.12 kg/ha and higher, while for compounds D and K the dose GR« was only 0.9 kg/ha. Moreover, in sugar beets, the selectivity coefficients of the active compounds used in the product according to the invention were several times higher than the selectivity indexes of known compounds in relation to each tested weed, and the known compounds were non-selective in sugar beets in relation to foxtail. . r .21 125 385 Table 8 22 Compound Example II 1 K Example V (2.7) 0.14 (8.0) 0.19 (1.0) GRa5 dose (kg ha) One-sided weed <0.07 (16.0) <0.07 (2.7) <0, 07 1 016.0) 1 <0.07 1 (2.7) ! ii <0.07 (16.0) -.07 , (2.7) 1 <0.07 016.0) <0.C7 (2.7) Field foxtail 0.24 (4.7) 0 .49 (KS) 0.78 (1.4) 0.56 (NS) ^1 Trichinosis <0.07 016.0) 0.07 (2.7) 1 0.09 1 (11.1) <0 .07 (2.7) 1 Other* research tests were carried out in order to demonstrate better herbicidal properties of other active compounds used in the product according to the invention. In a series of greenhouse tests, the compounds from Examples IX-XII were tested against black oats, common weed, red fingerling, foxtail and trichinella occurring in sugar beets. The results of these tests are presented in Table 9. 0.07 kg/ha. For example, the compound of Example I showed selective control of more resistant weeds, such as foxtail and roof brome, and less resistant weeds, such as trichinopsis and annual rye, at rates only up to 0.07 kg/ha and lower. Similarly, other active compounds used according to the invention also controlled one or more of the above less resistant weeds at 0.07 kg/ha. Table 9 Compound GR15 dose (kg/ha) GRM dose (kg/ha ) i i li 8 Example IX* Example 84 OW) <0.14 (7.1) <0.14 08.0) <0.14 08.0) <0.14 08.0) <0.14 (7.1) <0.14 ( 8.0) <0.14 (8.0) 0.14 (8.0) 0.19 (5.2) <0.14 (8.0) <0.14 (8.0) 0.14 O*,0) <0.14 (7.1) <0.14 (8.0) <0.14 (8.0) 0.14 (8.0) Data represent the average of four repeated samples b Data represent average of two repeated trials c The data represent the average of three repeated trials. As emphasized, the data for the tested compounds in many series were obtained from tests at herbicide application rates ranging from 0.14 to 1.12 kg/ha. However, additional tests with selected active compounds used according to the invention showed safety for sugar beet at doses of at least 4.48 kg/ha and selective control of various weeds at doses only up to salt. Again, better herbicidal activity before emergence plants of the active compounds used in the composition according to the invention have been demonstrated both directly and with respect to the effects of significant compounds from the prior art, as shown in Tables 4-4 with respect to indicators of crop safety, weed control activity and selectivity in pbn - weed ratio. 125 365 23 24 In a field test to meet the requirements of sugar beet safety and weed control, the compound of Example I and compounds C, E and M from the prior art were tested in relation to the weed weed and the weed weed. green under surface application conditions ("S.A.") and before introducing the plant into the soil ("P.P.I.") at doses ranging from 1.12 to 4.48 kg/ha. The effect of the compound was tested on Ray's sandy-clay soil with a content of 1.8% of organic substances. Conditions were relatively dry as there was only 0.3 cm of rainfall during the first 7 days after treatment with the compound. The results of the field test are presented in Table 10. With respect to the data in Table 10, it should be noted that of all the compounds tested, only the compound from Example 1 was safe (that is, damage up to 15°C) for sugar beets at doses of at least up to 4.48 kg/ha (maximum dose in the trial), showing selective destruction of both witchweed and green trichome at a dose of 1.12 kg/ha under PPI conditions. No known compound has selectively controlled any weed even at 2.24 kg/ha; These compounds under PPI conditions, even at a dose of 1.12 kg/ha, did not selectively kill weeds, beyond the barely permissible tolerance limit of the crop plant. The compound from Example I was also tested under field conditions to determine its selectivity before plant emergence. in relation to trichinella (spp.), common weed and wild millet, in most cultivated plants. The data (average of three repeated trials) are presented in Table 11 under both surface application (SA) and soil application (PPI, i.e. pre-emergence) herbicide conditions. The seeds were placed in a fine-grained layer of dusty and sandy soil with average humidity, at a depth of 5.08 cm. The first rainfall of 0.51 cm occurred the day after the plants were treated with the compound, the second rainfall of 0.64 cm occurred 2 days after the treatment. Table 10 Compound Example I C E M Dose (kg/ha) 1.12 2.24 4.48 1.12 2.24 4.48 1.12 2.24 4.48 1.12 2.24 4.48 Percentage of development