DD157295A5 - PREPARATION HERBICIDE - Google Patents

Abstract

The invention relates to a group of N-hydrocarbylox-methyl-2-haloacetanilide compounds, herbicidal preparations which contain these compounds as active ingredient, and to methods of using these herbicides in various crops, in particular maize and soybeans, but also other crops such as e.g. Cotton, peanuts, oilseed rape, bush beans, wheat and sorghum. The herbicides of the present invention are particularly effective against heavy-killers of several years old such as Wheatgrass and Cyperaceae, but are also effective against annual weeds.

Description

description Field of application of the invention

The invention relates to 2-haloacetanilides and their use in agriculture, e.g. as herbicides.

Characteristics of 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 and / or on the anilide ring, for example with alkyl groups. Alkoxy, alkoxyalkyl, haloalkyl, halogen or other radicals.

The compounds of the present invention characterized by a hydrocarbyloxymethyl radical at the anilide nitrogen, a trifluoromethyl radical at an ortho position, and a methyl radical or, in specific cases, an ethyl radical or hydrogen in the other ortho position, are most likely to correspond, as far as known those of BE PS 810 76 3. The most relevant descriptions in this specification are the general descriptions of N-alkoxyethyl or alkyl-substituted alkoxyethyl-2-chloroacetanilides which may be substituted on the anilide ring in the ortho and meta positions with one or more radicals selected from a variety of radicals, including halogen, alkyl, alkoxy or trifluoromethyl (-CF ₃ ). The list of connections

Table II contains compounds substituted in one ortho position with a -CF ₃ radical and having no substituent in the other ortho position (Compound Nos. 37 to 48); furthermore compounds which are -CF_-substituted in one meta position, while one ortho position is unsubstituted, and the other ortho position with a methbxy radical (compounds Nos. 22 to 25) or a chlorine atom (compounds Nos. 33 to 36) is substituted. However, there is no specific description or exemplary compound for 2-haloacetanilides in BE PS 810,763 which, like the compounds according to the invention, has a -CF "radical in an ortho position and a methyl or ethyl radical in the other ortho position. Moreover, the compounds of BE. PS 810 76 3 is characterized by an alkoxyalkyl group substituted on the anilide nitrogen atom in which the alkylene moiety must have at least 2 carbon atoms between the nitrogen atom and the oxygen atom of the alkoxy moiety. In contrast, the compounds of the invention are further characterized in part by the substitution of an alkoxymethyl radical on the anilide nitrogen atom. The significance of this distinction between the compounds of BE PS 810,763 and the compounds of the present invention will become apparent when considering the comparative data for herbicidal activity, which is clearly the superiority of the compounds of this invention in terms of unit activity, selectivity, weed control -

I 228415 7

prove the correctness and harmlessness of crops. '

Other, less relevant, relevant publications than the aforementioned BE PS 810,763 include U.S. Patents 3,966,811 and 4,152,137, German Application 2 402,983, British Application No. 2,013,188 and ZA-PS 74/0767 , Although these references contain general descriptions of 2-haloacetanilides which, among other substituents, may also have "CF ₃ substitution on the anilide ring, the only descriptions of such types of compounds are found in US Pat. No. 3,966,811 and ZA-PS 74/0767 However, neither of these two patents contains, in general or in particular, ortho-CF 2 -substituted compounds which would be further substituted in the other ortho position with a methyl or ethyl radical; the only -CF 2 -substituted compounds described in these patents Compounds are meta-CF 2 -substituted compounds Further, in both patents, as in the above-mentioned BE PS 810 76 3, it is required that at least 2 carbon atoms be present between the ani? 'Lidtetickstoff and the oxygen of the present ^{Alkoxyanteils;.} ·, Are a condition that is required in all of the above references, with the exception of US Patent No. 4,152,137, in the 1Γ irhaupt no -CF ~ -substituted compounds described "'". ·; rden. '·

-ιχί

- yi -

Of the relevant publications listed above, only BE PS 810,763 and ZA-PS 74/0767 contain data for the herbicidal activity of N-alkoxyalkyl-2-haloacetanilides with -CF ^ substitution on the anilide ring. However, this information is vague, inaccurate and incomplete. Thus, e.g. the BE PS 810 76 3 limited herbicidal data for only a -CF ^ -substituted compound, namely Compound No. (which is the same compound as in Example 2), i. 2-trifluoromethyl-N- (2'-methoxyethyl) -2-chloroacetanilide. In Table III of BE PS 810,763, Compound No. 37 is shown to kill or seriously injure certain unidentified species of "Cuperus", Setaria, Digitaria and Echinochloa, with little damage to the weeds Avena fatua and an unidentified Lolium species certain cultures. Since a precise identification of 5 out of the 6 weeds tested is missing, it is not possible to reasonably evaluate the herbicidal activity of compound 3 7.

Audi ZA-PS 74/0767 contains only limited herbicidal data for only a -CF "-substituted compound, Compound No. 78, i. 2,6-dimethyl-3-trifluoromethyl-N- (2'-methoxyethyl) -N-2-chloroacetanilide. The only herbicidal data for this compound are found in Example 5, where it is reported to show very high growth inhibition in 4 species of weeds. However, no laboratory or field test data on the effect of Compound No. 7 8 in one culture are reported Also, do not talk about whether this connection is a

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shows selective control of a weed in a crop, making it impossible to make a meaningful assessment of this compound. While the above-cited references describe herbicidal activity against a variety of weeds, they do not provide data for -CF ₃ -SUbStX-substituted N-alkoxyalky! Compounds that additionally and / or simultaneously kill perennials that are difficult to kill in one or more cultures Control or suppress weeds, such as couch grass, yellow or purple weevils (Cyperaceae), and a wide range of annual weeds, including annual hardy grasses such as Sorghum halepense seedlings, Sorghum bicolor, Brachiaria plantaginea, Panicum species (Texanum and miliaceum) _. Oryza sativa and Rottboellia exaltata, while also controlling or repressing other harmful annual and annual weeds, such as autumn panicum, polygonum sp., Chenopodium album, amaranthus, fox tails (eg Setaria faberi and lutescens), Digitaria sanguinalis, Echinochloa .. crus- galli, ipomoea sp., abutilon theophrasti, xanthium pensylvanicum, portulac, sesbania exaltata, sida spinosa, etc.

The most useful and desirable feature of herbicides is the ability to control weeds over a longer period of time, the better during each growing season. With many known herbicides

L - ν * -

will be sufficient weed control, only for. 2 to 3 weeks, in some very good cases maybe up to 4 to 6 weeks before the chemical loses its phytotoxic activity. A disadvantage of most known herbicides is their relatively short lifetime in the soil.

Another disadvantage of some known herbicides, to some extent related to the life of the soil under normal weather conditions, is the lack of persistence of weed control in heavy rainfall which inactivates many herbicides.

Another disadvantage of many known herbicides is the limitation of their applicability to certain types of soils, that is, while some herbicides are effective in soils of low organic content, they are ineffective in high organic content soils, or vice versa. It is therefore of advantage if a herbicide is useful in all soil types from slightly organic soils to heavy clays and peat.

Yet another disadvantage of many known herbicides is the limitation to a particularly effective mode of application, i. Application to the surface before emergence or incorporation into the soil, application before and / or after planting. The ability to apply a herbicide by any means, by application to the surface or

.J. 228415

Getting into the ground is very desirable.

Finally, a disadvantage of some herbicides is the need to make special arrangements for their handling due to their toxicity. A herbicide should therefore also be safe to handle.

Object of the invention

The invention therefore relates to a group of herbicidal compounds which avoid the abovementioned disadvantages of known herbicides and offer a multiplicity of advantages which have hitherto not been combined in a single group of herbicides.

Explanation of the essence of the invention

The invention provides herbicides that control and / or suppress hard-to-kill perennial and annual weeds as described above while being harmless to a variety of crops, especially for whales and soybeans, but others, including cotton. Peanuts, rape, bush beans, wheat and / or sorghum.

The invention also has as its object to obtain the herbicidal activity in the soil for periods up to 12 weeks.

The invention also relates to herbicides which are resistant to leaching or dilution at high humidity, e.g. strong

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Rainfalls, are consistent.

Furthermore, the invention relates to herbicides that are effective in a wide range of soils, from light to medium organic soils to heavy clays or peat. '·

Another advantage of the herbicides of the invention is a flexible application, e.g. by application to the surface before emergence or by incorporation into the soil. Finally, the herbicides of the invention have the advantage that they are safe and do not require special handling precautions. From the. The following detailed descriptions will further illustrate these and other objects of the invention.

The invention relates to herbicidally active compounds, to herbicidal preparations which contain these compounds as active ingredients, and to processes for using these herbicidal preparations in specific crops.

It has now been found that a selective group of 2-haloacetanilides formed by specific combinations of specific hydrocarbyloxymethyl radicals on the anilide nitrogen atom, a trifluoromethyl radical (-CF) in an ortho position, and a methyl or ethyl radical or hydrogen atom in the other ortho position marked

J. 22841.5

, have unexpectedly superior and outstanding herbicidal properties compared to known herbicides, including closely related and known homologous compounds.

