LU83235A1 - N-ALCOXYMETHYL-2-HALOACETANILIDES COMPOUNDS AND HERBICIDE COMPOSITIONS CONTAINING THESE COMPOUNDS AS ACTIVE INGREDIENTS - Google Patents

Description

ί’Υ'λ / - ΙλλλΑ t 1.

The present invention relates to the field of T-2-haloacetanilides and to their use in agricultural techniques, for example as herbicides.

The prior art relating to the present invention includes numerous descriptions of 2-haloacetanilides which may be unsubstituted or substituted with a large number of substituents on the anilide nitrogen atom and on the anilide nucleus , comprising alkyl, alkoxy, alkoxyalkyl, halogen, etc. radicals

As an interesting technique for the compounds of the present invention, which are characterized by the fact that they have an alkoxymethyl or alkenyloxymethyl radical on the anilide nitrogen, an alkoxy or alkenyloxy radical in an ortho position and from hydrogen or a specific alkyl radical in the other ortho position, the closest prior art known to the applicant is represented by US Pat. Nos. 3,442,945 and 3,547,620. The most interesting descriptions in US Pat. Nos. 3,442,945 and 3,547,620 are the compounds 2'-20 t-butyl-2-chloro-N-methoxymethyl-6'-methoxyacetanilide and its brominated analogue (examples 18 and 34 of US Patent No. 3,547,620 and Examples 18 and 36 of US Patent No. 3,442,945, respectively.

U.S. Patents 4,040,389 and 4,152,137 * 2.

describe a generic formula which includes compounds of the type described in US Pat. Nos. 3,442,945 and 3,547,620. However, the only compound of the species described having an alkyl radical in an ortho position and an alkoxy radical in the other ortho position has an alkoxy-ethyl radical on the anilide nitrogen atom; compounds of this type are indicated in more detail below.

Other less interesting prior art documents are: Belgian Patent No. 810,763 and published German patent application No. 2,402,983; the compounds of these references include compounds of the type described in US Pat. .389 and No. 4.152.137 and are characterized in that they have an alkoxyalkyl radical having v 2 (or more) carbon atoms between the nitrogen atom of anilide and the oxygen atom of the alkoxy part. The most interesting specific descriptions in Belgian Patent No. 810,763 and in published German Patent Application No. 2,402,983 appear to be compounds having an ethoxyethyl radical on the anilide nitrogen atom, a 2o radical methoxy or ethoxy in one ortho position and a methyl or isopropyl radical in the other ortho position. With reference to Belgian Patent No. 810,763, reference will be made to compounds No. 7, 16 and 18; other less interesting counterparts of these compounds are also described, for example compounds 6, 9 and 17, which have methoxyethyl or methoxypropyl radicals substituted on the nitrogen atom, a methoxy or ethoxy radical in a position ortho and a methyl radical in the other ortho position.

U.S. Patent No. 3,442,945 cited above, which describes the above-mentioned compounds having a chemical configuration most closely related to the compounds of the present invention, contains certain herbicidal results, therefore, and certain results are presented for other homologous compounds and analogues less closely related from the point of view of chemical structure. Similarly, certain results are presented for compounds no. 6 and 9 in Belgian patent no. 810,763. More particularly, these most interesting references, while describing a herbicidal activity on a large number of weeds, do not provide results for compounds which are shown to control in addition and / or εις simultaneously the narrow-leaved weeds, difficult to control, which consist of young Johnson grass plants and / or brittle cane both belonging to the same genus of plant as sorghum, and other difficult weeds destroy, such as anseri -] _ q with red root and wild prosomillet, in addition to less resistant weeds such as yellow fox tail, backyard grass and wild grass, while maintaining safety for sorghum. Belgian Patent No. 810,763 presents results showing that compound # 6 destroys sorghum, while no results are presented for the effect of compound # 9 on sorghum. As will be shown here, the novel compounds of the present invention possess unexpectedly superior properties as selective herbicides in sorghum, compared to homo-2o compounds of the prior art.

It is an object of the present invention to provide herbicides which selectively control weeds which are difficult to control or destroy, such as young Johnson grass plants and / or cane brittle and, for certain species of the present invention, other hard-to-kill weeds such as red root an-serine and wild prosomillet, in addition to less resistant weeds such as yellow fox tail, bass grass -cour and wild grass, particularly in sorghum, in a manner superior to that of the prior art.

The objects indicated above and other objects of the present invention will become more apparent from the detailed description below.

The present invention relates to compounds with herbicidal activity, to herbicidal compositions containing these compounds as active ingredients and to the herbal process.

bicide of use of these compounds in particular crops to harvest, especially sorghum.

The Applicant has now found that a selective group of 2-haloacetanilides, characterized by specific alkoxymethyl or alkenyloxymethyl radiols on the anilide nitrogen atom, specific alkoxy radicals in an ortho position and hydrogen or the methyl radical in the other ortho position, possesses remarkable selective and superior herbicidal properties unexpectedly as herbicides for sorghum, with respect to herbicides of the prior art, comprising compounds homologous to the prior art more interesting.

A main characteristic of the herbicide compositions of the present invention is their ability to selectively control narrow-leaved weeds consisting of young Johnson grass plants and / or brittle cane which are species of the same species. kind of plant than sorghum; in fact, both sorghum and brittle cane are of the species sorghum bicolor. As a result, it is excessively difficult to selectively control brittle cane and young Johnson grass plants in sorghum without simultaneously damaging the sorghum. In addition, some members of the compounds of the present invention also control or destroy other hard-to-destroy species, such as red-rooted anserine, walnut yellow sedge or white prosomillet, and all compounds of the present invention control or destroy other species such as yellow fox tail, backyard grass, wild grass and other noxious weeds.

The compounds of the present invention are characterized by the formula: 0 * Il cich9c ch9or 35 5.

where R is isopropyl, n-butyl, isobutyl, sec-buty-le, allyl or 2-methylbutyl; is methyl, isopropyl, n-butyl or allyl and 5 * 2 e * - ^ 3 are hydrogen or methyl as seen; 1 * 1 # R2 and each is methyl when R is n-butyl, isobutyl or sec-butyl; R2 and are each hydrogen when R is isopropyl, isobutyl or sec-butyl and R ^ is isopropyl or n-butyl, and R2 is hydrogen and R ^ methyl when R is 2-methylbutyl or allyl group and that R ^ is the allyl group.

