DD160268A5 - HERBICIDE COMPOSITIONS - Google Patents

Abstract

The invention relates to a group of N-alkoxymethyl-2-haloacetanilide compounds, herbicidal preparations which contain these compounds as active ingredient, and to processes for using these herbicides in various crops, especially sorghum. The herbicides according to the invention are particularly effective against hard-to-kill ungulates, in particular sorghum halepense seedlings and / or sorghum biocolor, panicum miliaceum, cyperus esculentus and amaranthus retoflexus, as well as setaria lutescens, Echinochloa crus-galli and Digitaria sanguinalis.

Description

The invention relates to herbicidal compositions and their use in agriculture, e.g. as herbicides.

Characteristic of the known technical solutions:

Among the publications related to this invention are numerous descriptions of 2-haloacetanilides which may be unsubstituted or substituted with a variety of substituents on the anilide nitrogen atom or on the anilide ring, e.g. with alkyl, alkoxy, alkoxyalkyl, halogen or other radicals.

The compounds according to the invention which are characterized by an alkoxymethyl or alkenyloxyraethyl radical on the anilide radical, an alkoxy or alkenyloxy radical in an ortho position and hydrogen or a specific alkyl radical in the other ortho position, are, as far as known, most likely to correspond to those of US Pat. Nos. 3/42 and 3,547,620, in particular the compounds 2'-tert-butyl-2-chloro-N-methoxymethyl-6'-methoxyacetanilide and their bromo analogue (compare Examples 18 and 34 in US Pat No. 3,547,620 and Examples 18 and 36 in U.S. Patent 3,442,945).

U.S. Patent Nos. 4,070,389 and 4,152,137 disclose a general molded article comprising compounds of the type described in U.S. Patent Nos. 3,442,915 and 3,547,620. However, the only example compound described which has one alkyl radical in one ortho position and one alkoxy radical in the other ortho position has an alkoxyethyl radical on the anilide nitrogen radical; Links of this type are discussed in detail below.

Other less pertinent publications are BE-PS 810,763 and German Application No. 2 2 402 983; to those described therein compounds include Verbinungen the way they are beach rubbed in U.S. Patents A 070 389 and Λ 152, and are connected by a Alkoxyalkylrad'ilcal nij t 2 or more carbon atoms between the Anilidstickstoffatom and the oxygen atom of the Alkoxyanteils marked. The nearest spezxlischen Darüegungen in Belgian Patent No. 810,763 and German Application \ ^r r. 2/102 983 uind compounds idat a Ethoxyethylradikal on to L] iclrsjtoffatom, a ^"T ethoxy- or Ethoxyradikn"! in one ortho position, and one in the other ortho position, ethyl or isonronyl radicals (see 810-733, compounds TTr., 7, 16, and 18); For example, Compounds Ur. 6, 9 and 17, д ~: e is a T.iethoxyethyl or lethoxypropyl radical on the nitrogen atom, an I.'fcthoxy or ethoxy radical in an ortho position, and a I.Tylrad ikal in the other ortho position nubatituiert.

U.S. Patent 3,442,945, which describes the above-mentioned compounds most closely related in their configuration to the compounds of the present invention, contains some herbicidal data for them, and some data suggest other homologous and analogous compounds listed in their chemical names Structure are less closely related.

Similarly, in the BE-PS 810 763 some data for said compounds Nos. 6 and 9 are listed. Although these most relevant references describe herbicidal activity against a number of weeds, they do not disclose data on any compounds which additionally and / or simultaneously control the difficult-to-control narrow-leaved weeds Sorghum halepense and / or Sorghum bicolor, both of the same genus as sorghum (Andropogon sorghum), as well as controlling other hard-to-kill weeds such as Amaranthus retroflexus and Panicum miliaceum, in addition to less resistant weeds such as yellow foxtail, Echinochloa crus-galli, and Digitaria sanguinalis, while harmless to sorghum. From data of the BE-PS 810 763 it is apparent that compound no. 6 kills sorghum, while no information is given on the effect of compound no. 9 on sorghum. As will be shown below, the compounds of the present invention have superior properties to the known homologous compounds as selective herbicides in sorghum.

Aim of the invention;

The invention relates to herbicides which, in comparison to known compounds, are superior in control of controllable weeds such as sorghum halepense seedlings and / or sorghum bicolor, as well as certain compounds controlling other difficult to kill weeds such as Amaranthus retroflexus and Panicum miliaceum In addition to less resistant weeds such as Setaria lutescens, Echinochloa crus-galli and Digitaria sanguinalis, especially in sorghum cultures.

These and other objects of the invention will become more apparent from the following detailed description.

- 4 Presentation of the essence of the invention:

The invention relates to herbicidally active compounds, herbicidal preparations which contain these compounds as active ingredient, and to processes for using these preparations in certain crops, in particular sorghum.

It has now been found that a selective group of 2-haloacetanilides characterized by specific alkoxymethyl or alkenyloxymethyl radicals on the anilide nitrogen atom, specific alkoxy radicals in an ortho position, and hydrogen or the methyl radical in the other ortho-direction are known compared to the prior art Herbicides, including the closest related homologous compounds, possess unexpectedly superior and superior selective herbicidal properties as sorghum herbicides.

An essential feature of the herbicidal formulations of the present invention is their ability to selectively control the narrow-leaved weeds, Johnsongras and / or Shattercane, which are both species of the same plant genus as sorghum (Andropogon sorghum); in fact, sorghum and shattercane are both sorghum bicolor species. It is therefore extremely difficult to selectively control sorghum Shattercane and Johnsongras seedlings without at the same time damaging sorghum. Some of the compounds of the present invention also control other hard-to-kill weed species such as Amaranthus retroflexus, Cyperus esculentus and / or Panicum miliaceum and all compounds of the invention control other species such as Setaria lutescens, Echinochloa crus-galli, Digitaria sanguinalis and other harmful weeds.

The compounds of the invention are characterized by the formula

in which

R isopropyl, n-butyl, isobutyl, sec-butyl, allyl or

2-methylbutyl,

R _{1 is} methyl, isopropyl, η-butyl or allyl, and R ₂ and R-, are hydrogen or methyl, with the proviso

that

and R., each being methyl when R is n-butyl,

Isobutyl or sec-butyl,

R ₂ and R-. each represents hydrogen when R is isopropyl, isobutyl or sec-butyl, and R _{1 is} isopropyl or n-butyl

represent, and

R _{2 is} hydrogen, R 1 is methyl, when R 2-methyl

butyl or allyl, and R _{1 is} allyl.

