FR2479206A1 - N-ALKYL-2-HALOACETANILIDE COMPOUNDS AND HERBICIDE COMPOSITIONS COMPRISING THE SAME - Google Patents

Abstract

A GROUP OF N-ALKYL-2-HALOACETANILIDE COMPOUNDS WITH THE FORMULA: (CF DRAWING IN BOPI) OR R IS METHYL OR ETHYL GROUP, R IS A C RADICAL ALKYL, R IS METHYL, ETHYL OR T-BUTYL GROUP AND R IS HYDROGEN OR THE METHYL GROUP IN THE META POSITION, PROVIDED THAT, WHEN R IS THE ETHYL GROUP, R IS THE N-BUTYL GROUP, R IS THE METHYL GROUP AND R IS HYDROGEN; WHEN R IS THE METHYL GROUP, R AND R ARE ALSO THE METHYL GROUP AND R IS THE ISOPROPYL OR N-BUTYL GROUP; WHERE R IS HYDROGEN AND R AND R ARE BOTH THE METHYL GROUP, R IS THE METHYL GROUP, N-PROPYL, ISOPROPYL, N-BUTYL, ISOBUTYL, SEC-BUTYL, N-PENTYL, ISOPENTYL, 2-METHYLBUTYL, 1 -METHYLPENTYL, 2-METHYLPENTYL, OR 1,3-DIMETHYLBUTYL; WHEN R IS THE ETHYL GROUP, R IS THE METHYL GROUP AND R IS THE ISOPROPYL GROUP, AND WHEN R IS THE T-BUTYL GROUP, R AND R ARE BOTH THE METHYL GROUP, ARE ACTIVE INGREDIENTS IN HERBICIDAL COMPOSITIONS UTILIZED PARTICULATELY IN VARIOUS PLANTS TO COLLECT.

Description

1.

  The present invention relates to the field of 2-

  haloacetanilides and their use in techniques

  agronomy, for example as herbicides.

  The prior art relating to the present

  the invention includes numerous descriptions of 2-haloacid-

  tanilides which may be unsubstituted or substituted by a large number of substituents on the aniline nitrogen atom and

  on the anilide nucleus, comprising alkyl radicals, alcohols

  xy, alkoxyalkyl, halogen, etc. As a prior art relating to the compounds of the present invention, which are characterized by having a methyl or ethyl radical on the anilide nitrogen, an alkoxy radical in an ortho position and a methyl radical in the other ortho position, the technique

  previous closest known to the plaintiff is

  presented by US Pat. Nos. 3,268,584, No.

  3,442,945, Nos. 3,773,492 and 4,152,137. The US patents

  Nos. 3,773,492 and 4,152,137 describe general formulas

  neric for herbicidal compounds which include at

  the compounds of the present invention. However, the only

  N-alkyl-substituted 2-haloacetanilide

  described in US Pat. No. 3,773,492 or the patent

  No. 4,152,137 is the so-called propachlor product, that is,

2.

  that is, N-isopropyl-2-chloroacetanilide, which is a herbicide

  well-known trade certificate; neither of these

  vets do not describe herbicide results for propachlor. U.S. Patent No. 2,863,752 (Reissue Patent No. 26,961) discloses compounds of a class including propachlor (not specifically named), its homologs and analogs. Among the compounds within the scope of US Pat. No. 2,863,752, it has been found that

  propachlor was the most effective herbicide

  and, as a result, it has been developed as a herbicide

  of commercial. U.S. Patent No. 2,863,752 indicates that - the compounds presented can be used at similarly high rates.

  weak than 1.12 kg / ha; however, as presented in the example

  In Table 4, the experimental results presented are limited to application rates of 5.6 kg / ha and 28 kg / ha. In addition, N-ethyl-2chloroacetanilide is a species named in US Pat. No. 2,863. 752. However, US Pat. No. 4,137,070 indicates that this compound (Example No. 406 in the US Pat.

  US Patent No. 4,137,070) is an antidote for herbicide

  called TCPS. In contrast to the previous compounds of US Pat. No. 2,863,752, the compounds of the present invention are highly effective and selective herbicides.

  against excessively difficult weed species

  to be controlled or destroyed, at application rates of less than the rate of 1.12 kg / ha,

less than 0.07 kg / ha.

  The compounds described in US Pat. Nos. 3,268,584 and 3,442. 945 may be more interesting from

  point of view structure for the compounds of the present invention.

  the product says propachlor or related compounds

  your. In particular, Example 13 of US Pat.

  3,268,584 discloses the compound N-t-butyl-2'-methoxy-2-chloroacetate.

  tanilide and example 67 of US Patent No. 3,442,945

  describes the compound 2'-methoxy-6'-t-butyl-2-chloroacetanilide.

  Thus, propachlor differs from the compounds of the present invention.

  by the type of substituent radicals in two posi-

  tions, that is to say the two ortho positions of the molecule, 3. as well as by the particular alkyl radical attached to the nitrogen atom. Example 13 in US Pat. No. 3,268,584 differs in the type of the substituent in an ortho position, the particular alkoxy radical in the other ortho position and the particular alkyl radical attached to the nitrogen atom,

  and Example 67 in US Pat. No. 3,442,945 differs

  compounds of the present invention by the type of substitute

  killing fixed to the nitrogen atom and by the particular alkyl and alkoxy radicals respectively, attached to the ortho positions

of the anilide molecule.

  U.S. Patent No. 4,146,387 discloses composites

  2-haloacetanilide salts which may be substituted by

  alkyl radicals on the nitrogen atom and in both posi-

  ortho. Compounds of US Patent No. 4,146,387

  are described as known herbicides of the indi-

  such as in US Pat. Nos. 3,442,945 and US Pat.

  No. 2,863,752 mentioned above, including propachlor.

  U.S. Patent No. 3,268,584 contains certain herbicidal results relating to the above-mentioned compounds having a chemical configuration most closely related to the compounds of the present invention, and certain results are presented for other homologous compounds and

  analogies less closely related to the structural

  chemical resistance. More particularly, these most interesting references, while describing a herbicidal activity on

  a large number of weeds, do not result in

  States for compounds which are shown to control in

  more and / or simultaneously the difficult annual weeds

  to be destroyed, such as Texas panicum, picotgrass

  te (Raoul grass), wild prosomillet, Alexandrian herb

  dre, red rice, brittle cane and young seedlings

  Johnson, while controlling at the same time or removing

  at the same time a wide range of other annual and perennial harmful weeds, for example yellow walnut sedge, beautiful grass, quarter of lamb,

  fox tails, the: large wild grass and low grass

court.-

  4. A highly useful and desirable property of

  herbicides is the ability to maintain control of the

  herbs over an extended period of time, the more this

  period being longer and better this being during each

  harvest sound. With many herbicides of the technique

  the weed control is adequate only for

  for 2 or 3 weeks, or in some cases higher than

  may be up to 4-6 weeks before the product

  chemical does not lose its effective phytotoxic property. In con-

  sequence, a disadvantage of most prior art herbicides is their relatively short longevity

- in the ground.

  Another disadvantage of some prior art herbicides, somewhat related to soil longevity under normal climatic conditions, is their susceptibility to soil leaching, ie, the lack of persistence of poor control. herbs under strong

  Rainfall that turns off many herbicides.

  Another disadvantage of many prior art herbicides is the limitation of their use in specified types of soil, that is, while some herbicides are effective in soils with

  small amounts of organic matter, they are inefficient

  these in other soils with a high content of

  organic re or vice versa. It is therefore advantageous

  that a herbicide is useful in all soil types from light organic soil to heavy clay and

manure (garbage).

  Another disadvantage of many herbicides

  of the prior art is the limitation to a particular mode.

  effective application, that is to say in the form of

  pre-emergence on the surface or as an ode to

  by incorporation into the soil before the plant. It is highly desirable to be able to apply a herbicide according to any mode of application, whether by

  application on the surface or by incorporation before the plant.

  Finally, a disadvantage in some herbicides 5.

  is the need to adopt and maintain operational modalities

  special handling as a result of the toxic nature

  of these herbicides. As a result, another wish is that a her-

bicide be safe to handle.

  It is, therefore, an object of the present

  to provide a group of herbicide compounds that

  the disadvantages mentioned above of the

  than earlier and that provide multiple benefits in

a single group of herbicides.

  It is an object of the present invention to provide herbicides which selectively control or destroy hard-to-destroy annual weeds, such as Texas panicum, Raoul grass, wild prosomillet,

  Alexander's herb, red rice, brittle cane and game-

  Johnson's seedlings while controlling or removing

  at the same time a broad range of annual weeds

  and less resistant vicas, as mentioned above.

  above, while maintaining the safety of plants with

  in a large number of plants to be harvested, including soya beans, cotton, peanuts, rapeseed, beans

  alfalfa and / or vegetable crops.

  It is another object of the present invention to

  provide herbicidal efficacy in the soil for periods

  extended periods of time up to at least 12 weeks

nes.

  Another object of the present invention is to provide

  herbicides that are resistant to leaching and dilution due to high moisture conditions, eg

  in the form of heavy rainfall.

  Yet another object of the present invention is the provision of herbicides which are effective in a wide range of applications.

  range of soils, for example from light organic soils

  means to heavy clay and manure (garbage).

  Another advantage of the herbicides of this

  invention is the flexibility available in the application mode.

  by surface pre-emergence

  and by incorporation into the soil before the plant.

  6. Finally, it's an advantage of the herbicides of the

  present invention that they are safe and do not require

  special operating procedures.

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

detailed below.