Preferred species of compounds of the present invention are: N- (isobutoxymethyl) -2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanilide, N- (n-butoxymethyl) -2'-methoxy- 3 ', 6'-dimethyl-2-20 chloroacetanilide, N- (sec-butoxymethyl) -2'-methoxy-3', 6'-dimethyl-2-chloroacetanilide, N- (allyloxymethyl) -2'-allyloxy -6'-methyl-2-chloroacetanilide, N- (2-methylbutoxymethyl) -2'-allyloxy-6'-methyl- 2-chloroacetanilide, N- (isopropoxymethyl) -2'-isopropoxy-2-chloroaceta- nilide, N- (isobutoxymethyl) -2'-xsopropoxy-2-chloroacetanilide and N- (sec-butoxymethyl) -2'-n-butoxy-2-chloroacetanilide.

The usefulness of the compounds of the present invention as active ingredients in the herbicidal compositions formulated with these compounds and the process for their use will be described below.

The compounds of the present invention can be, 6.

made in many ways. For example, these compounds can be prepared by the azomethine process described in US Patents 3,442,945 and 3,547,620 mentioned above. According to the azomethine process, the appropriate primary aniline is reacted with formaldehyde to obtain the corresponding methyleneaniline (substituted phenylazomethine) which is then reacted with a haloacetylation agent such as chloroacetyl chloride or chloroacetic acid anhydride, which in turn is reacted with the appropriate alcohol to obtain the corresponding N-alkoxymethyl- or N-alkenyloxymethyl-2-chloroacetanilide as a final product.

Another process for producing compounds according to the present invention involves an N-alkylation of the anion of the appropriate secondary 2-haloacetanilide with an alkylating agent, under basic conditions.

A modification of this N-alkylation process is described in Example 1 to prepare the compounds of the present invention. The N-alkylation process described in Example 2 here involves the in situ preparation of halomethyl and alkyl ethers used as starting materials in the N-alkylation process.

EXAMPLE 1 This example describes the use of an N-alkylation process to prepare the compounds according to the present invention. In the exemplary embodiment of the method of this example, the alkylating agent is formed in situ, thereby performing an efficient, economical and simple operation.

To a cooled mixture of 9.25 g (0.125 mole) of isobutanol, 1.86 g (0.062 mole) of anhydrous para-formaldehyde and 100 ml of methylene chloride was added 7: 56 g ( 0.062 mol) of acetyl bromide; the mixture was stirred until all of the para-formaldehyde was dissolved, i.e. about 45 minutes. To the mixture was then added 4.55 · g (0.02 mole) of 2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanilide and 2.0 g of benzyltriethylammonium chloride in 100 ml of methylene chloride. The mixture was 7.

cooled to 15 ° C, 50 ml of 50% NaOH was added all at once and stirred for 5 minutes. To the mixture was added 150 ml of cold water. The layers were separated, washed with water, dried over MgSO 4 and evaporated by the device called Kugelrohr to obtain 5.0 g (79% yield) of a yellow liquid with a boiling point of 107 ° C under 0.02 mm Hg.

Analysis calculated for C16H24C1N03 (%): C, 61.24; H, 7.71;

Cl, 11.30 10: Found; C, 61.24; H, 7.72;

Cl, 11.28

The product has been identified as N- (isobutoxymethyl) -21-methoxy ~ 3 ', 6'-dimethyl-2-chloroacetanilide.

EXAMPLES 2-8; 2n following substantially the same procedure and the same conditions as those described in Example 1, but substituting the appropriate secondary anilide and the appropriate alkylating agent as starting materials and suitable amounts of these products , the corresponding N- (alkoxymethyl) and N- (alkenyloxymethyl) -2-haloacetanilides were prepared; these compounds are identified in Table I, with certain physical properties.

TABLE I

, c Ea- I [FSHpre- P.E. lElé-LÿîiiYse | 25 pie n "Empirical compound" Cment Cal- Trou-; ___ L ______________ (m Hg) ¥ culëe | ye i 2 N- (isopropoxymé- Clt.H C1.N0 'Ί13 C 60,10 60,38 thyl) -21- isopropo- (0.01! H 7.40 6.80 xy- 2- Cl 11.83 11.94 chloroacetanilide 3 N- (isobutoxymethyl) - CH C1N0, 113 C 61.24 61.23 30 2 '-isopropoxy- 2- (0.03) H 7.71 7.72 chloroacetanilide Cl 11.30 11.30 4 N- (allyloxymethy1) - C. C1N0 ^ 116 C 62.03 61.98 21-allyloxy-6'-me- Zü (0,03] H 6,51 6,53 thyl-2-chloroacé- Cl 11,44 11,44 tanilide 35 5 NU- sec ~ bu ~ C'-H C1N0., 115 C 62,28 62,18 ty loxymé thy 1) - 2 '- 1/26 3 (o, 02) H 7.99 8.03 n-butyl-2-chloro- Cl 10.81 10.80 acetanilide 8.

TABLE I (Continued) 6 N- (n-butoxymethyl) - C .. J. C1N0-, 108 C 61.24 61.15 2'-methoxy-3 ', 6' -di- ib J (0,1) H 7.71 7.79 methyl-2-chloroaceous- Cl 11.30 11.30 tanilide 5 7 N- (sec-butoxymethyl) - C., H C1N0, 116 C 61.24 61.13 21-methoxy-3 ', 6'-di- ib J (0.07) H 7.71 7.78 methyl-2-chloroaceous- Cl 11.30 11.24 tanilide 8 N- (2-methylbutoxy- C, fiH _C1N0_ 118 C 63 , 61 63.61 methyl) -21-allyl-61- 10 2b J (0.08) H 7.71 7.79 methyl-2-chloroaceous - - Cl 10.43 10.44 10 ___ tanilide_______

The starting materials consisting of secondary anilides, used in the preparation of the above examples, are prepared according to known methods, for example by haloacetylation of the corresponding primary amine with haloacetylating agents such as halide d 'ha-loacetyl or a haloacetic acid anhydride. Typically, the appropriate amount of the appropriate primary amine is dissolved in a solvent, such as methylene chloride, containing a base, for example 10% NaOH, and vigorously stirred while mixing with a 1 'solution. haloacetyl halide, for example chloroacety chloride, with external cooling, for example at 15-25 ° C.

