NL8101327A - 2-HALOGENACETANILIDS WITH HERBICIDE ACTION. - Google Patents

Description

- 1 - β 1 * 2-haloacetanilides with herbicidal action.

The invention relates to 2-haloacetanilides and their use in agriculture, for example as herbicides.

The prior art relevant to the present invention includes numerous descriptions of 2-haloacetal anilides which may be unsubstituted or substituted with a wide variety of substituents on the anilide nitrogen atom and on the anilide ring, including alkyl, alkoxy , alkoxyalkyl groups, halogen atoms, etc.

Applicant as the closest state of the compounds of the invention which are characterized in that they carry an alkoxymethyl group on the anilide nitrogen, an alkoxy group in one ortho position and a particular alkyl group in the other position. the art discloses 15 U.S. Patents 3,442,945 and 3,547,620. The most relevant disclosures in said patents are the compounds 2, -tert-butyl-2-chloro-N-methoxymethyl-6T-methoxyacetanilide and its bromine analog (Examples 18 and 34 of U.S. Pat. No. 3,547,620, respectively). Examples 18 and 20 of U.S. Patent 3,442,945).

U.S. Patents 4,070,389 and 4,152,137 disclose a general formula comprising compounds of the type disclosed in said U.S. Patents 3,442,945 and 3,547,620. However, the only specific compound with an alkyl group in one ortho position and an alkoxy group in the other ortho position described has an alkoxyethyl group on the anilide nitrogen atom; compounds of this type are discussed in more detail below.

Other less relevant prior art 30 is Belgian patent 810,763 and German patent application 2,402,983; the compounds of these references include compounds of the type described in U.S. Pat. Nos. 4,070,389 and 8101 327 V * - 2 - 4,152,137 mentioned above and are characterized by an alkoxyalkyl group having two or more carbon atoms between the anilide nitrogen atom and the oxygen atom of the alkoxy group . The most relevant specific disclosures in the aforementioned Belgian Pat. in the other ortho position; with regard to Belgian patent 810,763, reference is made to compounds no. 7, 13 and 10 18; other less relevant homologs of these compounds are also described, for example compounds 6, 9, 16 and 17, which have methoxyethyl or methoxypropyl groups substituted on the nitrogen atom, and a methoxy or ethoxy group in one ortho position and a methyl group in the other orthoposition.

The above-mentioned U.S. Patent 3,442,945 contains some herbicidal data regarding those above-mentioned compounds which have a chemical configuration very closely related to the compounds of the invention, and some data are provided in the other patents for other homologous and analogous compounds which are less closely related in chemical structure, for example the said compounds 6 and 9 in Belgian patent 810,763. More specifically, these most relevant references, while describing herbicidal activity on a variety of weeds, do not provide data at all for any of the compounds shown to additionally and / or simultaneously lead to control of the difficult perennial weeds, cultivated grass and yellow cypergrass and a wide spectrum of annual weeds, including such hard-to-kill annual broadleaf weeds such as prickly sida, sesbania hemp, jimson herb (Datura stramonium), etc., and annual grass weeds , such as seedling Johnston grass (Sorghum halepense), splin territe, alexander grass (Brachiaria), finger grass (Texas, falls wild proso millet), red rice and itch grass (Raoul grass), under 35 simultaneous control of other harmful perennial and one-year-old weeds, for example water pepper, loosestrife, Melganze- *> 8101327 * i - 3 - foot, needle spikes, Digitaria adscendens and cephalus.

A. very useful and desirable feature of herbicides is the ability to maintain weed control over a long period of time, the longer the better, during each harvest-5 season. In many of the known herbicides, weed control is sufficient for only two to three weeks, or in some superior cases, perhaps up to four to six weeks, before the chemical loses its effective phytotoxic properties. Therefore, one drawback of most known herbicides is their relatively short soil life.

Another drawback of some known herbicides, somewhat related to soil longevity under normal weather conditions, is the lack of weed control persistence at heavy control drop, which deactivates many herbicides.

A further disadvantage of many known herbicides is the limitation of their use in specified soil types, ie, although some herbicides are effective in soils with small amounts of organic matter, they are ineffective in other soils containing a lot of organic matter, or vice versa. It is therefore advantageous if a herbicide can be used in all soil types, ranging from light organic to heavy clay and peat.

Yet another drawback of many known herbicides is their limitation to a certain effective mode of administration, for example, by surface application before emergence or incorporation into the soil. It is highly desirable to be able to apply a herbicide by any application, either by application to the surface or incorporation into the soil.

Finally, some herbicides have the disadvantage that it is necessary to adopt and maintain special handling procedures due to their toxic nature. From there is a further desideratum that a herbicide is safe to handle.

It is therefore an object of the invention to provide a group of herbicidal compounds which overcome the above drawbacks of the prior art and provide a multitude of advantages which have hitherto not been achieved within a single group of herbicides.

An object of the present invention is to provide herbicides that control hard-to-kill perennial and annual weeds, such as cultivated grass, yellow cyper grass, seedling johnsong grass (Sorghumbalepense), prickly sida, sesbania hemp, splinter reed, alexander grass, finger grasses, red rice and itch grass, as well as and in addition a wide spectrum of other noxious weeds, such as water pepper, loosestrife, Melganze-10 foot, jimson weed, needle spike, coot and digitaria, as well as providing improved suppression of resistant weeds such as ragwort, indoor maple, ipomoea and burdock , while maintaining crop safety in a variety of crops, including soybeans, cotton, groundnuts, rapeseed and / or string beans.

A further object of the invention is to provide herbicidal effectiveness in the soil for periods up to 18 weeks.

Yet another object of the invention is to provide herbicides which are resistant to leaching and dilution due to high humidity conditions, for example heavy rainfall.

Yet another object of the invention is to provide herbicides effective on a wide variety of soils, for example, ranging from light medium organic to heavy clay and peat.

Another advantage of the herbicides of the invention is the flexibility available in the method of application, that is, by application to the surface before emergence and incorporation into the soil.

Finally, it is an advantage of the herbicides of the invention that they are safe and do not require special handling procedures.

The above-mentioned and other objects of the invention will become more apparent from the detailed description given below.

The present invention relates to compounds having herbicidal activity, herbicidal compositions containing these compounds as active ingredients and a method for use as herbicidal of these preparations in certain crops.

It has now been found that a selective group of 2-ha-5 logenoacetanilides, characterized by specific hydrocarbyloxy-methyl groups on the anilide nitrogen atom, specific alkoxy groups in one ortho position and hydrogen or a methyl or ethyl group in the other ortho position unexpectedly superior and excellent herbicide have properties compared to 10 known herbicides, including homologous compounds of the most relevant prior art.

A primary aspect of the herbicidal compositions of the invention is their ability to control a wide variety of weeds, including weeds that are controllable by conventional herbicides and further a variety of weeds that have hitherto, individually and / or collectively, escaped control by a single class of known herbicides, while maintaining crop safety in one or more of a variety of crops including, in particular, soybeans, cotton, groundnuts, rapeseed and snap beans, as well as others. Although known herbicides are useful for controlling a variety of weeds, including occasionally certain resistant weeds, the unique herbicides of the invention have been shown to be capable of controlling or substantially suppressing a variety of resistant perennial and annual weeds, such as the perennial cultivated grass and yellow cyper grass, annual broadleaf plants, such as prickly sida, sesbania hemp, jimson herb, water pepper, loosestrife, Melganze foot and annual grasses, such as splinter reed, alexander grass, 30 seedling Johnston grass, Texas finger grass, wild proso millet, red rice, itch grass, and other noxious weeds, such as fall finger grass, needle spikes, cepa and digitaria. Improved weed control has also been accomplished in resistant weeds such as ragwort, room maple, ipomoea and burdock.

The compounds of the invention are characterized by formula 1 of the formula sheet, wherein R is ethyl, 8101 327% * - 6-n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl; R 1 is methyl, ethyl, n-propyl or isopropyl and R 1 is hydrogen, methyl or ethyl; provided that when R 1 is hydrogen, R 1 is ethyl, and R 1 is allyl; when R 2 is ethyl, R 1 is methyl and R is isopropyl; when R} is methyl, R is ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl; when R 1 is ethyl, R is sec-butyl, allyl or propargyl; when Rj is n-propyl, R is ethyl and when Rj is isopropyl, R is ethyl or n-propyl.

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

Further specific compounds according to the invention are: 2'-methoxy-6'-methyl-N- (ethoxymethyl-2) -2-chloroacetanilide, 2'-methoxy-6'-methyl-N- (1-sec-butoxy-methyl) -2-chloroacetanilide,> 2'-ethoxy-6'-methyl-N-iallyloxymethyl) -2-chloroacetanilide, 21-ethoxy-61-methyl-N- (propargyloxymethyl) -2-chloroacetanilide, 2'-ethoxy-N- (allyloxymethyl) -2-chloroacetanilide, 20 2'-methoxy-6'-ethyl-N- (isopropoxy-methyl-2) -2-chloroacetanilide, 2'-ethoxy-6'-methyl 1-N- (1-methylpropoxymethyl) - 2-chloroacetanilide, 2 * -n-propoxy-6 '-methyl 1-N- (ethoxymethyl) -2-chloroacetanilide, 2' -isopropoxy-6 '-methyl 1-N- (ethoxymethyl) -2-chloroacetani 1 ide and 2, -isopropoxy-6 * -methyl-N- (n-propoxymethyl) -2-chloroacetanilide.