  The present invention relates to compounds having herbicidal activity, to herbicidal compositions containing these compounds as active ingredients and to herbicidal methods of using these compositions in various crops. The Applicant has now found that a group

  2-haloacetanilides, characterized by the combination of

  specific sounds of alkyl radicals on the nitrogen atom of

  lide and in an ortho position and specific alkoxy radicals

  in the other ortho position, has heritable properties

  remarkable and superior bicides unexpectedly

  herbicides of the prior art, including the most closely related compounds of the

more interesting.

  A main feature of herbal compositions

  Bicides of the present invention are their ability to control or destroy a wide range of weeds, including weeds controllable by common herbicides, and, in addition, several weeds which, individually and / or collectively, have escaped to present in control by a single class of known herbicides, while maintaining the safety for the plants to be harvested in relation to several plants to be harvested including, in particular, soya beans, cotton, peanuts, rapeseed, white beans (brittle beans) ), alfalfa, and other plants as well. While the herbicides of the prior art are useful for controlling a large number of weeds, including

  occasional resistant weeds, herbicides

  The unique compounds of the present invention have been shown to be

  to control or suppress a number of

  its resistant herbs, especially the bad ones 7.

  annual grasses such as Texas panicum, picot grass

  te, wild prosomillet (panicum miliaceum), Alexander's herb, red rice, brittle cane and young

  Johnsontout grass plants by controlling and / or removing

  other less persistent annual and perennial weeds.

  The compounds of the present invention are characterized

  by the formula: o Ia ClCH2C / R

R2 'OR1

  R3 where R is methyl or ethyl; R is a C 1 -C 6 alkyl radical, preferably C 3 -C 5 alkyl radicals;

  R2 is methyl, ethyl or t-butyl, preferably

  preferably methyl, and R3 is hydrogen or methyl in the meta position, preferably hydrogen; provided that:

  when R is the ethyl group, R1 is the n group

  butyl, R2 is methyl and R3 is hydrogen;

  when R3 is the methyl group, R and RP2 are also

  the methyl group and R1 is the isopropyl or n-butyl group; when R3 is hydrogen and R and R2 are both

  the methyl group, R1 is the ethyl group, n-propyl group, iso-

  propyl, n-butyl, isobutyl, sec-butyl, n-pentyl, isopentyl,

  2-methylbutyl, 1-methylpentyl, 2-methylpentyl or 1,3-dimethylpentyl

  thylbutyle; when R2 is ethyl, R is methyl, and R1 is isopropyl and 8. when R2 is t-butyl, R and R1 are all

two the methyl group.

  Preferred species of the present invention are: N-methyl-2'-isopentyloxy-6'-methyl-2-chloroacetanilide

  N-methyl-2'-n-propoxy-6'-methyl-2-chloroacetate

nilide

  N-methyl-2'-n-butoxy-6'-methyl-2-chloroacetanic acid

lide

  N-methyl-2'-sec-butoxy-6'-methyl-2-chloroacetate

nilide

  N-ethyl-2'-n-butoxy-6'-methyl-2-chloroacetaniline

of

  N-methyl-2'-isopropoxy-6'-methyl-2-chloroacetate

nilide

  N-methyl-2'-isobutoxy-6'-methyl-2-chloroacetanic acid

lide

  N-methyl-2'-isopropoxy-6'-ethyl-2-chloroacetanic acid

  The utility of the compounds of the present invention, in

  as active ingredients in herbicidal compositions

  with these compounds, and the process for their use

will be described below.

  The compounds of the present invention can be

  manufactured in many ways. For example, these compounds may

  may be prepared by a process involving the N-alkylation of the appropriate secondary 2-haloacetanilide anion with an alkylating agent under basic conditions. The process of

  N-alkylation is described in Examples 1 and 2 herein.

EXAMPLE 1

  This example describes the preparation of a pre-existing species

  N-methyl-2'-n-butoxy-6'-methyl-2-chloroacetanilide.

  In this example, dimethyl sulfate is used as

  alkylating agent for preparing N-alkyl-2-chloroacetaniline

9.

  from the corresponding sec-amide anion.

  2'-n-butoxy-6'-methyl-2-chloroacetanilide, in

  4.9 g (0.02 mole), dimethyl sulfate in

  2.6 g (0.02 mole) and 2.0 g of triethylbenzoic bromide

  zylammonium were mixed in 250 ml of CH 2 Cl 2 while cooling. 50 ml of 50% NaOH were then added in one

  only once at 15 ° C. and the mixture was stirred for two hours.

  res. Water (100 ml) was added and the resulting layers

  your separated. The organic layer was washed with water,

  dried over MgSO 4 and evaporated by the so-called Kugelrohr device.

  A clear liquid having a boiling point of 135 ° C at 0.07 mm Hg was obtained in 78% yield (4.2 g); it was recrystallized by leaving it at rest to provide a solid

  colorless with a melting point of 41-42.5 C.

  Analysis calculated for C14H20ClNO2 (%): C, 62.33; H, 7.47;

C1, 13.14.

Found: C, 62.34; H, 7.49;

Cl, 13.16.

  The product has been identified as N-methyl-2'-n-buto-

xy-6'-methyl-2-chloroacetanilide.

EXAMPLE 2

  In a cooled mixture (15 C) of 2'-n-butoxy-6'-

  methyl-2-chloroacetanilide in an amount of 5.6 g (0.022 mol), diethyl sulfate in an amount of 4.0 g (0.024 mol) and

  2.2 g of triethylbenzylammonium bromide in 250 ml of chlorine

  After the addition of methylene chloride, 50 ml of 50% NaOH was added all at once and the mixture was stirred for 5.0 minutes. Water (150 ml) was added, and the resulting layers separated; the organic layer was washed with water, dried over MgSO 4 and then evaporated by the so-called Kugelrohr device to give 4.1 g (66% yield) of a clear point liquid

  boiling point of 114 ° C at 0.05 mm Hg.

  Analysis calculated for C15H22ClNO2 (%): C, 63.48; H, 7.81;

Cl, 12.49.

Found: C, 63.50; H, 7.85;

C1, 12.48.

  The product has been identified as N-ethyl-2'-n-butoxy-

. 2479206

  10. 6'-methyl-2-chloroacetanilide.

EXAMPLES 3-19

  By following substantially the same modes of operation

  and using substantially the same quantities of

  reactants and the same general conditions as those

  described in Examples 1 and 2, but substituting the

  appropriate anilide to obtain the final N-alkylated product

  other N-methyl-2-haloacetanilides according to the

  mule indicated above were prepared identified in Table I.

TABLE I

  these compounds are -Exem- Compound Formula em- P.E. At Analysis

C elé-CalcuTrou-

  ina (mm men lle Ivé N-methyl-2'-isopent-¿cHg.) _

N-methyl-2'-isopento-

xy-6'-methyl-2-chloro-

roacétanilide

N-methyl-2'-n-pro-

xy-6'-methyl-2-chloro-

roacétanilide

N-methyl-2'-sec-bu-

toxy-6'-methyl-2-

chloroacetanilide

N-methyl-2'-isopropyl

epoxy-6'-methyl-2-

chloroacetanilide

N-methyl-2'-isopropyl

epoxy-6'-ethyl-2-

chloroacetanilide

* N-methyl-2'-isobuto-

xy-6'-methyl-2-chloro-

roacétanilide

N-methyl-2'-methoxy-

6'-t-butyl-2-chloro-

acetanilide

N-methyl-2'-ethoxy-

6'-methyl-2-chloro-

acetanilide

N-methyl-2 '- (1-me-

thylpentoxy) -6'-me-

thyl-2-chloroacéta-

nilide

C15H2 2C1N02

13H18ClNO2

14 20 C1NO2

1:18 pm 2

C14H20C1NO2

(0.05)

(0.15)

(0.03)

(0.01)

C H C 2 NO 11

14 20 21 (0.03)

14 20ClN02

12 16C1N02

C16H24C1NO2

99- (m.p.) 57-5e (m.p.)

(0.08)

  C H C1 C H Cl C H C1 C H C1 C H C1 C H C1 C H C1 C H C H C1 63.48 7.81

112.49

  61.05 7.09 13.86 62.33 7.47 13.14 61.05 7.09 13.86 62.33 7.47 13.14 62.33 7.47 13.14 62.33 7, 47 13.14 59.63 6.67 14.67 64.53 8.12 11.90 63.38 7.80 12.44, 88 7.12 13.70 62.16 7.50 13.10 61, 05 7.09 13.33 62.40 7.52 13.03 62.32 7.49 13.12 62.25 7.5 13.1 59.6 6.7 14.6 64.4 8.1 11 , 8 il L titi 11. TABLE I (Continued)

N-methyl-2'-n-pentoxide

i6'-methyl-2-chloroacë-

tanilide

N-methyl-2'-n-propoxy

mdthyl-6'-methyl-2-

chloroacetanilide

N-methyl-2'-isopropo-

xy-5 ', 6'-dimethyl-

2-chloroacetanilide

N-methyl-2'-n-butoxy-

3 ', 6' .- dimethyl-2-

chloroacetanilide

N-methyl-2'-butoxv-

  ', 6'-dimethyl-2-chloroacetanilide

N-methyl-2 '- (2-methyl-

pentoxy) -6'-methyl-2-

chloroacetanilide

N-methyl-2 '- (2-methyl-

butoxy) -6'-methyl-2-

chloroacetanilide

N-methyl-2 '- (1,3-di-

methylbutoxy-6'-me-

thyl-2-chloroacéta-

nilide H22 ClNO2 14H2oC0 lNO2

C14H20 C1NO2

H22 CN2

22C1NO2

C16H24C1NO2

C15 22ClNO2

C16H23 1N02

(0.12)

-

(0,05-

0.1)

(0.01)

(0.07)

46- (P.f.)