The layers are separated and the organic solvent layer is washed with water, dried and evaporated in vacuo.

The primary amines used to prepare secondary anilides can also be prepared by known means, for example by catalytic reduction of the corresponding appropriately substituted nitrobenzene, for example a 2-alkoxy-6-alkylnitrobenzene, in a solvent such as an alcohol / for example ethanol, using a platinum oxide catalyst; for 2-alkenyloxy (eg allyloxy) -6'-alkyl compounds, chemical reduction "using iron and acetic acid can be used.

As noted above, the compounds of the present invention have been found to be effective as herbicides, particularly as pre-emergent herbicides, although the activity is 9.

post-emergence life was also presented. Tables II and III summarize the results of tests carried out to determine the herbicidal activity of pre-emergence of the compounds of the present invention.

5 The pre-emergence test was carried out as follows:

Good top soil quality is placed in aluminum boxes and compacted to a depth of 9.5mm to 12.7mm from the top of the box. Above the ground, a predetermined number of seeds or vegetative propagules of various plant species are placed.

The soil required to fill the boxes at level after sowing or adding vegetative propagules is weighed in a box. The soil and a known quantity of the active ingredient applied in a solvent or in the form of a suspension of wettable powder are completely mixed and used to - cover the prepared dishes. After treatment, the boxes are sent to a greenhouse bench where they are provided with an initial irrigation of water from above, equivalent to 0.64 cm of water fall, then humidified by irrigation with des-2o sous , as is necessary to give moisture adégua-te for germination and growth.

Approximately 2 weeks after seeding and treatment, the plants were observed and the results recorded. Tables II and III below summarize these results. The herbicide rating was obtained using a fixed scale based on the percentage of damage to each plant species. The evaluations are defined as follows:% of control Evaluation 30 0-24 0 25-49 1 50-74 2 75-100 3

The plant species used in a series of 35 tests, the results of which are presented in Table II, are identified by a letter according to the following legend: 10.

A Canada thistle E Quarter lamb I Young plants B Field nielle F Beautiful Johnson grass grass C Velvet leaf G Yellow sedge of J Fluffy brome D Volubilis of walnut gardens K Bass grass - 5 H Char grass - latan courtyard

TABLE II

Pre-emergence activity 10 Composed of _Plant species_

example n ° __kg / ha__ABCDEFG'HIJK

1 11.2 33033333033 5.6 11032333033 2 11.2 01131103033 5.6 00120100033 3 11.2 30110232033 15 5.6 00110130033 4 11.2 31222230033 5.6 31113233333 5 11.2 ---- 2232133 5.6 00000131033 6 11.2 32123333333 5 6 32123332033 7 11.2 32123333333 5.6 31122333133 8 11.2 30002312133 _ 5.6_ [00000012233

The compounds were further tested using the above procedure on the following plant species: L Soybean R Sesbania hemp M Sugar beet E Lamb quarter „N Wheat F Beautiful grass 30 0 Rice C Velvet leaf P Sorghum j Downy Brome "B Nielle des champs S Panicum Spp.

Q Wild buckwheat K Backyard grass D Garden volubilis T Wild grass 35

The results are summarized in Table III.

11.

TABLE III

Pre-emergence activity Z ~ T „” Plant species

Consists of L M N 0 P B Q D R ~ Ë F C J S K T

example n ° kg / ha 5 - 3 2 2 3 2 2 2 3 3 3 2 0 3 3 3 3 1.12 1203010022303333 0.28 01020000000012 33 0.06 0101011000000133 0.01 01000000-0000013 2 5.6 1223102223303333 10 1.12 0102 002 003 333 0.28 00000001020023 33 0.06 0000101112002333 3 -5.6 0233100213303333 1.12 002310011 1002333 0.28 0022000000001333 0.06 000100 1000001133 15 4 5.6 2233302132313333 1.12 122310101000033 5.6 022210113220333- 1.12 010200001010333- 20 0.28 010100001110313- 0.06 000000001000002- 6 5.6 222332223221333- 1.12 122321223220333- 0.28 011100111110233- 0.06 011100112000123- 0.01 11000001100003- 1.12 121310112220333- 0.28 021300102110233- 8 5.6 012210111010333- 1.12 011100000030333- 0.28 000000001030103- 30 0.06 000000000030000- _ 0.01__000000000000000- - The herbicides of the present invention have been found to have superior properties unexpected way as selective pre-emergence herbicides for use in sorghum, more particularly for the selective control of hard-to-destroy weeds comprising one or more of the weeds consti 12.

killed by young Johnson grass plants, brittle cane, red root anserine, yellow sedge of walnut trees and white prosomillet, in addition to other problematic weeds such as yellow fox tail, 5 backyard grass and large wild grass. Selective control and suppression of some of the above-mentioned weeds and others with the herbicides of the present invention have been found in a large number of other crop plants, including soybeans, wheat, rice and sugar beet, as shown in Table III above. However, the markedly remarkable herbicidal properties of the compounds of the present invention are most evident in their selective weed control in sorghum.

To illustrate the unexpectedly superior properties of the compounds of the present invention on both an absolute and a relative basis, comparative tests were conducted in the greenhouse with: (1) compounds homologous to the prior art most intimately related in chemical structure to the compounds of the present invention and (2) two other compounds which, although not homologous, fall within the scope of the prior art and one of them they have superior properties like the herbicide for sorghum and both are commercial herbicides. All of the compounds in the comparative tests below are generically defined as substituted phenyl-N-hydrocarbyloxyalkyl-2-haloaceous-tanilides. As used in the result tables here, the compared compounds of the prior art are identified as follows; A. N- (methoxymethyl) -2'-methoxy-6'-t-butyl-2-chloroacetanilide (Example 18, US Pat. Nos. 3,442,945 and 3,547,620) B. N- (methoxymethyl) -2'-methoxy-6'-t-butyl-2-bromo-35 acetanilide (example 34 of American patent n ° 3,547,620 and example 36 of American patent n ° 3,442,945) C. N- (methoxymethyl) - 2 '-methoxy-6' -methyl-2-chloro- - 13 - »acetanilide (compound No.6 of Belgian patent No. 810 763. also indicated in the published German patent application No. 2 402 983) 5 D. N- (ethoxyethyl) -2'-methoxy-6'-methyl-2-chloroacetanilide (compound No.7 in Belgian patent No.810763) E. N- (1-methoxyprop-2-yl) -2 ' -methoxy-6'-methyl-2-chloroacetanilide (compound No. 9 of Belgian patent No.

