FR2479202A1 - N-ALCOXYMETHYL-2-HALOACETANILIDE COMPOUNDS AND HERBICIDAL COMPOSITIONS CONTAINING THESE COMPOUNDS AS ACTIVE INGREDIENTS - Google Patents

Abstract

N-ALCOXYMETHYL-2-HALOACETANILIDE COMPOUNDS HAVING THE FORMULA: (CF DRAWING IN BOPI) OR R IS THE GROUP ISOPROPYL, N-BUTYL, ISOBUTYL, SEC-BUTYL, ALLYL OR 2-METHYLBUTYL; R IS METHYL, ISOPROPYL, N-BUTYL OR ALLYL GROUP AND R AND R ARE HYDROGEN OR METHYL GROUP; PROVIDED THAT R, R AND R ARE EACH THE METHYL GROUP WHEN R IS THE N-BUTYL, ISOBUTYL OR SEC-BUTYL GROUP; R AND R ARE EACH HYDROGEN WHEN R IS THE ISOPROPYL, ISOBUTYL OR SEC-BUTYL GROUP AND R IS THE ISOPROPYL OR N-BUTYL GROUP, AND R IS HYDROGEN AND R IS THE METHYL GROUP WHEN R IS GROUP 2 -METHYLBUTYL OR ALLYL AND WHICH R IS THE ALLYL GROUP, ARE ACTIVE INGREDIENTS IN HERBICIDE COMPOSITIONS USED IN VARIOUS HARVESTING PLANTS, PARTICULARLY SORGHUM; HERBICIDES ARE PARTICULARLY EFFECTIVE AGAINST DIFFICULT TO KILL WEEDS SUCH AS YOUNG JOHNSON'S GRASS, BRITTLE CANE, WHITE PROSOMILLET, YELLOW WALNUT CAREX AND RED ROOT ANSERIN.

Description

1. The present invention relates to the field of

  2-haloacetanilides and their use in

  agronomy, for example as herbicides.

  The prior art relating to the present

  the invention includes numerous descriptions of 2-halo

  cetanilides which may be unsubstituted or substituted with a large number of substituents on the anilide nitrogen atom and the anilide ring, including alkyl, alkoxy, alkoxyalkyl, halogen, and the like.

  As an interesting technique for

  embedded image of the present invention, which are characterized by having an alkoxymethyl or alkenyloxymethyl radical on the anilide nitrogen, an alkoxy or alkenyloxy radical in an ortho position and hydrogen or a radical. alkyl

  specificity in the other ortho position, the prior art

  the closest known to the plaintiff is

  US Pat. Nos. 3,442,945 and 3,547,620.

  The most interesting descriptions in patents

  No. 3,442,945 and 3,547,620 are the compounds 2'-

  t-butyl-2-chloro-N-methoxymethyl-6'-methoxyacetanilide and its brominated analog (Examples 18 and 34 of US Pat. No. 3,547,620 and Examples 18 and 36 of US Pat.

3,442,945, respectively.

  U.S. Patents 4,070,389 and 4,152,137.2 disclose a generic formula which includes compounds of the type described in U.S. Patent Nos. 3,442,945 and 3,547,620. However, the only species compound described

  having an alkyl radical in an ortho position and a radical

  alkoxy in the other position ortho has an alkoxy-ethyl radical on the aniline nitrogen atom; compounds of this

  type are shown with more detail below.

  Other prior art documents of less interest are Belgian Patent No. 810,763 and German Published Patent Application No. 2,402. 983, the compounds of these references include compounds of the type described in

  - US Patents Nos. 4,070,389 and 4,152,137 and are

  characterized by having an alkoxyalkyl radical having 2 (or more) carbon atoms between the nitrogen atom

  of anilide and the oxygen atom of the alkoxy part. The dice-

  specific features most interesting in the patent

  No. 810,763 and in the German patent application

  2.402.983 appear to be compounds with a radi-

  ethoxyethyl callus on the anilide nitrogen atom, a radical

  methoxy or ethoxy in an ortho position and a radical radical

  thyl or isopropyl in the other ortho position. By referring

  In Belgian Patent No. 810,763, reference is made to compounds Nos. 7, 16 and 18; other less interesting homologues 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 radical or

  ethoxy in an ortho position and a methyl radical in the

to be ortho position.

  U.S. Patent No. 3,442,945 cited above,

  which describes the compounds mentioned above having a

  chemical representation most closely related to

  of the present invention, contains certain results

  herbicides, and some results are

  for other homologous and analogous compounds that are less closely related in chemical structure. Of

  Similarly, some results are presented for

  Nos. 6 and 9 in Belgian Patent No. 810,763. More by-

  3. In particular, these most interesting references, while describing herbicidal activity on a large number of weeds, do not provide results for

  compounds which are shown to control in addition and / or if

  at the same time, narrow-leaf weeds that are difficult to control and consist of young seedlings

  of Johnson grass and / or the brittle cane both

  the same kind of plant as sorghum, and others

  weeds that are difficult to destroy, such as

  red root and wild prosomillet, in addition to

  less resistant herbs such as fox tail

  yellow, barnyard grass and wild grass, while still

  keeping security for sorghum. Belgian Patent No. 810,763 presents results showing that compound 6 destroyed

  sorghum, while no results are presented for the ef-

  compound 9 on sorghum. As will be shown here, the novel compounds of the present invention have

  unexpectedly superior properties as a herbicide

  in sorghum, vis-à-vis the homo-

prior art logs.

  It is an object of the present invention to

  see herbicides that selectively control

  herbs that are difficult to control or destroy, such as Johnson grass seedlings and / or brittle cane

  And for some species of the present invention,

  weeds that are difficult to destroy, such as

  red root seroma and wild prosomillet, in addition to less resistant weeds such as

  yellow fox, 1 backyard grass and wild grass,

  particularly in sorghum, in a manner superior to that

the prior art.

  The objects listed above and other objects of

  the present invention will become more apparent from the description of

detailed below.

  The present invention relates to compounds having herbicidal activity, to herbicidal compositions containing

  these compounds as active ingredients and the herbal process.

  4. Bicide use of these compounds in plants with

  harvest particular, especially sorghum. -

  The Applicant has now found that a group

  selective 2-haloacetanilides, characterized by radi-

  specific alkoxymethyl or alkenyloxymethyl cals on the anilide nitrogen atom, specific alkoxy radicals

  in an ortho position and hydrogen or the radical metal

  thyl in the other ortho position, has remarkable selective herbicidal properties and superior

  Unexpectedly as herbicides for sorghum, with regard to

  bicides of the prior art, comprising compounds

  homologues of the most interesting prior art.