The utility of the compounds of the invention as an active ingredient in herbicidal compositions formulated therewith and their mode of use will be described below.

The compounds of the invention can be prepared in a variety of ways. For example, these compounds can be prepared by the azomethine pathway described in U.S. Patents 3,442,945 and 3,547,620. According to the azomethine process, the appropriate primary aniline is reacted with formaldehyde to give the corresponding methylene aniline (substituted phenylazomethine) which is then reacted with a haloacetylating agent such as chlorine acetyl chloride. or chloroacetyl anhydride which in turn is reacted with the appropriate alcohol to yield the corresponding N-alkoxymethyl-2-chloroacetanilide as the final product.

Another procedure, which is described in more detail below, involves the transesterification of the appropriate N-methylene ether-2-haloacetanilide with the desired alcohol to obtain the corresponding re-etherified N-hydrocarbyl-methyl-2-haloacetanilide.

Yet another method of producing compounds of the invention involves N-alkylation of the anion of the appropriate secondary 2-haloacetanilide with an alkylating agent under basic conditions. The N-alkylation process is described in more detail in Examples XI to XIV below.

Example I

This example describes the preparation of a preferred compound, 2, -methoxy-6, -methyl-N- (isopropoxymethyl) -2-chloroacetanilide.

2 '-Methoxy-61-methyl-N- (methoxymethyl) -2-chloro-20-acetanilide (0.025 mol) in 100-150 ml of isopropanol containing about 0.02 mol of methanesulfonic acid was refluxed under a Soxhlet extraction device whose container contained activated 3A molecular sieve (25 g) to absorb the released methanol. The course of the reaction was followed by glc. Once the reaction was completed, the excess alcohol was removed in vacuo and the residue taken up in ether or chloroform. The solution was washed with 5% sodium carbonate solution, dried (Hg ^ SO ^) and evaporated. The product was purified by Kugelrohr distillation. Yield 55%; pale amber-30 colored solid, mp 40-41 ° C.

Anal .: Calculated for C 21 H 14 qCINO (%): C 58.84, H 7.05, N 4.90, Cl 12.41. Found: C 58.55, H 7.08, N 4.89 Cl 12.45.

The product was identified as described in the first paragraph of this example.

81 01 327 i \ - 8 -

Example II - IX

Following substantially the same procedures, amounts of reagents, and general conditions as described in Example 1, but substituting the appropriate alcohol to effect the omethe ring to obtain the final product, other N-hydrocarbyloxymethyl-2-haloacetanilides of the above formula were prepared ; these compounds are identified in Table Δ.

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Example X.

This example describes the preparation of the N- (methoxymethyl) -terterial anilide starting materials used to prepare the final products in Examples I to IX.

The N-methylene ether-substituted 2-chloroacetanilide starting materials used in Examples I to IX are prepared by alkylating the appropriate secondary 2-haloacetanilide by the N-alkylation process indicated above.

That process will be illustrated in this example with respect to JO for the preparation of the starting material in Example I.

2 * -methoxy-6 * -methyl-2-chloroacetanilide (0.025 mol), bromomethyl-methyl ether (0.05 mol) and benzyltriethyl ammonium bromide (2 g) were dissolved in methylene chloride (70 ml). Sodium hydroxide solution (40 ml 50%) was then added portionwise with stirring and cooling, keeping the temperature between 20 and 25 ° C. Once the addition was complete, the mixture was stirred for an additional 1.5 hours. Water (100 ml) was then added under cooling and the layers separated.

The methylene chloride layer was washed twice with 30 ml of saturated sodium chloride solution, dried (Mg2SO4) and evaporated. The residual product was crystallized or distilled under vacuum to obtain a yellow liquid, bp 140 ° C at 1.2 mm Hg.

Anal. Calculated for 2HggClNO ^ (%): 25 C 55.92, H 6.26, N 5.44

Found: C 56.35, H 6.33, N 5.36. The product was identified as 2 * -methoxy-61-methyl-N- (methoxymethyl) -2-chloroacetanilide.

Likewise, the starting N-methylene ether-30 substituted 2-chloroacetanilides of Examples II to IX were prepared by alkylating the corresponding secondary anilide with bromomethyl methyl ether; the 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-yer bond was prepared by chloroacetylation of the corresponding primary amine as follows: 2-methoxy-6-methylaniline (0 .03 mol) in methylene chloride (30 ml) was stirred vigorously with a 10% sodium hydroxide solution (0.05 mol) while a solution of chloro-5 acetyl chloride (0.033 mol) in methylene chloride (20 ml) was added keeping the temperature between 15 and 25 ° C with external cooling. The reaction mixture was stirred for an additional 30 minutes after the addition was complete, the layers were separated and the methylene chloride layer washed with water, dried and evaporated in vacuo. The product was crystallized from a suitable solvent to obtain white needles, m.p. 130-131 ° C.

Anal. Calculated for C 8 H 14 Cl 2 TC (%): C 56.21, Η 5.66, N 6.56, Cl 16.59. Found: C 56.16, Η 5.66, N 6.57, Cl 16.55 .

The product was identified as 2T-methoxy-6, -methyl-2-chloroacetanilide.

The secondary anilides used as starting materials in Examples II to IX were prepared in a similar manner.

The primary amines used to prepare the above secondary anilides can be prepared by known means, for example, by catalytic reduction of the corresponding substituted nitrobenzene in ethanol using platinum oxide catalyst.

As mentioned above, the products of the invention can also be prepared directly from the secondary anilide using the said N-alkylation process without first preparing the N-hydrocarbyloxymethyl intermediate (as described in Example X), which is then converted Ether to the final product as described in Example 1. Examples XI to XIV illustrate the preparation of compounds of the invention by said N-alkylation process.

Example XI

2-n-propoxy-6, -methyl-2-chloroacetanilide ·· -35 (4.35 g), chloromethyl ethyl ether, 3.4 g, benzyl triethyl ammonium chloride, (1.5 g) were mixed in 250 ml of methylene chloride and 8101327 - 13 - cooled. 50 ml of 50% NaOH at 15 ° C was added to the mixture and stirred for 2 minutes, then 100 ml of water was added. The layers were separated, washed with water, then dried over MgSO4 and evaporated. The product was purified by Kugelrohr distillation to obtain 4.8 g (89% yield) of a clear liquid, b.p. 130 ° C at 0.07 mm Hg.

Anal. Calculated for C 21 L CINO (%): 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-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide.

Example XII

2'-Isopropoxy-6'-methyl-2-chloroacetanilide, 5.55 g chloromethyl ethyl ether, 4.4 g benzyl triethyl ammonium chloride, 2.5 g in 250 ml methylene chloride and cooled to 0 ° C. 50 ml of 50% NaOH was suddenly added to the mixture, keeping the temperature below 15 ° C. The mixture was stirred for 2 hours, cooled, and then 100 ml of water was added. The layers were separated, washed with water, dried over MgSO 4 and evaporated to give 4.7 g (69% yield) of the product, a yellowish oil.

Anal .: Calculated for Cj ^ 22 ^^ 0 ^ (%): 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.

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

Example XIII

Following substantially the same procedure as described in Examples XI and XII, but using chloro-methylpropyl ether as an alkylating agent, 5.0 g (88% yield) of a yellow oil was obtained.

Anal .: Calculated for C 21 H 14 ClNO (%): C 61.24, H 7.73, 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-6-methyl-N- (n-propoxymethyl) -2-chloroacetanilide.

»» 8101327

, V

- 14 -

Example XIV

Following the same procedure as described in Examples XI to XIII but with substitution of the appropriate secanilide and halomethyl allyl ether, a yellow oil, boiling point 134 ° C / 0.08 mm Hg (Kugelrohr) was obtained.

Anal .: Calculated for C 8 H 9 ClNO 2 (%): 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- (allyloxy-10 methyl) -2-chloroacetanilide.

The herbicides of the invention have some. has been shown to have unexpectedly superior properties as pre-emergence herbicides, most particularly in the selective control of difficult-to-kill perennial and annuals, including perennial weeds such as cultivated grass and yellow cypergrass; annual broadleaf weeds such as prickly sida, sesbania hemp, jimson herb, water pepper, cat tails, melgan foot and annual grasses, such as seedling johnson grass, splinter reed, alexander grass (brachiaria plantaginea), 20 texas finger grass, red rice, wild proso millet, itch grass, coniferous spikes (e.g. green needle and giant needle), coot and Digitaria adscendens. Improved weed reduction in relation to the known acetanilides has also been achieved with other resistant species, such as ragwort, room-maple, ipomoea and burdock.

Selective control and increased suppression of the above weeds with the herbicides of the invention have been found in a variety of crops, including soybeans, cotton, groundnuts, rapeseed, and snap beans. Selectivity has been demonstrated in some tests in sugar beet, field maize, sweet wheat, barley and millet; however, these crops usually tolerate the herbicides of the invention less well than the above crops. It will be apparent to those skilled in the art that not all of the above weeds are selectively controlled by all of the compounds of the invention under all conditions of climate, soil type, moisture and / or manner of 8101327

i S

- 15 - herbicide application.