An essential feature of the herbicidal formulations of the present invention is their ability to control a broad spectrum of weeds. These include

Herbs that can be controlled by conventional herbicides, and in addition a variety of weeds that individually or collectively so far escaped the control of a single class of known herbicides. At the same time, they are harmless to crops of one or more crops, including in particular corn and soybeans, but others such as cotton, peanuts, rapeseed, sorghum, wheat and bush beans. While the known herbicides to control a variety of weeds and occasionally) certain resistant weeds are useful, the unique herbicides according to the invention proved capable of a variety of resistant perennial and annual: to control weeds or largely push back, the perennial weeds couch grass, yellow and purple weevils (Cyperaceae), annual broad-leaved weeds such as Sida spinosa, Sesbania exaltata, Polygonum sp., Chenopodium album, Amaranthus, and annual grasses such as Sorghum halepense seedlings, Sorghum bicolor, Brachiaria plantaginea, Panicum te'xanum, Panicum ' miliaceum, Oryza sativa,

Rottboellia exaltata, as well as other harmful weeds such as autumn panicum, foxtails, Echinochloa crus-galli, Digitaria sanguinalis, etc. Improved weed stock reduction has also been achieved in resistant weeds such as Ambrosiaceae, Abutilon theophrasti, Ipomoea sp., Xanthium pensylvanicumj Portulac, etc.

The compounds of the invention are represented by the formula

wherein R is C 1 -C 4 alkyl or alkoxyalkyl or alkenyl or alkynyl of up to 5 carbon atoms, and R is hydrogen, methyl or ethyl; with the proviso that

when R is hydrogen, R is isopropyl, and when R 1 is ethyl, R is ethyl, n-propyl or isopropyl.

Preferred compounds of the invention are those in which R. in the above formula is methyl or ethyl and R is a C _2-4 alkyl radical. Individual preferred compounds of the invention "are the following:

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

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

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

N-cisobutoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide,

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

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

N- (isopropoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide.

Further compounds according to the invention are described below.

 \

The usefulness of the compounds of the invention as active ingredients in the herbicidal preparations prepared therewith, as well as the method of use are described below.

O'i o. Fiction, compounds according to the invention, as described in Example 1, ^ prepared by N-alkylation of the anion of the appropriate secondary 2-Halogenacetanilids with an alkylating agent under basic conditions. A modification of the N-alkylation process is seen in situ

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Preparation of Halogenmethylalkylethern used as starting materials in said N-alkylation process; it is described in Example 2 for the preparation of a further type of compounds according to the invention. · Design examples

 example 1

This example describes the preparation of N- (ethoxymethyl) -2'-trifluoromethyl 1-6'-ethyl-2-chloroacetanilide '.

4.02 g (0.016 mol) of 2'-trifluoromethyl-1-6'-methyl-2-chloroacetanilide, 3.02 g (0.032 mol) of chloromethyl ethyl ether and 2.0 g of benzyltriethylammonium bromide (phase transfer catalyst) were dissolved in 75 ml of methylene chloride in a 500 ml flask mixed with round bottom equipped with mechanical stirrer and thermometer. 15 ml of 50% sodium hydroxide was added with vigorous stirring all at once, resulting in exothermic evolution up to 26C. After about 5 minutes, gas chromatography revealed that the reaction was complete. After 15 minutes, ice and water were added, the layers separated, and the organic layer washed with 2.5% sodium chloride, dried, filtered, and stripped. The dark residue was Kugelrohr distilled, and 3.4 g of a yellow oil fraction, bp. 110-115 ⁰ C at 0.1 mm Hg, were collected. This fraction was taken up in cyclohexane and purified by HPL chromatography, with 20% pure

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Ethyl acetate was used in cyclohexane .Other Kugelrohr distillation of peak fraction gave 3, 2 g (65% yield) of colorless oil, b.p. 100-110 ⁰ C at 0.1 mm Hg. on standing crystallized a white solid, mp. 41-43 ⁰ C, from.

Elemental analysis for C ₁₃ H ₁₅ ClF ₃ NO ₂ (%): Calculated: C: 50.41; H: 4.88; N: 4.52; y Found: C: 50.02; H: 4.81; N: 4.38.

Example 2 _;

This example describes the use of an improved alternative method by which the compounds of the invention can be prepared. A peculiarity of this process is the in situ production of the alkylating agent, making the process more effective, economical and easier.

A slurry of 7.3 g (0.09-6 mole) of ethylene glycol monomethyl ether and 1.44 g (0.048 mole) of paraformaldehyde in 100 mL of methylene chloride solvent was poured into an ice-water bath. Kv.'vlt and 5.9 g (0.048 mol) of acetyl bromide were added. Stirring for 45 min, 4.0 g (0.016 mol) of 2'-trifluoromethyl-6'-methyl-2-chloroacetanilide and 2.0 g of benzyltriethyl

ü "

• ammonium chloride added. Subsequently, 50 ml of 50% NaOH were added all at once. Gas chromatography revealed that the reaction was complete after about 5 minutes. To the mixture

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the ice and water to effect phase separation, the organic phase was then separated, dried, filtered off and stripped. The residue was distilled in vacuo to give 4.2 g (7, 7% yield) of a clear colorless oil, bp. 150-160 ⁰ C at 0.05 mm Hg

Elemental analysis for C ₁₄ H ₁₇ ClF ₃ NO ₃ (I): Calculated: C: 49.49; H: 5.04; N: 4,12; Found: C: 49.33; H: 5.04; N: 4.08.

The product was identified as N- (2-methoxyethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide.

If the N-alkylation process is allowed to develop too high or too low temperatures, then various impurities may be formed, e.g. sec-anilide, the corresponding imidate, α-alkoxyamide or diketopiperazine. Such impurities can be removed by washing the organic layer with a dilute aqueous hydrochloric acid solution, e.g. 2-3% NaCl or 5% HCl.

Examples 3 to 13

Practically the same procedures described under Example 1 or 2, amounts of reactants and general conditions were used, but the appropriate secondary starting anilides and alkylating agents were used to prepare the final product, namely other inventive compositions.

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to prepare suitable compounds of the above formula; these compounds are listed in Table I.

Table I

Ex

 No.

connection

Empirical formula

N- (isopropoxymethyl) -2'-trir '* C ₁ . fluoromethyl-2-chloroacetanilide

N- (n-propoxymethyl) -2'-tri- C _1-1 fluoromethyl-6'-methyl-2-chloroacetanilide

N- (isopropoxymethyl) -2'-tri- C ₁₁ fluoromethyl-6'-methyl-2-chloroacetanilide

N- (isobutoxymethyl) -2'-tri- C ₁₅ I -fluoromethyl-6 '-methy 1, 2-chloroacetanilide

N- (methoxymethyl) -2'-trifluoro-C ₁ , ormethyl-6'-methyl-2-chloro. 'acetanilide

N- (n-butoxymethyl) -2'-tri- C ₁ ,

fluoromethyl-6 ^J -methy1-2-chloroacetanilide

N- (sec-butoxymethyl) -2'-tri- C ₁ fluoromethyl-6'-methyl-2-chloroacetanilide

Kp. C EIe- (mm Hg _) ment

100-101 C (0.05) H

110-120 C (0.1) H

110-120 C (0.1) H

130-140 C (0,1) H

oil

C H N

135-138 C (0.05) .H

135-142 C CO, 05) H

'N

Elemental analysis

Be-funneled the

50.41 4.8 8 4.52

51.94 5.29 4.33

51.94 5.29 4.33

53.34

5.67

• 4.15

48.47 4.43 4,7 4

53.34 5.67

4.15

53,34 5,67, 15

50.52 4.89 4.46

51.80 5.17 4.28

51.69 5.23 4.22

53.07 5.61 4.01.

, 94 4,44 4,70

53.32 5.68 4.14

, 23 5.67 4.13

Table I

Ex.

connection

N- (allyloxymethyl) -2 ^? - fluoromethyl-6'-methyl-2-chloroacetanilide '

N- (propargyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

N- (Isoamyloxymethyl) -2'-fluoromethyl-6'-methy1-2-chloroacetanilide

N- (ethoxymethyl) -2 ^? - fluoromethyl-6 ^f -ethyl-2-. chloroacetanilide

N- (n-propoxymethyl) -2'-trifluoromethyl-6'-tetyl-2-chloroacetanilide

Elemental analysis

Be-

Empirical Kp. ⁰ C EIe- accounting-fun- formula (mm Hg) ment the net

₁ H ₁₁ -ClF-NO

C ₁₁₁ H ¹

123-125 C (0.1) H

oil

N- (isopropoxymethyl) -2'-tri- C ₁ , H _q ClF-NO

fluoromethyl-6'-ethyl-2-chloroacetanilide

HN

oNO ₀ 150 C ² (0.05) H

ClF-NO ₀ 133-135 C

^oil (0.02) H

ClF-NO ₀ Farblo- C

see 01 H

100-105 C (0.01) H

52, 27 52.11 4.70 4.74 4,3 5 4, 34 52, 59 52.44 4.10 4, 14 4.3 8 ^, 34 54, 63 54.66 6.02 6.03 ' 3.98 4.00 51.94 51.32 5.29 5.26 4.33 4.39 53.34 53.74 5.67 5.77 4.15 4.16 53.34 53.43 5.67 5.74 4.15 4.18

"." 22 8 4

The secondary anilides used as starting material to prepare the compounds of this invention are best prepared by conventional chloroactylation of the appropriate primary amine, as described in Example 14.

Example IU

It describes here the preparation of the secondary anilide.

, j

used as starting material for the preparation of a compound of the invention, i. the compound of Example 13 is used.

6.0 g (0.03174 mol) of 2-trifluoromethyl-6-ethylaniline was dissolved in 75 ml of toluene and 3.77 g (0.033 mol) of chloroacetyl chloride was added cautiously. The resulting slurry was heated to the reflux temperature and held there for 4 hours. Then, the mixture was diluted with an equal amount of hexane, then the mixture was allowed to stand. The product crystallized out and the resulting solid became. de filtered off and dried in air; it gave 5.8 g (6% yield); the filtrate was stripped to give an additional 2.7 g of white solid, mp. 121-124 ⁰ C (sealed tube).