Preferred compounds of the invention are the following:

N- (isobutoxymethyl) -2 'methoxy-3''6'-dimethyl-2-chloracet-

anilide,

N- (n-butoxymethyl) -2-methoxy-3 · ^f "β * -dimethyl-2-chloracet-

anilide,

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

acetanilide,

N- (allyloxymethyl) -2 · allyloxy-6'-methyl-2-chloroacetanilide, N- (2-Methylbutoxymethyl) ^{-2'-allyloxy-6-methyl-2-f} chloracet-

anilide,

N- (io-propoxy-ethyl) -2'-isopropoxy-2-chloroacetanilide, N- (isobutoxymethyl) -2'-isopropoxy-2-chloroacetanilide and N- (aek-butoxymethyl) -2'-n-butoxy-2-chloroacetanilide.

The usefulness of the compounds according to the invention as active ingredient in herbicidal preparations and methods of application therefor are described below.

The compounds of the invention can be prepared in various ways. So they can e.g. can be generated on the azomethine path described in the above-mentioned U.S. Patents 3,442,945 and 3,547,620. In this azomethine process, the appropriate primary aniline is reacted with formaldehyde to form the corresponding methylenaniline (substituted phenylazomethine), which is then reacted with a haloacetylating agent such as chloroacetyl chloride or chloroacetyl anhydride. It is then reacted with the appropriate alcohol to give the corresponding N-alkoxymethyl or N-alkenyloxymethyl-2-chloroacetanilide as the final product.

Another method of preparing the compounds of this invention involves N-alkylating the anion of the appropriate secondary 2-haloacetanilide with an alkylating agent under basic conditions.

Ausführungabeispiele;

A modification of this N-alkylation process is described in Example 1 for the preparation of the compounds of the invention. In this modification, the halomethyl alkyl ethers used as starting material in the N-alkylation process are prepared in situ.

example 1

This example describes the use of an N-alkylation process to prepare the compounds of this invention. In this embodiment, the alkylating agent is prepared in situ, making the process efficient, economical and easy.

To a cooled mixture of 9-25 g (0.125 mol) of isobutanol, 1.86 g (0.062 mol) of anhydrous paraformaldehyde and 100 ml of methylene chloride was added 7.56 g (0.062 mol) of acetyl bromide; The mixture was stirred until all paraformaldehyde was dissolved, ie, about 45 minutes. To the mixture was then added 4.55 g (0.02 mol) of 2'-methoxy-3 '"6 ¹ -dimethyl-2-chloroacetanilide and 2.0 g of benzyltriethylammonium chloride in 100 ml of methylene chloride. The mixture was cooled to 15 ^° C. and 50 ml of 50% NaOH were added in one portion and stirred for 5 minutes. The layers were separated, washed with water, dried over MgSO 4 and evaporated with Kugelrohr to give 5 »0 g (79 % yield) yellow liquid, bp 107 ⁰ C at 0.02 mm Hg.

Elemental Analysis: Calculated for C ₁ Z-Hg ₄

C: 61.24 x; H: 7.71; Cl: 11.30; Found: C: 61.24; H: 7.72; Cl: 11:28.

The product was identified as N- (isobutoxymethyl) -2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanilide.

Examples 2 till 8

The corresponding N- (alkoxymethyl) - and N- (alkenyloxymethyl) -2- were added by virtually the same procedure and conditions as described in Example 1, but employing the appropriate secondary anilides and alkylating agents as starting materials in an appropriate amount. haloacetanilides, which are listed in Table I together with certain material properties.

Ex.

connection

Table I

Empirical formula

Cp. C

(from Hg)

EIement

elemental analysis

Calculated

Found

N- (isopropoxymethyl) -2'-isopropoxy-2-chlorace "ti

N- (Isobutoxynethyl) -2'-isopropoxy-2-chloroacetanilide

N- (allyloxymethyl) -2'-allyloxy-6'-ethyl-2-chloroacetanilide

N- (sec-butoxyTnethyl) -2'-n-butyl-2-chloroacetanilide

N- (n-butoxymethyl) -2'-nethoxy-3 ', 6'-dimethyl-1-chloroacetanilide

N- (sec-butoxymethyl) -2'-methoxy-3'-6 ^f -d-ethyl-2-chloroacetanylide

IT- ( 2 -ethyl-3- _butyl- 1, -2-allyl-6'- r , ethyl-2-chloroacetanilide

C ₁₈ H ₂₆ CViO ₃

113 (0.01)

113 (0.03)

116 (0.03)

115

(0.02)

108 (0.1)

116 (0.07)

118 (0.08)

C H Cl

C H Cl

C H Cl

C H Cl

C H Cl

60.10 7.40

11.83

61.24

7.71

11,30

62.03

6.51

11.44

62.28

7.99 10.81

61.24

7.71

11,30

61.24

7.71

11,30

63.61

7.71

10.43

60.38

6.80

11.94

61.23

7.72

11,30

61.98

6.53

11.44

62.18

8.03 10.80

61.15

7.79

11,30

61.13 7.78

11.24

3, 7, / 9 10.44

The secondary anilides used as starting material for preparing the above exemplified compounds are prepared by known methods, for example, by haloacetylating the corresponding primary amine with a haloacetylating agent such as haloacetyl halide or anhydride. Usually, the appropriate concentration of the appropriate primary amine in a solvent such as methylene chloride containing a base, eg 10% NaOH, is dissolved and vigorously stirred while with a solution of the haloacetyl halide, eg chloroacetyl chloride, with external cooling at eg 15 to 25 ⁰ C is mixed. The layers are separated and the organic solvent layer is washed with water, dried and evaporated in vacuo.

Also, the primary amines used to make the secondary anilides can be prepared by known means, e.g. by catalytic reduction of the corresponding suitably substituted nitrobenzene, e.g. 2-alkoxy-G-alkylnitrobenzene, in a solvent such as an alcohol, e.g. Ethanol, and using a platinum oxide catalyst. For 2-alkenyloxy (e.g., allyloxy) -6'-alkyl compounds, chemical reduction using iron and acetic acid may be used.

As already mentioned, the compounds according to the invention proved to be effective herbicides, especially pre-emergence herbicides, although it was also possible to detect postemergence activity. Tables II and III summarize the results of tests conducted to determine the pre-emergence activity of the compounds of this invention. The pre-emergence test was carried out as follows:

Good topsoil was placed in aluminum pans and tapped to 1 to 1.3 cm below the top. On

the earth was given a certain number of seeds or offshoots of various plant species. The soil needed to fill the pans after applying the seeds and cuttings was weighed into a pan. The soil and a known amount of active ingredient applied in the form of a solution or a wettable powder suspension were thoroughly mixed and used to cover the prepared pans. After treatment, the pans were placed on a greenhouse bench where they were initially watered from above with a water amount corresponding to 0.64 cm rainfall. Subsequently, they were watered from below as needed so that sufficient moisture was provided for germination and growth.

About 2 weeks after sowing and treatment, the plants were assessed and the results recorded. These are summarized in Tables II and III. The evaluation of the herbicidal effect was obtained on the basis of a fixed scale based on the damage of each plant species.