  A main feature of herbal compositions

  bicides of the present invention is their ability to control

  selectively narrow-leaf weeds consisting of young Johnson grass plants and / or brittle cane that are species of the same plant species as sorghum; in fact, sorghum and brittle cane are both of the bicolor sorghum species. As a result, it is extremely difficult to selectively control the cane

  brittle and young Johnson grass plants in the

  gho, without damaging the sorghum at the same time. In addition,

  some of the compounds of the present invention,

  also kill or destroy other hard-to-destroy species, such as red-rooted hawthorn, sedge

  yellow walnut trees or the white prosomillet, and all the

  of the present invention control or destroy from

  species such as yellow fox tail, barnyard grass, wild grass and other weeds

harmful.

  The compounds of the present invention are characterized

  by the formula: I CiCH2C CH20R

2

R3 OR

3 R1

R2 5.

  o R is isopropyl, n-butyl, isobutyl, sec-butyl-

  allyl or 2-methylbutyl; R 1 is methyl, isopropyl, n-butyl or allyl and R 2 and R 3 are hydrogen or methyl, provided that R 1, R 2 and R 3 are each methyl when R is n-butyl, isobutyl or sec-butyl; R2 and R3 are each hydrogen when R is isopropyl, isobutyl or sec-butyl and R1 is isopropyl or n-butyl, and R2 is hydrogen and R3 is methyl when R is

  is the 2-methylbutyl or allyl group and that R1 is the group

pe allyle.

  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-

chloroacetanilide,

  N- (sec-butoxymethyl) -2'-methoxy-3 ', 6'-diimethyl-

2-chloroacetanilide,

  N- (allyloxymethyl) -2'-allyloxy-6'-methyl-2-

chloroacetanilide,

  N- (2-methylbutoxymethyl) -2'-allyloxy-6'-methyl-

2-chloroacetanilide,

  N- (isopropoxymethyl) -2'-isopropoxy-2-chloroacetate

nilide,

  N- (isobutoxymethyl) -2'-isopropoxy-2-chloroacetate

nilide and

  N- (sec-butoxymethyl) -2'-n-butoxy-2-chloroacetate

  nilide. The utility of the compounds of the present invention as active ingredients in 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.

  manufactured in many ways. For example, these compounds may

  can be prepared by the azomethine process described in

  U.S. Patent Nos. 3,442,945 and 3,547,620

  born above. According to the azomethine method, the aniline

  mayor is reacted with formaldehyde to obtain the corresponding methyleneanine (phenylazomethine

  substituted), which is then reacted with a halogenated

  acetylation such as chloroacetyl chloride or anhydridin

  of chloroacetic acid, which, on the other hand, is reacted with the appropriate alcohol to give the corresponding N-alkoxymethyl- or N-alkenyloxymethyl-2-chloroacetanilide as the

that final product.

  Another method for producing compounds according to the present invention involves N-alkylation of the anion of the

  2-haloacetanilide secondary suitable 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 alkylation process described in Example 1 herein involves the in situ preparation of halomethyl and alkyl ethers 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 process of this example, the alkylating agent. is formed in situ, performing

  thus an efficient, economical and simple operation.

  In a cooled mixture of 9.25 g (0.125 mole) of isobutanol, 1.86 g (0.062 mole) of anhydrous paraformaldehyde and 100 ml of methylene chloride was added 7.56 g (0.062 g). mole) of acetyl bromide; the mixture was stirred until all of the paraformaldehyde was dissolved, i.e., about 45 minutes. In the mix, we then have

  added 4.55 g (0.02 mol) of 2'-methoxy-3 ', 6'-dimethyl-2-

  chloroacetanilide and 2.0 g of benzyltriethylammonium chloride

  in 100 ml of methylene chloride. The mixture has been

- 7.

  cooled to 15 C, 50 ml of 50% NaOH was added

  in one go and shake for 5 minutes. In the mix

  After stirring, 150 ml of cold water were added. The layers were se-

  prepared, washed with water, dried over MgSO 4 and evaporated by the so-called Kugelrohr device to obtain 5.0 g (79% yield) of a yellow liquid having a boiling point of 107 ° C.

at 0.02 mm Hg.

  Analysis calculated for C16H24ClNO; (%): C, 61.24; H, 7.71;

C1,11,30

Found: C, 61.24; H, 7.72;

C1,11,28

  The product has been identified as N- (isobutoxymethyl) -

  2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanilide.

EXAMPLES 2-8

  Following substantially the same procedure and conditions as described in Example 1, but substituting the appropriate secondary anilide and the appropriate alkylating agent as starting materials and appropriate 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

IFormule! P.E. El- Analysis Exem-

Empirical Cops iC ntCal- Trouble

  Compound (## STR4 ## N- (isopropoxymethyl) C15H22ClN03 (C) 60.10 60.38 thyl) -2'-isopropyl (0.01H 7.40 6.80 xyl-2-chloroacetate) - Cl 1, 83 11.94 nilide 3 N- (isobutoxymethyl) -HClNO 113 C 61.24 61.23 2'isopropoxy-2-4 3 (0.03) H 7.71 7.72 chloroacetanilide Cl 1i, 30 11.30 4 N (allyloxymethyl) -16 CN3 116 C 62.03 61.98 2'-allyloxy-6'-m- (0.03 H 6.51 6.53 thyl-2-chloroacet Cl 11, 11.44 tanilide 5 N- (sec-hutoxymethyl) 17H26CtNO3 115 C 62.28 2.18 thyl) -2'- (0.02 H 7.99 8.03 n-butyl-2-chloro: Cl 10.81 0 80 acetanilide 8. TABLE I (Contd.) 6 N- (n-butoxymethyl) C16H25ClNO3 108 C 61.24 61.15 2'-methoxy-3 ', 6'-di-(0.1) H 7, 71 7, 79 methyl-2-chloroacetin Cl 11.30 11.30 tanilide 7 N- (sec-butoxymethyl) -CH C1N1624O 116 C 61.24 61.13 2'-methoxy-3 ', 6'-di- C16 24, 37.78

(0.07) H 7.71 7.78

  2-methyl-chloroacetamide C 11.30 11.24 tanilide 8 N- (2-methylbutoxyC18H26ClNO3 118 C 63.61 63.61 methyl) -2'-allyl-6'- (0.08) H 7.71 7 , 79 methyl-2-chloroacet- C10, 43, 10.44 tanilide .C Starting materials consisting of anilides

  used in the preparation of the examples below.

  above are prepared according to known methods, for example

  by haloacetylation of the corresponding primary amine

  with haloacetylating agents such as halogenide halide

  acetyl 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 agitated.

  while mixing with a halogen solution

  haloacetyl, for example chloroacetyl chloride,

  the, 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 under vacuum.

