FI73971C - 2-HALOGENACETANILIDFOERENINGAR SAMT HERBICIDKOMPOSITIONER INNEHAOLLANDE DESAMMA. - Google Patents

Description

1,73971 2-haloacetanilide compounds and herbicidal compositions containing them

The invention relates to 2-haloacetanilide compounds and herbicidal compositions containing them.

Various 2-haloacetanilides have been described in the literature, in which the anilide nitrogen atom or anilide ring may be unsubstituted or substituted by various substituents such as alkyl, alkoxy-13, alkoxyalkyl, halogen radicals.

With respect to the compounds of the invention having an alkoxymethyl radical at the anilide nitrogen, an alkoxy radical at the second ortho position, and a specific alkyl radical at the second ortho position, the closest known techniques are U.S. Patents 3,442,945 and 3,547,620.

The closest compounds in said patents are 2'-tert-butyl-2-chloro-N-methoxymethyl-6'-methoxyacetanilide and its bromine analogue (Examples 18 and 34 in U.S. Patent 3,547,620 and Examples 18 and 36 in U.S. Pat. in Patent 20 3,442,945).

U.S. Patents 4,070,389 and 4,152,137 disclose a general formula that includes the compounds described in the aforementioned U.S. Patents 3,442,945 and 3,547,620. However, the only compound specifically described having an alkyl radical at the second ortho position and an alkoxy radical at the second ortho position has an alkoxyethyl radical at the anilide nitrogen atom; compounds of this type are discussed in more detail below. Less relevant prior art is represented by BE-30 patent 810 763 and DE-A-2 402 983. The compounds disclosed therein are of the same type as those described in the aforementioned U.S. Patents 4,070,389 and 4,152,137 and are characterized by alkoxyalkyl a radical having two or more carbon atoms between the anilide nitrogen atom and the oxygen atom of the alkoxy group. The closest compounds described in said BE patent 2 73971 810 763 and DE application 2402 983 are those having an ethoxyethyl radical at the anilide nitrogen atom, a methoxy or ethoxy radical at one ortho position and a methyl or ethyl radical at the second ortho position. in the ortho position (Compound Nos. 7, 13 and 18 in BE Patent 810763). Other less relevant homologues of these compounds have also been described, e.g., compounds 6,9, 16, and 17 having a methoxyethyl or methoxypropyl radical as substituents on the nitrogen atom and a methoxy or ethoxy radical at one ortho position and a methyl radical at another in the ortho-position.

The aforementioned U.S. Patent 3,442,945 discloses some values for the aforementioned compounds having the closest chemical configuration to the compounds of the invention, and other patents disclose some values for other homologous and analogous compounds that are less closely related. chemical structure, e.g. said compounds 6 and 209 in the above-mentioned Belgian patent 810 763.

Although this closest known technique describes herbicidal activity against various weeds, it does not show any values for compounds that additionally and / or simultaneously control difficult-to-kill perennial weeds, Agrophron repens and Cyperusesculus. a wide range of weeds, including hard-to-destroy annual broadleaf weeds such as 30 Sida Spinos, Sesbania exaltat, Datura stramonium, etc. and annual weeds such as sorghum (Sorghum halepence), Sorghum bicolor, Broa (Alexair) Weeds of the genus Panicum (Texas, autumn and white proso millet), 35 red rice (Oryza Sativa) and scab (Rotthoellia exaltata), while also controlling other harmful perennial and annual weeds, such as bitter buckwheat. -CPolygonum sp.), Powdery mildew (Chenopodicom album) (Amaranthus retroflexus), collar hay (Setaria), blood millet (Digitaria sanguinalis) 5 and chicken millet revono (Enhinochloa crus-Galli).

A very useful and desired property of herbicides is the ability to maintain weed control over a long period of time, with the longer it is the better during each harvest season. With several of the 10 known herbicides, weed control takes only 2 or 3 weeks, or in some excellent cases, perhaps up to 4-5 weeks, before they lose their effective phytotoxic properties. Thus, one disadvantage of most known herbicides is their relatively short shelf life in soil.

Another disadvantage of some known herbicides, which is to some extent related to their shelf life in soil under normal weather conditions, is the loss of their weed control during heavy rainfall, which renders several herbicides ineffective.

The disadvantage of herbicides, which are still often known, is that their use is limited to a certain type of soil, i.e. although certain herbicides are effective in soils containing small amounts of organic matter, they are ineffective in other soils containing a lot of organic matter, or vice versa. It is therefore preferred that the herbicide can be applied to all types of soils ranging from light organic soils to strong clay and humus-rich soils.

A further disadvantage of many known herbicides is their limitation to a certain type of use, i. either for surface application before germination or for mixing with soil. It is highly desirable that the herbicide can be applied in any form of application, either by surface application or by mixing with soil.

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And finally, the disadvantage of certain herbicides is the need to apply and maintain special treatment methods due to their toxic nature. Thus, it is advantageous if the herbicide can be safely handled.

Accordingly, it was an object of the present invention to provide a group of herbicidal compounds which do not have the above-mentioned disadvantages of known herbicides and which have a number of advantages which the individual herbicidal groups have not previously had.

The object of the invention is to provide herbicides which control perennial and annual weeds which are difficult to destroy, such as Juola wheat, yellow nutcracker, sorghum, Sida spinos, S. esbania exaltat, Sorghun bicolor alexander, Panicum grasses, red rice and scabies, as well as a wide range of other harmful weeds, such as bitter buckwheat, flour, clay, mad grass, collar grass, 20 chicken millet and blood millet, and which are also better able to affect resistant weeds such as (Ipomoea sp.) And paw grass (Xanthium pensylvanicum), which maintain crop safety for a variety of useful crops such as soybeans, cotton, peanuts, oilseed rape and / or shrub beans.

It was a further object of the invention to provide a herbicidal effect on the soil for a period of up to 18 weeks 30.

It was a further object of the invention to provide herbicides which are resistant to soil leaching and dilution caused by very humid conditions, e.g. heavy rains.

It was also an object of the invention to provide herbicides which are effective in various soils, e.g. light organic soils, heavy clay and humus-rich soils. The advantage of the herbicides according to the invention is e.g. their mode of application, i.e. surface treatment before germination and mixing with soil.

The herbicides according to the invention also have the advantage that they are safe and do not require any special treatment.

The invention relates to herbicidal compositions containing herbicidally active compounds as active ingredients.

It has been found that a certain group of 2-haloacetanilides characterized by specific hydrocarbyloxymethyl radicals at the anilide nitrogen atom, specific alkoxy radicals at the second ortho position and hydrogen or a methyl or ethyl radical at the second ortho position, and surprisingly improved excellent herbicidal properties compared to known herbicides, including the closest homologous compounds of the prior art.

The most important feature of the herbicidal compositions according to the invention is their ability to control a wide range of weeds, including weeds controlled by known herbicides and in addition a number of weeds which individually and / or together have so far not been controlled by one class of known herbicides while maintaining crop safety. or more useful plants including especially soybean, wood-30 wool, peanut, oilseed rape and folding bean among others. While known herbicides are useful in controlling a variety of weeds, including in some cases certain resistant weeds, the herbicides of the invention have been found to be able to control or strongly reduce a large number of resistant perennial and annual perennial weeds, such as perennial herbaceous weeds. weeds such as sida spinosa, Sesbania exaltata, mad grass (Datura stramonium), bitter buckwheat, flour clay, 5 clayey and annual grasses such as sorghum (Sorghum bicolo ;, alexander grass, johnson grass, Texahirs), white prosa ), red rice, scabies, and other harmful weeds such as autumn millet, setaria, chicken-10 millet, and blood millet.The improved weed reduction has also been achieved by combining resistant weeds such as wool, velvet leaf, day-old and bile weed. Essa.

The compounds of the invention have the formula wherein R is ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl; R 1 is methyl, ethyl, n-propyl or isopropyl and R 2 is hydrogen, methyl or ethyl; with the proviso that when R 2 is hydrogen, then R 1 is ethyl and R is allyl; when R 2 is ethyl, then R 1 is methyl and R is isopropyl; when R 1 is methyl, then R is ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl; when R 1 is ethyl, then R is sec-butyl, allyl or propargyl; when R 1 is n-propyl then R is ethyl, and when R 2 is isopropyl then R is ethyl or n-propyl.

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A preferred compound of the invention is 2'-methoxy-6'-methyl-N- (isopropoxymethyl) -2-chloroacetanilide.

Other compounds of the invention include: 2'-methoxy-61-methyl-N- (ethoxymethyl) -2-chloroacetanilide, 2-netoxy-D * -methyl-N- (1-sec-butoxymethyl) ) -2-chloroacetanilide, 2'-ethoxy-6'-methyl-N- (allyloxymethyl) -2-chloroacetanilide, 2'-ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide, 2 '-ethoxy-N- (allyloxymethyl) -2-chloroacetanil-15 di, 2H-methoxy-6'-ethyl-N- (isopropoxymethyl) -2-chloroacetanilide, 2'-ethoxy-61- methyl N- (1-methylpropoxymethyl) -2-chloroacetanilide, 2'-n-propoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide, 2'-isopropoxy-6'-methyl -N- (ethoxymethyl) -2-chloroacetanilide and 2'-isopropoxy-6'-methyl-N- (n-propoxymethyl) -2-25 chloroacetanilide.

