FR2479204A1 - HERBICIDAL 2-HALOACETANILIDES AND COMPOSITIONS COMPRISING THE SAME AS ACTIVE INGREDIENTS - Google Patents

Abstract

N-HYDROCARBYLOXYMETHYL-2-HALOACETANILIDE COMPOUNDS HAVE THE FORMULA: (CF DRAWING IN BOPI) OR R IS A C-ALKYL OR ALCOXYALKYL OR ALKENYL OR ALKYNYL HAVING UP TO 5 CARBYRO ATGES, R THE METHYL OR ETHYL GROUP, PROVIDED THAT, WHEN R IS HYDROGEN, R IS THE ISOPROPYL GROUP AND WHEN R IS THE ETHYL GROUP, R IS THE ETHYL, N-PROPYL OR ISOPROPYL GROUP; THESE COMPOUNDS ARE USED AS ACTIVE INGREDIENTS IN HERBICIDE COMPOSITIONS USED IN VARIOUS HARVESTING PLANTS, ESPECIALLY CORN AND SOYBEANS, AS WELL AS COTTON, PEANUTS, KALEKILLA, WHITE BEANS, WHEAT AND SORGHUM.

Description

The present invention relates to the field of 2-haloacetanilides and to

  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 nitrogen atom of aniline

  and / or on the anilide nucleus, comprising radicals

  kyl, alkoxy, alkoxyalkyl, haloalkyl, halogen, etc. As the most relevant prior art with respect to the compounds of the present invention, which are

  characterized by the fact that they have a hydrocarbyl radical

  xymethyl on the anilide nitrogen, a trifluoromethyl radical in an ortho position and a methyl radical or, in

  specific cases, an ethyl radical or hydrogen in the

  ortho position, the nearest prior art known to the applicant appears to be the Belgian patent n

  810,763. The most relevant descriptions in the

  Belgian Patent No. 810,763 are the generic descriptions of N-

  alkoxyethyl or alkoxyethyl substituted alkyl-2-chloro

  acetanilides that can be substituted on the aniline nucleus

  from ortho and meta positions by one or more radicals

  chosen from among a large number of radicals including the

  halogenated, alkyl, alkoxy or trifluoromethyl (-CF3).

  More particularly, the list of compounds in Table II comprises species substituted with a -CF3 radical in an ortho position, without a substituent in the other position.

  ortho (compounds 37-48) and compounds having a

  -CF3 in a meta position, an ortho position being unsubstituted and the other ortho position being substituted by

  a methoxy radical (compounds n 22-25) or by a chlorine atom

  re (compounds 33-36). However, there is no description

  or examples of species in the patent

  Belgian Patent No. 810,763, 2-haloacetanilides substituted with a CF3 radical in an ortho position and with a methyl or ethyl radical in the other ortho position, as in the compounds

  of the present invention. In addition, the compounds in the

  Belgian patent No 810 763 are characterized by an alkoxy-

  alkyl substituted on the anilide nitrogen atom where the alkylene moiety should not have less than 2 carbon atoms between the nitrogen atom and the oxygen atom of the alkoxy moiety. In contrast, the compounds of the present invention are further characterized, in part, by substitution on the atom

  of anilide nitrogen with an alkoxylfitthyl radical. L! Importan-

  that of the distinctions indicated above between the composhs of the Belgian patent 810,763 and those of the present invention.

  will obviously appear with reference to the

  comparisons given here, clearly establishing the

  of the compounds of the present invention as a function of

  unitary activity, selectivity, range of con-

  Weed Control and Safety for Plants

to harvest or harvests.

  Other prior art documents

  less interesting than the Belgian patent No. 810,763 men-

  above, include US patents

  3,966,811 and 4,152,137, the German patent application

  No. 2,402,983, the British patent application

  2,013,188 filed on January 15, 1979, under the title: "clorace-

  tanilides, with herbicidal activity, a process for their manufacture and use "in the name of SCHERING AG and the South African patent No. 74/0767, although these references 3.

  contain generic descriptions of 2-haloacetanilides,

  which may include, among other substituents, a substitute

  by -CF3 on the anilide nucleus, the only descriptions

  of any species of these compounds in any of these references is found in US Pat.

  3,966,811 and in South African Patent No. 74/0767. Same -

  if so, neither US Pat. No. 3,966,811 nor South African Patent No. 74/0767 contain ortho-substituted species of CF3-substituted compounds or, more particularly, those compounds further substituted in the art. other position ortho with a methyl or ethyl radical; the only CF3-substituted species described in these patents are compounds substituted with CF3 in meta. In addition, like the Belgian Patent No. 810,763 indicated above, US Pat. No. 3,969,811 and South African Patent No. 74/0767 require

  that there are not less than two carbon atoms between the azo

  of anilide and the oxygen of the alkoxy part, a de-

  written in all the preceding references of the prior art, except in US Pat. No. 4,152,137 which, as mentioned above, does not describe at all

of species substituted with -CF3.

  Among the most interesting prior art

  mentioned above, only Belgian Patent No. 810,763 and

  South African Patent No. 74/0767 indicate heritable results.

  Bicides relating to N-alkoxyalkyl-2-haloacetanilides having -CF3 substitution on the anilide ring. same

  if so, these descriptions are vague, indefinite

  and incomplete. For example, Belgian Patent No. 810,763 does not

  only limited herbicidal results for a single

  is substituted with -CF3, that is to say compound 37 (which is the

  same compound as in Example 2), i.e. 2-trifluoromethyl

  rométhyl-N- (2'-methoxyethyl) -2-chloroacetanilide. In Table 3 of this Belgian Patent No. 870,763, it is shown that compound No. 37 destroys or seriously damages certain

  unidentified species of "Cuperus", Setaria, Digitalis

  and Echinochloa, with little damage to the

  vines Avena fatua and an unidentified species of 4.

  Lolium in some plants to harvest. The lack of identification

  of five of the six weeds tested

  prevents a significant evaluation of herbicidal efficacy

of this compound No. 37.

  Similarly, South African Patent No. 74/0767 discloses limited herbicidal results for a single -CF3-substituted compound, ie # 78,

  i.e. 2,6-dimethyl-3-trifluoromethyl-N- (2'-methoxy)

  ethyl) -N-2-chloroacetanilide. The only herbicidal results described for the compound -n 78 are in Example 5

  it is said that compound No. 78 has a very strong inhibition

  growth of four species of weeds

  of the grassy genus. However, there are no results in the

  or in the fields described in this South African patent.

  No. 74/0767 relating to the effect of compound No. 78 on any plant to be harvested or whether the compound exhibits selective control of any weed in

  any crop, making it impossible to evaluate

  significant evaluation of this compound, based on these results

  limited. In addition, the most interesting references

  described above, while describing herbicidal activity on a large number of weeds, do not describe results for N-alkoxyalkyl substituted

  -CF3, which are shown to control or suppress

  additionally and / or concurrently, in one or more plants to be harvested, hard-to-kill perennial weeds consisting of quackgrass, yellow and purple sedge, walnut and a wide range of annual weeds, grassy weeds, annual, difficult to destroy, such as

  young Johnson grass plants, brittle cane, -

  Alexander grass (Brachiaria plantaginea), panicums (Texas prosomillet and wild prosomillet), red rice and tepid grass (Raoul grass) while controlling or

  also removing other harmful weeds

  these and annuals, for example the fall panicum, the beautiful grass,

  quarter of lamb, the anserine, the fox tails (eg.

  5. giant and yellow magpie), wild grass, barnyard grass, garden spurts, velvet leaf, fieldnine, purslane, sesbania hemp, spiny AIDS, etc. A highly useful and desirable property of

  herbicides is the ability to maintain control or

  weed control over a prolonged period of time, the longer and better the period, during each harvest season. With many

  herbicides of the prior art, the control of

  herbs is adequate only for 2 or 3 weeks,

  or, in some higher cases, can be up to 4-6

  before the chemical loses its effective phytotoxic properties. Accordingly, one disadvantage of most prior art herbicides is their

  relatively short longevity in the soil.

  Another disadvantage of some prior art herbicides, somewhat related to longevity in the soil under normal atmospheric conditions, is

  lack of persistence of weed control.

  for significant rainfall that deactivates many

many herbicides.

  Another disadvantage of many prior art herbicides is the limitation of their use in specified types of solids, that is, while

  some herbicides are effective in soils with

  Inadequate amounts of organic matter make them inefficient in soils with high organic matter content or vice versa. It is, therefore, advantageous that a herbicide

  be useful in all soil types, from organic soil

  only light in 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 a

  pre-emergence application on the surface or in the form of

  corporation in the soil, that is, the mode of application

  before and / or after the introduction of the plant (method of

  6. cation cation of pre- and / or post-plant). It is highly desirable to be able to apply a herbicide in any

  which mode of application, whether by surface application

  this or by incorporation into the soil.

  Finally, a disadvantage in some herbicides

  is the need to adopt and maintain

  special handling because of the toxic nature of herbicides. As a result, another wish is that

herbicide be safe to handle.

  It is, therefore, an object of the present

  to provide a group of herbicidal compounds that overcome

  the disadvantages mentioned earlier in the

  and provide many benefits

  heretofore not obtained in a single group of herbicides.

  It is an object of the present invention to provide

  herbicides that control and / or suppress mumps

  annual and perennial weeds, difficult to destroy, as described above, while maintaining

  plants to be harvested in many crops, particularly

  maize and soybeans, and others including cotton, peanuts, rapeseed, white beans,

wheat and / or sorghum.

  It is another object of the present invention to

  provide herbicidal efficacy in the soil for periods

up to 12 weeks.

  Another object of the present invention is to

  provide herbicides that are resistant to leaching and

  lution due to high humidity conditions, for example

  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 soil-

  medium to heavy clay and manure (garbage).

  Another advantage. herbicides of this

  vention is there flexibility available in the mode of application

  tion, that is to say by applying pre-emergence

  this and by incorporation into the soil.