  The primary amines used to prepare secondary anilides may also be prepared by known means, for example by catalytic reduction of the appropriately substituted corresponding nitrobenzene, for example 2-alkoxy-6-alkylnitrobenzene, in a solvent.

  such as an alcohol, for example ethanol, using a

  platinum oxide catalyst; for 2-alkenyloxy (e.g., allyloxy) -6'-alXyl compounds, a chemical reduction

  using iron and acetic acid can be used.

  See. As noted above, the compounds of this

  inv-ention have proven effective as herbicides, particularly

  primarily as pre-emergence herbicides, although the

  9. Post-emergence life was also-presented. Tables II and III summarize the results of tests conducted to determine the pre-emergence herbicidal activity of

  compounds of the present invention.

  The pre-emergence test was conducted as follows A good quality of top soil is placed in

  aluminum boxes and compacted to a

  Foundry 9.5 mm to 12.7 mm from the top of the boot.

  Above the ground, a predetermined number of seeds are placed

  or vegetative propagules of various species of plants.

  The soil required to fill the boxes after seeding

  addition of vegetative propagules is weighed in

  a boot. Soil and a known amount of the active ingredient

  It is applied in a solvent or in the form of a wettable powder suspension and is fully mixed and used to cover the prepared cans. After treatment, the boots

  are sent to a greenhouse bench where they are provided with an

  initial fill of water from above, equivalent to 0.64 cm

  of waterfall, then humidified by irrigation with

  under, as is necessary to give adequate moisture

  te for germination and growth.

  Approximately 2 weeks after seeding

  and treatment, the plants were observed and the results

  registered states. Tables II and III below summarize these results. Herbicide evaluation was obtained using a fixed scale based on the percentage of damage to each plant species. Evaluations are defined as follows:% Control Rating

0-24 0

-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:

* 24? 9202

  A Canada Thistle B Nielle des champs C Velvet Leaf D Garden Volubilis E Lamb Quarter I'Young Plants F Beautiful Johnson G Grass Weed Yellow Y Grass Brome Fluffy

walnut K Grass bass-

H Hedgehog herb latan

TABLE II

  Pre-emergence activity The compounds were further tested using the

  procedure above on the following plant species

  : L Soy R Hemp Sesbania M Sugar Beet E Quarter Lamb N Wheat F Beautiful Grass 0 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.

  Composed of Plant species Example n kg / ha A B C D E F G- H I J K

1 11.2 3 3 0 3 3 3 3 3 0 3: 3

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

2 11.2 O 1 1 3 1 1 0 3 O 3 3

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

3 11,2 3 0 1 10 2 3 2 0 3 3

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

4 11.2 3 1 2 2 2 2 3 0 O 3 3

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

11.2 - - - 2 2 3 2 1 3 3

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

6 11,2 3 2 1 2 3 3 3 3 3 3 3

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

7 11,2 3 2 1 2 3 3 3 3 3 3 3

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

8 11.2 3 Q 0 0 2 3 1 2 1 3 3

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

11.

TABLE III

  Pre-emergence Activity Compound of Plant Species Compound of Example n kg / haL M N O P B Q D R E F C J S K T kL __

3 2232 2 3 2-3 32 0 3 3 3 3

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

0 1 0 1 0 1 1 0 0 0 0 0 0 1.33

01000000-0000013

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

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

0000 1 0 1 1 1 2 0 0 2 3 3 3

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

00 2 3 1 0 0 1 1-1002333

* 002 2000000001333

0001001000001133

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

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

12 0 3 1 0 0 0 1 1 1 0 3 3 3 3

O OO O O 0 000 1 0 0 0 0 0 1 3

0 2 2 2 1 0 1 1 3 2 2 0 3 3 3-

0 1 0 2 0 0 0 0 1 0 1 0 3 3 3-

0 1 0 10 0 0 0 11 1 0 3 1 3-

0 00 0 0 0 0 1 0 0 0 0 0 2-

2 2 2 3 3 2 2 2 3 2 2 1 3 3 3-

1 2 2 3 2 1 2 2 3 2 2 0 3 3 3-

0 1 1 1 00 1 1 1 1 1 0 2 3 3-

O 1 1 1 0 0 1 I 2 0 0 0 1 2 3-

110000011000023-

22332132 3 3 3 1 3 3 3-

1 2 1 3 1 0 1 1 2 2 2 0 3 3 3-

0 2 1 3 0 0 1 0 2 1 1 0233-

0 1 2 2 1 0 1 1 1 0 1 0 333-

011100000030333-

O 00000 0001030 03 -

000000000030000-

0 0 0000000000000-

  The herbicides of the invention have been found to possess superior properties

presents

  unexpectedly as selective pre-emergence herbicides for use in sorghum, especially for

  selective control of weeds that are difficult to destroy

  re, including one or more of the constitutive weeds

  , 6 1.12 0.28 0.06 0.01, 6 1.12 0.28 0.06, 6 1.12 0.28 0.06, 6 1.12 0.28 0.06 0.01 , 6 1.12 0.28 0.06, 6 1.12 0-, 28 0.06 0.01, 6 1.12 0.28, 6 1.12 0, 28 0.06 0.01, 12.

  killed by young Johnson grass plants, the cane cas-

  red root, yellow walnut sedge and white prosomillet, in addition to other problematic weeds such as yellow fox tail, barnyard grass and large wild grass. Selective control and suppression of some of the weeds mentioned above and still others with the herbicides of the present invention have been found in a large number of other crops to be harvested including soybeans, wheat, rice and sugar beet, as shown in Table III above. However, the distinctly remarkable herbicidal properties of the compounds of the present invention are the

  more obvious in their selective control of bad her-

in sorghum.