Elemental analysis for C ₁₁ H ₁₁ ClF ₃ NO (%): Calculated: C: 49.73; H: 4,17; N: 5.27; Found: C: 49.36; H: 4.09; N: 5.38.

The product was identified as 2'-trifluorocethyl-6 ¹ -ethyl-2-chloroacetanilide. ·

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Primary amines of the type used to prepare secondary anilides by haloacetylation, as described above, are known in the literature; compare e.g. the aforementioned U.S. Patent 3,966,811 and British Application No. 2,013,188.

The compounds of the present invention have been found to be effective herbicides, particularly pre-emergence herbicides, although postemergence activity has also been demonstrated. The pre-emergence tests referred to herein include both greenhouse and field tests. In the greenhouse tests, the herbicide is applied to the surface either after planting the seeds or offshoots, or incorporated into a certain amount of soil, which is spread as a topcoat over the test seeds in seeded test containers. In the field tests, the herbicide can either be incorporated into the soil prior to planting ("PPI"), ie, the herbicide is applied to the surface of the soil, then mixed in, then the culture seeds are seeded or the herbicide becomes on the surface Applied ("SA") after the cult plant has been planted. , '

The surface test method ("S.A.") used in the greenhouse is performed as follows:

Containers, e.g. Aluminum pans of about 24x13x7 cm, or

ΙΟ

Plas.tiktöpfe approximately 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 then seeded with a plant species to be tested and covered with a 1.3 cm high layer of the tester's debris. The herbicide is then added e.g. applied to the earth's surface with a belt sprayer (187 l / ha, 2.11 kgf / cm); each pot then receives 0.64 cm of water from above. Then the pots are placed on garbage tables and watered from below as needed. In another possible method, the irrigation from above can also be omitted. The evaluation of the herbicidal effects takes place about 3 weeks after the treatment.

The herbicide treatment by incorporation into the soil CS. Greenhouse soil is placed in aluminum pans and tapped to 1 to 1.3 cm below the edge.To the soil is added a number of seeds or offshoots of different plant species.To fill the pans completely after the Sowing or planting necessary soil is weighed into a pan The soil and a known amount of active ingredient in the form of a solution or suspension of wettable powder are thoroughly mixed and used to cover the prepared pans. After the treatment, the pans receive a. Initial irrigation from above,

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which corresponds to Oj64 cm of rain, then they are watered from below as needed, so that adequate moisture for germination and growth is present. The irrigation from above can also be omitted. Observation takes place about 2 to 3 weeks after sowing and treatment.

Tables II and III summarize the results of the tests conducted to determine the herbicidal pre-emergence activity of the compounds of this invention; In these tests, the herbicides were incorporated into the soil and watered only from below. Evaluation of herbicidal activity was obtained by a fixed scale based on the percent damage of each species of plant. The ratings are defined as follows:

% Control rating 0-24 0 25-49 1 50 - 74 2 75 - 100 3 undetermined • 5

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

B Cocklebur. , Xanthium

pensylvänicum

C Velvetleaf Abutilon theophrasti

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D morningglory winds Ipomoea sp.

E Lambsquarters Report Chenopodium album

F Smartweed Polygonum sp.

G Yellow Nutsedge Cyperus esculentus

H Quackgrass Wheatgrass Agropyrum repens

I Johnsongrass' Sorghum halepense

J Downy Brome fluffy Trespe Bromus tectorum

K Barnyardgrass · Echinochloa

crus-galli

· Zl.

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Table II

Preemergence test

Verb.von Beisp.Nr. kg / ha Λ B C D P plant species U) U) H I J K 1 11.2 5 _; 6 5 5 ro U) NJ OJ I ro ro ro ro I F 3 o OJ CO i ro ro UJ U) 3 3 2 11.2 U) NJ 1 2 1 1 U) U) CM CM ro ro ro ro 3 '2 NJ OJ 3 3 UY UJ 3 11.2 5.6 3 2 1 0 CM CN 3 3 ro ro 2 3 UY UJ U) U) 2 1 ro ro ro ro 4 11.2 5.6 cn cn NJ UJ 2 1 N) U) ro ro NJ U) 3 3 cn cn ro ro ro ro UY UJ 5 - 11.2 5.6 5 5 3 0 2 o ro ro UJ OJ 3 3 ro ro cn cn 3 1 ro ro ro ro 6 11.2 5.6 cn cn CM (N 1 O 3 1 UJ OJ ro ro 2 1 U) U) ro ro ro ro 3 3 7 11.2 5.6 3 1 1 0 2 1 2 1 OJ U) ro ro ro ro 3 3 1 1 ro ro U) U). 8th 11.2 5.6. U) U) 2 1 O O 2 3 ro ro O O OJ OJ ro ro 3 2 ro ro U) OJ 9 11.2 5.6 OJ UJ NJ NJ ' 2 1 3 2 ro ro ro ro 3 3 3 3 3 1 ro ro OJ OJ 10 11.2 5.6 UY UJ 2 1 1 1 N) UJ U) U) UY UJ 3 1 ro ro 3 o ro ro 3 3 11 11.2 5.5 ro ro 1 1 1 1 NJ U) cn cn U) UJ 3 3 ro ro O 1 ro ro ro ro 12 , 11.2 5.6 ro ro 2 1 O O CM CN 3 1 ro ro OJ OJ U) OJ O 3 U) U) ro ro 13 11.2 5.6 3 3 2 2 CM CN ro ro 3 3 NJ U) 3 3 3 2 ro ro ro ro UY UJ

Vf - yf - 228415

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

soybeans

sugar beets

wheat

rice

sorghum

L soybean

M sugarbeet

N Wheat

0 Rice

P sorghum

B Cocklebur

Q Wild Buckwheat Winch Knotweed

D morning glory

R Hemp sesbania

E Lambsquarters Report

F smartweed

C Velvetleaf

J Downy brome fluffy trespe

S Panicum species

K Barnyardgrass

T Crabgrass

Xanthium pensylvanicum Polygonum convulvulus Ipomoea sp

 Sesbania exaltata Chenopodium album Polygonum sp

 Abutilon theophrasti Bromus tectorum Panicum spp

 Echinochloa crus-galli Digitaria sanguinalis

The results are summarized in Table III.

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5 kg / ha table III M N 0 P B Q Pf lanzerjspezies R 3 F C J S K T • 5, δ 2 3 3 3 0 3 3 3 3 2 3 3 3 3 1.12 1 1 2 3 0 1 D 2 2 2 0 3 3 3 3 Verb.von 0.23 Preemergence test 1 0 2 1 0 1 3 3 1 3 0 2 3 3 3 Beisp.Nr. 0,055 0 0 0 0 0 0 2 1 1 1- 0 0 2 2 3 1 0.0112 0 0 0 0 0 0 0 0 3 1 0 0 1 2 2 5.6 " L 3 2 3 3 1 2 0 3 2 3 0 3 3 3 5 1.12 1 3 2 3 2 0 1 0 1 1 2 0 3 3 3 5 0.28 0 2 0 1 1 0 0 3 1 0 0 0 3 3 3 5 0,055 0 1 0 0 0 0 0 3 0 0 0 0 1 1 3 5 2 0.0112 0 0 0 0 0 0 0 1 0 3 0 0 0 0 1 5 5.5 0 3 3 3 3 1 3 0 3 3 3 1 3 3 3 3 1 12 1 1 1 3 3 1 0 0 1 3 0 0 3 3 3 3 0.28 0 0 0 2 2 0 0 3 0 2 0 0 1 3 3 3 0,055 0 0 0 1 0 0 0 3 0 1  3 0 0 3 3 3 3 0.0112 0 0 0 0 " 0 0 0 0 0 3 0 0 0 3 3 3 0.0055 0 Q 0 0 0 0th 0 0 0 3 0 0 0 1 0 1 5.6 0 3 3 3 3 2 3 0 3 3 3 1 3 3 3 3 1 1.2 0 3 2 3 3 1 3 0 3 3 3 1 3 3 3 3 0.28 0 1 2 2 1 0 1 3 1 1 3 0 2 3 3 3 0,055 0 1 1 1 2 2 1 2 2 1 1 0 0 2 Second 3 4 0 ^ 0112 0 1 0 0 0 0 0 0 0 3 0 0 0 3 3 3 5.6 0 2 3 3 3 1 3 0 3 3 3 1 3  3 3 3 + 1.12 2 2 2 3 3 0 2 0 2 3 3 0 3 3 3 3 0.28 1 2 1 3 3 2 2 3 2 3 3 0 3 3 3 3 "0.05 * 0 1 0 1 2 1 2 0 1 3 1 0 2 3 3 3 0.0112 0 1 0 0 0 1 1 3 0 1 0 1 2 3 3 0 0 1 0 0 0 0 0

Verb.von Beist). No.