To illustrate the unexpectedly superior properties of the compounds of the invention both on an absolute and relative basis, comparative tests have been conducted in the greenhouse and in the open ground with: (1) prior art compounds which are most closely related in chemical structure to the compounds of the invention; (2) other homologues within the scope of said prior art which have superior herbicidal properties; and (3) commercial herbicidal compounds of a chemical structure generally related to those of the compounds of the invention. All compounds in the comparative tests below are generically described as substituted phenyl-N-alkoxy-alkyl-2-haloacetanilides. As used in the tables of data in the present specification, the compared compounds of the prior art are identified as follows: A. 2 '-methoxy-6'-tert-butyl-N- (methoxymethyl-2-chloroacetanilide) (Example 18, U.S. Patents 3,442,945 and 3,547,620).

B. 2T-methoxy-6'-tert-butyl-N- (methoxymethyl) -2-bromoacetanilide; (Example 34 of U.S. Patent 3,547,620 and Example 36 of U.S. Patent 3,442,945).

C. 2 ', 6'-diethy1-N- (methoxymethyl) -2-chloroacetanilide; (Example 5 of U.S. Pat. Nos. 3,547,620 and 3,442,945; this compound has the trivial name "alachlor" and is the active ingredient in the commercial herbicide LASSO, a brand name of Monsanto Company).

D. 2'-methyl-6'-ethyl-N- (ethoxymethyl) -2-chloroacetanilide; 30 (Example 53 in U.S. Pat. No. 3,547,620; common name "acetochlor").

E. 2, 6-dimethy1-N- (isopropoxymethyl) -2-chloroacetanilide; (Example 31 of U.S. Patent 3,547,620 and Example 33 of U.S. Patent 3,442,945).

35 8101327 TV t. "- 16 -

* -V

F. 2'-methoxy-6'-methyl-N- (methoxyethyl) -2-chloroacetanilide; (compound no. 6 in Belgian patent 810,763).

G. 21 -methoxy-6 * -methyl-N- (ethoxyethyl) -2-chloroacetanilide; (compound no. 7 in Belgian patent 810,763).

5 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 3,937,730; common name 10 "metochlor"; this compound is the active ingredient in the commercial herbicide "Dual", a brand name of Ciba-Geigy Corporation).

In emergence herbicidal trials, compounds of the invention were compared to prior art compounds A 15 to I in the control of various perennial and annual weeds, highlighting the difficult to kill species which are common infestations for important crops such as soybeans, cotton, groundnuts, rapeseed and string beans. The test results are shown below-20.

The discussion of data below reports herbicidal application amounts symbolized as "GR ^" and "GRg ^"; these quantities are given in kg per hectare. GRg defines the maximum amount of herbicide required to achieve 15% or less crop damage and GRg defines the minimum amount required to achieve 85% weed inhibition. GR1 and GR1 are used as a measure of potential commercial application, it being natural that suitable commercial herbicides may exhibit greater or lesser plant damage within reasonable limits.

A further guideline for the effectiveness of a chemical as a selective herbicide is the "selectivity factor" ("SF") for a herbicide in given crops and weeds. 35 The selectivity factor is a measure of the degree of crop safety and is expressed in terms of the ratio GR ^ / GRg ^, »8101327 - J7 - that is, the GRj ^ for the crop divided by the GRg, - for the weeds, both in kg / hectare. In the tables below, where used, selectivity factors are indicated in brackets after the weeds; the symbol "NS" indicates "non-selective"; 5 marginal or indeterminate selectivity is indicated by a hyphen (-) after the weeds and a blank space indicates that the plant species was not involved in a particular test, that the data was not obtained for any reason or was less significant than other available data, for example, some short term observations were omitted in favor of longer term data or longer term data were omitted because shorter term data provided information about a specific herbicidal activity.

Since crop tolerance and weed control are interrelated, a brief discussion of this relationship in terms of selectivity factors is meaningful. In general, it is desirable for crop tolerance values to be high since higher concentrations of herbicide are often desirable for some reason. Conversely, it is desirable for the weed control amounts to be low, that is, to have high unit activity, for economic and possibly environmental reasons.

However, small amounts of a herbicide may not be adequate for controlling certain weeds and a larger amount may be required. Therefore, the best herbicides are those that control the greatest number of weeds with the least amount of herbicide and provide the highest degree of crop safety, ie crop tolerance. Accordingly, "selectivity factors" (described above) are used to quantify the relationship between crop safety and weed control. With regard to the selectivity factors listed in the tables, the higher the numerical value, the greater the selectivity of the herbicide for weed control in a given crop.

The emergence tests referred to in the present description include both greenhouse and open field trials. In the greenhouse tests, the herbicide is applied either as a surface application after sowing or planting or by incorporation in an amount of soil for application over the test seeds in pre-sown test containers. In open field trials, the herbicide is incorporated into the soil ("PPI") prior to planting or sowing, ie the herbicide is applied to the surface of the soil, then incorporated therein by mixing means followed by sowing of the crop.

The surface application test method used in the greenhouse is carried out as follows: containers, for example aluminum pans with typical dimensions of 24.13 cm x 13.34 cm x 6.99 cm or plastic pots of 9.53 cm x 9.53 cm x 7.62 cm with water drainage holes in the bottom are filled to the brim with Ray sludge soil and then pressed to a level of 1.27 cm from the top of the pots. The pots are then sown with a plant species to be tested, then covered with a 1.27 cm thick layer of the test soil. The herbicide is then applied to the surface of the soil with a belt sprayer in the amount of 187 liters per hectare, at a pressure of 2.11 kg per cm; other nozzles, for example a DeVilbiss nozzle, are also useful on occasion. Each pot receives 0.64 cm of water for watering from above and the pots are then placed on greenhouse banks for subsequent sub-irrigation as needed. As an alternative procedure, the watering from above can be omitted. Observations of herbicidal effects are made approximately three weeks after treatment.

The herbicide treatment by soil incorporation used in greenhouse trials are as follows:

A good quality topsoil is applied in aluminum pans and pressed to a depth of 3 to 13 mm from the top of the pan. A number of seeds or plants of various plant species are placed on top of the ground. The soil required to fill the pans to the brim after sowing or planting is weighed in a pan. The soil and a known amount of the active ingredient applied in a solvent or as a wettable powder suspension are thoroughly mixed and used to cover the prepared pans. After treatment, the pans are initially watered from above with water equivalent to 0.64 rains, then watered by sub-irrigation as needed to provide good moisture for germination and growth. As an alternative procedure, the watering from above can be omitted. Observations are made under three weeks after sowing and treatment.

In a first series of tests, the herbicidal activity before emergence is shown in Table B, comparing the relative effectiveness of the compounds of the invention with that of relevant compounds of the prior art, against yellow cypergrass and culture grass in soybeans, cotton and corn.

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From the data in Table B it appears that in general the compounds according to the invention as a class are significantly more active, ie have a higher unit of activity, against both cyper grass and cultivated grass and exhibit greater crop safety in soybeans and cotton than the reference connections.

More specifically, with regard to the control of yellow cyper grass, it will be noted that each of the compounds of the invention tested was significantly more active against yellow cyper grass than compounds A and B, which are structurally closest related to the reference compounds, and compound H, which although less closely related than A and B can be considered more closely related in some respects to the compounds of the invention than compounds G, D, 15 E and I. More particularly, will be noted that the compound of Example 1, with a GRg ^ of 0.10 kg / ha, was approximately twice as active as the most active reference compound, compound E (GRg ^ of 0.37 kg / ha), while a crop safety factor has three times the compound E 20 in soybeans and equivalent safety in cotton. It will also be noted that the compounds of the invention of Examples II and XII also had equivalent and greater unit activity, respectively, than compound E against yellow cypergrass. In addition, although reference compounds F and G have reasonably high unit activity, neither of these compounds was selective against yellow cyper grass in soybeans, nor was compound F selective in cotton. Although Compound G did lead to selective control of cypergrass in cotton, the degree of safety was less than that for all compounds of the invention except Example II, and significantly less than that for Examples V, VI, and XIII. The selectivity factors of the compounds of Example IX and XIV against cypergrass in soybeans were particularly excellent.

Regarding culture grass control, the compound of Example II was substantially three times as active as the most active reference compound, Compound D, under 8101327-23 - maintaining equivalent crop safety in soybeans. The compound of the invention of Example III also had greater unit activity against cultivated grass and three times the soybean safety as compound D. Again, it will be noted that each compound of the invention tested against cultivated grass had excellent superior unit activity relative to compounds A and B, the most closely related reference compounds tested. Although the unit activity of compound H against culture grass was slightly higher than that for the compounds of Examples K and XIV, the selectivity factor for the latter compounds against culture grass in soybeans was about twice that of compound H, the next most related of the reference compounds. In addition, reference compounds A, B, F and G are non-selective against cultivated grass in soybean beans.

Further things to note in the data of Table B are that of all tested compounds, the compounds of Examples V, VI, IX, and XIV had the highest safety factors in soybeans compared to both yellow grass and culture grass. The compounds of Examples V, VI and XIII had by far the highest safety factors in cotton with respect to yellow cyper grass. Furthermore, it can be noted that the excellent crop safety factors of Examples V, VI, IX, XIII and XIV are accompanied by very low amounts of GRg2, indicating high unit activity against yellow cypergrass and cultivated grass. In these tests, most of the compounds of the invention were non-selective in maize like all but three of the reference compounds. However, the compound of Example XIV showed excellent superior selectivity to both culture grass and yellow cyper grass in corn.