  To illustrate the superior properties of

  unexpectedly of the compounds of the present invention at the same time

  on an absolute basis and on a relative basis,

  paratives were conducted in the greenhouse with: (1)

  homologues of the prior art most chemically structurally related to the compounds of the present invention and (2) two other compounds which, although not homologues, fall within the scope of the present invention.

  prior art and one of them has sufficient properties

  as sorghum herbicide and both are commercially available herbicides. All compounds in

  Comparative tests below are generically defined as

  being substituted phenyl-N-hydrocarbyloxyalkyl-2-haloacetate

  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-chloro

  acetanilide (Example 18, U.S. Patent Nos. 3,442,945 and 3,547,620)

  B. N- (methoxymethyl) -2'-methoxy-6'-t-butyl-2-bromo

  acetanilide (Example 34 of US Patent No. 3,547,620 and Example 36 of US Patent No. 3,442,945)

  C. N- (methoxymethyl) -2'-methoxy-6'-methyl-2-chloro

13.

  acetanilide (compound No. 6 of Belgian Patent No. 810,763;

  German Published Patent Application No. 2,402,983)

  D. N- (ethoxyethyl) -2'-methoxy-6'-methyl-2-chloroacetate

  cetanilide (Compound No. 7 in Belgian Patent No. 810,763) E. N- (1-methoxyprop-2-yl) -2'-methoxy-6'-methyl-2-chloroacetanilide (Compound No. 9 of Belgian Patent No. 810,763)

  F. N- (methoxyethyl) -2'-ethoxy-6'-methyl-2-chloro

  acetanilide (compound No. 16 of Belgian Patent No. 810,763)

  G. N- (ethoxyethyl) -2'-ethoxy-6'-methyl-2-chloroacetate

  tanilide (compound No. 18 of Belgian Patent No. 810,763) H. N-Isopropyl-2chloroacetanilide (common name propachlor)

  I. N- (methoxymethyl) -2 ', 6'-diethyl-2-chloroacetanilide (ex.

  US Pat. No. 3,442,945 and US Patent No. 3,547,620); ncc current "alachlor", active ingredient of the commercial herbicide known as Lasso, which is a registered trademark of so-called

Monsanto Company.

  J. N- (Isopropoxyethyl) -2'-methoxy-6'-methyl-2-chloro

roacétanilide.

  Although compound H above has a structural

  less similar to that of the counterpart herbicides

  United States Patent Nos. 3,442,945 and

  3,547,620, since it lacks an alkoxy-substituted substituent

  alkyl or alkenyloxyalkyl on the nitrogen atom and a substitute

  killing alkoxy in an ortho position, it is included in the tests herein because it is referred to in US Pat. Nos. 4,070,389 and 4,152,137 and has shown superior properties as a commercial herbicide. for sorghum, relative to other compounds in these patents. Similarly, Compound I is included in the tests herein because it is within the scope of US Patent Nos. 3,442,945 and 3,547. 620 and that he got a

  status as a commercial herbicide.

  In pre-emergence herbicide tests,

  of the present invention have been compared to prior art compounds A-I with respect to control or destruction of various weeds, emphasizing that narrow-leaved, hard-to-destroy species that

  are predominant infestations in sorghum. The re-

  Experimental results are presented below.

  In the discussion of the results below, reference is made to the herbicide application rates symbolized by "GR" and "GR 5", these rates being given in kilograms per kilogram.

&

  hectare (kg / ha). GR 5 defines the maximum rate of herbicide required to produce 15% (or less) of damage to the plants to be harvested, and GR85 defines the minimum rate required to obtain 85% inhibition of weeds.

  GR15 and GR85 are used as measures of

  potential commercial merit, obviously being of course

  suitable commercial herbicides can

  damage to plants more or less

within reasonable limits.

  - Another guide to the effectiveness of a Chinese product

  as a selective herbicide is the "selection factor

  "(" SF ") for a herbicide in given crop plants and in specific weeds.The selectivity factor is a measure of the relative degree of safety for

  plants to be harvested and damaged

  bes is expressed in terms of the GR15 / GR85 report, ie

  say GR15 for the crop to be divided by the GR85 for the weed, both being in kg / ha. In the tables below, when used, we represent the selectivity factors in parentheses

  after the weed; the symbol "NS" indicates "non-selective

  marginal or doubtful selectivity is indicated

  by a dash (-) after the plant to harvest.

  Since the tolerance to 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,

  it is desirable that the safety factors for the plan-

  to harvest, that is to say the tolerance values for her-

  bicides, are high, since higher concentrations

  Herbicides are frequently desired for one reason or another. Reciprocally it is desirable that weed control rates be low, ie that the herbicide has a high unit activity, for economic and possibly ecological reasons.

  cal. However, low application rates of a herbicide 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 greatest number of weeds with the least amount of herbicide and provide the greatest degree of weed control.

  for the plants to be harvested, that is to say the

  for the plants to be harvested. As a result, we use

  reads the "selectivity factors" (defined above) to quantify the relationship between plant safety

  harvesting and the control or destruction of the bad her-

  bes. 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.

  The pre-emergence tests referred to here include both greenhouse and

  field tests. In tests in greenhouses, the her-

  bicide is applied as a surface application after planting seeds and vegetative propagules or by incorporation into a certain amount of soil, to be applied

  as a covering layer on the experimental seeds

  in experimental containers pre-seeded.

  In field tests, the herbicide is incorporated into the soil before the plant ("P.P.I."), ie

  the herbicide is applied to the soil surface and then incorporated

  in it by means of mixing, followed by

plant seeds to harvest.

  The experimental surface application method used in the greenhouse is carried out as follows: containers for example aluminum cans typically 24.13 cm × 13.34 cm × 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 to the level with loam soil

  said Ray, then compacted to a level of 1.27

  cm from the top of the pots. The pots are then ersemen-

  with a species of plant to experiment with, and then

  green with a layer of 1.27 cm from the experimental soil. L! Her-

  bicide is then applied to the soil surface with a

  belt sprayer, at the rate of 187 1 / ha

  a pressure of 2.11 kg / cm; other means of spraying

  For example, a DeVilbiss sputtering device is also used occasionally. Each pot receives 0.64 cm of water as irrigation from above and pots

  are then placed in greenhouses for an irriga-

  later, as necessary.

  As an alternative procedure, top irrigation may be omitted. Observations of herbicidal effects are made approximately three weeks after treatment. The soil incorporation herbicide treatment used in greenhouse testing is as follows: Good top soil quality is placed in the soil.

  aluminum boxes and compacted to a

  Foundry 9.5 mm to 12.7 mm from the top of the box.

  Above ground, a number of seeds or vegetative propagules of various plant species are placed. The

  soil required to fill the boxes at the seed level after

  The addition or addition of vegetative propagules is weighed in a box. The sol and a known amount of the active ingredient, applied in a solvent or as a wettable powder suspension, are fully mixed and used to coat the prepared dishes. After treatment, we provide

  the boxes an initial irrigation of water from above, equi-

  worth 0.64 cm of rainfall, then humidify with

  from below, as is necessary to give

  adequate moisture for germination and growth.