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

  present invention that they are safe and do not require

  special operating procedures.

  The objects listed above and other objects

  of the present invention will appear from the description

detailed below.

  The present invention relates to compounds having herbicidal activity, to herbicidal compositions containing these compounds as active ingredients and to a process

  herbicide use of these compositions in harvesting

your particulars.

  The Applicant has now found that a group

  selective 2-haloacetanilides, characterized by combinations of

  specific sounds of specific hydrocarbyloxymethyl radicals

  on the anilide nitrogen atom, a trifluoromeric radical

  thyle (-CF3) in an ortho position and a methyl radical

  or ethyl or a hydrogen atom in the other position

  tho, have remarkable herbicidal and

  unexpectedly compared to prior art herbicides, including homologous compounds

  most of those found in the prior art

interesting.

  A main feature of the compositions

  herbicides of the present invention is their ability to

  control or destroy a wide range of weeds,

  including weeds controlled by herbicides

  common weeds and, in addition, several weeds which, individually and / or collectively, have so far escaped control by a single class of known herbicides,

  while maintaining a security for the plants to be harvested

  to one or more of these harvesting plants

  including maize and soybeans, but also others such as cotton, peanuts, rapeseed, sorghum, wheat and brittle beans. While the herbicides of the prior art are useful for controlling a large number of weeds including, on occasion, certain resistant weeds, it has been found that the unique herbicides of this invention are

  were able to control or suppress

  resistant annual and perennial herbs, such as

  perennial weeds consisting of

  latan, yellow and purple sedges walnut, bad

  annual broadleaf weeds, such as Epidemic AIDS

  hemp, sesbania, beautiful grass, quarter of lamb, anserine and annual herbs such as young

  Johnson grass plants, brittle cane, orange grass

  xandre, Texas panicum, wild prosomillet, red rice

  spotted grass and other noxious weeds such as fall panicum, fox tails, barnyard grass, wild grass, etc. The reduction of weed feet has also been achieved in poor

  resistant grasses such as grass rag (grass with

  beautiful), the velvet leaf, the volubilis of the gardens, the niello of the fields, purslane, etc.

  The compounds of the present invention are

by the formula

ClCH C CH OR 2 \ / 2 -N

Q CF3

  R is a C1-5 alkyl group or an alkoxyalkyl group or an alkenyl group or an alkynyl group having up to 5 carbon atoms, and R is hydrogen, methyl or ethyl; provided that

  when R is hydrogen, R is the isopropyl group

1

  pyl, and when R is ethyl, R is the group 9.

ethyl, n-propyl or isopropyl.

  Preferred species of the present invention are compounds wherein R 1 in the above formula is methyl or ethyl and R is C 2 -C 4 ethyl. Preferred individual species of the present invention are as follows :

  N- (ethoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-

chloroacetanilide.

  N- (n-propoxymethyl) -2'-trifluoromethyl-6'-methyl

thyl-2-chloroacetanilide.

  N- (isopropoxymethyl) -2'-trifluoromethyl-6'-methyl

thyl-2-chloroacetanilide.

  N- (isobutoxymethyl) -2'-trifluoromethyl-6'-methyl-

2-chloroacetanilide.

  N- (ethoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-

chloroacetanilide.

  N- (n-propoxymethyl) -2'-trifluoromethyl-6'-ethyl-

2-chloroacetanilide.

  N- (isopropoxymethyl) -2'-trifluoromethyl-6'-

ethyl-2-chloroacetanilide.

  Other species of the present invention will be

described below.

  The utility of the compounds of the present invention,

  as active ingredients in herbicidal compositions

  formulated with these compounds, as well as the process for

  using them will be described below.

  The compounds of the present invention can be made by alkylating the anion of the appropriate secondary 2-haloacetanilide with an alkylating agent, under basic conditions as exemplified by way of example.

  in example 1. The modification of this N-alkylation process

  tion involves the in situ preparation of the halomethyl ethers.

  and alkyl used as starting materials in this

  assigned N-alkylation and is described in Example 2 for

  prepare another species of the present invention.

EXAMPLE 1

  This example describes the preparation of N- (ethoxymethyl)

  10. thyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide.

  2'-Trifluoromethyl-6'-methyl-2-chloroacetaniline

  (4.02 g) (0.016 mole), chloromethyl ether and

  (3.02 g) (0.032 mol) and benzyltrifluoride bromide were

  Thylammonium (2.0 g) (phase transfer catalyst) was mixed in 75 ml of methylene chloride in a 500 ml round bottom flask equipped with mechanical stirrer and thermometer. Soda (50%) (15 ml) was added all at once with vigorous stirring, giving rise to

  an exotherm up to 26 C. After about 5 minutes, the

  Gas-phase matography indicated that the reaction was complete. After 15 minutes, water and ice were added, the layers separated and the organic layer washed

  with 2.5% sodium chloride, dried, filtered and removed.

  The dark coloring residue was distilled on a

  Kugelrohr, and 3.4 g of a fraction of yellow oil,

  boiling at 110-115 ° C at 0.1 mm Hg, were pooled.

  This fraction was absorbed in cyclohexane and purified by high performance liquid phase chromatography, in

  using 20% ethyl acetate in cyclohexane.

  Subsequent distillation of the peak fraction by the

  Kugelrohr's positive yielded 3.2 g (65% yield) of colorless oil, m.p. 100-110 C at 0.1 mm Hg; at rest, a

  white solid, m.p. 41 C-43 C, separated by crystallization

tion.

  Analysis for C13H15ClF3NO2 (%) Element Theory Found

C 50.41 50.02

H 4.88 4.81

N 4.52 4.38

EXAMPLE 2

  This example illustrates the use of an improved process

As an alternative, the compounds of the present invention are

  This invention can be prepared. A feature of the process of this example is the in situ formation of the agent

  of alkylation, thereby performing a more efficient operation.

  this, more economical and simpler.

  An ethylene glycol monomethyl ether slurry in an amount of 7.3 g (0.096 mole) and paraformaldehyde in an amount of 1.44 g (0.048 mole) in 100 ml of methylene chloride as solvent was cooled in a water-ice bath and 5.9 g (0.048 mole) of acetyl bromide were added. After stirring for about 45 minutes,

  4.03 g (0.016 mole) of 2'-trifluoromethyl-6'-methyl-2-

  chloroacetanilide and 2.0 g of benzyltriethylammonium chloride

  minium. 50 milliliters of 50% NaOH were added all at once. Gas chromatography indicated a complete reaction after about 5 minutes. Ice and

  water were added to the mixture to effect the separation

  phase and the organic phase was then separated, separated

  filtered and removed. The residue was distilled under vacuum on a short-path still to provide 4.2 g (77% yield) of clear, colorless oil, bp 150-160 ° C.

mm Hg.

  Analysis for C14H17C1F3NO3 (%) Element -Théorie Trouvé

C 49.49 49.33

H 5.04 5.04

N 4.12 4.08

  The product has been identified as N- (2-m & -

  thoxyéthoxyméthyl) -2'-trifluoromethyl-6'-methyl-2-chloroacéta-

  nilide. If we let the N-alkylation process provide

  temperatures too high or too low, various

  can be produced, for example a sec-anilide,

  the corresponding imidate, a-alkoxyamide or diketopiperene

  Razines. These impurities can be removed by washing the

  organic cheese with a dilute aqueous solution of salt or

  acid solution, for example 2-3% NaCl or 5% HCl.

EXAMPLES 3-13

  By following substantially the same procedures, with the same amounts of reactants and the same general reaction conditions as those described in Example 1 or 2, but substituting the appropriate starting sec-anilide and the appropriate alkylating agent to obtain the final product, other compounds are prepared according to the formula above, these compounds are identified in Table I. 2479f04 12.

TABLE I

1 -. iExperiment -I c-I Tru

  Exem1 Compound Formula empi - P.E. oC El-Calcu- Trou-

  ply (mm Hg) lége.ve r _ _ _ _ _ _ _ _ ___ ___ _ _ _ _ _ t _ _ _

  f n 7.TI4 - "TTr 1 1rlr -, C sA, -

  ## STR5 ## - (trifluoroethyl) -2'-trifluoro (0.05)

Jrométhyl-2-chloro-

Iroacetanilide i

C14H C1 F37NO2! 110-

(01, -1)

C1 4H1 7C! F3NO2

  C15H19ClF3NO2 - C (0,1) - C (0,1) C12H13C1F3NO2 Oil

C15H19C1F3NO2

C15H19C1F3NO2

C14H15C1F3NO2

- 138 C

(0.05)

- 142 C

(0.05)

123- C (0,1)

4! N- (n-propoxymé-

ithyl) -2'-tri-

fluoromethyl

6'-methyl-2-

chloroacétani-

N- (isopropoxy)

methyl) -2'-tri-

fluoromethyl

6'-methyl-2-

chloroacétani-

lide

6 N- (isobutoxy-

methyl) -2'-tri-

fluoromethyl-6'

methyl-2-chloro-

acetanilide

7 N- (methoxymethyl)

thyl) -2'-tri-

fluoromethyl

6'-methyl-2-

chloroacétani-

lide

8 N- (n-butoxymethyl)

thyl) -2 '-tri

fluoromethyl

6'-methyl-2-

chloroacétani-

lide

9 N- (sec-butoxy-

methyl) -2'-tri-

fluoromethyl

6'-methyl-2-

chloroacétani-

lide

N- (allyloxymethyl)

thyl) -2'-tri-

fluoromethyl-61-

methyl-2-chloro-

acetanilide

%! OF 41

H 4.88

N. 4.52

  51.94, 29 4.33 51.94, 29 4.33 53.34, 67 4.15 48.47 4.43 4.74 53.34, 67 4, 15 53.34, 67 4.15 52 , 27 4.70 4.35 CHN c HN c HN c HN c HNCHN c HN

DU, DZ

  4.8 '4.4 (51.8C, 17.24E 51.69, 23 4.22 53, 0.61 4.01 49.94 4.44 4.70 53, 32, 68 4.1 53 , 2, 6 4.1 52.1 4.7 4.3 J salt P1 jiiiqi 13.