, , Table III - Continuation pre-emergence test

Plant species kg / ha LMN OPB Q DREFCJS KT

1333323333313333

5,61,12 0 0,28 0

0.055 0 2 0 12 12 2 2 3 1 '- ¹ - - * - 2 2 2 2 3 1

0 33133133 02 222 1333 0

0.0112 0 2 0

0 3 3 3 3

0 3 3 3 3

0 2 3 3 3

0 113 3

5,6 032230222300333 3

1.12 010010100200C233

0,28 00 00001200000223

0.055 010 1000003200023

2 3 3 3 3 2 3 3 3 3 3 13 3 3 3

5,6 1,12

0.28

0,056 00111000011

12333020133 012120 2 0211

0 0 0

3 3 3 3 2 3 3 3 13 3 3

0.0112 00C010010001023

5, 5, 1.12, 0.20, 0.055 2233323, 33 2313333, 12331131222, 03333, 1223201121103333, 0 00 0000002102333, 0 0000000033

0.0112 0 0 0

5,61,12

0.28 3333323333303333 12-333 0 3322303333 022.2 2 01 023203333

0

0,055

0.0112 0 0 0 0 0 0 1000010000333 000000123

5.5 1.12

 0.28 03333133333133 35 0313 1112122 03335 02121000 11103335

0.055 0100000050001235 0.0112 0 100000000000135

5.6 1.12 0.28 0.055

5,6 1,12 0,28 0.0 12 23312202103333 1212302212203333 0101001001001232 0 5000050 00000020

2333 3233333233 3. 3 12 3 3 3 0 2 2 3 2 3 2 2 3 3 10 0 1110 0

0 3 3 3 3 1031303333 1000002333

0.0112- 0 0 0 0 0 0 0-0155

0 0 0 2 2

"228415

-XJ-

It has been found that the herbicides of the invention possess unexpectedly superior pre-emergence herbicidal properties, particularly in the selective control of hard-to-kill perennial and annual weeds, including perennial weeds such as couch grass, yellow and purple pitch grasses (Cyperaceae), annual broadleaf weeds such as Sida spinosa, Sesbania exaltata, Polygonum sp., Chenopodium album, Amaranthus, and annual grasses such as Sorghum bicolor, Brachiaria plantaginea, Sorghum halepense, Panicum texanum, Panicum miliaceum, Oryza sativa, Rottboellia exaltata, Fox tails (eg Setaria veridis, lutescens and faberi), Echinochloa crus-galli and Digitaria sanguinalis. Also in other resistant species, weed reduction has been achieved, e.g. in Ambrosiaceae, Abutilon theophrasti, Ipomoea sp., Xanthium pensylvanicum, Portulac, etc.

Selective control and increased suppression of the above-mentioned weeds by the herbicides of the present invention has been found in a variety of crops, including corn and soybeans, but also others such as cotton, peanuts, rape, bush beans, wheat and sorghum; these last two crops are. usually less tolerant to the herbicides of the invention than other crops; this reduced tolerance can be reduced by the use of protective means, e.g. Herbicides, improved.

- rf-

In the following discussion of the data, reference will be made to herbicidal application amounts represented by "GR ^" and "GR"; these amounts are given in kg / ha, this value can be converted to lbs / A by dividing by 1.12. GR ^ ₅ defines the maximum amount of herbicide at which 15% or less of the crops cause damage, while GRg _{5 is} the minimum amount necessary to achieve 85% inhibition of the weeds. The amounts of GR and GRg are used as a measure of the potential performance of commercial products, although it will be understood that suitable commercial herbicides may exhibit greater or lesser plant damage within reasonable limits.

Another indication of the effectiveness of a chemical as a selective herbicide is the "selectivity factor"("SF") for a herbicide in certain crops and weeds. It is a measure of the relative degree of harmlessness of crops and of the harmfulness to weeds, and is expressed as the ratio GR _1t ./GR _g r, ie GR.g amount for the crop divided by the GR ₈₅ amount for the crop Weeds, both quantities in kg / ha. In the tables below, the selectivity factors are given in brackets after the amount of GRg for each weed; "NS" means "non-selective"; insignificant or indefinite selectivity is indicated by a dash (-).

228415 7

-yi-

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 desired that the harmlessness factors for the crop plant j-d.h. the herbicide tolerance levels of the crop are high because, for one reason or another, higher herbicide levels are often desired. Conversely, the kills for weed control should be small for economic and possibly ecological reasons, i. The herbicide is said to have high unit activity. However, small amounts of herbicide may not be sufficient to control certain weeds, and more is needed. Therefore, the best herbicides are those that control the largest number of weeds with the least amount of application and the greatest possible harmlessness to the crop, i. Crop tolerance, offer. The selectivity factors (defined above) are therefore used to quantify the relationship between crop harmlessness and control of weeds For the selectivity factors listed in the tables, the higher the numerical value, the greater the selectivity of the herbicide for Weed control in a

. *** irrjTiten Ku It iar.

In order to obtain the unexpectedly superior properties of the compounds according to the invention both on absolute and on the basis of

_JJ_. 228415

In the hothouse, comparative tests were carried out with known compounds which are closest in their chemical structure to the compounds according to the invention. These known compounds are identified as follows (the same nomenclature as for

the compounds of the invention used):

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

B. N- ⁽¹ EthoxyethyD-2-trifluoromethyl-2-chloroacetanilide.

In Tables IV and V, data are summarized for the herbicidal pre-emergence activity, which compares the relative efficacy of the compounds of the present invention and the known compounds as selective herbicides against the resistant and troublesome perennial weeds, Wheatweed and Cyperus esculentus, in soybeans or corn , These weeds are usually associated with such larger crops as corn and soybeans. The test data in Tables IV and V were obtained under identical conditions and represent the average of 2 runs (except for the compound of Example 13 which was used only in a comparative test). The test procedure was the same as described for Tables II and III, a modification consisted of an initial overhead irrigation corresponding to 0.64 cm of rain; the following irrigation was done from below. "NS" means non-selective within the test limits.

2 2 8 415

Table IV

₁₅ (kg / ha) (kg / ha)

• A 1 > 2,2U B 3 1.9 6 Ex. U 2.67 Ex. 5 1.68 Ex. 13 1.12 Ex. 1, U6 Ex. 2.13

Compound Soybean Wheatgrass Cyperus esculentus , _%

> 2.39 (NS) 1.13 (1.98)

0.61 (3.21) 0, UU (U, 45)

0.17 (15.6) 0.17 (15.6)

0.27 (6.22) 0.19 (8.8U)

0.13 (8.62). 0.17 (6.59)

0.26 (5.62) 0.26 (5.62)

0.20 (10.65) 0.17 (12.53)

From Table IV it can be seen that each compound according to the invention had significantly higher selectivity factors (fourth in parentheses) compared to the comfrey and Cyperus esculentus in soybeans, than the known compounds. In particular, it should be noted that the unit activities (relative phytotoxicity per herbicidal unit) of the compounds of the present invention were markedly higher than that of Wheatgrass and Cyperus esculentus, than those of the known compounds, while preserving harmlessness to the crops. Of particular note are the extraordinarily high selectivity factors of the compounds of Examples 1 and 33.

Further comparative data showing the effectiveness of the compounds according to the invention in comparison to the above-known

228415

Compounds against Wheatgrass and Cyperus esculentus in maize are shown in Table. V compiled.

1 GR ₁₅ amount. (Kg / ha) table V G (NS) Rpr quantity (kg / ha) ) 1.13 esculentus 3 • Corn (1.33 Cyperus ) 0.44 (1.98) 4 \ > 2,2 4 couch-grass (4.47 ) .0,17 (1.84) 5 i 0.81 i > 2.39 (7.19 ) 0.19 (4:47) connection 13 0.76. 0.61 (5.85 ) 0.17 (10.2) A 1.94 0.17 (7.04 ) 0.26 (4.47) B 0.76 0.27 (11.2 0.17 (7.04) Ex. 1.83 0.13 (13.18) Ex. 2.24. 0.26 Ex. 0.20 Ex .. Ex.

From Table V shows that each compound of the invention had significantly higher selectivity factors against Wheatgrass and Cyperus esculentus in corn, as the known compounds. Once again, it should be noted that the unit activities of the compounds of the invention against Quecke and Cyperus esculentus were markedly higher than those of the known compounds, while preserving the harmlessness of the culture. Of particular note is the high selectivity factors for the compounds of Examples 3.5 and 13, especially in comparison with those of the known compounds. , '

228415 7

It can be seen from the comparative data of Tables IV and V that the compounds of the present invention exhibit exceptionally higher and unexpectedly superior herbicidal activity over the resistant perennial weeds Wheatweed and Cyperus esculentus in two hatching cultures, i. Soybeans and sharks showed, as the compounds A and B, which are the closest of the known compounds. ·

Data from further pre-emergence tests further indicated that the compounds of the present invention also selectively control squamous, cyperus esculentus and / or other weeds in one or more crops of cotton, peanuts, bush beans, sting, sorghum and / or oilseed rape. In Table VI, e.g. Data summarizing the herbicidal selectivity of the compounds of Example 1 and 3 against mercury in oilseed rape, bush beans, sorghum and wheat. Unless otherwise noted, for the greenhouse tests of Table VI and other tables, the herbicide was incorporated into the soil, and after an initial irrigation from above, irrigation was carried out from below, as described above.

- yf -

228415

Table VI

(Kg / ha)

Compound rapeseed bush beans sorghum VJeizen

GR quantity dg / ha)

Ex. 1 0.86

Ex. 3 1.9

0.90

2.24

couch-grass

0.12 (7.2)

0.12 (7.5)

0.24 - 0.12 (2.0)

0.21 0.12 (1.8)

-. - 0.28 (6.8)

0.28 (8.0)

0.84 - 0.28 (3.0)

0.28 0.28 (1.0)

The compound of Example 1 was also tested in the field to determine its pre-emergence selectivity to foxtail species, Echinochloa crus-galli and Panicum miliaceum in several cultures. The data (obtained from three runs) are listed in Table VII-both for application to the surface (S.A.) and for incorporation into the soil (PPI, i.e., incorporation before planting) of the herbicide. The seeds were planted in a fine silt bed of medium moisture at a depth of 5.08 cm. The first rain (0.51 cm) fell on the day after treatment, the second rain (0.64 cm) two days after treatment; the total amount of rain 22 days after the treatment was 4.5 7 cm. The assessment took place 6 weeks after the treatment. '.'.

