CH645878A5 - HERBICIDES 2-HALOGEN ACETANILIDES. - Google Patents

Description

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

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

The compounds according to the invention, which are characterized by an alkoxymethyl radical on the anilide nitrogen, an alkoxy radical in one ortho position and a specific alkyl radical in the other ortho position, correspond most closely, as far as is known, to those of US Pat. Nos. 3,442,945 and 3,547,620 , in particular the compounds 2'-tert-butyl-2-chloro-N-methoxymethyl-6'-methoxy-acetanilide and their bromo analogue (cf. 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. Patents 4,070,389 and 4,152,137 provide a general formula which includes compounds of the type described in U.S. Patents 3,442,945 and 3,547,620. However, the only example compound described which has an alkyl radical in one ortho position and an alkoxy radical in the other ortho position has an alkoxyethyl radical on the anilide nitrogen atom; Compounds of this type are discussed in detail below.

Other less relevant publications are BE-PS 810 763 and German application 2 402 983; to

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the compounds described therein include compounds of the type described in U.S. Patents 4,070,389 and 4,152,137 which are characterized by an alkoxyalkyl radical having two or more carbon atoms between the anilide nitrogen atom and the oxygen atom of the alkoxy part. The closest specific statements in BE-PS 810 763 and German application 2 402 983 are compounds which contain an ethoxyethyl radical on the anilide nitrogen atom, a methoxy or ethoxy radical in an ortho position and a methyl or ethyl possess radical in the other ortho position (cf. 810 763, compounds Nos. 7, 13 and 18); other less relevant homologs of these compounds are also described, e.g. Compounds Nos. 6, 9, 16 and 17 which have substituted methoxyethyl or methoxypropyl radicals on the nitrogen atom, a methoxy or ethoxy radical in one ortho position and a methyl radical in the other ortho position.

U.S. Patent 3,442,945 contains some herbicide data relating to those compounds mentioned above, the chemical configuration of which is most closely related to the compounds of the invention; some data are also given in the other patents for other analog and homologous compounds which are less closely related in their chemical structure, e.g. the compounds 6 and 9 of BE-PS 810 763. In particular, these references describe herbicidal activity against a large number of weeds, but they do not give any data for compounds which additionally and / or at the same time the difficult-to-kill perennial weeds such as mercury and yellow sedge, as well as a wide range of annual weeds including one-year-old broad-leaved weeds such as thorny sida, hemp sesbania, thorn apple, etc., and annual annual weeds such as sorghum halepense seedlings, sorghum bicolor, brachiaria, panicum species, red rice and raoul grass. while they also control other harmful annual or perennial weeds such as Knotweed Family, Melde, Amaranthus, Foxtail, Digitaria sanguinalis and Echinochloa crus-galli.

An extremely useful and desirable trait of herbiaids is the ability to keep weeds under control for a longer period of time, the longer during each growing season, the better. With many known herbicides, sufficient weed control is only achieved for 2-3 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 life in the soil.

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

Another disadvantage of many known herbicides is the limitation of their applicability to certain types of soil, i.e. while some herbicides are effective in soils with a low organic content, they are ineffective in other soils with a high organic content, or vice versa. It is therefore advantageous if a herbicide can be used in all types of soil, from light organic to heavy clays and clays.

Another disadvantage of many known herbicides is the limitation to a particularly effective application, i.e. Apply to the surface before emergence or work into the soil. The ability to apply a herbicide in any way, by applying it to the surface or incorporating it into the soil, is very desirable. Finally, a disadvantage of some herbicides is the need to take special precautions for their handling because of their toxicity. A herbicide should also be safe to use.

The invention therefore relates to a group of herbicidal compounds which avoid the above-mentioned disadvantages of known herbicides and offer a number of advantages which have not hitherto been combined in a single herbicide group.

The invention provides herbicides which control perennial and annual weeds which are difficult to kill, e.g. Mercury, yellow sedge, sorghum halepense seedlings, Sida spinosa, hemp sesbania, sorghum bicolor, brachiaria, panicum species, red rice and roul grass, as well as a wide range of other harmful weeds, such as e.g. Knotweed family, Melde, Amaranthus, Thorn Apple, Foxtails, Echinochloa and Digitaria. Furthermore, they enable an increased suppression of resistant weeds such as Ambrosiaceae, Abutilon, Winds and Xanthium, while they remain harmless for many crops such as soybeans, cotton, peanuts, oilseed rape and / or bush beans.

Another object of the invention is to maintain the herbicidal activity in the soil for periods of up to 18 weeks.

The invention also relates to herbicides which are effective against leaching or dilution in high humidity, e.g. are persistent in heavy rainfall.

The invention further relates to herbicides which are active in a wide range of soil, from light to medium organic soils to heavy clay or loam.

Another advantage of the herbicides according to the invention is their flexible application, e.g. by applying it to the surface before emergence or by working it into the ground.

Finally, the herbicides according to the invention have the advantage that they are harmless and do not require any special handling measures.

From the following detailed description, these and other objects of the invention will become more apparent.

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

It has now been found that a selective group of 2-haloacetanilides, which are characterized by specific hydrocarbyloxymethyl radicals on the anilide nitrogen atom, specific alkoxy radicals in one ortho position and hydrogen or a methyl or ethyl radical in the other ortho position, are unexpectedly superior and have excellent herbicidal properties compared to known herbicides, including related and known homologous compounds.

An essential property of the herbicide preparations according to the invention is their ability to keep a broad spectrum of weeds under control. These include weeds that can be controlled by conventional herbicides, as well as a large number of weeds that have previously, individually or collectively, escaped control by a single class of known herbicides. At the same time, they are harmless to crops of one or more crops, which include in particular soybeans, cotton, peanuts, rapeseed, haricot beans and others. While known herbicides to control a number of weeds and occasionally certain resistant

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Weeds are useful, the unique herbicides according to the invention have been shown to be capable of controlling or largely suppressing a large number of resistant perennial and annual weeds, such as the perennial weeds mercury and yellow sedge, annual broadleaf weeds such as thorny sida, hemp sesbania, thorn apple, knot apple Plants, reports, goose-footed plants, as well as annual grasses such as Shattercane, Brachiaria, Sorghum halepense seedlings, Panicum species, red rice, raoul grass, and other harmful weeds such as autumn panicum, foxtail, barnyard grass and digitaria. Improved weed control has also been achieved with resistant weeds such as Ambrosiaceae, Abutilon, Winds and Xanthium.

The compounds according to the invention are represented by the formula

OR

characterized in which

R denotes ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl,

Rx is methyl, ethyl, n-propyl or isopropyl, and R2 is hydrogen, methyl or ethyl, with the proviso that when R2 is hydrogen, Rj is ethyl and R is allyl when

Rj is ethyl, Rj is methyl and R is isopropyl when

R 1 is methyl, R is ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl if R 1 is ethyl, R is sec-butyl, allyl or propargyl if R 1 is n-propyl, R is ethyl and if R 1 is isopropyl, R represents ethyl or n-propyl.

The preferred compound according to the invention is 2 '- methoxy-6'-methyl-N- (isopropoxymethyl) -2-chloroacetanilide.

Further compounds according to the invention are: 2'-methoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide, 2'-methoxy-6'-methyl-N- (1-sec.-butoxymethyl) -2-chloro acetanilide,

2'-ethoxy-6'-methyl-N- (allyloxymethyl) -2-chloroacetanilide, 2'-ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide,

2'-ethoxy-N- (allyloxymethyl) -2-chloroacetanilide, 2'-methoxy-6'-ethyl-N- (isopropoxymethyl) -2-chloroacetanilide, 2'-ethoxy-6'-methyl-N- (l- methylpropoxymethyl) -2-chloroacetanilide,

2'-n-propoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide, 2'-isopropoxy-6'-methyl-N- (ethoxymethyI) -2-chloroacetanilide and 1

2'-isopropoxy-6'-methyl-N- (n-propoxymethyl) -2-chloroacetanilide.

The usability of the compounds according to the invention as active ingredients in the herbicide preparations prepared therewith, and the application process are described below.

The compounds according to the invention can be prepared in various ways. So you can e.g. by the azomethine route described in the aforementioned U.S. Patents 3,442,945 and 3,547,620. In this azomethine process, the suitable primary aniline is reacted with formaldehyde to give the corresponding methylene aniline (substituted phenylazomethine), which is then reacted with a halogenoacetylating agent such as chloroacetylchloride or chloroacetyl anhydride !. The appropriate alcohol is then reacted to give the corresponding N-alkoxymethyl-2-chloroacetanilide as the end product.

Another method described in more detail below involves the transetherification of the appropriate N-methylene ether - 2-haloacetanilide with the desired alcohol to the corresponding transetherified N-hydrocarbylmethyl-2-halo-genoacetanilide.

Yet another process for the preparation of compounds according to the invention provides for N-alkylation of the anion of the suitable secondary 2-haloacetanilide with an alkylating agent under basic conditions. The N-alkylation process is described in more detail in Examples 11-14.

example 1

This example describes the preparation of a preferred embodiment, namely 2'-methoxy-6'-methyl-N- (iso-propoxymethyl) -2-chloroacetanilide.

0.025 mol of 2'-methoxy-6'-methyl-N- (methoxymethyl) -2-chloroacetanilide in 100-150 ml of isopropanol, which contained about 0.02 mol of methanesulfonic acid, was refluxed in a Soxhlet extractor held, whose thimble contained 25 g activated 3A molecular sieve to absorb the released methanol. The course of the reaction was followed by gas liquid chromatography. After the reaction had ended, the excess alcohol was removed in vacuo and the residue was taken up in ether or chloroform. The solution was washed with 5% sodium carbonate solution, dried (Mg2S04) and evaporated. The product was purified using Kugelrohr distillation. Yield 55%; pale amber solid, mp 40-41 ° C.

Elemental analysis for: C14H20ClNO3 (%)

calculated: C 58.84 H 7.05 N 4.90 Cl 12.41 found: C 58.55 H 7.08 N 4.89 Cl 12.45 The product was identified as the compound mentioned at the beginning.

EXAMPLES 2 TO 9 Practically the same procedures, amounts of reactants and general conditions described under Example 1 were used, but the appropriate alcohol was substituted for the transetherification to the end product to give other N-hydrocarbyloxymethyl-2- corresponding to the above formula to produce haloacetanilides; these compounds are listed in Table I.