The invention also relates to herbicidal compositions which contain as active ingredient one or more 2-haloacetanilide compounds of the formula I.

The compounds of the invention may be prepared in a variety of ways. For example, these compounds can be prepared by the azomethine method described in the aforementioned U.S. Patents 3,442,945 and 3,547,620. According to the azomethine method, the appropriate primary aniline is reacted with formaldehyde to form the corresponding methyleneaniline (substituted phenylazomethine) 8,73971, which is then reacted with a haloacetylating agent such as chloroacetyl chloride or chloroacetyl anhydride, and the resulting compound is reacted with a suitable alcohol to give the corresponding 5-N-alkoxymethyl-2-chloroacetanilide as a final product.

Another method described in detail below involves transesterification of the appropriate N-methylene ether-2-haloacetanilide with the desired alcohol to give the corresponding trans-etherified N-hydrocarbylmethyl-2-haloacetanilide.

In another process for preparing the compounds of the invention, the anion of a suitable secondary 2-haloacetanilide is N-alkylated with an alkylating agent under basic conditions. The N-alkylation process is described in detail in Examples 11-14.

Example 1 This example illustrates the preparation of 2'-methoxy-6'-methyl-N- (isopropoxymethyl) -2-chloroacetanilide in one preferred compound.

2'-Methoxy-6'-methyl-N- (methoxymethyl) -2-chloroacetanilide (0.025 moles) in 100-150 ml of isopropanol containing about 0.02 moles of methane-25-sulfonic acid was heated to reflux in a Soxhlet extractor containing activated 3A molecular sieves (25 g) to absorb the released methanol. The reaction was monitored by glc. After completion of the reaction, the excess alcohol was removed in vacuo and the residue was taken up in ether or chloroform.

The solution was washed with 5% sodium carbonate solution, dried (MgSO 4) and evaporated. The product was purified by ball distillation. 55% was obtained; a light amber substance, m.p. 40-41 ° C.

9,73971

Anal: Calculated for R 2 H 2 ClNO 2 (%): C, 58.84; H, 7.05; N, 4.90; Cl, 12.41.

Found: C, 58.55; H, 7.08; N, 4.89; Cl, 21.45. This product was identified as described in the introduction to this example.

Examples 2-9

Following essentially the same procedures, amounts of reaction components, and general conditions as described in Example 1, but using another suitable alcohol to effect trans-etherification, other N-hydrocarbyloxy-ethyl-2-haloacetanilides identified in Table I were prepared.

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Example 10 This example illustrates the preparation of N- (methoxymethyl) -tert-anilide starting materials used to prepare the final products described in Examples 1-9.

The N-methylene ether-substituted-2-chloroacetanilide starting materials used in Examples 1-9 were prepared by alkylation of the appropriate secondary 2-haloacetanilide by the n-alkylation method described above.

This procedure is described in this example except for the preparation of the starting material described in Example 1.

2'-Methoxy-6'-methyl-2-chloroacetanil-15 di (0.025 mol), bromomethyl methyl ether (0.05 mol) and benzyltriethylammonium bromide (2 g) were dissolved in methylene chloride (70 ml).

Sodium hydroxide solution (HO ml; 50%) was then added portionwise with stirring and maintaining the temperature under cooling at 20-25 ° C. After the addition was complete, the mixture was stirred for an additional 1.5 hours. Water (100 ml) was then added while cooling and the layers were separated. The methylene chloride layer was washed twice with 30 ml of saturated sodium chloride solution, dried (O 2 SO 4) and evaporated. The remaining product was crystallized or distilled in vacuo to give a yellow liquid, b.p. 1H0 ° C at 1.2 mm Hg.

Anal. Calculated for Ο- ^ ϋ ^ βΟΙΝΟ ^ (%): 30 C, 55.92; H, 6.26; N, 5, HH; Found: C, 56.15; H, 6.33; N, 5 36.

The product was identified as 2'-methoxy-6'-methyl-N- (methoxymethyl) -2-chloroacetanilide.

Similarly, the N-methylene ether-substituted-2-chloroacetanilide starting materials of Examples 2-9 were prepared by alkylation of the corresponding secondary anilide with bromomethyl methyl ether, respectively; analogous chloromethyl and iodomethyl methyl ethers can also be used.

The secondary anilide starting material used in this example to prepare the tertiary N-methoxymethyl compound was prepared by chloroacetylation of the corresponding primary amine as follows: 2-methoxy-6-methylaroline (0.03 mol) in methylene chloride (30 ml). was stirred vigorously with 10% sodium hydroxide solution (0.05 mol) at 1C while a solution of chloroacetyl chloride (0.033 mol) in methylene chloride (20 ml) was added, keeping the temperature at 15-25 ° C under external cooling. The reaction mixture was stirred for a further 30 minutes after the addition was complete, the layers were separated and the methylene chloride layer was washed with water, dried and evaporated in vacuo. The product was crystallized from a suitable solvent to give white needles, m.p. 130-131 ° C.

Anal. Calculated for C 18 H 19 Cl 2 Cl 2 (%): 20 C, 56.21; H, 5.66; N, 6.56; Cl, 16.59 Found: C, 56.16; H, 5.66 N, 6.57; Cl, 16.55. The product was identified as 2'-methoxy-6'-methyl-2-chloroacetanilide.

The secondary anilides used as starting materials in Examples 2-9 were prepared in a similar manner.

The primary amines used to prepare the above-mentioned secondary anilides can be prepared in a manner known per se, e.g. by catalytic reduction of the corresponding substituted nitro-benzene in ethanol using a platinum oxide catalyst.

As indicated above, the products of the invention can also be prepared directly from the secondary anilide using said N-alkylation process without first having to prepare the N-hydrocarbyl-73971 byyloxymethyl intermediate (as described in Example 10) which is then trans-esterified to the final product. as described in Example 1. Examples 11-14 illustrate the preparation of compounds 5 of the invention by said N-alkylation process.

Example 11 2 N-Propoxy-6'-methyl-2-chloroacetanilide (4.35 g), chloromethyl ethyl ether (3.4 g) and benzyltriethylammonium chloride (1.5 g) were mixed in 250 ml of methylene chloride and cooled. .

To the mixture was added 50 mL of 50% NaOH at 15 ° C and stirred for 2 hours, then 100 mL of water was added. The layers were separated, washed with water, dried over MgSO 4 and evaporated. The product was purified by ball distillation to give 4.8 g (289% yield) of a clear liquid, b.p. 130 ° C at a pressure of 0.07 mm

Hg.

Anal. Calculated for C 18 H 22 ClNO 3 (%): C, 60.10; H, 7.40; Cl, 11.83 Found: C, 59.95; H, 7.39; Cl, 11.79.

The product was identified as 2'-N-propoxy-6T-methyl-N- (ethoxymethyl) -2-chloroacetanilide.

Example 12 2'-Isopropoxy-6'-methyl-2-chloroacetanil-25 dia, 5.55 g, 4.4 g of chloromethylethyl ether, 2.5 g of benzyltriethylammonium chloride were stirred in 250 ml of methylene chloride and cooled to 0 ° C. To the mixture was added 50 mL of 50% NaOH in one portion while maintaining the temperature below 15 ° C. The mixture was stirred for 2 hours, cooled and 100 ml of water were added. The layers were separated, washed with water, dried over MgSO 4 and evaporated to give 4.7 g (69% yield) of product as a yellow oil.

Anal. Calculated for? 15 ^ 22 ^ 1 ^ 03 (%): 35 C, 60.10; H, 7.40; N, 4.67; Cl, 11.83; Found: C, 60.10; H, 7.40; N, 4.64; Cl, 11.73.

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The product was identified as 2f-isopropoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide.

Example 13

Substantially following the procedure described in Examples 11 5 and 12, but using chloromethyl propyl ether as the alkylating agent, 5.0 g (88% yield) of a yellow oil were obtained.

Anal. Calculated for C 18 H 18 N 2 O 2 CINO 2 (%): C, 6.24; H, 7.71; N, 4.46; Cl, 11.30.

Found: C, 61.18; H, 7.76; N, 4.43; Cl, 11.31.

The product was identified as 2'-isopropoxy-5-methyl-N- (n-propoxymethyl) -2-chloroacetanilide.

Example 14

Following the procedure described in Examples 11-13, but using the appropriate sec-anilide and halomethyl allyl ether, a yellow oil, b.p. 134 ° C / 0.08 mm Hg (ball tube).

Anal. Calculated for C 18 H 18 ClNO 3 (%): C, 59.26; H, 6.39; N, 6.94; Cl, 12.49.

Found: C, 59.20; H, 6.41; N, 6.95; Cl, 12.52.

The product was identified as 2'-ethoxy-N- (allyloxymethyl) -2-chloroacetanilide.