Table VII

% Inhibition

crops - field - sweet soybean - earth - tree - bush compound method (kg / ha) maize corn beans nuts wool sorghum]

Beisp.1

S.A. "

'P.P.I.

0.56

1.12

2 ^ 24

'4.48

0.56 ljl2 2.24 4.48

0 0 G

15

32

27

27

40

0 5

13

5 7

20 40

0 0

• 8 22

17 13 15 28

13 20 25

13 32 37 · 82

Fox- echi- panicum tail no milia- - rape species chloa ceum

33

0 0

15 40

62 92 93 98

75

90

98

100

63 93 93 98

75

93

98

• 100

63 83 95 97

23 58 80 85

2 2 8 4

Table VII shows that the compound of Example 1 generally performed better as a selective herbicide when applied to the surface than when incorporated into the soil. In the surface tests, the herbicide selectively controlled the three weeds tested at rates greater than 0.58 kg / ha, while it was harmless to field crops and soybeans up to 4.48 kg / ha (i.e., up to about 15% maximal damage); For sweet corn, peanuts and oilseed rape, the innocuousness was preserved up to more than 2.24 kg / ha, for cotton, sorghum and bush beans it was just under 2.24 kg / ha. In the PPI tests, the compound of Example 1 selectively controlled the foxtail species and Echinochloa crus-galli at less than 1.12 kg / ha, while the harmlessness for field corn, peanuts and oilseed rape at levels up to 2.2 4 kg / ha and soybeans at levels just below 2.24 kg / ha. '

Further field test data for the compound of Example 1 showed selective pre-emergence control of other weeds in soybeans, corn, cottonwool and / or peanuts; These included purple cocksfoot, Setaria faberi and lutescens, Melan, Ipomoea, Xanthium pensylvanicum, Abutilon theophrasti, Polygonum pensylvanicum, Sida spinosa, Portulac, Digitaria sanguinalis, Lab herb, Panicum texanum, Richardia scabra, and / or Acanthospermum hispidum. Of course you can

3? 2 2 8 4 1 5

not all said weeds in all said crops are selectively controlled under all climatic, soil, moisture and / or conditions of use. Selectivity data for the control of the above weeds in soybeans, corn, cotton and peanuts from a variety of field tests at different locations under various conditions of soil, moisture, etc. are listed together in Tables VIII to XI. In the tables, "WAT" means "VJochen after treatment" of the plants with the herbicide either applied to the surface ("SA") or incorporated into the soil before planting ("PPI"); the application rates for each crop / weed combination is referred to as GR .. _ς ~ and GR _Q, respectively.

IO. If

(as defined above). The GR, / GRg. Ratio gives the selectivity factor "SF";"NS" means non-selective, and a dash (-) indicates insignificant or indeterminate selectivity, for example, because the actual GR ₁ J. and GR _β levels were higher or lower than the maximum or minimum amounts present in each Test were used. In Tables VIII through XI, a vacancy means that the plant species was not present in a particular test plot, or that the data was not obtained, or that it was less significant than other available data, eg, some 3 WAT observations favored from 6 IvAT. Data, or 6 WAT data were

omitted because the 3 WAT data were definite.

Table VIII

Cultivated plant / application

Verbin-weed Droppings g _R IQM s F-making process combination WAT 15 85 *

Example 1. Soybeans / S.A. 3

Setaria faberi 5. > 4,48 / <l, 12 (> 4,0)

P.P.I. 3

5> 4.48 / <l, 12 (> 4.0) 8> U, U8 / <1.12 (> 4.0)

Soybeans / S.A. 6 2.52 / 2.8 (NS)

Setaria lutescens

•. P.P.I. 6 1.4 / <1.12 oil, 3)

Soybeans / S.A. 6 2.52 / 2.52 (1.0)

reporting

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

Soybeans / P.P.I. 8 4.4 8 / 2.52 (1.8)

Polygonum

pensy1vanicum

The data of Table VIII show that the compound of Example 1 selectively inhibits Setaria lutescens and faberi, Melde and Polygonum pensylvanicum in soybeans from 6 to 8 WAT with either the S.A. or the P.P.I. 'Procedure controlled.

- νί -

228415

Table IX

Cultivar / applicator-weed - fertilizer combination

WAT ^GR 15 ^{/ GR} 8 5

Example corn / ·

Setaria faberi

Corn / Ipomoea

S.A. S.A.

P.P.I. P.P.I.

S.A. S.A.

P.P.I. P.P.I.

S. F.

Corn / S.A.

Xanthium S.A. pensylvanicum

P.P.I.

P.P.I.

6 4,48 / <l, 12 (4,0)

6.5> 7.84 / 8.4 (NS)

6 4.76 / 1.96 (2.5)

6.5> 6.72 / 4.48 (1.5)

3> 4,48 /> 4,48 (-)

6> 4,48 /> 4,48 (-)

3 4,76 /> 4,4 8 (-)

6 4.76 /> 4.48 (-)

3> 4,48 /> 4,48 (-)

6> 4,48 /> 4,48 (-)

3 4,76 /> 4,48 (-)

6 4.76 /> 4.48 (-)

The data of Table IX show that the compound of Example 1 selectively inhibits Setaria faberi in maize from 6 to 6.5 VJAT with either the S.A. or the P.P.I. Method controlled; the selectivity for Ipomoea and Xanthium pensylvanicum was indeterminate at the test levels, but the repulsion of these plants was shown.

¥ 0

Table X

Cultivated plant / application '

Verbin weed - dung CR / CR

Kobmination method WAT 15 85 SF

Ex. Cotton / S.A. 6 '3.64 / 1.68 (2.17)

purple. S.A. 9 3.36 / 2.24 (1.5)

sedge

P.P.I. 6 3,36 / 4,2 (NS)

Cotton / S.A. 6 3.64 / 3.08 (1.18) '

Sida S.A. 9 3.36 / 4.76 (NS)

• spinous a

P.P.I. 6 3,36 / 4,76 '(NS)

Cotton / S.A. 9 3.36 / 1.96 (1.7) purslane

Cotton / S.A. 7 1.4 / <1.12 (> 1.25)

Digitaria

(smooth or

hairy) P.P.I. 7 0.84 / 1.12 (NS)

Cotton / P.P.I. 7 O, 84 / <1.12 (-) labweed.

Table X shows that the compound of Example 1 selectively controlled purple reed grass and purslane up to 9 WAT, Sida spinosa up to 6 VJAT, and Digitaria up to 7 VJAT; the control of labweed was insignificant or indefinite.

Table XI contains data for the pre-emergence activity of the compound of Example 1 against three resistant annual weeds, i.e. Panicum texanum, Acanthospermum hispidum and Richardia scabra in peanuts for the periods

-IfX

22841 5

up to 12 VJAT. The data of Table XI represent the average of 3 passes in sandy loam containing 1.3% organic matter, 79.2% sand and 10% clay; the

Herbicide was applied to the surface.

(Kg / ha) table XI , inhibition Acanthospermum h. 12 Richardia SC. 12 2.24 3.36 4.48 Panicum texanum WAT 40 • 60 100 WAT 95 peanuts WAT 4 8 4 8 WAT 4 8 12 78 85 95 · 0 90 0 0 95 connection 4 8 12 50 67 68 63 85 88 40 55 78 Ex. 1 5 O 10 0 17 '7. 0 .0 0

228415 7

The data of Table XI show that the compound of Example 1 selectively controlled Texas panicum in peanuts for up to 8 weeks and showed a high degree of control even at 12 WAT at 4.4 8 kg / ha; selective control,. Ie of AcanthospernHim h. was achieved at 3.36 kg / ha for 8 weeks, and complete control was maintained for 12 WAT at 4.4 8 kg / ha; Selective control of Richardia se was achieved at less than 2.2 4 kg / ha for 8 WAT, and at 4.48 kg / ha, 95% control was achieved at 12 WAT.

In further greenhouse tests, compounds of the invention showed selective control of a variety of annual and perennial weeds in various crops. For example, the compound of Example 1 selectively controlled purple sedge grass in both corn and soybeans, and the corresponding culture / weed GR _it ./GR _{ß [} . Ratios (expressed in kg / ha) were 0.6 7 / 0.2 5 (SF = 2.7) in shark and 1.12 / 0.25 (SF = 4.5) in soybeans. The compound of Example 11 showed selective control of "yellow sedge grass and couch grass in corn and soybeans. The culture / Riedgras GR _1C / GR _OC ratios were> 2.24 / 0.95 (SF = 2.4) in corn; , 24 / 0.5 (SF = 4.5) in soybeans and the corresponding GR / GR _g5 ratios for corn and soybeans in wheat were> 2.24 / O, 5 (SF => 4.5)

, Tyr

ty

-Mi-

Test against yellow reed grass in cotton was the GR _; / GR _R , Ratio (average of 2 runs) 1.96 / 0.95 (SF = 2.1). The compound of Example 13 showed similar selective control of yellow reed grass in cotton and of wheatgrass in wheat, the respective GR. ^, GR _R r ratios were 0.7 / 0.47 (SF = 1.7) in cotton and 0.58 / 0.47 (SF = 1.2) in wheat.