The ratings are as follows:

To control rating 0 0 25 1 50 - CVJ 75 3 - 24 - 49 - 74 - 100

The plant species used in a test series, for which the data are summarized in Table II, are marked with letters according to the following legend:

A Canada Thistle Creeping thistle Cirsium arvense В cocklebur Xanthium pensylvanj cum С Velvet] eaf Abutilon theophra sti D Torningglory winch Ipomoea sp. e Lamb s qutir t he s Key ѳ Chenopodium album P smartweed Polygonum яр. G Yellow nutsedge Cyperab esculentum H Quack Grass couch-grass Agropyrum repena I Johnson Grass Sorghum halepense J Downy Brome fluffy treape Bromus tectorum К Barnyardgrasa Echinocblea crus-galli

¹ sl A table II σ D Pflanzenspeziea P G H T J к 11 3 Preemergence test о 3 3 3 3 О 3 3 ѵл 1 о 3 e 3 3 3 О 3 3 Verb, from 11 0 1 3 vj 1 о 3 О 3 3 Ex .: Ir. 5 0 В 1 2 2 1 о о о 3 3 1 11 3 3 1 1 1 2 3 2 о 3 3 5 0 1 1 1 О 1 3 о о 3 J 2 11 3 1 2 2 о CM 3 о о 3 3 VJI 3 О 1 1 о 2 3 3 3 3 3 3 11 - О - - 2 2 3 2 1 3 3 VJI о О о О 3 1 3 1 о 3 3 A 11 3 1 1 2 2 3 3 3 3 3 vj 5 3 1 1 2 О 3 3 2 о 3 3 5 11 vj - 1 2 3 3 3 3 3 3 3 5 3 о 1 2 3 3 3 3 1 3 3 6 11 3 2 о О vj 3 1 2 1 3 3 VJI о 2 о О 2 о 1 2 2 3 3 7 2 2 1 О 8th О о g / ha 2 , 6 2 , 6 2 , 6 2 , 6 2 , 6 2 CM 2 , 6

The compounds were further tested by the above method on the following plant species:

L Soybean soybeans Xanthium pensylva- M Sugrbeet sugar beets nicum N Wheat wheat Polygonum convul- 0 Rice rice vulus P sorghum sorghum Ipomoea sp. B cocklebur Sesbanis exaltata Chenopodium album Q Wild Buckwheat winch Polygonum sp. knotweed Abutilon theophrasti D H! Orningglory Bromus tectorum R Hemp sesbania Panicum spp. e lambsquarters reporting Echinochloa crus-galli P smartweed Digitaria sanguinalis C velvetleaf J Downy brome fluffy S Panj cum species brome K Barnyard gra a s T Crabgrac3

The results are summarized in Table III.

-H-

kp / ha 6 L M table III 0 P в q D R e plant species σ J S к T 5, 12 3 2 3 2 2 2 3 3 3 0 3 3 3 3 1 , 28 1 2 Preemergence test 3 0 1 0 0 2 2 P 0 3 3 з Verb, from O, 06 O 1 2 0 0 0 0 0 0 2 0 ι 2 3 "Be is p. O, 01 O 1 1 0 1 1 0 0 0 3 0 0 3 3 1 O, 6 O 1 N 0 0 0 0 0 - 0 0 0 0 0 1 3 5, 12 1 2 2 3 1 0 2 2 2 3 0 0 3 3 3 3 1, 28 O 1 0 1 0 0 2 2 0 1 0 0 3 3 3 3 O, 06 O O 0 0 0 0 0 1 0 2 3 0 2 3 3 O, 6 O O 0 0 1 0 1 1 1 2 0 0 2 3 3 3 2 5, 12 O 2 0 3 1 0 0 2 1 3 0 0 3 3 3 3 1, 28 O O 2 3 1 0 0 1 1 1 0 0 2 3 3 3 0 06 O O 0 2 0 0 0 0 0 0 3 0 1 3 3 3 0 .G O O 0 1 0 0 1 0 0 0 0 0 1 1 3 3 3 5, 12 2 2 0 3 3 0 2 1 3 2 0 1 3 3 3 3 1, , 28 1 2 3 3 1 0 1 0 1 1 0 0 3 3 3 3 O ₁ , 06 1 2 2 VJ 1 0 0 0 1 1 3 0 3 3 3 O ₁ , 01 O 1 2 1 0 0 0 0 1 1 0 0 1 2 3 3 4 O ₁ , 6 O O 0 0 0 0 0 0 0 1 1 0 0 0 1 3 5: 12 O 2 3 2 1 0 1 1 3 2 1 0 3 3 3 1 , , 28 O 1 2 2 0 0 0 0 1 0 0 0 3 3 3 - O, , 06 O 1 0 1 0 0 0 0 1 1 2 0 3 1 3 _ O , 6 O O 0 0 0 0 0 0 1 0 1 0 0 0 2 - 5 5 12 2 2 0 3 3 2 2 2 3 2 1 1 3 3 3 mm 1 , 28 1 2 2 3 2 1 2 2 3 2 0 0 3 3 3 - O , 06 O 1 0 1 0 0 1 1 1 1 2 0 2 3 3 - O , 01 O 1 0 1 0 0 1 1 2 0 2 0 1 2 3 - 6 O , 6 1 1 0 0 0 0 0 1 1 0 1 0 0 2 3 - 5 12 2 2 2 3 2 1 3 2 3 3 0 1 3 3 3 1 1 2  2 3 1 0 1 1 2 2 0 0 3 3 3 - O , 6 O 2 1 3 0 0 1 0 2 1 3 0 2 3 3 - 5 12 O 1 1 2 1 0 1 1 1 0 2 0 3 3 3 mm 7 1 , 28 O 1 0 1 0 0 0 0 0 0 1 0 3 3 3 - O , 06 O O 3 0 0 0 0 0 1 0 1 0 1 0 3 _ O , 01 O O 1 0 0 0 0 0 0 0 3 0 0 0 0 8th O O O 1 0 0 0 0 0 0 0 3 0 0 0 0 - 2 3 1 0 0 0 0

It has been found that the herbicides of the present invention possess unexpectedly superior properties as sorghum selective preemergence herbicides, particularly for the selective control of hard-to-kill weeds, including one or more of the weeds Sorghum balepens e seedlings, Sorghum bicolor (Shattercane), Amaranthus retroflexus, Cyperus esculentus and Panicum miliaceun, and further problem weeds such as yellow foxtail, Echinochloa crus-galli and Digitaria sanguinalis. Selective control and repression of some of the above-mentioned and other weeds by the herbicides of the present invention has also been found in a number of other crops, including soybeans, wheat, rice and sugar beets, as indicated in Table III. However, the clearly superior herbicidal properties of the compounds of this invention are most evident in the selective control of weeds in sorghum.