The herbicides according to the invention have been found to have unexpectedly good properties as pre-emergence herbicides, in particular for the selective control of perennial and annual weeds which are difficult to destroy, such as perennial ryegrass and yellow walnut, annual broadleaf weeds, crazy grass (Datura stramonium), bitter buckwheat, flour clay, clay and annual grasses such as sorghum (Sorghum bicoloa), Alexander grass, johnson grass, Texas millet, white proso millet (Panicum texanum), red rice, scabies, scabies 35 Setaria), chicken millet and large blood millet. An improved reduction in the weed population of 16,73971 has also been achieved with resistant weeds such as wool, velvet leaf, sunflower and paw grass.

The selective control and improved eradication of the above-mentioned weeds using the herbicides of the invention have been found in the crop of various useful plants including soybean, cotton, peanut, oilseed rape and folding beans. Selectivity has been shown in experiments on sugar beet, maize, sweetcorn, wheat, barley and sorghum; however, these crops generally tolerate less of the herbicides of the invention than the aforementioned crops. It will be appreciated in this art that not all of the aforementioned weeds are selectively controllable by all compounds of the invention under all conditions of climatic, soil, moisture and / or herbicidal application.

To illustrate the good properties of the unexpected towers of the compounds of the invention, both in absolute and relative terms, comparative experiments were performed in the greenhouse and in the field using: (1) known compounds closest in chemical structure to compounds of the invention, (2) other known homologues with excellent herbicidal activity. properties, and (3) commercial herbicidal compounds that are chemically comparable to the compounds of the invention. All compounds in the control experiments were defined as substituted phenyl-N-alkoxyalkyl-2-haloacetanilides. The known reference compounds shown in the tables are identified as follows: 17,73971 A. 21-Methoxy-6 * -tert-butyl-N- (methoxymethyl-2-chloroacetanilide; (Example 18 in U.S. Patents 3,442,945 and 3,547,620).

B. 2'-methoxy-6'-Pert-butyl-N- (methoxymethyl-5'-yl) -2-bromoacetanilide; (Example 34 in U.S. Patent 3,547,620 and Example 3b in U.S. Patent 3,442,945).

C. 2 ', 6'-diethyl-N- (methoxymethyl) -2-chloroacetanilide; (Example 5 in U.S. Patents 3,547,620 and 3,442,945, this compound has the generic name 10 "alachlcr" and is the active ingredient in the commercial £ herbicide LASSO, a registered trademark,

Monsanto Company).

D. 2'-methyl-6'-ethyl-N- (ethoxymethyl) -2-chloroacetanilide; (Example 53 in U.S. Patent 3,547, 15,620; generic "Acetochlor").

E. 2 ', 6'-dimethyl-N- (isopropoxymethyl) -2-chloroacetanilide; (Example 31 in U.S. Patent 3,547,620 and Example 33 in U.S. Patent 3,442,945).

F. 2'-methoxy-6'-methyl-N- (methoxyethyl) -2-20 chloroacetanilide; (Compound No. 6 in Belgian Patent 810,763).

G. 2'-methoxy-6'-methyl-N- (ethoxyethyl) -2-chloroacetanilide; (Compound No. 7 in Belgian Patent No. 810,763).

H. 2'-methoxy-6'-methyl-N- (1-methoxyprop-2-yl) -2-chloroacetanilide; (Compound No. 9 in Belgian Patent 810,763) and I. 2'-methyl-6'-ethyl-N- (1-methoxyprop-2-yl) -2-chloroacetanilide; (U.S. Patent No. 3,937,730; generic "metolachlor"; this compound is active

R

ingredient in the commercial herbicide "Dual, registered trademark, Ciba-Geigy Corporation).

In the pre-emergence herbicidal experiments, the compounds according to the invention were compared with the known compounds A1 with regard to the control of various perennial and annual weeds, in particular difficult-to-eradicate species which, when widespread, cause damage to important crops such as soybeans peanut, canola and shrub beans. The results are shown below.

Regarding the values given in the tables, the amount of herbicide used is denoted by "GR- ^ g" and "GRgg", which are expressed in kilograms per 10 hectares, GR ^ g indicates the maximum amount of herbicide required to produce a crop damage of 15% or less , and GRgg is the minimum amount required to achieve weed control of 8 to 5% GR-^ g and 15 GRgg are used as a measure of potential commercial efficacy, however, it should be understood that suitable commercial herbicides may have a greater or lesser harmful effect on plants. within reasonable limits.

20 As a measure of the effectiveness of a chemical as a selective herbicide, the "selectivity factor" ("SF") is given in relation to the herb given to the herbicide and the weeds given. The selectivity * · coefficient is a measure of the certainty of the crop and is expressed as the ratio GR ^ g / GRgg, i.e. the GR ^ g value of the crop divided by the GRgg value of the weed, both values being expressed in pounds / acre. In the following tables, the selectivity coefficients are shown in parentheses; the symbol "NS" means "non-selectivity"; a margin of 30 or indeterminate selectivity is indicated by a dash (-) and a blank indicates that the plant species in question has not been subjected to a specific experiment, that a value has not been obtained for some reason, or that it is less relevant than other values obtained, e.g. certain short-term findings were omitted in favor of long-term observations, or long-term observations were omitted because short-term findings clearly showed some herbicidal activity.

5 Since crop tolerance and weed control are interrelated, it is appropriate to describe this relationship using a selectivity factor. In general, it is desirable for crop tolerance values to be high because high lightness herbicides are often used for one reason or another. On the other hand, it is desirable that the control amounts of sulfur grass be small, i.e. they have a high unit activity for both economic and possibly ecological reasons. However, small amounts of herbicide 15 may not be sufficient to control certain weeds, in which case a larger amount is required. Thus, the best herbicides are those that control the largest possible number of weeds with the smallest possible amount of Herbi-20 binder and provide crop security, i. the highest possible degree of crop tolerance. Thus, “selectivity factors” (defined above) are used to indicate the relationship between crop security and weed control, and the reference to the selectivity factors in the table indicates that the higher the numerical value, the higher the herbicide selectivity for the weed control crop.

Preemergence tests 30 include both in a greenhouse and a field experiment. i.e. the herbicide is applied to the soil surface, then mixed with it and then the seeds of the useful plant are planted.

The surface application method 5 used in the greenhouse is carried out as follows: containers, e.g. aluminum pans usually measuring 24, 13 cm x 13, 34 cm x 6.99 cm or plastic containers measuring 9.53 cm x 9.53 cm x 7.62 cm with running holes in the bottom, filled with Ray sanding clay and then sealed to a height of 10 1.27 cm from the top of the containers. The pots are then seeded with the test plant species, then covered with a 12.7 mm layer of test soil. The herbicide is then applied to the soil surface with a belt sprayer at a rate of 187 l / ha, 2.11 15 kg / cm 2; other spray equipment, eg DeVilbis sprayer can also be used. Each tank receives 0.64 cm of water as a surface spray and then the containers are placed in greenhouse benches for subsequent irrigation if necessary. In the alternative method, surface irrigation can be omitted.

Observations of herbicidal effects are made 3 weeks after treatment.

The herbicide treatment by mixing with soil is carried out in greenhouse experiments as follows: 25 Good quality topsoil is placed in aluminum pans and compacted to a depth of 9.5-12.7 mm from the top of the pan. Seeds or spores of different plant species are placed on the ground. The soil needed to fill the pans for insemination or after the addition of plant-30 shoots is weighed into the pan. The soil and a certain amount of active ingredient in a solvent or wettable powder suspension are mixed well and used to cover the prepared pans. After treatment, the pans are irrigated with water corresponding to 0.64 cm of rain, after which 2i 73971 is irrigated, if necessary, to obtain sufficient moisture for germination and growth. In an alternative method, surface irrigation can be omitted. Observations are made approximately 3 weeks after insemination and conception.

In the first set of experiments, the pre-emergence herbicidal activity is shown in Table II and compares the relative efficacy of the compounds of the invention compared to the relevant 10 known compounds against yellow nut and common wheat in soybean, cotton and maize crops.

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The values shown in Table II show that, in general, the compounds of the invention are significantly more active as a class, i. they have higher unit activity against both yellow walnut and 5 jow wheat and have higher yield safety for soybeans and cotton than the reference compounds.

In particular, as regards the control of the yellow nut, it should be noted that each of the compounds of the invention tested was significantly more active against the yellow nut than compounds A and B, which are the closest reference compounds in structure, and H, although not as close as A and B, it can be considered to be in many respects closer to the compounds according to the invention than compounds C, D, E and I. In particular, the compound of Example 1 with a GRgg of 0.1 kg / ha was approximately twice as high. both active and the most active 20 reference compound E (GRgg value = 0.17), and its yield safety factor was 3 times that of compound E in soybeans and the same certainty in cotton. It should also be noted that the compounds of the invention according to Examples 2 and 12 also had the same 25 and correspondingly higher unit activity than compound E against the yellow nutcracker. In addition, although Compounds F and G had very high unit activity, neither compound was selective against yellow walnut in soybeans and Compound F was not selective in cotton. Although Compound G selectively controlled the nut nut in cotton, it had a lower degree of safety than all compounds of the invention except the compound of Example 2 and significantly less than the compounds of Examples 5, 6 and 13. The selectivity coefficients of the compounds of Examples 9 and 14 against the nut nut in soybean were particularly good.