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TABLE I

Example connection empirical Kp. ° C analysis

No. Formula (mm Hg) Element Calculated Found

2nd

2'-methoxy-6'-methyl-N- (ethoxy-

C13H18C1N03

170

c

57.46

57.19

methyl) -2-chloroacetanilide

(0.1)

H

6.67

6.70

N

5.16

5.11

3rd

2'-methoxy-6'-methyl-N- (l-methyl-

c15h22cino3

C.

60.10

59.90

propoxymethyl) -2-chloroacetanilide

H

7.40

7.36

N

4.67

4.62

Cl

11.83

11.97

4th

2 "-ethoxy-6'-methyl-N- (allyloxy-

c10h20cino3

110

C.

60.50

60.30

methyl) -2-chloroacetanilide

(0.07)

H

6.77

6.80

N

4.70

. 4.64

Cl

11.91

11.69

5

2'-ethoxy-6'-methyl-N- (propargyl-

c15h18cino3

140

C.

60.91

60.98

oxymethyl) -2-chloroacetanilide

(0.1)

H

6.13

6.14

N

4.74

4.74

Cl

11.99

11.94

6

2'-ethoxy-6-methyl 1-N- (1-methyl 1-

c16h24cino3

135

c

61.24

60.98

propoxymethyl) -2-chloroacetanilide

(0.09)

H

7.71

7.69

N

4.46

4.42

CI

11.30

11.22

7

2'-methoxy-6'-methyl-N- (isobutoxy-

CECINO,

140

c

60.10

59.88

methyl) -2-chloroacetanilide

(0.1)

H

7.40

7.41

N

4.67

4.62

Cl

11.83

11.82

8th

2'-methoxy-6'-methyl-N- (cyclo-

C15H20ClNO3

145

c

60.50

60.26

propylmethoxymethyl) -2-chloroacet-

(0.1)

H

6.77

6.77

anilide

N

4.70

4.66

Cl

11.91

11.80

9

2'-methoxy-6'-ethyl-N- (isopropoxy-

c15h22cino3

Oil c

60.10

59.81

methyl) -2-chloroacetanilide

H

7.40

7.46

N

4.67

4.61

Cl

11.83

11.71

Example 10

Preparation of the tertiary N- (methoxymethyl) anilide starting materials used to produce the end products of Examples 1 to 9.

The N-methylene ether substituted 2-chloroacetanilide starting materials used in Examples 1 to 9 were prepared by alkylating the appropriate secondary 2-haloacetanilide using the above-mentioned N-alkylation process. In this example, this process is described with respect to the preparation of the starting material of Example 1.

0.025 mol of 2'-methoxy-6'-methyl-2-chloroacetanilide, 0.05 mol of bromomethyl methyl ether and 2 g of benzyltriethylammonium bromide were dissolved in 70 ml of methylene chloride. 40 ml of 50% sodium hydroxide solution was then added portionwise with stirring and cooling, keeping the temperature between 20 and 25 ° C. After the addition was complete, the mixture was stirred for a further 1.5 h. 100 ml of water was then added with cooling and the layers separated. The methylene chloride layer was washed twice with 30 ml of saturated sodium chloride solution, dried (Mg2S04) and evaporated. The residue was crystallized or distilled in vacuo, giving a yellow liquid, bp 140 ° C at 1.2 mm Hg.

45 elementary analysis for: C12H16C1N03 (%)

calculated: C 55.92 H 6.26 N 5.44 found: C 56.15 H 6.33 N 5.36 The product was obtained as 2'-methoxy-6'-methyl-N- (meth-oxymethyl) - 2-chloroacetanilide identified.

50

In the same way, the N-methylene ether-substituted 2-chloroacetanilide starting materials of Examples 2 to 9 were prepared by alkylating the corresponding secondary anilide with bromomethyl methyl ether, and the analogous 55 chloromethyl and iodomethyl methyl ethers can also be used.

The secondary anilide starting material used in this example to prepare the tertiary N-methoxymethyl compound was prepared by chloroacetylating the corresponding primary amine as follows:

0.03 mol of 2-methoxy-6-methylaniline in 30 ml of methylene chloride was stirred vigorously with 0.05 mol of 10% sodium hydroxide solution, while a solution of 0.033 mol of chloroacetyl chloride in 20 ml of methylene chloride was added 65; the temperature was kept between 15 and 25 ° C. with the aid of external cooling. After the addition had ended, the reaction mixture was stirred for a further 30 min, the layers separated and the methylene chloride layer with

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Washed out water, dried and evaporated in vacuo. The product was crystallized from a suitable solvent to give white needles, mp. 130-131 ° C.

Elemental analysis for: Ci0H12C1NO2 (%)

calculated: C 56.21 H 5.66 N 6.56 Cl 16.59 found: C 56.16 H 5.66 N 6.57 Cl 16.55 The product was obtained as 2'-methoxy-6'-methyl- 2-chloroacetanilide identified.

The secondary anilides used as starting materials in Examples 2 to 9 were prepared in a similar manner.

The primary amines used to make the above secondary anilides can be made by known methods, e.g. by catalytic reduction of the corresponding substituted nitrobenzene in ethanol using a platinum oxide catalyst.

As already mentioned, the products according to the invention can also be obtained directly from the secondary anilide using the N-alkylation process mentioned, without first producing the N-hydrocarbyloxymethyl intermediate described in Example 10, which is then transetherified to the end product described in Example 1 becomes. Examples 11 to 14 describe the preparation of compounds according to the invention using the N-alkylation process.

Example 11

4.35 g of 2'-n-propoxy-6'-methyl-2-chloroacetanilide, 3.4 g of chloromethyl ethyl ether, 1.5 g of benzyltriethylammonium chloride were mixed in 250 ml of methylene chloride and cooled. To the mixture was added 50 ml of 50% NaOH at 15 ° C and stirred for 2 hours, then 100 ml of water was added. The layers were separated, washed with water, then dried over MgSO4 and evaporated. The product was purified with Kugelrohr distillation and 4.8 g (89% yield) of clear liquid, bp. 130 ° C. at 0.07 mm Hg.

Elemental analysis for: C15H22C1N03 (%)

calculated: C 60.10 H 7.40 Cl 11.83 found: C 59.95 H 7.39 Cl 11.79 The product was obtained as 2'-n-propoxy-6'-methyl-N - (ethoxymethyl) -2-chloroacetanilide 'identified.

Example 12

5.55 g of 2'-isopropoxy-6'-methyl-2-chloroacetanilide, 4.4 g of chloromethyl ethyl ether, 2.5 g of benzyltriethylammonium chloride in 250 ml of methylene chloride were mixed and cooled to 0 ° C. To the mixture was added 50 ml of 50% NaOH all at once while the temperature was kept below 15 ° C. The mixture was stirred for 2 hours, cooled, then 100 ml of water was added. The layers were separated, washed with water, dried over MgSO4 and evaporated to give 4.7 g (69% yield) of product as a yellow oil. Elemental analysis for: C15H52CIN03 (%)

calculated: C 60.10 H 7.40 N 4.67 Cl 11.83 found: C 60.10 H 7.40 N 4.64 CI 11.73 The product was obtained as 2'-isopropoxy-6'-methyl- N - (ethoxymethyl) -2-chloroacetaniiide identified.

Practically the same procedure as described in Examples 11 and 12 was used, but chloromethyl propyl ether was used as the alkylating agent. 5.0 g (88% yield) of a yellow oil were obtained.

Elemental analysis for: C16H24C1N03 (%)

calculated: C 61.24 H 7.71 N 4.46 Cl 11.30 found: C 61.18 H 7.76 N 4.43 CI 11.31 The product was obtained as 2'-isopropoxy-6-methyl-N - (n - propoxymethyl) -2-chloroacetanilide identified.

Example 14

The same procedure as described in Examples 11 to 13 was used, but the appropriate secondary anilide and halomethyl allyl ether were substituted. A yellow oil, bp. 134 ° C. at 0.08 mm Hg (spherical tube) was obtained.

Elemental analysis for: C14H18C1N03 (%)

calculated: C 59.26 H 6.39 N 6.94 Cl 12.49

found: C 59.20 H 6.41 N 6.95 Cl 12.52

The product was identified as 2'-ethoxy-N- (allyloxymethyl) -2-chloroacetanilide.

It has been found that the herbicides according to the invention are unexpectedly superior as pre-emergence herbicides, in particular for the selective control of weeds which are perennial and annual which are difficult to kill; these include perennial weeds such as mercury and yellow sedge, annual broad-leaved weeds such as thorny sida, hemp sesbania, thorn apple, knotweed plants, notifications, goose-foot plants, and annual grasses such as sorghum halepense seedlings, shattercane, red panicumuminea, brachiaria plantina Rice, wild millet, roul grass, fox tails (e.g. green and large), barnyard grass and large digitaria. Also, compared to known acetanilides, there has been an improved weed reduction in other resistant species such as e.g. Ambrosiaceae, Abutilon, Winds and Xanthium.

Selective control and improved suppression of the weeds mentioned with the herbicides according to the invention has been observed in a large number of crops, including soybeans, cotton, peanuts, oilseed rape and bush beans. Selectivity was also demonstrated in some tests on sugar beets, field corn, sweet corn, wheat, barley and sorghum; however, these crops are generally less tolerant of the herbicides according to the invention than the crop plants mentioned above. It is obvious to the person skilled in the art that not all of the weeds listed above are selectively controlled by all compounds according to the invention under all conditions with regard to climate, soil type, moisture and / or application method.

To present the unexpectedly superior properties of the compounds according to the invention on an absolute as well as on a relative basis, comparative greenhouse and field tests were carried out with:

1. Known compounds whose chemical structure is most closely related to the compounds according to the invention;

2. other homologues from the field of the known compounds mentioned which have outstanding herbicidal properties;

3. commercially available herbicide compounds whose chemical structure is generally related to that of the compounds according to the invention. All compounds in the comparative tests listed below are generally defined as substituted phenyl-N-alkoxyalkyl-2-haloacetanilides. The known compounds compared are identified in the tables as follows:

A. 2'-Methoxy-6'-tert-butyl-N- (methoxymethyl) -2-chloroacetanilide (Example 18, U.S. Patents 3,442,945 and 3,547,620).

s io

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B. 2'-methoxy-6'-tert-butyl-N- (methoxymethyl) -2-bromo-acetanilide (Example 34 of U.S. Patent 3,547,620 and Example 36 of U.S. Patent 3,442,945).