To illustrate the unexpectedly superior properties of the compounds of the invention both on an absolute and relative basis, comparative tests were conducted in the greenhouse with:

1) known homologous compounds which are most closely related in their chemical structure to the compounds of the invention, and

2) two other compounds which are not homologs but fall under the known compounds mentioned;

one of them has superior properties as a sorghum herbicide, and both are commercial herbicides. All compounds used in the following comparative tests are generally defined as substituted phenyl-N-hydrocarbyloxyalkyl-2-haloacetanilides. The known compounds used for comparison in the tests are identified in the tables as follows:

A. N- (methoxymethyl) -2 ♦ -methoxy-6 ♦ -tert-butyl-2-chloroacetanilide (Example 18, U.S. Patents 3,442,945 and U.S. Pat

3 547 620)

N- (1: ethoxymethyl) -2'-methoxy-6'-tert-butyl-2-bromoacetanilide (Example 34 of U.S. Patent 3,547,620 and Example

36 of U.S. Patent 3,442,945)

C. N- (I. ethoxyethyl) -2'-raethoxy-6'-methyl-2-chloroacetanilide (Compound Ur. 6 of Belgian Pat. No. 763, also listed in German Application No. 2 402 983).

D. N- (ethoxyethyl) -2'-methoxy-6'-methyl-2-chloroacetanilide (Compound No. 7 of BE-PS 810,763)

E. N- (1-J, "ethoxyprop-2-yl) -2'-methoxy-6'-methyl-chloroacetanilide (Compound No. 9 of BE-PS 810,763)

P. N -O.-ethoxyethyl-1'-ethoxy-6'-methyl-2-chloroacetic anil d

(Compound Ur. 16 of BE-PS 810 763) J. N- (isopropoxyethyl) -2 ♦ -methoxy-6'-methyl-2-chloroacet-

anilide G. N- (ethoxyethyl) -2'-ethoxy-6-methyl-2-chloroacetanilide ^f

(Compound No. 18 of the BE-PS 810 763) H. lI- (isopropyl-2-chloroacetanilide (propachlor)

I. N- (T.lethoxymethyl) -2 ^l -6 '- diethyl-2-chloroacetanilide (Example 5 of said U.S. Patents 3,547,620 and 3,442,945);

general name "alachlor", active ingredient in the commercial herbicide LASSO ^, registered trademark of Monsanto Company.

The compound H above is structurally less similar than the mentioned homologous herbicides of US Patents 3,442,945 and 3,547,620, since an alkoxyalkyl or alkenyloxyalkyl substituent on the nitrogen atom and an alkoxy substituent in an ortho position is absent, it is still in the tests carried out here, since reference is made to them in the cited patents 4,070,389 and 4,152,137, and they are compared to others in these

The compounds cited in patents have demonstrated superior properties as a commercial sorghum herbicide. Likewise, compound I is included in the tests because it is within the patents 3,547,620 and 3,442 and is a commercial herbicide.

In herbicidal pre-emergence tests, the compounds of the invention were tested with the known compounds A bin I for the control of various weeds, with an emphasis on the hard-to-kill, eighth-leafless species predominantly affected by sorghum cultures. The test results are listed below.

In the following discussion of the data, reference will be made to herbicidal application rates represented by "GR., -" and "GRg ₁ -"; these quantities are given in kg / ha, which can be converted into lbs / A by dividing by 1.12. GR.t- defines the maximum amount of herbicide at which crop damage occurs at $ 15 or less, while GRqc is the minimum amount necessary to achieve 85% inhibition of the weeds. The GR ₁ - and CR о с - "narrow be used as T.iaß for the possible performance of commercial products, it being understood that suitable commercial herbicides may exhibit greater or lesser plant injuries within angemesoener limits.

Another indication of the effectiveness of a chemical as a selective herbicide is the "selectivity factor"("SP") for a herbicide in certain crops and weeds. It is a measure of the relative degree of harmlessness to the crop plants or toxicity for weeds, and is expressed as daa ratio GR ^ c / GRgc, ie GR _1, - the quantity f ^"ÜR the crop divided by the GRor- ^ close for the weeds, both!

expresses in kg / ha. In the tables below, the selectivity factors, if used, are given in parentheses after the weeds; "NS" means "nonselective". Insignificant or questionable selectivity is indicated with a dash (-) after the culture. Since crop plant tolerance and weed control are related, a brief discussion of this ratio, expressed as a selectivity factor, is appropriate. In general, it is desirable that the safety factors for the crop, cLh. the herbicide tolerance values are high because, for one reason or another, higher herbicide concentrations are often desired. Conversely, for economic and possibly ecological reasons, the levels for weed control should be small, i.e., the herbicide should have high unit activity. However, small amounts of herbicide may not be sufficient to control certain weeds, and more is needed. The best herbicides therefore are those that control the largest number of weeds with the lowest application rate and. the greatest possible harmlessness for the crop, i. Crop tolerance, offer. The "selectivity factors" (defined above) are thus used to qualify the relationship between crop harmlessness and control of weeds. Purely the selectivity factors in the following tables are: the higher the numerical value, the greater the selectivity of the herbicide for the weed control in a particular culture.

The listed pre-emergence tests include both carpark and field tests. In the greenhouse tests, the herbicide is either applied to the surface after planting seeds or offshoots, or it is incorporated into a particular tight soil that is to be spread as a topcoat over test names in seeded test containers. Both

B'eldtests the herbicide is incorporated into the door (PPI) before planting, that is, it is applied to the earth's surface, then mixed in, then the ICuI are planted out plant seeds.

The surface test procedure used in the greenhouse is carried out as follows:

Containers, e.g. Aluminum pans of about 24x13x7 cm, or plastic pots mjt about 9.5x9,5x8 cm, with drain holes in the bottom, are filled to the edge with Ray Schlufflehmerde, which is then tapped to a height of 1.3 cm below the pot edge. The pots are seeded gut with a plant species to be tested and covered with a 1.3 cm high layer of the test soil. The herbicide is then applied to the earth's surface with a belt sprayer (187 l / ha, 2.11 kgf / cm); on occasion other spray devices, e.g. used a DeViI-bJas sprayer. Each pot is watered from above with 0.64 cm of water, then the pots are placed on garbage tables and watered from below as needed. In another method, the irrigation from above can also be omitted. The evaluation of the herbicidal activity takes place about 3 weeks after the treatment.

The herbicide treatment by incorporation into the soil is carried out in greenhouse tests as follows: Good L'iutter soil is placed in aluminum pans and tapped to 1 to 1.3 cm below the edge. On the earth is given a number of seeds or offshoots of various plant species. The soil needed to completely fill the pans after sowing or planting is weighed into a pan. The soil and a known active compound of a solution or suspension of wettable powder are mixed thoroughly and used to cover the prepared pans. After the treatment, the pans receive an initial irrigation from above, the

- 20 -

0.64 cm of precipitate, then they are watered from below as needed so that adequate moisture is present for germination and growth. The irrigation from above can also be omitted. The assessment takes place about 3 weeks after sowing and treatment.

In the tables below, data for compounds that have been tested in multiple runs represent an average of 0.07 to 2.times.4 kg / ha.