As for the control of downy wheat, the compound of Example 5 of Example 5 was almost three times more active than the most active control compound D at the same time as its yield was equally good in soybeans. The compound of Example 3 also had a higher unit activity against common wheat and 3 times the certainty in soybeans than Compound E. It should further be noted that each compound of the invention tested had significantly better unit activity against common wheat than Compounds A and B, which are the closest reference compounds. Although the unit activity of Compound H against locust bean was slightly higher than that of the compounds of Examples 9 and 14, the selectivity coefficients of the latter compounds against locust bean in soybean were about 2-fold higher than that of Compound H, the next closest reference compound. In addition, compounds A, B, F, and G were not selective against jow wheat in soybeans.

Furthermore, from the value in Table II, it can be seen that of all the compounds tested, the compounds of Examples 5, 6, 9 and 14 had by far the best safety factors in soybeans against both yellow walnut and downy wheat. The compounds of Examples 5, 6 and 13 had much higher safety factors of 30 m in cotton against yellow fever. It should further be noted that the excellent yield coefficients of the compounds of Examples 5, 6, 9, 13 and 14 are associated with very low GRg values, indicating high unit activity against yellow nut and jet wheat. In these experiments, most of the compounds of the invention were non-selective in maize as well as 66,73971 as all but three of the reference compounds. However, the compound of Example 14 had significantly better selectivity for both Juola wheat and yellow walnut in maize.

In other comparative experiments, the herbicidal activities of the reference compounds C and D and the compound of Example 1 before germination against various annual broadleaf weeds at a rate of 3.36 kg / ha were examined. Observations were made 6-7 weeks after 10 weeks of treatment (WAT) and a percentage of weed control was determined; the values of these experiments are shown in Table III.

Table III

Control of annual broadleaf weeds 15 Before germination 6-7 WAT__

Weed _Compound_

Example 1 C D

Sida spinosa 93 35 73

Sesbania exaltata 100 0 59 20 Item 83 62 88

Bitter buckwheat 88 64 76

Flour whey 75 61 81

Wool 72 53 43

Mad Grass 98 68 98 25 The values in Table III show that the compound of Example 1 had significantly better activity than Compound C against each one-year broad-leaved weed. Similarly, the compound of Example 1 had significantly better activity compared to Compound D against Sida spinosa, Sesbania exaltata, bitter buckwheat and wool, while having equal activity against mad grass and somewhat lower unit activity against clay and flour clay.

27 7 3 9 71

In the following comparative experiments, field experiments were performed to determine the herbicidal activities and crop selectivities of the compound of Example 1 and Reference Compounds C, D, E and I before 5 budding against chicken millet, Sida spinosa and Sesbania exaltata in soybeans. These experiments were performed in separate clay soil (Sharkey) containers containing 2.0% organic matter and treated with different concentrations of each herbicide 10 as an emulsifiable concentrate at 280.5 kg / ha. Observations were made 4 and 7 weeks after treatment. The experiments were repeated 3 times and the experimental values showed that after 7 weeks the only compound that selectively controlled Sesbania exaltata was the compound of Example 1; such a control (GRg, -) was achieved only at 1.6 kg / ha, while for compounds C, E and I the GRgg value was 5.6 kg / ha and for compound D 5.0 kg / ha. The GR15 value in the soybean was 3.9 kg / ha, indicating a 2.0-fold safety factor for the compound of Example 1.

Thus, about 3 times as many reference compounds are needed to achieve the same GRgg value as in the case of the compound of Example 1, but even without the selectivity in soybeans.

Compounds C and D were non-selective against sida spinosa in soybeans at 7 WAT. Compound I was needed at 4.2 kg / ha and Compound E was needed to achieve a GRgg of 2.8 kg / ha and selectivity factors of 1.1-fold and 1.5-fold, respectively. In contrast, the compound of Example 1 reached a GRgg of only 0.8 kg / ha and had a selectivity factor of 4.7 times in soybeans.

Compounds C, D, and E were non-selective against 35 chicken millet in soybeans at 7 WAT. Compound 28,73971 and Compound of Example 1 had substantially equal safety factors, i. 1.5 times and 1.4 times, respectively.

Thus, the above field experiments show that, with the exception of the control against chicken millet with Compound I, the compound of Example 1 was significantly better than Comparative Compounds C, D, E and I in selectively controlling all three annual weeds in soybeans 7 weeks after treatment.

In the following experiments, which determined the relative herbicidal activity and selectivity for an even longer period of time, the same herbicides used in the above experiments were used again in the field experiments, and this time in separate clay pot containing 3.0-3.5%. organic matter. In parallel experiments, emulsifiable concentrates of the corresponding herbicides were applied to the surface and mixed into the soil before planting for 20 years as a control, further in an amount of 280.5 kg / ha containing the herbicide as active ingredient at a suitable concentration. In these experiments, herbicides were compared against perennial weeds against downy wheat and annual broadleaf weeds against 25 wool, clayey, and bitter buckwheat in soybeans. In these experiments, irrigation was performed corresponding to heavy rainfall of 4.45 cm on the fifth day after treatment ("DAT") and 2.29 cm, 1.52 cm, 1.27 cm and 1.27 cm of rain on the following days. Experimental values 30 are shown in Table IV.

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Referring to the values in Table IV, none of the reference compounds selectively controlled any of the herbaceous herbs in soybean up to 6.7 kg / ha, which was the highest test number of 5, based on 6 weeks and 9.5 weeks of attention. As indicated above, selectivity is demonstrated by a selectivity coefficient or a ratio of 1.0 or greater to a GR 1 / GR 2 ratio; the higher the value the higher the selectivity. In contrast, the compound of Example 19 had a selective control against common wheat, clay and bitter buckwheat at the time of detection of 6.0 weeks and control against common wheat and bitter buckwheat at the time of detection of 9.5 weeks. The herbicidal activity of the compound of Example 1 has been shown to be on the order of 3 or more times greater than that of the reference compounds against common wheat and clay (excluding Compound B) and is approximately two or more times more active than the reference compounds (excluding Compound D during 6 and 9.5 weeks and Compound E during 9.5 weeks). None of the herbicides selectively controlled wool in this experiment, but the compound of Example 1 was more active against this weed than the control compounds at 6 weeks.

Again, according to experimental values based on surface application of herbicides, none of the reference chemicals selectively controlled any weed in the soybean experiment at 6.7 kg / ha 30 or less during the 6 week or 9.5 week observation period except for Compound D against clay at the 9.5 week observation time. . In these experiments, the compound of Example 1 showed a selective weed-grass control against downy wheat and bitter buckwheat at a time point of 6 weeks and against clay at a time point of 9.5 weeks; the safety factor was then slightly 32 7 3 9 71 higher than that of test compound D, i.e. 1.3 and 1.1 times, respectively. Now again, the compound of Example 1 had much better herbicidal activity than the reference compounds in these experiments.

The value in Table IV shows that in terms of unit activity against weeds, soybean tolerance to herbicides, safety factors and herbicide application, the compound of Example 1 had substantially better properties when used as a herbicide before germination than the reference compounds.

The permanent weed control provided by the compound of Example 1 under vigorous irrigation showed that the compound was not easily washed away.

In the following comparative experiments, the compound of Example 1 and Reference Compounds D and E were tested for their selective control against Sida spinosa and blood millet in cotton 20 using both surface application and mixing of the herbicide in the ground before planting; the yellow nutcracker was included in the latter use. The soil in these experiments was loamy soil with 1.7% organic matter. Observations were made at 2, 6, and 9 weeks 25 after treatment. The experiment was repeated three times and the values obtained from the surface application experiments show that the compound of Example 1 had more than twice the unit activity against Sida spinosa compared to compounds D and E after 6 weeks 30 and 1.5 times higher than their activities after 9 weeks. Compound D was non-selective against Sida spinosa in cotton at 6 and 9 weeks. The selectivity coefficients for Compound E after 6 and 9 weeks were 1.1 and 1.2, respectively, compared to 3.3 and 1.8 for the compound of Example 1. Although the unit activities of each of the compounds tested were comparable against millet after 6 weeks, the compound of Example 1 was more active than compound E after 9 weeks and more selective (i.e., SF value> 4.0) than compound D, with an SF value of 2.8.

In experiments in which the herbicide was applied to the soil before planting, after 9 weeks the unit activity of the compound of Example 1 was greater than 10-fold compared to the reference compounds against the yellow nut, slightly less than 2-fold compared to the reference compounds against blood millet and greater than 1 1/3-fold compared to the reference compounds. against spinosa *. In this 15 field experiment, the compound of Example 1 selectively controlled the yellow hazel in cotton for up to 6 weeks after treatment, but the control compounds showed no selectivity even at the 2-week observation time. Although none of the test chemicals selectively controlled sida spinosa in this experiment, the selectivity cut-off range was much closer to the compound of Example 1 than to the other compounds. The compound of Example 1 and Compound E controlled blood-millet after 2 weeks, but were non-selective thereafter; compound D was not selective against blood millet during any of the observation days.

Thus, from the above field experiments on cotton, it can be clearly concluded that the compound of Example 1 was significantly more active than the reference compounds against weeds and sida spinosa while maintaining this activity for a longer time, and that the compound of Example 1 had better selectivity coefficients for these herbs. in relation to. In addition, the compound of Example 1 su 73971 had better unit activity compared to compound E and better selectivity compared to compound D against blood millet in cotton after 9 weeks.