inhibition Sugar beet PPI 0 10 12 10 22 57 30 80 100 15 30 63 SA 0 3 13 5 18 25 30 63 90 15 23 45 Beetroot PPI j SA 85 92 98 78 87 98 87 100 100 95 100 100 27 48 78 42 77 96 68 95 98 40 78 93 Trichinella 1 green PPI 85 92 98 88 93 98 88 100 100 95 100 100 SA | 57 65 85 77 87 88 85 95 97 62 85 92 | Table 11 Compound Application method Dose (kg/ha) Percentage of development inhibition! I £ Example I S.A.P.P.I. 0.58 1.12 2.24 4.48 0.58 1.12 2.24 4.48 1 o 0 0 7 0 5 5 43 0 0 1 10 0 0 0 5 40 0 o o 3 0 3 0 17 0 0 0 0 0 0 0 o o o o o 3 Ó 13 33 82 93 93 63 75 90 97 33 82 93 93 63 85 97 20 100 25 17 50 *325 125 385 rain, the total rainfall within 22 days after the treatment of the plants was 4 .57 cm. Observations were made 6 weeks after treatment of the plants. The data in Table 11 indicate that the compound from Example 1 generally performs under both SA and PPI conditions, at doses up to 4.48 kg/ha (except for tomatoes). , cucumbers and wheat weed 4.48 kg/ha under PPI conditions and in relation to wheat weed and wheat weed at 0.58 kg/ha). More specifically, under SA conditions, the compound of Example 1 selectively controlled trichinopsis and wheat weed in all crops at rates slightly above 1.12 kg/ha and wheat weed at 4.48 kg/ha. Under 15 PPI conditions, the common weed was selectively destroyed at 1.12 kg/ha and the trichinella was selectively destroyed between 1.12 and 2.24 kg/ha at crop safety, except for tomatoes, cucumbers and bush beans. 20 A distinct advantageous feature. A compound with herbicidal properties is its ability to act in various types of soil. Accordingly, data are given in Table 12 showing a comparison of the effect of the compound of Example 25 I and the known compounds C and M on various annual sugar beet grasses in a wide variety of soil types with different organic matter and clay contents. In these tests, the pots were filled with 50 Ray of dusty-sandy soil, compacted to 0.95 cm from the pot surface, and then sown with sugar beet, black oats, common weed, red fingerling, foxtail and trichinella. The seeds were covered with a layer of 1.27 cm of soil in the following order: silt-sandy-clean Ray, Florida peat, Florida sand, loamy sand, Wabash loam, Drummer loam or Sarpys loam each compound introduced using a belt sprayer in the amount of 187 l/ha at a pressure of 206.92 kPa, under surface application conditions. Each pot received 0.64 cm of water before being placed on benches in the greenhouse for further subsoil irrigation. Observations were made 15 days after treatment with the compound. The results of soil tests, which are the average of two repeated tests, are presented in Table 12; Selectivity coefficients are given after the GR dose for m weeds. The composition of the soil types was as follows: Comparison of the data in Table 12 indicates that the compound from Example I shows greater safety for sugar beets and higher coefficients. selectivity than compounds C and M for each weed (but with two minor exceptions) in three of the five soils, i.e. silt-sandy Ray, sandy Florida and loamy Wabash. More specifically, the compound of Example I was the only selective compound controlling black oat in a silt-sandy Ray and Wabash loam, one-tailed weedweed in a Florida sand, and foxtail in a Wabash clay loam. Stems in Florida peat (22.1°/o organic matter) « Percent Type Soil organic substance Clay Mul Sand pH Dust-sand Ray 1.2 0.4 74.8 18.8 6.5 Florida peat 22.1 NA ** NA» NA* 5.2 Florida Sand (Leon) 2.3 1.8 NA* NA* 6.1 Loam Drummer 3.6 12.4 32.8 34.8 7.0 Wabash Clay 2.7 44.4 34.8 20.8 6.2 a — unattainable. were rather unclear, but they indicate that the high content of organic matter in soils tends to reduce the activity of each of the tested compounds. The compound of Example 1 did not have the same effect in clay Drummer as the prior art compounds, but showed higher activity in a range of soil types. Laboratory tests were carried out to determine the relative resistance of herbicidally active compounds used in the agent according to the invention and the compounds from the prior art on leaching into the soil and, therefore, on herbicidal effectiveness. In these tests, the compound of Example I and compounds C and M were prepared in acetone and then sprayed at various concentrations into a weighed amount of Ray's silt-sandy soil contained in pots with drainage holes in the bottom covered with filter paper. . The pots containing the treated soil were rinsed by being placed on a swivel base that rotated under two tank water outlets rated to deliver 2.5 cm of water per hour, simulating rainfall. The swing speed was regulated by varying the time it was held on the rotating base. Water supplied to the soil in the pots permeated through the filter paper and drainage holes. The