In other comparative tests, the herbicidal activities of reference compounds C and D and of the compound of Example I were tested before emergence against various one-year broadleaf weeds at an application rate of 3.36 kg / ha. Observations took place six to seven weeks after treatment and the percentage of weed control was recorded - »* 8101327 - 24 -; the data from these tests is shown in Table C.

Table C

Control of annual broadleaf weeds 5 before emergence, 6-7 weeks after treatment_

Weed% control at 3.36 kg / ha connection

Example I C D

Spiky sida 93 35 73 10 Sesbania hemp 100 0 69

Melganze foot 83 62 88

Water pepper 88 64 76

Loosestrife 75 61 81

Ragwort 72 53 43 15 Jimson Herb 98 68 98

It is clear from the data in Table C that the compound of Example I exhibited excellent superior activity compared to Compound C against each of the tested one-year broadleaf weeds. Likewise, Compound 20 of Example I exhibited significantly superior activity compared to Compound D against prickly sida, sesbania hemp, water pepper and ragwort, and showed equivalent activity against Jimson spice, and slightly less unit activity against melgan foot and loosestrife.

In further comparative trials, field tests were conducted to determine the relative herbicidal emergence activities and crop selectivities of the compound of Example I compared to reference compounds C, D, E, and I, against coot, spiky sida, and sesbania hemp in 30 soybeans. These tests were performed in demarcated clay soil (Sharkey) pieces containing 2.0% organic matter and treated with various concentrations of each of the herbicides applied in the form of an emulsifiable concentrate in an application volume of 280.5 kg / ha. Observations were made 4 and 7 35 weeks after treatment. Based on three replications, the test data show that at the 7 week observation, the only compound 8101327-25 that selectively controlled sesbania hemp was the compound of Example I; this control (GRg ,.) was achieved at only 1.96 kg / ha, while the GRg for each of compounds C, E and I was 5.6 kg / ha and for compound D 5.0 kg / ha . The GR 2 ia soybeans were 3.9 kg / ha, resulting in a safety factor 2.0 for the compound of Example I. Thus, about three times as many of the reference compounds were required to produce GRg. achievable as required by the yer bond of Example I, but without selectivity in soybeans. Compounds C and D were non-selective against spiky sida jO in soybeans 7 weeks after treatment. Yerbinding I required 4.2 kg / ha and compound E 2.8 kg / ha to achieve GRg, and selectivity factors of 1.1 and 1.5, respectively. In contrast, the compound of Example 1 achieved GRg at only 0.8 kg / ha and a selectivity factor of 4.7 in soybeans.

Compounds C, D and E were nonselective against coot in soybeans 7 weeks after treatment. Compound I and the compound of Example X had substantially equivalent safety factors, i.e. 1.5 and 1.4, respectively.

The above open-field trials therefore show that, apart from comparable control of coot on compound I, the compound of Example I was significantly superior to the reference compounds C, D, E and I in the selective control of all three the annual weeds in soybeans 7 weeks after treatment.

In further trials to determine relative herbicidal activities and selectivities for even longer periods, the same herbicides used in the above trial were retested in open ground, this time in demarcated patches of soil from muddy clay to silky clay loam that 3.0 to 3.5% organic matter. In parallel runs, emulsifiable concentrates of the respective herbicides were applied to the surface and taken up before planting for pre-emergence control, again at 280.5 kg / ha, containing the appropriate concentration of herbicide as an active ingredient. In these tests, the herbicides were compared against the perennial weed cultivated grass and the annual broadleaf weeds 8101327-26 - weeds ragwort, melgan foot and water pepper in soy beans. These tests were exposed to heavy rainfall, the 4.45 cm on the 5 day after treatment and 2.29 cm, 1.52 cm, 1.27 cm and 1.27 cm of rain on subsequent days The test data are shown in Table D.

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The data in Table D shows that in the plant introduction tests none of the reference compounds selectively controlled any of the weeds tested in soybeans at rates up to 6.7 kg / ha, the maximum test-5 rate , at the observations after 6 weeks and after 9.5 weeks.

As indicated above, the selectivity is indicated by a selectivity factor, or the ratio GR1 / GRg1, of 1.0 or more; the greater the value, the greater the selectivity. In contrast, the compound of Example I showed selective control of culture grass, goosefoot and water pepper after 6.0 weeks and control of culture grass and water pepper after 9.5 weeks. The herbicidal activity of the compound of Example I appears to be of the order of 3 or more times that of the reference compounds against cultivated grass and goosefoot (except compound D) and about 2 or more times as active as the reference compounds (except compound D after 6 and 9.5 weeks and compound E after 9.5 weeks). None of the herbicides selectively controlled ragwort in this test, but the compound of Example I was more active against this weed than the reference 20 compounds at 6 weeks.

In the test data based on the application of the herbicides, it was again found that none of the reference compounds selectively controlled any of the weeds in the test in soybeans at rates of 6.7 kg / ha or less in the observations after 6 weeks or 9.5 weeks, except compound D in goose foot at the observation after 9.5 weeks. In these tests, selective weed control was observed for the compound of Example I in culture grass and water pepper after 6 weeks and in goosefoot after 9.5 weeks; the safety 30 factor here was slightly greater than that for compound D, namely 1.3 versus 1.1. Again, the compound of Example I showed much stronger herbicidal activity than the reference compounds in these tests.

The data in Table D shows that from the criteria of unit activity against weeds, the soybean tolerance to the herbicides, safety factors and modes of 8101327-30 herbicide application, the compound of Example I exhibited significantly superior properties as pre-emergence. herbicide, than the compared reference compounds.

The control of stubborn weeds exhibited by the compound of Example I under the heavy rainfall conditions as indicated above showed that the compound was not immediately leached.

In further open field comparative tests, the compounds of Example I and the reference J0 compounds D and E were tested for selective control of spiky sida and Digitaria in cotton on both surface and planting application; yellow cyper grass was included in the planting experiments. The soil in these experiments was mud with 1.7% organic matter. Observations occurred 2, 6 and 9 weeks after treatment. Based on three replications, data from the surface application tests showed that the compound of Example I had more than twice the unit activity against spiky sida as the compounds D and E after 6 weeks and 1.5 times its activity after 9 weeks. Compound D was non-selective against cotton spiky sida at 6 and 9 weeks. The selectivity factors for compound E at 6 and 9 weeks, respectively, were 1.1 and 1.2, compared to 3.3 and 1.8 for the compound of Example I. Although the unit activities for each of the compounds tested were similar against Digitaria at 6 weeks, the compound of Example I was more active than Compound E at 9 weeks and more selective (namely, a selectivity factor greater than 4.0) than Compound D with a selectivity factor of 2.8.

In the pre-planting introduction tests, after 9 weeks, the unit activity of the compound of Example I was more than twice that of the reference compounds against yellow cypergrass, slightly less than twice the unit activity of the reference compounds against Digitaria and more than 11/3 times the unit activity of the reference compounds 35 against spiky sida. In this open ground experiment, the compound of Example I selectively controlled yellow cyper grass in cotton 810132 7-3J - up to. 6 weeks after treatment, but the reference compounds showed no selectivity even at the 2 week observation. Although none of the test compounds selectively controlled spiky sida in this test prior to planting, the selectivity margin was much narrower for the compound of Example I than for the other compounds. The compound of Example I and Compound E just controlled Digitaria at 2 weeks of observation, but were non-selective thereafter; compound D was not selective against Digitaria on any of the observation 10 data.

Therefore, it can be concluded from the above experiments in open field cotton that the compound of Example I was much more active than the reference compounds against the yellow cypergrass and prickly sida weeds, while maintaining this activity for a longer period of time, and that the compound of Example I had superior selectivity factors with respect to these weeds. In addition, the compound of Example I had superior unit activity compared to Compound E and superior selectivity compared to Compound D against Digitaria in cotton after 9 weeks.

Further comparative tests between the compound of Example I and compounds D and E were conducted to determine their relative herbicidal activities and soil life against the remaining weeds yellow cyper grass and cultivated grass. Compounds D and E were among the most active selective herbicides of the 2-haloacetanilides of the prior art and have been considered class standards in tests for other herbaceous grasses and cultivated grasses and other weeds. In the experiments discussed here, two replicates of each treatment were planted with 25 tubers of yellow cyper grass and 25 rhizome fragments of culture grass. The herbicides were included in the soil coating in amounts sufficient to determine the GR10, i.e., the minimum amount (kg / ha) required to achieve 50% weed control; 35 11.2 kg / ha was the maximum and 1.4 kg / ha was the minimum actually applied. Observations took place after 3, 6, 12 and 18 *> 8101327 • * - 32 weeks. After each observation, the topcoat was removed from soil, the old tubers and rhizome fragments were removed and replanted and placed in the greenhouse for the subsequent cycle. Test results are shown in Table E.