Comparative experiments were further performed between the compound of Example 1 and compounds D and E to determine their relative herbicidal activity and duration of perennial weeds against yellow hazel and common wheat. Compounds 10D and E are known to be the most potent selective herbicides of 2-haloacetanilides and can be considered as suitable reference standards for other herbicides against hazelnut and rye wheat and other weeds. In these experiments, which were repeated 2 times, 25 tubers of yellow walnut and 25 pieces of rhizome of common wheat were planted. The herbicides were combined with the soil surface layer in sufficient quantity to determine the GR 2 value, i. the minimum amount required to achieve 50% weed control; 11.2 kg / ha was the maximum amount and 1.4 kg / ha was the lowest amount used. Observations were made at 3.6, 12, and 18 weeks. After each observation, the topsoil was removed, old tubers and rhizome pieces were removed and replanted and placed in a greenhouse for further treatment. The test results are shown in Table V; "WAT" means "weeks after treatment".

35 73971

Table V

Shelf life in soil GR50

Kg / ha 5 Compound Yellow Nut

_ sara_ Dairy wheat WAT

Example 1 <1.4 <1.4 3 <1.4 <1.4 6 1.4 1.4 12 10 8.4 11.2 18 D <1.4 <1.4 3 1.12 <1.4 6 5.9 5.6 12> 11.2> 11.2 18 15 E <1.4 <1.4 3 1.4 1.7 6 7.8 11.2 12> 11.2> 11.2 18 20 Regarding the values of the yellow nut bar in Table V, they show that 3 weeks after treatment, the GR 2 Q value of each compound was less than 1.4 kg / ha, and that certain differences occurred after 6 weeks.

After 12 weeks, the largest differences in the control of the yarrow were observed. Thus, only 1.4 kg / ha of the compound of Example 1 was needed to control 50% of the weeds, while 5.9 kg / ha of Compound B and 7.8 kg / ha of Compound E were needed to achieve the same level of control of the yarrow. Also after 18 weeks, only 8.4 kg / ha of the compound of Example 1 was needed to control 50% of the nutcrack, while the corresponding amount of compounds D and E averaged about 11.2 kg / ha (the highest amount applied).

Correspondingly, the values for juvenile wheat shown in Table V show that after 6 weeks the compound of Example 1 and Compound D had somewhat better activity compared to Compound E. However, after 12 weeks the compound of Example 1 had a clearly better potency because only 1 .4 kg / ha to achieve the same control of dowel as with 5.6 kg / ha of compound D and 11.2 kg / ha of compound E. The improved herbicidal activity of the compound of Example 1 also appeared after 18 weeks.

An important advantage of the herbicide is its ability to function in a variety of soils. Table VI shows values showing that the compound of Example 1 has a herbicidal activity against yellow-thistle horseradish in cotton and soybean in various soil species with varying organic matter and clay contents. In the treatment, the herbicide was mixed with the soil and the seeds were planted to a depth of 0.05 cm and given a surface watering of 0.6 cm. Ha-20 scans were performed after 18 days of treatment.

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The values shown in Table VI show that the quality of the soil and its organic matter content did not in any way affect the compound of Example 1, which selectively controls the yellow walnut-5 hive in both cotton and soybean soils with 1.0-6.8% organic matter and 1, 8-9.6% clay. The selectivity coefficients were highest in the Sarpy clay soil.

Additional experiments were performed to determine the herbicidal activity of the compound of Example 1 in a soil containing a large amount of organic matter. The experiment was repeated 3 times and the activity of the compound of Example 1 was determined against clay and flour clay in a soybean culture planted in humus-rich soil. Compounds C, D, E and I were also tested for comparative experiments. These experiments were performed both as a pre-seeding treatment and as surface application to humus-rich soil containing 23% organic matter. In these experiments, both in the pre-planting treatment and in the surface application treatment (post-planting), the compound of Example 1 had the highest unit activity against powdery mildew after one week and the pre-planting treatment had the highest selectivity factor in soybeans, i. > 2.7 compared to 1.1 for compounds C and D; compounds E and I were non-selective after 4 weeks. All compounds were non-selective against powdery mildew after 7 weeks in each of the 30 herbicide treatments; compound E was slightly more active than the compound of example 1 after 7 weeks in both herbicide treatments. Against clay, Compound D had the highest unit activity and selectivity factor (1.9) after 7 weeks 35 in both herbicide treatments; in surface application 39 7 3 9 71 the selectivity coefficient of compound D was almost twice as high as the corresponding values of the compound of Example 1 and compound E; the other compounds did not selectively control clay after 7 weeks in either herbicide treatment. The compound of Example 1 (S.F: 2.0) and compounds C and E (S.F: 1.0) each selectively control clay after M weeks of herbicide treatment prior to planting.

The above experiments show that, compared with the reference compounds, the compound of Example 1 achieves the best selectivity control of flour whey in soybean bean soils in humus-rich soils when applied before planting; these 15 compounds had the highest unit activity and selectivity factor H after one week in the experiment. In addition, the compound of Example 1 selectively controls clay for up to about 7 weeks in the surface application treatment and up to 4 weeks in the treatment prior to implantation. Compound D had the best clay control after 7 weeks in both treatments. The relative potency of the compound of Example 1 and Compound D should be further compared to the relative potency of these compounds in soils with less organic matter, e.g. 3.0-3.5%, with the compound of Example 1 showing better unit activity and shelf life in soil combined with selectivity in soybeans. , in both surface application and pre-planting treatments as shown in Table IV.

The above description demonstrates the excellent herbicidal activity of the compounds of the invention in controlling perennial weeds and annual broadleaf weeds in soybean 35 and cotton. In addition, it has also been shown that, e.g. in experiments on chicken millet and blood millet, the compounds according to the invention also have excellent herbicidal activity against annual narrow-leaved weeds such as grasses. In fact, as will be shown later for certain one-year-old herbs, the compounds of the invention are clearly superior to most known herbicidally active and / or commercially available 2-haloacetanilides. As can be seen from the experimental results, there are cases in which the known 1α-haloacetanilides have a better herbicidal activity than the compounds according to the invention with regard to specific annual weeds under comparable conditions. However, comparative experiments also make it clear that the compounds 15 of the invention as a whole are equally good and often better, sometimes considerably better than the best 2-haloacetanilides as selective herbicides for controlling annual and perennial narrow-leaved weeds in soybeans, cotton, peanuts and others.

In a greenhouse experiment performed before germination, the compounds of Examples 1 and 11 were compared with compounds C and I (both commercial 2-haloacetanilides) to determine their relative herbicidal activity against one-year-old narrow-leaf weeds such as grasses in soybeans. In this experiment, herbicides were mixed into the soil before seeding and seedings were made 17 days after treatment; experimental values 30 are shown in Table VII and represent the averages of the two experiments.

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From the values in Table VII, it can be clearly seen that: (1) Compound I had the lowest unit activity and selectivity of all compounds against each weed in the experiment and had no selectivity in soybean for wild proso millet, red rice or scab; (2) Compound C was as active as the compounds of Examples 1 and 11 more active against shattercane and wild proso logs; (3) The compounds of Examples 1 and 11 were both superior to the known compounds against Johnson grass and scabies; (4) the compound of Example 11 was more active against alexander grass and the compound of Example 1 was more active against red millet than the known compounds.

Thus, in summary, based on the reference values in Table VII, either or both compounds of the invention were herbicidal as effective as the best known comparator-20 against one-year-old narrow-leaved weeds ("shattercane" and wild proso millet) and significantly superior to four narrow-leaved herbaceous weeds, , red rice and scabies grass). In particular, the excellent unit activity of the compound of Example 1 against John's wort (GRgg = 0.14 kg / ha), which had an excellent selectivity factor of about 8.0 times in soybeans compared to the selectivity factor of compound C> 2.0 times, and being better than the corresponding value of known compounds. Similarly, the compound of Example 11 had excellent unit activity against alexander grass and scabies, with selectivity factors of 8.0-fold and 4.0-fold in soybean and bean, respectively, compared to 4.0-fold and 1.0-fold, respectively, for the selectivity coefficients of compound C.

43 73971

Soybeans were tested in another experiment and included Texas (Panicum texanum) and autumn millet weeds along with the other annual grasses mentioned in the previous experiment. In this experiment, the compounds of Examples 1 and 12 were compared with respect to their known compounds C, D and I after pre-emergence treatment for herbicidal activity. The herbicides were mixed with the soil and, if necessary, watered. The maximum amount of herbicide used in the experiments was 1.12 kg / ha, in which case the exact GRgg and GR1 values above 1.12 kg / ha may be somewhat vague. Comments were made 2 weeks after treatment. The values for this experiment are shown in Table VIII.

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From the analytical values shown in Table VIII, it can be seen that the compounds of Examples 1 and 12 had the highest unit activities and selectivities of all the compounds in the experiments against scabies-5 grass and "shattercane"; the compound of Example 12 had the highest activity and selectivity against scabies and the compounds of Examples 1 and 12 had the highest activities against wild prosoir together with Compound D 10 and the activities against autumn millet were the same for all compounds. However, the compounds of the invention were more selective in soybean culture than Compound D against wild proso millet. In addition, the compound of Example 12 was the second best compound in terms of activity

Against Texas millet and red rice, and the compound of Example 1, together with Compound D, had the second highest activity against scabies. Compound D was the most active of the test compounds against 20 Texas millet, alexander grass, and red rice.