In a multi-culture test in the greenhouse, the compounds of Examples 1, 13, 14 u. 15 tested against yellow sedge grass in cotton, soybeans, corn and rice; with respect to yellow reed grass in rice, none of the compounds was selective. However, clearly high selectivities for yellow

, Cotton, Soi.abo.hnen and corn. "· ,, ~ ^ sedge found in / for each of the tested compounds; the respective GR ₁₅ and GR amounts for these compounds are listed in Table XII; the selectivity factors are in parentheses behind each crop.

Table XII

^GR 85 ^OR is'

(kg / ha) (kg / ha)

Verb yellow

Riedgras cotton soybean corn

Example 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.15 0.44 2.8 (6.4) 1.96 (4.5) 1.96 (4.5)

spring-

The compounds of Examples 1 and 13 to 15 were further tested against Wheatgrass in wheat, soybeans and corn; each of the compounds proved to be non-selective in wheat. The selectivity data for the above compounds against whey in soybeans and corn are summarized in Table XIII.

Table "XIII

1 ^GR 85 ^GR 15 81C Ll, 6) Corn 13 (Kg / ha) (68 4,7) 0.69 (9.9) 14 couch-grass (Kg / ha) 46 ( 3,2) 1.68 (4.7) 15 0.07 soybeans (96 2,6) 2.52 (5.6) connection 0.36 O, 2.24 (3.0) Ex. 0.45 1, Ex. 0.75 1, Ex. 1, Ex.

In further greenhouse tests, the compounds of Examples 1 and 3 were tested for their herbicidal activity against a number of annual grasses; These include resistant weeds such as Panicum texanum, Sorghum halepense seedlings, Sorghum bicolor, Brachiaria plantaginea, Panicum miliaceum, Oryza sativa and Rottboellia exaltata. The results of these tests are summarized in Table XIV; the selectivity factors appear in brackets; a dash (-) indicates insignificant or indeterminate selectivity. ·

QJ CJ

LT

r3 fd>

il

ro

Tl

rc5 (ti

CQ U

co

CN O CNR-l - r -I I

HN r-l

UD "3 * O

CN - H ~

-LO »-CO

OA ο λ.

r- ο r- ο ο * - ο ·>

O r-l

CN O CN - ^

rl - H I

VD O CN O

LD '* - r-l * -

CO O

CM **

ο Λ

«" • co ο Λ

CN ^ Η Ο

r-l tH

CN

η cn ο Λ

CO O CN »~

CN

CN Η

r-l

cn •H ω OJ

228415

Table XIV shows that the compound of Example 1 selectively controlled each tested annual weed in soybeans. The compound of Example 3 showed positive selective control over all weeds except Panicum texanum, Panicum miliaceum and Rottboellia at the maximum test level of 1.12 kg / ha; a higher amount would have been necessary to determine the selectivity of the compound to these three weeds.

A particular advantage of a herbicide is its ability to act in a variety of soil types. In Table XV, data summarizing the herbicidal activity of the compound of Example 1 on couch grass in soybeans in a variety of soil types containing various levels of organics and clay are summarized. The herbicide treatments were done by incorporation into the soil, the seeds were planted 0.95 cm deep and were given 0.64 cm of water from above. The observations were made about 3 weeks after the treatment. The selectivity factors are given in brackets. '

Table XV shows that the compound of Example 1 appears to be quite insensitive to soil species having different levels of organics, it has demonstrated selective control of couch grass in soybeans in soils containing organic matter. 1.0% to 60%, and had a percentage of at least 1.8% to about 37%. The data for soya

Table XV

Verbin organic  ; Soil matter volume GR.r amount (Kg / ha) soybeans ^tiK 85 amount (5.1) dung % % 1.12 (> 8.0) Ray sissy 1.0 9.6 > 2.24 couch-grass (-) Ex. 1 Sarpy silty sound , 2.3 30.35 - 0.22 (20.0) Wabash sullen tone 4.3 33.0 2.24 0.2-8 (9.8) Drummer silty sound 6.0 37.0 1.96 0.28 (> 3, 9) Florida sand 6.8 · 1.8 > 2.24 0.11 Florida Torferde 60 • - 0.2 0.58

228415 7

Hf - vi -

beans in Wabash's slack tone were indefinite in this test. Also, the selectivity values reported for sarpy and drummer, silty clay and Florida peatlands are minimum values as the maximum test level was 2.2 4 kg / ha and the herbicide was harmless to soybeans at the same level above 2.24 kg / ha.

Laboratory tests were carried out to determine the resistance of the herbicides according to the invention to leaching into the soil and the resultant herbicidal activity. In these tests, the compounds of Examples 1 and 4 to 6 were dissolved in acetone and then sprayed at various concentrations onto a weighed amount of Ray Schlufflehm and drummer silty clay contained in pots whose drain holes in the bottom of the pot were covered with filter paper. The pans containing the treated soil were leached by placing them on a rotary disc rotating under two jets of a water tank; These were set up so that they gave 2.5 cm per hour of water and thus simulated rain. The leaching rates were adjusted by changing the time on the turntable. The water added to the bottom in the pots was passed through the filter paper and drainage holes. The pots then remained at room temperature for 3 days. The treated soil was then removed from the pots, crumbled and placed as a surface layer on other pots with the same soils.

so jar-

where echinochloa seeds were already seeded. The pots were then placed on greenhouse tables, watered from below, and allowed to grow for 2 to 3 weeks. The visual percentage growth inhibition score was compared to untreated control pots, as were the freshweights of Echinochloa; the data for the controls were obtained from 6 runs, those for the 3-pass test compounds; the. Data are summarized in Table XVI. The fresh weight of the weeds was not measured for the tests in drummer Schluffigem Tonlehm.

Table XVI

Connection amount (kg / ha)

Rain (crn)

.Echinochloa crus-galli

% Inhibition

Fresh weight (g)

^: - * drummer

Ray 'Schlufflehm Drummer Schluffton Ra y Schlufflehm S chluffton

control

0 0 0

Example 2.24

0.56

0.14

Example 4 2.24

5.00 10 (16

1.27

5.08

10 _Γ 16

1.27

5.08

10.16

1.27

5 _; 08

10.16

1.27

5.08

10.16

95

100 100 100 100

100 100 100 100

100 97 95 20

100 100 100 100

Avg.

0 0 0,20

2.65

1.21. 2.73

0.20 0.17 1.74 3.26

0 0 0 0.22

4.37 3.88 4.14 3, 98

Table XVI

Echinochloa crus-galli

% Inhibition 'fresh weight (g)

Connect - lots of rain. 'Drummer

(kg / ha) (cm) Ray Schlufflehm Drummer Schluffto n Ray_ Schlufflehm Schluffton

0.56 '0. - 100 100 '0

1.27 10Ü 100 0

• 5.08 94 100 · 0.24

10.16 52 100 1.97

0.14 0 99 81 0.0.5

1.27 95 99 0.22

5.08 63 94 1.53

10.16 · ·. 14 '54 3.15

, O O A Π

^{BelSp <} ° · 1.27 100 · 10000

  5.08 x 92 100 0.31

10,16. "71 100 · 1.18

0.56 0 99 100 0.02

1.27 100 '100 0

5.08 89 100 ·. 0.44

• 10.16 17 96 '' 3.41

0.14 0 98 70 0

1.27 90 96 0.41 ---- (J "!

5.08 38 85 2.77

10.61 12 47 -3.62

Connection amount (kg / ha) Rain (cm) 3isp. ₆ : '°' ²⁴ 0, · 1.27 5.08 10 ^ 16 0 _; 56 • 0 1.27 5 _r 08 10.16 0,14- 0 1,27 5,08 10.16

Table XVI .. "..

Echinochloa crus-galli

% Inhibition · fresh weight (g)

drummer

Ray Schluff eh drummer Schlufft on Ray Schluffleh m Schluffton

100 0

100 0

99 100 0.03

84 100. 0.64

99 50 0.04 '

99 100 0.02.

90 93 0.41

72 84 1.17

84 12 0.66

90 26 0.43 '

58 20 1.72 · '

29 12 2j92

Table XVI reveals that the compounds of this invention were fairly resistant to leaching into the soil under various precipitation conditions. In particular, each compound of the invention controlled at the rate of 2.24 kg / ha of echinochloa under the equivalent of 10.16 cm of precipitate in Ray Schlufflehm and Drummer Schlufftonlehm, except the compounds of Examples 1 and 5 in Ray Schluff, where control was less than one equivalent of 5.08 cm of rainfall was maintained. Even at the low application rate of 0.14 kg / ha, the compounds of Examples 1, 4 and 5 echinochloa in drummers of silty clay lees under an equivalent of 5.08 cm of precipitate.

Toxicological studies of the compound of Example 1 revealed that the compound is quite harmless. It is slightly toxic (OLD ₅₀ 2'300 mg / kg, MLD ₅₀ > 5010 mg / kg), it causes mild eye irritation _s but no skin irritation. Special handling beyond the normal precautions is not considered necessary.

It thus appears from the foregoing detailed description that the compounds according to the invention exhibited unexpectedly and extraordinarily superior herbicidal properties, both absolutely and in comparison to the structurally closest related known compounds. In particular, the compounds of the invention proved

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as highly selective herbicides, especially in the control of hard-to-kill perennial and annual grasses in soybeans and quays, but also in peanuts, cotton and other crops. Above all, the compounds according to the invention showed excellent control of perennial weeds such as couch grass and weed grasses, as well as resistant annual grasses such as Panicum texanum, Rottboellia, Panicum miliaceum, Brachiaria plantaginaria, Sorghum halepense seedlings, Sorghum bicolor and / or Oryza sativa, while also being less resistant one-year-old grasses and perennial weeds were controlled and / or repressed.