5 Table E

Service life in soil GR50 (kg / ha)

Compound Yellow cypergrass. Cultivated grass. Soak after treatment. I <1.4 <1.4 3 <1.4 <1.4 6 1.4 1.4 12 8.4 11.2 18 D <1.4 <1.4 3 15 1.12 <1.4 6 5, 9 5.6 12> 11.2> 11.2 18 E <1.4 <1.4 3 1.4 1.7 6 20 7.8 11.2 12> 11.2> 11.2 18

The data for the control of yellow cypergrass in Table E shows that at 3 weeks post-treatment, the GR ^ q of each compound was less than 1.40 kg / ha with some clear differences occurring after 6 weeks. After 12 weeks, large differences in the control of yellow cyper grass were evident. Therefore, while only 1.40 kg / ha of the compound of Example I was required to control 50% of the weeds, 5.88 kg / ha of compound D and 7.84 kg / ha of compound E were required to control the same 30 achieve degree of control of yellow cypergrass. Furthermore, at 18 weeks after treatment, only 8.40 kg / ha of the compound of Example I was required for 50% cypergrass control, as opposed to an indefinite amount greater than. 11.2 kg / ha (the maximum amount used) of compounds D and E.

Likewise, the culture grass data in Table E show that at 6 weeks after treatment, the compound of Example I and Compound D had slightly better activity than Compound E.

81 01 327 - 33 -

However, at 12 weeks after treatment, the strong supremacy of the compound of Example I is evident: it requires only 1.40 kg / ha to achieve the same control of cultivated grass obtained by 5.60 kg / ha of compound D and 11 2.5 kg / ha of compound E. The superior herbicidal activity of the compound of Example I was also evident at 18 weeks after treatment.

A clear advantage of a herbicide is its ability to act in a wide variety of soil types. Therefore, in Table F, data is presented that shows the herbicidal effect of the compound of Example I on yellow cyper grass in cotton and soybeans in a wide variety of soil types of varying organic matter and clay content.

The herbicidal treatments were incorporated into the soil with the planted seeds at a depth of 0.95 cm, with a top watering of 0.64 cm. Observations took place 18 days after treatment.

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The data in Table F show that the compound of Example I is very insensitive to soil type and organic matter content, and exhibits selective control of yellow cyper grass in both cotton and soybeans in soils ranging from 1.0 to 6.8 X organic material and 1.8 to 9.6 X clay. The selectivity factors were greatest in Sarpy clay loam.

Further tests were conducted to determine the herbicidal behavior of the compound of Example I in soils containing a large amount of organic material. In three replicate field tests, the activity of the compound of Example I was tested against melange foot and soybean loosestrife planted in peat soil. Compounds C, D, E and I were also tested for comparison. These tests were performed with application by both pre-planting and surface application in peat soil containing 23 X organic material. In these experiments, the compound of Example 1, as much as the pre-planting uptake as the surface application, had the highest unit activity against loosestrife at 4 weeks after treatment and, prior to planting, showed the highest selectivity factor in soybeans, namely greater than 2.7 versus 1.1 for each of compounds C and D; compounds E and I were nonselective at 4 weeks after treatment. All compounds were non-selective against loosestrife at 7 weeks after treatment in both modes of herbicide application; compound E was slightly more active than the compound of Example I at 7 weeks after treatment in both modes of herbicide application. Against melgan foot, compound D had the highest unit activity and selectivity factor (1.9) at 7 weeks after treatment in both pre-planting and surface application; in the latter mode of administration, the selectivity factor of compound D was nearly twice as great as that of the compound of Example I and Compound E; no other compounds selectively controlled melgan foot at 7 weeks after treatment upon incorporation into the soil prior to planting or surface application. The connection of

example I (selectivity factor 2.0) and the compounds C and E

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8101 3 27 .. -36- (selectivity factor 1, Ö for both) selectively controlled melganzo foot at 4 weeks after treatment upon incorporation into the soil prior to planting.

The above tests therefore indicate that relative to the reference compounds in peat soil, the best selective control of loosestrife in soybeans is provided by the compound of Example I applied to the soil prior to planting; this compound had the highest unit activity and selectivity factor at 4 weeks after treatment of all compounds in the test. In addition, the compound of Example I selectively controlled melgan foot for up to about 7 weeks after treatment when applied to the surface and up to 4 weeks after treatment when administered by incorporation into the soil prior to planting. Compound D provided the best control of melganze foot at 7 weeks after treatment in both modes of administration. The relative behavior of the compound of Example I and compound D in peat soil should be further compared to the relative behavior of these two compounds in soils containing less organic matter, for example 3.0 to 3.5%, in which the compound of Example I exhibits superior unit activity and long soil life coupled with selectivity in soybeans both on surface application and pre-planting as shown in Table D.

The above description has emphasized the excellent herbicidal effectiveness of the compounds of the invention for controlling perennial and annual broadleaf weeds in soybeans and cotton. Furthermore, it has also been indicated and has been shown in some cases, for example in the tests relating to coot and Digitaria, that the compounds according to the invention also have excellent herbicidal activity against annual narrow-leaved weeds, ie grasses. In fact, as will be shown below with respect to certain annual grasses, compounds of the invention exhibit marked superiority over most herbicidally effective and / or commercially available 2. prior art haloacetanilides. As will be apparent from experimental data provided in the present specification, there are instances where a relevant 2-haloacetanilide of the prior art provides better herbicidal efficacy than the compounds of the invention with respect to specific annual weeds under similar conditions. However, it will also be apparent from the comparative test data provided in the present application that compounds of the invention are generally at least comparable to and often superior to, in some cases, far above the best 2-haloacetanilides as selective herbicides for controlling annual and perennial narrow-leaved weeds in soybeans, cotton, groundnuts and other crops.

In a greenhouse emergence test, the compounds of Examples I and XI were compared with the compounds C and I (both commercial 2-haloacetanilides) for their relative herbicidal effectiveness against annual narrow-leaved weeds, ie grasses in soybeans. In this experiment, the herbicides were incorporated into the soil prior to sowing and observations were made and recorded 17 days after treatment; the test data is shown in Table G and represents the means of duplicate runs.

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As for the data in Table G, important aspects to note are that: (I) Compound I showed the least unit activity and selectivity of all compounds against any weeds in the trial and showed no selectivity in soybeans with respect to wild proso- millet, red rice or itch grass; (2) compound C was as active as the most active of the compounds of Examples I and XI against splinter reed and wild proso millet; (3) the compounds of examples I and XI were both better than the prior art compounds against seedling Johnson grass and itch grass and (4) the compound of example XI was more active against alexander grass and the compound of example I was more active against red rice than the compounds of the prior art.

To summarize the comparative test data in Table G, one or both of the compounds of the invention were herbicidally as effective as the best prior art reference compound against two one-year-old narrow-leaf weeds (splinter reed and wild proso). millet) and clearly better against four narrow-leaved weeds (seedling-20 Johnson grass, alexander grass, red rice and itch grass). Particularly noteworthy is the excellent unit activity of the compound of Example I against seedling Johnson grass (GRg, - = 0.14 kg / ha), providing an excellent selectivity factor of about 8.0 in soybeans, compared to a selectivity factor greater than 2.0 for compound C, the best of the tested compounds of the prior art. Likewise, the compound of Example XI exhibited excellent unit activity against alexander grass and itch grass, providing selectivity factors of greater than 8.0 and greater than 4.0 in soybeans, respectively, compared to corresponding selectivity factors of greater than 4.0 and greater, respectively. than 1.0 for compound C.

Another trial was conducted in soybeans, this time the Texas and fall finger grass seeds were included along with the other one-year-old grasses mentioned in the previous test.

In this test, the compounds of Examples I and XII

8101327-40 - compared for herbicidal efficacy for emergence with the prior art compounds C, D and I. The herbicides were soaked up and irrigated from below as required. The maximum amount of herbicide used in the test was 1.12 kg / ha, hence the exact GRg,. And GRj. Values above 1.12 kg / ha are somewhat indeterminate. Site observations 2 weeks after treatment. The data from this test is shown in Table H.

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μ · · (U oo>>> 8101327 - 42 - "Analysis of the data in Table H shows that" the compounds of the invention of Examples I and XII showed the highest unit activities and selectivities of all compounds in the seedling assay -Johnson grass and splinter reed; the compound of example XII had the highest activity and selectivity against itch grass and the compounds of examples I and XII had in common the highest activities against wild proso millet with compound D and against autumn finger grass with each of the compounds of the prior art.

However, the compounds of the invention were more selective in soybeans than Compound D with respect to wild proso millet. In addition, the compound of Example XII was the second most active compound against Texas finger grass and red rice, and the compound of Example I shared second place in activity with compound D against itch grass. Compound D was the most active of the compounds tested against Texas finger grass, alexander grass and red rice.

It will therefore be apparent from the above comparative experimental data on herbicidal activity on annual grasses that compounds of the invention have herbicidal efficacy superior to that of the best relevant prior art compounds against certain annuals grasses, for example, coot, Digitaria (when incorporated into the soil), splinter reed and itch grass, and equivalent or generally comparable herbicidal effectiveness against others, for example digitaria (applied to the surface), the finger grasses, alexander grass and red rice.