TABLE I (Continued) -

TABLE I (Continued)

N- (propargyloxy

methyl) -2'-tri-

fluoromethyl-6'

methyl-2-chloro-

acetanilide

N- (isoamyloxymé-

thyl) -2'-tri-

fluoromethyl-6'

methyl-2-chloro-

acetanilide

N- (ethoxymethyl

2'-trifluoromethyl

thyl-6'-ethyl-2-

chloroacetanilide

N- (n-propoxymé-

thyl) -2'-tri-

fluoromethyl-6'

ethyl-2-chloro-

acetanilide

N- (isopropoxy

methyl) -2'-tri-

fluoromethyl-6'

ethyl-2-chloro-

acetanilide C14H13C1F3NO2 Oil

14 13 32

  C16H21 ClF3NO2 C14H17ClF3NO2 C15H19 ClF3NO2

C15H19C1F3NO2

C H N C C

(0.05) H

NOT

133- C

 C H

(0,02) N

C-color oil - C

(0.01)

H N C H N

52.59 52.44

4.14 4.14

4.38 4.34

  IJ 54.63 6.02 3.98 51.94, 29 4.33 53.34, 67 4.15 53.34, 67 4 15 54.66 6, 03 4.00 51.32, 26 4.39 53.74, 77 4.16 53.43, 74 4.18

  Starting materials consisting of anilides se-

  used in the examples above, to pre-

  compounds of the present invention are suitable

  prepared by conventional chloroacetylation of the appropriate primary amine, as indicated by way of example in

Example 14 below.

EXAMPLE 14

  This example illustrates the preparation of the secondary anilide starting material used to prepare a species of the compound of this example, i.e.

the compound of Example 13.

  2-trifluoromethyl-6-ethylaniline, in quantitative

  6.0 g (0.03174 mole) was dissolved in 75 ml of

  luene and carefully added 3.77 g (0.033 mol) of chloroacetyl chloride. The temperature of the resulting slurry was raised to reflux temperature and held for 4 hours. Then the mixture was diluted

  with an equal volume of hexane and the mixture was allowed to stand

  14. Ge. The product crystallized and the resulting solid was filtered and air dried to give 5.8 g (69% yield); the filtrate was removed to produce another 2.7 g of white solid, m.p. 121-124 C (sealed tube) Analysis for CHmClF3 {t EImentment Theory Found

C 49.73 49.36

HI 4.17 4, O9

N, 5.27, 5.38

  The product has been identified as 2'-trifluoromethyl

  thyl-6'-ethyl-2-chloroacetanilide.

  Primary amines of the type used to prepare secondary anilides by haloacetylation, as described above, are known in the literature; see, for example, U.S. Patent No. 3,966,811 and the application for

British Patent No. 2,013,188.

  As noted above, the compounds of the present invention have been found to be effective as herbicides, particularly as pre-emergence herbicides, although post-emergence activity has also been shown. The pre-emergence tests referred to here include both tests in a greenhouse and tests in the

  fields. In tests in a greenhouse, the herbicide is applied either by surface application after planting

  seeds or vegetative propagules, either by incorporation

  in a certain quantity of soil to be applied in the form of a cover layer on the experimental seeds, in pre-seeded experimental vessels. In the

  in the field, the herbicide may be applied by

  corporation before the plant ("P.P.I.") in the soil, that is,

  say that the herbicide is applied to the soil surface and then

  incorporated in by means of mixing, followed by planting

  seeds to be harvested, or the herbicide can be applied to the surface (surface application,

  "S.A.") after the plant seed to be harvested was planted

3 5.

  The experimental method of surface application ("SA") used in the greenhouse is carried out as follows: containers, for example aluminum boxes typically 15. 24.13 cm × 13.34 cm × 6.99 cm, or plastic pots 9.53 cm x 9.53 cm x 7.62 cm, having drainage holes in

  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

  seeded with plant species to experiment with,

  green with a layer of 1.27 cm of experimental soil. The her-

  bicide is then applied to the soil surface, for example with a belt spraying device, at the rate of 187 l / ha under 2.11 kg / cm. Each pot receives 0.75 cm of water in

  as irrigation from above and pots are then

  planted on greenhouse benches for later irrigation

  from below, as necessary. As a method of

  Alternatively, top irrigation can be

  deleted. Observations of herbicidal effects are

  about three weeks after treatment.

  Treatment with soil incorporation herbicides ("S.I.), used in the test in greenhouses, is as follows: Good top soil quality is placed in

  aluminum boxes and compacted to a depth

  from 9.5 mm to 1.27 cm 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, after seeding

  or addition of vegetative propagules, is weighed in a box

  you. The soil and a known amount of the active ingredient

  in a solvent or in the form of a suspension of

  wettable, are fully mixed, and used for

  cover the prepared boxes. After treatment, the boxes are given an initial irrigation of water from above, equivalent to 0.64 cm of rainfall, then humidified by irrigation

  from underneath as necessary to give adequate moisture

  quate for germination and growth. As a method of

  Alternatively, top irrigation can be omitted. Observations are made about two to

  three weeks after seeding and treatment.

  16. 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, the herbicides were applied by incorporation into the soil and with humidification by underwater irrigation only. Herbicide evaluation was obtained.

  average of a fixed scale, based on the percentage of endom-

  of each plant species. The evaluations are defined as follows% of control Evaluation

0-24 0

-49 1

-74 2

-100 3

  Not determined 5 Plant species used in a series of tests, the results for these species being presented in

  Table II, are identified by a letter according to the

  Next: Canada Thistle E Lamb Quarter t Herb Johnson B Nielle Fields F Beautiful Grass J Fluffy Brome

  C Yellow Carex G Carex Velvet Leaf

D Volubilis gardens walnut yard

H Grass of charla-

tan 17.

TABLE II

  Pre-emergence activity Compound of Example 1n kg / haA kg / ha! A 11.2, 6 11.2, 6 11.2, 11.2, 6 11.2, 6 11.2, 6 11.2, 6 11.2, 6 11.2, 6 11.2, 6 11.2, 6 11.2, 6 11.2, 6 B 3 2 2 1 3 2 3 1 2 0 3 2 3 0 2 2 3 1 3 2 3 1 3 2 3 2 3 2 3 1 3 1 3 1 3 2 3 1 3 2 3 2 Plant species CDEFGHIJ Kt | Composed of the example

3 3 3 3

2 33 3

1 32 2

1 32 3

2 33 3

2 33 2

2 3 3 3

1 2 3 3

2 33 3

0 33 3

1 33 3

0 13 3

2 23 0

1 13 0

0 23 3

0 33 3

2 33 3

1 23 3

1 33 3

1 23 3

1 33 3

1 23 3

O 2 3 3

0 21 2

2 33 3

2 33 3

3 3 3 3 3__ - J

3 3 3 3 3-

3 3 3 3 3

3,333 3

0 22 3 3

3 32 3 3

3 31 3 3

3 33 3 3

3 33 3 3

3 33 3 3

3 31 3 3

3 3 3 3 3

* 3 33 3 3

2 31 3 3

1 31 3 3

3 3 3 3

3 3 2 3 3

3 3 3 3

3 3 1 3 3

3 3 3 3

3 3 0 3 3

3 3 0 3 3

1 3 1 3 3

3 3 0 3 3

3 3 3 3

3 3 3 3

3 3 2 3 3

  The compounds were further tested using the

  procedure above on the following plant species

  : L Soya M Sugar beet N Wheat O Rice P Sorghum R Hemp sesbania E Quarter lamb F Beautiful grass C Velvet leaf J Fluffy brome

B Nielle Fields S Panicum Spp.

  Q Wild Buckwheat K Barnyard Grass D Garden Volubilis T Wild Grass M m M N Ln Ln Ln Ln Ln M M m M i (N N M m m M m m m m m

M MCN miM7 ri 4C r-lOC M M r

cq00 C 0 m m -iHi m i 000

N 0000 00 0 -100000 0 0

  N rq - c O O O O r O O Q O m m o r m C 00 M M 0r-0

: N M - CON, 0 0 00 OO O

  ## STR5 ## wherein R is not less than 0.001 mol%, and most preferably less than 0.001 mol% 0FN0C00 CiN 0 0 0 cq CN OO 0 <-i 0 0 0 0 Ci-OONNO -00000 N -10 0 MMN r- 0 i r-1 0 0 0 0

-0000 000 000000

  N o r-i n O r N O O L N7 H O O O N VD r-

N 00 L r-

  rD H N O O Lr-0 0 0 C% w -0 r-t Ln N CO Lnr-O O r-I N OQ O TI r-sO o n 000 mcirmm O M ri 0 N M en cN o CiCioio o M M N o o r-i o O O O

Co M M r-i H-

  CiNOCO M rrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrrr CU C7% fl. ## EQU1 ## where: ## STR1 ## E-1 mm QP; o z x :: -. ta3 o- r -% a) PL x U r- Ci ci i Ci (O M C ci N n r-i0000 M Mr H - 1 i Ci Ci C n ci N C C N O O O N O