/ HAI h

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 formulations are prepared by mixing the active ingredient with an adjuvant which includes diluents, diluents, carriers and conditioning agents , so as to formulate & preparations in the form of finely divided solid particles, granules, pellets, solutions, dispersions or emulsions. Thus, the active ingredient may be used with an adjuvant such as a finely divided solid, an organic-based liquid, water, a wetting agent, a dispersing agent, an emulsifying agent or a suitable combination thereof.

The preparations according to the invention, in particular liquids and wettable powders, preferably contain as conditioning agents one or more surface-active agents in sufficient amounts to render a certain preparation readily dispersible in water or oil. The incorporation of a surfactant gown in the formulations substantially enhances their effectiveness. The term "surfactant" includes wetting agents, dispersants, suspending agents and emulsifying agents. Anionic, cationic and nonionic agents can be used equally.

2Λ A f 4 Γ 2 8 415

Preferred wetting agents are alkylbenzene and alkylnaphthalenesulfonates, sulfated fatty alcohols, amines or acid amides, long-chain acid esters of sodium isothionate, sodium sulfosuccinate esters, sulfated or sulfonated 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 monoester of Hexitolanhydride (eg sorbitan). Preferred dispersants are methylcellulose, polyvinyl alcohol, sodium lignosulfonates, polymeric alkylnaphthalenesulfonates, sodium naphthalenesulfonate, and polymethylenebisaphthalenesulfonate.

Wettable powders are water-dispersible preparations which contain one or more active ingredients, an inert stretched solid and one or more wetting and dispersing agents. The inert extender solids are usually of mineral origin, eg, natural clays, diatomaceous earth, and synthetic minerals of silica and the like. Such extender include kaolinites, attapulgite clay, and synthetic potassium silicate. The wettable powders according to the invention usually contain about 0 _} 5 to 60

, parts (preferably 5 to 20 parts) of active ingredient, about 0.2 to 25 parts (preferably 1 to 15 parts) of wetting agent, about 0.25 to 25 parts (preferably 1.0 to

si

-χ-

15 parts) of dispersant and 5 to about 95 parts (preferably 5 to 50 parts) of inert stretched solid, all parts being by weight of the total formulation. If necessary, about 0.1 to 2 parts of the inert stretched solid may be replaced by a corrosion or foam inhibitor, or both.

Other formulations contain dust concentrates containing from 0.1% to 60% by weight of active ingredient on a suitable diluent; these dusts may be diluted for use at concentrations of about 0.1 to 10% by weight.

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

In another type of aqueous suspensions, a water-immiscible herbicide is encapsulated so that an in

Γ-u 4. Z υ 4 i D /

an aqueous phase dispersed microcapsule phase is 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, dispersing the non-water-immiscible phase in the aqueous phase, and then a polyfunctional Amine admits. The isocyanate and amine compounds react and form a solid urea shell around particles of the water-immiscible chemical to form microcapsules thereof. In general, the concentration of the encapsulated material is about 480 to 700 g / liter, preferably 480 to 600 g / liter of the whole preparation.

Concentrates are usually solutions of drug in non or partially water miscible solvents, along with a surfactant. Suitable solvents for the active ingredient according to the invention include i.a. Dimethylformide, dimethylsulfoxide, K-methylpyrrolidone, 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 preparations generally contain about 0.1 to 95 parts (preferably 5 to 60 parts) of active ingredient,

about 0.25 to 50 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 adhered to or dispersed in a matrix of inert, finely divided, particulate extender. To aid in the leaching of the drug from the particles, a surface active agent such as those listed above may be included in the formulation. Natural clays, pyrophyllites, illites and vermiculites are examples of useful types of particulate mineral extenders. 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, which are used to prepare the herbicidal granules the active ingredient is sprayed or mixed.

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 surfactant per 100 parts by weight of clayparicles. ,

228415

- χ-

The preparations according to the invention may also contain other additives, e.g. Fertilizers, other herbicides or pesticides, protective agents and the like, used as adjuvants or in combination with one of the adjuvants listed above. Chemicals useful for combination with the active ingredients of the present invention include i.a. Triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic acid or phenol derivatives, thiocarbamates, triazoles, benzoic acids, nitriles, biphenyl ethers and the like, such as:

Heterocyclic nitrogen / sulfur derivatives

2-chloro-4-ethylamino-6-isopropylaminostriazine 2-chloro-4,6-bis (isopropylamino) -s-triazine 2-chloro-4,6-bis (ethylamino) -sole triazine

3-isopropyl-lH-2, l, 3-benzothiadiazin-4 (3K) -one-2,2-dioxide

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

ureas

N '- (4-chlorophenoxy) -phenyl-N, N-dimethylurea. Ν, Ν-dimethyl-N' - (3-chloro-4-methylpheriyl) -substituted 3- (3,4-dichlorophenyl) -l, 1 urea 1,3-Dimethy1-3- (2-benzothiazoly1) urea 3- (p-Chlorophenyl) -1,1-dichloro-1-butyl-3- (3,4-dichlorophenyl) - l-ii-: ethyl urea!

Carbamates / thiolcarbamates

2-Chloroyldiethyldithiocarbamate S-CU-chlorobenzyD-N, N-diethylthiolcarbamate Isopropyl-N- (3-chlorophenyl) -carbamate S-2,3-dichloroallyl-N, N-diisopropylthiolcarbamate Ethyl-N, N-dipropylthiolcarbamate S- Propyldipropylthiolcarbair

Acetamide / acetanilides / Aniline / amides

2-chloro-N, N-diallylacetamide N, N-dimethyl-2,2-diphenylacetamide

N- (2,4-din; ethyl-5- [[(trifluoromethyl) sulfonyl] amino] phenyl) acetamide ".

N-Isopropyl-2-chloroacetanilide 2 ', 6'-diethyl-N-methoxymethyl-2-chloroacetanilide

2'-Methy1-6'-ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide

α, α, α-trifluoro-2,6-dinitro-U, N-dipropyl-p-toluidine N- (1,1-dimethylpropynyl) -3,5-dichlorobenzamide

Acids / esters / alcohols

2,2-Dichloropropionic acid 2-Methyl-4-chlorophenoxyacetic acid 2,4-Dichlorophenoxyacetic acid Methyl ~ 2- ["4- (2,4-dichlorophenoxy) -phenoxy-3-propionate 3-amino-2, 5-dichlorobenzoic acid.

2-Kethoxy-3, B-Dichlorobenzoic Acid

22841

2, 3, '6-trichlorophenylacetic acid

N-1-naphthyl phthalamic acid.

Sodium 5- [2-chloro-U- (trifluoromethyl) phenoxy] -2-nitrobenzoate

U, 6-dinitro-o-sec-butylphenol

N- (phosphonomethyl) glycine and C, "Konoalkylamin- and alkali metal salts and combinations thereof

' Ether

2, U-dichlorophenyl-4-nitrophenyl ether 2-chloro-a, a, a-trifluoro-p-tolyl-3-ethoxy-4-nitrodiphenyl ether

various

2,6-dichlorobenzonitrile monosodium acids; ethanarsonate disodium methanarsonate

Fertilizers useful in combination with the active ingredients are e.g. Aironia nitrate, urea, potash and superphosphate. Other useful additives are i.a. Substances in which plant organisms are rooted and grow, e.g. Compost, manure, humus, sand and the like

For herbicide formulations of the type described above, various exemplary embodiments are given below. ·

- γι -

I. Emulsifiable concentrates

% By weight

A. Compound of Example No. 1 50.0 calcium dodecyl benzene sulfonate /

PoIyoxyethylenether mixture

(e.g., Atlox 3437F) 4.85 calcium dodecyl benzene sulfonate

(FIoMo 60H). · 0.15

Cq aromatic solvent 4 5.00

\ 100,00

B. Compound of Example No. 4. " 85.0 Calcium Dodecylsulfonate / Alkylaryl Polyether Alcohol Mixture 4.0 _Cq Aromatic Hydrocarbon Solvent 11.0

100.0

C. Compound of Example No. 6 5.0 calcium dodecylbenzoylsulfonate / polyoxyethylene ether mixture

(e.g., Atlox 3437F) 1.0

Xylene 94.0

, 100.0

II. Liquid Concentrates

A. Compound of Example No. 4 10.0

Xylene 90.0

100.0

B. Compound of Example # 5 85.0 Dimethylsulfoxide " 15.0 .

C. Compound of Example No. 6 50.0 N-methylpyrrolidone '50 .0

) 100.0

D. Compound of Example No. 7 5.0 Ethoxylated castor oil 20.0 Rhodamine B '. 0.5 dimethylformamide 74.5

III. emulsions

% By weight

A. Compound of Example No. 12 40.0 Polyoxyethylene / Polyoxypropylene Block

Copolymer with butanol (z ♦ B.Tergitol XH) '4.0

Water 56.0

B. Compound of Example No. 13 5.0 Polyoxyethylene / Fexyoxypropyls

Block copolymer with butanol. 3.5 ,,

V.'asser '91.5

• 100.0

IV. Wettable powders

A. Compound of Example No. 1 25.0

Sodium lignosulfonate 3.0

Sodium N-methyl-N-oleyl taurate 1.0

• Amorphous silica (synthetic) '71,0

- -YES -

Wt.%

B. Compound of Example No. 12 80,00 Sodium dioctylsulfosuccinate. 1.25 calcium lignosulfonate 2.75 amorphous silica (synthetic) 16.00