Other tests in the greenhouse and / or in the open ground have shown selective control by compounds of the invention of further weeds in soybeans, cotton and / or other crops. For example, it has been shown that the compound of Example I selectively controls purple cypergrass and giant needle nature in cotton and giant needle needle and chamber maple in soybeans. Furthermore, it has been found that, compared to relevant prior art acetanilide herbicides, the compound of Example I has improved weed suppression against resistant weeds such as scabbard herb, ipomoea and burdock. Further weeds against which the compounds of the invention have been found to be herbicidally active include Canadian thistle, bindweed, fluffy swamp, wild buckwheat, etc.

As indicated above, compounds of the invention have proven to be effective herbicides in a variety of crops. The foregoing discussion and experimental data primarily focused on weed control in soybeans and cotton, crops of primary interest and utility in the present application. Additional tests have demonstrated the utility of compounds of the invention in other crops as explained below.

In a greenhouse test, the herbicidal effectiveness of the compounds of Examples XI and XII before emergence upon incorporation in the soil was tested against cultivated grass in rapeseed, broad beans, millet and wheat. Both of the compounds tested selectively controlled culture grass in oilseed rape and break beans, with the selectivity factor of the compound of Example XI being 3.5 in both crops and that of the compound of Example XII being 3.0 in both crops. In this test, both compounds were non-selective against culture grass in millet and wheat.

In separate greenhouse tests, the compound of Example I was also tested for its herbicidal effectiveness against yellow cyper grass and farm grass in rapeseed, groundnuts, sugar beet, millet, wheat and barley, respectively; the herbicide was applied by incorporation into the soil. In these experiments, compound D was included as a reference compound against cultivated grass and compound E as a reference compound against yellow cyper grass. Observations in the cultivated grass test were made 19 days after treatment and in the yellow cyper grass test 18 days after treatment; the test data are shown in Table K, selectivity factors for the herbicides are given in brackets after 35 g GR1 for the respective crops.

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The data in Table K shows that the compound of Example I and Compound D both controlled maize grass in groundnuts, rapeseed, sugar beet, wheat and barley, but the selectivity factor of the compound of Example I was significantly greater than that for compound D in groundnuts, rapeseed and sugar beet, equivalent in wheat and smaller in barley.

The compound of Example I selectively controlled yellow cypergrass in each crop in the test except sugar beets, while compound E did not selectively control yellow cypergrass in sugar beets, millet or wheat.

The high unit activity of the compounds D and E as shown in Table K is generally characteristic of the short-term (i.e. 2 to 6 weeks) behavior in the greenhouse for these compounds against cultivated grass and yellow cyper-grass. However, as shown here, all relevant test data, both in the greenhouse and in the open ground, demonstrate the uniformly superior unit activity against cultivated grass and cypress yellow grass and crop selectivity of the compound of Example I over compounds D and E over far longer periods. 20 den. In this connection, reference should again be made to: (1) Table D which contains comparative field trial data for periods up to 9.5 weeks for the behavior of these compounds against cultivated grass and other weeds in soybeans; (neither compound D nor E selectively controlled culture grass in soybeans even at observation three weeks after treatment); (2) the above discussion of the comparative field trial data for the behavior of these compounds against yellow cypergrass and other weeds in cotton for periods up to 9 weeks (neither compound D nor E controlled yellow cypergrass selectively in cotton even at observation 2 weeks after treatment) ; and (3) Table E which provides comparative soil life data for the compound of Example I and compounds D and E against yellow cyper grass and culture grass for 3, 6, 2 and 18 weeks, wherein the compound of Example I units of activity higher than that of compounds D and E 35 at 3 weeks post treatment (with magnitudes at observation at 12 weeks post treatment and with an indefinite amount at * »* 81 01 327 (

V

- 46 - observations at 18 weeks after treatment). It should also be noted here that the combined superior unit activity, soil life and crop selectivity of the compound of Example I over compounds D and E with respect to no cyper grass and farm grass is also applicable to the relative behavior of these compounds with respect to many other weeds, particularly seedling-Johnson grass, sesbania-hemp, prickly sida, water pepper, loosestrife, etc.

In a multi-crop and weed experiment, the emergence activity of the compound of Example I was further tested in open ground against certain annual weeds in various crops. In parallel tests, the herbicides were applied to the surface and incorporated into the soil before planting. Observations took place and were recorded 33 days after treatment for the soil incorporation test prior to planting and 34 days after treatment for the surface application tests. In both tests, the compound of Example 1 controlled coot and green needle selectively in corn, soybeans, cotton, climbing beans, and groundnuts; 20 loosestrife were also controlled in soybeans. Furthermore, in the soil incorporation test prior to planting, jack's paw and conifer were also selectively controlled in millet and sweet corn.

Thus, it will be apparent from the above detailed description that compounds of the invention have shown unexpected and far superior herbicidal properties both absolutely and relative to the structurally most relevant compounds, other related homologs and analogues and commercially available 2- halogenoacetanilides according to the prior art. More particularly, compounds of the invention have shown excellent unit activity, soil life and crop safety with respect to perennial and annual broadleaf and narrow-leaved weeds in soybeans, cotton, groundnuts, rapeseed and green beans and other crops. Even more particularly, compounds of the invention have demonstrated superior herbicidal activity against the remaining weeds yellow cyper grass and farm grass; annual broadleaf weeds, such as sesbania hemp, prickly sida, loosestrife and water pepper and annual narrowleaf weeds such as coot, Digitaria (inclusion in the soil prior to planting), splinter reed and itch grass. In addition, compounds of the invention have been found to be generally comparable to the best of the compounds of the relevant prior art in the control of other annual grass weeds, such as seedling Johnson grass, Digitaria (surface application), needle spikes , Texas finger grass, fall finger grass, wild proso millet, alexander grass and red rice and annual broadleaf weeds such as melgan foot and jimson weed. Finally, compounds of the invention have also shown increased activity and suppression of resistant one-year-old broadleaf weeds such as ipomoea, burdock, ragwort, and camellia.

Toxicological studies of the compound of Example I have shown that the compound is very safe. She was mildly toxic by internal use (single dose OLD ^ q: 2600 20 mg / kg), mildly toxic by single skin contact (DLDj-q: 5010 mg / kg), and slightly irritating to the eye and skin . No special handling procedures other than normal precautions are considered necessary.

The herbicidal compositions of the invention, including concentrates that require dilution before use, contain at least one active ingredient and an additive in liquid or solid form. The compositions are obtained by mixing the active ingredient with an additive, comprising diluents, extenders, carriers and conditioners to provide preparations in the form of finely divided particulate solids, granules, pellets, solutions, dispersions or emulsions. For example, the active ingredient can be used with an additive such as a particulate solid, an organic liquid, water, a wetting agent, a dispersant, an emulsifying agent, or any suitable combination thereof.

8101 32 7 - 48 - *,

The compositions according to the invention, in particular liquids and wettable powders, preferably contain as conditioner one or more surfactants in amounts sufficient to make a given composition easily dispersible in water or in oil. The inclusion of a surfactant in the compositions greatly enhances their effectiveness. The term "surfactant" includes wetting agents, dispersants, suspending agents and emulsifying agents. Anionic, cationic and non-ionic agents can be used with equal ease.

Preferred humectants are alkylbenzene and alkylnaphthalene sulfonates, sulfated fatty alcohols, amines or acid amides, long chain acid esters of sodium isothionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid oils, sulfonated sulfonylsulfonyl sulfonylsulfonyl sulfonylsulfonyl sulfonylsulfonyl sulfonates polyoxyethylene derivatives of alkylphenols (especially isoctylphenol and nonylphenol) and polyoxyethylene derivatives of the mono-higher fatty acid esters of hexitol anhydrides (e.g. sorbitan). Preferred dispersants are methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymer alkyl, naphthalene sulfonates, sodium naphthalene sulfonate, and the polymethylene bisnaphthalene sulfonate.

Wettable powders are water-dispersible preparations containing one or more active ingredients, an inert solid extenders and one or more wetting and dispersing agents. The inert solid extenders are usually of mineral origin, such as the natural clays, diatomaceous earth and synthetic minerals derived from silicon dioxide and the like. Examples of such extenders include kaolin staples, attapulgite clay, and synthetic magnesium silicate. The wettable powder compositions of the invention usually contain about 0.5 to 60 parts (preferably 5 to 20 parts) of active ingredient, about 0.25 to 25 parts (preferably 1 to 35 parts) of wetting agent, about 0.25 to 25 parts (preferably 1.0 to 15 parts) of dispersant and 5 to about 95 parts (10 to 50 parts) of inert solid extender, preferably all parts by weight, based on the total composition.

If required, about 0.1 to 2.0 parts of the solid inert extender can be replaced by an anti-corrosion inhibitor or anti-foaming agent or both.

Other formulations include dust concentrates that comprise 0.1 to 60% by weight of the active ingredient on a suitable extender; these dusty materials can be diluted for use at concentrations within the range of about 0.1 to 10% by weight.

Aqueous suspensions or emulsions can be prepared by stirring an aqueous mixture of a water-insoluble active ingredient and an emulsifying agent until uniformity is achieved and then homogenizing to provide a stable emulsion of very finely divided particles. The resulting concentrated aqueous suspension is characterized by its extremely small particle size, so that the coating is very uniform upon dilution and spraying. Suitable concentrations of these preparations contain about 0.1 to 60 and preferably 5 to 50% by weight of the active ingredient, the upper limit being determined by the solubility limit of the active ingredient in the solvent.