(0.03)

(0.06)

  (0.15 i) C H C1 C H N C H C1 C H C1 C H C1 C H C1 C H C1 C C1 C1 Secondary anilides used as raw materials

  starting point in the above N-alkylation process are prepa-

  by known methods, for example by haloacetylation of the corresponding aniline. For example, the starting sec-anilide used in Example 1 was prepared as follows: 2-n-butoxy-6-methylaniline, in an amount of 27.4 g (0.0153 moles), in 250 ml methylene chloride was stirred vigorously with 10% sodium hydroxide solution

  (0.25 mole) while a solution of chloroacetyl chloride

  in an amount of 17.4 g (0.0154 mole) in

  Methylene was added in 30 minutes, keeping the temperature

  between 15 and 25 C with external cooling. To me-

  The reaction mixture was stirred for a further 60 minutes. After the addition was complete, the separated layers and the methylene chloride layer were washed with water, dried 63.48 7.81 12.49 62.33 7.47, 19 62.33 7 , 47 13.14 63.48 7.81 12.49 63.48 7.81 12.49 64.53 8.12 11, 90 63.48 7.81 12.49 64.53 8.12 11.90 63.36 7.81 12.50 61.59 7.51 62.65 6, 84 13.17 63.54 7.80 12.48 63.56 7.82 12.52 64.59 8.11 11, 96 63.53 7.85 12, 45 64.49 8.14 11.89 I 12. and evaporated under vacuum to obtain 28.3 g of a white solid

with a melting point of 127-128 C.

  Analysis calculated for C13H18ClNO2 (%): C, 61.05; H, 7.09;

Cl, 13.86.

Found: C, 61.04; H, 7.08;

C1, 13.86.

  The product has been identified as 2'-n-butoxy-6'-

  methyl-2-chloroacetanilide. Secondary anilides used as materials

  in Examples 3-19 have been prepared in a manner

like.

  The primary amines used to prepare the;

  secondary anilides mentioned above may be

  by known means, for example by catalytic reduction

  corresponding 2-alkoxy-6-alkyl-nitrobenzene in the ethanol

  by using a platinum oxide catalyst.

  As noted above, it has been found that the compounds

  of the present invention were effective as herbicides, especially

  especially pre-emergence herbicides, although the

  post-emergence activity was also presented. The pre-emergence tests referred to here include the

  times the tests in greenhouses and the tests in the fields.

  In tests in greenhouses, the herbicide is applied either as a surface application after planting seeds or vegetative propagules, or by incorporation into a certain amount of soil to be applied as a cover layer to experimental seeds. in experimental containers pre-seeded. In field tests, the herbicide is incorporated before the plant ("PPI") into the soil, ie the herbicide is applied to the soil surface and then incorporated into it by mixing destDyens , followed by

  Planting the seeds of the plants to harvest.

  The experimental method of surface application

  in the greenhouse is carried out as follows: Containers, 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, with 13 drain holes at the bottom, are filled to the level with loam loam soil called Ray, then compacted to a level of 1.27 cm from the top of the pots. The pots

  seeded with experimental plant species.

  ter, then covered with a layer of 1.27 cm of the experimental soil. The herbicide is then applied to the soil surface with a belt spraying device at the rate of 187 l / ha at a pressure of 2.11 kg / cm. Each pot receives 0.64 cm of water in the form of top irrigation, and the pots are then placed in greenhouse benches for subsequent irrigation from below, as necessary. As

  alternatively, top irrigation can be omitted.

  Observations of herbicidal effects are made

  3 weeks after treatment.

  The soil-incorporated herbicide treatment used in greenhouse testing is as follows: Good top soil quality is placed in

  aluminum boxes and stretched compactly to a depth

  from 9.5 mm up to 12.7 mm from the top of the wood.

  you. Above ground, a predetermined number of

  vegetative propagules of various plant species.

  your. The soil required to fill the boxes after

  seed or addition of 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 fully mixed and used

  to cover the prepared boxes. After treatment, we give

  cans with initial water irrigation from above, equi-

  at 0.64 cm of rainfall, then humidified with irri-

  from below, as is necessary to give

  adequate moisture for germination and growth. com-

  modus operandi, irrigation by the

  above can be deleted. The observations are made

  2-3 weeks after seeding and treatment.

  Tables II and III summarize the results of

  tests conducted to determine the herbicidal activity of

  emergence of the compounds of the present invention; in these tests, 14. the herbicides were applied by incorporation into the soil and humidification by underwater irrigation only;

  a dash (-) means that the indicated plant has not been tested

  ted. The herbicide evaluation was obtained using a fixed scale, based on the percentage of damage to

  each species of plants. Evaluations are defined as com.

follow me% of control Rating

0-24

25-49 1

-74 2

-100 3

  The plant species used in a series of tests, the results of which are presented in Table II, are identified by a letter according to the following legend: A Canada Thistle E Lamb Quarter I B Nielle Herbs F Belle Grass Johnson C Yellow G Carex Velvet Leaf of the Bromine Downy Brome

  D Volubilis of walnut gardens K Lowland grass

H grass of charla- yard tan

TABLE II

  Pre-emergence activity Composed of plant species 1Example n0 i kg / ha A B C D E F G H I J K

1 11,2 3 3 3 3 3 3 3 3 3 3 3

, 6 3 2 2 3 3 3 3 3 3 3 3

2 11,2 3 1 1 2 3 3 - 3 3 3 3

, 6 3 0 1 1 3 3 - 3 1 3 3

3 11,2 3 2 3 3 3 3 3 3 3 3 3

, 6 3 1 3 2 3 3 3 3 2 3 3

4 11,2 3 2 3 3 3 3 3 3 3 3 3

, 6 2 1 3 2 3 3 3 3 3 3 311,2 3 2 3 3 3 3 3 3 3 3 3

, 6 3 2 3 3 3 3 3 3 3 3 3

6 11,2 3 2 2 3 3 3 3 3 3 3 3

, 6 3 2 2 3 3 3 3 3 2 3 3

7 11,2 3 3 3 3 3 3 3 3 3 3 3

, 6 3 1 2 3 3 3 3 3 3 3 3

15. TABLE II (Continued)

8 11,2 3 2 3 3 3 3 3 3 1 3 3

, 6 3 2 2 2 3 3 3 3 3 3 3

9 11.2 3 0 3 3 3 3 3 3 3 3 3

, 6 3 0 2 3 3 3 3 3 3 3 3

1,12 2 0 2 3 3 1 2 3 1 3 3

11.2 2 2 3 3 3 3 3 3 3 3 3

, 6 3 1 3 2 3 2 2 3 2 3 3

11 11,2 3 2 2 3 3 3 3 3 3 3 3

, 6 2 2 2 2 3 2 3 3 3 3 3

12 11.2 3 2 2 3 3 3 3 3 3 3 3

5.6 3 1 1 3 3 2 3 3 2 3 3

13 11.2 - 2 2 2 3 3 3 3 3 3

, 6 - 1 1 1 3 3 2 3 - '3 3

14 11,2 3 1 3 3 3 2 3 3 3 3 3

, 6 O 0 2 3 3 2 3 3 1 3 3

11.2 1 1 2 3 3 3 3 3 3 3 3

5.6 2 0 1 2 2 1 3 2 0 3 3

16 11,2 3 1 2 3 3 3 3 3 3 3

, 6 2 0 0 0 3 2 3 3 3 3 3

17 11,2 3 1 1 0 2 3 3 3 3 3 3

, 6 3 0 2 2 3.2 3 3 3 3 3

18 11,2 3 2 3 3 3 3 3 3 3 3 3

5.6 3 2 2 3 3 3 3 3 3 3 3

19 11,2 3 1 2 2 3 3 3 3 2 3 3

, 6 3 O 2 2 3 3 3 3 1 3 3

  The compounds were further tested using the above procedure for the following plant species: L Soya R Hemp Sesbania M Sugar Beet E Lamb Quarter N Wheat F Beautiful Grass O Rice C Velvet Leaf P Sorghum J Fluffy Brome

B Nielle Fields S Panicum Spp.

  Q Wild Buckwheat K Barnyard Grass D Garden Volubilis T Wild Grass

  The results are summarized in Table III.

  ## EQU1 ## where: ## EQU1 ## H, <a Qa 4> H a> rdf II> ID a> "3 PS Pa m m I m I n m M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M M H M H

<Y) '- 0000

M010 N t-4 H0

I f N N oq o

('im 4 H-0 O riN <HHQ I r> MM4H00

Y> C'0000

he - -

mHOOO ('1 H o o

( "0000

  HMO00 n H 0000 C o 0o 00 Hoooo f- 10 0 0 mmm0 0 mM mN0

M M N00M

nimg0 00 MMMO

MN000000

in cn In 0 r-

(1N O O 00

M00000

MO00

('1 N' H- O Q-

<< 0000

  q rg 0 0 07 0 c'1eH O O in 4 H l O O

<Y <> '4H O O

4HH000

  m mr 10 0 MMN00 C mi i0 00 in ") n ri 0

<Y <_I O O

m N rYl 0 O cn cn m O I m (H O O

H 1I 1 0

   Y) M m M O ('n N <> H O M N N4 ri O M00O0

W'1 (N'1C'400

N1N N'1 O O

MMHOOO

mf r X1 0 1 01 m fo1 0 0 I ire <> 00

<Y> (1 <'HO O O

N1 _10 0 0 0

('> (' 1 ('4C) OH

mmNOOOO

( '(' <'00

  M c n ((((((((((((((

N N HI O O

M N mi 0 O-1

N - 1 0 0 0

<Y> m m> OH m m m r r r

<Y> ("1H Q O

(Y <Y N H O

  MNOOO M m m M N N n n cm n rm mi r-1 (Y <N1 _i1 O O

<Y> ('4 H H O O

("" 1 NY N '<Y> H N

HO 000

<MMH00

mi 0 N N e1 0

HO O 0H 0

  ## EQU1 ## ## STR1 ## ## STR2 ## ## STR1 ## ## STR2 ## ## STR2 ## ## STR2 ##

  % .k %%%% k% k..k% k.k.kk% s% k.kkkk.NkkkkkkNkksk kkksk.

  HOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOOO

- N <Y> Lf r - co -

o-I UH M r-i N M le * Ln 1.m ,, o 9 l

u ---

UL 0 Ln

HI N N

O L

(ir MO eH000

MY in '<Y> <' 4 H-

m N N N N N m m r n -1 N 0 0 0 0

<YC "000

N N <Y 1 I O

<Y> ('4 N' O O

* M MO I CN N r-1 mI

N 0000

- -1 - ----____ _

  t.qm x) 7% -] N -iw <nwo in H uw H o in H HH HHH 'HHHH t oe-1 w H i Co oo cs oo W o Io o OOO 0 0 FiO0 0 -Ln0 0 0 0 0 00 Fn0 0 O'Owu 000 0 0 IJ, 0 0 0 Pn0 0 0 P 0 0 0 0 0 0 0 0 00 0 0 0 0 0 0 N i - cn oo N) wa Fo o - hi W Fi o - oo) w W o o - N) in oo) 1 'o oo I - ch O O - F) b Ni NEO iJ iFJ' 100 NI 0 1w 0- 0-FW OD Nq0 C -0- OCW I1 0F. = 0 0 0t.JH 00t-JHO 00 HO'I 00JHOi OONHOI 00N> HO 00I 00000 w0N 0HG OOO 'wi OOOO wi OOOOOOO O1 0 OO O-ONO OOONOPW O1 0 0 0 po 0 0 0 0 0 1 F-0 0 1 0 0pN O oo, [_ wmw 0000w OOO 0 OOOOH 000 000 O 1 NN W r OOO 0 ION OHN 00000 0 0 NMW 0 0 0 WW OO000W 000HH 00 -0W HH> s) W 0 00HM0 001-. O0W N N1 W 0 0 Jw 0 0tj W W00I 0t - W 00W ON 'W 0 N> WW NOW W 0 MNWWO hi WW WO tvj WNOW WW O 0 W OOWWW WO 0 1-W W 0 0 1N-WWOW W. OWW WW 0 - WWW OH JNWH k WO -N WW O0 F w O OO: - 0 00- H 10000 0 0 F0 O - O Hw0O <1 0J 010 O - W 0 00W 00 001HO O OOOH 000H 1W-NOWW O OOwH000 1NW 00WNW 0000W 0 -00 WJW OOWW 0 0 00 HW 0t0J 0 J0 WW 0W W 00 WWW 0 HN W oOOWw 0OOOOH W OOH OOOW HNWW OO0.j OOOM OOWHN0 00t'NW OM OO WW OI-W 0 1- W NW 1- 1-O WW 1i-WWW OH> WWW WOI-WWW 0 WWW WW W W WWI WNW W OH0O1NW W QHWtWI-01-NW OON) N WW 1-FN WWW O h) WWW NW WWW Ot ' JWN tW1- N OWW ow WwW0 1-WWW H -W t) WW OO W WW O0O tJW WW 1-0 N WW H'W <WWWON> W WW OW W OW WW) WW 0W w aoHJWW w 1WLAW 0 <OOMLi0WW OWWWW OWWW W 0W 0 0WW OWNOtWW WWWWW WWWW 1 WWWWW WWW WWWWW 1 WWWW WWWW 1 1 1 1 1 1 III WWWW W WWW WWW IIIIW (JWWW wwwww wwwww wwwww-1 ww H-HH cf, p-. r1 0% 18.

  The herbicides of this invention have been found

  had superior properties unexpectedly.

  as pre-emergence herbicides -, - more particularly

  the selective control or selective destruction of the hard-to-destroy annual weeds of Texas panicum,

  Johnson, the brittle cane, the herb of Alexander, the prosom-

  wild rice, red rice and tart grass, while

  also eliminating or eliminating many other

  its annuals and perennials less resistant.

  The selective control and the increased weed control mentioned above with the herbicides of the present invention have been found in a large number of

  plants to be harvested, including soya beans, cotton,

  chides, rapeseed and brittle beans (white beans).

  Selectivity has been shown in some tests for various application rates in sugar beets and peas.

  gardens; however, some plants to be harvested, particularly

  plants to be harvested from the grassy genus are usually

  less tolerant to herbicides of the present-

  the invention than the plants to be harvested earlier.

  To illustrate the superior properties of

  unexpected of the compounds of the present invention, both

  on an absolute basis and on a relative basis,

  paratives were conducted in the greenhouse with prior art compounds most closely related by

  their structure to the compounds of the present invention. The com

  Prior art patents are identified as follows: A. Nt-butyl-2-methoxy-2-chloroacetanilide (Example 13, U.S. Patent No. 3,268,584) B. 2'-t-butyl-6'-methoxy-2-chloroacetanilide (Example 67, U.S. Patent No. 3,442,945) C. N-Isopropyl-2-chloroacetanilide (common name "propachlor"): U.S. Patent No. 2,863,752 (Reissue Patent No. 26,961); Propachlor is referred to in US Pat. Nos. 3,773,492 and 1,19.

  4,152,137 mentioned above and is the

  active in the herbicide of known trade

  under the trademark "Ramrod", which is a trademark

  filed by the so-called Monsanto Company.

  In the discussion of the results below, reference is made to herbicide application rates symbolized by "GR" and "GR". These rates are given in kilograms per kilogram.

85

  hectare (kg / ha). GR15 defines the maximum rate of herbicide required

  to produce 15% or less damage to the plants to be harvested, and GR 85 defines the minimum rate required to achieve% inhibition of weeds. The GR15 and

  GR85 are used as measures of

  potential mercury being of course, of course, that suitable commercial herbicides

  less damage to plants within reasonable limits

ble.

  Another guide to the effectiveness of a chemi-

  that as a selective herbicide is the "selectivity factor

  "(" FS ") for a herbicide in given crop plants and in specific weeds Selectivity factor is a measure of the relative degree of safety of the plants to be harvested and weed damage

  and is expressed according to the ratio GR15 / GR85, that is to say

  the GR rate for the crop to be divided divided by the GR85 rate for the weed, both rates being

  kg / ha. In the tables below, the selection factors

  are shown in parentheses after GR85

  for each weed; the symbol "NS" indicates "not separated

  marginal selectivity or criticism is indicated.

  by a hyphen (-); a space left blank means that the indicated plant was not in the test or that the plant

could not sprout.

  Since the tolerance for the plants to be harvested and the control or destruction of the weeds are interrelated, a brief discussion of this relationship according to the selectivity factors is significant. In general, he

  It is desirable that the plant safety factors

  20. colter, that is, herbicide tolerance values,

  are high, since higher concentrations of

  bicides are frequently desired for a reason or for a

  other. Reciprocally, it is desirable that the rates of

  Weed control is low, that is, the herbicide has a high unit activity, for economic and possibly ecological reasons. However, low rates of herbicide application may not be adequate to control some weeds and a higher rate may be required. As a result, the best herbicides are those that control the most weeds with the least amount of herbicide and provide the highest level of plant safety.

  to harvest, that is to say the tolerance to the plants to harvest.

  Consequently, the "selectivity factors" (

  finished above) to quantify the relationship between security

  for the plants to be harvested and weed control. By referring to the selectivity factors shown in the tables, the higher the numerical value, the greater the selectivity of the herbicide for controlling

  weeds in a given crop.

  In a first comparative test, data from

  pre-emergence herbicide activity in greenhouses are

  shown in Table IV, comparing the relative potency of the compound of Example 1, which is a representative compound of the present invention, with compounds of the prior art, namely compounds A, B and C, as

  selective herbicides against specific weeds

  commonly associated with soybeans. Experimental results

  The rates in Table IV for all compounds were obtained under identical experimental conditions, i.e. by incorporation into the soil with initial initial irrigation; the results represent the averages of two

  duplicate tests for each compound; two samples

  different from the compound of Example 1 were used and

  the results in the table represent the average

  two experimental samples. The bad ones

21.

  used in the test here have the following abbreviations

  in the paintings: Texas panicum (TP), young plants

  johnson grass (SJG), brittle cane (SC), Alexandrian herb

  dre (AG), wild prosomillet (WPM), fall panicum (FP), red rice (RR) and picot grass (IG). rt C'j AI aVqaIVi (9'OTI) LO'O (6'ú) 9T'O ('EtOO Tsf'O: o) OQZ'0QT <) LO'cÄ Z'OT <) LO'O> (9 # 9) TT'O TL'O T.XS _ _ _ _ _ _ W d M 1 6) Z "_ _ _ _ _ _ _ <_ _ _ _, T <CO S0 U </ bx) -WoD (4 / Bf) GT E 23. Referring to the results in Table IV, it will be seen that, compared to weed control, no

  compounds of the prior art did not exhibit a

  positive and selective control of weeds against

  what weed in soybeans at the maximum rate of application

  application, that is to say 1.12 kg / ha, but, with the exception

  of the compound C against fall panicum, and even in this case, the selectivity factor was once less than that for the compound of Example 1. In marked contrast, the compound

  example 1 selectively controlled each bad

  be in the test at extremely low rates of application, while maintaining safety for soybeans up to 0.71 kg / ha. It is particularly noted that the compound of Example 1 controlled young Johnson grass plants, brittle cane, Alexander grass, fall panicum and tart, at the rate of 0.07 kg. / ha (the minimum rate

  used) or less, and also controlled the bad her-

  bes remaining, that is to say the Texas panicum, the prosomillet

  wild, and red rice at only equal rates respectively

at 0.10, 0.14 and 0.18 kg / ha.