810 763) 10 P. N- (methoxyethyl) -2'-ethoxy-6'-methyl-2-chloroacetanilide (compound No.16 of Belgian patent No. 810 763) G. N- (ethoxyethyl) -2 ' -ethoxy-61-methyl-2-chloroacetanilide (compound No.18 of Belgian Patent No. 810,763) H. N-isopropy1-2-chloroacetanilide, common name "propachior" I. N- (methymymethyl) -2 ', 6'-diethyl-2-chloro-acetanilide (example 5 of American patents No. 3442 945 and No. 3547620). Common name "alachlor", active ingredient in the commercial herbicide known under the registered trademark 20 Lasso, which is a registered trademark of the company called Monsanto Company.

J. N- (isopropoxyethyl) -2'-methoxy-61-methyl-2-chloroacetanilide.

Although compound H above has a less similar structure than that of the homologous herbicides mentioned in US Pat. Nos. 3,442,945 and 3,547,620, because it lacks an alkoxyalkyl or alkenyloxyalkyl substituent on it. nitrogen atom and an alkoxy substituent in an ortho position, it is included in the tests here because it is referred to in US Pat. Nos. 4,070,389 and 4,152,137 and has been shown superior properties as a commercial herbicide for sorghum, compared to other compounds in these patents. Likewise, compound I is included in the tests here because it is included in the scope of US patent protection Nos. 3442 945 and No.

3,547,620 and obtained commercial commercial herbicide status.

In pre-emergence herbicide tests, the 40 compounds of the present invention were compared to the prior art AI compounds against the control or destruction of various herbs, emphasizing that 3.4 .

3-es species with narrow leaves ^ difficult to destroy, which are predominant infestations in sorghum. The experimental results are presented below.

In discussing the results below, reference is made to the herbicide application rates symbolized by "GRis" and "GRgg"; these rates are given in kilograms per hectare (kg / ha). GR ^, - defines the maximum rate of herbicide required to produce 15% (or less) of damage to the plants to be harvested, and GRg ,. defines the minimum rate required 10 to obtain 85% inhibition of weeds. The rates GR ^ 5 and GRg ,. are used as measures of potential commercial performance, it being understood, of course, that suitable commercial herbicides may cause more or less damage to plants within reasonable limits.

Another guide to the effectiveness of a chemical as a selective herbicide is the "selectivity factor" ("SF") for a herbicide in given crop plants and in given weeds. The factor of 2o selectivity is a measure of the relative degree of safety for the plants to be harvested and of damage to the weeds and is expressed as a function of the ratio GR ^^ / GRg ^, that is to say the rate GR15 for the plant to be harvested divided by the GRg5 rate for the weed, the two rates being 25 kg / ha. In the tables below, when used, the selectivity factors are shown in parentheses after the weed; the symbol "NS" indicates "non-selective". Marginal or questionable selectivity is indicated by a dash (-) after the plant to be harvested.

Since the tolerance to the plants to be harvested and the control or destruction of weeds are interrelated, a brief discussion of this relationship depending on the selectivity factors is significant. In general, it is desirable that the safety factors for the crops to be harvested, i.e. the herbicide tolerance values, be high, since higher concentrations of herbicide are frequently desired for a reason. 15.

or for another. Conversely, it is desirable that the weed control rates be low, that is to say that the herbicide has a high unit activity, for economic and possibly ecological reasons. However, low rates of herbicide application may not be adequate for controlling certain weeds and a higher rate may be required.

Therefore, the best herbicides are those that control the greatest number of weeds with the least amount of herbicide and that provide the greatest degree of safety for the plants to be harvested, i.e. tolerance for plants to harvest. Therefore, "selectivity factors" (defined above) are used to quantify the relationship between safety for the plants to be harvested and weed control or destruction. With reference to the selectivity factors shown in the tables, the higher the numerical value, the greater the selectivity of the herbicide for weed control in a given crop.

2o The pre-emergence tests to which we refer here include both tests in greenhouses and tests in the fields. In greenhouse tests, the herbicide is applied as a surface application after planting seeds and vegetative propagules or by incorporation in a certain amount of soil, to be applied as a covering layer on the seeds in pre-seeded experimental containers. In field tests, the herbicide is incorporated into the soil before the plant ("PPI"), i.e. the herbicide is applied to the soil surface and then incorporated into it by means mixing, followed by planting the seeds of the plant to be harvested.

The experimental surface application process used in the greenhouse is carried out as follows: containers 35 for example aluminum boxes typically 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, having drainage holes in 16.

the bottom, are filled at level with loamy soil soil called Ray, then compacted to a level of 1.27 cm from the top of the pots. The pots are then sown with a species of plant to be tested, then covered with green by a 1.27 cm layer of the experimental soil. The herbicide is then applied to the soil surface with a belt sprayer, at the rate of 187 l / ha under 2, a pressure of 2.11 kg / cm; other spraying means, for example a spraying device called DeVilbiss, 10 are also used on occasion. Each pot receives 0.64 cm of water as top irrigation and the pots are then placed in greenhouses for later irrigation as needed.

. As an alternative procedure, top irrigation can be omitted. Observations of herbicidal effects are made approximately three weeks after treatment.

The treatment with herbicides by incorporation in the soil, used in tests in greenhouses, is as follows:

Good top soil quality is placed in aluminum boxes and compacted to a depth of 9.5mm to 12.7mm from the top of the box. Above the ground are placed a number of seeds or vegetative propagules of various plant species. The soil required to fill the boxes at level after sowing or adding vegetative propagules is weighed in a box. The soil and a known amount of the active ingredient, applied in a solvent or as a suspension of wettable powder, are completely mixed and used to coat the prepared dishes. After treatment, the boxes are provided with an initial irrigation of water from above, equivalent to 0.64 cm of rain, then humidified by irrigation from below, as necessary to give adequate humidity for the germination and growth. As an alternative procedure, the top irrigation can be omitted. Observations are made 17.