In another form of aqueous suspensions, a water-immiscible herbicide is encapsulated to form a micro-encapsulated phase dispersed in an aqueous phase.

In one embodiment, minute capsules are formed by bringing together an aqueous phase containing a lignin sulfonate emulsifier and a water-immiscible chemical and polymethylene-30-polyphenyl isocyanate, the water-immiscible phase being dispersed in the aqueous phase followed by the addition of a polyfunctional amine. The isocyanate and amine compounds react to form a solid urea shell wall around particles of the water-immiscible chemical to form microcapsules therefrom. Generally, the concentration of microcapsulated material 8101 32 7x - 50 - will range from about 480 to 700 g / l, preferably 480 to 600 g / l, of the total composition.

Concentrates are usually solutions of active ingredient in water-immiscible or partially miscible solvents together with a surfactant. Suitable solvents for the active ingredient of the invention include dimethylformamide, dimethyl sulfoxide, N-methyl pyrrolidone, hydrocarbons and water immiscible ethers, esters or ketones. However, other high strength liquid concentrates can be formulated by dissolving the active ingredient in a solvent and then diluting it, eg with kerosene, to spray concentration.

The present concentrate preparations generally contain about 0.1 to 95, preferably 5 to 60 parts of active ingredient, about 0.25 to 50 parts, preferably 1 to 25 parts of surfactant and, if necessary, about 4 to 94 parts solvent, where all parts are parts by weight based on the total weight of the emulsifiable oil.

Granules are physically stable particulate preparations comprising active ingredient adhered to or distributed by a base matrix of an inert particulate particulate extender. To help leach the active ingredient from the particulate material, a surfactant, such as the aforementioned surfactants, may be present in the composition. Natural clays, pyrophilites, illite and vermieulite are examples of useful classes of particulate mineral extenders. Preferred extenders are the porous, absorbent, preformed particles, such as preformed and sieved particulate attapulgite or heat-expanded particulate verminulite and finely divided clays, such as kaolin clays, hydrated attapulgite or bentonite clays. These extenders are sprayed or mixed with the active ingredient to form the herbicidal granules.

The granular preparations according to the invention can contain from about 0.2 to about 30, preferably from about 3 to 8101 327 -51-20 parts by weight of active ingredient per 100 parts by weight of clay and from 0 to about 5 parts by weight of surfactant. per 100 parts by weight of particulate clay.

The compositions of the invention may also contain other additives, for example, fertilizers, other herbicides, other pesticides, safeners and the like used as additives or in combination with any of the additives described above. Chemicals useful in combination with the active ingredients of the invention include, for example, triazines, ureas, carbamates, acetamides, acetal anilides, uracils, acetic or phenol derivatives, thiol carbamates, triazoles, benzoic acids, nitriles, biphenyl ethers and the like, such as :

Heterocyclic nitrogen / sulfur derivatives 15 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 20 6,7-dihydrodipyrido (1 2-a: 2 *, 1'-c) -pyrazidinium salt 5-bromo-3-isopropyl-6-methyluracil 1,1'-dimethyl. 4'-Bipyridinium Ureas N * - (4-chlorophenoxy) -phenyl-N, N-dimethylurea 25 Ν, Ν-dimethy1-N '- (3-chloro-4-methylphenyl) -urea 3- (3,4- dichlorophenyl) -1,1-dimethyl urea 1,3-dimethyl 1-3- (2-benzothiazoly1) urea 3- (p-chlorophenyl) -1,1-dimethyl urea 1-butyl-3- (3,4-dichlorophenyl) - 1-methyl urea 30 Carbamates / thiol carbamates 2-chloroallyl-diethyl dithiocarbamate S- (4-chlorobenzyl) -Ν, Ν-diethylthiolcarbamate Isopropyl-N- (3-chlorophenyl) -carbamate S-2,3-dichloro-allyl-N, N-di-di-carbyl ethy1-N, N-dipropy1thiol carbamate S-propyl dipropylthiol carbamate 810132 7 r * • ..

- 52 -

Acetamides / acetanilides / anilines / amides 2-chloro-N, N-diallylacetamide N, N-dimethyl-2,2-diphenylacetamide N- (2,4-dimethyl-5- / / (trifluoromethyl) sulfonyl-7-amino-5-phenyl) acetamide N -isopropy1-2-chloroacetanilide 2 ', 6'-diethyl-N-methoxymethyl-2-chloroacetanilide 2'-methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide α, α, α-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluxdine 10 N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide

Acids / Esters / Alcohols 2,2-dichloropropionic acid 2-methyl-4-chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid 15 Methyl 2- / 4- (2,4-dichlorophenoxy) phenoxy / propionate 3-amino-2,5-dichlorobenzoic acid 2 -methoxy-3,6-dichlorobenzoic acid 2,3,6-trichlorophenylacetic acid N-1-naphthylphthalamic acid

Sodium 5- / 2-chloro-4- (trifluoromethyl) phenoxy / 2-nitrobenzoate 4.6-dinitro-o-sec-butylphenol

Nr (phosphonomethyl) glycine and its C._g monoalkylamine and alkali metal salts and combinations thereof

Ethers 2,4-dichlorophenyl-4-nitrophenyl ether 25 2-chloro-a, a, oi-trifluoro-p-tolyl-3-ethoxy-4-nitrodiphenyl ether Miscellaneous 2,6-dichlorobenzonitrile Monosodium acid methane arsonate 30 "Disodium methane arsonate

Fertilizers useful in combination with the active ingredients include, for example, ammonium nitrate, urea, potassium carbonate and superphosphate. Other useful additives include materials in which plant organisms root and grow, such as compost, farmyard manure, humus, sand and the like.

Examples of herbicidal preparations of the types described above are given below in various illustrative embodiments.

I. Emulsifiable concentrates

Wt% A. Compound of Example I 50.0 Calcium dodecylbenzenesulfonate / polyoxyethylene ethers mixture (eg, Atlox (S) 3437F and Atlox 3438F) 5.0

Monochlorobenzene 45.0 100.00 10 B. Compound of Example XIX 85.0

Calcium dodecyl sulfonate / alkyl aryl polyether alcohol mixture 4.0 C-aromatic hydrocarbon solvent 11.0 15 100.00 C. Compound of Example XIII 5.0

Calcium-dodecylbenzene sulfonate / polyoxyethylene ethers mixture (e.g., Atlox 3437F) 1.0 20 Xylene 94.0 100.00 II. Liquid concentrates

Wt% A. Compound of Example I 10.0 Xylene 90.0 100.00 B. Compound of Example II 85.0

Dimethyl sulfoxide 15.0 100.00 30 C. Compound of Example III 50.0 N-methylpyrrolidone 50.0 100.00 D. Compound of Example IV 5.0

Ethoxylated Castor Oil 20.0 35 Rhodamine B 0.5

Dimethylformamide 74.5 100.00 8101327 - 54 - III. Emulsions

Wt% A. Compound of Example I 40.0

Polyoxyethylene / polyoxypropylene-5 block copolymer with butanol (e.g.

Tergitol®XH) 4.0

Water 56.0 100.00 10 B. Compound of Example V 5.0

Polyoxyethylene / polyoxypropylene block copolymer with butanol 3.5

Water 91.5 100.0 15 IV. Wettable powders

Wt% A. Compound of Example I 25.0

Sodium lignosulfonate 3.0

Sodium N-methyl-N-oleyl taurate 1.0 20 Amorphous silica (synthetic) 71.0 100.00 B. Compound of Example VI 80.0

Sodium dioctyl sulfosuccinate 1.25 Calcium lignosulfonate 2.75

Amorphous silica (synthetic) 16.00 100.00 C. Compound of Example VII 10.0 Sodium lignosulfonate 3.0

Sodium N-methyl-N-oleyl taurate 1.0

Kaolinite clay 86.0 100.00 35 ** 81 01 327 - 55 - V. Fabrics

Wt% A. Compound of Example I 2.0

Attapulgite 98.0 5 100.00 B. Compound of Example VIII 60.0

Montmorillonite 40.0 100.0 10 C. Compound of Example IX 30.0

Bentonite 70.0 100.00 D. Yer bond of Example XI 1.0

Diatomaceous earth 99.0 100.00 VI, Granules

Wt% 20 A. Compound of Example I 15.0

Granular attapulgite (20/40 mesh) 85.0 100.00 B. Compound of example XII 30.0 25 Diatomaceous earth (20/40) 70.0 100.00 C. Compound of example XIII 0.5

Bentonite (20/40) 99.5 30 100.00 D. Compound of Example XIV 5.0

Pyrophyllite (20/40) 95.0 100.00 35 8101327 '' - 56 - VII. Microcapsules

Wt% A. Compound of Example I encapsulated in polyurea shell 49.2 Sodium lignosulfonate (eg Reax 88 (r) b) 0.9

Water 49.9 100.00 B. Compound of Example XII encapsulated 10 in polyurea shell 10.0

Potassium lignosulfonate (eg Reax (§) c-21) 0.5

Water · 89.5 100.00 C. Compound of Example XIII encapsulated in polyurea shell 80.0

Magnesium salt of lignosulfate (Treax (f) LTM) 2.0

Water 18.0 20 100.00

When used in accordance with the present invention, effective amounts of the acetanilides of the invention are administered to the soil containing the plants, or incorporated into aqueous media in any suitable manner. The application of liquid and particulate solid preparations to the soil can be carried out by conventional methods, for example power sprays, machine and hand sprayers and spray sprays. The compositions can also be administered from airplanes in the form of dust or nylon due to their effectiveness in small doses. The administration of herbicidal preparations to aquatic plants is usually performed by adding the preparations to the aqueous environments in the area where control of the aquatic plants is desired.