  Additional tests were conducted in the greenhouse to compare the relative herbicidal efficacy of the prior art compounds with the

  examples 1, 3-5 and 8-17 as an illustration of the

  of the present invention. The tests were conducted by

  in the soil of the herbicide at rates of application

  in the range of 0.07 to 1.12 kg / ha and initial irrigation

  from above, followed by humidification by irrigation

  Subsequent observation from below, as necessary. Observations were made 19 days after treatment. The results from the additional tests are shown in Table V; weed names are indicated

  abbreviated as in Table IV and the selection factors

  are shown in parentheses after GR85

for each weed.

(5 'I <) SLI0

(0 ') 8Z' 0

(0 '<) 8Z'0

(0 '8) L0'0

(Z'Z) OS'o

(ú'Z <) 89 "0

(0 'Z <) 9 S' O

(Z '<) OS'O

(SN) Zl '' [<

(0 '1 <) ZI O

(01 89 <) T'1'0

  (9'8 <) ET'o (S '<) SZ'o (0'14 Zl'1I (-) Zl' 1 <

(-) ZT 'T <

(0 '9T <) Lo'o>

O '9T <) LO'OC

(0 '91 <) L0'C>

0 '91 <) LO'C0

(O '91 <) LO'C>

O '9t <$ LO'C

(0 '91 <) LO' 0>

(0'91 <) LO'O>

(0 '91 <) L0'0>

O '9I) LO'O>

O '9I LO'O>

(0 't <) Z'O0

(0 '1 <) 00' 1

(-) ZT '1 <

(0 'Z <) 9S'0

(0 '1') 9Z'0

(0 'Z <) 95'0

(0 '1) 9S'0

(0 ') 8Z'0

(0 '' <) aZ'0

(0 'Z <) 9S'0

(0 '9 <) 8Z'0

(0'l) ZI'I

(0 '1, <) 8Z'0

(0'8 <) T1'0

(0 't <) Z' 0

(0'8 <) 1T'10

(O ') I' I

(-) ZI 'I <

(-1 Zl'T <(ú'6 <) Zl '0

(0 'ZT) 60' 0

(O 'Z <) 9S'O

(O 'Z) gZ'O

(0 'ú) 8;' 0

(0'4 nT'O0

(0'ZE) 60'0

O 'ZI <) 60'0

<O '<) 60' 0

(O'9) bl'O

(O '91 <) LO'O>

(O '91 <) LO'0

', 91 <) 1.010>

O '91 <) LO' 0

O'91 <) LO'O

(0'1 <) ZT'I

(0 '1 <) 00' 1I

(-) ZT 'T.'

(0Il <) T'O0

(0'8) V1 '0

(0 'T <) ZT' I

(0 '') Z'CO

(O '9) 8Z'0

(0 'Z) 8Z' 0

(9 'S <) 0z'0

(0 '<) 8Z'O

(0 '91 <) 8LO'0

(Z'Z) OS'O

O 'ZTC) 60'0

O '91 <) LO'O>

(O''91C) LO'O

(0 '8 <) L1'0

(0'91 <) LO'0>

(-) Z Tl 'I' (-) Zl 'I <

(-) ZT 'T <

(0'1 '<) 9Z'0O I (0'Z <) 9S'O

(0 '9) LO'CP

(6'S <) 61'02

(0 '8) LO'>

(0 '8) b''O

0 '91 <) L0' 0

0'1C) 0'0 |

0'9I <) L0'0

(0'8) 1T'0

O'91 <) LO'O

(0'9T <) LO'I

O0'91 <) LO '

0 '91 <) LO'O>

O '9I <) lO'O>

O '9I <) LAW O>

(-) Zl T '<

(-) E 7T 'I <

(- 7.T 'T <

(0'r) 8Z'0

(0'Z <) 9S'0

  (0O ') tl'O (0o'r) 89:' 0 (0 '<) ez' 0

(0 <) 8Z'0

(0O '<) 9Z'0

(O ',') 8Z'0

(0 '8 <) PT'0

O'9T <) L0'0

O'ZT <) 60'0

0'91 <) L0'0

O'9T <) L0'0>

(0'1 <ZI 'I

(-) Z 'I <

(-) ZT'T <

- - q - - I-- **. - t - - - -

  or (q / B <) /5.X) qsod A ViEVrla, * Q) * -t ZT'I '0 Z1'1 Z!' I! Z! ' 1 <l

ZT T '<

ZT 'T <

  Zl'l EI'I <Zl't <Z 1 <z T '1 <Z Ir <LL-XS <* X X 9'X DI'x. 6'X.L 8'xa T. xa P.xa C 'xa T-XA D V 25.

  Referring to the results in Table V, we

  that, within the limits of the experimental herbicide

  compounds, compound A did not selectively control any of

  experimental weeds in soybeans, compound B controlled only selectively marginally

  fall panicum (which is not a particular weed)

  particularly resistant) and compound C controlled selectively

  only the fall panicum and, marginally, the

  Texas panicum, Alexander's herb and red rice. At the only

  With the exception of Compound C against fall panicum (GR85 equal to 0.28 kg / ha), and Compound B against Alexander grass and - fall panicum (GR85 = 1.00 kg / ha), none compounds of.la

  prior art did not control any of the

  herbs in the test at less than 1.12 kg / ha.

  In a strongly opposed way, if not in

  isolated cases against certain weeds, all the components

  of the present invention had a selective control

  remarkable positive tif of each weed in soybeans.

  In only a few cases, selective control was marginal, for example that of the coexposites of Examples 8 and 7: against red rice, of Example 9 against wild prosomillet and red rice, of Example 14 against the wild prosomillet and the exemnle against the brittle cane. Again, as opposed to the prior art compounds and again with the noted exceptions, all compounds of the present invention controlled all weeds at extremely low rates of application, ranging from no greater than 0 , 56 kg / ha, decreasing to less than 0.07 kg / ha, which is a remarkable performance in absolute terms due to the highly resistant nature of the weeds tested (with the exception of fall panicum) and particularly with respect to the inability of most of the most valuable compounds of the prior art to control any of the weeds

  experimental except as noted above.

  Preferred compounds of the present invention have

  have been tested in the field to determine their

  pre-emergence herbicide and their longevity 26. in soil against the annual weeds of Texas panicum, the hairy little burdock

  the so-called Florida pusley grass in peanuts (Florunner).

  Observations were made after 4.8 and 12 weeks.

  after treatment (SAT) by surface application of herbicides; the soil type was a sandy Soil called Dothan with 1.3% organic matter; the results are

presented in Table VI.

TABLE VI

  Percentage inhibition in Peanuts Texas panicumn Small Burdock Florida Pusley Com-_oil Hairy

Com- Rate._. ....

  laid kg / ha 4 SAT 8 SAT 12 SAT 4 SAT 8 SAT 12 SAT 4 SAT 8 SAT 12 SAT 4 SAT 8 SAT 12 SAI Ex.1 1,12 O 0 O 85 6052 - 80 85 -95

  2.24 12 5 0 93 83 83 - 90 95 95 90 95

3.36 22 13 0 95 97 87 - 97 95 98 98

  4.48 40 27 21 100 95 98 95 100 98 100 98 98

  Ex.2 1,12 O O O 82 58 62 - 80 80 - 90 -

  2.24 3 3 O 90 88 87 95 95 90 95 95 100

* 3.36 8 10 O 95 95 92 - 90 95 - 97 95

  4.48 15 15 15 98 100 100 - 100 100 - 98 95

  Ex.3 1.12 10 O 0 78 78 43 - 85 - - 85 70

2.24 15 10 0 92 87 70 - 88 - - 98 -

3.36 27 13 0 95 93 88 95 95 - 98 95

  4.78 37 27 13 100 97 90 - 97 95 - 98 100

  at. Average of three trials conducted in duplicate.

  The results in Table VI show that

  set of Example 2 selectively controlled all three weeds in peanuts at rates in the range

  from 2.24 to 4.48 kg / ha for up to 12 SAT.

  Selective control of one or more of the experimental bad herbs was also presented by the compounds

  examples 1 and 3 at lower rates for a period of time

  up to 12 SAT, indicating that among the three test compounds, the compound of Example 2 had the greatest safety factor in peanuts under the conditions of

this is.

  Other tests were again conducted in the field

  to determine the relative effectiveness of the compounds of the

  ples 1, 3 and 4 against wild prosomillet in soybeans,

  for up to 12 weeks after treatment

  by applying it either as over-the-top applications

  face (SA), either by incorporation before the plant (PPI). The

  soil was a sandy loam with 1.7% organic material

  lunch; a 6.35 cm rainfall occurred 2 days after treatment; the results of this test are presented

in Table VII.