0 0 0 S O

mOmO0nH mN0 O

N 1 I 10

  0000 N N 00r-i Noe 10 00 Lo -Q OO r-O O O Ln CiCiCiCi M Mf N CiN N o M N C ri m0Om N000 CirHO O N O 0 r-l

N1 0 0 0

O-0

ci i ci ci r

  ## EQU1 ##

M M N N O

C N r-i-I

OCO OO

  1r-I N N N r-i0000 N% D r- NCO Ln O-O - r-t N OC

LO0-0O'O

-0 Ln N Co ri Ci M O ri Mi r-i-I

H O00 O0

  ## EQU1 ## ## STR2 ##

m N H r-

  M M r-I r-0 0 riCenN r-t O CN'r-1 QO0

OOr

  N tO0r-i N cr Ln Q Lr-i0 00 o - L1 N

- " '- 7-

19. TABLE III (Continued)

2 2 3 3 32

1 2 3 3 1 1

1 2 2 3 2 0

0 0 0 0 00

3 3 3 3 3 2

1 2 3 3 3 0

0 2 2 2 2 0

0 1 0 1 0 0

00000 0

0 3 3 3 3 1

o 3 1 3 1 1

0 2 1 2 1 0

0 1 0 0 00

0 1 0 0 0 0

1 2 2 3 3 1

1 2 1 2 3 0

0 1 0 1 0 0

0 5 0 0 0 0

2 3 3 3 3 2

1 2 3 3 3 0

2 2 3 3 1 0

0 1 1 1 00

00 00 0 0

  0 0 0 3 3 3 0 -01 O 0 5 0 0 03 1 0 0

2 3 1 3 3 3 3

2 2 0 3 3 3 3

1 1 0 3 3 3 3

2 1 0 2 3 3 3

0 0 0 0 3 3

3 3 0 3 3 3 3

2 3 0 3 3 3 3

3 2 0 3 3 3 3

3 3 1 3 3 3 5

2 2 0 3 3 3 5

1 1 0 3 3 3 5

O 000135

2 1 0 3 3 3 3

2 203 3 3 3

1 0 0 1 2 3 2

3 3 2 3 3 3 3

2 3 0 3 3 3 3

1 3 0 3 3 3 3

0 2 3 3 3

5 0 o 0 2 2 We found

  that the herbicides of this

  vention possessed superior properties so

  unexpectedly as pre-emergence herbicides, more particularly

  specifically for the selective control of annual and perennial weeds that are difficult to destroy, including perennial weeds such as quack grass,

  the yellow and purple sedges of the walnut trees,

  broadleaf nematodes, such as thorny AIDS,

  hemp sesbania, the beautiful grass, the quarter of lamb, the

  and annual grasses such as Brittle Cane, Alexander's Herb, Johnson's Herb, Texas panicum, wild prosomillet, red rice, pecking herb (Raoul's herb, Rottboellia exaltata), fox tails (eg green, yellow and giant), barnyard grass and the

  big wild grass. The reduction of bad feet

  bes was also obtained on other resistant species such as grass cloth (ragweed), velvet leaf, garden whirlwind, field noodle, the, 6, 1.12 0.28 0.056

0.0112

, 6 1.12 0.28 0.056

0.0112

, 6 1.12 0.28 0.056

0.0112

  , 6 1.12 0.28 0.056, 6 1.12 0.28 0.056

0.0112

  20. Purslane, etc. Selective control and increased weed control mentioned above with herbicides

  of the present invention have been found in a large

  number of plants to be harvested including, in a particularly interesting way, maize and soybeans, but also others such as cotton, peanuts, rapeseed, brittle beans (white beans), wheat and sorghum;

  however, these last two plants to be harvested are usually

  are generally less tolerant to the herbicides of this

  vention than the other crops to be harvested; this reduced tolerance can be improved by using

  safety products, ie antidotes to the her-

bicides.

  In the discussion and the tables of results

  below, we refer to the application rates of herbicides

  symbolized by e1 "GR85", these rates are given in ki-

  logrammes per hectare (kg / ha). GR15 defines the maximum rate

  herbicide required to produce 15% (or less) of

  plants to harvest, and GR85 defines the minimum rate

  required to obtain 85% inhibition of weeds.

  The GR15 and GR85 rates are used as measures of the

  potential commercial performance, being of course

  that suitable commercial herbicides can

  damage to more or less important plants

  within reasonable limits.

  Another guide to the effectiveness of a chemi-

  that as a selective herbicide is the "selectivity factor

  "(" FS ") for a herbicide in particular plants to be harvested and in particular weeds.The selectivity factor is a measure of the relative degree of safety for

  the plants to be harvested and the damage to the bad her-

  besides, and is expressed in terms of the GR15 / GR85 report, that is,

  ie the GR15 rate for the crop to be divided by the GR85 rate for the weed, both being in kg / ha. In the tables below, selectivity factors

  are shown in parentheses after the GR85 rate for each

21.

  that weed; the symbol "NS" indicates "non-selective".

  Marginal or undetermined selectivity is indicated

by a dash (-).

  Since the tolerance for the plants to be harvested and the control of the weeds are interrelated,

  a brief discussion of this relationship according to

  selectivity is significant. In general, it is desirable that safety factors for plants

  to harvest, that is to say the tolerance values of herbicides

  These higher concentrations of herbicides are frequently desired for one reason or another. Reciprocally, it is desirable that

  weed control rates are low, ie

  that the herbicide has a high unit activity,

  for economic and possibly ecological reasons.

  However, low application rates of a herbicide

  may not be adequate to control some of the

  herbs and a higher rate may be required. As a result, the best herbicides are those that control the

  more weeds with the least amount of

  herbicide and which provide the greatest degree of

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

  this for the plants to harvest. As a result, we use

  selectivity factors (defined above) for the quan-

  proud of the relationship between crop safety

  ter and weed control. Referring to

  the safety factors indicated in the tables, plus the

  their numerical value is high, the greater the selectivity of the herbicide for weed control in a

plant to harvest given.

  In order to illustrate the superior properties of

  unexpectedly of the compounds of the present invention, both on an absolute basis and on a relative basis, comparative tests were conducted in the greenhouse with prior art compounds most closely related, from the chemical structure point of view, to the compounds of this

  invention. These compounds of the prior art are identical

  22. listed as follows (using the same nomenclature as for the compounds of the present invention):

  A. N- (methoxyethyl) -2'-trifluoromethyl-2-

  chloroacetanilide. B. N- (ethoxyethyl) -2'-trifluoromethyl-2chloroacetanilide. In Tables IV and V, results of pre-emergence herbicidal activity are presented, comparing

  the relative effectiveness of the compounds of the present invention.

  tion and these prior art compounds as

  selective herbicides against annual weeds

  the resistant and boring, constituted by the quack grass and the yellow sedge of the walnut trees in the soja and

  the but, respectively. These weeds are commonly

  associated with major crops, such as maize and soybeans. Experimental results in

  Tables IV and V were obtained under identical conditions.

  ticks and represent the average of two tests performed in

  double (except for the compound of Example 13 which was

  in a single comparative test). The experimental procedure

  rimental was the same as that described for Tables II and III, but modified by the application of initial top irrigation equivalent to 0.64 cm of rainfall; further humidification was accomplished by underwater irrigation. "NS" means non-selective within the experimental limits.

-TABLE IV

  GR15 rate GR85 rate (kg / ha) (kg / ha) Compo- Sojas Grass of charla- Carex yellow of tan walnut trees

A> 2.24> 2.39 (NS) 1.13 (1.98)

B 1.96 0.61 (3.21) 0.44 (4.45)

  Ex. 1 2,67 0,17 (15,6) 0,17 (15,6) Ex. 3 1,68 0,27 (6,22) 0,19 (8,84) Ex. 4 1, 12 0.13 (8.62) 0.17 (6.59) Ex. 5 1.46 0.26 (5.62) 0.26 (5.62) Ex. 13 2.13 0.25 (10, 65) 0.17 (12.53) 23. Referring to the results in Table IV,

  it will be appreciated that each compound of the present invention

  felt that selectivity factors were excessively higher than

  vés (values in brackets), both against quackgrass and against yellow sedge of walnuts in soybeans,

  than those of the compounds of the prior art. More by-

  In particular, it is noted that unitary activities (phytotoxic

  relative xicity per herbicide unit) of the compounds of the pre-

  are significantly higher, against the her-

  quince and yellow walnut sedge, than those of the prior art compounds, while maintaining a

  security vis-à-vis the plants to harvest. We will now note

  safety against the plants to be harvested. Particularly noteworthy are the selectivity factors.

  of the compounds of Examples 1 and 13.

  Other comparative results showing the effectiveness

  relative strength of the compounds of the present invention by

  compared with the compounds of the prior art indicated below.

  above, against quack grass and yellow sedge from walnut trees in maize, are presented in Table V.

TABLE V

  Referring to the results in Table V,

  it will be appreciated that each compound of the present invention has

  were excessively higher selectivity factors at the same time, against the quack grass and the yellow sedge

  walnuts in maize, than those of the compounds of the technical

GR Rate GR Rate

85

t______ (kg / ha) _k / _ __ha) _-

  Compo-- But Charla-i Grass Carex yellow walnut

A> 2.24> 2.39 (NS) 1.13 (1.98)

B 0.81 0.61 (1.33) 0.44 (1.84)

  Ex. 1 0.76 0.17 (4.47) 0.17- (4.47) Ex. 3 1.94 0.27 (7.19) 0.19 (10.2) Ex. 76 0.13 (5.85) 0.17 (4.47) Ex. 5 1.83 0.26 (7.04) 0.26 (7.04) Ex. 13 2.24 0.20 (11) , 2) 0.17 (13.18) 24. interior. Again, it is noted that the unit activities of

  compounds of the present invention were significantly higher than

  against the yellow sedge of walnut trees and the grass of charla-

  tan, than those of the compounds of the prior art, while maintaining a safety for the plants to harvest. In particular, the major selectivity factors for

  Examples of examples 3,5 and 13, especially by comparison

  reason with those of the compounds of the prior art.

  According to the comparative results presented in Tables IV and V, it will be apparent that the compounds of

  present invention had superior herbicidal efficacy.

  unexpectedly against weeds vi-

  herbicide-resistant, quackgrass and yellow walnut sedge in two main crops, ie soybeans and maize, compared to compounds A and B which are the most

  intimately related in the prior art.