C. 2 ', 6'-diethyl-N- (methoxymethyl) -2-chloroacetanilide (Example 5 of US Pat. Nos. 3,547,620 and 3,442,945; this compound is known under the name "Alachlor" and represents the active ingredient in the commercially available herbicide LASSO, registered trademark of the Monsanto Company).

D. 2'-methyl-6'-ethyl-N- (ethoxymethyl) -2-chloroacetanilide (Example 53 of US Pat. No. 3,547,620; general name "acetochlor").

E. 2 ', 6'-dimethyl-N- (isopropoxymethyl) -2-chloroacetanilide (Example 31 of U.S. Patent No. 3,547,620 and Example 33 of U.S. Patent No. 3,442,945).

F. 2'-methoxy-6'-methyl-N- (methoxyethyl) -2-chloroacetanilide (compound no. 6 of BE-PS 810 763).

G. 2'-methoxy-6'-methyl-N- (ethoxyethyl) -2-chloroacetanilide (compound no. 7 of BE-PS 810 763).

H. 2'-methoxy-6'-methyl-N- (l-methoxyprop-2-yl) -2-chloroacetanilide (compound no. 9 of BE-PS 810 763) and

I. 2'-methyl-6'-ethyl-N- (l-methoxyprop-2-yI) -2-chloroacetanilide (US Pat. No. 3,937,730; general name "Metolachlor"; this compound is the active ingredient in the commercial herbicide "Dual", registered trademark of Ciba-Geigy Corporation).

In pre-emergence herbicide tests, compounds according to the invention were compared with the known compounds A to I with regard to the control of various perennial or annual weeds, with particular attention being paid to the species which are difficult to kill and which predominantly infect such important crops as soybeans, cotton, peanuts, oilseed rape and bush beans were. The test results are summarized below.

In the following discussion of the data, reference is made to the amounts of herbicide applied, which are represented by «GR15» and «GR85»; these quantities are given in pounds per acre (lbs / A), which can be converted into kg per hectare (kg / ha) by multiplying by 1.12. GR15 defines the maximum amount of herbicide at which damage occurs in 15% or less of the crops, while GR85 is the minimum amount necessary to achieve an 85% weed inhibition. The GR15 and GRC5 amounts are used as a measure of the possible performance of commercially available products, although, of course, suitable commercial herbicides can have greater or lesser damage to plants 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 degree of harmlessness for crops and is expressed as the ratio GR15 / GRCä, d'.h. GR15 amount for the crop divided by GR05 amount for the weeds, both amounts expressed in lbs / A and kg / ha. In the tables, the selectivity factors, insofar as they are used, are given in brackets after the weeds; "NS" means "not selective"; insignificant or indeterminate selectivity is indicated by a dash after the weed, a blank indicating that the plant species was not involved in a particular test, that the data was not obtained for any reason, or was less significant than the data available; for example, shorter-term observations in favor of longer-term data are not given, or longer-term data are omitted because data for a shorter period was definitive for a specific herbicide activity.

As crop tolerance and weed control are related, a brief discussion of this relationship, expressed as a selectivity factor, is appropriate. In general, it is desirable that the harm factors for the crop be high, because higher herbicide concentrations are often desired for one reason or another.

Conversely, the quantities for weed control from economical and possibly ecological green 10 should be small, i.e. the herbicide should have a high uniform activity. However, small amounts of a herbicide may not be sufficient to control certain weeds, and a larger amount is required. The best herbicides are therefore those that control the greatest number of weeds with the least amount of application and the greatest possible harmlessness for the crop, i.e. Crop tolerance, offer. The selectivity factors (defined above) are thus used to quantify the relationship between harmlessness for the crop and control of the weeds; for the selectivity factors given in the tables: the higher the numerical value, the greater the selectivity of the herbicide for weed control in a particular crop.

25 The pre-emergence tests listed include both greenhouse and field tests. In greenhouse tests, the herbicide is either applied to the surface after planting seeds or cuttings, or it is worked into a certain amount of soil that is to be spread over test seeds in seeded test containers. In the field tests, the herbicide is incorporated into the earthfeed (P.P.I.) before planting, i.e. it is applied to the surface of the earth, then mixed with the soil, and then the crop seeds are planted out. 35 The surface test procedure used in the greenhouse is carried out as follows: Containers, e.g. Aluminum pans with about 24 X 13 X 7 cm, or plastic pots with about 9.5 X 9.5 X 8 cm, with drain holes in the bottom, are filled to the brim with Ray silt clay, the 4o d'ann up to a height of 1 , 3 cm below the edge of the pot. The pots are then sown 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 surface of the earth 45 using a belt sprayer (187 1 / ht, 2.11 kp / cm 2); other spray devices, e.g. used a De Vilbiss sprayer. Each pot is watered from above with 0.64 cm of water, then the pots are placed on greenhouse tables and watered from below as needed. In the case of an alternative process, irrigation from above can also be omitted. The effect of the herbicide is determined about 3 weeks after the treatment.

The herbicide treatment by incorporating it into the soil is carried out as follows in greenhouse tests: 55 Good topsoil is placed in aluminum pans and tapped up to 1 to 1.3 cm below the edge. A number of seeds or offshoots of various plant species are distributed to the earth. The soil necessary for completely filling the pans after sowing or planting 6o 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 mixed thoroughly and used to cover the prepared pans. After treatment, the pans are initially watered from above, which corresponds to 0.64 cm of precipitation, then they are watered from below as needed so that there is adequate moisture for germination and growth. The irrigation

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from above can also be omitted. The relative efficiency of compounds according to the invention is assessed, for example

3 weeks after sowing and treatment. with related known compounds in the fight

Table II shows the data for the herbicidal activation of yellow sedge and mercury in soybean,

vity listed in a first pre-emergence test series; compared cotton and corn crops.

TABLE II

connection

Quantity for GRss (kg / ha)

Cyperus couch grass

Soybeans

Quantity for GR15

(kg / ha) cotton

Corn

A

> 2.2

1.6

3.1 (-) 0.28 (NS)

> 2.2 (-)

0.17 0.28

(NS) (NS)

B

0.69

2.8

0.56 (NS) 1.1 (NS)

> 2.2 (> 2.0)

0.034 (NS) 0.07 (NS)

C.

0.45

0.56

1.7 (4) 1.1 (2)

0.78 0.84

(2) (1.5)

D

0.2

0.18

0.39 (1.5) 0.39 (2)

0.25 (1)

0.22 0.22

(1) (1)

E

0.17

0.21 (1)

0.48 (3)

0.09

(NS)

F

0.34

0.27

0.21 (NS) 0.21 (NS)

0.21 (NS)

<0.22 <0.22

(NS) (NS)

G

0.25

0.20

<0.07 (NS) <0.07 (NS)

0.39 (1.5)

<0.07 <0.07

(NS) (NS)

H

1.5

0.36

2.2 (1.5) 2.2 (6)

2.9 (2) 2.7 (7.5)

<1.5 1.25

(NS) (3.5)

I.

1.7

0.9

<1.7 (NS) 1.3 (1.5)

<1.7 (NS) 1.3 (1.5)

<1.7 <0.9

(NS) (NS)

Ex. 1

0.10

0.20

0.28 (3) 0.28 (1.5)

0.28 (3)

<0.07 <0.07

(NS) (NS)

Ex. 2

0.17

0.07

0.17 (1) 0.13 (2)

0.17 (1) 0.07 (1)

<0.17 <0.07

(NS) (NS)

Ex. 3

0.26

0.13

0.77 (3) 0.81 (6)

0.77 (3)

<0.26 <0.13

(NS) (NS)

Ex. 4

0.34

0.22

1.0 (3.0) 1.0 (4.5)

1.0 (3.0)

<0.34 <0.22

(NS) (NS)

Ex. 5

0.28

0.28

3.4 (12.0) 3.4 (12.0)

2.8 (10.0)

<0.28 <0.28

(NS) (NS)

Ex. 6

0.26

0.28

2.0 (8.0) 2.2 (8.0)

2.5 (10.0)

<0.26 <0.28

(NS) (NS)

Ex. 7

0.22

0.56

0.90 (4.0) 0.90 (1.6)

1.5 (6.5)

<0.15 <0.15

(NS) (NS)

Ex. 8

0.37

0.17

0.56 (1.5) 0.56 (3.3)

0.72 (1.9)

<0.13 <0.13

(NS) (NS)

Ex. 9

0.56

0.47

5.6 (10.0) 5.6 (11.9)

1.7 (3.0)

<0.28 <0.28

(NS) (NS)

Ex. 12

0.12

0.11

0.28 (2.5) 0.28 (2.5)

0.25 (2.0)

<0.12 <0.11

(NS) (NS)

Ex. 13

0.22

0.28

0.45 (2.0) 0.56 (2.0)

2.7 (12.0)

<0.22 <0.28

(NS) (NS)

Ex. 14

0.36

0.50

> 5.6 (> 15.6)> 5.6 (> 11.1)

1.4 (3.9)

5.6 5.6

(15.6) (11.1)

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From Table II it can be seen that in general the compounds according to the invention are significantly more active as a class, i.e. have a higher uniform activity towards Cy-perus esculentus and couch grass, and a higher harmlessness for soybeans and cotton than the reference compounds.

Regarding the control of Cyperas esculentus, it should be noted that each compound of the invention tested was remarkably more active than Compounds A and B, which are structurally most closely related to the reference compounds, and also as Compound H, which is less related than A and B, which in some respects can be regarded as more closely related to the compounds according to the invention than the compounds C, D, E and I. In particular it should be noted that the compound of Example 1 with a GR85 amount of 0.10 kg / ha was about twice as active as the most active reference compound E (GR85 0.17 kg / ha), while it had a harmlessness factor 3 times that of compound E for soybeans and an equivalent harmlessness for cotton. The compounds of Examples 2 and 12 according to the invention also had equivalent or greater unit activity than Compound E towards Cyperus esculentus. Although reference compounds F and G have a fairly high unit activity, none of the compounds was selective for Cyperus in soybeans, nor was compound F selective in cotton. Although Compound G controlled Cyperus in cotton, the harmlessness was less than that of all the compounds of the invention except Example 2 and markedly less than that of Examples 5, 6 and 13. The selectivity factors of the compounds of Examples 9 and 14 for Cyperus in soybeans were particularly outstanding.