Thus, from the above comparative experimental values for herbicidal activity against annual grasses, the compounds of the invention have better herbicidal activity than the leading known compounds against certain annual grasses, e.g. herbicidal efficacy against 30 others, e.g., blood millet (surface treatment), various wild millets, alexander grass, and red rice.

Other experiments in a greenhouse and / or in the field have further shown a selective control of the compounds according to the invention against other weed species in connection with soybeans, cotton and / or other crops 1.6 73971. For example, the compound of Example 1 has been shown to selectively control purple hazelnut hay and giant hay (Setaria faberi) in cotton and giant hay and velvet leaf 5 in soybean cultivation. Further comparing to known relevant acetanilide herbicides, the compound of Example 1 has shown improved herbicide against resistant weeds such as wool, sunflower and bile grass. Other weeds against which the compounds of the invention have been shown to be herbicidally active are Canadian thistle, wild hop, goose, turnip, etc. As indicated above, the compounds of the invention have been found to be effective herbicides in a variety of useful plants. The above description and experimental values were mainly aimed at weed control in the context of soybeans and cotton, whose yields and weed control are of greatest interest. Additional experiments have shown the utility of the compounds of the invention in conjunction with other useful plants as described below.

In a greenhouse experiment, the compounds of Examples 11 and 12 were tested for their herbicidal-25 activity against rye wheat in oilseed rape, folding bean, sorghum and wheat. The herbicide treatment was performed before germination. Both test compounds selectively controlled jow wheat in oilseed rape and folding beans, with the selectivity factor of the compound of Example 11 being 3.5 times in both harvests and the corresponding value of the compound of Example 12 being 3.0 times in both harvests. In this experiment, both compounds were non-selective against jow wheat in sorghum and wheat.

Separate greenhouse experiments also examined the herbicidal activity of the compound of Example 1 H7 73971 against yellow nutmeg and common wheat in oilseed rape, peanut, sugar beet, sorghum, wheat and barley; the herbicide was mixed with the soil before germination. In these experiments, Compound D was Reference Compound 5 against downy wheat and Compound E was Comparative Compound against Yellow Nut. In the case of common wheat, observations were made 19 days after treatment and in the case of yellow walnut, 18 days after treatment; experimental values are shown in Table 9; the selectivity coefficients for herbisi-10 are shown in parentheses after the GRig values for the corresponding plants.

43 73971

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The values in Table IX show that the compound of Example 1 and Compound D both selectively control juvenile wheat in peanut, oilseed rape, sugar beet, wheat and barley, 5 but the selectivity coefficient of the compound of Example 1 was significantly higher than that of Compound D in peanut, oilseed rape and sugar beet. equal in wheat and lower in barley. The compound of Example 1 selectively controlled the yellow nut bar in both crop experiments, except for sugar beet, while Compound E did not selectively control the yellow nut bar in sugar beet, sorghum, or wheat.

The high unit activities of compounds D and E-15 ti are generally characterized by a short-term effect in the greenhouse (2-6 weeks) against common wheat and yellow walnut. However, as discussed above, all relevant experimental values both in the greenhouse and in the field have confirmed the consistently better unit activity of the compound of Example 1 against common wheat and yellow walnut and the yield selectivity compared to compounds D and E, especially over longer periods. In this context, reference is again made to: (1) Table IV, which contains 25 comparative field test values up to 9.5 weeks for the efficacy of these compounds against downy wheat and other weeds in soybeans; (neither of compounds D and E selectively controlled wool wheat in soybeans even at the 3-week observation period after 30 treatments; (2) to the above description of comparative field test values for the efficacy of these compounds against yellow nut and other weeds in cotton for up to 9 weeks (neither of D and E (73) Table V, which shows the comparative durations in soil of the compound of Example 1 and compounds D and E against yellow walnut and Juola-5 wheat at 3,6, 12 and 18 weeks, respectively. the compound of Example 1 had a higher unit activity than the compounds D and E after 3 weeks (multiple after 12 weeks) and a vague amount in the inspection after 18 weeks It should also be mentioned that the combined excellent unit activity, duration in soil and the selectivity of the crop compared to compounds D and E in the case of yellow fever and common wheat is also applicable to the relative potency of these compounds in the case of several other weeds especially johnson grass, hemp sesbania, "prickly bind", bitter buckwheat, flour whey, etc.

In one multi-crop / weed experiment, the activity of 20 compounds of Example 1 against certain annual weeds in different crops was examined in a field experiment. In parallel experiments, Herbicides were applied to the surface and mixed before planting. Observations were made 33 days after the treatment, which was carried out by mixing the herbicide in the soil before planting, and 34 days after the treatment, which was carried out by applying the herbicide to the soil surface. In both experiments, the compound of Example 1 selectively controls stem millet and green thistle grass (Setaria viridis) in corn, soybeans, cotton, shrub beans, and peanuts; the flour defect was also controllable in soybeans. In addition, in the treatment where the herbicide was mixed into the soil before planting, chicken millet and headland were also selectively controllable in sorghum and sweet corn.

51 73971

Thus, it is apparent from the detailed description above that the compounds of the invention have been shown to have unexpected and clearly better herbicidal properties both in absolute and relative terms compared to the structurally closest relevant compounds, other known related homologues and analogues and commercial 2-haloacetanilides. In particular, the compounds of the invention have been shown to have excellent unit activity, long shelf life in soil and crop safety for perennial and annual broadleaf and narrow-leaf weeds in soybeans, cotton, peanuts, oilseed rape and folding beans and other useful plants. In addition, more particularly, the compounds of the invention have been shown to have better herbicidal activity against perennial yarrow and common wheat; annuals against broadleaf such as Sesbania exaltata, sida spinosa, Jam-20 horsetail and bitter buckwheat, and annuals with narrow-leaved weeds such as chicken millet, blood millet, Sorghum bicolor and scabies. In addition, the compounds of the invention have been shown to be generally comparable in efficacy to the best known known compounds for controlling other annual herbaceous weeds such as John's wort, blood millet (surface application), hay fever, Texas millet, autumn millet, wild proso millet, alexophora against weeds such as clay and mad grass. In addition, the compounds of the invention have been found to have improved activity and efficacy against resistant annual broadleaf weeds such as sunflower, bile grass, wool and velvet leaf.

Toxicological studies with 52,73971 of the compound of Example 1 have shown that the compound is completely safe. It was mildly toxic when administered in the diet (single dose OLDj.q-2,600 mg / kg), mildly toxic to skin 5 (DLDgg-5.010 mg / kg), and mildly irritating to eyes and skin. No special handling is required in addition to normal precautions.

The herbicidal compositions of the invention, including concentrates which must be diluted before use, contain at least one active ingredient and an additive in liquid solid form. The compositions are prepared by mixing the active ingredient with an additive comprising a diluent, extenders, carriers and conditioning agents to give the compositions in finely divided solid form, granules, pellets, solutions, dispersions or emulsions. Thus, the active ingredient may be used in combination with an additive such as a finely divided solid, a liquid of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent, or any combination thereof.

The compositions of the invention, especially liquids and wettable powders, preferably contain, as a conditioning agent, one or more surfactants in an amount sufficient to make the composition readily dispersible in water or oil. The addition of a surfactant to the composition greatly improves its effectiveness. By surfactant is meant that wetting agents, dispersing agents, suspending agents, emulsifying agents are included in this term. Anionic, cationic and non-ionic substances can be used for this purpose as well.

Preferred wetting agents are alkylbenzene-35 and alkyl naphthalene sulfonates, sulfated fatty acid alcohols, amines or acid amides, long chain acid esters of sodium isothionate, sulfonic acid sulfonate esters, sulfated or sulfonated esters of sodium sulfosuccinate, sulfated or sulfonated esters. glycols, polyoxyethylene derivatives of alkylphenols (especially isooctylphenol and nonylphenol) and polyoxyethylene-10 derivatives of higher fatty acid esters of hexitol anhydrides (e.g. sorbitan). Preferred dispersants are methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate and polymethylene bisnaphthalene sulfonate.

Wettable powders are water-dispersible compositions containing one or more active ingredients, an inert solid extender, and one or more wetting agents and dispersants. Inert solid extenders are usually of 20 mineral origin such as natural clays, diatomaceous earth and synthetic minerals derived from silica and the like. Examples of such extenders are kaolinites, attapulgite clay and synthetic magnesium silicate. The wettable powders of the invention will usually contain from about 0.5 to 60 parts (preferably from 5 to 20 parts) of active ingredient, from about 0.25 to 25 parts (preferably from 1 to 15 parts) of wetting agent, from about 0.2 5 to 25 parts (preferably 1.0 to 15 parts) of dispersant and 5 to 95 parts (preferably 5 to 50 parts) of an inert solid extender, all parts being calculated. by weight of the total composition. If necessary, about 0.1 to 2.0 parts of solid inert extender may be replaced by an anti-corrosion agent or an antifoam agent, or both.