  In addition, herbicide results from pre-emergence

  other tests have established that compounds

  The present invention also controlled selectively

  the quack grass, the yellow sedge of the walnut trees and / or

  very weeds in one or more of the plants to

  harvested from cotton, peanuts, haric

  white costs, wheat, sorghum and / or rapeseed. For example, in Table VI, results are presented showing the herbicidal selectivity of the compounds of Examples 1 and 3 against quackgrass in rapeseed, kidney beans, sorghum and wheat. Unless otherwise specified, tests in

  greenhouses in Table VI and in other tables below.

  below implicated herbicide treatments by soil incorporation and top-up irrigation, followed by underwater irrigation, as described above. 25.

TABLE VI

  The compound of Example 1 was also tested

  in the fields to determine its selectivity of pre-emerald

  against fox tail (spp), barnyard grass

  and the white prosomillet in several crops; the results

  States (representing three duplicate tests) are shown in Table VII for both surface application (S.A.) and incorporation-in soil (P.P.I.

  i.e., incorporation before the plant) of the herbicide.

  The seeds were planted in a layer of fine silty loam seedlings, with intermediate moisture. The seeds were planted to a depth of 5.08 cm. A first fall

  rain (0.51 cm) occurred two days after treatment.

  the second rainfall (0.64 cm) two days after treatment; cumulative rainfall 22 days after

  the treatment was 4.57 cm. Observations were made

* lised 6 weeks after treatment.

  GR15 rate GR85 rate (k / ha) '(kg / ha)

  Rape Rapeseed Beans Sorghum! Wheat Grass of charla-

  brittle tan Ex. 1 0.86 - - - 0.12 (7.2)

- 0.90 - - 0.12 (7.5)

- - 0.24 - 0.12 (2.0)

- - - 0.21 0.12 (1.8)

Ex. 3 1.9 - - 0.28 (6.8)

- 2.24 - - 0.28 (8.0)

- - 0.84 - 0.28 (3.0)

- - - 0.28 0.28 (1.0)

TABLE VII

Percentage of inhibition

  Compo- Rate Mode But But So- Ara- Co- Sor- Hari- Rapeseed Grass Tail of Proso-

  Apples (kg / ha) of black cotton gho cot -renard low-millet plicachamp dredes blanc (Spp) court blanc

(soft) ... l ....

Ex.l S.A. 0.56 0 _ O 0 _ 0 62 63 63

1,12 0 0 5 0 13 3 8 0 92 93 83

2.24 0 7 0 8 20 17 20 5 93 93 95

  4.48 15 27 13 22 25 77 32 33 98 98 97

  P.P.I. 0.56 0 0 5 17 13 32 23. 0 75 75 23

1,12 0 3 7 13 32 53 10 0 90 93 58

  2.24 5 27 20 15 37 92 37 15 98 98 80

  4.48 32 40 40 28 82 98 43 40 100 100 85

  (b) 27. The results in Table VII show that, in

  In general, the compound of Example 1 had a better performance

  as a selective herbicide in the mode of application

  on the surface, only when incorporated into the soil.

  In particular, in top-down application tests

  the herbicide selectively controlled the three

  herbs in the test, for higher application rates.

  at 0.58 kg / ha, while maintaining safety for the crops to be harvested (ie up to about 15% maximum damage) in field corn and soybeans up to 4.48 kg / ha and safety in soft maize (peanuts) and rapeseed at over 2.24 kg / ha and in cotton, sorghum and white beans just under 2.24 kg /Ha. In the PPI tests, the compound of Example 1 selectively controlled fox tail species and backyard grass at less than 1.12 kg / ha, while maintaining a safety for the plants to be harvested in the field.

  but fields, peanuts and rapeseed at rates

  up to 2.24 kg / ha and slightly below 2.24 kg /

ha for soya.

  Further field test results for the compound of Example 1 showed selective control of pre-emergence of other weeds in soybeans, maize, cotton and / or peanuts, such as purple sedge. walnut trees, the giant fox's tail, the yellow fox's tail, the quarter of lamb, the garden's whirlwind, the niello of the fields, the velvet leaf, the beautiful grass

  of Pennsylvania, thorny aids, purslane, wild grass

  vulture, the grateron, the Texas panicum, the so-called pusley grass of

  Florida and / or the hairy little burdock. The persons

  Those skilled in the art will understand that this

  are not all the weeds listed that are

  Controlled in all the plants to be harvested indicated, under all climatic conditions, soil,

  moisture and / or application patterns of herbicides.

  Selectivity results for control of previous weeds in incorporated plants 28.

  soya, maize, cotton and peanuts,

  siess tests in fields, in various locations,

  in various soil conditions, humidity, etc. are

  collectively in Tables VIII-XI, respectively

  is lying. In the tables, "SAT" means "weeks after treatment" of the plants with the herbicide, applied either by surface application (S.A.), or by incorporation before

  the plant ("P.P.I.") in the soil; rate of ap-

  -nlication for each crop combination to be harvested /

  Seeds are presented according to the GR15 and GR85 rates

  (defined above); the GR15 / GR85 report providing the

  selector feeder "F.S."; "N. S." indicates non-selective and a dash (-) indicates marginal or indeterminate selectivity, for example because the actual rates GR15 and GR85 were

8

  higher or lower than the maximum or minimum rates used in the indicated test). In Tables VIII-XI, a blank space indicates that the plant species was not present in a particular experimental lot or

  that the results were not obtained or were less important than

  other results presented, for example,

  some observations for 3 SATs are suppressed in favor of 6 SAT results, or the results for 6 SATs are

  deleted because the results for 3 SATs were defined

tive.

TABLE VIII

Co-ob2io Md A -R5 / R 5.S

  iCom- Combination Mode SAT GR, GR F.S.

posed plant to harvest 8

ter / bad plica-

  ___ grass tion 1 i _ .. -I Ex.1 Sojas / tail of S.A. 3 giant fox 5> 4, 48 / <l, 12 (> 4.0)

S.P.I. 3

> 4.48 / <1.12 (> 4, O)

8> 4.48 / <1.12 (> 4.0)

  Sojas / tail of S.A. 6 2,52 / 2,8 (NS) yellow fox

P.P.I. 1.4 / <1.12 (> 1.3)

  Sojas / quarter S.A. -6 2.52 / 2.52 (1.0) lamb

P.P.I. 6 1.4 / 2.8 (NS)

  29. Sojas / beautiful Pennsylvania grass The results in Table VIII show that the compound of Example 1 selectively controls the tails

  of giant and yellow fox, the quarter of lamb and the beautiful

  be from Pennsylvania in the soya, from 6-8 SAT, by

  the modes of application S.A. or P.P.I.

TABLE IX

  The results in Table IX show that the compound of Example 1 selectively controls the tail of

  giant fox in the maize, from 6-6,5 SAT, by the

  S.A. or P.P.I. the selectivity for the volume

  of the gardens and the field meal was not deter-

  at the experimental rates, but the removal of these

herbs was brent.

  Com- Combination Mode! SAT GR15 / GR85 F.S.

GR15 / G85

  plant yielding crop / bad plastering Ex. 1 But / tail of SA 6 4.48 / <1.12 (4.0) giant fox SA 6.5> 7.84 / 8.4 (NS)

P.P.I. 6 4.76 / 1.96 (2.5)

P.P.I. 6.5> 6.72 / 4.48 (1.5)

  But / volubilis S.A. 3> 4.48> 4.48 (-) gardens S.A. 6> 4.483> 4.48 (-)

P.P.I. 3.76 /, 4.48 (-)

P.P.I. 6 4.76 /> 4.48 (-)

  But / niella S.A. 3> 4.48 / 4.48 (-) of the fields S.A.- 6> 4.48 /> 4.48 (-)

P.P.I. 3.76 /> 4.4 (

P.P.I. 6 4.76 / 4.48 ()

_ _ 3

30.

PAINTINGS

  Com- Combination Mode SAT GR / GR F.S.

G15 / G85.

plant to be harvested for appli-

  Ex.1 Coton / carex S.A. 6 3.64 / 1.68 (2.17) violet of S.A. 9.3, 36 / 2.24 (1.5)! walnut

P.P.I. 6 3.36 / 4.2 (NS)

  Cotton / AIDS S.A. 6 3.64 / 3.08 (1.18) J Thorny S.A. 9 3.36 / 4.76 (NS)

P.P.I. 6 3.36 / 4.76 (NS)

  Cotton / purslane S.A. 9 3.36 / 1.96 (1.7) Cotton / grass S.A. 7 l, 4 / <1.12 (> 1.25)

wild

  hairy) P.P.I. 7 0.84 / 1.12 (NS) Cotton / grateron P.P.I. 7 0.84 / <1.12 (-) - ,,, _3_ _Na__t __ __

  The results in Table X show that the

  posed in Example 1 selectively controlled the purple sedge

  walnut and purslane up to 9 SAT, thorny AIDS

  only at 6 SAT and wild grass up to 7 SAT; the control of the

  Grateron was marginal and indeterminate.

  Table XI presents the results of

  pre-emergence activity for the compound of Example 1 against three resistant annual weeds, that is, Texas panicum, hairy little burdock and grass

  pusley in peanuts for periods of time

  from up to 12 SAT. The results in Table XI represent the average of three duplicate trials

  in sandy loam soil with 1.3% organic matter

  ganic, 79.2% sand and 10% clay, the herbicide

being applied on the surface.

TABLE XI

  _____ __ 'Percent inhibition IZ Texas pa- Burdock Pusley Peanut Hairy Star-petunia Florida Com- SAT SAT SAT SAT laid (kg / ha) 4 8 12 4 8 124 8124 8 12 Ex. 1 2.24 5 O 0 50 67 40 78 40 90

3.36 10 0 0 68 63 55 85 600

  The results of Table XI show that the compound of Example 1 selectively controls Texas panicum in peanuts for a period of up to 10 days. at 8 weeks and provided a high degree of control, even for 12 SAT, at about 4.48 kg / ha; the selective control of the hairy little burdock was

  presented for 3.36 kg / ha for 8 weeks, a

  was maintained for 12 SAT at 4.48 kg / ha and

  selective control of the so-called Florida pusley grass was obtained with less than 2.24 kg / ha, for 8 SAT, and, with 4.48 kg / ha,

  a 95% control was obtained for 12 SATs.