About three weeks after seeding and treatment.

<In the tables below, results have been averaged for compounds which have been tested in several trials from application rates in the range of 0.07 to 2.24 kg / ha.

In a first comparative test, the results of pre-emergent herbicidal activity are presented in Table IV, comparing the relative efficacy of the compounds of Examples 1 and 5, which are representative compounds of the present invention, with compounds of interest in the prior art, i.e., compounds A, B, D, P and G, as selective herbicides against particular weeds commonly associated with sorghum. The weeds used in the tests here have the following abbreviations in the tables: red-rooted anserine (RPW), young Johnson grass seedlings (SJG), brittle cane (SC), white prosomillet (WPM), farmyard (BYG), large wild grass (LCG) and yellow fox tail (YFT).

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Referring to the results in Table IV, it will be seen that, with respect to the safety for the plants to be harvested (as indicated by the rate GR ^, for sorghum), the compounds of the present invention showed a superior 5 remarkable riority compared to compounds of the prior art. More particularly, compared with the most structurally related compounds of the prior art, that is to say compounds A and B having the configuration of N-alkoxymethyl-2'-6-alkoxy-alkyl- 2-haloacetanilide, the compounds of the present invention in the test were at least 8.0 to more than 16.0 times safer on sorghum than compound B and about 4.0 to more than 8.0 times more confident that compound A. Likewise, the compounds of the present invention were; 15 from 8.0 to more than 16 times safer on sorghum than the homologous compounds of the prior art Df F and G, - each of which caused more than 15% damage to sor gho at a very low rate of less than 0, 14 kg / ha.

With regard to weed control or destruction, indicated by the GRg ^ application rates under each weed, it will be noted that all of the prior art compounds in the test, except compound A, were completely non selective or marginally or doubtfully selective against all weeds in the sorghum test. Compared with Compound A, the compounds of the present invention were approximately 4.0 to 8.0 times more effective against young Johnson grass plants, large wild grass and backyard grass, and 2, 0 to 4.0 times more effective against the tail 30 of yellow fox. The compound of Example 5 also exhibited a positive selective control of the brittle cane and the yellow ca-rex of the walnut trees and a marginal selectivity with respect to the red-rooted anserine and the white prosomillet, which compound A did not provide. not.

In another comparative test, the compound of Example 1 was compared for its preemergence herbicidal efficacy compared to that of compounds C, D and J, the re-20.

results from this test are shown in Table V.

TABLE V

5 GR rate, t GRfic rate-

Compo- (kg / ha) (kq / ha) ü ___

sé Sorgho sjg BYG | LCG ŸFT

~ 15 "5714 0.14 (NS) <0.14 (-) <0.14 (-) <0.14 (-) C <0.14 0.28 (NS) <0.14 (-) < 0.14 (-) <0.14 (-) J <0.14 0.14 (NS) <0.14 (-) <0.14 (-) <0.14 (-) 10 Ex. 1 1 , 12 0.84 (1.3) <0.14 (> 8.0) <0.14 (> 8.0) <0.14 (> 8.0)

Referring to the results in Table V, it is noted that the compound of the present invention of Example 1 had a safety factor in sorghum significantly greater than that of the compounds of the prior art, i.e. - say it was at least 8.0 times safer. In addition, in addition to having a higher safety factor for the plants to be harvested, the compound of the present invention showed selectivity factors uniformly and remarkably superior to those of the prior art compounds against each of the weeds in the test. . Note that compounds C, D and J of the prior art could not provide positive selectivity for plants to be harvested against young Johnson grass plants and the selectivity of these compounds against remaining weeds was questionable or mar -2 5 ginal at best; in any case, the low safety factors of these compounds make them unsuitable as herbicides for sorghum.

Additional pre-emergence herbicidal results from other tests for the compounds of Examples 1-8 are shown in Table VI.

In Table VI, we show the rates GR ^ and GRg, -for each compound of the invention in sorghum and. interesting weeds, respectively; selectivity factor values are presented in parentheses. Results from multiple tests are presented as i s * 21.

the average of the indicated number of tests. A blank space under a particular weed indicates that that weed was not present in the test given for the compound of interest.

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23.

Referring to the results in Table VI, it will first be noted that each compound of the present invention, tested against both young Johnson grass seedlings and brittle cane, selectively controlled these weeds in sorghum at application rates in the range of 0.57 to 2.24 kg / ha, which is an achievement unmatched by any compound known in the prior art according to the knowledge of the applicant, including herbicides commercial consisting of compounds H and I, in 2 ^ q noting that compound H is a dominant commercial herbicide for sorghum. Furthermore, if not three exceptions each compound of the present invention exhibited a positive selective control of each weed tested; the ; exceptions were the lack of positive selectivity of the compound 2 ^ 5 of Example 4 against white prosomillet and of the compound of Example 7 against the yellow sedge of walnut trees and the marginal selectivity of the compound of Example 5 against 1 anserine with red root.

Since the 2o pre-emergence herbicidal results presented in Tables IV-VI were obtained according to identical routine procedures, a comparison of the herbicidal efficacy of the compounds of the present invention in Table VI can also be made with respect to to herbicidal efficacy for the prior art compounds in Tables IV and V. Here again, it is clearly demonstrated that each of the compounds of the present invention is remarkably superior to all of the more interesting compounds of the prior art depending on the safety for the plants to be harvested, without exception, and the overall selective weed control as evidenced by the selectivity factors, again with exceptions in isolated cases. More particularly, of all the compounds tested in the prior art, only compound A (Table IV) showed a positive selective control of young Johnson grass plants, wild grass, backyard grass and yellow fox tail in sorghum; Compound A was not selective against 24.

the remaining weeds in the test. Against the weeds that Compound A truly selectively controlled, the compounds of the present invention exhibited remarkably higher selectivity, with the exception of the compounds of Examples 2 and 3 which behaved in a manner comparable to Compound A against young plants. Johnson grass. Again, in any case, the low safety factors for sorghum and / or the non-selectivity or questionable selectivity of the compounds of interest of the prior art against all the weeds in the above tests make these compounds completely not suitable as herbicides for sorghum.