35 Other preparations include poly-concentrated teas containing from 0.1 to 60% by weight of active ingredient with a suitable excipient; these dusts can be diluted for use to concentrations in the range of about 0.1 to 10% by weight.

Aqueous suspensions or emulsions can be prepared by mixing an aqueous mixture of the water-insoluble active ingredient and the emulsifying agent until uniform and then homogenizing to obtain a stable emulsion of very fine portions.

The resulting concentrated aqueous suspension is characterized by its very small particle size, so that the opacity is uniform when diluted and sprayed. Suitable concentrates for these preparations contain about 0.1-60%, preferably 5-50% by weight of active substance, the upper limit being determined by the solubility of the active substance in the solvent.

To prepare a second formulation of aqueous suspensions, the water-immiscible herbicide is encapsulated to form a microencapsulated phase dispersed in an aqueous phase. In one embodiment, small capsules are formed by combining an aqueous phase containing a lignin sulfonate emulsifier and a water-immiscible chemical and polymethylene polyphenyl isocyanate, dispersing the non-aqueous phase into the aqueous phase, and then adding a multifunctional amine. The isocyanate and amine compounds react to form a solid urea shell wall around the water-immiscible chemical particles to form their microcapsules. In general, the concentration of the microencapsulated substance is in the range of 480 to 700 g / l, based on the total composition, and is preferably 480 to 600 g / l.

Concentrates are usually solutions of the active ingredient in a water-immiscible or partially water-immiscible solvent together with a surfactant. Suitable solvents for the active ingredients according to the invention are dimethylformamide, dimethylsulfoxide, N-methylpyrrolidone, hydrocarbons and water-immiscible ethers, esters or ketones. However, other liquid concentrates can be prepared by dissolving the active ingredient in a solvent and then diluting, e.g. with fuel oil, to a spray concentration.

The compositions as a concentrate generally contain from about 0.1 to 95 parts (preferably from 5 to 60 parts) of active ingredient, from about 0.25 to 50 parts (preferably from 1 to 25 parts) of surfactant and, if required, from about M to 94 parts of solvent. solvent, all parts by weight of the total emulsifiable oil.

Granules are physically stable particulate compositions that contain the active ingredient attached or distributed to an inert finely divided extender. To rinse the active ingredient from the granules, a surfactant such as those mentioned above may be present in the composition. Natural clay, pyrophyllite, illite and vermiculite can be used as mineral extenders. Preferred extenders are porous, absorbent, preformed particles such as preformed and screened particulate attapulgite or mesh-expanded particulate vermiculite and finely divided clays such as kaolin clays, hydrated attapulgite or pentonite clays. These extenders are sprayed or mixed with the active ingredient 30 to form herbicidal granules.

The granular compositions of the invention may contain about 0.1 to 30 parts, preferably about 3 to 20 parts of active ingredient per 100 parts of clay and 0 to 5 parts of surfactant per 100 parts of clay, based on weight.

56 73971

The compositions of the invention may also contain other additives, e.g. fertilizers, other herbicides, other pesticides, safeners and the like, which are used as additives 5 or in combination with any of the above-mentioned additives. Useful chemicals with the active ingredient of the combination include, for example, triazines, ureas, carbamates, acetamides, acetanilides, ureas, acetic acid or phenol derivatives, thiol-10-carbamates, triazoles, benzoic acids, nitriles, biphenyl ethers and the like:

Heterocyclic Nitrogen / Sulfur Derivatives 2-Chloro-4-ethylamino-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-dihydrodipyrido (1,2- a: 2R, 1f-c) -pyrazidinium salt 5-Bromo-3-isopropyl-6-methyluracil 1,1r-dimethyl-4,4'-bipyridinium

Urea NT- (4-chlorophenoxy) -phenyl-N, N-dimethylurea N, N-dimethyl-N '- (3-chloro-4-methylphenyl) urea 3- (3,4-dichlorophenyl) -1,1 -Dimethyl-urea 1,3-dimethyl-3- (2-benzothiazolyl) -urea 3- (p-chlorophenyl) -1,1-dimethylurea 1-butyl-3- (3,4-dichlorophenyl) -1-methylurea

Carbamates / Carbonates 2-Chloroallyl diethyldithiocarbamate S- (4-chlorobenzyl) N, N-diethylthiol carbamate Isopropyl N- (3-chlorophenyl) carbamate S-2,3-dichloroallyl N, N-di- isopropylthiol carbamate Ethyl N, N-dipropylthiol carbamate 3 5 S-propyl dipropyl thiol carbamate 57 7 3 9 71

Acetamides / acetanilides / anilines / amides 2-chloro-N, N-diallylacetamide N, N-dimethyl-2,2-diphenylacetamide N- (2,4-dimethyl-5 - [(trifluoromethyl) sulfonyl] -5-amino / phenyl ) acetamide N-isopropyl-2-chloroacetanilide 2 ', 61-diethyl-N-methoxymethyl-2-chloroacetanilide 2f-methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide 10 o E, N, N-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide Acids / esters / alcohols 2,2-dichloropropionic acid 15 2-methyl-1 * -chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propionate 3-amino-2,5-dichlorobenzoic acid 20 2-methoxy-3, 6-Dichlorobenzoic acid 2,3,6-trichlorophenylacetic acid N-1-naphthylphthalamic acid Sodium 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate 4,6-Dinitro-o-sec-butylphenol N- (phosphonomethyl) glycine and its C 1-8 monoalkylamine and alkali metal salts and combinations thereof

Ethers 30 2,4-Dichlorophenyl-4-nitrophenyl ether 2-chloro-o, o (? 4 "trifluoro-p-tolyl-3-ethoxy-4-nitrodiphenyl ether 58 7 3 9 71

Miscellaneous 2,6-Dichlorobenzonitrile monosodium acid methanesononate Disodium methanesononate 5 Fertilizers used in combination with the active ingredient are, for example, ammonium nitrate, urea, potash and superphosphate. Other additives are substances in which plant organisms take root: and grow such as compost, livestock manure, humus, 10 sand, and the like.

The following embodiments of the herbicidal preparations described above are exemplified.

I · Emulsifiable concentrates 15 4,6-dinitro-o-sec-butylphenol N- (phosphonomethyl) -glycine and its C 1-8 monoalkylamine and alkali metal salts and their combinations

% By weight 20 A. Compound of Example 1 50.0

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and Atlox 3438F) 5.0 25 Monochlorobenzene 45.0 100.00 B. Compound of Example 12 85.0 Calcium dodecyl sulfonate / alkylaryl-polyether-alcohol mixture 4.0 Cg aromatic hydrocarbon solvent 11.0 100, C. Compound of Example 13 5.0 Calcium dodecylbenzenesulfonate Mixture of polyoxyethylene ethers 35 (e.g. "Atlox 3437F") 1.0

Xylene 94.0 100.00 59 73 971 II. Nesteväkevöitteet

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Xylene 90.0 5 100.00 B. Compound of Example 2 85.0

Dimethyl sulfoxide 15.0 100.00 C. Compound of Example 3 50.0 N-methylpyrrolidone 50.0 100.00 D. Compound of Example 4 5.0

Ethoxylated castor oil 20.0 "Rhodamine B" 0.5 Dimethylformamide 74.5 100.00 III. Emulsions A. Compound of Example 1 40.0

Polyoxyethylene / polyoxy-propylene block copolymer with butanol (e.g. Tergito® XH) 4.0

Water 56.0 100.00 B. Compound of Example 5 5.0 Polyoxyethylene / polyoxypropylene block copolymer with butanol 3.5

Water 91.5 100.0 30 IV. Wettable powders% by weight A. Compound of Example 1 25 q

Sodium lignosulfonate 3.0

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Attapulgite 98.0 100.0 B. Compound of Example 8 60.0

Montmorillonite 40.0 100.0 C. Compound of Example 9 30.0 Bentonite 70.0 100.00 D. Compound of Example 11 1.0

Diatomaceous earth 99.0 100.00 25 VI. Hail

% By weight A. Compound of Example 1 15.0

Granular attapulgite (20/40 mesh) 85.0 100.00 3 0 B. Compound of Example 12 30.0

Diatomaceous earth (20/40) 70.0 100.00 61 73971 C. The compound of Example 13 0.5

Bentonite (20/40) 99.5 100.0 D. Compound of Example 14 5.0 Pyrophyllite (20/40) 95.0 100.00 VII. Microcapsules A. The compound of Example 1 encapsulated in a polyurea shell wall ηq 49.2

Sodium lignosulfonate (e.g.

Reax 8 ^ ¾) 0.9

Water 49.9 100.00 c B. Compound of Example 12

Ib encapsulated within a polyurea shell wall 10.0

Potassium lignosulfonate (e.g.

Reax (C-21) 0.5

Water 98.5 20 100.00 C. The compound of Example 13 encapsulated within a polyurea shell wall 80.0

Magnesium salt of lignosulphate 2 5 (Treax® LTM) 2.0

Water 18.0 100.00

When working in accordance with the invention, effective amounts of the acetanilides of the invention are applied to soil containing plants or combined with an aqueous medium in any suitable manner. The application of liquid or solid compositions to the soil can be carried out in a manner known per se, e.g. with powder burners, boom-35 and hand sprayers or spray dusters. Compositions 52 7 3 9 71 can also be applied from an aircraft as a dust or spray due to their low dose effectiveness. The application of herbicidal compositions to plants is usually performed by adding the compositions to an aqueous medium in areas where plant control is desired.