pots were then left for 7 days at ambient room temperature. The treated soil was then removed from the pots, crushed and placed as a surface layer on top of other pots containing Ray's silt-sandy soil sown with seeds of sugar beet, black oat, red oat, red fingerling, foxtail and trichinella. The pots were then placed on greenhouse benches that irrigate the subsoil and allowed to develop for 2 weeks. Visual assessments were recorded in percentage of development, and the data for the tested compounds are the average of 2 replicates. Abbreviations for weeds are as in the previous tables. Comparison of the data in Table 13 will indicate that27 125 385 Table 12 28 Soil type and compound Dust sand. Ray from example I C M Florida peat from example I C M Florida sand from example I C M Wabash clay from example I C M Drummer clay loam from example I C M Dose GR15 (kg/ha) Sugar beets 2.24 0.56 0.28 2.24 2.24 2 .24 2.24 1.12 1.12 2.24 0.38 0.38 0.56 1.12 1.68 ii "w ftT.Oats j 1.12 (2.0) 1.12 (NS) 1.12 (NS) 2.24 (-) 2.24 (-) 2.24 (-) 2.24 (-) 2.24 (NS) 2.24 (NS) 1.12 (2.0) 1.12 (NS) 1.12 (NS) 2.24 (NS) 1.12 (1.0) 2.24 (NS) GRC dose, /keha nica onna Chwasti Jednosti <0.14 016.0) < 0.14 (4.0) <0.14 (2.0) 2.24 (-) 2.24 (-) 2.24 (-) 1.12 (2.0) 2.24 (NS) 2 .24 (NS) 0.21 010.7) 0.14 (2.7) 1 1.14 (2.7) 0.52 (1.1) 0.28 (4.0) 0.28 (6 .0) | * (-) Jn 1:12 | (2,0) | 142 (1.0) 2.24 (NS) <0.14 (16.0) 0.56 (NS) ' 1 0.28 (1.4) 0.56 ' (1.0) 0.56 (2, 0) 0.96 01.8) ! .( .g Field performance 0.14 (16.0) 0.14 (4.0) 0.56 (NS) 2.24 (-) 2.24 (-) 2.24 (-) 2.24 ( -) 2.24 (NS) 2.24 (NS) 0.23 (9.7) 0.56 (NS) 1.68 (NS) 2.24 (NS) 1.12 (1.0) 2, 24 (NS) i !P i '£ i *2 <0.14 (16.0) <0.14 1 (4.0) <0.14 (2.0) 2.24 01.0) 2, 24 01.0) 2.24 (-) 1.07 (2.1) 1.12 (10) 0.56 (2.0) 0.21 010.7) (2.7) 0.14 (2.7 ) 0.43 (1.3) 0.28 (4.0) 0.56 (3.0) | the compound of Example I was safe for sugar beets up to at least 2.24 kg/ha and selectively destroyed all weeds in the 10.16 cm rainfall test, except for dull oats, which were destroyed at 7. 62 cm of rain. At 2.24 kg/ha, compounds C and M were harmful to sugar beets until diluted in 5.00 cm of rain, under which conditions neither compound C selectively destroyed deaf oats nor compound M selectively destroyed foxtail. the lowest application dose of the herbicide of 0.14 kg/ha, the compound from Example I selectively* destroyed all weeds during the test with a rainfall of up to 1.27 cm, and one-sided weedweed, red fingerlings and trichinella at 5.08 cm rainfall. On the contrary, at 0.14 kg/ha neither compound C nor compound M selectively destroyed foxtail and, furthermore, compound C did not destroy wild oats under all rainfall conditions, and both compounds lost their leivity towards all tested weeds in sugar beet at 5.00 cm of rainfall. Thus, it is clearly indicated that the active compound used in the composition according to the invention was, under variable rainfall conditions, significantly more resistant to leaching into the soil than any of the known compounds, thus enabling a more reliable and prolonged herbicidal activity. Finally, in order to further demonstrate the unexpected characteristic and unexpectedly improved properties of the active compounds used according to the invention, further pre-emergence herbicidal data for other compounds with a similar structure including compound homologies are presented in Table 14 this invention. The N - T compounds in Table 14 are identified as follows: 185 385 29 N. N-(isopropoxymethyl)-2'-rnethoxy-6'-methyl-2-chloroacetanilide; O. N-(isobutoxymethyl)-2'-ethoxy-2-chloroacetanilide; P. N-(isobutoxymethyl)-2'-methoxy-2-chloroacetanilide; Q. N-(isobutoxymethyl)-2'-methoxy-6'-methyl-2-30-chloroacetanilide; R. N-(ethoxymethyl)-2'-methoxy-6'-methyl-2-chloroacetanilide; S. N-(1-methylpropoxymethyl)-2'-methoxy-6'-methyl-2-chloroacetanilide; T. N-(ethoxymethyl) - 2'-isopropoxy - 6'-methyl-2- -chloroacetanilide. Compound Example I C M 1 1 L 1 Dose *g/ha) 2.24 0.56 0.14 2.24 0, 56 0.14 %24 0.56 044 1 Rain (cm) 1 ° 1.27 2.54 5.08 10.16 0 1.27 2.54 5.08 10.16 0 127 2.54 5.08 10.16 0 1.27 2.54 5.08 10.16 0 1.27 2.54 5.07 10.16 0 1.27 2.54 5.08 10.16 0 1*27 2.54 5 .08 10.16 0 127 2 £4 5.08 10.16 0 1.27 2.54 5.08 10.16 1 Table i 13 Percentage of stunted development 1 | Beetroot 1 10 15 10 10 10 0 0 0 0 0 0 0 0 0 0 30 40 40 15 0 15 25 10 0 0 10 0 0 0 0 40 30 20 10 10 15 15 0 0 0 0 0 0 0 o 1 ! xi gluc Oats 1 100 100 100 95 75 95 95 95 85 30 85 85 75 50 30 100 100 95 30 20 95 85 50 85 15 50 30 30 30 30 85 95 85 30 30 85 40 50 20 0 85 50 40 0 1 s i Chwaa unity 1 100 100 100 100 100 100 100 100 100 75 100 100 95 95 50 100 100 100 95 75 100 100 95 75 30 and 95 95 85 65 0 100 100 10 0 95 60 100 100 95 75 30 95 95 75 60 0 | 0 | ! Bloody fingerling 1 100 100 100 100 85 100 100 100 95 20 95 95 95 85 30 100 100 100 95 50 100 95 85 65 30 , 95 85 60 40 30 100 100 100 85 50 100 100 95 85 40 95 85 50 30 o 1 Field foxtail 1 100 100 100 100 90 100 100 100 95 20 95 95 75 75 20 100 100 95 85 20 95 95 75 50 20 40 40 20 20 0 95 85 60 30 15 95 65 30 20 0 75 60 30 0 o 1 yellow 1 *N i . § Wlosn 1 10° 100 100 100 95 100 100 100 100 50 100 100 100 95 50 100 100 100 95 50 100 ' 100 95 95 50 95 85 85 75 40 100 100 100 95 50 . 