As previously mentioned, compounds H and I are designated in prior art patents identified above and are active ingredients in commercial herbicides; Compound H is widely used as a herbicide for sorghum. Although neither of these compounds are homologs, isomers or analogs of the compounds of the present invention, these compounds were tested in an identical manner and against the same weeds as those used in tests for the compounds of the present invention, as shown in Tables IV-VI, to determine their pre-emergent herbicidal activity relative to the compounds of the present invention. It was determined (based on averages of five duplicate tests of Compound I and nine duplicate tests of Compound H) that neither compound selectively controlled brittle cane in sorghum and that compound H did not show a positive control of young seedlings of

Johnson, while compound I exhibited only marginal selectivity, having a selectivity factor of the order of about 1.2 against young Johnson grass plants. Otherwise, Compounds H and I do exhibit selective control of the remaining weeds, as shown in Tables IV-VI. Consequently, it appears that the compounds of the present invention provide significant benefits.

· Even compared to commercial herbicides for selective weed control in sorghum.

The compounds of the present invention have selective herbicidal activity in a large number of plants to re-coite other than sorghum, as indicated in Table III above. In yet other tests, it was also shown that the compound of Example 5 was useful at rates higher than 1.12 kg / ha in soybeans, corn of the field, cotton, cucumber, brittle beans. , garden peas, 10 tomatoes and peanuts. .

Consequently, it will be appreciated from the foregoing detailed description that the compounds according to the present invention have shown unexpected and remarkably superior herbicidal properties both absolutely and relatively compared to the most interesting compounds from the point of view structure, compared to other homologs and related analogs, comprising 2-haloacetanilides from the prior art.

More particularly, the compounds of the present invention 2o have shown remarkable safety for the plants to be harvested in sorghum and particularly remarkable selectivity factors compared to the weed species difficult to destroy, such as young grass plants * of Johnson and brittle cane, and other problematic herbs such as red root anserine, yellow sedge of walnut trees, white prosomillet, yellow fox tail, barnyard grass, wild grass, etc. as presented in Tables II-VI.

The herbicidal compositions of the present invention comprising concentrates which require dilution before application, contain at least one active ingredient and an adjuvant in liquid or solid form. The compositions are prepared by mixing the active ingredient with an adjuvant comprising diluents, extenders (char-35 ges), carriers and conditioning agents to provide compositions in the form of finely divided particulate solids, granules , meatballs, solutions, 26.

dispersions or emulsions. Thus, the active ingredient can be used with an adjuvant, such as a finely divided solid, a liquid of organic origin, water, a wetting agent, a dispersing agent, an emulsifying agent or 5 n ' any suitable combination of these products.

The compositions of the present invention, particularly wettable liquids and powders, preferably contain, as a conditioning agent, one or more surfactants in amounts sufficient to make a given composition readily dispersible in water or oil. The incorporation of a surfactant into the compositions greatly enhances their effectiveness. By the term "surfactant" it is understood that wetting agents, dispersing agents, suspending agents and emulsifying agents are included. Anionic, cationic and nonionic agents can be used with equal ease.

Preferred wetting agents are alkylbenzene and alkylnaphthalenesulfonates, sulfa fatty alcohols, amines or acid amides, long chain acid esters of sodium isethionate, sulfon esters sodium succinate, sulfated or sulphonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils, acetylene glycols, tertiary acetylenic glycols, polyoxyethylene derivatives of alkylphenols (particularly iso-octylphenol and nonylphenol ) and polyoxyethylenic derivatives of the monocarboxylic higher fatty acid esters of hexitol anhydrides (for example sorbitan). Preferred dispersants are methylcellulose, po-lyvinyl alcohol, sodium ligninsulfonates, polymeric alkylnaphthalenesulfonates, sodium naphthalenesulfonate and polymethylene bisnaphthalenesulfonate.

Wettable powders are water dispersible compositions containing one or more active ingredients, an inert solid extender (filler) and one or more wetting or dispersing agents. Solid inert extension products are usually of origin 27.

minerals, such as natural clays, diatomaceous earth and synthetic minerals from silica and the like. Examples of these extension products (fillers) include kaolinites, so-called attapul-5 clay and synthetic magnesium silicate. The wettable powder compositions of the present invention ordinarily contain about 0.5 to 60 parts (preferably 5-20 parts) of active ingredient, about 0.25 to 25 parts (preferably 1-15 parts) of wetting, about 0.25 10 to 25 parts (preferably 1.0-15 parts) of dispersant and 5 to about 95 parts (preferably 5-50 parts) of inert solid extender, all parts being by weight relative to the total composition. When required, about 0.1 to 2.0 parts of the inert solid extender can be replaced with a corrosion inhibitor or anti-foaming agent or both.

Other formulations include dust concentrates containing 0.1 to 60% by weight of an active ingredient on a suitable extension product; these dusts can be diluted for application at concentrations in the range of about 0.1-10% by weight.

The aqueous suspensions or emulsions can be prepared by stirring an aqueous mixture of a water-insoluble active ingredient and an emulsifier until they are uniform and then homogenized to give an emulsion stable of very finely divided particles. The resulting concentrated aqueous suspension is characterized by its extremely small particle size so that, when diluted and sprayed, the overcoating is very uniform. Suitable concentrations of these formulations contain about 0.1-60%, preferably 5-50% by weight, of 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 microencapsulated phase, dispersed in an aqueous phase.

* 28.

In an exemplary embodiment, the tiny capsules are formed by bringing together an aqueous phase containing an emulsifier consisting of ligninesulfonate and a chemical immiscible with water, and polyphenylisocyanate of po-5 lymethylene, by dispersing the immiscible phase to water, in the aqueous phase, followed by 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, thereby forming microcapsules. Generally, the concentration of the microencapsulated material will range from approximately 480 to 700 g / l of total composition, preferably 480 to 600 g / 1.

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

The concentrate compositions herein generally contain about 0.1 to 95 parts (preferably 5-60 parts) of active ingredient, about 0.25 to 50 parts (preferably 1-25 parts) of surfactant. active and, when required, about 4 to 94 parts of solvent, all parts being by weight based on the total weight of the emulsifiable oil.

Granules are physically stable particulate compositions comprising the active ingredient adhering to or distributed through a base matrix of an inert, finely divided particulate extension product. To assist in the leaching of the active ingredient from the particulate product, a surfactant, such as those indicated above, may be present in the composition. Clays 29.