  In other tests in greenhouses, the compounds of the present invention exhibited selective control of a large number of annual and perennial weeds.

  in various plants to harvest. As another illustration

  The compound of Example 1 selectively controls the purple sedge of walnuts in both maize and soybeans.

  the respective reports GR15 / GR85 plants to harvest /

  grass (expressed in kg / ha) being 0.67 / 0.25 (F.S. = 2.7) in maize and 1.12 / 0.25 (F.S. = 4.5) in soybeans. The compound of Example 11 showed selective control of yellow sedge

  walnut and quackgrass in corn and soybean

  jas. The respective reports GR15 / GR85 plant to harvest / hide

  walnut rex were> 2.24 / 0.95 (FS = 2.4) in maize and 2.24 / 0.5 (FS = 4.5) in soybeans, and respective ratios GR15 / GR85 for maize and soybeans in the quack grass were> 2.24 / 0.5 (FS => 4.5). In a test against yellow sedge of walnuts in cotton, the GR15 / GR85 ratio (average of two duplicate tests) was 1.96 / 0.95 (F.S. = 2.1). Similarly, the compound of Example 13 showed selective control of yellow sedge of walnuts in cotton and quack grass in wheat, the respective ratios GR15 / GR85 being 0.7 / 0.47 ( FS =

  1.7) in cotton and 0.58 / 0.47 (F.S. = 1.2) in wheat.

  In a test carried out on many plants to be harvested in the greenhouse, the compounds of Examples 1,13,14 and were tested against yellow sedge of walnuts in cotton, soybeans, corn and rice; each compound was-no

  selective in relation to the yellow sedge of walnut trees in rice.

  However, much higher selectivities for yellow sedge of walnuts in cotton, soybean and cane have been shown for each of the compounds in the test; the respective GR15 and GR85 levels for these compounds are shown in Table XII; the selectivity factors are shown in parentheses

after each plant to harvest.

TABLE XII

  The compounds of Examples 1 and 13-15 were further tested against quackgrass in wheat, soybeans and maize; each compound was found to be nonselective in wheat. The selectivity results for the compounds indicated above against quackgrass in soybeans and corn are shown in Table XIII.

TABLE XIII

GR85 GR5

  (kg / ha) (kg / ha) Com-Herb-de Sojas But

posed charlatan.

  Ex.1 0.07 0.8 (11.6) 0.69 (9.9) Ex.13 0.36 1.68 (4.7) 1.68 (4.7) Ex.14 Q, 45 1.46 (3.2) 2.52 (5.6) Ex.15 0.75 1.96 (2.6) 2.24 (3.0)

  In other tests in greenhouses for the effi-

  herbicide, the compounds of Examples 1 and 3 were

GR85 GR15

-

  (kg / ha) _ (kg / ha) Comn- Carex | Cotton Sojas But yellow walnut stems Ex. 1 0.24 1.96 (8.2) 0.87 (3, .6) 0.69 (2.9) Ex.13 0.21 2.52 (12, 0) 1.96 (9.3) 2. 52 (12.0) Ex.14 0.38 2.8 (7.4) 2.24 (5.9) 1.68 (4.4) Ex. 0.44 2.8 (6.4) 1.96 (4.5) 1.96 (4.5) 33.

  tested against a number of annuals, including

  resistant weeds such as Texas

  Panicum, young Johnson grass plants, cane cas-

  health, Alexander's herb, wild prosomillet (panicum milicaeum), red rice and tart. The results of these tests are presented in the table -XIV, the selectivity factors are noted in parentheses; a dash indicates

  marginal or indeterminate selectivity.

at

TABLE XIV

w fli 4- _J% o

r% 3 -

C> 4- Rate Rates

GR1 GR

  (ka / ha) _ (k & ha) Compo- Sojas Texas Young Cane Herb IProso- Fall Red Rice | Grass

  Panicum seedlings of Ale-Imillet panicum pico-

  Johnson's Exotic Wild Herb Xander Johnson Ex.1> 1.12 1.12 0.14 0.28 0.56 1.12 <0.07 0.2 1.12

  (> 1.0) (> 8.0) (> 4.0 (> 2.0) (> 1.0) (> 16.0) (> 5.6) (> 1.0)

  Ex.3> 1.12> 1.12 0.28 0.93> 1.12 1.12 <0.07 0.14> 1.12

  (-) (> 4.0) (1.2) (> 1.0). (-) (> 16.0) (> 8.0) (-)

  35. The results in Table XIV indicate that the

  compound of Example 1 selectively controlled each

  annual grass in the test in soybeans. The compound of Example 3 exhibited a positive selective control against

  all weeds except Texas panicumn,

  wild millet and tickling grass, for the maximum experimental rate of 1.12 kg / ha; a higher rate would have been required to determine the selectivity of the compound among the three weeds not showing selective control for the experimental level.

  A distinct advantage of the herbicide is its ability to

  to operate in a wide range of soil types. As a result, the results are presented in Table XV,

  showing the herbicidal effect of the compound of Example 1 on the herbicide

  beq in soybeans in a large number of soil types, with varying contents of organic matter and various contents of clay. Herbicide treatments were

  by incorporation into the soil, the weeds being

  at 0.95 cm depth, with irrigation by the

  above 0.64 cm. Observations were made approximately three weeks after treatment. Selectivity factors

  are presented in parentheses.

TABLE XV

25. _ __

  Com- Type of soil Mati-Argi- Rate GR GR rate set,% (k ha) gani (ga guaen- Sojas EHerbe% charlatan

Ex.1 silty loam -

  said Ray 1.0 9.6 1.12 0.22 (5.1) Sarpy silty clay 2.3 30.35> 2, 24 0.28 (> 8.0) Muddy clay

said Wabash 4.3 33,00,28 -

  Soil Clay Drummer 6.0 37.0 2.24 0.11 (20.0) Florida Sand 6.8 1.8 1.96 0.2 (9.8) Florida Garbage 60 - > 2.24 0.58 (> 3.9) 36. The results in Table XV show that the compound of Example 1 seems to be quite insensitive to soil types with various levels of organic matter, which exhibit control. selective selection of quack grass in soybeans in soils with organic matter ranging from 1.0% to 60% and a clay content ranging from at least 1.8% to about 37%. The results on soja in the so-called Wabash silty clay were indeterminate in this test. Also, the selectivity factors indicated in silty clays. Sarpy and Drummer and Florida manure (rubbish) are minimum values, since the maximum experimental rate was 2.24 kg / ha and the herbicide was safe in the soybean.

same rate above 2.24 kg / ha.

  Laboratory tests were conducted to determine

  finish herbicide resistance according to this

  invention to soil leaching and herbicidal

  resulting cide. In these tests, the compounds of Examples 1 and 4-6 were formulated in acetone and then sprayed at different concentrations on a weighed amount of loam, loamy said Ray and loamy loam soils called Drummer, contained in pots having a filter paper covering the drainage holes in the bottoms of the pots. The pots containing the treated soil were subjected to leaching by placing them on a rotating table which rotated under two nozzle tips of a water container, calibrated to provide 2.5 cm of water per hour, simulating a fall of rain. The leaching rates were set by varying the time on the rotating teble. The water was delivered to the soil in the pots and allowed to percolate through the filter paper and

  drainage holes. The pots were then left idle for

  3 days at room temperature. The soil treated in the pots was then removed, disintegrated and placed in the form of a surface layer above other pots containing the soils indicated above, seeded with seeds of barnyard grass. The pots were then placed on benches

  greenhouse, irrigated from below and allowed to grow

37.

  to take place for 2-3 weeks. Valuations

  the percentage of growth inhibition, by comparison

  reason with the control pots (untreated), and the weights

  fresh for the barnyard grass were recorded; the re-

  The results for the control represent six tests performed. in duplicate and those for experimental compounds three trials

  made in duplicate; the experimental results are presented

  in Table XVI. The fresh weights of the weed were not measured for soil tests

  loamy loam soils called Drummer.

TABLE XVI

  Barnyard Grass Percentage of Inhabitants Freshly Packed (grams) Compo Rate Rain Terreau li- Terreau! I- Terreau li Terreau

  se (kg / (cm)), which is said to be good

  ha) Ray IDrummer Ray said Drumme] Con- O O 4,371 control 0 1,27 3,88

O 5.08 4.14

o 10.16 3.98 Mo- yen 4.10

Ex.l 2.24 O 100 100 0 -

1.27 100 100 0 -

, 08 95 100 0.20 -

, 16 35 100 2.65 -

0.56 O 100 100 0 -

1.27 100- 100 0

, 08 70 100 1.21 -

, 16 33 100 2.73 -

0.14 O 95 100 0.20

1.27 96 97 0.17 -

, 08.58 95 1.74 -

, 16 20 20 3.26 -

Ex.4 2.24 100 100 -

1.27 100 100 0 -

, 08 100 100 0 -

, 16 95 100 0.22 -

0.56 2 100 100 0

1.27 100 100 0 -

, 08 94 100 0.24 -

, 161 52 100 1.97 -

-15 i 38. 0.14 s Ex.512,24 I. i

I 1 0.56

  0.14 Ex.6 0.24 0.56, 14 TABLE XVI (Continued)

0 99

  1.27, 08, 16 O 1.27, 08, 16 O 1.27, 08, 16 1.27, 08, 16 o 1.27, 08, 16 o 1.27, 08, 16 O 1.27 , G8, 0.05 0.22 1.53 3.15 o0 0.31 1.18 0.02 0.44 3.41 o 0.41 2.77 3.62 0.03 O, 64 0 , 0.02 0.01, 0.11 0.66 0.43 1.72 2, 92 o 0.03 D-, 0.04 0.02 0.01 0.41, 1, 1, 0, 0.66 0, 1.72 2.92 - Referring to the results in Table XVI, it will be seen that the compounds of the present invention were very

  resistant to soil leaching under various conditions

  Rainfall. In particular, for a rate of application

  cation of 2.24 kg / ha, each of the compounds of the present invention controlled backyard grass under the equivalent of 10.16 cm of rainfall in loamy loam soil

  says Ray and in loamy clay loam soil says Drum-

  sea except the compounds of Examples 1 and 5 in the Ray o silt control was maintained under the equivalent of 5.08 cm of rainfall. Even for a low application rate of 0.14 kg / ha, the compounds of Examples 1, 4 and 5 controlled the backyard grass in so-called loamy clay soil.