Regarding the mercury control, the compound of Example 2 was almost 3 times as active as the most active reference chemical, Compound D, while achieving equivalent harmlessness to soybeans. The compound of Example 3 according to the invention had a higher unit activity against mercury and was three times as harmless to soybeans as compound D. Here, too, it should be noted that each compound tested according to the invention had an outstandingly superior unit activity compared to compounds A and B compared to mercury which are the closest related tested reference compounds. Although the unit activity of compound H against mercury was slightly higher than that of the compounds of examples 9 and 14, the selectivity factors of these latter compounds for mercury in soybeans were about twice as large as that of compound H, the most closely related reference compound. In addition, the reference compounds A, B, F and G were not selective for mercury in soybeans.

From Table II it can further be seen that of all the compounds tested, the compounds of Examples 5, 6, 9 and 14 had by far the highest harmlessness factors for soybeans relative to Cyperus and Quack. The compounds of Examples 5, 6 and 13 had by far the highest safety factors for cotton, relative to Cyperus esculentus. It should also be noted that the extraordinarily good harmlessness factors of the compounds of Examples 5, 6, 9, 13 and 14 were associated with very low amounts of GR85, which indicates a high uniform activity against cyperus and mercury. In these tests, most of the compounds according to the invention were not selective in maize, the same applies to all but three reference compounds. However, the compound of Example 14 showed an extraordinarily superior selectivity relative to mercury and Cyperus in maize.

In further comparative tests, the herbicidal pre-emergence activity of the reference compounds C and D and the compound from Example 1 was tested in various one-year broad-leafed weeds at a rate of 3.36 kg / ha. Assessment was done 6 to 7 weeks after treatment (WAT) and the percent control of weed growth was recorded. The data from this test are summarized in Table III.

TABLE III Control of annual broad-leaved weeds pre-emergence test, 6 to 7 WAT

Weed% control at 3.36 kg / ha

Compound Example 1 C D

Sida spinosa

93

35

73

Sesbania exaltata

100

0

69

Amaranthus

83

62

88

Polygonum

88

64

76

Report

75

61

81

Ambrosiaceae

72

53

43

Datura

98

68

98

From Table III, it can be seen that the compound of Example 1 exhibited superior activity compared to Compound C over any broad-leaved weed tested. Similarly, the compound of Example 1 shows markedly superior activity compared to Compound D against Sida spinosa, Sesbana exaitata, Polygonum and Ambrosaceae, while showing equivalent activity against Thorn Apple and slightly less activity against Amaranthus and Melde.

For further comparisons, field tests were carried out to determine the relative pre-emergence activity and selectivity of the compound of Example 1 compared to the reference compounds C, D, E and I for Echinochloa, Sida spinosa and Sesbania exaltata in soybeans. These tests were carried out in individual plots with Sharkey alumina, which contained 2.0% organics and was treated with various concentrations of each herbicide, which was applied as an emulsifiable concentrate at a rate of 280.6 l / ha. The assessment was carried out 4 weeks and 7 weeks after the treatment. The test data, which is based on 3 runs, show that after 7 weeks only the compound of example 1 selectively controlled Sesbania exaltata. This control (GR85) was achieved with only 1.96 kg / ha, while GR85 for each of the compounds C , E and I was 5.6 kg / ha and for compound D was 5.0 kg / ha. GRlg in soybeans was 3.9 kg / ha, which gave a 2.0-fold safety factor for compound of Example 1. In order to achieve the same GR85 value, approximately three times the amount of the compound from Example 1 was required for the reference compounds, but without selectivity in soybeans.

Compounds C and D were nonselective to Sida spinosa in soybeans at 7 WAT. 4.2 kg / ha of compound I and 2.8 kg / ha of compound E were required to achieve GR85 and 1.1 and 1.5 times the selectivity factors. Using example 1

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GRS5 with 0.8 kg / ha and a 4.7-fold selectivity factor was achieved in soybeans.

Compounds C, D and E were non-selective at 7 WAT against echinochloa in soybeans. Compound I and compound of Example 1 had practically equivalent harmlessness factors, i.e. 1.5 times compared to 1.4 times.

The field tests thus show that, with the exception of comparable control of Echinochloa by compound I, the compound of example 1 was significantly superior to the reference compounds C, D, E and I in the selective control of all three one-year-old weeds in soybeans 7 weeks after the treatment.

In further tests to determine the relative herbicidal activities and selectivities over even longer periods, the same herbicides as in the previous tests were again examined in field tests, this time in individual plots from silty clay to silty clay loam with 3.0 to 3.5 % Share of organic substances.

5 In parallel tests, emulsifiable concentrates of the respective herbicides were applied to the surface for pre-emergence control or incorporated into the soil before planting, again at 280.5 l / ha, which contained the appropriate herbicide concentration as active ingredient. In these tests, the herbicides in the control of the perennial grasshopper and the annual broad-leaved weeds Ambrosiaceae, Amaranthus and Polygonum in soybeans were compared. These tests were subjected to heavy rainfall, 4.45 cm on the fifth day after treatment ("DAT"), and 2.29 cm, 1.52 cm, 1.27 cm on the following days. The data are summarized in Table IV.

TABLE IV Pre-emergence activity

WAT compound incorporation before planting GRis amount

GR85 quantity (kg / ha) (kg / ha)

Mercury Ambrosiaceae Amaranthus Polygonum soybeans

Ex. 1 3 2.2 1.7

6 2.2 5.6 2.2 2.5 2.5

9.5 2.5> 6.7 3.4> 3.4

C 3> 6.7> 4.5

6> 6.7> 6.7> 6.7> 6.7> 4.5

9.5> 6.7> 6.7> 6.7> 4.5

D 3 5.6 3.9

6> 6.7> 6.7> 6.7 5.6 4.2

9.5 6.7> 6.7> 6.7 4.5

E 3> 6.7 2.2

6> 6.7> 6.7 4.2 4.5 2.8

9.5> 6.7> 6.7 4.5 4.2

I 3> 6.7 1.7

6> 6.7> 6.7> 6.7> 6.7 3.9

9.5> 6.7> 6.7 5.9 (5.0

Surface treatment

Ex. 1 3 2.5 1.5

6 2.5 4.5 4.5 3.4 3.4

9.5 4.5 5.0 3.4 4.8 4.2

C 3 5.9 3.9

6> 6.7> 6.7 4.5> 6.7 2.2

9.5> 6.7> 6.7 5.0 5.9> 4.5

D 3> 6.7 0.34

6> 6.7> 6.7 6.7 7.0 3.9

9.5> 6.7> 6.7 5.0 6.7 5.3

E 3 5.6 2.5

6> 6.7> 6.7 5.6 4.5 2.0

9.5> 6.7> 6.7 5.0 5.6 4.8

1 3> 6.7 4.5

6> 6.7> 6.7> 6.7> 6.7 4.5

9.5> 6.7> 6.7> 6.7> 6.7 4.5

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12

Table IV shows that when incorporated before planting, none of the reference compounds selectively controlled any of the weeds tested in soybeans at application rates of 6.7 kg / ha, the maximum test amount, 6 weeks and 9.5 weeks after treatment. As already mentioned, will! selectivity is indicated by the selectivity factor, i.e. the ratio GR15 / GR85, which gives a value of 1.0 or more; the higher the value

the greater the selectivity. The compound of Example 1, on the other hand, showed selective control of mercury, amaranthus and polygonum 6.0 WAT, and control of mercury and polygonum 9.5 WAT. The herbicidal activity of the compound of Example 1 is on the order of magnitude 3 times as large or larger than that of the reference compounds against mercury and polygonum (except Compound D), and about 2 times or more as active as the reference compounds (except Compound D 6 and 9.5 WAT and connection E 9.5 WAT). None of the herbicides selectively controlled Ambrosiaceae in this test, but the compound of Example 1 was 6 WAT more active against this weed than the reference compounds.

Also in the tests with surface application of the herbicides, none of the reference chemicals controlled one of the weeds in soybeans selectively at application rates of 6.7 kg / ha at 6 or 9.5 WAT, except for compound D in the case of amaranthus at 9.5 WAT. In these tests, selective weed control was observed for the compound of Example 1 at Mercury and Polygonum at 6 WAT, and 1 at Amaranthus at 9.5 WAT; the harmlessness factor was slightly greater than that for compound D, i.e. 1.3 times compared to 1.1 times. In these tests too, the compound from Example 1 showed a significantly higher herbicidal activity than the reference compounds.

The table shows that, based on the following criteria, namely the uniform activity against the weeds, the tolerance of the soybeans to the herbicides, the harmlessness factors and the application methods, the compound of Example 1 had significantly superior properties as a pre-emergence herbicide than the compared reference compounds.

Persistent weed control by the compound of Example 1 under heavy rainfall showed that the compound did not leach out easily.

In further comparative tests in the field, the compounds of Example 1 and the reference compounds D and E were tested for the selective control of Sida spinosa and Digitaria sanguinalis in cotton, the herbicide both being applied to the surface and incorporated into the soil before planting ; yellow sedge was included in the pre-planting test. The soil used for the tests was silt loam with 1.7% organic content. Assessment took place 2, 6 and 9 weeks after the treatment. Surface run data based on 3 runs show that Compound 1 had more than 2 times the unit activity towards Sid'a spinosa, like Compounds D and E at 6 WAT, and the like. 1.5 times their activity at 9 WAT. Compound D was not selective for Sida spinosa in cotton at 6 or 9 WAT. The selectivity factors for Compound E at 6 and 9 WAT were 1.1 and 1.3, respectively, compared to 3.3 and 1.8 for the compound of Example 1. Although the unit activities of each compound tested against Digitaria at 6 WAT were comparable, the compound of Example 1 was more active than Compound E at 9 WAT, and more selective (ie SF> 4.0) than Compound D, the SF 2.8.