The application of an effective amount of the compounds of the invention to the growth sites of unwanted weeds is essential and critical to the practice of the present invention. The exact amount of active ingredient to be used depends on various factors, such as the plant species and their stage of development, the soil type and its condition, the amount of precipitation and the specific acetanilide used. In the selective treatment before germination, a dose of about 0.02 to 11.2 kg / ha, preferably about 0.04 to 5.60 kg / ha or suitably 1.12 to 5.6 kg / ha of acetanilide is usually applied to the plants or soil. . Smaller or larger amounts may be used in certain cases as needed. One skilled in the art can readily determine the optimum amount to use in each case based on this description.

The term "land" or "soil" as used in this specification means, in its broadest sense, all 25 conventional soils defined in

Webster’s New International Dictionary, Second Edition, Unabrindged (1961). Thus, this term refers to any substance or medium in which rooting and growth can occur and includes not only 30 soils but also compost, livestock manure, sludge, humus, sand and the like that supports plant growth.

Although the invention has been described with reference to specific embodiments, their details are not intended to limit the present invention.

Claims (22)

63 73971 1. A 2-haloacetanilide compound, characterized in that it has the formula 50 CH 2 Cl 2 CH 2 OR Compound according to Claim 1, characterized in that it is 2'-methoxy-6'-methyl-3-N- (isopropoxymethyl) -2-chloroacetanilide. e * 73971 3. A compound according to claim 1, which comprises 2'-methoxy-6'-methyl-N-30 (ethoxymethyl) -2-chloroacetanilide. Compound according to Claim 1, characterized in that it is 2'-methoxy-61-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 4. A compound according to claim 1, which comprises 2'-methoxy-6'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. Compound according to Claim 1, characterized in that it is 2'-methoxy-61-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. 5. A compound according to claim 1, which comprises 35, 2-ethoxy-6, -methyl-N- (allyloxymethyl) -2-chloroacetanilide. 68 73971 Compound according to Claim 1, characterized in that it is 2'-ethoxy-6'-methyl-N- (allyloxymethyl) -2-chloroacetanilide. A compound according to claim 1, which is 2'-ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide. Compound according to Claim 1, characterized in that it is 2'-ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide. 7. A compound according to claim 1, which comprises 2'-ethoxy-6'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. Compound according to Claim 1, characterized in that it is 2'-ethoxy-6'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide 8. A compound according to claim 1, which comprises 2'-n-propoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 9. A compound according to claim 1, which comprises 21-isopropoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. Compound according to Claim 1, characterized in that it is 2 * -n-propoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. Compound according to Claim 1, characterized in that it is 2'-isopropoxy-61-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 10. A compound according to claim 1, which comprises 2-isopropoxy-6β-methyl- 10 R2 - color R ar ethyl, n-propyl, isopropyl, isobutyl, tert-butyl, cyclopropylmethyl, ally! Elder propargyl; Compound according to Claim 1, characterized in that it is 2'-isopropoxy-6'-methyl-N- (n-propoxymethyl) -2-chloroacetanilide. R2 (O) -SO5 wherein R is ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl; R is methyl, ethyl, n-propyl or isopropyl and R 2 is hydrogen, methyl or ethyl; with the proviso that: when R 2 is hydrogen, then R 1 is ethyl and R 1 is allyl; when R 2 is ethyl, then R 1 is methyl and R is isopropyl; When R 1 is methyl, then R is ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl; when R 1 is ethyl, then R is sec-butyl, allyl or propargyl; When R 1 is n-propyl, then R 2 is ethyl; and when R 1 is isopropyl, then R is ethyl or n-propyl. A compound according to claim 1, which comprises 2'-ethoxy-N- (allyloxymethyl) -2-chloroacetanilide. Compound according to Claim 1, characterized in that it is 2'-ethoxy-N- (allyl-1-oxymethyl) -2-chloroacetanilide. A compound according to claim 1, entry -20 for the purposes of this invention, which comprises 21-methoxy-6'-ethyl-N- (isopropoxymethyl) -2-chloroacetanilide. Compound according to Claim 1, characterized in that it is 2'-methoxy-6'-ethyl-N- (isopropoxymethyl) -2-chloroacetanilide. 13. An herbicidal composition comprising the active compound 2-haloacetanilide, which is selected from the group consisting of active compound 25 and 2-haloacetanilide according to the formula 0 C1CH C10iRN 30 0Rl 35 color R is ethyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl; 69 73971 R is methyl, ethyl, n-propyl or isopropyl, and hydrogen, methyl or ethyl; förutsatt att, da R2 is hydrogen, R1 is ethyl and R is allyl; R 2 is ethyl, methyl or R is isopropyl; 5 is R 1 is methyl, is R ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl; da R is ethyl, R is sec-butyl, allyl or propargyl; da R 1 is n-propyl or R ethyl and 10 is R-, isopropyl, is R ethyl or n-propyl. 13. A herbicidal composition comprising 2-haloacetanilide as active ingredient, characterized in that it contains as active ingredient one or more 2-haloacetanilide compounds of the formula es 73971 O C1CH2C. CH 2 OR R - (oTORR 1 wherein R is ethyl, n-propyl, isopropyl, tert-butyl, sec-butyl, cyclopropylethyl, allyl or propargyl; is methyl, ethyl, n-propyl or isopropyl and R 2 is hydrogen, methyl or ethyl; with the proviso that: when R 2 is hydrogen, then R 1 is ethyl and R is allyl, when R 2 is ethyl, then R 1 is methyl and R is isopropyl, when R 2 is methyl, then R 1 is ethyl, isopropyl 1, isobutyl, sec-butyl or cyclopropylmethyl, when R 1 is ethyl, then R is sec-butyl, allyl or propargyl, when R 1 is n-propyl, then R is ethyl, and when R 1 is isopropyl, then R 1 is is ethyl or n-propyl. A composition according to claim 13, which comprises 2'-methoxy-6'-methyl-N- (isopropoxymethyl) -2-chloroacetanilide. Composition according to Claim 13, characterized in that it contains 2'-methoxy-6'-methyl-N- (isopropoxymethyl) -2-chloroacetanilide. 15. A composition according to claim 13, wherein 2'-netoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide is used. N- (n-propoxymethyl) -2-chloroacetanilide. R is methyl, ethyl, n-propyl or isopropyl, and R2 is methyl or ethyl; forutsatt att, da är väte, är R ^ ethyl and R är allyl; R 2 is ethyl, R 4 is methyl and R is isopropyl; da R is methyl, is R ethyl, isopropyl, isobutyl, 2. sec-butyl or cyclopropylmethyl; da R 1 is ethyl, R is sec-butyl, allyl or propargyl; when R1 is n-propyl, then R is ethyl; and R 1 is isopropyl, R is ethyl Elder n-propyl. 2. A compound according to claim 1, which comprises 2'-methoxy-6'-methyl-N- (isopropoxymethyl) -2-chloroacetanilide. Composition according to Claim 13, characterized in that it contains 2T-methoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 16. A composition according to claim 13, which comprises 2'-methoxy-6'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. Composition according to Claim 13, characterized in that it contains 2'-methoxy-6'-35 methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. 66 7 3 9 71 17. A composition according to claim 13, which comprises 2'-ethoxy-6R-methyl-N- (allyloxymethyl) -2-chloroacetanilide. Composition according to Claim 13, characterized in that it contains 2'-ethoxy-6'-methyl-N- (allyloxymethyl) -2-chloroacetanilide. 18. A composition according to claim 13, which comprises 2 * -ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide. Composition according to Claim 13, characterized in that it contains 2'-ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide. A composition according to claim 13, which comprises 2'-ethoxy-6'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. Composition according to Claim 13, characterized in that it contains 2'-ethoxy-6'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetane-Lidia. 20. A composition according to claim 13, wherein the compound comprises 2'-n-propoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. Composition according to Claim 13, characterized in that it contains 2'-n-propoxy-6 * -methyl-N- (ethoxymethyl) -2-chloroacetanilide. 21. A composition according to claim 13, which comprises 2'-isopropoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. Composition according to Claim 13, characterized in that it contains 2'-isopropoxy-6 * -methyl-N- (ethoxymethyl) -2-chloroacetanilide. Composition according to Claim 13, characterized in that it contains 2'-isopropoxy-6'-methyl-N- (n-propoxymethyl) -2-chloroacetane-Lidia. Composition according to Claim 13, characterized in that it contains 2'-ethoxy-N- (allyloxymethyl) -2-chloroacetanilide. · 24. Composition according to Claim 13, characterized in that it contains 2'-methoxy-6'-ethyl-N- (isopropoxymethyl) -2-chloroacetanilide. 67 73971 1. Formation of 2-haloacetanilide, which is not included in the form, 5 0 cich2c ch2or N A composition according to claim 13, which comprises 2'-isopropoxy-6'-methyl-N- (n-propoxymethyl) -2-chloroacetanilide.