100 100 95 75 20 100 95 95 0 o 131 125 385 Table 14 32 Compound Na 0 P Q R S Ta Dose GRU (kg/ha) Sugar beets <0.14 <0.14 <0.14 <0.14 <0.07 0.14 0.23 Hollow oats ¦ 0.14 (NS) 2.24 (NS) 2.24 (NS) 0.28 (NS) 0.09 (NS) 0.49 (NS) 1 0.26 ( NS) | GRa5 dose (kg/ha) One-sided weed <0.14 (-) <0.14 (-) 0.14 (NS) | <0.14 (-) 1 <0.07 (-) <0.07 (2.0) <0.14 (1.6) Red fingerlings <0.14 (-) <0.14 (-) 0 .14 (NS) <0.14 (-) <0.07 (-) <0.07 (2.0) <0.14 01.6) Field foxtail 0.14 (NS) 1.90 (NS) 0.56 (NS) 0.14 (NS) 0.07 (NS) 0.14 (1.0) 0.12 (1.9) | Trichinella lutea <0.14 (-) 0.14 (-) 0.28 (NS) <0.14 (-) <0.07 (-) <0.14 (1.0) <0.14 (1 ,6) | a The data are the average of two replicate tests. It is noted that the N-T compounds, like the compounds of Examples I-XII, are covered by the general disclosure in the above-mentioned United States Patent Nos. 3,442,945 and 3,547,620, but are not included in these specifically indicated in the patent descriptions. Therefore, it would be expected that the type of compounds from the group of compounds disclosed in the mentioned patents Nos. 3,442,945 and 3,547,620 would have generally comparable herbicidal properties. However, a completely unexpected and excellent property of the group of active compounds used in the invention in relation to homologues and a closely related group is additionally demonstrated by comparison with the data for N-T compounds in Table 14. And in this case it should be noted that N- T (like other compounds related to the prior art, as shown especially in Tables 4-8) had low safety factors for sugar beets, as demonstrated by the low GR15 dose values. Moreover, none of the compounds from the group included in Table 14 showed selective control of black oats in sugar beets. It should also be noted that compound P was non-selective for any weed in the study and similarly, compounds N, O, Q and R were completely non-selective and/or marginally selective for all weeds in the study. Of the compounds in Table 14, only compounds S and T caused selective destruction of the common weed, the common red foxtail, the common foxtail and the foxtail. However, also in this case it was shown that sugar beet's too low tolerance of S and T compounds, combined with non-selectivity towards black oats and limited selectivity towards other weeds, makes these compounds completely unacceptable as a herbicide for beets. sugar. In addition, it should be noted (taking into account Tables 4-8) that the active compounds used in the product according to the invention have safety indices for sugar beets and selectivity indices for the above weeds that are overwhelmingly higher than the S and T compounds. Therefore, it should be assessed with the above detailed description, that the active compounds used in the product according to the invention have proven unexpected and significantly better herbicidal properties, both absolutely and in relation to the compounds most similar in terms of structure, other related homologues and analogues including industrial prior art 2-haloacetanilides. More specifically, the active compounds used in the composition according to the invention show unexpected and better safety factors for the cultivation of sugar beets and selectivity, especially in relation to a group of weeds that are difficult to destroy, such as black oats, field foxtail and roof brome, and other difficult for the control of weeds such as trichinopsis, common weed, red fingerling, annual rye, etc., as shown in tables 2-10. The herbicide according to the invention may be in the form of concentrates requiring dilution before use; these concentrates contain at least one active ingredient and an auxiliary agent in liquid or solid form. Herbicides are prepared by mixing the active ingredient with an excipient including diluents, fillers, carriers and conditioning agents to obtain compositions in the form of finely divided solid particles, granules, pellets, solutions, suspensions or emulsions. In this way, the active ingredient may be used with an auxiliary agent such as a finely divided solid, an organic liquid, water, a wetting agent, a dispersing agent, an emulsifying agent, or any suitable combination thereof. The agent according to the invention, especially in the form of liquids and hygroscopic powders, preferably contains as conditioning agents for