100.00

C. Compound of Example IJr. 13 10.0 sodium lignosulfonate '. · 3.0 sodium N-methyl-N-oleyl taurate 1.0 kaolinite clay 86.0

100.0

V. dusts

A. Compound of Example No. 7 2.0

Attapulgite .-. 98.0

100.0

B. Compound of Example No. 8 · 60.0 Hontmorillonite UO, 0

100.0

C. Compound of Example No. 9 30.0 Bentonite 70.0

100.0

D. Compound of Example No. 10 1.0 Diatomaceous earth 99, 0

100.0

ζ, j - Μί νι. Granule

A. Compound of Example No. 1 15.0 Granulated attapulgite (20 / HO sieve) 85.0

, '. 100.0

B. Compound of Example No. 6 30.0 Diatomaceous earth (20/40) 70.0

C. Compound of Example No. 12 0.5 Bentonite (20MO) 99.5

, 100.0

D. Compound of Example No. 13 5.0 Pyrophyllite (20/40) 95.0

VII. Microcapsules

A. Compound of Example No. 1

encapsulated, in polyurea shell 49.2

Sodium lignosulfonate (e.g., Reax 88 B) 0.9 Water 49.9

B. Compound of Example No. 12

encapsulated in polyurea shell 10.0

Potassium lignosulfonate (eg Reax C-21) 0.5 VJasser. 89.5

C. Compound of Example .No. 13

encapsulated in polyurea shell 80.0

Magnesiuir.salz of lignosulfate

(Treax LTM). ' -2.0

VJasser 18,0

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 aqueous media. The application of the compositions as liquids and solid particles to the soil can be carried out by conventional methods, e.g. with engine atomizers, tank and hand sprayers or spray atomizers. 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 essential and critical for the use according to the invention. The exact amount of active substance 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 Used acetanilide. ' In some cases, larger or smaller quantities may be needed. The expert can

228415

based on the description, including the examples, easily determine the optimal amount for each case.

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, Second Edition, Unabridged (1961). The term refers to any substance or hedge in which plants can root and grow, and includes not only soil, but also compost, manure, dung, humus, sand, and the like that can sustain plant life.

Claims (22)

Erfindungsanspruchi 1 «herbicidal preparation, characterized in that it comprises an adgyyans and a herbicidally effective amount of a compound of formula I. ClCH _x L .CH ₇ OR wherein E is C 1-6 alkyl or alkoxyalkyl or alkenyl or alkynyl of up to 5 carbon atoms, and IL, hydrogen, methyl or ethyl; with the proviso that when R 1 is hydrogen, R is isopropyl, and when R 1 is ethyl, R is ethyl, n-propyl or isopropyl. 2 ", preparation according to item 1, characterized in that d l Γ in the compound R meant Cg ^ alkyl 3. Preparation according to item 2, characterized in that in the compound of formula I R ^ is methyl. 4 »Preparation according to item 3, characterized in that the compound of the formula I is N - = (ethoxymethyl) -2- ^t- trifluoromethyl-6- ^l- methyl-2-dhloracetanilide, 5. Preparation according to point 3, characterized in that the compound of formula I and N- (n ~ propoxymethyl) -trifluoromethyl-6 -methyl ^ ^f 2 -2 ^f - is chloracetanalid. 6 "preparation according to item 3» characterized in that the compound of formula I is N-Clsopropoxymethyl) ^ ^{1-trifluoromethyl-6 f} is methyl-2-chloroacetanilide ~. 7. Preparation according to item 3, characterized in that the compound of formula I is N- (isobutoxymethyl) -2'-trifluoromethyl-e'-methyl-S-chloroacetanilide. 8. Preparation according to item 2, characterized in that in the compound of formula IR ^ ₁ ethyl. 9 · preparation according to item 8, characterized by the compound of the formula I is N-CEthoxymethyl ^^ '- trifluoromethyl-6'-ethyl-chloroacetanilide. 10, preparation according to item 8, characterized in that the compound of formula I is N-Cn-propoxymethyl) ^ ¹ - trifluoromethyl-6 ^l -ethyl-2-cliloraoetanilide. 11. A preparation according to item 8, characterized in that the compound of formula I is N- (isopropoxymethyl) -2- ^f -trifluoromethyl-6'-ethyl ^ -chloroacetanilide. 12e preparation according to item 2, characterized in that in the compound of formula I is IL, Vihydrogen. Preparation according to item 12, characterized in that the compound of formula I is N- (isopropoxymethyl) -2- ^f -trifluoromethyl-2-chloroacetanilide. 14, preparation according to item 1, characterized in that in the compound of formula I R is an alkenyl radical having up to 5 carbon atoms. '' 15.. Preparation according to item 14, characterized in that the compound of formula I is N- (allyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide » 16. A preparation according to item 1, characterized in that in the compound der.Formel I R is an alkynyl radical having up to 5 carbon atoms. 17 "preparation according to item 16, characterized in that the compound of formula I is N-CPropargyloxymethyl) - ^ 'trifluoromethyl-O'-methyl ^ -chloroacetanilide. Preparation according to item 1, characterized in that in the compound of the formula I R denotes an alkoxyalkyl radical having up to 5 carbon atoms. « IQ. Preparation according to item 18, characterized by -2 .'- trluorin <y the compound of the formula I is N-methoxyethoxymethyl- ^1- methyl-2-chloroacetanilide. Method for combating undesirable plants in crops, characterized in that a herbicidally effective amount of a compound of formula I is applied to the site thereof 21. The method according to item 20, characterized in that in the compound of formula I R is C ^ ^ - alkyl. 22, method according to item 21, characterized in that in the compound of formula I R ^ is methyl. 23. The method of item 22, characterized in that the compound of formula I ^f is methyl-2-chloroacetanilide N- (Etho2qymethyl) ^-2-l --trifluormethyl. 6 24. The method according to item 22, characterized in that the compound of formula I is N- (n-propoxymethyl) -2- ^t- trifluoromethyl-6- ^t- methyl-2-chloroacetanilide. " 25. The method according to item 22, characterized in that the compound of formula I is N- (isopropoxymethyl) -2 ^f trifluoromethyl-6 ^1- methyl - ^ - chloroacetanilide. 26. The method of item 22, characterized in that the compound of formula I, N- (isobutoxymethyl) -2-trifluoromethyl ^{f-6 f-1-2} -methyl chlor.acetanilid is. 27. The method according to item 21, characterized in that in the compound of formula I R ^ ethyl. 28.. Process according to item 27, characterized in that the compound of the formula I is N- (ethoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide. 29. The method according to item 27, characterized in that the compound of formula I is N- (n-propoxymethyl) -2 ¹ -trifluoromethyl-6'-ethyl-2-chloroacetanilide. 30. The method according to item 27, characterized in that the compound of formula I is N- (isopropoxymethyl) -2'-trifluoromethyl-6 ^1- ethyl-2-chloroacetanilide. 31. The method according to item 21, characterized in that in the compound of formula. I R ^ is hydrogen. 32. The method according to item y \ , characterized in that the compound of formula I is N- (isopropoxymethyl) -2 ^l -trifluoromethyl-2-chloroacetanilide. Process according to item 20, characterized in that in the compound of the formula I R is an alkenyl radical having up to 5 carbon atoms. 34. A process according to item 33, characterized in that the compound of formula I is N-C-alloxymethyl ·) - ^ '- trifluoromethyl-6 ¹ -methyl-2-chloroacetanilide, 35 »Process according to item 20, characterized in that in the compound of the formula I E is an alkynyl radical having up to 5 carbon atoms, 36. The method according to item 35, characterized in that the compound of formula I is N- (propargyloxymethyl) - 2 ^t -trifluoromethyl-6 ^f -methyl-2-chloroacetanilide. Process according to item 20, characterized in that in the compound of the formula T R denotes an alkoxyalkyl radical having up to 5 carbon atoms. 38. The method according to item 37, characterized in that the compound of formula I is N- (methoxyethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide. 39. Method according to item 20, characterized in that the crops are maize, sorghum, soybeans, cotton, peanuts, bush beans, veizae and oilseed rape. 40. The method of item 39, characterized in that the compound of formula I is N-CEthoxymethyl) - ^ ¹ - trifluoromethyl-ö'-methyl-HrChloracetanilid. Method of controlling undesirable plants in maize crops, characterized in that a herbicidally effective amount of N- (ethoxymethyl) -2- ^f- trifluoromethyl-6 ^! Methyl-2-chloroacetanilide is applied. 42. A method for controlling unwanted plants in soybeans, characterized in that a herbicidally effective amount of N- (ethoxymethyl) ^ • trifluoromethyl-e'-methyl ^ -chloroacetanilide is applied to their location. · A method for controlling unwanted plants in cotton crops, characterized in that a herbicidally effective amount of N- (ethoxymethyl) -trifluoromethyl-S'-methyl-chloroacetanilide is applied to the site thereof. 44. A method for controlling undesirable plants in rape crops, characterized in 'that on the location thereof a herbicidally effective amount of N- (ethoxymethyl ·) · ^{t f} -2-trifluoromethyl-6-methyl-2-chloroacetanilide is applied. 45 »· Method of controlling unwanted plants in Bush bean crops, characterized in that a herbicidally effective amount of N- (ethoxymethyl) -2'-trifluoromethyl-6 ^1- methyl-2-chloroacetanilide is applied to their location,