Pyrophyllites, illite and vermiculite are key examples of well-functioning classes of particulate mineral extension products (fillers). Preferred extension products are porous absorbent preformed particles, such as preformed and sieved particulate attapulgite or thermally expanded particulate vermiculite and finely divided clays such as kaolin clays, hydrated attapulgite or clays bentonitics. These extension products are sprayed or mixed with the active ingredient to form the herbicidal granules.

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

The compositions of the present invention may also contain other additive products, for example fertilizers, other herbicides, other pesticides, safety products and the like, used as adjuvants or in combination with any of the adjuvants described above. Chemicals useful in combination with the active ingredients of the present invention include, for example, triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic acid or phenol derivatives , thiolcarbamates, triazoles, benzoic acids, nitriles, biphenyl ethers or the like, such as: Nitrogen / sulfur heterocyclic derivatives 30 2-chloro-4-ethylamino-6-isopropylamino-s-triazine 2-chloro -4,6-bis (isopropylamino) -s-triazine 2-chloro-4,6-bis (ethylamino) -s-triazine 2,2-3-isopropyl-1H-2, 1,3-benzothia dioxide -diazin-4- (3H) -one 35-amino-1,2,4-triazole the salt of 6,7-dihydrodipyrido (1,2-a; 2 ', 1'-c) -pyra-zidinium 30.

5-bromo-3-i sopropy1-6-m thylurac ile 1,1'-dimethyl-4,4'-bipyridinium

Ureas

N '- (4-chlorophenoxy) phonyl-N, N-dimethylurea 5 N / N-dimethyl-N, - (3-chloro-4-methylphenyl) urea 3- (3,4-dichlorophenyl) -1, 1-dimethylurea 1,3-dimethyl-3- (2-benzothiazolyl) urea 3- (p-chlorophenyl) -1,1-dimethylurea l-butyl-3- (3,4-dichlorophenyl) -1-methylurea 10 Carbamates / thiolcarbamates

2-chloroallyl diethyldithiocarbamate Ν, Ν-diethylthiolcarbamate S- (4-chlorobenzyl) isopropyl N- (3-chlorophenyl) carbamate Ν, Ν-diisopropylthiolcarbamate S-2,3-dichloro-, 15 allyl ethyl Ν, Ν-dipropylthiolcarbamate S-propyl dipropylthiolcarbamate

Acetamides / acetani lides / anilines / amides 2-chloro-N, N-diallylacetamide 20 Ie N, N-dimethyl-2,2-diphenylacetamide N- (2,4-dimethyl-5 - [[(trifluoromethyl) sulfonyl] amino] phenyl) acetamide N-isopropyl-2-chloroacetanilide 2 ', 61-diethyl-N-methoxymethyl-2-chloroacetanilide 25 2, -methyl-6'-ethyl-N- (2-methyloxyprop “2-yl ) -2- chloroacetanilide 1'a, a, a-trifluoro-2,6-dinitro-N, N-dipropyl-p-tolui-dine N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide 30 Acids / esters / alcohols 2,2-dichloropropionic acid 2-methyl-4-chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid methyl 2- [4- (2,4-dichlorophenoxy) phenoxylpropionate acid 3-amino-2,5-dichlorobenzoic acid 2-methoxy-3,6-dichlorobenzoic acid 31.

2,3,6-trichlorophenylacetic acid Nl-naphthylphthalamic acid 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-sodium nitro-benzoate 5 4,6-dinitro-o-sec -butylphenol N- (phosphonomethyl) glycine, its mono-alkyl salts (starvation, its alkali metal salts and combinations thereof

Ethers 10 2,4-dichlorophenyl ether and 4-nitrophenyl ether 2-chloro-a, a, a-trifluoro-p-tolyl-3-ethoxy-4-nitro-diphenyl

Various products 2,6-dichlorobenzonitrile 15 monosodium acid methanearsonate disodium methanearsonate

Useful fertilizers in combination with the active ingredients include, for example, ammonium nitrate, urea, potassium carbonate and superphosphate. Very useful additive products include materials in which plant organisms take root and grow, such as compost, manure, humus, sand and the like.

Herbicidal formulations of the types described above are given by way of examples in several illustrative embodiments below.

I. Emulsifiable concentrates% by weight A. Compound of Example 1 50.0 30 Mixture of calcium dodecylbenzenesulfonate / polyoxyethylene ethers (for example product known under the registered trademark Atlox 3437F and Atlox 3438F) 5.0

Monochlorobenzene 45.0 35 100.00 B. Compound of Example 2 85.0 Mixture of calcium dodecylsulfonate / 32.

alkylarylpolyether alcohol 4f0

Solvent consisting of aromatic hydrocarbons in 11.0 100.00 5 C. Compound of example n ° 3 5; 0 Mixture of calcium dodecylbenzenesulfonate / polyoxyethylene ethers (for example product Atlox 3437F) 1.0

Xyiene 94.0 10 100.00 II. Liquid concentrates% by weight A. Compound of Example 4 10.0

Xyiene 90.0 15 100.00 B. Compound of Example 5 85.0

Dimethyl sulfoxide 15.0 100.00 C. Compound of Example 6 50.0 20 N-methylpyrrolidone 50.0 100.00 D. Compound of Example 7 5.0

Castor oil ethoxylated 20.0

Product called Rhodamine B 0.5 25 Dimethylformamide 74.5 100.00 III. Emulsions% by weight A. Compound of Example No. 8 40.0 30 Polyoxyethylene / polyoxypropylene block copolymer with butanol (for example product known under the registered trademark Tergitol XH) 4.0

Water 56.0 100.00 35 B. Compound of Example 1

Polyoxyethylene / polyoxypropylene block copolymer with butanol 3.5 33.

Water 91.5 100.00 IV. Wettable powders% by weight 5 A. Compound of Example 3 25.0

Sodium lignosulfonate 3.0 Sodium N-methyl-N-oleyl-taurate 1.0

Amorphous silica (synthetic) 71.0 10 100.00 B. Compound of Example 5 80.0

Sodium dioctylsulfosuccinate 1.25

Calcium lignosulfonate 2.75

Amorphous silica (synthetic) 16.00 15 100.00 C. Compound of Example 6 10.0

Sodium lignosulfonate 3.0 Sodium N-methyl-N-oleyl-taurate 1.0 2o So-called kaolinite clay 86.0 100.00 V. Dust% by weight A. Compound of Example 3 2.0 25 Attapulgite 98.0 100.00 B. Composed of Example 4 60.0

Montmorillonite 40.0 100.00 30 C. Composed of Example 5 30.0

Bentonite 70.0 100.00 D. Compound of Example 6 1.0

Diatomaceous earth 99.0 35 100.00 34.