Table IV summarizes herbicidal pre-emergence activity data from a first comparative example in which the relative potency of the compounds of Examples and 5, which are representative compounds of this invention, are correlated to those of relevant known compounds, i. Compounds A, B, D, F and G are compared as selective herbicides against certain weeds commonly associated with sorghum. The tables below show the following abbreviations for the tested weeds: Amnranthus retroflexus (RPW), Sorghum halepense seedlings (SJG), Sorghum bi color (Shattercane) (SC), Panicum miliaceum (7 / PY) and Echinochloa crus-galli (BYG ), Digitaria sanguina? -Ie (LCG) and Setaria lutescens (YFT).

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φ φ

From Table IV it can be seen that with respect to the harmlessness of the culture (indicated by the GR ₁ , amount of sorghum) the compounds according to the invention were extraordinarily superior compared to the known compounds. Compared to the structurally closest related known compounds, ie compounds A and B, of the N-alkoxymethyl-2'-alkoxy-6'-alkyl-2-haloacetanilide configuration, the compounds of the invention tested were at least 8.0 to over 16.0 times less harmful to sorghum than compound B, and from about 4.0 to over 0.0 times less harmful than compound Л. Likewise, the compounds of this invention were 8.0 to more than 16.0 times more harmless to sorghum than the homologous known compounds D, P and G, each of which at about 15% damage at such low rates of less than 0.14 kg / ha Sorghum caused.

With regard to the weed control indicated by the GRqc application rates under each weed, it is noted that all known tested compounds, with the exception of compound A, are either completely nonselective, bcw. indeterminate or scarcely selective to all tested weeds in sorghum. Compared with Compound A, the compounds of the invention etv / a were 4.0 to 8.0 times more effective against sorghum halepenne invertebrates, Digitaria sanguinalis and Echinochloa crun-gallj, and 2.0 to 4.0 times more effective against yellow foxtail. The compound of Example 5 also shows positive selective control of Sorghum bicolor and Cyperus esculentus, as well as scarce selectivity to Amaronthu3 and PanJcum miliaceum, where Compound A did not.

In a further comparative test, the herbicidal precursor was run in conjunction with the compound of Example 1 in comparison with that of compound C, D and J; the data are summarized in Table V.

Q) r -I i-l

ад й о.

:

 ι .с

UY СО

о ·

«1 I 00

о о о о

> • V / Ч / N ^

I i

со

Ο О О О V V ѵ / V

ι ι ехГ

 ^ - ^ Vt- ^

т- τ- г- τ-

· * Л л »t

о о о о

V N / N / \ У

CO со f- * I t τ- 00 C \ J ω Ο O O о

; , со Д

со

CVJ

О О О

.а

, о Ь £

P *

со

Q О * ~ Э -H

0) PQ

From the data of Table V it can be seen that the compound of Example 1 of the invention possessed a significantly higher sorghum harmless factor than the known compounds, i.e., it was at least 8.0 times more harmless. In addition to this high culture factor of harmlessness, the compound of the invention exhibited equal and excellently superior selectivity factors compared to the known compounds over each of the weeds tested. It should be noted that the known compounds C, D and J showed no positive selectivity in the culture of sorghum halepense, and the selectivity of these compounds over the remaining weeds was indeterminate and at best scarce; In each Pail, the low deleterious factors of these compounds make them unsuitable as sorghum herbicides.

Further pre-emergence data from other tests with the compounds of Examples 1-8 are summarized in Table VI.

Table VI shows the amounts of GR, GR and GRg for each compound of the invention in sorghum and the respective weeds; the selectivity factors are in brackets, data from multiple tests represent an average of the number of tests indicated. A free space under a particular weed means that this weed was absent in the test with the particular compound.

Table VI

Connection

Beisp.1 ^a Beisp.2 Beisp.3 Beisp.4 Beisp.5 ° ^C Beisp.6 Beisp.7 ^d Beisp.8

connection

Beisp.1 Beisp.2 Beisp.3 Beisp.4 ^b Beisp.5 ° Beisp.6 £ Beisp.7 ^a Be ^": SP.8

₁₅ (kg / ha)

1.14 7 1.12

> 1.12 0.57

} 2.24 0.7

> 0.7

YUS

> J

> 0.4K 2.8)

0.43 (1.3)

> 2.24 (-)

0.14 (5.0)

0.35 (> 2.0 0.43 (2.7) <0.09 012.7) 0.56 (> 2.0) <0.14 (> S, 0) 0.56 (> 2, 0) 0.28 (> 4.0)

<O, 16 (> 3.6) 0.09 (> 6.4) 0.28 (> 8.0) <O, 12 (> 18.7) 0.15 (5.0) <0.14 (> 5.0)

<0.09 07.8) <0.11 (-6.4) O, 21 (> 5.3) 0.28 (> 4.0)

0.97 (1.18) 0.095 (12.0) "^ 0.22 ^ 5.0)

0.28 (M, 0)

<0.15 (> 3.8) <0.09 (> 6.4)

1.3 (> 1.7) 0.16 (> 14.0

O, 14 (? 5, O) <0.11 (> 6.4)

< 0.07 (> 10.0) <0.09

0.28

YPT

1.0 (1.14) 0.75 (1.52) 0.12 (9.5) 0.16 (> 7.0) 0.46

0.35 (1.6) 0.64 (IiS) 0.09 (6.4)

M, 9 M, 2)> 1.4 M, 6) 0.36 06.2)

0.43 (1.6) 0.21 (3.3) <0.11 (> 6.4)

0.84 (US) 0.21 (> 3.3) <0.09 07.8)

0.28 (> 4.0)

a. Average of 7 passes

b. Average of 5 passes

c. Average of 2 passes

d. Average of 3 passes

Looking at Table VI, it is first apparent that any compound of the invention tested against sorghum halepense and sorghum bi color selectively controlled these two weeds in sorghum at rates of from 0.57 to 2.24 kg / ha; this is a result which, as far as known, has not been achieved by any of the known compounds, nor by the commercial herbicidal compounds H and I - compound H being a leading commercial sorghum herbicide. In addition, with three exceptions, all compounds of the invention showed positive selective control of each weed tested; the three exceptions were lack of positive selectivity of the compound of Example A over Panicum miliaceum, the compound of Веізріеі 7 vs Cyperus esculentus, and scarce selectivity of the compound of Example 5 over Латап-thus.

Since the pre-emergence herbicidal data of Tables IV b ^ s VI were obtained by identical routine methods, d ^; e herbicidal activity of the compounds of the invention of Table VI are also compared with the herbicidal activity of the known compounds in Tables IV and V. Here, too, it is clearly demonstrated that each of he f indungscemüßen compounds all known relevant compounds with regard to harmlessness for the culture invariably excellent superior; the same applies to the selective weed control as indicated by the selectivity factors, with the exception of isolated cases. Of all the known compounds tested, only compound A (Table IV) showed positive selective control of sorghum halepense, digitaria, echinochloa and yellow foxtail in sorghum; Compound A was not selective against the remaining test weeds. In both weeds, which were selectively controlled by compound A, the compounds according to the invention exhibited excellently higher selectivity, with the exception of the

Compounds of Examples 2 and 3 which were comparable to Compound A over Sorghum halepense. In any case, the lower harmlessness factors f ^; -r sorghum and / or the non-selectivity or questionable selectivity of the relevant known compounds against all tested weeds the 3e compounds unsuitable as sorghum herbicides.