In the pre-planting herbicide tests, the unit activity of the compound from Example 1 to 9 WAT was over 2 times greater than Cyperus than that of the reference chemicals, slightly less than 2 times greater than Digitaria, and more than V / t compared to Sida spinosa , times as big. In this field test, the compound of Example 1 Cyperus in cotton selectively controlled up to 6 WAT while the reference chemicals did not show selectivity even at 2 WAT. None of the test chemicals controlled Sida spinosa selectively in this PPI test, but the compound of Example 1 was significantly better than the other compounds. The compound of Example 1 and compound E controlled Digitaria just under 2 WAT, but were non-selective thereafter; Compound D was never selective for Digitaria.

The most important conclusions from the above field tests in cotton are therefore that the compound from Example 1 was significantly more active than the reference compounds against the weeds Cyperus and Sida spinosa, this activity being maintained over a longer period of time, and that the compound from Example 1 against selectivity factors superior to these weeds. Furthermore, the compound of Example 1 had superior selectivity to Digitaria in cotton at 9 WAT compared to Compound D.

Further comparative tests were carried out with the compound of Example 1 and the compounds D and E in order to determine their relative herbicidal activity and the duration of action in the soil against the perennial weeds Cyperus esculentus and) grasshopper. Compounds D and E were born the most active selective herbicides of the known 2-haloacetanilides, and were considered standards for this class in tests for other herbicides against cyperus and mercury and other weeds. In the tests discussed here, 25 Cyperus tubers and 25 pieces of mercury rhizomes were planted for 2 runs of each treatment. The herbicides were incorporated into the soil cover layer in amounts sufficient to determine the amount of GR50, i.e. the minimum amount necessary to achieve 50% weed control; 11.2 kg / ha was the maximum amount and 1.4 kg / ha the minimum fixed amount that was actually applied. Assessment took place 3, 6, 12 and 18 weeks after the treatment. After each assessment, the ground cover was removed, the old tubers and rhizome fragments removed, planted again, then placed in the greenhouse for the next cycle. The test results are summarized in Table V, “WAT” means “weeks after treatment”.

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TABLE V Duration of action in the soil

connection

GR50 kg / ha Cyperus esculentus

Couch grass

WAT

Ex. 1

<1.4

<1.4

3rd

<1.4

<1.4

6

1.4

1.4

12

8.4

11.2

18th

D

<1.4

<1.4

3rd

1.12

1.4

6

5.9

5.6

12

> 11.2

> 11.2

18th

E

<1.4

<1.4

3rd

1.4

1.7

6

7.8

11.2

12

> 11.2

> 11.2

18th

The data for the control of Cyperus in Table V show that at 3 WAT the GR50 amount of each compound was below 1.4 kg / ha, while at 6 WAT there were some crucial differences. At 12 WAT, there were significant differences in the control of Cyperus. While only 1.4 kg / ha of the compound of Example 1

to control 50% of the weed, 5.9 kg / ha of Compound D and 7.8 kg / ha of Compound E were needed to achieve the same level of control over Cyperus esculentus. At 18 WAT, only 5 8.4 kg / ha of the compound of Example 1 was required for 50% control of Cyperus, compared to an average of over 11.2 kg / ha (maximum amount used) of compounds D and E.

Likewise, the data on mercury in Table V show that at 6 WAT, the compound of Example 1 and Compound D showed slightly superior activity to Compound E. At 12 WAT, however, the extraordinary superiority of the compound from Example 1 is demonstrated by the fact that only 1.4 kg / ha are required to achieve the same control over mercury, for the compound D 5.6 kg / ha and of compound E 11.2 kg / ha are required. The superior herbicidal activity of the compound of Example 1 was also evident at 18 WAT.

20 A major advantage of a herbicide is its ability to work in a variety of soil types. Accordingly, Table VI summarizes data demonstrating the herbicidal activity of the compound of Example 1 on Cyperus in cotton and soybeans in a variety of soil types that have varying levels of organic matter and clay. The herbicides were incorporated into the soil, the seeds were planted 0.95 cm deep and irrigated from above with 0.64 cm. The assessment was carried out 18 days after the treatment.

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TABLE VI

connection

Soil type

Organic shares,%

Volume, %

GRS5 GRis

(kg / ha) (kg / ha)

Cyperus cotton soybeans

Ex. 1 Ray silt clay 1.0

Sarpy clay 2.3 Georgeville silty clay 2.9

Wabash clay 4.3 drummer silty clay 6.0

Florida sand 6.8

9.6

37.0 33.0

37.0 1.8

0.22 0.07

0.12 0.22

0.22 0.27

0.73 0.95

0.47 1.12

0.95 0.56

0.56 0.95

0.56 0.95

0.87 0.48

It can be seen from Table VI that the compound of Example 1 appears to be quite insensitive to the type of soil and the proportion of organic substances; it shows selective control of Cyperus in both cotton and 55 soybeans in soils with 1.0 to 6.8% organic matter and 1.8 to 9.6% clay. The selectivity factors were greatest in Sarpy clay.

Further tests were carried out to determine the herbicidal performance of the compound from Example 1 in soils with a large proportion of organic substances. In three repeated field tests, the activity of the compound of Example 1 against amaranthus and melde was tested in soybeans planted in black peat soil. Compounds C, D, E and I were also tested for comparative purposes. These tests were carried out with both application methods, namely incorporation into the soil or application to the surface, they were carried out in black peat soil, which contained 23% organic substances.

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14

In these tests, the compound of Example 1 showed the highest unit activity versus reporting at 4 WAT in both the P.P.I. and S.A. methods and, with the P.P.I. method, the highest selectivity factor in soybeans, i.e. H. greater than 2.7 versus 1.1 for each of compounds C and D; Compounds E and I were non-selective at 4 WAT. All compounds were non-selective for reporting at 7 WAT in neither of the two application methods; Compound E was slightly more active than the compound of Example 1 at 7 WAT in both application methods. Compared to Amaranthus, compound D had the highest unit activity and the highest selectivity factor (1.9) 7 WAT in both application methods; in the surface application process, the selectivity factor of Compound D was almost twice that of Compound of Example 1 and Compound E; no other compounds selectively controlled amaranthus at 7 WAT in either application. The compound of Example 1 (S.F. 2.0) and Compounds C and E (S.F. 1.0 each) selectively controlled 4 WAT using the P.P.I. method.

The above tests thus show that when compared to the reference compounds in black peat soil, the best selective control of reporting in soybeans is obtained when the compound of Example 1 is incorporated into the soil; this compound had the highest unit activity and selectivity factor at 4 WAT of all compounds tested. Furthermore, the compound of Example 1 selectively controlled Amaranthus up to 7 WAT using the surface method, and up to 4 WAT using the P.P.I. method. Compound D gave the best control of Amaranthus at 7 WAT with both application methods. The relative performance of the compound of Example 1 and Compound D in black peat soil should be further compared to the relative performance of these two compounds in soils that contained less organic matter, e.g. 3.0 to 3.5% in which the compound of Example 1 shows superior soil activity and lifespan along with soybean selectivity in both application methods, as seen in Table IV.

The above description emphasized the excellent herbicidal activity of the compounds according to the invention in the control of perennial weeds and annual broadleaf weeds in soybeans and cotton. Furthermore, it was mentioned above and occasionally shown, e.g. in tests with Echinochloa and Digitaria that the compounds according to the invention also have an excellent herbicidal activity against annual narrow-leafed weeds, i.e. Own grasses. Indeed, compounds of the present invention, as will be illustrated below with respect to certain annual grasses, clearly demonstrate superiority over the most herbicidally active and / or commercially available known 2-haloacetanilides. The test data show cases in which a related known 2-haloacetanilide shows superior herbicidal activity under comparable conditions in comparison with compounds according to the invention in relation to certain annual weeds under comparable conditions. However, it is also evident from the comparative tests available here that compounds according to the invention are at least comparable and frequently superior to the best 2-haloacetanilides as selective herbicides for controlling annual and perennial narrow-leafed weeds in soybeans, cotton, peanuts and other crops, sometimes in an outstanding manner.

In a pre-emergence test in the greenhouse, the compounds of Examples 1 and 11 with the compounds C and E (both of which are commercially available 2-haloacetanilides) were tested for their relative herbicidal activity against annual narrow-leaved weeds, i.e. Grasses 35 tested in soybeans. In this test, the herbicides were incorporated into the soil before the seeds were planted, and the observation was made and recorded 17 days after the treatment; the test data are summarized in Table VII and represent the average of 40 2 runs.

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TABLE VII

connection

Sorghum h. Seedlings

Sorghum bicolor

GRss quantity (kg / ha)

Panicum Brachiaria miliaceum

Oryza. sativa

Rottboellia exaltata

GRi5 quantity (kg / ha)

Soybeans

Ex. 1

0.14

0.84

0.28 0.56

0.95

0.84

-1.1

Ex. 11

0.28

0.28

0.14 0.56

1.1

0.28

> 1.1

C.

0.56

0.28

0.28 0.56

1.1

1.1

> 1.1

I.

1.1

1.1

0.56> 1.1

> 1.1

> 1.1

> 1.1

When considering the data in Table VII, the following main points should be noted:

1) Compound I showed the lowest unit activity and 60 selectivity of all compounds to each tested

Weed, and showed no selectivity in soybeans for Panicum miliaceum, Oryza sativa or Rottboellia;

2) Compound C was as active as the more active compounds of Examples 1 and 11 against sorghum

65 bicolor and Panicum miliaceum;

3) the compounds of Examples 1 and 11 were both superior to the known compounds in Sorghum halepense-Säm-lingen and Rottboellia and

15

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4) the compound of Example 11 was more active against Brachiaria pl. And the compound of Example 1 was more active against Oryza s. than the known compounds.

On the basis of the comparative data from Table VII, it can be said that one or the other or both compounds according to the invention were herbicidally active against two one-year-old narrow-leafed weeds (Sorghum bicolor and Panicum miliaceum) like the best known reference compounds, and clearly better against four narrow-leafed weeds ( Halepense sorghum seedlings, Brachiaria plantaginea, Oryza sativa and Rottboellia exaltata).

Particularly noteworthy is the excellent unit activity of the compound of Example 1 against sorghum halepense seedlings (GRS5 = 0.14 kg / ha), which gives an excellent selectivity factor of about 8.0 in soybeans compared to a selectivity factor of> 2.0 for Compound C, which is the better of the known compounds tested. Similarly, the compound of Example 11 showed excellent unit activity against Brachiaria pl. and Rottboellia e., with selectivity factors of> 8.0 and> 4.0 in soybeans, respectively, compared with corresponding selectivity factors of> 4.0 and> 1.0 for compound C.