TABLE VII

  r \ -Pl -o. or Co Percentage of inhibition a -__ -_ soya _ ___-___-_ Prosomillet sauvae

  3 TSAT 8 12 SAT2S 8 AT 3SAT8AT 12 SAT

  How much does it cost? PPI SA PPI SA PPI SA PPI SA PPI PI laid kg / ha Ex.1 1,12 15 32 0 22 0 0 85 82 40 43 25 18

  2.24 15 33 0 33 0 0 92 78 78 48 77 50

  3.36 15 32 13 32 0 10 95 85 90 60 85 60

  4.48 33 50 20 30 8 23 98 92 85 78 78 70

  Ex.2 1,12 0 27 0 8 00 85 73 60 57 25 20

  2.24 15 37 0 25 0 5 92 75 68 53 72 43

  3.36 22 40 7 27 0 0 95 87 88 70 85 63

  4.48 30 60 13 47 7 8 92 88 88 70 83 62

  Ex.3 1.12 8 15 5 10 0 0 95 85 68 55 63 10

  2.24 15 22 7 18 0 0 95 85 80 67 58 47

  3.36 22 25 10 18 0 0 95 80 82 50 82 42

  4.48 22 43 15 33 0 30 95 90 90 78 85 58

  at. Three-fold average yield was obtained. The results in Table VII show that a rate of 3.36 kg / ha of each compound selectively controls wild prosomillet in soybeans for 3.8 and 12 SAT in soybeans.

  surface applications. Thus, some treatments of the

  to be harvested with the compounds of the present invention

  long seasonal checks of the wild prosomillet

  ge, since the germination and emergence of this species increases

  gradually melt as the season unfolds. It was estimated that the greatest degree of soybean damage in PPI treatments was due to excessively deep and uneven incorporation by the sprayer and

  Rainfall occurs two days after treatment.

  In this test, the surface application treatments

  had superior weed control and a

  superior safety for the plants to be harvested.

  In another test in the field, the compounds of

  Examples 1, 3 and 4 were tested to determine their

  herbicide on the very hardy annual weed of young Johnson grass plants, with

  herbicide treatments by surface application and incorporating

  ration before the plant. This test in the field was conducted

  in clay soil (58% clay and 3.1% organic matter).

  nic). Observations were made after 4 and 8 weeks after treatment; the results are presented in

Table VIII.

TABLE " 'VIII

  Percentage inhibition in Young grass seedlings

_Soja _ _ Johnson ___-

  Com- Rate 4 SAT 8 SAT 4 SAT 8 SAT Posed kg / ha PPI 1 S P SA PPI; SA 1 PPI has SA Ex.l 1,12 5 3 12 3 7 23 _ 10

2.24 13 12 28 10 75 67 85 80

3.36 23 15 22 17 78 85 87 80

4.48 30 18 38 22 - 80 85 93 78

Ex.31,12 10 3 13 5 17 25 O 23

2.24 22 13 13 7 47 67 70 60

3.36 28 18 22 15 70 82 85 78

4.48 32 22 32 23 78 78 90 68

  31. TABLE VIII (Continued) Ex.4 1.12 10 0 8 0 7 23 33 8

2.24 13 13 8 12 60 68 85 78

3.36 23 12 20 13 73 82 87 88

4.48 22 17 28 15 75 85 88 85

  at. Average of 3 trials done in duplicate. The compound of Example 4 selectively controlled Johnson seedlings in soybeans at a rate of 2.24 kg / ha for as long as 8 weeks after treatment under PPI conditions and at a rate of 3 , 36 and 4.48 kg / ha under conditions of application in

  area. The compounds of Example 1 controlled selectively

  seedlings of Johnson grass at a rate of 3.36 kg / ha for at least 4 weeks after

  surface application conditions.

  Comrcme indicated by the results in the tables

  above, the compounds according to the present intention are

  used by surface application treatments.

  this or incorporation into the soil, the preferred treatments de-

  during various factors such as soil, climate, etc.

  However, generally, the surface application of herbicides

  This is preferred for incorporation into the soil.

  In laboratory tests to determine the

  the herbicide to soil leaching and the effectiveness of

  As a resultant herbicidal site, the compound of Example 1 was formulated

  macerated in acetone and then sprayed at different concentrations

  on a weighed quantity of loamy soils called Ray con-

  held in pots having a filter paper covering the drainage holes in the bottoms of the pots. The pots containing the treated soil were leached by placing them on a table

  rotating under two nozzle tips of a recess

  calibrated water to provide 2.5 cm of water per hour to

  emulate a rainfall. The leaching rates were set by varying the time on the rotary table. The water has been

  provided in the pots and allowed to percolate through

  to filter paper and drainage holes. We left -

  then the pots resting for three days at the temperature

  room. The soil treated in the pots was then removed,

32.

  gregated and placed as a surface layer above

  pots containing loamy loam soil called Ray

  started with barnyard grass seeds. The pots were then placed on greenhouse benches, irrigated from below, and seed growth allowed to proceed for

  2-3 weeks. Visual assessments of the percentage of inhi-

  growth habit, compared to control pots (untreated) and fresh weights for backyard grass, were made 18 days after treatment and recorded; results from three duplicate trials

  for these tests are shown in Table IX.

TABLE IX

  Barnyard Grass Compo- Rain Rate Percentage Fresh Weight Percentage Seed (kg / (cm) Control Inhibition I

  example) (average of 3 tests carried out

duplicate duplicate)

2.24 O 100 O 0

0.64 100 O O

1.27 100 O O

2.54 100 O 0.08 100 0 O

, 16_ 95 0 O

0.56 0 100 O O

0.64 100 0 0

1.27 100 O O

2.54 100 O O

, 08 95 0 O

, 16 95 0 0

0.14 0 100 O 0

0.64 100 O O0

1.27 100 0 0

2.54 95 0 0

, 08 95 0.20 3.3

, 16 90 0.83 14.1

  The results in Table IX indicate that the compound of Example 1, as an illustration of the compounds of the present invention, was very resistant to soil leaching under conditions of heavy rainfall and

  had not less than 90% control of grass

  at application rates as low as 0.14 kg / 33.

ha under 10.16 cm of rainfall.

  A distinct advantage of a herbicide is its ability to

  to operate in a large number of soil types. In

  Consequently, data are presented in Table X

  the herbicidal effect of the compounds of Examples I and 3 on Alexander's herb (AG) and backyard grass (BYG) in soybeans in a variety of soil types and organic matter contents. . Herbicide treatments were applied by surface application with

  the top, as described above; the selectivity factors

  for weeds are presented in brackets

  its after the GR85 rate for weeds.

PAINTINGS

  Rate i Rate GR 85a GR a (kg / ha) Soil type Material Clay Sojas AG BYG and organic compound% i

and cm, that,%, ..,.

Soil

he said Ray

Example 1

Example 3

Terreau ar-

gileux says Sarpy

Example 1

Example 3

Terreau ar-

gileux li-

he said Drummer

Example 1

Example 3

Florida Sand

Example 1

Example 3

Florida manure

Example 1

Example 3

1, o 2.3 6.0 6.8 22.1 9.6 37.0 1.8

1.12 <0.14

1.12 <0.14

<2.24 <2.24

(> 8.0)

(> 8.0)

0.28 (> 8.0)

0.21 (> 10.7

2.24 <0.14 (> 16.0

<2.24 <0.14 (> 16.0

1.12 <0.14 (> 8.0)

1.12 0.28 (4.0)

2.24 2.24

1.12 (2.0)

2.24 (1.0)

0.14 (8.0)

<0.14 (> 8.0)

0.96 (> 2.3)

0.42 (> 5.3)

0.24 (> 9.3)

0.28 (> 8.0)

1.12 (1.0)

2.24 (NS)

2.24 (1.0)

<2.24 (NS)

34. TABLE X (Continued)

Terreau ar-

oily sand

  Brazilian Bravo (Sao Paulo) 17.6 20.0 Example 1 1.12 <0.14 (> 8.0) 0.14 (8.0) Example 3 1.12 X 0.14 (8.0) ) 0.14 (8, O) a. The results represent the averages of two duplicate trials. The observations were made 13

days after treatment.

  The results in Table X show that

  poses of the present invention were largely insensitive

  to the type of soil. More particularly, the compound of the

  ple 1 exhibited positive selective control of Alexander's herb and barnyard grass in soybeans in all soils in the test containing organic matter

  the content of which is 1.0% organic matter in the

  silty water called Ray at 22.1% organic matter in the

  soil consisting of manure (garbage) from Florida. In a

  blable, the compound of Example 3 exhibited a selective control

  of the weeds in the soja test in all soil types, with the exception of the test against

  barnyard grass in the Florida sand (6.8% of

  organic matter) and in Florida manure. Since the compound of Example 3 selectively controlled both

  Alexander's grass and barnyard grass in the soil

  loamy loam soils called Drummer, having

  approximately the same organic matter content as Florida sand, but a much higher clay content (37.0%)

  and in soils with a higher organic matter content

  and a higher clay content, as in the

  Brazilian sandy loam, it is believed that the low tis-

  clay (1.8%) in the Florida sand contributed to the

  non-selective control of barnyard grass in this soil.

  The compounds of the present invention have their application

  the most important cation in soja and arachi-

  of. However, selective control of weeds has been established in a large number of other plants to be harvested, as shown in Table III above. In other

  tests, it has also been shown that the compound of the

  ple 1 was useful in brittle beans and peas

  gardens at rates up to 1.12 kg / ha, in the

  colza, carrot and beetroot at rates up to 0.56 kg / ha or more and in alfalfa, flax

  and cabbages at rates of the order of 0.28-0.56 kg / ha.