VI. Granules% by weight A. Compound of Example 7 15.0

Granular attapulgite (passing 5 through a sieve with a mesh opening of between 0.841 mm and 0.420 mm, i.e. 20-40 mesh) 85.0 100.00 B. Compound of example n ° 8 30.0

Diatomaceous earth (passing through a sieve with a mesh opening between 0.841 mm and 0.420 mm) 70.0 100.00 C. Compound of example n ° 1 0.5 x Bentonite (passing through a sieve with ou- jL5 mesh between 0.841 mm and 0.420 mm) 99.5 100.00 D. Composed of example 2 5.0

Pyrophyllite (passing through a 2o sieve with a mesh opening between 0.841 mm and 0.420 mm) 95.0 100.00 VII. Microcapsules% by weight 25 A. Compound of Example 4 encapsulated in a polyurea envelope wall 49.2

Sodium lignosulfonate (eg product known under the brand name Reax 88 B) 0.9

Water 49.9 100.00 B. Compound of Example 5 * encapsulated in a polyurea shell wall 10.0

Potassium lignosulfonate (for example product known under the trademark

Reax C-21) 0.5 '35

Water 89.5 100.00 C. Compound of Example 6 encapsulated in a polyurea 80.0 envelope wall

Lignosul-fate magnesium salt (product known under the trademark Treax LTM) 2.0, Water 18.0 100.00

When operating in accordance with the present invention, effective amounts of the acetanilides of the present invention are applied to the soil containing the plants, or are incorporated into aquatic media in any suitable manner. The application of liquid compositions and particulate solid compositions to the soil can be carried out by conventional methods, for example mechanical dust-forming devices, telescopic and hand-held spraying devices and dust-forming devices by spray. The compositions can also be applied from aircraft in the form of a dust or spray due to their effectiveness at low doses. The application of a herbicidal composition to aquatic plants is usually accomplished by adding compositions to the aquatic media in the area where control of the aquatic plants is desired.

The application of an effective amount of the compounds of the present invention to the location of the 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 its stage of development, the type and condition of the soil, the amount of rainfall and the specific acetanilide employed. In the selective application of pre-emergence to plants or soil, a dose of 0.02 to approximately 11.2 kg / ha, preferably from approximately 0.04 to approximately 36.

5.60 kg / ha, or suitably 1.12 to 5.6 kg / ha of acetanilide is commonly used. Lower or higher rates may be required in some cases. A person skilled in the art can easily determine from this description, including the examples above, the optimum rate to apply in any particular case.

The term "soil" is used in its broadest sense to include all of the classical "soils", as defined in the New International Dictionary of Webster, 2nd edition, unabridged (1961). Thus, the term refers to any substance or medium in which vegetation can take root and grow, and includes not only * earth, but also compost, fertilizer, manure (rubbish - 15 res ), humus, sand and the like, adapted to maintain plant growth.

The present invention is not limited to the embodiments which have just been described, it is on the contrary susceptible of variants and modifications which will appear to those skilled in the art.

Claims (13)

1. Compounds, characterized in that they have the formula: 5 0 II C1CH0C CH „OR 2. Compound according to claim 1, characterized in that it is formed by N- (isobutoxymethyl) -2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanilide. 2. X '2 R3-fS-OR1 10 R2 where R is isopropyl, n-butyl, isobutyl, sec-butÿ-le, allyl or 2-methylbutyl; is methyl, isopropyl, n-butyl or * 15 allÿle and R2 and r3 are hydrogen, or methyl; provided that ; Rr R2 ®t each represent the methyl group when R is the n-butyl, isobutyl or sec-butyl group; R2 and r3 each represent hydrogen when R is isopropyl, isobutyl or sec-butyl and R ^ is isopropyl or n-butyl, and R2 is hydrogen and R ^ is methyl when R is the 2-methylbutyl or allyl group and that R ^ 25 is the allyl group. 3. Compound according to claim 1, characterized in that it is formed by N- (n-butoxymethyl) -2'-methoxy-3 ', 61-dimethyl-2-chloroacetanilide. 4. Compound according to claim 1, characterized in that it is formed by N- (sec-butoxymethyl) -2'-methoxy-, 3 ', 6'-dimethyl-2-chloroacetanilide. 5 - Compound according to claim 1, characterized in that it is formed by N- (allyloxymethyl) -2'-allyloxy-61-methyl-2-chloroacetanilide. 38. 5 C1CH25 \ ν ^ * 2 ™ • ““ to.; “· 10 where R, R1, R2 and R3 are as defined in claim 1. 6. Compound according to claim 1, characterized in that it is formed by N- (2-methylbutoxymethyl) -2'-al-lyloxy-6'-methyl-2-chloroacetanilide. 7. Compound according to claim 1, characterized in that it is formed by N- (isopropoxymethyl) -2'-isopro-poxy-2-chloroacetanilide. 8. Compound according to claim 1, characterized in that it is formed by N- (isobutoxymethyl) -2'-isopro-poxy-2-chloroacetanilide. 10 9 - Compound according to claim 1, characterized in that it is formed by N- (sec-butoxymethyl) -2'-n-buto-xy-2-chloroacetanilide. 10. Herbicidal compositions, characterized in that they comprise an adjuvant and a quantity, effective * 15 from the herbicidal point of view, of a compound having the formula: O c1ch25 ch9or 20 J R3- [fV- ~ 0Rl ^ \ R2 where R, R ^, R ^ and R ^ are as defined in claim 1. 11. Composition according to claim 10, characterized in that the provisions of any one of claims 2 to 9 are applied. 12. A method of combating undesirable plants associated with sorghum, characterized in that it consists in applying, at the place where these plants are found, a quantity, herbicide effective, of a compound having the • ^ formula: 39. Ο 13. Method according to claim 12, characterized in that the provisions of any one of claims 2 to 9 are applied.