one solder several surfactants in an amount sufficient to give the given agent the property of easy dispersion in water or oil. Introduction of a surfactant into the agents herbicides significantly increase their effectiveness. By the term "surfactant" it is intended to include wetting agents, dispersants, suspending agents and emulsifying agents. Anionic, cationic and non-ionic surfactants may be used with equal ease. Preferred wetting agents are sulfonates. alkylbenzene and alkylnaphthalene, alkyl fatty acid sulfates, amines or acid amides, sodium isothionate esters of long-chain aliphatic acids, fatty acid esters sulfates or sulfonates, sulfonation products in petroleum refining, sulfonated vegetable oils, di-tertiary, acetylene glycols, derivatives polyoxyethylene alkylphenols (especially isooctylphenol and nonylphenol) and polyoxyethylene derivatives of monoesters of higher fatty acids with hexitol anhydrides (e.g. sorbitan). Preferred dispersants are: methylcellulose, polyvinyl alcohol, sodium lignosulfonates, polymeric alkylnaphthalene sulfonates, sodium naphthalene sulfonate and polymethylene dinaphthalene sulfonate. Hygroscopic powders are water-dispersible compositions containing one or more active ingredients, an inert solid filler and one or more wetting and dispersing agents. Neutral solid fillers are usually of mineral origin. such as natural clay, diatomaceous earth and synthetic inorganic compounds derived from silicon dioxide and the like. Examples of such fillers include kaolinites, hydrated magnesium aluminum silicate and synthetic magnesium silicate. The hygroscopic powder composition of this invention typically contains from about 0.5 to 60 parts (preferably 5-20 parts) of the active ingredient, from about 0.25 to 25 parts (preferably 1-15 parts) of a wetting agent, from about 0.25 to 25 parts (preferably 1.0-15 parts) of a dispersant and from 5 to about 95 parts (preferably 5-50 parts) ) inert solid filler, all parts being by weight relative to the total assembly. If necessary, about 0.1 to 2.0 parts of the inert solid filler may be replaced by the corrosion inhibitor, the antifoaming agent, or both. Other formulations include dust concentrates containing from 0.1 to 60% by weight of the active ingredient in a suitable form. filler; Concentrates of these powders may be diluted for use in concentrations in the range of about 0.1-10% by weight. Aqueous suspensions or emulsions may be prepared by mixing an aqueous mixture of the water-insoluble active ingredient and the emulsifying agent until obtaining homogeneity and then homogenization to establish a stable emulsion of very finely ground particles. The obtained water suspension concentrate is characterized by an extremely small particle size, so that after dilution and spraying, the coverage is very even. Suitable concentrations in these formulations contain about 0.1-60%, preferably 5-50% by weight of the active ingredient, the upper limit being the solubility limit of the active ingredient in the solvent. In another embodiment of aqueous suspensions, the water-immiscible herbicide is an encapsulated formulation forming a microencapsulated phase dispersed in the aqueous phase. In one embodiment, very small *° capsules are formed by combining an aqueous phase containing as an emulsifier lignosulfonate, a water-immiscible chemical compound of polymethylene and polyphenyl isocyanates, and then dispersing the water-immiscible phase in the aqueous phase by adding a multifunctional amine. Isocyanate and amine compounds react to form a solid carbamide coating wall around the particles of a chemical compound that is immiscible with water, thus forming microcapsules. Generally, the concentration of the microencapsulated substance ranges from about 430 to 700 g/l of the total composition, preferably 430-600 g/l. Concentrates are usually solutions of the active ingredient in solvents immiscible with water or partially immiscible with water. , together with a surfactant. Suitable solvents for the active ingredient of this invention include dimethylformamide, methyl sulfoxide, N-methylpyrrolidone, hydrocarbons and water-immiscible ethers, esters and ketones. However, other high concentration liquid concentrates can be prepared by dissolving the active ingredient in a solvent and then diluting it with, for example, kerosene, to the appropriate spray concentration. Concentrated forms of the herbicide according to the invention in they generally contain from about 0.1 to 95 parts (preferably 5-60 parts) of the active ingredient, about 0.25 to 50 parts (preferably 1-25 parts) of the surfactant and, depending on the needs, about 4 to 94 parts of the solvent, with where all parts are by weight relative to the total weight of the emulsifying