  Toxicological studies on the compounds of the

  ples 1, 3 and 4 indicated the following properties

-

  Toxicology C ___ dare of example n0

1 3 A

  LD50, mg / kg 3370 2300 2400 DLD, mg / kg> 2000> 1000 <1260> 3100 <5010 Eye irritation Slight Significant Moderate Skin irritation None Corrosive Corrosive to corrosive nature of the compound of Example 3 may be due to a contaminant, dimethyl sulfate, found in the sample preparation on which toxicological studies were conducted. It appears that the above compounds can be safely used with the normal degree of care required for compounds having

  the toxicological properties indicated. The relative degree

  of safe handling characteristics for

  of the respective examples seems to be: example l> example

4> example 3.

  Accordingly, it will be appreciated from the description of

  previous detail, that the compounds according to the present

  The invention has shown unexpected and remarkably superior herbicidal properties at the same time. absolute and relative to the compound the most interesting from the structural point of view of the prior art, one of which (the

  compound C) is a commercial herbicide. More specifically

  The compounds of the present invention have been found to be remarkable selective herbicides, particularly for the control of annual weeds which are difficult to kill in the 36s, soybeans, peanuts and other crops to be harvested. More

  particularly, the compounds according to the present invention

  have a remarkable control of the annual herbs

  killed by the Texas panicum, the prickling grass, the prosomi-

  let wild, Alexander's grass, young grass seedlings

  Johnson, the brittle cane and the red rice, while controlling

  and / or by removing other less resistant annuals

  aunts and perennials including those mentioned in Tables II and III above and others, such as hairy little burdock, Florida pusley grass, etc.

  The herbicidal compositions of the present invention

  The composition, comprising concentrates which require dilution prior to application, contains at least one active ingredient and an adjuvant in liquid or solid form. The essays

  are prepared by mixing the active ingredient with an adjuvant

  including diluents, extension products (charcoal

  (ges), carriers and conditioning agents for

  compositions in the form of finely divided particulate solids, granules, pellets, solutions, 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

  any suitable combination of these products.

  The compositions of the present invention, particularly

  liquids and wettable powders, contain

* preferably, as a conditioning agent, one or more

  surfactants in sufficient quantities to

  a given composition easily 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, and anionic, cationic and nonionic agents may be present.

  used with equal ease.

37.

  The preferred wetting agents are alkyl-

  benzenes and alkylnaphthalenesulfonates, sulfated fatty alcohols, amines or acid amides, esters of long-chain sodium isethionate acids, sodium sulfosuccinate esters, sulfa fatty acid esters,

  sulphonates, petroleum sulphonates, vegetable oils and

  sulphonated tetals, acetylenic ditertiary glycols,

  polyoxyethylene derivatives of alkylphenols (especially

  isooctylphenol and nonylphenol), and polyoxyethylene derivatives of monocarboxylic fatty acid esters

  of hexitol anhydrides (eg sorbitan).

  The preferred dispersion products are methylcellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkylnaphthalenesulfonates, naphthalenesulphonate

  of sodium and polymethylene bisnaphthalenesulphonate.

  Wettable powders are dispersive compositions

  sands in water containing one or more ingredients

  an inert solid extension or dilution product and one or more wetting and dispersing agents. The

  extension products-inert solids are ordinarily

  mineral, such as natural clays, diatomaceous earth and synthetic minerals from silica and the like. Examples of these extension products or

  dilutions include kaolinites, the so-called attapulgi-

  te and synthetic magnesium silicate.The compositions

  wettable powder of the present invention contain orally

  typically from 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 agent, about 0.25 to 25 parts by weight. parts (preferably 1.0-15 parts) of dispersion product and 5 to about 95 parts (preferably 5-50 parts) of inert solid extension product, all

  parts being by weight relative to the total co-operation.

  When required, about 0.1 to 2.0 parts of the inert solid extension product may be replaced by a

  corrosion inhibitor or defoamer or both.

  Other formulations include dust concentrates comprising 0.1 to 60% by weight of the active ingredient on a suitable extender; these dusts can be diluted for application in concentrations

  in the range of about 0.1-10% 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 they are uniform and then homogenized to give a stable emulsion. very finely divided particles. The resulting concentrated aqueous suspension is

  characterized by its extremely small particle size

  so that, when diluted and sprayed, the

  recovery is very uniform. Appropriate concentrations

  These formulations contain about 0.1-60%, preferably

  5-50% by weight of active ingredient, the upper limit

  is determined by the solubility limit of the

active ingredient in the solvent.

  In another form of aqueous suspension, a herbal

  water immiscible bicide is encapsulated to form a microencapsulated phase dispersed in an aqueous phase. In

  an example embodiment, tiny capsules are

  by bringing together an aqueous phase containing an emul-

  lumpy lignin sulphonate, a chemical

  immiscible with water and polymethyl polyphenyl isocyanate

  by dispersing the immiscible phase with water in the phase

  is aqueous, followed by addition of a polyfunctional amine.

  The isocyanate and amine compounds react to form a solid urea shell wall around the water-immiscible chemical particles, thereby forming microcapsules. Generally, the concentration of the microencapsulated material will be increased. about 480 to 700 g / l of composition

  total, preferably 480 to 600 g / l.

  Concentrates are usually active ingredient solutions in water-immiscible solvents

  or partially immiscible with water with a surfactant

  active. Suitable solvents for the active ingredient of

  the present invention include dimethylformamide, di-

  39. methylsulfoxide, 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 kerosine

  no, up to the spray concentration.

  The concentrate compositions here generally contain

  from 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 and, where this is

  ge, about 4 to 94 parts of solvent, all parts

  being by weight based on the total weight of the emulsified oil

  sionnable. The granules are physically stable particulate compositions comprising an active ingredient adhering to or distributed through a base matrix formed by

  an inert particulate extension product, finely divided.

  To help leach the active ingredient from the

  particulate product, a surfactant, such as those

  previously identified, may be present in the composition.

  Natural clays, pyrophyllites, illite and vermiculite are examples of well functioning class of particulate mineral extension products. Products

  preferred dilution or extension are the particles

  porous absorbers, such as attapulgite parti-

  preformed and sieved eyelet, or particulate vermiculite

  thermally expanded, and finely divided clays such as kaolin clays, hydrated attapulgite or bentonite clays. These extension products are sprayed or mixed with the active ingredient to form

herbicidal granules.

  The granular compositions of the present invention

  It may contain from about 0.1 to about 30 parts, preferably from about 3 to 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 for 100 parts in

weight of particulate clay ..

  40. The compositions of the present invention may also contain other additive products, for example, fertilizers, other herbicides, other pesticides,

  and analogues used as adjuvants or in combination with

  with any of the adjuvants described above.

  Useful chemicals in combination with the ingredients

  Active ingredients of the present invention include, for example,

  ple, triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic acid or phenol derivatives, thiolcarbamates, triazoles, acids

  benzols, nitriles, biphenyl ethers and the like

  such as: Nitrogen / sulfur-containing heterocyclic derivatives 2-chloro-4-ethylaftin-6-isopropylamino-s-triazine 2-chloro-4,6bis (isopropylamino) -s-triazine 2-chloro-4,6-bis (ethylamino) ) -s-triazine

  3-isopropyl-1H-2,1,3-benzothiazole 2,2-dioxide

  diazin-4- (3H) -one 3-amino-1,2,4-triazole

  the salt of 6,7-dihydrodipyrido (1,2-a: 2 ', 1'-c) -pyrazi-

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

  N '- (4-chlorophenoxy) phenyl-N, N-dimethylurea

  N, N-dimethyl-N '- (3-chloro-4-methylphenyl) urea 3- (3,4dichlorophenyl) -1,1-dimethyl-1,3-dimethyl-3- (2-benzothiazolyl) urea 3- (p-chlorophenyl) -1,1-dimethylurea 1-butyl-3- (3,4-dichlorophenyl) -1-methylurea carbamates / thiolcarbamates 2-chloroallyl diethyldithiocarbamate N, N-diethylthiolcarbamate S- (4- chlorobenzyl) isopropyl N- (3-chlorophenyl) carbamate

  S-2,3-dichloroethyl N, N-diisopropylthiolcarbamate

  allyl ethyl N, N-dipropylthiolcarbamate 41. S-propyl dipropylthiolcarbamate Acetamides / acetanilides / anilines / amides 2-chloro-N, N-diallylacetamide N, N-dimethyl-2,2-diphenylacetamide N- (2,4-dimethyl-5 - [[(trifluoromethyl) sulfonyl] amino] phenyl) acetamide N-isopropyl-2chloroacetanilide 2 ', 6'-diethyl-N-methoxymethyl-2-chloroacetanilide

  2'-methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-

chloroacetanilide

  a, a, a-trifluoro-2,6-dinitro-N, N-dipropyl-p-tolui-

dine

  N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide.

  Acids / Esters / Alcohols 2,2-dichloropropionic acid 2-methyl-4chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid methyl 2- [4- (2,4dichlorophenoxy) phenoxy] propionate acid 3- amino-2,5dichlorobenzoic acid 2-methoxy-3,6-dichlorobenzoic acid 2,3,6trichlorophenylacetic acid

  5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitro-

  sodium benzoate 4,6-dinitro-o-sec-butylphenol N- (phosphonomethyl) glycine, its monoalkyl (C 1-6) amine salts, its alkali metal salts and their ether ether combinations of 2, 4-dichlorophenyl-4nitrophényle

  2-chloro-α, α, α-trifluoro-p-tolyl-3-ethoxy-ether

  4-nitrodiphenyl Miscellaneous products 2,6-dichlorobenzonitrile methanearsonate monosodium acid disodium methanearsonate Useful fertilizers in combination with the active ingredients 42. include, for example, ammonium nitrate,

  urea, potassium carbonate and superphosphate. On au

  Useful additives include materials in which plant organisms take root and grow, such as compost, fertilizer, humus, sand

and the like.