Another test was carried out on soybeans, in addition to the other annual grasses mentioned in the previous test, io Texas and Fall panicum seeds were also used. In this test, the compounds of Examples 1 and 12 were compared in terms of their herbicidal pre-emergence activity with the known compounds C, D and I. The herbicides were incorporated into the soil and irrigated from below as needed. The maximum amount of herbicide used in this test was 1.2 kg / ha, the exact amounts of GR85 and GRi5 over 1.2 kg / ha are therefore to some extent indefinite. Assessment was carried out two weeks after treatment, the data of this test are summarized in Table VIII 20.

TABLE VIII

Grs5 amount GRir. Amount

(kg / ha) (kg / ha)

connection

Panicum tex.

Sorghum h.

Sorghum bicolor

Bracharia pl.

Panicum m.

Autumn panicum

Oryza sativa

Rottboellia e.

Soybeans

Ex. 1

1.1

<0.07

0.14

0.56

0.56

<0.07

0.28

0.56

> 1.1

Ex. 12

0.28

<0.07

0.14

0.14

0.56

<0.07

0.21

0.07

> 1.1

C.

0.56

0.07

0.28

0.56

1.1

<0.07

0.28

> 1.1

> 1.1

D

0.14

0.07

0.28

0.07

0.56

<0.07

<0.07

0.56

1.1

I.

> 1.1

0.28

0.50

0.50

1.1

<0.07

0.56

0.84

> 1.1

An analysis of Table VIII shows that the compounds of Examples 1 and 12 according to the invention had the highest unit activities and selectivities of all compounds tested against Sorghum halepense and Sorghum bicolor; the compound of Example 12 had the highest activity and selectivity towards Rottboellia, and 45 the compounds of Examples 1 and 12 had the highest activities towards Panicum miliaceum together with Compound D, and against Herbstpanicum together with each of the known compounds. However, the compounds according to the invention were more selective in soybeans than compound D with respect to Panicum miliaceum. The compound of Example 12 was also the second most active compound against Panicum texanum and Oryza sativa, and the compound of Example 1 together with Compound D had the second highest activity against Rottboellia. Compound D was the most active test compound against Panicum texanum, Brachiaria p. and Oryza sativa.

The foregoing comparative data on herbicidal activity against other grasses therefore show that the compounds according to the invention have a herbicidal activity which is superior to that of the leading related compounds compared to certain annual grasses, e.g. against Echinochloa, Digitaria (S.I.), Sorghum bicolor and Rottboellia, and that they have an equivalent or, in general, comparable herbicidal activity against other weeds, e.g. against Digitaria (S.A.), Panicum species, Brachiaria and Oryza sativa.

Other greenhouse and / or field tests found selective

645 878

16

In a greenhouse test, the herbicidal pre-emergence activity of the compounds from Examples 11 and 12 was tested, namely, incorporated into the soil, against mercury in rapeseed, bush beans, sorghum and! Wheat. Both tested compounds selectively controlled mercury in oilseed rape and bush beans, the selectivity factor of the compound from Example 11 was 3.5 in both cultures, that of the compound from Example 12 3.0 in both cultures. In this test, both compounds were not selective for mercury in sorghum and wheat.

In separate greenhouse tests, the compound of Example 1 was also tested for its herbicidal activity against yellow sedge grass or mercury in rapeseed, peanuts, sugar beet, sorghum, wheat and barley; the herbicide 15 was worked into the soil. In these tests, compound D was used as a reference compound against mercury and compound E as a reference compound against yellow sedge. In the test with couch grass the assessment was carried out 19 days after treatment (DAT), in the test 20 with yellow sedge 18 DAT; the test data are summarized in Table IX; the selectivity factors for the herbicides are given in brackets after the GR15 amounts for the respective crops.

TABLE IX

weed

Culture

GRss (kg / ha)

GRÄ (kg / ha)

connection

Couch grass

peanuts

Rapeseed

Sugar beet

Sorghum

wheat

barley

Ex. 1

0.045

0.28 (6.0)

0.13 (3.0)

0.28 (6.0)

<0.034 (NS)

0.06 (1.0)

0.07 (1.5)

D

0.034

0.034 (1.0)

0.06 (1.5)

0.06 (1.5)

<0.034 (NS)

0.034 (1.0)

0.11 (3.0)

Cyperus esculentus

Ex. 1

0.12

0.87 (7.0)

0.48 (4.0)

0.022 (NS)

0.13 (1.0)

0.13 (1.0)

0.28 (2.0)

E

0.12

0.95 (8.0)

0.87 (7.0)

0.022 (NS)

0.011 (NS)

0.045 (NS)

0.13 (1.0)

Control by the compounds according to the invention of further weed species in soybeans, cotton and / or other crops. For example, the compound of Example 1 selective control over purple sedge and Se-taria faberi in cotton, and Setaria faberi and Abutilon th. in soybeans. Compared to known related acetanilide herbicides, the compound of Example 1 showed an improved suppression of weeds which are as resistant as Ambrosiaceae, Ipomoea and Xanthium. Other weeds against which the compounds according to the invention have proven to be herbicidally active include Ak-kerkratzdistel, field winch, fluffy trespe, bindweed etc.

As already mentioned, the compounds according to the invention have proven to be effective herbicides in a large number of crops. The above discussion and test data above focused primarily on weed control in soybeans and cotton, crops of particular interest here. Further tests have shown the usefulness of the compounds according to the invention in other cultures as well.

45 From Table IX it can be seen that the compound of Example 1 and Compound D both selectively controlled mercury in peanuts, oilseed rape, sugar beet, wheat and barley, but the selectivity factor of the compound of Example 1 was significantly higher than that of Compound 50 D. in peanuts, rapeseed and sugar beet, equivalent in wheat and less in barley. The compound of Example 1 selectively controlled Cyperus esculentus in the crops tested except sugar beet, while Compound E did not selectively control Cyperus in sugar beet, sorghum or wheat.

The high unit activity of compounds D and E appearing in Table IX is characteristic of the short-term greenhouse performance (i.e. 2 to 6 weeks) for these compounds against mercury and Cyperus esculentus. However, with 60 relevant test data from both greenhouse and field tests,

that the compound of Example 1 over Compounds D and E has a uniformly superior unit activity over Mercury and Cyperus and a superior selectivity in cultures for much longer periods of time. In this context, reference is again made to:

1) Table IV, which compares data from field tests up to 9.5 weeks for the performance of these compounds

17th

645878

Contains mercury and other weeds in soybeans; (Neither compound D nor compound E controlled mercury ■ in soybeans selectively even at 3 WAT);

2) the above discussion of comparative data from field tests for the performance of these compounds against Cyperus esculentus and other weeds in cotton up to 9 weeks (neither compound D nor E controlled Cyperus selectively in cotton even at 2 WAT); and

3) Table V, which contains comparative data for the duration of action in the soil of the compound of Example 1 and of the compounds D and E against Cyperus and Quack for 3, 6, 12 and 18 weeks.

The compound of Example 1 showed unit activities which were higher than those of the compounds D and E at 3 WAT (by several orders of magnitude in the observation 12 WAT) and by an undetermined value in the observation 18 WAT. It should also be noted here that the combination of superior unit activity, duration of action in soil, and selectivity in crops of the compound of Example 1 compared to Compounds D and E over Cyperus and Quecke also for the relative performance of these compounds in many other weeds applies, especially sorghum hale-pense seedlings, Sesbania exaltata, Sida spinosa, Polygonum, Melde etc.

In a multi-crop test, the pre-emergence activity of the compound of Example 1 was further tested in the field against certain annual weeds in multiple crops.

In parallel tests, the herbicides were either applied to the surface or worked into the soil before planting. Assessment and recording of the data is done 33 days after treatment in the tests with incorporation into the soil before planting, and 34 days after treatment in the tests with application of the herbicide to the surface. In both tests, the compound of Example 1 selectively controlled Echinochloa and Setaria viridia in corn, soybeans, cotton, bush beans and peanuts; Reporting was also checked in soybeans. In the P.P.I. tests, Echinochloa and Setaria were also selectively controlled in sorghum and sweet corn.

It follows from the preceding detailed description that the compounds according to the invention showed unexpectedly and outstandingly superior herbicidal properties, both absolutely and in comparison with the structurally most closely related compounds, other related homologues and analogs, and known commercial 2-haloacetanilides. In particular, the compounds according to the invention showed excellent uniform activity, duration of action in the soil and harmlessness of the crops in combating perennial and 1-year broadleaf and narrow-leaved weeds in soybeans, cotton, peanuts, rape, bush beans and other crops. In particular, the compounds according to the invention showed superior herbicidal activity against the perennial weeds Cyperus esculentus and Quecke (Agropyrum repens); annual broad-leaved weeds such as Sesbania exaltata, Sida spinosa, Chenopodium album and Polygonum, and annual narrow-leafed weeds such as Echinochloa crus-galli, Digitaria san-guinalis (P.P.I.), Sorghum bicolor and Rottboellia exaltata. In addition, the compounds according to the invention proved to be generally comparable with the best known compounds for the control of other annual grasses such as sorghum halepense seedlings, Digitaria (SA), the foxtails, Panicum species, Brachiaria planta-ginea and Oryza sativa, and annuals broad-leaved weeds such as Amaranithus and Datura stramonium. Finally, the compounds according to the invention showed increased activity in suppressing resistant annual broad-leaved weeds such as Ipomoea, Xantrium, pensylvanicum, Ambrosiaceae and Abutilon theophrasti.

Toxicological studies on the compound of Example 1 showed that the compound is fairly harmless. It was slightly toxic when taken orally (single dose of oral LD50 - 2600 mg / kg), slightly toxic when used once (dermal LD50 - 5010 mg / kg), it also produced a slight eye and eye! Skin irritation. Special handling procedures beyond the normal precautionary measures are not considered necessary.

The herbicidal preparations according to the invention, including the concentrates, which have to be diluted before use, contain at least one active ingredient and one adjuvant in liquid or solid form. The preparations are prepared by mixing the active ingredient with an adjuvant, which includes diluents, extenders, carriers and conditioning agents, so that preparations are produced in the form of finely divided solid particles, granules, pellets, solutions, dispersions or emulsions. The active ingredient can thus 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.