oil. 55 Granules are physically solid, discrete particle assemblies containing the active ingredient adhering to the filler, the primary inert ingredient finely divided and composed of discrete particles. In order to facilitate leaching of the active ingredient from the individual particles, a surfactant such as that mentioned above may be present in the herbicidal composition. Examples of suitable classes of mineral fillers composed of discrete particles include: natural clays, pyrophyllites, illite and vermiculite. Preferred fillers are porous, absorbent molded particles such as formed and screened sttapulgite or annealed crushed vermiculite and finely divided clays such as kaolin clay, hydrated sttapulgite or bentonite clay. These fillers are sprayed or mixed with the active ingredient to form herbicidal granules. Granular preparations of the agent according to the invention may contain from about 0.1 to about 30 parts, preferably from about 3 to 20 parts by weight of the active ingredient, per 100 parts by weight. clay and 0 to about 5 parts by weight of surfactant per 100 parts by weight of crushed clay. The herbicide according to the invention optionally also contains other supplementary additives, for example natural fertilizers, other herbicides, pesticides, safety agents and the like, used as adjuvants or used in combination with any of the aforesaid adjuvants. Useful chemical compounds in combination with the active ingredients used according to the invention include, for example, triazines, carbamides, carbamates, acetamides, acetanilides, uracils, derivatives of acetic acid or phenol, thiocarbamates, triazoles, benzoic acids, nitriles , diphenyl ethers and others, such as: heterocyclic nitrogen/sulfur derivatives: 2-chloro-4-ethylamino-6-isopropylamino-s-triazine; 2-chloro-4,6-di(isopropylamino)-s-triazine; 2-chloro-4,6-di-(ethylamino)-s-triazine; 6-isopropyl-1H-2,1,3-(3H)-benzothiadiazine-4-2,2-dioxide; 3-amino-1,2,4-triazole; 6,7-dihydrogen-dipyrido-(l,2-a: 2',l'-c)dipyrazinium salt; 5-bromo-3-isopropyl-6-methyluracil; 1,1'-dimethyl-4, 4'-diplridinium salt, carbamides: N'-(4-chlorophenoxy)-phenyl-N,N-dimethylurea; N,N-dimethyl-N'-(3-chloro-4-methylphenyl)-urea; 3-(3,4-dichlorophenyl)-1,1-dimethylurea; 1,3-di-methyl-3-(2-benzothiazolyl)-urea; 3-(p-chlorophenyl)-1,1-dimethylurea; " 1-butyl-3-(3,4-di-chlorophenylH-methylurea, carbamates/thiocarbamates: 2-chloroallyl dimethyldithiocarbamate; s-(4-chlorobenzyl)-N,N-diethylthiocarbamate; N-(3) isopropyl -chlorophenyl)-carbamate; 8-2j3-dichloroallyl-N,N-diisorpopyl-thiocarbamate; N,N - ethyl dipropylthiocarbamate; Stropyl-dipropylthiocarbamate, acetamides/acetanilides (anilines) arnides: 2-chloro-N ,N-dialylacetamide; N,N-dimethyl-2,2-diphenyl-aeetamide; N-(2,4-dimethyl)-5-[(trifluoromethyl)-sulfonylaminophenyl]-acetamide; N-isopropyl-2-echloroacetanilide ; 2',6'-diethyl-N-methoxymethyl-2-chloroacetanilide; a^-trifluoro-2,6 - dinitro-N,N-dipropyl-p-toluidine; N-(l,l - dimethylpropynyl )-3,5-dichlorobenzamide, acids/esters/alcohols: 2,2-dichloropropic acid; 2-methyl-4-chlorophenoxyacetic acid; 2,4-dichlorophenoxyacetic acid; 2-methyl[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- < 10 ll 15-naphthylphthalamidic acid; 5-[2-chloro-4-(trifluoromethyl)-phenoxy]-2-n:sodium trobenzoate; 4,6-dinitro-o-second-butylphenol; N-(phosphonomethyl)glycine and its monoalkyl amines with 1-6 carbon atoms and alkali metal salts and their combinations. Ethers: 2,4-dichlorophenyl-4-nitrophenyl ether; 2-chloro-c*,a,a - trifluoro-p-tolyl-3-ethoxy-4-nitro-biphenyl ether, and others such as: 2,6-dichloro-benzonitrile; monosodium acid methanearsonate; disodium methanearsonate. Mineral fertilizers useful in combination with active ingredients include, for example, ammonium nitrate, urea, potassium carbonate and superphosphate. Other useful additives include materials in which plants take root and develop, such as compost, manure, humus, sand and the like. Herbicide preparations of the types defined above are exemplified in several embodiments. Example XIII. Emulsifiable concentrates. / by weight A. Compound of Example I 50.0 Calcium dodecylbenzenesulfonate/mixed polyoxyethylene glycol ethers (for example Atlox 3437F and Atlox3438F) 5.0 Monochlorobenzene 45.0 B. Compound of Example II Calcium dodecylbenzenesulfonate//mixed polyether alfcilo alcohol - aryl Solvent aromatic hydrocarbons - 9 carbon atoms 100.00 85.0 4.0 11.0 C. Compound of Example XI Calcium dodecylbenzenesulfonate / mixed polyoxyethylene glycol ethers (for example Atlox 3437F) Liquid concentrates.A. Compound from Example I Xylene 100.00 5.0 1.0 94.0 100.00 10.0 90.0 B. Compound from Example II Methyl sulfoxide C. Compound from Example XI Nnmethylpdrolidom 100.00 85.0 15.0 100.00 50.0 