  As an alternative procedure, top irrigation can be omitted. The observations are made 17.

  about three weeks after seeding and treatment.

  In the tables below, we made the average

  do results for compounds that 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-emergence herbicidal activity are presented in Table IV, comparing the relative effectiveness of the compounds of Examples 1 and 5, which are representative compounds of the present invention, with compounds of interest. of the prior art, that is to say the compounds A, B, D, F and

  G, as selective herbicides against bad herbs

  particular needs commonly associated with sorghum. The bad

  herbs used in the tests here have the following abbreviations in the tables: red-rooted parsley (RPW), Johnson grass seedlings (SJG), brittle cane (SC), white prosomillet (WPM), courtyard (BYG), large

  wild grass (LCG) and yellow fox tail (YFT).

TABLE IV

  GR5 rate GR85 rate (kg / ha) _ __ (kg / ha) Compo-Sorghum RPW SJG SCG SC BYG YNS

  A 0.28 2.24 (NS) <0.14C> 2.0) <0.14 (> 2.0) 0.56 (NS) <0.14 (> 2.0) 1.57 (NS) )

  B <0.14 0.28 (NS). <0.14 (-) <0.14 (-) 0.28 (NS) <0.14 (-) 1.12 (NS)

  D <0.14 0.28 (NS), <0.14 (-) <0.14 (-) <O, 14 (NS) <0.14 (-) <O, 14 (NS)

  G <0.14 0.28 (NS) <0.14 (-) <0.14 (-) O, 28 (NS) <0.14 (-) <O, 14 (-)

  F <0.14 0.34 (NS) <0.14 (-) <0.14 (-) 0.14 (NS) <0.14 (-) 0.34 (NS)

  Ex. 1 1.12 2.24 (NS) 0.14 (8.0) <0.14 (> 8.0) 2.07 (NS) <0.14 (> 8.0) 2.07 ( NS) Ex. 5> 2.24> 2.24 (-) 0.14 (> 16.0) <0.14 (> 16.0) 2.24 (> 1.0) 0.14 (> 16 , 0) 1, 46 (> 1.5) Compound WPM YFT

At 1.12 (NS) <0.14 (> 2.0)

B 0.56 (NS) <0.14 (-)

C <0.14 (NS) <0.14 (-)

F 0.56 (NS) <0.14 (-

G 0.56 (NS) <0.14 (-)

  Ex. 1 1.68 (NS) <0.14 (> 8.0) Ex. 5> 2.24 (-) 0.56 (> 4.0) OO H0 rO -'J rla Fr 19. In Referring to the results in Table IV, it will be seen that, relative to the safety of the plants to be harvested (as indicated by the GR15 rate for sorghum),

  the compounds of the present invention showed a superior

  remarkable difference in relation to the compounds of the

  than earlier. In particular, compared to com-

  poses of the prior art most intimately

  from a structural point of view, that is to say the compounds

  A and B having the configuration of N-alkoxymethyl-2'-alkoxy-6'-

  alkyl-2-haloacetanilide, the compounds of the present invention

  in the test were at least 8.0 to more than 16.0 times as much on sorghum as

  4.0 to more than 8.0 times safer than compound A.

  Similarly, the compounds of the present invention were 8.0 to more than 16 fold greater on sorghum than homologous compounds of the prior art 1D, F and G,

  each of which caused more than 15% damage to the

  gho at a very low rate of less than 0.14 kg / ha.

  With regard to the control or destruction of weeds, indicated by the GR85 application rates under each weed, it should be noted that all the compounds of the prior art in the test, except for compound A, were completely non-selective or selective

  marginally or questionably against all the bad

  herbs in the test in sorghum. Compared with Compound A, the compounds of the present invention were about 4.0- to 8.0-fold more effective against seedlings.

  of Johnson grass, the large wild grass and grass of

  outcross, and 2.0 to 4.0 times more effective against the yellow fox tail. The compound of Example 5 also exhibited

  positive selective control of the cane brittle and

  walnut rex and marginal selectivity compared to red-rooted and white prosomillet

compound A did not provide.

  In another comparative test, the compound of the

  ple 1 has been compared for its herbicidal efficacy of

  emergence compared to that of compounds C, D and J, the

  20. The results from this test are shown in Table V.

TABLE V

  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 sorghO substantially higher than that of the compounds of the prior art,

  that is, it was at least 8.0 times snr. In-

  in addition to having a higher safety factor

  for the plants to be harvested, the compound of the present invention

  The invention showed selectivity factors uniformly and remarkably higher than those of the prior art compounds against each of the weeds in the test. It will be noted that compounds C, D and J of

  prior art could not provide a selective

  positive for plants to be harvested against Johnson grass seedlings and the selectivity of these compounds

  against the remaining weeds was questionable or

  at best; in any case, the weak security factors

  of these compounds render them unsuitable as hereditary

bibcids for sorghum.

  Herbicide results from pre-emergence

  from other tests for the compounds of the

  Examples 1-8 are shown in Table VI.

  In Table VI, the GR15 and GR85 rates are shown

  for each compound of the invention in sorghum and mumps.

  interesting herbs, respectively; the selectivity factor values are presented in parentheses.The results from multiple tests are presented as ITaux GR J Rate GR Compo- (kq / ha) (kg / ha) 85 se rgho SJG BYG LCG YFT

  D <0.14 0.14 (NS) <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 (-)

  Ex. 1 1.12 0.84 (1.3) <0.14 (> 8.0) <0.14 (> 8.0) <0.14 (> 8.0) 21. the average of the number indicated A space left blank under a particular weed indicates that this weed was not present in the test given for

the interesting compound.