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 make a particular preparation readily dispersible in water or oil. The inclusion of a surface-active agent in the preparations significantly promotes their effectiveness. The term “surface-active agent” includes wetting agents, dispersing agents, suspending agents and emulsifying agents. Anionic, cationic and nonionic agents1 can be used equally.

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, especially polyphenylene phenol derivatives (ditertyl phenol derivatives), ditertyl phenol derivatives, and nonylphenol) and polyoxyethylene derivatives of the higher fatty acid monoesters of hexitol anhydrides (eg sorbitan). Preferred dispersants are methyl cellulose, polyvinyl alcohol, sodium ligninsulfonates, polymeric alkylnaphthalenesulfonates, sodium naphthalenesulfonate, and also polyethylene bisnaphthalenesulfonate.

Wettable powders are water-dispersible preparations which contain one or more active ingredients, an inert stretch solids and one or more wetting and dispersing agents. The inert stretch solids are usually of mineral origin, e.g. natural clays, diatomaceous earth and synthetic minerals made of silica and the like. Such extenders include kaolinites, attapulgite clay and synthetic magnesium silicate. Which he-. Wettable powders according to the invention usually contain about 0.5 to 60 parts (preferably 5 to 20 parts) of 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 dispersant and 5 to about 95 parts (preferably 5 to 50 parts) of inert stretch solids, all parts being based on the weight of the entire preparation. If necessary, about 0.1 to

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

1

18th

645878

2 portions of the inert stretch solids can be replaced with a corrosion or foam inhibitor, or both.

Other formulations contain dust concentrates which contain 0.1 to 60% by weight of active ingredient on a suitable extender; these dusts can be diluted for use with concentrations of about 0.1 to 10% by weight.

Aqueous suspensions or emulsions can be prepared by stirring an aqueous mixture of a water-insoluble active ingredient and an emulsifying agent until uniform and then homogenizing it to give a stable emulsion of very 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, the upper limit being determined by the solubility limit of the active ingredient in the solvent.

In another type of aqueous suspension, a water-immiscible herbicide is encapsulated, so that a microcapsule phase dispersed in an aqueous phase is formed. In one embodiment, very small capsules are formed by combining an aqueous phase containing a lignin sulfonate emulsifier, a water-immiscible chemical and polymethylene polyphenyl isocyanate that disperses the 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, so that the microcapsules are formed. In general, the concentration of the encapsulated material is about 480 to 700 g / liter, preferably 480 to 600 g / liter of the entire preparation.

Concentrates are usually solutions of active ingredient in water immiscible or only partially miscible solvents, together with a surfactant. Suitable solvents for the active ingredient according to the invention include Dimethyl formide, dimethyl sulfoxide, N-methylpyrrolidone, hydrocarbons and water-immiscible ethers, esters or ketones. However, other strong liquid concentrates can also be obtained by dissolving the active ingredient in a solvent and then diluting it 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 parts by weight and based on the total weight of the emulsifiable oil.

Granules are physically stable, particulate preparations which contain an active ingredient which adheres to or is distributed in a matrix of inert, finely divided, particulate excipient. In order to support the leaching out of the active ingredient from the particles, a surface-active agent, as listed above, can be present in the preparation. Natural clays, pyrophyllite, illite and vermiculite 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. These extenders are sprayed or mixed with the active ingredient to produce the herbicidal granules.

The granule preparations according to the invention can 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 clay particles.

The preparations according to the invention can also contain other additives, e.g. Fertilizers, other herbicides or pesticides, protective substances and the like, which are used as adjuvants or in combination with one of the above-mentioned adjuvants. Chemicals that can be used in combination with active substances according to the invention include Triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic acid or phenol derivatives, thiol carbamates, triazoles, benzoic acids, nitriles, biphenyl 15 ether and the like, such as:

Heterocyclic nitrogen / sulfur derivatives 2-chloro-4-ethylamino-6-isopropylamino-s-triazine 20 2-chloro-4,6-bis- (isopropylamino) -s-triazine

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

3-isopropyl-lH-2, l, 3-benzothiadiazin-4- (3H) -on-2,2-dioxide 3-amino-l, 2,4-triazoI

6,7-Dihydlrodipyrido- (1,2-a: 2 ', l'-c) -pyrazidiinium salt 25 5-bromo-3-isopropyl-6-methyluracil 1,1' -dimethyl-4,4'-bipyridinium.

Ureas

N '- (4-chlorophenoxy) phenyl-N, N-dimethylurea 30 N, N-dimethyl-N' - (3-chloro-4-methylphenyl) urea 3 - (3,4-dichlorophenyl) -1.1 -dimethylurea

1,3-Dimethyl-3- (2-benzothiazolyl) urea 3- (p-chlorophenyl) -l, l-dimethylurea

1-butyl-3- (3,4-dichlorophenyl) -1-methylurea

35

Carbamates / thiol carbamates

2-chloroallyldiethyldithiocarbamate S- (4-chlorobenzyl) -N, N-diethylthiolcarbamate isopropyl-N- (3-chlorophenyl) carbamate

40 S-2,3-dichloroalyl-N, N-diisopropylthiolcarbamate ethyl-N, N-dipropylthiolcarbamate S-propyldipropylthiolcarbamat

Acetamide / A cetanilide / Aniline / A mi de 45 2-ChIor-N, N-dia! Iyiacetamide

N, N-dimethyl-2,2jd! Iphenylacetamide N- (2,4-dimethyl-5 - {[(trifluoromethyl) -sulfonyl] -amino} -phe-

nyl) -acetamide N-isopropyl-2-chloroacetanilide 50 2 ', 6'-diethyl-N-methoxymethyI-2-chloroacetanilide

2'-Methyl-6'-ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide a, a, a-trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine

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

55 acids / esters / alcohols

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

2,4-dichlorophenoxyacetic acid

Methyl 2- [4- (2,4-dichlorophenoxy) phenoxy] propionate 60 3-amino-2,5-dichlorobenzoic acid 2-methoxy-3,6-dichlorobenzoic acid 2,3,6-trichlorophenylacetic acid N-1-naphthylphthalamic acid

Sodium atrium 5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitro-65 benzoate

4,6-dinitro-o-sec-butylphenol

N- (PhosphonomethyI) -glycine and its Cr6 monoalkylamine and alkali metal salts and combinations thereof

19th

645878

Ether

2,4-dichlorophenyl-4-nitrophenyl ether

2-chloro-sc, a, a-trifluoro-p-toIyl-3-ethoxy-4-nitrodiplienylether other

2,6-dichlorobenzonitrile

Monosodium methane arsonate

Disodium methanarsonate.

Fertilizers that can be used in combination with the active ingredients are e.g. Ammonium nitrate, urea, potash and superphosphate. Other useful additives include Substances in which plant organisms are rooted and grow, e.g. Compost, manure, humus, sand and the like

Various exemplary embodiments are given below for herbicide preparations of the type described above.

io B.

15

I. Emulsifiable concentrates

A. Compound of Example No. 1 calcium dodecylbenzenesulfonate / polyoxyethylene ether mixture (e.g. Atlox 3437F and Atlox 3438F) monochlorobenzene

B. Connection of Example No. 12

Calcium dodecyl sulfonate / alkylaryl polyether alcohol mixture C9 aromatic hydrocarbon solvent

C. Compound of Example No. 13

Calcium dodecylbenzenesulfonate / polyoxy

ethylene ether mixture

(e.g. Atlox 3437F)

Xylene

II. Liquid concentrates

A. Compound of Example No. 1 xylene

B. Compound of Example No. 2 dimethyl sulfoxide

C. Compound of Example No. 3 N-methylpyrrolidone

D. Compound of Example No. 4 Ethoxylated Castor Oil Rhodamine B Dimethylformamide

Wt% 50.0

20th

5.0 45.0

100.0

85.0

4.0

11.0

100.0

5.0

25th

B.

30th

35

III. Emulsions

Compound of Example No. 1 polyoxyethylene / polyoxypropylene block copolymer with butanol (e.g. Tergitol XH) water

Compound of Example No. 5 polyoxyethylene / polyoxypropylene block copolymer with butanol water

IV. Wettable powders

Compound of Example No. 1 N atrium lignosulfonate N atrium-N -methyl-N-oleyltaurate Amorphous silica (synthetic)

Compound of Example No. 6 Sodium Dioctylsulfosuccinate Calcium Lignosulfonate Amorphous Silica (Synthetic)

Compound of Example No. 7 sodium atrium lignosulfonate sodium atrium-N-methyl-N-oleyl taurate kaolinite clay

1.0 94.0

40

A.

100.0

Wt% 10.0 90.0

100.0

85.0 15.0

100.0

50.0 50.0

100.0

5.0 20.0 0.5 74.5

45

B.

50

C.

55

D.