50.0 D. Compound from Example Emulsions.A. Compound from Example III Polyoxyethylene/polyoxypropylene block copolymer with butanol 40.0 (e.g. Tergitol XII) Water B. Compound from Example IV Polyoxyethylene/polyoxypropylene block copolymer with butanol Water Example XVI. Hygroscopic powders.A. Compound of Example V Sodium lignosulfonate Sodium N-methyl-N-oleyl taurate Amorphous silica (synthetic) B. Compound of Example VI Sodium dioctylsulfosuccinate Calcium lignosulfonate Amorphous silica (synthetic) C. Compound of Example VII Sodium lignosulfonate N-methyl N -sodium oleyl taurate Kaolin clay Example XVII. Dusting powders.A. The compound of Example I Attapulgite B. The compound of Example VIII Montmorillonite C. The compound of Example IX Bentonite D. The compound of Example XII diatomaceous earth Example XVII. Granules.A. Compound of Example I Granulated attapulgite (20/40 mesh) B. Compound of Example XI Diatomaceous earth (20/40) C. Compound of Example X Bentonite (20/40) D. Compound of Example ni Pyrophyllite (20/40) 4 ,0 56.0 Ibo,óo 5.0 3.5 91.5 100.00 25.0 3.0 1.0 71.0 100.00 80.0 1.25 2.75 16.00 10fiQ 10, 0 3.0 1.0 86.0 100.00 2.0 98.0 100.00 60.0 40.0 100.00 30.0 70.0 100.00 1.0 99.0 100.00 15 ,0 85.0 100.00 30.0 70.0 100.00 0.5 99.5 100.00 5.0 95.0 10 15 20 60 Example XVIII. Microcapsules.A. Compound of Example I encapsulated in a polyurea coating wall 49.0 Sodium lignosulfonate (e.g. Reax 380B) 0.9 Water 49.9 Compound of Example XII encapsulated in a polyurea coating wall Potassium lignosulfonate (e.g. Reax 100.00 10.0 C-21) Water Compound from Example .00 100.00 The herbicide according to the invention containing effective amounts of acetanilides of the given general formula is applied to the soil containing plants or introduced into aquatic environments in any convenient way. The application of a set of ingredients in the form of liquids or crushed solid particles to the soil can be carried out using typical methods, for example using mechanical dusters, mechanical or manual sprayers and dusting atomizers. The herbicide can also be applied from airplanes, in the form of dust or spray, due to its effectiveness at low dosages. The application of herbicides to aquatic plants is usually carried out by adding these herbicides to aquatic media on surfaces where destruction of aquatic plants is required. The use of an effective amount of active compounds of the given general formula to the location of occurrence of undesirable weeds is intended to significant importance in the practice of using the agent according to the present invention. The exact amount of active ingredient that should be used depends on various factors including the plant species and stage of development, soil type and conditions, amount of rainfall and the specific acetanilide used. In selective pre-emergence application to plants or soil, the dosage is usually from 0.02 to about 11.2 kg/ha, preferably from about 0.04 to about 5.60 kg/ha or from 1.12 to 5, respectively. 6 kg/ha. Lower or higher doses may be required in some cases. One skilled in the art can easily use this description, taken together with the above examples, to determine the optimal index to use in any particular case. The term "soil" is used in its broad sense, including all typical "soils" as defined in Webster's New International Di*123 885 40 tionary, second edition, unabridged (19G1). The term therefore refers to any substance or medium in which vegetation can take root and develop and includes not only soil but also compost, organic manure, peat, humus, sand and the like, adapted to support development of the plant. Although the invention is described with reference to specific varieties, the details thereof are not to be construed as being limited solely to the scope indicated in the following claims. The claims of the patent include: 1. A herbicide containing the active substance and conventional auxiliaries, characterized in that that as an active substance it contains at least one compound of the given general formula, in which R denotes an ethyl, n-propyl, isopropyl, isobutyl, allyl or butenyl group, Ri denotes a methyl, n-propyl, isopropyl, n -butyl, isobutyl or isoamyl and Rt represents a methyl, ethyl or isopropyl group; wherein when R* is an isopropyl group, then R is an ethyl group and Ri is an n-butyl group; when Ri is an ethyl group, then R is an ethyl, n-propyl, or allyl group and Rt is an n-butyl group or isobutyl, when R is an n-propyl group, then Ri is an isobutyl group, when R is an isopropyl group, then Ri is an isobutyl group, when R is an n-propyl or isopropyl group, then Ri is an isobutyl group When R is an isobutyl group, then Ri is an n-propyl, isopropyl, isobutyl or isoamyl group, and when R is a butenyl group, then Ri is a methyl group. 