V / Le already mentioned, reference is made to compounds H and I in the above-identified patents, and they constitute the active ingredients in commercial herbicides; Pre-H is a widely used sorghum herbicide. Although none of these compounds are homologs, isomers or analogs of the compounds of the present invention, they were similarly tested against the same weeds as the compounds of the present invention, as shown in Tables IV to VI, in comparison to their herbicidal pre-emergence activity to determine the compounds of the invention. It was found (based on the average of 5 repeat tests with compound I and 9 repeat tests with compound H) that none of the compounds selectively controlled sorghum bicolor in sorghum and that compound H had no positive control of sorghum halepense while the compound I showed only limited selectivity, with a selectivity factor of about 1.2 over sorghum halepense. Incidentally, compounds H and I selectively controlled the remaining weeds listed in Tables IV to VI. It is thus evident that the compounds according to the invention have clear advantages even over commercial herbicides in the selective control of weeds in sorghum.

The compounds of the invention possess selective herbicidal activity in a variety of cultures other than sorghum, as indicated in Table III above. In further tests, the compound of Example 5 also proved to be useful.

at a rate of more than 1.12 kg / ha in soybeans, field maize, cotton, cucumbers, beans, peas, tomatoes and peanuts.

Thus, it is apparent from the foregoing detailed description that the compounds of the present invention exhibited unexpectedly and excellently superior herbicidal properties, both in absolute terms and in comparison with the structurally most closely related compounds, other known homologs and analogs, including known commercial products. haloacetanilides. In particular, the compounds of the present invention have demonstrated excellent harmlessness to sorghum crops, as well as excellent selectivity factors, particularly with respect to hard-to-kill weed species such as sorghum halepense seedlings and sorghum bicolor, as well as other problem weeds such as Amaranthus retroflexus, Cyperus esculentus, Panicum miliaceum, Setaria lutescens, Echinochloa crus-galli, Digitaria oanguinalis, etc., as shown in Tables II to VI.

The herbicidal preparations according to the invention, including the concentrates which have to be diluted before use, contain at least one active substance and one adjuvant in liquid or solid form. The preparations are prepared by mixing the active ingredient with an adjuvant which includes diluents, diluents, carriers and conditioning agents so as to form preparations in the form of finely divided solid particles, cranula, pellets, solutions, dispersions or emulsions. Thus, the active ingredient may 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 a suitable combination thereof.

- 29 -

The preparations according to the invention, in particular liquids and wettable powders, preferably contain as conditioning agents one or more surface-active agents in amounts sufficient to make a particular preparation of water or oil easily dispersible. The inclusion of a surface-active agent in the preparations promotes their effectiveness significantly. The term "surfactant" includes wetting agents, dispersants, suspending agents and emulsifying agents. Anionic, cationic and nonionic agents can be used equally.

Preferred wetting agents are alkylbenzene and alkylnaphthalenesulfonates, sulfated fatty acid alcohols, amides or acid amides, long-chain acid esters of sodium isothionate, sodium sulfo-bucinate esters, sulfated or ω-fonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils, ditertiary acetylenic glycols, polyoxyethylene derivatives of alkylphenols (especially isooctylphenol and nonylphenol) and Polyoxyethylene derivatives of higher fatty acid monoesters of hexitol anhydrides (eg sorbitan). Preferred dispersants are methylcellulones, polyvinyl alcohol, sodium lignosulfonates, polymeric alkylnaphthalenesulfonates, sodium adenium sulfonate, and polymethylene biosnaphthalenesulfonate.

Wettable powders are dispersible compositions containing one or more active agents, an inert excipient and one or more wetting and dispersing agents. The inert yield solids are usually of mineral origin, e.g. natural clays, diatomaceous earth and synthetic minerals of silica and the like. Such extenders include kaolinites, ajttapulgittone and synthetic magnesium silicate. The wettable powders according to the invention usually contain about 0.5 to 60 parts (preferably 5 to 20 parts)

- зо -

Active ingredient, about 0.25 to 25 parts (preferably 1 to 15 parts) of wetting agent, about 0.25 to 25 parts (preferably 1.0 to 15 parts) of dispersing agent and 5 to about 95 parts (preferably 5 to 50 parts) of inert stretched solid , wherein all parts are based on the weight of the total preparation. If necessary, about 0.1 bio.sup.2 of inert stretch solids can be replaced by a corrosion or foam inhibitor, or both.

Other formulations contain dust concentrates containing 0.1 to 60% of active ingredient on a suitable diluent; these dusts may be present for application at concentrations of about 0.1 to 10 -.% are diluted.

Aqueous suspensions or emulsions may be prepared by stirring an aqueous mixture of a Wanger insoluble active ingredient and an emulsifying agent until uniform, and then homogenizing to obtain a n + abilic emulsion of very finely divided particles. The resulting concentrated aqueous suspension int is characterized by its extremely small particle size, so that after dilution and spraying, the coating is more uniform. Suitable concentrations of these preparations contain about 0.1 to 60% by weight, preferably 5 to 50% by weight of active compound, the upper limit being determined by the solubility limit of the active substance in the solvent.

In another type of aqueous suspensions, a water-immiscible herbicide is encapsulated, so that a j η an aqueous phase dispersed Mikrokapselpbase formed. In one embodiment, very small capsules are formed by combining an aqueous phase containing a lignosulfonate emulsifier, a water immiscible chemical, and polymethylene polyphenyl isocyanate.

menbringt, dispersing the water-immiscible phase in the aqueous phase and then adding a polyfunctional amine. The isocyanate and amine compounds react to form a solid urea shell around particles of the water-immiscible chemical, thereby causing their environmental microcapsules. In general, the concentration of the encapsulated material is about 4-80 to 700 g / liter, preferably 480 to 600 g / liter of the whole preparation.

Concentrates are usually solutions of active ingredient in non-odorous or partially water-miscible solvents, along with a surfactant. Suitable solvents for the active ingredient according to the invention include i.a. Dimethylformide, dimethylsulfoxide, N-ethylpyrrolidone, hydrocarbons and water immiscible ethers, esters or ketones. However, other strong liquid concentrates may also be obtained by dissolving the active ingredient in a solvent and then diluting, e.g. with kerosene, to be prepared for spray concentration.

The concentrate formulations generally contain from about 0.1 to 95 parts (preferably 5 to 60 parts) of active ingredient, about 0 to 5 parts (preferably 1 to 25 parts) of surfactant and, if necessary, about 4 to 94 parts of solvent; all parts are by weight and based on the total weight of the emulsifiable oil.