TABLE VI

  He has a. The results represent the averages of seven double b trials. The resuitats represent the average of five tests performed in double c .. The results? represent the average of two trials performed in duplicate d. The results represent the average of three trials performed in double r%) Do "o (D M) Rate GR1 Rate GR85 Compound (kg / ha) RPW SJG LCG (kg / ha) _ Compound Sorghum RPW SJG LCG SC BYG YNS

E. ia 1 ,.

  Ex. 1.14> 0.41 (> 2.8) 0.43 (2.7) <0.09 (> 12.7) 0.97 (1.18) 0.095 (12.0) 1, 0 (1,14)] Ex. 2> 1.12 0.56 (> 2.0) <0.14 (> 8.0), 0.22 (5.0) Ex. 3> 1.12 0.56 (> 2.0) 0 , 28 (> 4.0) 0.28 (> 4.0) Ex. 4 0.57 0.43 (1.3) <0.16 (> 3.6) 0.09 (> 6.4) <0, 15 (> 3.8) <0.09 (> 6.4) 0.35 (1.6) Ex. 5c> 2.24> 2.24 (- 1 0.28 (> 8.0 ) <0, .12 (> 18.7) 1.3 (> 1.7) 0.16 (> 14.0)> 1.9 (-1.2) Ex. 6c 0.7 0.14 ( 5.0) 0.14 (5.0) <0.14 (> 5.0) 0.14 (> 5.0) <0.11 (> 6.4) 0.43 (1.6) Ex 7> 0.7 0,, 35 (> 2.0) <0.09 (> 7, 8)> 0.11 (V6.4) <0.07 (> 10.0) <0.09 ( > 7.8) 0.84 (NS) Ex. 8> 1.12 o, 21 (> 5.3) 0.28 (> 4.0) 0.28 (> 4.0) Compound WPM YFT Ex 1a 0.75 (1.52) 0.12 (9.5) Ex. 2 0.16,> 7, O) Ex. 3 O, 46 (> 2.4) Ex. 4b 0.64 (NS) ) 0.09 (6.4N Ex. 5c> 1.4 (, 1.6) 0, 3G (> 6.2) Ex. 6c 0.21 (3.3) <0.11 (> 6.4 ) Ex. 7d 0.21 (> 3.3) <0.09 (> 7.8) Ex.8 0.28 (> 4.0) 23. Referring to the results in Table VI, it should be noted that first, that each compound of the present invention, tested both against 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 unequaled by any known compound of the prior art

  according to the knowledge of the applicant, including the

  commercial bicides consisting of compounds H and 1, noting that compound H is a dominant commercial herbicide

  for sorghum. Moreover, if it were not three exceptions, each

  that compound of the present invention exhibited a positive selective control of each weed tested; the

  exceptions were the lack of positive selectivity of the

  1e5 s of Example 4 against white prosomillet and compound

  of Example 7 against walleye sedge and selection

  marginal activity of the compound of Example 5 against anserin

red root.

  Since the pre-emergence herbicidal results presented in Tables IV-VI were obtained according to identical routine procedures, a comparison. The herbicidal efficacy of the compounds of the present invention in Table VI can also be achieved with respect to the herbicidal efficacy for the compounds of the art.

  previous in tables IV and V. Here, again, one. of-

  clearly shows that each of the compounds of this invention

  The above is of interest to all prior art compounds of most interest depending on the safety of the plants to be harvested, without exception, and the selective global control of weeds as evidenced by the selectivity factors. , again

  with exceptions in isolated cases. More specifically

  among all the tested compounds of the prior art

  Only compound A (Table IV) exhibited

  selective selection of young Johnson grass plants,

  be wild, of barnyard grass and of yellow fox tail in sorghum; Compound A was not selective against the remaining weeds in the test. Against the

  weeds that compound A really controlled selectively

  However, the compounds of the present invention

  remarkably superior selectivity, with the exception of the compounds of Examples 2 and 3 which behaved

  compared to compound A against young seedlings

  be from Johnson. In any case, the low safety factors for sorghum and / or non-selectivity or

  doubtful selectivity of the compounds of interest

  than earlier against all the weeds in the

  - tests above render these compounds completely unsuitable

  as herbicides for sorghum.

  As mentioned previously, the compounds H and I are

  designated in prior art patents

  above and are active ingredients in commercial herbicides; compound H is widely used as a herbicide for sorghum. Although neither of these compounds are homologues, isomers or analogues of the compounds of the present invention, these compounds have been tested in an identical manner and against the same weeds as those employed. in the

  tests for the compounds of the present invention, such as

  shown in Tables IV-VI, in order to determine their

  Pre-emergence herbicide against the compounds of the present invention. (Based on averages of five duplicate tests of compound I and nine tests performed in duplicate with compound H), it was determined that neither neither compound selectively controlled the

  brittle cane in sorghum and that compound H does not present

  was no positive control of young grass plants

  Johnson, whereas Compound I showed only one selection

  marginal tivity, having a selectivity factor of order

* about 1.2 against Johnson grass seedlings. Au-

  In fact, compounds H and I really have selective control of the remaining weeds, as presented in

  the tables IV-V: As a result, it appears that

  of the present invention provide advantages

  25. Compared with commercial herbicides for

  selective control of weeds in sorghum.

  The compounds of the present invention have an activity

  selective herbicide in a large number of

  other than sorghum, as shown in Table III above. In still other tests, it has also been shown that the compound of Example 5 was useful at levels higher than 1.12 kg / ha in soybeans, maize fields, cotton, cucumber, brittle beans. , garden peas,

tomatoes and peanuts.

  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 both absolutely

  and relative to the most

  interesting from a structural point of view; compared to other homologues and other related analogs, including

  2-haloacetanilides of the trade of the prior art.

  More particularly, the compounds of the present invention

  showed a remarkable safety for the plants to be harvested

  in sorghum and factors of particular selectivity

  remarkable for the species of bad

  besides difficult to destroy, such as young Johnson grass plants and brittle cane, and other herbs posing

  problems such as red root lanserine, sedge

  walnut trees, the white prosoinillet, the yellow fox tail, the barnyard grass, the wild grass, etc. as presented

in Tables II-VI.

  The herbicidal compositions of the present invention comprising concentrates that require dilution prior to application, contain 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

  sufficient surfactants to make a given composition readily dispersible in

  water or in oil. The incorporation of a surfactant

  - tif in the compositions greatly enhances their effectiveness.

  you. By the term "surfactant", it is understood that wetting agents, dispersing agents, agents

  suspending agents and emulsifying agents are included.

  Anionic, cationic and nonionic agents may

  to be used with equal ease.

  Preferred wetting agents are alkylbenzenes

  zen and alkylnaphthalenesulfonates, sulfa fatty alcohols

  acids, amines or amides, acid esters

  long-lived catches of sodium isethionate, sulphate esters

  sodium succinate, sulfated or sulphated fatty acid esters,

  oils, sulphonates of petroleum, sulphate vegetable oils

  derivatives, acetylenic glycols, ditertiary

  polyoxyethylenes of alkylphenols (particularly

  octylphenol and nonylphenol) and polyoxyethylenated derivatives

  monocarboxylic fatty acid esters of hexitol anhydrides (eg sorbitan). Some products

  The preferred dispersing agents are methylcellulose, alcohol

  lyvinyl, sodium lignin sulphonates, alkylnaphthyl

  polymeric talenesulfonates, sodium naphthalenesulfonate and polymethylene bisnaphthalenesulphonate.