  Herbicidal formulations of the types described above

  above are given as examples in examples

  illustrative embodiments below.

  I. Emulsifiable Concentrates - A. Compound of Example No. 1 Calcium dodecylbenzenesulphonate / polyoxyethylenethers (eg, product known under the tradename Atlox 3437F) Monochlorobenzene C9 aromatic hydrocarbons B. Compound of Example No. 3 Dodecylsulfonate Mixture Calcium / alkylarylpolyetheralcohol Solvent consisting of C 9 aromatic hydrocarbons. Compound of Example No. 4 Calcium dodecylbenzenesulphonate / polyoxyethylene ether mixture (for example, so-called Atlox 3437F) Xylene II. Liquid concentrates% by weight, 6.0 29.7 29.7, 00.0 4.0 11.0, 00.0 1.0 94.0.00 A. Compound of Example No. 5 Xylene B. Compound of Example 6 Dimethylsulfoxide% by weight, 0.0, 0.0, 0.04, 43. C. Compound of Example 18 N-methylpyrrolidone D. Compound of Example 19 Ethoxylated Castor Oil Product called Rhodamine B Dimethylformamide III. Emulsions A. Compound of Example No. 7

  Polyoxyethylene block copolymer

  ne / polyoxypropylene with butanol (e.g.

  product known as Tergitol XH) Water B. Compound of Example No. 8

  - Polyoxyethylenated block copolymer

  ne / polyoxypropylene with butanol Water% by weight, 4.0 56.0, 00.0 3.5 91.5, 00 IV. Wettable powders A. Compound of Example No. 9 Sodium lignosulfonate N-methyl-N-sodium oleyl-taurate Amorphous silica (synthetic) B. Compound of Example No. 10 Sodium dioctyl sulfosuccinate Calcium lignosulfonate Amorphous silica (synthetic) % by weight, 0 3.0 to 71.0, 00, 0 1.25 2.75 16.00, 00, 0, 0, 00, 0, 0 0.5 74.5

: 100.00

  44. C. Compound of Example No. 11 Sodium Lignosulfonate N-methyl-Noleyl-Sodium Taurate Kaolinite Clay V. Dust A. Compound of Example No. 12 Attapulgite B. Compound of Example No. 13 Montmorillonite C Compound of Example No. 14 Bentonite D. Compound of Example No. 15 Diatomaceous earth% by weight 2.0 98.0, 00, 0, 0, 00, 0, 0, 00 1.0 99.0 , 00 VI. Granules A. Compound of Example No. 16 Granular Attapulgite (passing through a screen having a mesh size of between 0.841 mm and 0.420 mm, ie 20-40 mesh) B. Compound of Example No. 17 Diatomaceous earth (passing through a sieve with a mesh size of between 0.841 mm and 0.420 mm) C. Compound of Example No. 18 Bentonite (passing through a sieve with a mesh size of 0.841 mmn to 0.420 mm)% by weight, 0.0, 0.00%, 0, 00 0.5 99.5, 00, 0 3.0 1.0 86.0, 00 45. D. Compound of Example No. 19

  Pyrophyllite (passing through a sieve

  mesh size between 0.841 mm and 0.420 mm), 0.000 VII. Microcapsules A. Compound of Example No. 1 encapsulated in a polyurea shell wall

Sodium lignosulfonate (e.g.

  Reab product 88B) Water B. Compound of Example 3 encapsulated in a polyurea shell wall Potassium lignosulfonate (e.g. product known under the tradename Reax C-21) Water C. Compound of Example 4 encapsulated in a polyurea shell wall Magnesium salt of lignosulfate (product known under the tradename Treax% by weight 49.2 0.9 49.9, 00, 0 0.5 89, 5, 00, 0

LTM) 2.0

Water 18.0

100.00

  When operating according to the present invention,

  effective amounts of the acetanilides of the present invention.

  are applied to the soil containing the plants, and are incorporated into aquatic environments, in any suitable manner. The application of liquid compositions and

  particulate solid compositions on the ground can be achieved

  by conventional methods, for example with

  Mechanical dust forming machines, telescopic and handheld spraying devices and spray dusting devices. The essays

  can also be applied from aircraft, under

  from dust or spray, as a result of their effectiveness at low doses. The application of herbicidal compositions to aquatic plants is ordinarily carried out by adding the compositions to aquatic environments in the zone or surface where the control of aquatic plants

is desired.

  The application of an effective amount of the compounds

  of the present invention instead of the bad ones

  its unwanted herbs is essential and critical for the practice of the present invention.The exact amount

  of active ingredient to be employed depends on various factors, including

  taking the plant species and its stage of development, the

  type and condition of the soil, the amount of rainfall and

  specific tanilide used. In a pre-emerald application

  plant or soil selectivity, a dose of 0.02

  Preferably, about 11.2 kg / ha, preferably about 0.04 to about 5.60 kg / ha, or suitably 1.12 to 5.6 kg / ha acetanilide is usually employed. Lower or higher rates

  may be required in some cases. An experienced person

  in the art can easily determine from this

  description, including the example above, the optimal rate

  mum to apply in any particular case.

  The term "soil" is used in its broadest sense.

  to understand all the classical "soils", as defined by

  nis in the New Webster International Dictionary 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 the

  but also compost, fertilizer, manure (garbage), humus, sand and the like, suitable for

plant growth.

  The present invention is not limited to the examples of 47.

  realization which has just been described, it is on the contrary

  subject to variations and modifications which

to the man of the art. -

48.

Claims (9)

  1 - Compounds characterized in that they have the formula: o i. C1CH2C A R R2 0 R   R3 o R is methyl or ethyl; R1 is a C16 alkyl radical; R2 is methyl, ethyl or t-butyl, and R3 is hydrogen or methyl in the meta position; provided that:   when R is the ethyl group, R1 is the n group   butyl, R2 is methyl and R3 is hydrogen;   when R3 is the methyl group, R and R2 are also   the methyl group and R1 is the isopropyl or n-butyl group; when R3 is hydrogen and R and R2 are both   the methyl group, R1 is the ethyl group, n-propyl group, iso-   propyl, n-butyl, isobutyl, sec-butyl, n-pentyl, isopropenyl   tyl, 2-methylbutyl, 1-methylpentyl, 2-methylpentyl or 1,3-dimethylbutyl;   when R2 is the ethyl group, R is the methyl group   thyl and R1 is the isopropyl group, and when R2 is the t-butyl group, R and R1 are all two the methyl group.   2 - Compounds according to claim 1, characterized in that R1 is a C35 alkyl radical and R and R2 are methyl radicals.   3 - Compound according to claim 2, characterized in   what it consists of N-methyl-2'-isopentyloxy-6'-   methyl-2-chloroacetanilide. 49. 4 - Compound according to claim 2, characterized   in that it consists of N-methyl-2'-n-propoxy-6'-   methyl-2-chloroacetanilide. - Compound according to claim 2, characterized in that it is constituted by N-methyl-2'-n-butoxy-6'-methyl-2-chloroacetanilide. 6 - Compound according to claim 2, characterized   in that it is composed of N-methyl-2'-sec-butoxy-6'-methyl   thyl-2-chloroacetanilide. 7 - Compound according to claim 2, characterized   in that it consists of N-methyl-2'-isopropoxy-6'-   methyl-2-chloroacetanilide. 8 - Compound according to claim 2, characterized in   what it consists of N-methyl-2'-isobutoxy-6'-methyl- 2-chloroacetanilide.   9 - Compound according to claim 1, characterized in   it consists of N-ethyl-2'-n-butoxy-6'-methyl-   2-chloroacetanilide. - Compound according to claim 1, characterized in   what it consists of N-methyl-2'-isopropoxy-6'-ethyl-   2-chloroacetanilide. 11 - Herbicidal composition, characterized in that it comprises an adjuvant and a herbicidally effective amount of a compound having the formula: OR 2 R 3 o R, R 1, R 2 and R 3 are as defined in US Pat. claim 1.   12 - Composition according to claim 11, characterized   in the application of the provisions of any one of claims 2-10.   50. 13 - Method for controlling unwanted pants   in plants to be harvested, characterized in that   apply to the location of these undesirable plants.   a herbicidally effective amount of a compound having the formula: C1CH2C R R OR1 R3   o R, R1, R2 and R3 are as defined in the claim 1.   14 - Process according to claim 13, characterized   in so far as the provisions of any one of Claims 2 to 10.   - Method according to claim 13, characterized   in that the plants to be harvested are leguminous plants   his. 16 - Method for controlling or destroying plants   in soybeans, peanuts, rapeseed, cocoyam   brittle beans, alfalfa and vegetables to be harvested, characterized in that it consists in applying instead   o are these unwanted plants a quantity, effectively   from the herbicidal point of view, N-methyl-2'-isopentyloxy-6'-   methyl-2-chloroacetanilide or N-methyl-2'-n-propoxy-6'-   methyl-2-chloroacetanilide or N-methyl-2'-n-butoxy-6'-   methyl-2-chloroacetanilide or N-methyl-2'-isobutoxy-6'- methyl-2-chloroacetanilide.