2. The agent according to claim 1, characterized in that the active substance contains a compound of the given general formula, in which R denotes an alkyl group with 2-4 carbon atoms, and Ri denotes an alkyl group with 3 or 4 carbon atoms, and the substituent R8 has the meaning defined in claim 1. 3. The agent according to claim 1. 2, characterized in that it contains N-(n-propoxymethyl)-2'-isobutoxy-6'-methyl-2-chloroacetanilide as the active substance. 4. The agent according to claim 2, characterized in that it contains N-(isopropoxymethyl)-2'-isobutoxy-6'-methyl-2-chloroacetanilide as the active substance. 5. Agent according to claim. 2, characterized in that the active substance contains N-(isobutoxymethyl)-2'-isobutoxy-6'-methyl-2-chioroacetanilide. 6. The agent according to claim 2, characterized in that it contains N-(ethoxymethyl)-2'-isobutoxy-6'-ethyl-2-chloroacetaniide as the active substance. 7. The agent according to claim 1, characterized in that it contains N-(allyloxymethyl)-2'-isobutoxy-6'-ethyl-2-chloroacetanilide as the active substance. 8. The agent according to claim 2, characterized in that it contains N-(ethoxymethyl)-2'-n-butoxy&'-isoropyl-2-chloroacetanilide as the active substance. 9. The agent according to claim 2, characterized in that it contains N-(isobutoxymethyl)-2'-isopropoxy-6'-methyl-2-chloroacetanilide as the active substance. 10. The agent according to claim 2, characterized in that it contains N-(isobutoxymethyl)-2'-n-propoxy-6'-methyl-2-chloroacetanilide as the active substance. 11. The agent according to claim 2, characterized in that it contains N-(n-propoxymethyl)-2'-n-butoxy-6'-ethyl-2-chloroacetanilide as the active substance. 12. The agent according to claim 1, characterized in that it contains N-(allyloxymethyl)-2'-n-butoxy-6'-ethyl-2-chloroacetanilide as the active substance. o CICH2C CR,OR Y PL PL PL PL PL

Claims (12)

1. The claims of the patent are as follows: 1. A herbicide containing an active substance and conventional auxiliaries, characterized in that as an active substance it contains at least one compound of the given general formula, in which R is an ethyl, n-propyl, isopropyl group. , isobutyl, allyl or butenyl, R1 is a methyl, n-propyl, isopropyl, n-butyl, isobutyl or isoamyl group and Rt is a methyl, ethyl or isopropyl group; wherein when R* is an isopropyl group, then R is an ethyl group and Ri is an n-butyl group; when Ri is an ethyl group, then R is an ethyl, n-propyl, or allyl group and Rt is an n-butyl group or isobutyl, when R is an n-propyl group, then Ri is an isobutyl group, when R is an isopropyl group, then Ri is an isobutyl group, when R is an n-propyl or isopropyl group, then Ri is an isobutyl group When R is an isobutyl group, then Ri is an n-propyl, isopropyl, isobutyl or isoamyl group, and when R is a butenyl group, then Ri is a methyl group. 2. The agent according to claim 1, characterized in that the active substance contains a compound of the given general formula, in which R denotes an alkyl group with 2-4 carbon atoms, and Ri denotes an alkyl group with 3 or 4 carbon atoms, and the substituent R8 has the meaning defined in claim 1. 3. The agent according to claim 2, characterized in that it contains N-(n-propoxy-methyl)-2'-isobutoxy-6'-methyl-2-chloroacetanilide as the active substance. 4. The agent according to claim 2, characterized in that it contains N-(isopropoxymethyl)-2'-isobutoxy-6'-methyl-2-chloroacetanilide as the active substance. 5. Agent according to claim. 2, characterized in that the active substance contains N-(isobutoxymethyl)-2'-isobutoxy-6'-methyl-2-chioroacetanilide. 6. The agent according to claim 2, characterized in that it contains N-(ethoxymethyl)-2'-isobutoxy-6'-ethyl-2-chloroacetaniide as the active substance. 7. The agent according to claim 1, characterized in that it contains N-(allyloxymethyl)-2'-isobutoxy-6'-ethyl-2-chloroacetanilide as the active substance. 8. The agent according to claim 2, characterized in that it contains N-(ethoxymethyl)-2'-n-butoxy&'-isoropyl-2-chloroacetanilide as the active substance. 9. The agent according to claim 2, characterized in that it contains N-(isobutoxymethyl)-2'-isopropoxy-6'-methyl-2-chloroacetanilide as the active substance. 10. The agent according to claim 2, characterized in that it contains N-(isobutoxymethyl)-2'-n-propoxy-6'-methyl-2-chloroacetanilide as the active substance. 11. The agent according to claim 2, characterized in that it contains N-(n-propoxymethyl)-2'-n-butoxy-6'-ethyl-2-chloroacetanilide as the active substance. 12. The agent according to claim 1, characterized in that it contains N-(allyloxymethyl)-2'-n-butoxy-6'-ethyl-2-chloroacetanilide as the active substance. o CICH2C CR,OR Y PL PL PL PL PL