Granules are physically stable particulate preparations containing an active ingredient which adheres to or is dispersed in a mixture of inert, finely divided, particulate extender. In order to assist the leaching of the active ingredient from the particles, a surfactant such as those listed above may be present in the preparation. Natural clays, pyrophyllites, illites, and vermiculites are examples of useful types of particulate mineral extender.

convey. Preferred extenders are porous, absorptive, preformed particles, such as preformed and sieved particulate attapulgite or heat expanded particulate vermiculite, and the finely divided clays, such as kaolin clays, hydrogenated attapulgite or bentonite clays. These extenders are sprayed or mixed with the active ingredient to prepare the herbicidal granules.

The granule preparations according to the invention may contain about 0.1 to 30 parts by weight, 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 clay particles.

The preparations according to the invention may also contain other additives, for example fertilizers, other herbicides or pesticides, protective substances and the like, which are used as adjuvants or in combination with one of the abovementioned adjuvants. Chemicals useful in combination with the active compounds of this invention include triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic or phenolic derivatives, thiolcurbamato, Tr ^; azoles, bonze acids, nitriles, biphenyl ethers and the like, as described in R _# :

Ik-'toronycli r: nitrogen / scbwef elderivato

2-Chloro-4-ethylamino-6-isopropylamino-3-triazine 2-Chloro-4, G-bi 3 - (isopropylamino) -s-triazine 2-chloro- /], G-bi s- (ethylamino) -s triazine

3-Ii3-propyl-1H-2,1,3-benzothiadiazine-4- (3H) -one-2,2-di oxide

3-amino-1,2,4-triazole

6,7-Dihydrodipyrido- (1,2-a: 2 ', 1'-c) -pyrazidiiniumsalz

5-Bromo-3-isopropyl-6-methyluracil 1,1'-dimethyl-4,4'-bipyridinium

- 33 Harnesses

N ¹ - (4-chlorophenoxy) -phenyl-N, N-dimethylurea

TI, N-Dlmothyl-N '- (3-chloro-4-methylphenyl) urea

3- (3, A -dichlorophenyl) -1,1-dimethylurea 1,3-dimethyl-3- (2-benzothiazolyl) -urea 3- (p -chlorophenyl) -1, i-dimethylurea 1-butyl-3- ( 3 , 4-dichlorophenyl) -1-methylurea

Carbamate / biol carbamate

P-Chlorallyldiethyldithiocarbamat S- (4-Chlorben? _J yl) -N, N-diethylthiolcarbamate Isopropyl N- (3-chlorophenyl) carbamate S-2, 3-dichloroallyl-LI, LT-diisopropylthiolcarbamat ethyl li.N-dipropylthiolcarbamat S-Propyldipropylthiolcarbamat

AcetamJde / AcetanJlide / Aniline / amides

?-Chloro-N, N-dia3lylacetamid

H, II-dimethyl-2,2-diphenylacetainid

IJ- (2,4-dimethyl-5 - / 3-trifluoromethyl) -sulfonyl-7-amine

phenyl) -acetamide

lI-isopxopyl-2-chloroacetanilide 2 ', 6'-diethyl-TJ-raethoxymethyl-2-chloroacetanilide

2'-r.lethyl-6'-ethyl-li- (2-methoxyprop-2-yl) -2-chloroacetanilide at, <* - ι <* * -Trifluor-2,6-dinitro-N, N-dipropyl -p-toluidJn

N- (1,1-Dimethylpropynyl) -3i5-dichlorobenzamide

Acids / esters / alcohols

2,2-dichloropropionic acid 2-methyl-4-chlorophenoxyacetic acid 2,4-dichlorophenoxyacetic acid

Methyl-2 - / '~ 4- (2,4-dichlorophenoxy) -phenox ^ J-propionate

3-Amino-2,5-dichlorobenzoic acid 2-riethoxy-3,6-dichlorobenzoic acid 2,3j6-tr'chloropbenylacetic acid ϊΙ-1-naphthylphthalamic acid

IIati'iiHn-5- / ~ 2-chloro-4- (trifluoromethyl) -phenoxy_7-2-nitroben

4,6-di-nitro-o-sec-butylphenol

N- (phosphonomethyl) glycine and its C._g monoalkylamine

and alkali metal salts and combinations thereof

ether

2, A -Dichlorphenyl-4-nitrophenyleth.er

2-Chloro-O ¹ -, Oi>& * -trifluoro-p-tolyl-ethoxy-nitrodiphenyl

ether

Verschiedenee

2,6-Dichlorobenzonitrile r ^T ononatri umsäuremethanarsonat disodium methanarsonate

Fertilizers useful in combination with the active ingredients are S.B. Ammonium nitrate, urea, potash and superphosphate. Other useful additives are i.a. Substances in which plant organisms are rooted and grow, e.g. Compost,! "Is humua, sand and the like.

Pure herbicidal preparations of the type described above are given below as examples of various embodiments.

I. Emulsifiable concentrates

Weight ί

A. Compound of Example No. 1 50.0

Calcium dodecylbenzenesulfonate / polyoxyetbylene ether mixture

(e.g., Atlox® 3437P and Atlox 3438P 5.0

Monochlorobenzene 45.0

B. Compound of Example No. 2

Calciumdodecylsulfonat / alkylaryl polyglycol

ether alcohol mixture

Cq aromatic hydrocarbon Lb '

oungamittel

O. Compound of Example No. 3

Calcium dodecylbenzenesulfonate / polyoxyethylene

ethylene-ether mixture (e.g., Atlox 3437P) xylene

100.0

TI. Liquid Concentrates Gev / - fS

A. Compound of Example No. 4 xylene

B. Compound of Example No. 5 dimethylsulfoxide

100.0

100 , 0 85 , 0 4 , 0 11 , 0 100 , 0 5 , 0 1 , 0 94

10 , 0 90 > o 100 0 85 0 0

Weight Й

C. Compound of Example No. 6 50.0 N -! Iethylpyrrolidone 50 »0

100.0

D. Compound of Example No. 7 5 »0 Ethoxylated castor oil 20.0 Uhodami η Β 0.5 Dimethylformamide 74.5

100.0

III. emulsions

A. Compound of Example No. 8

Polyoxyethylene / polyoxypropylene block copolymer with butanol (e.g., Tergitof.XII) Y / aaser