The administration of an effective amount of the compounds of the invention to a growth site 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, including the plant species and their stage of development, the type and condition of the soil, the amount of rainfall and the specific acetanilide used. When applied selectively for emergence to the plants or to the soil, a dose of from 0.02 to about 11.2 kg / ha, preferably from about 0.04 to about 5.60 kg / ha, or suitably from 1.12 to 5.6 kg / ha of acetanilide are used. Lower or higher amounts may be needed in some cases. The skilled artisan can easily deduce from the present disclosure, including the above example, the optimal amount to be administered in a particular case.

The term "soil" or soil (soil) is used in its broadest sense and includes all conventional soil types as defined under "soil" in Webster's New International Dictionary, Second Edition, Unabridged (1961). The term therefore refers to any substance or medium in which plants can root and grow and includes not only soil but also compost, manure, peat or peat, humus, sand and the like, suitable for supporting plant growth.

Although the invention has been described with respect to specific modifications, the details thereof should not be construed as limitations.

25 * # * 8101327

Claims (47)

Compounds of formula 1, wherein R is ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl; Rj is methyl, ethyl, n-propyl or isopropyl and R 2 is hydrogen, methyl or ethyl, provided that when R 2 is hydrogen, R 1 is ethyl and R 1 is allyl; when R 2 is ethyl, R 1 is methyl and R is isopropyl; when R 1 is methyl, R is ethyl, isopropyl, isobutyl, sec-butyl, or cyclopropylmethyl; when R 1 is ethyl, R is sec-butyl, allyl or propargyl; When Rj is n-propyl, R is ethyl and when Rj is isopropyl, R is ethyl or n-propyl. The compound of claim 1, 2'-methoxy-6'-methyl-N- (isopropoxymethyl) -2-chloroacetanilide. The compound of claim 3,15 2'-methyl-6'-methyl-1-N- (ethoxymethyl) -2-chloroacetanilide. The compound of claim 1, 2 '-methoxy-6' -methyl 1-N- (1-methylpropoxymethyl) -2-chloroacetanilide. The compound of claim 3, 2'-ethoxy-6'-methyl-N- (allyloxymethyl) -2-chloroacetanilide. The compound of claim 1, 2'-ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide. 7. The compound of claim J, 2 '-ethoxy-6' -methyl 1-N- (3-methylpropoxymethyl) -2-chloroacetanilide. The compound according to claim 1, 2 '-n-propoxy-6' -methyl 1-N- (ethoxymethyl) -2-chloroacetanilide. 9. The compound of claim 3, 2 '-isopropoxy-6' -methyl-1-N- (ethoxymethyl) -2-chloroacetanilide. The compound of claim 3, 2 '-isopropoxy-6' -methyl 1-N- (n-propoxymethyl 1) -2-chloroacetanilide. The compound of claim 3,35 2'-ethoxy-N- (allyloxymethyl) -2-chloroacetanilide. The compound of claim 3,8101327 4. - 59 - fe 2'-methoxy-6'-ethyl-N- (isopropoxy methyl1) -2-chloroacetanilide. Herbicidal compositions comprising a herbicidal compound and an additive, characterized in that the herbicidal compound is a compound of formula 1, wherein 5. ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropyl-methyl, allyl or propargyl; R 1 is methyl, ethyl, n-propyl or isopropyl and R 2 is hydrogen, methyl or ethyl, provided that when R 2 is hydrogen, R 1 is ethyl and R is allyl; when R 2 is ethyl, R 1 is methyl and R is isopropyl; when R 10 is methyl, R is ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl; when R 1 is ethyl, R is sec-butyl, allyl or propargyl; when Rj is n-propyl, R is ethyl and when Rj is isopropyl, R is ethyl or n-propyl. 14. A composition according to claim 13, characterized in that the compound is 2'-methoxy-6'-methyl-N- (isopropoxymethyl) -2-chloroacetanilide. Preparation according to claim 13, characterized in that the compound is 2'-methoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. Preparation according to claim 13, characterized in that the compound is 2'-methoxy-6'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. 17. The composition according to claim 13, characterized in that the compound is 2'-ethoxy-6'-methyl-N- (allyloxymethyl) -2-chloroacetanilide. Preparation according to claim 13, characterized in that the compound is 2 * -ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide. 19. A composition according to claim 13, characterized in that the compound is 2'-ethoxy-6 '-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. Preparation according to claim 13, characterized in that the compound is 2'-n-propoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 23. A composition according to claim 13, characterized in that the compound is 2'-isopropoxy-6'-methyl-N- (ethoxymethyl) -2-8101 327-60 -A chloroacetanilide. Preparation according to claim 13, characterized in that the compound is 2'-isopropoxy-6'-methyl-N- (n-propoxy-methyl) -2-chloroacetanilide. The preparation according to claim 13, characterized in that the compound is 2'-ethoxy-N- (allyloxymethyl) -2-chloroacetanilide. 24. A composition according to claim 13, characterized in that the compound is 2 * -methoxy-6, -ethyl-N- (isopropoxymethyl) -10 2-chloroacetanilide. Method for controlling unwanted plants growing in useful crops, characterized in that a herbicidally effective amount of a compound of formula 1, wherein R is ethyl, n-propyl, isopropyl, is applied to the growing site of said plants isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl; R 1 is methyl, ethyl, n-propyl or isopropyl and R 2 is hydrogen, methyl or ethyl, provided that when R 2 is hydrogen, R 1 is ethyl and R is allyl; when R 2 is ethyl, R 1 is methyl, and R is isopropyl; when R 1 is methyl, R is ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl; when R-j is ethyl, R is sec-butyl, allyl or propargyl; when R 1 is n-propyl, R is ethyl and when R 1 is isopropyl, R is ethyl or n-propyl. 26. Process according to claim 25, characterized in that the compound is 2, -methoxy-6, -methyl-N- (isopropoxymethyl) -2-chloroacetanilide. A method according to claim 25, characterized in that the compound is 2, -methoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 28. Process according to claim 25, characterized in that the compound is 2, -methoxy-6, -methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. 29. Process according to claim 25, characterized in that the compound is 2'-ethoxy-6T-methyl-N- (allyloxymethyl) -35-chloroacetanil. 30. Process according to claim 25, characterized in that the compound is 2 * -ethoxy-6'-methyl-N- (propargyloxy-methyl) -2-chloroacetanilide. 31. Process according to claim 25, characterized in that the compound is 2'-ethoxy-6'-methyl-N- (1-methylpropoxy-methyl) -2-chloroacetanilide. The process according to claim 25, characterized in that the compound is 2'-n-propoxy-6 r-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 33. Process according to claim 25, characterized in that the compound is 2, -isopropoxy-6, -methyl-N- (ethoxymethyl) -2-chloroacetanilide. 34. A process according to claim 25, characterized in that the compound is 2, -ethoxy-N- (allyloxymethyl) -2-chloroacetanilide. A method according to claim 25, characterized in that the compound is 2'-methoxy-6T-ethyl-N- (isopropoxymethyl) -2-chloroacetanilide. 36. A method according to claim 25, characterized in that the useful crop is soybeans, cotton, groundnuts, rapeseed, climbing beans, sugar beet, millet, wheat or barley. A method according to claim 36, characterized in that the unwanted plants are perennial grass and sedge weeds and annuals. 38. A method according to claim 37, characterized in that the remaining weeds are cultivated grass and yellow cyper grass. A method according to claim 37, characterized in that the annual weeds are broad-leaved weeds. 40. A method according to claim 39, characterized in that the broadleaf weeds are prickly sida, sesbania hemp, goosefoot, water pepper, loosestrife and jimson weed, A method according to claim 37, characterized in that the annual weeds are grasses. A method according to claim 41, characterized in that the grasses are needle spikes, coot, Digitaria, finger grasses, splinter reed, alexander grass, red rice and itch grass. 81 01 327 A method according to any one of claims 36-41, or 42, characterized in that the compound is 2, -methoxy-6, "methyl-N- (isopropoxymethyl) -2-chloroacetanilide. 44. A method for selectively controlling the growth of weeds in soybeans, cotton, groundnuts, rapeseed, green beans, sugar beets, millet, wheat or barley, characterized in that a herbicidal is grown on the growing site of said weeds effective amount of 2'-methoxy-6'-methyl-N- (isopropoxy-methyl) -2-chloroacetanilide. 45. A method for suppressing weed stocks of ragwort, ipomoea, burdock and room maple, characterized in that a herbicidally effective amount of 2'-methoxy-6, -methyl-N- (isopropoxymethyl) -2 is added at its growth site -chloroacetanilide. 46. Methods and articles essentially as described in the description and / or the examples. r '-.................................. / / 81013 2 7 U r, A -.ut. 0 CtCHC CHOR 1/1 N * R. 0R1 KqT 8101327 MONSANTO COMPANY, St. Louis, Missouri, USA America