  Wettable powders are dispersive compositions

  sands in water containing one or more ingredients

  an inert solid extender (filler) and one or more wetting or dispersing agents. Solid inert extension products are usually of mineral origin, such as natural clays,

  diatoms and synthetic minerals from

  this and the like. Examples of this extension products

  (loads) include kaolinites, so-called attapula-

  cottage and synthetic magnesium silicate. Compositions

  The wettable powder compositions of the present invention contain

  ordinarily about 0.5 to 60 parts (preferably 5-

  parts) of active ingredient, about 0.25 to 25 parts (preferably 115 parts) of wetting agent, about 0.25 to 25 parts (preferably 1.0-15 parts) of

  dispersion and 5 to about 95 parts (preferably 5-50 parts

  inert solid extension product, all parts being by weight based on the total composition. When

  this is required, approximately 0.1 to 2.0 parts of the product of exten-

  inert solid can be replaced by an inhibitor of

  corrosion or an anti-foam agent or both.

  Other formulations include concentrates of

  dust containing 0.1 to 60% by weight of an active ingredient

  tif on a suitable extension product; these dusts can

  may be diluted for application at concentrations in

  the range of about 0.1-10% by weight.

  The aqueous suspensions or emulsions may 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 an emulsion. stable particles very finely divided. The resulting concentrated aqueous suspension is

  characterized by its extremely small particle size

  ble, so that when it is diluted and

  covering is very uniform. Suitable concentrations

  of 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 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 a

  emulsifier consisting of lignin sulphonate and a chemical product

  water-immiscible agent, and polyphenylisocyanate of

  lymethylene, by dispersing the immiscible phase with water, in

  the aqueous phase, followed by addition of a polyfunctional amine

  nelle. The isocyanate and amine compounds react to

  to form a solid urea shell wall around

  water-immiscible chemical, thus forming microcapsules. Generally, the concentration of

  microencapsulated material will range from about 480 to 700 g / l of

  total, preferably 480 to 600 g / l.

  Concentrates are usually solutions for

  active ingredient in solvents immiscible with water or

  usually immiscible with water with a surfactant.

  Suitable solvents for the active ingredient of the present invention

  The present invention includes dimethylformamide, dimethylformamide,

  sulfoxide, N-methylpyrrolidone, hydrocarbons and

  ethers, esters or ketones immiscible with water. This-

  during, other high concentration liquid concentrates can be formulated by dissolving the active ingredient in a solvent, and then diluting, for example with Rerosene,

  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 oil

emulsifying.

  The granules are physically stable particulate compositions comprising the active ingredient adhering to or dispensed through a base matrix of an inert, finely divided particulate extension product. To help

  the leaching of the active ingredient from the product

  a surfactant, such as those mentioned above.

  duly, may be present in the composition. Natural clays, pyrophyllites, illite and vermiculite are

  examples of well-functioning classes of exten-

  particulate mineral (charges). The products of exten-

  preferred are the porous absorbent preformed particles

  such as pre-formed and sieved particulate attapulgite or thermally expanded particulate vermiculite and finely divided clays such as so-called clays.

  kaolin, hydrated attapulgite or bentonitic clays.

  These extension products are sprayed or blended 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

  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

particle size.

  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.

  above. Useful chemicals in combination with the active ingredients of the present invention include, for example,

  triazines, ureas, carbamates, acetamines,

  acetanilides, uracils, acetic acid derivatives,

  or phenol, thiolcarbamates, triazoles, benzoic acids, nitriles, biphenyl ethers or the like, such as: Heterocyclic nitrogen / sulfur derivatives 2-chloro-4-ethylamino-6isopropylamino-s-triazine 2- chloro-4,6-bis (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) -pyra-

  zidinium 30. 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- (3,4-dichlorophenyl) -1,1-dimethylurea 1,3-dimethyl-3- (2-benzothiazolyl) urea 3- (pchlorophenyl) -1 1-Butyl-3- (3,4-dichlorophenyl) -1-methylurea Carbamates / thiolcarbamates 2-chloroallyl diethyldithiocarbamate N- (4-chlorobenzyl) N- (3chlorophenyl) carbamate N, N-diethylthiolcarbamate isopropyl

  S-2,3-dichloro N, N-diisopropylthiolcarbamate

  allyl ethyl N, N-dipropylthiolcarbamate S-propyl dipropylthiolcarbamate Acetamides / acetanilides / anilines / amides 2-chloro-N, Ndiallylacetamide 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

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

  N-(1,1-dimethylpropynyl) -3,5-dichlorobenzamide Acids / esters / alcohols 2,2-dichloropropionic acid 2-methyl-4chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid Methyl 4- (2,4-dichlorophenoxy) phenoxy] propionate 3-amino-2,5-dichlorobenzoic acid 2-methoxy-3,6-dichlorobenzoic acid 31. 2,3,6-trichlorophenylacetic acid N1-acid -naphtylphtalamique

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

  sodium benzoate 4,6-dinitro-o-sec-butylphenol

  N- (phosphonomethyl) glycine, its mono-

  C1-6alkylamines, its alkali metal salts and combinations thereof Ethers 2,4-Dichlorophenyl and 4-nitrophenyl ether

  2-chloro-α, α, α-trifluoro-p-tolyl-3-ethoxy-4-nitro-

  diphenyl Various dioxins 2,6-dichlorobenzonitrile monosodium acid methanearsonate disodium methanearsonate

  Useful fertilizers in combination with the

  Active ingredients include, for example, ammonium nitrate,

  urea, potassium carbonate and superphosphate. On au

  useful additive products include materials in the

  which plant organisms take root and grow

  such as compost, manure, humus, sand and the like.

  Herbicidal formulations of the types described above

  above are given as examples in several examples.

  illustrative examples below.