60

65 A.

V. dusts

Compound of Example No. 1 Attapulgite

Compound of Example No. 8 Montmorillonite

Compound of Example No. 9 Bentonite

Compound of Example No. 11 diatomaceous earth

VI. Granule

Compound of Example No. 1 Granulated Attapulgite (20/40 Sieve)

% By weight 40.0

4.0 56.0

100.0

5.0

3.5 91.5

100.0

Wt% 25.0 3.0 1.0 71.0

100.0

80.00 1.25 2.75 16.00

100.00

10.0 3.0 1.0 86.0

100.0

Wt% 2.0 98.0

100.0

60.0 40.0

100.0

30.0 70.0

100.0

1.0 99.0

100.0

Wt% 15.0 85.0

100.0

100.0

645878

20th

% By weight

B. Compound of Example No. 12 30.0 Diatomaceous Earth (20/40) 70.0

100.0

C. Compound of Example No. 13 0.5 bentonite (20/40) 99.5

100.0

D. Compound of Example No. 14 5.0 pyrophyllite (20/40) 95.5

100.0

VII. Microcapsules

% By weight

A. Compound of Example No. 1

encapsulated in polyurea shell 49.2

Sodium lignosulfonate (e.g. Reax 88 B) 0.9

Water 49.9

100.0

B. Connection of Example No. 12

encapsulated in polyurea shell 10.0

Potassium lignosulfonate (e.g. Reax C-21) 0.5

Water 89.5

100.0

C. Compound of Example No. 13

encapsulated in polyurea shell 80.0

Magnesium salt of lignosulfate

(Treax 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 aqueous media. Applying 5 the preparations as liquids and! Solid particles on the earth can be done using conventional methods, e.g. with motor atomizers, tank and hand sprayers or spray atomizers. Because of their effectiveness, the preparations can also be distributed in small doses by aircraft as io 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 location of the undesired weeds is essential and critical for the application according to the invention. The exact amount of active ingredient to be used depends on various factors, e.g. of 20 of the plant species and their stage of development, type and condition of the soil, the amount of rain and the specific acetanilide used. For selective pre-emergence application on plants or soil, an application rate of 0.02 to 11.2 kg / ha, preferably of about 25 0.04 to 5.60 kg / ha, or 1.12 to 5.6 kg / ha is usually used. ha used acetanilide. In some cases, larger or smaller quantities may be required. Those skilled in the art can easily determine the optimal amount for each case from the description, including the examples. 30 The term “soil” is used in the broadest sense of the word and includes all the usual types of soil, as defined under “soils” in Webster's New International Dictio-nary, Second Edition, Unabridged (1961). The term therefore refers to any substance or medium in which plants can root and grow, and includes not only soil, but also compost, manure, manure, humus, sand and the like, which can maintain plant growth.

v

Claims (45)

645878 2nd PATENT CLAIMS 1. Compounds of the formula OR wherein R ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclo- propylmethyl, allyl or propargyl, Rj is methyl, ethyl, n-propyl or isopropyl and R2 is hydrogen, methyl or ethyl, with the proviso that if R represents hydrogen, R represents ethyl and R represents allyl if R2 is ethyl, Rj is methyl and R is isopropyl if Rj denotes methyl, R represents ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl, if Rj denotes ethyl, R represents sec-butyl, allyl or propargyl, if R! n-propyl means, R represents ethyl, and if Rj is isopropyl, R represents ethyl or n-propyl. 2. Compound according to claim 1, characterized in that it is 2'-methoxy-6'-methyl-N- (isopropoxymethyl) -2 - chloroacetanilide. 3. A compound according to claim 1, characterized in that it is 2'-methoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 4. A compound according to claim 1, characterized in that it is 2'-methoxy-6'-methyl-N- (l-methylpropoxyme-methyl) -2-chloroacetanilide. 5. A compound according to claim 1, characterized in that it is 2, -ethoxy-6'-methyl-N- (allyloxymethyl) -2-chloroacetanilide. 6. Compound according to spoke 1, characterized in that it is 2'-ethoxy-6'-methyl-N- (propargyloxymethyl) -2 - chloroacetanilide. 7. Compound according to spoke 1, characterized in that it is 2'-ethoxy-6'-methyl-N- (l-methylpropoxyme-methyl) -2-chloroacetanilide. 8. A compound according to claim 1, characterized in that it is 2'-n-propoxy-6'-methyl-N- (ethoxymethyl) -2 - chloroacetanilide. 9. A compound according to claim 1, characterized in that it is 2'-isopropoxy-6'-methyl-N- (ethoxymethyl) -2 - chloroacetanilide. 10. A compound according to claim 1, characterized in that it is 2'-isopropoxy-6'-methyl-N- (n-propoxymethyl) -2-chloroacetaniIid. 11. A compound according to claim 1, characterized in that it is 2'-ethoxy-N- (allyIoxymethyl) -2-chloroacetanilide. 12. A compound according to claim 1, characterized in that it is 2'-methoxy-6'-ethyl-N- (isopropoxymethyl) -2 - chloroacetanilide. 13. Herbicide preparation, characterized in that it is an adjuvant and a herbicidally effective amount of a compound of the formula 0 II OR contains what R ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl, Rj is methyl, ethyl, n-propyl or isopropyl and R2 is hydrogen, methyl or ethyl, with the proviso that if R2 is hydrogen, Rt is ethyl and R is allyl if R2 is ethyl, R is ^ methyl and 'R is isopropyl when Ri is methyl, R is ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl when. Rj is ethyl, R is sec-butyl, allyl or propargyl when Rj represents n-propyl, R represents ethyl, and when Rt represents isopropyl, R represents ethyl or n-propyl. 14. Preparation according to claim 13, characterized in that the compound is 2'-methoxy-6'-methyl-N- (iso-propoxymethyl) -2-chloroacetanilide. 15. Preparation according to claim 13, characterized in that the compound is 2'-methoxy-6'-methyl-N - (ethoxymethyl) -2-chloroacetanilide. 16. Preparation according to claim 13, characterized in that the compound is 2'-methoxy-6'-methyl-N- (l - methylpropoxymethyl) -2-chloroacetanilide. 17. Preparation according to claim 13, characterized in that the compound is 2'-ethoxy-6'-methyl-N- (allyl-oxymethyl) -2-chloroacetanilide. 18. Preparation according to claim 13, characterized in that the compound is 2'-ethoxy-6'-methyl-N- (pro-pargyIoxymethyl) -2-chloroacetanilide. 19. Preparation according to claim 13, characterized in that the compound is 2'-ethoxy-6'-methyl-N- (l - methylpropoxymethyl) -2-chloroacetanilide. 20. Preparation according to claim 13, characterized in that the compound is 2'-n-propoxy-6'-methyl-N - (ethoxymethyI) -2-chloroacetani! Id. 21. Preparation according to claim 13, characterized in that the compound is 2'-isopropoxy-6'-methyl-N - (ethoxymethyl) -2-chloroacetanilide. 22. Preparation according to spoke 13, characterized in that the compound is 2'-isopropoxy-6'-methyl-N - (n-propoxymethyl) -2-chloroacetanilide. 23. Preparation according to spoke 13, characterized in that the compound is 2'-ethoxy-N- (alIyloxymethyl) - 2-chloroacetanilide. 24. Preparation according to claim 13, characterized in that the compound is 2'-methoxy-6'-ethyl-N- (iso-propoxymethyl) -2-chloroacetanilide. 25. A method for controlling unwanted plants in crops, characterized in that 5 10th 15 20th 25th 30th 35 40 45 50 55 60 65 3rd 645878 on the location of the plants a herbicidally effective amount of a compound of the formula OR brings up what R ethyl, n-propyl, isopropyl, isobutyl, sec-butyl, cyclopropylmethyl, allyl or propargyl, Rj is methyl, ethyl, n-propyl or isopropyl and R2 is hydrogen, methyl or ethyl, with the proviso that if R2 is hydrogen, Rx is ethyl and R is allyl when t R2 is ethyl, Rx is methyl and R is isopropyl if Ri represents methyl, R represents ethyl, isopropyl, isobutyl, sec-butyl or cyclopropylmethyl, if Ri denotes ethyl, R represents sec-butyl, allyl or propargyl, if Rj represents n-propyl, R represents ethyl, and when Rj represents isopropyl, R represents ethyl or n-propyl. 26. The method according to claim 25, characterized in that the compound is 2'-methoxy-6'-methyl-N- (iso-propoxymethyl) -2-chloroacetanilide. 27. The method according to claim 25, characterized in that the compound is 2'-methoxy-6'-methyl-N - (ethoxymethyl) -2-ch! Oracetanilide. 28. The method according to claim 25, characterized in that the compound is 2'-methoxy-6'-methyl-N- (l-methylpropoxymethyl) -2-chloroacetanilide. 29. The method according to claim 25, characterized in that the compound is 2'-ethoxy-6'-methyl-N- (allyI-oxymethyl) -2-chloroacetanilide. 30. The method according to claim 25, characterized in that the compound is 2'-ethoxy-6'-methyl-N- (pro-pargyloxymethyl) -2-chloroacetanilide. 31. The method according to claim 25, characterized in that the compound is 2'-ethoxy-6'-methyl-N- (l-methylpropoxymethyl) -2-chloroacetanilide. 32. The method according to claim 25, characterized in that the compound is 2'-n-propoxy-6'-methyl-N - (ethoxymethyl) -2-chloroacetanilide. 33. The method according to claim 25, characterized in that the compound is 2'-isopropoxy-6'-methyl-N - (ethoxymethyI) -2-chloroacetanilide. 34. The method according to claim 25, characterized in that the compound is 2'-ethoxy-N- (aIlyloxymethyI) - 2-chloroacetanilide. 35. The method according to claim 25, characterized in that the compound is 2'-methoxy-6'-ethyl-N- (isopropoxy-methyl) -2-chloroacetanilide. 36. The method according to claim 25, characterized in that the crop plants are soybeans, cotton, peanuts, rape, bush beans, sugar beet, sorghum, wheat or barley1. 37. The method according to claim 36, characterized in that the undesirable plants are perennial grasses and sedge grasses as well as annual weeds. 38. The method according to claim 37, characterized in that the perennial weeds are grasshopper (Agro-pyrum repens) and Cyperus esculentus. 39. The method according to claim 37, characterized in that the annual weeds are broad-leaved weeds. 40. The method according to claim 39, characterized in that the broad-leaved weeds are Sida spinosa, Sesbania exaitata, Amaranthus retroflexus, Polygonum sp., Chenopodium album and Datura stramonium. 41. The method according to claim 37, characterized in that the annual weeds are grasses. 42. The method according to claim 41, characterized in that the grasses are Setaria spp., Echinochloa crus-galli, Digitaria sanguinalis, Panicum spp., Sorghum bicolor, Bra-chiaria plantaginea, Oryza sativa and Rottboellia exaltata. 43. The method according to any one of claims 36 to 42, characterized in that the compound is 2'-methoxy-6 '- methyl-N- (isopropoxymethyl) -2-chloroacetanilide. 44. The method according to claim 25 for selectively controlling the growth of weeds in soybeans, cotton, peanuts, rapeseed, kidney beans, sugar beet, sorghum, wheat or barley, characterized in that a herbicidally effective amount of 2'- Methoxy-6'-methyl-N- (isopropoxymethyl) -2 - chloroacetanilide. 45. The method of claim 25 for suppressing the weed population of Ambrosiaceae, Ipomoea sp., Xanthium pensylvanicum and Abutilon theophrasti, characterized in that a herbicidally effective amount of 2'-methoxy-6'-methyl-N - (Iso-propoxymethyl) -2-chloroacetanilide.