B. Compound of Example No. 1 Polyoxyethylene / polyoxypropylene bl block copolymer with butanol Water

100.0

IV. Wettable powders

A. Compound of Example No. 3 IT sodium lauryl sulfonate Sodium N-methyl-N-oleyl taurate Amorphous silica (synthetic)

100.0

Ge ν / , 0 40 , 0 A »° 56 , 0 100 , 0 5 , 5 3 , 5 91

25 , 0 3 , 0 1 , 0 71

Weight -5

80 , 0 1 25 2 75 16 00 100 00 10 , 0 3 , 0 1 , 0 86 "о

B. Compound of Example No. Sodium dioctylsulfosuccinate Ca iumligno sulfonate Amorphous Silica (Synthetic)

C. Compound of Example No. Sodium ligno-sulfonate Sodium N-methyl-N-oleyl taurate Kaolinite clay

100.0

V. dusts

A. Compound of Example No. 3 2.0

Attapulgite 98.0

100.0

IJ. Compound of Example No. 4 CO, 0

! .lontmorilloni ^ ^

100.0

C. Compound of Example No. 5 30.0 Bentonite 70.0

1oC, 0

D. Compound of Example No. 6 1.0 diatomaceous earth 99> 0

100.0

Wt .- ^

15 , 0 85 "о 100 , 0 зо , 0 70 _? O 100 , 0 0 , 5 ?? , 5 100 , 0 5 , 0 95

- 38 -

VI. Granule

A. Compound of Example No. 7

Granulated attapulgite (20/40 sieve)

B. Compound of Example No. 8 Diatomaceous earth (20/40)

C. Compound of Example No. 1 Benton.it (20/40)

D. Compound of Example No. 2 PyrophyUit (20/40)

100.0

VIT. T'ikrokapaeln

A. Compound of Example No. 4

umkapaelt ϊη polyurea shell 49.2

liatrum ignumaulfat (e.g., Reax 88®B) 0.9

Wasyan Ί °, °

100.0

R. Compound of Example No. 5

encapsulated in polyurea shell 10.0

Potassium lauroalfonate (e.g., Reax ^ C-21) 0.5

Was he 8 ?, 5

100.0

C. Compound of Example No. 6

encapsulated in polyurea shell 80.0

T.! Agneniumsalz of lignosulfate

(Troax ^ LTM) 2.0

Water 18.0

100.0

-

When used according to the invention, effective amounts of the acetanilides according to the invention are applied to the soil containing the plants or are taken up in a suitable manner in ve / sweet I.edLen. The application of the preparations as liquids and solid particles to the soil can be carried out by conventional methods, for example with Motorzerotüubern, tank and hand sprayers or Sprühzerstäubern. Because of their effectiveness in low doses, the preparations can also be spread from airplanes as dust or spray. The application of herbicidal preparations to aquatic plants is usually carried out by adding the preparations to the aqueous medium in the area in which control of the aquatic plants is desired.

The application of an effective amount of the preparations according to the invention at the site of the unwanted weeds is v / eentlich and critical for the application of the invention. The exact amount of active agent to be used depends on various factors, e.g. the type of plant and its stage of development, the type and condition of the soil, the amount of rainfall and the specific acetanilide used. With selective pre-emergence application to plants or soil, an application rate of 0.02 to 11.2 kg / ha, preferably from about 0.04 to 5.60 kg / ha, or 1.12 to 5.6 kg / ha is usually used Acetanilide used. In some cases, larger or smaller quantities may be needed. The person skilled in the art can easily determine the optimal, in each case, case of the description, including the examples.

The term "soil" is used in the broadest sense of the word and includes all common soil types as defined under "soils" in Webster's New International Dictionary, Socond Edition, 19B1. The term thus refers to any substance or medium in which plants can rooted and grow, and not only closes soil, but also compost, manure, manure,

Humus, sand and the like, which can sustain plant growth.

- а -

Claims (14)

IS, ¹¹ , g, claim; 1. herbicidal preparations, characterized in that
she an adjuvant and a herbicidal v / effective!.! close
a compound of formula I 0 ClCH ₂ C R. CH ₂ OR (D contain, in which R isopropyl, η-butyl, isobutyl, sec-butyl, allyl
or 2-T,! ethylbutyl, R _{1 is} methyl, isopropyl, ©.-Butyl or allyl, and R ₂ and R ~ are hydrogen or methyl, with the
I'ass giving that R ₁ , Ro and R-. each methyl when R is n-butyl, isobutyl or sec-butyl;
R ₂ and R _{1 are} each hydrogen when R is isopropyl, isobutyl or sec-butyl, and R _{1 is} isopropyl or η-butyl; and R _{0 is} hydrogen and R ^. Methyl, when R
2-Ik'ethylbutyl or allyl, and R _{1 is} allyl. Preparation according to item 1, characterized in that the compound of formula I is ¥ - (isobutoxymethyl) -2'-metboxy-3 ', 6'-dimethyl-2-chloroacetanilide. 3. Preparation according to item 1, characterized in that the compound of formula I is N- (n-butoxyethyl) -2'-inethcocy-3 ¹ , 6'-di-methyl-2-chloroacetanilide. 4. Preparation according to item 1, characterized in that the compound of formula I is N- (sec-butoxymethyl) -2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanilide. 5. Preparation according to item 1, characterized in that the compound of formula I is N- (allyloxymethyl) -2'- a3-hydroxy-6'-methyl-2-chloroacetanilide. 6. Preparation according to item 1, characterized in that the compound of formula I is N- (2-metbylbutoxymethyl) -2-allyloxy-6'-methyl-2-chloroacetanilide. 7. A preparation according to item 1, characterized in that the compound of formula I is N- (isopropoxymethyl) -2 · - iaopropoxy-2-chloroacetanilide. 8. A preparation according to item 1, characterized in that the compound of formula I is N- (isobutoxymethyl) -2 · isopropoxy-2-chloroacetanilide. 9. Preparation according to item 1, characterized in that the compound of formula I is N- (sec-butoxymethyl) -2'-n-butoxy-2-chloroacetanilide. 10. A method for controlling undesirable plants in sorghum, characterized in that a herbicidally effective amount of a compound of formula I is applied to the location of these plants. 11. The method according to item 10, characterized in that the compound of formula I 1T- (isobutoxymethyl) -2'-methoxy-3 ', б'-dimethyl-2-chloroacetanilide. 12. The method according to item 10, characterized in that the compound of formula I is N- (n-butoxymethyl) -2'-tnetboxy-3 ', 6 · dimethyl-2-chloroacetanilide. Process according to item 10, characterized in that the compound of formula I is N- (sec-butoxymethyl) -2'-methoxy-3 ', 6'-dimethyl-2-chloroacetanilide. 1-1. Process according to item 10, characterized in that the compound of formula I is N- (allyloxymethyl) -2'-a]] ω-oxy-6'-methyl-2-chloroacetanilide. 15 · The method of item 10, characterized in that the compound of formula I, W- (2-T ^T ethylbutoxymethyl.) - '-аПуіоху-6' -methyl-2-chloroacetanilide 2. 16. The method according to item 10, characterized in that the compound of the formula I is N- (isopropoxymethyl) -2'-isopropoxy-2-chloroacetanilide. 17. The method of item 10, characterized in that the compound of formula I, N- (isobutoxymethyl) -2 ^f ii.iopropoxy-2-chloroacetanilide. 10. The method according to item 10, characterized in that the compound of formula I is N- (sec-butoxymethyl) -2'-n-butoxy-2-chloroacetanilide.