  Drummer under the equivalent of 5.08 cm of rainfall.

* Toxicological studies on the booster of the exem-

  39, ple 1 indicated that the compound was quite safe. It is slightly toxic (DLO50 = 2.300 mg / kg, DLM50> 5.010 mg / kg) and has mild irritation to the eyes and no irritation to the skin. No special handling procedure beyond normal precautions is considered necessary.

  Accordingly, it will be appreciated from the description of

  previous detailed statement, that the compounds according to

  This invention has shown remarkable herbicidal properties.

  superior and unexpected, both abso-

  solute and compared to the most interesting compounds of the

  structure point of view in the prior art. More by-

  In particular, the compounds of the present invention have been

  revealed remarkably selective herbicides particularly

  for the control of difficult annual and perennial grasses

  ciles to destroy in soybeans and maize, but also in

  peanuts, cotton and other crops.

  More particularly, the compounds according to the present invention

  have a remarkable control or destruction

  perennial weeds, such as

  latan and sedges, and resistant annual grasses such as

  Texas panicum, picot weed, wild prosomillet

  vulture, Alexander's herb, John

  bran and / or red rice while controlling

  also and / or by removing other herbs

  and other perennial weeds less resistant

  The herbicidal compositions of the present invention, including concentrates which 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 additive

  including diluents, extension or dilution products, carriers and conditioning agents,

  to provide compositions in the form of solids parti-

  finely divided cells, granules, pellets,

  versions, dispersions or emulsions. Thus, the active ingredient 40 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 emulsifier

  or any suitable combination of these products.

  The compositions of the present invention, particularly

  liquids and wettable powders, contains

  Preferably, as a conditioning agent, one or more surfactants are present in amounts sufficient to render a given composition readily dispersible.

  in water or in oil. The incorporation of a ten-

  sio-active in the composition greatly enhances their effectiveness.

  ciency. By the term "surfactant" is meant that wetting agents, suspending agent dispersing agents and emulsifying ages are included. Anionic, cationic and nonionic agents

  can be used with equal ease.

  Preferred wetting agents are alkyl-

  benzene and alkylnaphthalenesulfonates, sulfa fatty alcohols

  acids, amines or amines, acid esters

  long-chain sodium isethionate, sulphate esters,

  sodium fosuccinate, sulphated or sulphonated fatty acid esters, petroleum sulphonates, vegetable oils

  sulphonated acetylenic glycols, ditertiary glycols,

  polyoxyethylenic alkylphenols (particularly

  isooctylphenol and nonylphenol) and polyoxy-

  ethylenic esters of monocarboxylic fatty acids

  Hexitol anhydride (eg sorbitan). Preferred dispersion products are methylcellulose, polyvinyl alcohol, sodium lignin sulphonates, polymeric alkylnaphthalenesulfonates, naphthalenesulphonate.

  of sodium and polymethylene bisnaphthalenesulphonate.

  Wettable powders are compositions

  water-persistant, containing one or more active ingredients, an inert solid extender or diluent product and one or more wetting and dispersing agents. Inert solid extension products are usually 41.

  of mineral origin, such as natural clays, earth

  of diatoms and synthetic minerals derived from silica and the like. Examples of such extenders or diluents include kaolinites, attapulgite clay and synthetic magnesium silicate. The wettable powder compositions of the present invention

  usually contain about 0.5 to 60 parts (preferably

  5-20 parts) of active ingredient, about 0.25 to

  parts (preferably 1-15 parts) of wetting agent

  ge, about 0.25 to 25 parts (preferably 1.0-15 parts) of dispersing agent and about 5 to about 95 parts (of

  preferably 5-50 parts) of extender or diluent

  Inert solid composition, all parts being by weight

  relative to the total composition. Where required,

  0.1 to 2.0 parts of the extender or dilu-

  inert solid can be replaced by an inhibitor

  corrosion or an anti-foam agent or both.

  Other formulations include dust concentrates comprising from 0.1 to 60% by weight of the ingredient

  active ingredient, on a product of extension or dilution

  corn; these dusts can be diluted for application at concentrations in the range of about 0.1-10% by weight. Aqueous suspensions or emulsions may be prepared by stirring an aqueous mixture of an ingredient

  active ingredient, insoluble in water, and an emulsifying agent

  until a uniform product is obtained and then

  homogenized to provide a stable particulate emulsion

  the very finely divided. The resulting concentrated aqueous suspension is characterized by its extremely small particle size, so that when it is diluted and

  sprayed, the coating is very uniform. Concentrations

  Suitable formulations of these formulations contain about 0.1-60%, preferably 5-50%, by weight of active ingredient,

  the upper limit being determined by the solu-

  ability of the active ingredient in the solvent.

  In another form of aqueous suspensions, a herbal

  42. Water-immiscible bicide is encapsulated to form a microencapsulated phase dispersed in an aqueous phase.

  an example embodiment, tiny capsules are formulated

  by bringing together an aqueous phase containing an emulsifier consisting of lignin sulphonate and a water immiscible chemical and polyphenyl isocyanate.

  polymethylene, by dispersing the immiscible phase with

  in the aqueous phase, followed by addition of a polyfunctional amine

  tional. The isocyanate and amine compounds react to form a solid urea shell wall around the particles of the water immiscible chemical,

  thus forming microcapsules. Generally, the concentration

  The encapsulated material will range from about 480 to about 700 g / l

  total composition, 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, dimethylsulfoxide, N-methylpyrrolidone, hydrocarbons and ethers, esters or ketones which are immiscible with

  the water. However, other liquid concentrates, concentrating

  tion, can be formulated by dissolving the

  active ingredient in a solvent, then diluting, for example

  with kerosene, up to the spray concentration.

  The concentrate compositions here contain

  typically 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, when this is

  about 4 to 94 parts of solvent are required, all parts

  by weight based on the total weight of the oil

the emulsifiable.

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

  active from the particulate product, a surfactant

  active, as indicated above, may be present

  in the composition. Natural clays, pyrophyllous

  lites, illite and vermiculite are examples of classes

  working well with extension or dilution products half

  particles. The products of extension or dilution

  The preferred pre-formed particles are porous absorbers.

  bantes, such as pre-formed particulate attapulgite

  and sieved, or particulate vermiculite, expanded thermally

  as well as finely divided clays such as

  so-called kaolin, hydrated attapulgite or bentonitic clays. These extension or dilution products are sprayed or mixed with the active ingredient to form

herbicidal granules.

  The granular compositions of the present invention

  tion 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 0 to about 5 parts

  by weight of surfactant per 100 parts by weight

of particulate clay.

  The compositions of the present invention may also contain other additive products, for example, fertilizers, other herbicides, other pesticides, safety products and the like, used as adjuvants or in combination with any of the adjuvants described above. Useful chemicals in combination with the active ingredients of the present invention include, for example, triazines, ureas, carbamates,

  acetamides, acetanilides, uracils, acid derivatives

  - acetic or phenol, thiolcarbamates, triazoles, benzoic acids, nitriles, biphenyl ethers and the like, such as: 44. Heterocyclic nitrogen / sulfur derivatives 2-chloro-4-ethylamino-6-isopropylamino-s-triazine 2-chloro-4,6-bis (isopropylamino) -s-triazine 2-chloro-4,6-bis (ethylamino) -s-triazine 3-isopropyl-1H-2,1,2-dioxide , 3-Benzothiadiazin-4- (3H) -one 3-amino-1,2,4-triazole

  the salt of 6,7-dihydrodipyrido (1,2-a: 21 ', 1' -c) -pyra-

  zidinium 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-dimethylurea 1-butyl-3- (3,4-dichlorophenyl) -1-methylurea Carbamates / thiolcarbamates 2-chloroallyl diethyldithiocarbamate S- (4-chlorobenzyl) N, N-diethylthiolcarbamate N- (3chlorophenyl) ) isopropyl carbamate

  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- [L (trifluoromethyl) sulfonyl] amino] phenyl) acetamide Nisopropyl-2-chloroacetanilide

  2 ', 6'-diethyl-N-methoxymethyl-2-chloroacetaniline

of

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

chloroac etanilide

  1α, α-trifluoro-2,6-dinitro-N, N-dipropyl-p-

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

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

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

  N- (phosphonomethyl) glycine, its monoal-

  alkyl (C1-C6) amine, its alkali metal salts and

their combinations.

  Ethers 2,4-Dichlorophenyl-4-nitrophenyl ether

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

  xy-4-nitrodiphenyl Miscellaneous products 2,6-dichlorobenzonitrile methanearsonate monosodium acid disodium methanearsonate

  Useful fertilizers in combination with the

  active ingredients include, for example, ammonium nitrate,

  urea, potassium carbonate and superphosphates.

  Other 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 several examples.

  illustration realization plots shown below.