  I. Emulsifiable Concentrates T% in Ponds A. Compound of Example No. 150, 0 Mixture of Dodecylbenzenesulfonate

  Calcium / polyoxyethylene ethers (eg

  product known as Atlox 3437F and Atlox 3438F) - 5, 0 Monochlorobenzene 45.0

100.00

  B. Compound of Example No. 85.0 Calcium Dodecyl Sulfonate / 32. Alkylaryl Polyether Alcohol Solvent of C 9 C aromatic hydrocarbons. Compound of Example No. 3 Calcium Dodecylbenzenesulfonate / Polyoxyethylene Ether (e.g. Atlox 3437F) Xylene II. Liquid concentrates A. Compound of Example No. 4 Xylene B. Compound of Example No. 5 Dimethyl sulfoxide C. Compound of Example No. 6 N-methylpyrrolidone% by weight, 0.0, 0.00, 0.0, 0.000 , 0, 00, 0, 0 0.5 74, 5, 00 D. Compound of Example No. 7 Ethoxylated castor oil Product called Rhodamine B Dimethylformamide III. Emulsions A. Compound of Example No. 8 Block Copolymer Polyoxyethylene /

  polyoxypropylene with butanol (eg

  Tergitol XH). Water B. Compound of Example No. 1 Polyoxyethylene / Polyoxypropylene Block Copolymer with Butanol% by Weight, 4.0

56.0 -

  , 00, 0 3.5 4.0 11.0, 00, 0 1.0 94.0, 00 33. IV. Wettable powders A. Compound of Example No. 3 Sodium lignosulfonate N-methyl-N-sodium oleyltaurate Amorphous (synthetic) silica B. Compound of Example No. 5 Sodium dioctyl sulfosuccinate Calcium lignosulfonate Amorphous (synthetic) silica C. Compound of Example No. 6 Sodium lignosulfonate N-methyl-N-sodium oleyl-taurate Clay kaolinite V. Dust A. Compound of Example No. 3 Attapulgite B. Compound of Example No. 4 Montmorillonite C.- Compound of Example No. 5 Bentonite D. Compound of Example No. 6 Diatomaceous earth% by weight, 0 - 3.0 1.0 71.0, 0O0, 0 1.25 2.75 16.00, 00 3.0 3.0 86.0.0 00 wt% 2.0 98.0, 00, 0, 0, 00, 0, 0, 00 1.0 99.0, 00 Water 91.5, 00 34. VI. Granules A. Compound of Example No. 7 Granular Attapulgite (passing through sieve with a mesh size of 0.841 mmn to 0.420 mm, ie 20-40 mesh) B. Compound of Example No. 8 Diatomaceous earth (passing through a sieve with a mesh size of between 0.841 mm and 0.420 mm) C. Compound of Example No. 1

Bentonite (passing through a sieve

  mesh size between 0.841 mm and 0.420 mm) D. Compound of Example No. 2 Pyrophyllite (passing through a sieve with a mesh size of 0.841 mm to 0.420 mm) VII. Microcapsules% by weight, 0, 0, 00, 0, 0, 00 0.5 99.5, 00, 0, 0, 00% by weight A. Compound of Example 4 encapsulated in an envelope wall polyurea Lignosulfonate desodium (by

  example product known under the trademark

  Reax 88 B) Water B. Compound of Example 5 encapsulated in a polyurea shell wall Potassium lignosulfonate (e.g. product known under the tradename Reax C-21) 49.2 0.9 49.9 , 00, 0 0.5 35. Water 89.5, 00 C. Compound of Example No. 6 encapsulated in a polyurea shell wall 80.0

Magnesium salt of lignosulphon

  fate (product known under the trademark - Treax 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, or are incorporated in aquatic environments in any suitable manner. The application of liquid compositions and particulate solids compositions to the soil can be carried out by conventional methods, e.g.

  machinery for the mechanical training of dust,

  telescopic and handheld spraying equipment and

  dust-forming agents by spraying. The com

  positions may also be applied from airplanes in the form of dust or spray as a result of their effectiveness at low doses.-The application of a

  Herbicide composition to aquatic plants is ordinarily

  made by adding compositions to aquatic environments.

  ticks in the area 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 the active ingredient to be used depends on a variety of factors, including

  taking the species of plant and its stage of development, the type and condition of the soil, the amount of rainfall and

  the specific acetanilide used. In the selective application

  pre-emergence to plants or soil, a dosage of from 0.02 to about 11.2 kg / ha, preferably from about 0.04 to about 36, 60 kg / ha, or suitably 1.12. at 5, 6 kg / ha of acetaniline

  is usually used. Rates lower or higher

  may be required in some cases. A person skilled in the art can readily determine

  From this description, including the examples below

  above, the optimum rate to apply in any case

ticular.

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

  ge to understand all classical "soils", as defined 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 soil, but also compost, fertilizer, manure (ordu-r

  res), humus, sand and the like, suitable for

hold the growth of plants.

  The present invention is not limited to the examples

  which has just been described, it is necessary to

  which may be subject to variations and modifications

will rat to the man of the art.

37.

Claims (7)

  1 - Compounds, characterized in that they have the mule: 0 ClCHc 2 / CH 2OR N R OR - R R2   R is isopropyl, n-butyl, isobutyl, sec-butyl?   allyl or 2-methylbutyl; R 1 is methyl, isopropyl, n-butyl or allyl and R 2 and R 3 are hydrogen, or methyl; provided that: R 1, R 2 and R 3 are each methyl when R is n-butyl, isobutyl or sec-butyl; R2 and R3 are each hydrogen when R is isopropyl, isobutyl or sec-butyl and R1 is isopropyl or n-butyl, and R2 is hydrogen and R3 is methyl when R is group 2 - methylbutyl or allyl and that R1 is the allyl group.   2 - Compound according to claim 1, characterized   in that it is formed by N- (isobutoxymethyl) -2'-methoxy-   3 ', 6'-dimethyl-2-chloroacetanilide.   3 - Compound according to claim 1, characterized in that it is formed by N- (n-butoxymethyl) -2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanilide.   4 - Compound according to revendicatioh 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- 6'-methyl-2-chloroacetanilide.   38. 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-chloroacétanilide. 8 - Compound according to claim 1, characterized   in that it is formed by N- (isobutoxymethyl) -2'-isopropyl   poxy-2-chloroacetanilide. 9 - Compound according to claim 1, characterized   in that it is formed by N- (sec-butoxymethyl) -2'-n-buto-   xy-2-chloroacetanilide. - Herbicidal compositions, characterized in that they comprise an adjuvant and a herbicidally effective amount of a compound having the formula: ClCH2C / CH2oR R3 OR1 P2   o R, R1, R2 and R3 are as defined in the claim 1.   11-Composition according to claim 10, characterized   in so far as the provisions of one   any of claims 2 to 9.   12 - A method for combating undesirable plants associated with sorghum, characterized in that it consists in applying, at the place where these plants are, a herbicidally effective amount of a compound having the formula: O H2 C ClC 2 CH 2OR R3 OR1   R 2, R 1, R 2 and R 3 are as defined in claim 1. Process according to claim 12, characterized in that the provisions of any one of the Claims 2 to 9.