  46. I. Emulsifiable Concentrates A. Compound of Example No. 1 Calcium dodecylbenzenesulfonate / polyoxyethylene ethers mixture (for example product known under the trademark Atlox 3437F) Calcium dodecylbenzenesulphonate (product known as FloMo 60H) Aromatic solvent. C9 B. Compound of Example No. 4 Calcium dodecylsulfonate / alkylarylpolyether alcohol mixture Solvent formed from C9C aromatic hydrocarbons. Compound of Example No. 6 Calcium dodecylbenzenesulphonate / polyoxyethylene ether (for example, so-called 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 D. Compound of Example No. 7 Castor oil ethoxylated Product called Rhodamine B Dimethylformamide% by weight, 0 4.85 0.15, 00.00, 0 4.0 11.0, 00.0 1.0 94.0.00% by weight, 0.000.0.0 , 00, 0, 0

-100.00

  , 0, 0 0.5 74.5, 00 47. III. Emulsions% A. Compound of Example No. 12 Block Polymer Polyoxyethylene / Polyoxypropylene with Butanol (for example product known under the tradename Tergitol XH) Water B. Compound of Example No. 13 Block Copolymer Polyoxyethylene / Polyoxypropylene with Butanol Water IV. Wettable Powders by Weight, 4.0-56.0, 00.0 3.5 91.5, 00 s A. Composed of Example No. 1 Sodium Lignosulfonate N-methyl-N-Sodium Oleyltaurate Amorphous Silica (Synthetic) B. Compound of Example No. 12 Sodium Dioctyl Sulfosuccinate Calcium Lignosulfonate Amorphous Silica (Synthetic) C. Compound of Example No. 13 Sodium Lignosulfonate N-methyl-N-sodium N-oleyltaurate Kaolinite Clay V. Dust A. Compound of Example No. 7 Attapulgite B. Compound of Example No. 8 Montmorillonite% by Weight, 0, 3.0 1.0 71.0, 00, 0 1.25 2.75 16.00, 00 10 3, 0 1.0 86.0.00% by weight 2.0 98.0, 00, 0, 0, 00 48. C. Compound of Example No. 9 Bentonite D. Compound of Example No. 10 Diatomaceous earth VI. Screen granules 0.841 mm A. Compound of Example No. 1 - Granular Attapulgite (passing at mesh size between 0.420 mm and 0.420 mm) B. Compound of Example No. 6 Diatomaceous earth (passing through the mesh sieve) between 0.841 mm and 0.420 mm) C. Compound of Example No. 12 Bentonite (passing through sieve with a mesh size of between 0.841 mm and 0.420 mm) D. Compound of Example No. 13 Pyrophyllite (passing through a sieve with opening of meshes between 0.841 mm and 0.420 mm) VII. Microcapsules% by weight, 0.0, 0.00, 0.0, 0.5, 99.5, 00, 0.0, 00 A. in a Reax 88 B product

  Compound of Example No. 1 encapsulated

polyurea envelope wall

Sodium lignosulfonate (e.g.

  known under the trademark Water% by weight 49.2 0.9 49.9, 00, 0, 0, 00 1, 0 99.0, 00 4 9.

  B. Composed of Example 12 euicap-

  embedded image in a polyurea envelope wall Potassium lignosulfonate (for example a product known under the trademark Reax C-21) Water

C. Composed of Example 13 in

  encapsulated in a polyurea shell wall Magnesium salt of lignosulfate, 0.589.5, 00.0 (product known under the tradename Treax, LTM) 2.0 Water 18.0, 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 incor-

  pores in aquatic environments in any manner

  re ok. The application of liquid compositions and

  particulate solids on the ground can be achieved by

  conventional methods, such as mechanical dust-forming devices, telescopic and hand-held spraying devices and spray-dusting devices. The compositions can also be applied also from aircraft in the form

  dust or spray as a result of their

  cacity at low doses. The application of herbal compositions

  aquatic plant bicides is usually achieved by adding the compositions to aquatic environments in the

  o control of aquatic plants is desired.

  Application of an effective amount of the compounds of the present invention to the location of unwanted weeds is essential and critical to the implementation of the present invention.

  in practice of the present invention. The exact amount of

  active ingredient to use depends on a variety of factors, including

  the species of plant and its stage of development, the

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

  specific tanilide used. In a selective application of rr-é6; plant weight control, at a dose of from 0.2 to about 1.2 kg / ha, preferably from about 0.04 to about 6r k / ha, or suitably from 1.12 to 5.6 kg; Acetanic acid is usually used. Lower or higher rates may be exited in some cases. - a person experienced in little technique. easily dezerminate

  from this description, including the examples shown

  below, the optimum rate to apply in any

particular case.

  The term "soil" is used in its broadest sense to include all the classical soils, such as

  determined in the New International Dictionary of Webs-

  ter, second edition, unabridged (1961). Thus, the term

  refers to any substance or environment in which the

  can take root and grow, and includes not only

  soil but also compost, fertilizer, manure

  (garbage), humus, sand and the like adapted for

hold the growth of plants.

  The appreciation of some of the values of measurements

  above must take into account the fact that they

  come from the conversion of Anglo-Saxon units into

metric tees.

  The present invention is not limited to the examples

  ples of achievement which have just been described, it is

  otherwise susceptible to variations and modifications which

will appear to the man of the art.

X.

Claims (20)

  1 - Compounds, characterized in that they have the mule: 0o = C1CH2C \ "CH20R NOT R CF3   R is a C1-C6 alkyl group or a C1-alkoxyalkyl group or an alkenyl group or an alkynyl group having up to 5 carbon atoms and R1 is hydrogen, methyl or ethyl, provided that: -   when R1 is hydrogen, R is the isopropyl group   pyle, and when R1 is the ethyl group, R is the group ethyl, n-propyl or isopropyl.   2 - Compounds according to claim 1, characterized in that   in that R is a C24 alkyl group.   3 - Compounds according to claim 2, characterized   in that R1 is methyl.   4 - Compound according to claim 3, characterized   in that it is formed by N- (ethoxymethyl) -2'-trifluoro-   methyl-5'-methyl-2-chloroacetanilide. - Compound according to claim 3, characterized   in that it is formed by N- (n-propoxymethyl) -2'-trifluoromethyl   rométhyl-6'-methyl-2-chloroacetanilide.   6 - Compound according to claim 3, characterized   in that it is formed by N- (isopropoxymethyl) -2'-trifluoromethyl   rométhyl-6'-methyl-2-chloroacetanilide. 7 - Compound according to claim 3, characterized   in that it is formed by N- (isobutoxymethyl) -2'-trifluoromethyl   rométhyl-6'-methyl-2-chloroacetanilide.   8 - Compounds according to claim 2, characterized   in that R 1 is ethyl.   52. 9 - Compound according to claim 8, characterized   in that it is formed by N- (ethoxymethyl) -2'-trifluoro-   methyl-6'-ethyl-2-chloroacetanilide. - Compound according to claim 8, characterized   in that it is formed by N- (n-propoxymethyl) -2'-trifluoromethyl   rométhyl-6'-ethyl-2-chloroacetanilide. 11 - Compound according to claim 8, characterized   in that it is formed by N- (isopropoxymethyl) -2'-tri-   fluoromethyl-6'-ethyl-2-chloroacetanilide.   12 - Compounds according to claim 2, characterized in that R 1 is hydrogen.   13 - Compound according to claim 12, characterized   in that it is formed by N- (isopropoxymethyl) -2'-tri- fluoromethyl-2-chloroacetanilide.   14 - Compounds according to claim 1, characterized   R 3 is a C 3 -C 5 alkenyl group - A compound according to claim 14, characterized in that   in that it is formed by N- (allyloxymethyl) -2'-trifluoro-   methyl-6'-methyl-2-chloroacetanilide.   16 - Compounds according to claim 1, characterized   in that R is a C35 alkynyl radical.   17 - Compound according to claim 16, characterized   in that it is formed by N- (propargyloxymethyl) -2'-tri-   fluoromethyl-6'-methyl-2-chloroacetanilide. 18 - Compounds according to claim 1, characterized   in that R is an alkoxyalkyl radical of up to 5 atoms my carbon.   19 - Compound according to claim 18, characterized   in that it is formed by N- (2-methoxyethoxymethyl) -2'-   trifluoromethyl-6'-methyl-2-chloroacetanilide.   - Herbicide composition, characterized in that it comprises an adjuvant and a herbicidally effective amount of a compound having the formula: ## STR2 ##   R and R 1 are as defined in claim 1.   21 - Composition according to claim 20, characterized   in so far as the provisions are applied in accordance with   any of claims 2 to 13.   22. The composition according to claim 20, wherein   characterized in that in the compound R is an alkenyl radical;   having up to 5 carbon atoms.   23 - Composition according to claim 22, characterized   characterized in that the compound is N- (allyloxymethyl) -2'-   trifluoromethyl-6'-methyl-2-chloroacetanilide.   24 - Composition according to claim 20, characterized   characterized in that in the compound R is an alkynyl radical;   having up to 5 carbon atoms.   Composition according to Claim 24,   characterized in that the compound is N- (propargyloxymethyl) -2'-   trifluoromethyl-6'-mnéthyl-2-chloroacetanilide.   26 - Composition according to claim 20, characterized   in that in the compound R is an alkoxy radical   alkyl having up to 5 carbon atoms.   27 - Composition according to claim 26, characterized   characterized in that the compound is N- (methoxyethoxymethyl) -   2'-trifluoromethyl-6'-methyl-2-chloroacetanilide.   28 - Method for combating unwanted plants   plants to be harvested, characterized in that   to apply to the place where these plants are found   desirable, a quantity which is effective from the herbicidal point of view   of, a compound having the formula: 54. o I ClCH2C CH2OR R CF3 1Q   or R and R1 are as defined in claim 1.   29 - Method according to claim 28, characterized in that the provisions of any one of Claims 21 to 27.   - Method according to claim 28, characterized in that the plants to be harvested are maize, sorghum, soybeans, cotton, peanuts, white beans, wheat and rapeseed.   31 - Process according to claim 30, characterized   in that the compound is N- (ethoxymethyl) -2'-trifluoromethyl   rométhyl-6'-methyl-2-chloroacetanilide. 2O 32- Method for combating undesirable plants in maize or soybeans or cotton or rapeseed or   brittle beans, characterized in that it consists in applying   place where these plants are to harvest a quantity   herbicide-effective, N- (ethoxymethyl)   thyl) -2'-trifluoromethyl-6'-ethyl-2-chloroactanilide.   thyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide.