CH644584A5 - HERBICIDE EFFECTIVE 2-HALOGEN ACETANILIDES. - Google Patents

Description

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

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

The compounds according to the invention which are characterized by an alkoxymethyl or alkenyloxymethyl radical on the anilide nitrogen, an alkoxy radical in one ortho position and a specific alkyl radical in the other ortho position most closely correspond, 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-methoxy-methyl-6'-methoxyacetanilide and their bromo analog (cf. examples 18 and 34 in US Pat. No. 3,547 620 and Examples 18 and 36 in U.S. Patent 3,442,945).

In U.S. Patents 4,070,389 and 4,152,137, general formulas are presented which include 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; 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 with 2 or more carbon atoms between the anilide nitrogen atom and the oxygen atom of the alkoxy moiety are. The closest specific representations in BE-PS 810 763 and German application 2 402 983 are compounds which have an ethoxyethyl radical on the anilide nitrogen atom, a methoxy or ethoxy radical in an ortho position, and a methyl,

Possess ethyl or isopropyl radical in the other ortho position (cf. 810 763, compounds Nos. 7, 13, 18 to 20 and 26); other less relevant homologs of these compounds are also described, e.g. Compounds Nos. 6, 9, 16 and 17, the methoxyethyl or methoxypro-

5

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35

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644584

4th

have substituted pyl radicals on the nitrogen atom, a methoxy or ethoxy radical in one ortho position and a methyl radical in the other ortho position.

US Pat. No. 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 for other homologous and analogous compounds that are less closely related in their chemical structure, e.g. compounds 6 and 9 of BE-PS 810 763. In particular, these references describe herbicidal activities against a large number of weeds, but they do not contain any data about compounds which additionally and / or at the same time are difficult to kill the narrow-leaf weeds such as Alopecurus mysuroides, Avena fatua control fluffy broth and other weeds such as yellow foxtail (Setaria lutescens), annual rye-grass, Echinochloa crus-galli and Digitaria sanguinaiis; however, BE-PS 810 763 contains data which show good control over Avena fatua and undefined species of various other weeds in sugar beet. As will be shown below, however, the compounds according to the invention have, unlike the known homologous compounds, unexpectedly superior properties as selective herbicides in sugar beet.

A 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 slightly organic soils to heavy clays and peat soils.

Another disadvantage of some known herbicides is the lack of continued weed control in heavy rains that leach the herbicides.

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 multitude of advantages which have not hitherto been combined in a single group of herbicides.

The invention provides herbicides that selectively control various weeds, particularly annual grasses, including the narrow-leaved weeds such as Alopecurus mysuroides, Avena fatua and fluffy trespe, as well as other annual grasses such as yellow foxtail, Echinochloa crus-galli, Digitaria sanguinalis, and annuals Ryegrass, especially for sugar beet.

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

The invention further relates to herbicides which are resistant to leaching in heavy rainfall. 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 ingredients, and to processes for using these herbicide preparations in certain crops.

It has now been found that a selective group of 2-haloacetanilides, which by specific combinations of alkoxymethyl or alkenyloxymethyl radicals on the anilide nitrogen atom, specific alkoxy radicals in an ortho position and a Cj_3 alkyl, i.e. Methyl, ethyl or isopropyl radical in the other ortho position are unexpectedly superior and excellent properties as sugar beet herbicides compared to known herbicides, including the closest related known homologous compounds.

An important property of the herbicide preparations according to the invention is their ability to control narrow-leaf weeds in sugar beets, in particular the species which are difficult to kill, such as Avena fatua and Alopecurus mysuroides, and less resistant species such as yellow foxtail, Echinochloa crus-galli, Digitaria sanguinalis and other harmful weeds.

The compounds according to the invention are represented by the formula

0

II

• OR

characterized in which

R represents ethyl, n-propyl, isopropyl, isobutyl, allyl or butenyl;

Rj is methyl, n-propyl, isopropyl, n-butyl, isobutyl or isoamyl and

R2 is methyl, ethyl or isopropyl, with the proviso that

when R2 is isopropyl, R is ethyl and Rx is n-butyl;

when Ra is ethyl, R is ethyl, n-propyl or allyl, and Rj is n-butyl or isobutyl;

when R is n-propyl, Rt is n-butyl or isobutyl;

when R is isopropyl, Rx is isobutyl;

when R is isobutyl, Rx is n-propyl, isopropyl, isobutyl or isoamyl and,

when R is butenyl, R is methyl.

Particularly interesting and useful compounds according to the invention are those in which, in the above formula, R is a C2_4 alkyl radical, preferably ethyl, n-propyl or allyl, Rj is a C3 or C4 alkyl, in particular n-butyl or isobutyl, and R2 is methyl or ethyl mean.

Particular compounds according to the invention are: N- (isobutoxymethyl) -2'-isopropoxy-6'-methyl-2-chloroacetanide;

N- (isobutoxymethyl) -2'-isoamyloxy-6'-methyl-2-chloroacetanilide;

N- (n-propoxymethyl) -2'-isobutoxy-6'-methyl-2-chloroacetanilide;

N- (ethoxymethyl) -2'-n-butoxy-6'-isopropyl-2-chloroacetanilide;

N- (isobutoxymethyl) -2'-isobutoxy-6'-methyl-2-chloroacetanilide;

5

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65

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644584

N- (isopropoxymethyl) -2'-isobutoxy-6'-methyl-2-chloroacetanilide;

N- (isobutoxymethyl) -2'-n-propoxy-6'-methyl-2-chloroacetanilide;

N- (2-butene-1-yloxy methyl) -2'-methoxy-6'-methyl-2-chloroacetanilide;

N- (n-propoxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanifide; N- (Allyloxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetariilide; N- (ethoxymethyl) -2'-isobutoxy-6'-ethyl-2-chloroacetanilide;

and

N- (Alyloxymethyl) -2'-isobutoxy-6'-ethyl-2-chloroacetanide.

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 appropriate primary aniline is reacted with formaldehyde to form the corresponding methylene aniline (substituted phenylazomethine), which is then reacted with a haloacetylating agent such as chloroacetyl chloride or chloroacetyl anhydride. The appropriate alcohol is then reacted to give the corresponding N-alkoxymethyl-2-chloroacetanide as the end product.

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.

Example 1 describes the use of this N-alkylation to prepare a compound according to the invention. A modified N-alkylation process is described in Example 2 for the preparation of another compound according to the invention. The modified N-alkylation process described in Example 2 provides for the in situ production of halomethyl alkyl or alkenyl ethers which are used as starting materials in the N-alkylation process.

example 1

5.6 g (0.022 mol) of 2'-isobutoxy-6'-methyl-2-chloroacetanilide, 4.75 g (0.44 mol) of chloromethyl-n-propyl ether and 2.0 g of benzyltriethylammonium chloride were added in 250 ml of methylene chloride mixed and cooled. At 15 ° C, 50 ml of 50% NaOH was added to the mixture all at once and stirred for 2 hours, then 100 ml of cold water was added. The layers were separated, washed with water, then dried over MgSO4 and evaporated with Kugelrohr, which gave 6.5 g (09% yield) of clear oil, bp s 130 ° C. at 0.04 mm Hg.

Elemental analysis for: C1VH26C1N03 (%)

calculated: C 62.28 H 7.99 Cl 10.81 found: C 62.27 H 8.01 Cl 10.81 The product was obtained as N- (n-propoxymethyl) -2'-iso-io butoxy-6 ' -methyl-2-chloroacetanilide identified.

Example 2

In this example, a modification of the N-alkylation process described in Example 1 is described. In this embodiment, the alkylating agent is made in situ, making the process more effective, economical, and simple.

6.1 g (0.05 mol) of acetyl bromide were added to a cooled mixture of 4.6 g (0.1 mol) of Etha-20 noi, 1.5 g (0.05 mol) of anhydrous paraformaldehyde and 100 ml of methylene chloride given; the mixture was stirred until all of the paraformaldehyde was dissolved. 5.1 g (0.018 mol) of 2'-n-butoxy-6'-isopropyl-2-chloro-25 acetanilide, 2.0 g of benzyltriethylammonium chloride and 40 ml of methylene chloride were then added to this mixture. The mixture was cooled to 15 ° C and 50 ml of 50% NaOH was added all at once and stirred for 2 hours. The layers were separated, washed with water, dried over MgSOé and evaporated with 30 Kugelrohr, which gave 4.6 g (77% yield) of yellow liquid, bp 125 ° C. at 0.07 mm Hg.

Elemental analysis for: C18H28CIN03 m calculated: C 63.24 H 8.26 Cl 10.37 found: C 63.23 H 8.29 Cl 10.37 35 The product was identified as N- (ethoxymethyl) -2'-n-butoxy -6 '- Isopropyl-2-chloroacetaniiide identified.

Examples 3 to 12 40 Using practically the same procedure and the same conditions as in Examples 1 or 2, but using the appropriate secondary anilide and alkylating agent as starting materials, and suitable amounts thereof, the corresponding N- (alkoxymethyl or 45 alkenyloxymethyl) -2-haloacetanilides prepared; these compounds are summarized in Table I, along with some of their material properties.

644584

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TABLE I

example

connection

formula

Kp. ° C

Elemental analysis

No.

Empirical

(mm Hg)

Ele

Calc

Found

ment net that

3rd

N- (isobutoxymethyl) -2'-isobutoxy-

CiaH28ClN03

115

C.

63.24

63.19

-6'-methyl-2-chloroacetanilide

(0.02)

H

8.26

8.30

Cl

10.37

10.38

4th

N- (isopropoxymethyl) -2'-isobutoxy-

Ci, h26cin o3

120

C.

62.28

62.26

-6'-methyl-2-chloroacetanilide

(0.03)

H

7.99

7.99

Cl

10.81

10.81

5

N- (2-butene-l-oxymethyl) -2'-methoxy-

c15h20cino3

114

C.

60.50

60.38

-6'-methyl-2-chloroacetanilide

(0.03)

H

6.77

6.83

Cl

11.91

11.85

6

N- (isobutoxymethyl) -2'-isopropoxy-

c17h26cino3

C.

62.28

62.33

-6'-methyl-2-chloroacetanilide

H

7.99

8.04

N

4.27

4.27

Cl

10.81

10.82

7

N- (isobutoxymethyl) -2'-isoamyloxy-

c19h30cino3

120

C.

64.12

63.98

-6'-methyl-2-chloroacetanilide

(0.025)

H

8.50

8.57

ci-

9.96

10.03

8th

N- (isobutoxymethyl) -2'-n-propoxy-

C17H26C1N03

127

C.

62.28

62.20

-6'-methyl-2-chloroacetanilide

(0.08)

H

7.99

8.06

Cl

10.81

10.88

9

N- (n-propoxymethyl) -2'-n-butoxy-

c18h28cino3

117

C.

63.24

63.31

-6'-ethyl-2-chloroacetanilide

(0.02)

H

8.26

8.27

Cl

10.37

10.42

10th

N- (allyloxymethyl) -2'-n-butoxy-6'-

c18h26cino3

123

C.

63.61

63.60

-ethyl-2-chloroacetanilide

(0.04)

H

7.71

• 7.74

Cl

10.43

10.42

11

N- (ethoxymethyl) -2'-isobutoxy-6'-

c17h26cino3

132

C.

62.28

62.27

-ethyl-2-chloroacetanilide 1

(0.07)

H

7.99

8.02

Cl

10.81

10.82

12

N- (allyloxymethyl) -2'-isobutoxy-6'-

c18h26cino3

124

C.

63.61

63.61

-ethyl-2-chloroacetanilide

(0.02)

H

7.71

7.71

Cl

10.43

10.45

The secondary anilides used as starting materials in the above examples are prepared by known methods, e.g. with haloacetylation of the corresponding primary amine using haloacetylating agents such as a haloacetyl halide or anhydride. The appropriate amount of the appropriate primary amine is usually dissolved in a solvent such as methylene chloride which is a base such as e.g. Contains 10% NaOH, dissolved and stirred vigorously while with a solution of the haloacetyl halide, e.g. Chloroacetyl chloride is mixed; it is from the outside e.g. Cooled 15-25 ° C. The layers are separated and the organic solvent layer washed out with water, dried and evaporated in vacuo.

The primary amines used to make the secondary anilides can also be made by known methods, e.g. by catalytic reduction of the corresponding, appropriately substituted nitro-benzene, e.g. 2-alkoxy-6-alkylnitrobenzene, in a solvent such as an alcohol, e.g. Ethanol, and using a platinum oxide catalyst.

As mentioned, the compounds according to the invention proved to be effective herbicides, especially as pre-emergence herbicides, although post-emergence activity was also shown

Could turn 45. 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 incorporated into a certain amount of soil, which is to be spread over test seeds in seeded test containers. In the field tests, the herbicide is incorporated into the soil before planting («P.P.I.»), i.e. it is applied to the surface of the earth, then incorporated, and then the crop seeds are planted out; the herbicide can also be applied to the surface ("S.A.", surface application) after the crop seeds have been planted out.

The surface test procedure used in the greenhouse («.S.A.») Is carried out as follows:

60 containers, e.g. Aluminum pans, approx. 24 X 13 X 7 cm, or plastic pots approx. 9.5 X 9.5 X 8 cm, with drain holes in the bottom, are filled to the brim with Ray Schluff clay soil, which is then up to a height of 1 , 3 cm below the edge of the pot. The 65 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 with a spray sprayer (187 liters per hectare,

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2.11 kp / cm2). 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 an alternative method, irrigation from above can also be omitted. The effect of the herbicide is determined about 3 weeks after the treatment.

The herbicide treatment by incorporation into the soil («S.I.») is carried out as follows in greenhouse tests:

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 placed on the earth. The soil required to completely fill the pans after sowing or planting 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 rain, then they are watered from below as needed so that there is adequate moisture for germination and growth. 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 tests which were carried out to determine the herbicidal pre-emergence activity of the compounds according to the invention; in these tests, the herbicides were only applied by incorporating them into the soil, irrigation was carried out only from below; on - means that the specified plant has not been tested. The herbicidal effect was assessed using a fixed scale,

which is based on the percentage damage of each plant species. The ratings are defined as follows:

% Control

rating

0-24

0

25-49

1

50-74

2nd

75-100

3rd

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

20 A.

Canada Thistle

Field scratch thistle

Cirsium arvense

B

Cocklebur

Xanthium pensylvanicum

C.

Velvetleaf

Abutilon theo-

25th

phrasti

D

Morningglory

Winds

Ipomoea sp.

E

Lambsquarters

Report

Chenopodium album

F

Smartweed

Polygonum sp.

30 G.

Yellow nutsedge

Cyperus esculentus

H

Quackgrass

Couch grass

Agropyrum repens

. I.

Johnsongrass

Sorghum halepense

J

Downy Brome fluffy brpe

Bromus tectorum

35 K.

Barnyardgrass

Echinochloa crus-galli

TABLE II

Pre-emergence test

Connection of example no.

kg / ha

A

B

c

D

Plant species E F

G

H

I.

J

K

1

11.2

3rd

1

2nd

2nd

3rd

3rd

3rd

3rd

3rd

3rd

3rd

5.6

3rd

0

2nd

2nd

3rd

2nd

3rd

3rd

3rd

3rd

3rd

2nd

11.2

1

1

2nd

2nd

3rd

3rd

3rd

3rd

3rd

3rd

3rd

5.6

0

-

2nd

1

3rd

2nd

3rd

3rd

3rd

3rd

3rd

1.12

0

-

1

0

1

1

2nd

1

0

3rd

3rd

3rd

11.2

0

0

0

3rd

2nd

3rd

3rd

3rd

1

3rd

3rd

5.6

0

0

0

0

2nd

1

1

3rd

3rd

3rd

3rd

4th

11.2

3rd

0

2nd

2nd

3rd

3rd

3rd

3rd

2nd

3rd

3rd

5.6

2nd

1

2nd

2nd

2nd

2nd

3rd

3rd

1

3rd

3rd

5

11.2

2nd

1

0

1

3rd

2nd

3rd

3rd

1

3rd

3rd

5.6

1

0

0

3rd

1

1

3rd

3rd

0

3rd

3rd

6

11.2

2nd

1

1

1

3rd

3rd

3rd

3rd

3rd

3rd

3rd

5.6

2nd

1

1

2nd

3rd

3rd

3rd

3rd

0

3rd

3rd

7

11.2

3rd

0

1

1

3rd

2nd

3rd

3rd

0

3rd

3rd

5.6

2nd

0

2nd

1

3rd

2nd

3rd

3rd

1

3rd

3rd

8th

11.2

3rd

1

0

2nd

3rd

3rd

3rd

3rd

3rd

3rd

3rd

5.6

3rd

2nd

0

2nd

3rd

3rd

3rd

3rd

3rd

3rd

3rd

9

11.2

3rd

0

0

0

2nd

1

3rd

2nd

1

3rd

3rd

5.6

3rd

1

0

0

2nd

1

3rd

2nd

0

3rd

3rd

644 584 8

TABLE II (continued)

Connection of example no.

kg / ha

A

B

c

D

Plant species E F

G

H

I.

J

K

10th

11.2

_

0

1

1

2nd

2nd

3rd

3rd

3rd

3rd

3rd

5.6

-

0

0

0

3rd

2nd

2nd

3rd

3rd

3rd

3rd

11

11.2

3rd

1

2nd

2nd

3rd

2nd

3rd

3rd

3rd

3rd

3rd

5.6

2nd

1

2nd

2nd

3rd

2nd

3rd

3rd

1

3rd

3rd

12

11.2

3rd

-

0

1

3rd

3rd

3rd

3rd

3rd

3rd

3rd

5.6

2nd

0

1

1

1

1

3rd

2nd

1

3rd

3rd

The compounds were also tested on the following plant species using the above procedure:

L

Soybean

Soybeans

M

Sugarbeet

Sugar beet

20th

N

Wheat

wheat

O

Rice

rice

P

Sorghum

Sorghum

B

Cocklebur

Xanthium pensylvanicum

25th

Q

Wild

Winch

Polygonum

Buckwheat

Knotweed oonvulvulus

D

Morningglory

Ipomoea sp.

R

Hemp sesbania

Sesbania exaltata

E

Lambsquarters

Report

Chenopodium album

30th

F

Smartweed

Polygonum sp.

C.

Velvetleaf

Abutilon theophrasti

J

Down.y brome fluffy brpe

Bromus tectorum

35

S

Panicum species

Pamcurn spp.

K

Barnyardgrass

Echinochloa crus-galli1

T

Crabgrass

Digitaria

40

sanguinalis

The results are summarized in Table III.

TABLE III Pre-emergence test

Verb, of kg / ha plant species

Example No. LMNOPBQDREF CJSKT

5.6

1

3rd

3rd

3rd

3rd

0

3rd

0

3rd

3rd

3rd

1

3rd

3rd

3rd

3rd

1.12

0

1

0

3rd

3rd

0

1

0

1

3rd

2nd

0

3rd

3rd

3rd

3rd

0.28

0

0

0

2nd

3rd

0

2nd

0

0

0

1

0

3rd

3rd

3rd

3rd

0.06

0

0

0

2nd

2nd

0

0

0

1

0

0

0

3rd

2nd

3rd

3rd

0.01

0

0

0

1

0

0

0

0

-

2nd

1

0

0

0

2nd

3rd

5.6

1

2nd

3rd

3rd

3rd

3rd

2nd

3rd

2nd

2nd

3rd

1

3rd

3rd

3rd

3rd

1.12

0

1

2nd

3rd

3rd

0

0

1

2nd

2nd

2nd

0

3rd

3rd

3rd

3rd

0.28

0

0

2nd

2nd

2nd

0

0

0

0

1

1

0

3rd

2nd

3rd

3rd

0.06

0

0

0

1

0

0

0

0

-

0

0

0

1

1

3rd

1

0.01

0

0

0

0

0

-

0

0

0

0

0

0

0

0

1

0

5.6

0

1

2nd

2nd

3rd

0

0

3rd

2nd

0

0

0

3rd

3rd

3rd

3rd

1.12

0

0

1

3rd

3rd

0

0

0

0

0

0

0

3rd

3rd

3rd

3rd

0.28

0

0

0

0

0

0

0

0

0

0

0

0

1

1

3rd

3rd

0.06

0

0

0

0

0

0

0

1

0

0

0

0

0

1

1

2nd

9

644584

TABLE III (continued)

Verb, from example no.

kg / ha

L

M

N

O

P

B

Q

Plant species D R

E

F

C.

J

S

K

T

4th

5.6

1

2nd

3rd

3rd

3rd

0

1

1

3rd

2nd

1

1

3rd

3rd

3rd

3rd

1.12

0

1

3rd

3rd

3rd

0

0

1

3rd

1

0

0

3rd

3rd

3rd

3rd

0.28

0

1

1

2nd

3rd

0

0

0

0

0

0

0

2nd

3rd

3rd

3rd

0.06

0

0

0

1

1

0

0

0

0

0

0

0

1

1

3rd

3rd

0.01

0

0

0

0

0

0

0

0

-

0

0

0

1

0

1

2nd

0.006

0

0

0

0

0

0

0

0

0

0

0

0

0

0

1

1

5

5.6

2nd

2nd

3rd

3rd

3rd

2nd

2nd

3rd

3rd

2nd

2nd

0

3rd

3rd

3rd

3rd

1.12

0

2nd

2nd

3rd

3rd

3rd

3rd

2nd

2nd

2nd

2nd

0

3rd

3rd

3rd

3rd

0.28

0

1

1

3rd

1

3rd

3rd

3rd

1

1

0

0

3rd

3rd

3rd

3rd

0.06

0

1

0

0

0

1

0

3rd

2nd

0

0

0

2nd

1

3rd

3rd

0.01

0

1

0

0

0

0

0

0

3rd

0

0

0

0

0

3rd

3rd

6

5.6

1

2nd

3rd

3rd

3rd

1

2nd

0

2nd

3rd

3rd

0

3rd

3rd

3rd

3rd

1.12

0

1

1

1

3rd

0

3rd

0

0

3rd

3rd

0

3rd

3rd

3rd

3rd

0.28

0

1

1

1

2nd

0

0

0

0

0

0

0

1

2nd

3rd

3rd

0.06

0

0

0

0

0

0

0

0

0

0

0

0

0

0

2nd

2nd

7

5.6

0

2nd

3rd

3rd

3rd

2nd

2nd

2nd

2nd

3rd

3rd

0

3rd

3rd

3rd

3rd

1.12

0

1

1

2nd

2nd

0

2nd

0

0

3rd

2nd

0

3rd

2nd

3rd

3rd

0.28

0

1

0

1

0

0

0

0

0

0

0

0

1

1

3rd

3rd

0.06

0

1

0

0

0

0

-

0

0

1

0

0

1

2nd

1

2nd

8th

5.6

2nd

2nd

3rd

3rd

3rd

2nd

2nd

2nd

3rd

3rd

3rd

0

3rd

3rd

3rd

3rd

1.12

0

1

1

1

3rd

1

2nd

1

3rd

2nd

2nd

0

3rd

3rd

3rd

3rd

0.28

0

0

0

0

1

0

0

0

1

3rd

2nd

0

1

3rd

3rd

3rd

0.06

0

1

0

0

1

-

1

0

1

0

1

0

0

0

3rd

3rd

0.01

1

0

0

0

0

1

0

0

0

0

0

0

0

0

2nd

3rd

9

5.6

1

2nd

3rd

3rd

3rd

0

3rd

1

2nd

3rd

3rd

0

3rd

3rd

3rd

-

1.12

0

0

2nd

3rd

2nd

0

2nd

0

2nd

0

1

0

3rd

3rd

3rd

-

0.28

0

0

0

1

1

0

0

0

0

0

0

0

3rd

3rd

3rd

-

0.06

0

0

0

0

0

0

0

0

0

0

0

0

1

0

3rd

-

0.01

0

0

0

0

0

0

0

0

0

0

0

0

1

0

0

-

10th

5.6

0

2nd

3rd

3rd

3rd

0

3rd

0

1

3rd

3rd

1

3rd

3rd

3rd

-

1.12

-

1

2nd

2nd

1

0

1

1

0

2nd

1

0

3rd

3rd

3rd

-

0.28

0

1

1

2nd

1

0

0

0

0

1

0

0

3rd

3rd

3rd

-

0.06

0

0

0

0

0

0

0

0

0

0

1

0

0

0

3rd

-

0.01

0

0

0

0

0

0

0

0

0

0

0

0

0

0

0

-

11

5.6

1

2nd

3rd

3rd

3rd

1

2nd

3rd

3rd

3rd

3rd

2nd

3rd

3rd

3rd

-

1.12

0

1

3rd

3rd

3rd

0

2nd

1

3rd

2nd

2nd

2nd

3rd

3rd

3rd

-

0.28

0

1

2nd

2nd

2nd

0

1

0

3rd

2nd

0

0

3rd

3rd

3rd

-

0.06

0

0

0

1

0

0

0

0

0

1

5

0

3rd

1

3rd

-

0.01

0

0

0

1

0

-

0

0

3rd

0

-

0

0

0

0

-

12

5.6

0

3rd

3rd

3rd

3rd

1

3rd

1

3rd

3rd

3rd

1

3rd

3rd

3rd

3rd

1.12

0

1

3rd

3rd

3rd

0

2nd

0

2nd

2nd

1

0

3rd

3rd

3rd

3rd

0.28

0

1

2nd

1

0

0

1

0

0

2nd

3rd

0

3rd

3rd

3rd

3rd

0.06

0

0

1

1

0

0

0

0

0

2nd

3rd

0

1

0

3rd

3rd

0.01

0

0

0

0

0

0

0

0

0

2nd

3rd

0

1

0

1

1

It has been found that the herbicides according to the invention have unexpectedly superior properties as selective pre-emergence herbicides for use in sugar beets, in particular for the selective control of narrow-leafed weeds which are difficult to kill, e.g. Alopecurus m., Avena fatua and fluffy trespe, as well as other weeds, such as yellow foxtail, annual ryegrass, Echinochloa crus-galli and Digitaria s. The selective control and suppression of the above-mentioned and other weeds with the aid of the herbicides according to the invention has been found in a large number of other crops, including soybeans, cotton, peanuts, bush beans, rape, tomatoes and cucumbers. The clearly outstanding herbicide properties of the compounds according to the invention are, however, most evident in the selective control of one-60-year-old grasses in sugar beets.

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

65

1. known homologous compounds which are chemically most closely related to the compounds according to the invention, and

644584

10th

2. other compounds which, although not homologs, belong to the range of the known compounds mentioned; one of them has superior properties as a sugar beet herbicide, two of which are commercially available herbicides.

All of the compounds used in the comparative tests listed below are generally defined as substituted phenyl-N-hydrocarbyloxyalkyl-2-haloacetanilides. The known compounds used for comparison purposes are identified in the tables as follows:

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

B. N- (MethoxymethyI) -2'-methoxy-6'-tert-butyl-2-bromo-acetanilide (Example 34 of U.S. Patent No. 3,547,620 and Example 36 of U.S. Patent No. 3,442,945).

C. N- (isobutoxymethyl) -2 ', 6'-dimethyl-2-chloroacetanilide; general term «Delachlor». (Example 31 of U.S. Patent 3,442,945 and Example 24 of U.S. Patent 3,547,620).

D. N- (allyloxymethyl) -2 ', 6'-dimethyl-2-chloroacetanilide (Example 47 of U.S. Patent 3,442,945).

E. N- (methoxymethyl) -2 ', 6'-diethyl-2-chloroacetanilide (Example 5 of U.S. Patents 3,442,945 and 3,547,620); General name «Alachlor», active ingredient in the commercial herbicide LASSO®, registered trademark of the Monsanto Company.

F. N- (methoxyethyl) -2'-methoxy-6'-methyl -? - chloroacetanide (compound no. 6 of BE PS 810 763; also listed in German application no. 2 402 983).

G. N- (Ethoxyethyl) -2'-methoxy-6'-methyl-2 chloroacetanilide (Compound No. 7 of BE PS 810 763).

H. N- (1-methoxyprop-2-yl) -2'-methoxy-6'-methyl-2-chloroacetanilide (compound no. 9 of BE PS 810 763).

I. N- (methoxyethyl) -2'-ethoxy-6'-methyl-2-chloroacetanilide (compound no. 16 of BE PS 810 763).

J. N- (Ethoxyethyl) -2'-ethoxy-6'-methyl-2-chloroacetanilide

(Compound No. 18 of BE PS 810 763). K. N- (methoxyethyl) -2'-methoxy-6'-isopropyl-2-chloroacet-

anilide (compound no. 26 of BE PS 810 763). L. N- (isopropoxyethyl) -2'-methoxy-6'-methyl-2-chloroacetanilide.

M. N- (1-methoxyprop-2-yl) -2'-ethyl-6'-methyl-2-chloroacetanilide (US Pat. No. 3,937,730 and German Patent Application No. 2,402,983); General name "Metolachlor", active ingredient in the commercial herbicide DUAL®, registered trademark of Ciba Geigy Corporation.

Compound C is less similar in structure to the homolog herbicides mentioned in U.S. Patent Nos. 3,442,945 and 3,547,620 because it lacks an alkoxy substituent in an ortho position, but it is included in the test as it is Sugar beet herbicide has shown superior properties compared to other compounds in the cited patents. Likewise, the compounds E and M were included in the tests, since they belong to the range of the relevant compounds mentioned and are commercially available. The compounds F to L were included in the tests because they have a certain structural similarity to certain compounds according to the invention.

Be: The pre-emergence tests compared the compounds according to the invention with the known compounds A to M in relation to the control of various weeds, emphasis being placed on annual narrow-leaved species which predominantly affect sugar beet crops. The results are summarized below.

In the following discussion of the data, reference is made to herbicide application rates which start with «GR15» and

«GR85» can be displayed; these quantities are given in kg / ha, which can be converted to lbs / A by dividing 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 GR85 quantities are used as a measure of the possible performance of commercially available products, although, of course, suitable commercially available 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 relative degree of harmlessness to crops and the harm to weeds, and is expressed as the ratio GR15 / GR85, i.e. GR15 amount for the crop divided by the GR85 amount for the weeds, both amounts in kg / ha. In the tables, the selectivity factors, insofar as they are used, are given in brackets after the weeds. "NS" means "non-selective"; a (-) after weed means low or indeterminate selectivity, e.g. because the actual GR] 5 and / or GR85 levels were higher or lower than the maximum or minimum levels used in the respective tests.

Because 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 harmlessness factors for the crop, i.e. the herbicide tolerance values are high because, for one reason or another, higher herbicide concentrations are often desired. Conversely, the amounts for weed control should be small for economic and possibly ecological reasons, 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 highest number of weeds with the lowest application rate 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 to the crop and weed control. 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.

Unless otherwise stated in the tables below, the data for compounds that were tested in multiple runs were averaged, with usual application rates within a range from 0.14 to 2.24 kg / ha. Various tables contain data from individual test runs with application rates between 0.07 kg / ha and 4.48 kg / ha.

Table IV shows the data for herbicidal activity from a first pre-emergence test series; the relative effectiveness of exemplary compounds according to the invention is compared with relevant known compounds as selective herbicides in the control of certain weeds which are usually associated with sugar beet. The following abbreviations are used in the tables for the weeds used in the tests: Avena fatua (WO), Echinochloa crus-galli (BYG). Digitaria sanguinalis (LCG), Alopecurus mysuroides (BG) and Se-taria lutescens (YFT).

5

10th

15

20th

25th

30th

35

40

45

50

55

60

65

11

644 584

TABLE IV

connection

GRi5 amount

(kg / ha)

Sugar beet

WHERE

BYG

GRgö quantity

(kg / ha) LCG

BG

YFT

A

0.56

0.56 (1.0)

0.14 (4.0)

<0.07 (> 8.0)

0.07 (8.0)

0.08 (7.0)

B

0.28

0.14 (2.0)

<0.07 (> 4.0)

<0.07 (> 4.0)

0.07 (4.0)

<0.07 (> 4.0)

O

0.84

0.80 (1.1)

<0.14 (> 6.0)

<0.14 (> 6.0)

0.28 (3.0)

0.14 (6.0)

F

<0.07

0.28 (NS)

<0.07 (-)

<0.07 (-)

0.14 (NS)

<0.07 (-)

G

<0.07

0.28 (NS)

<0.07 (-)

<0.07 (-)

0.07 (NS)

<0.07 (-)

L

<0.07

0.38 (NS)

<0.07 (-)

<0.07 (-)

0.07 (NS)

<0.07 (-)

M "

> 1.01

> 1.68 (NS)

<0.14 (> 7.2)

<0.14 (7.2)

1.87 (NS)

<0.14 (> 7.2)

Ex. Lb

> 2.05

0.44 (> 4.7)

<0.14 (> 14.6)

<0.14 (> 14.6)

<0.14 (> 14.6)

<0.14 (> 14.6)

Example 3a

> 2.24

0.84 (2.7)

<0.14 (> 16.0)

<0.14 (> 16.0)

<0.14 (> 16.0)

0.14 (16.0)

Ex. 4a

1.54

0.70 (2.2)

<0.14 (> 11.0)

<0.14 (> 11.0)

0.81 (> 1.9)

<0.14 (> 11.0)

a. Average of 2 repetitions b. Average of 3 repetitions

The data in Table IV show that the compounds according to the invention were clearly superior to the known compounds with regard to the harmlessness to the culture (indicated by the GR15 amount for sugar beet). Compared to the known compounds that are most closely related in structure, i.e. Compounds A and B with an N-alkoxymethyl-2'-alkoxy-6'-alkyl-2-halogenoacetanilide configuration, the compounds according to the invention tested were 5.8 to more than 8.0 times more harmless to sugar beet than compound B, and about 2.8 to more than 4.0 times more harmless than compound A. Even more remarkable is the fact that the compounds according to the invention were 22 to more than 32 times harmless to sugar beet than the known homologous compounds F, G and L, each of which caused more than 15% damage to the beet at the very low application rate of <0.07 kg / ha.

Compound C is not a homologue of the compounds of the invention, but is known for its superior properties as a beet herbicide compared to other compounds described in the above-mentioned US patents; compounds A and B are also described there. Compound M is also not a homologue of the compounds according to the invention, but falls within the scope of the mentioned German patent application No. 2 402 983. In which compounds F. And G are also described and which generally comprises compound L; Compound M, as mentioned above, is the active ingredient in a commercial herbicide. Regarding the GRJ5 amount of compounds C and M in Table IV, it should be noted that these compounds had a higher harmlessness factor than the other known compounds. However, compound C was only one third to half as harmless as the compounds according to the invention, and compound M was only about half to two thirds as harmless as the compounds according to the invention.

Simultaneously with the stated high harmlessness for the crop plants, the compounds according to the invention showed unit activities (i.e. phytotoxicity per herbicide unit) against tested weeds (indicated as

GR85 amount), which are more or less comparable to the known compounds. The high harmlessness factor for the crop combined with the high uniform activity towards the weeds resulted in remarkably higher selectivity factors for the compounds according to the invention than for the known compounds, with the only exception of the compound of Example 4 35 compared to Alopecurus m.

Comparing in Table IV the selectivity factors of the known compounds with those of the compound of Example 1 for the respective weeds in sugar beets, it is noteworthy that the compound of 40 Example 1 compared to the known compounds for Avena fatua by about 2, 4 to over 4.7 times, compared to Echinochloa crus-galli and yellow foxtail about 2.1 to over 14.6 times, and to Digitaria and Alopecurus about 1.8 to over 14.6 times more selective. 45 Additional tests with selected compounds according to the invention showed control of Echinochloa, Digitaria, Alopecurus and yellow foxtail at application rates as low as 0.07 kg / ha and below. Thus, the compound of Example 1 controlled each of the weeds at 0.07 kg / ha or less; the compound of Example 4 controlled Echinochloa, Digitaria and yellow foxtail at less than 0.07 kg / ha, and the compound of Example 3 controlled Echinochloa and Digitaria at 0.07 kg / ha or less.

55 In further comparative tests, the herbicidal pre-run activity and the selectivity factors of the known compounds C.E, H and M were determined and compared with those of the compounds of Examples 1 to 8; the results of these tests are summarized in Table V.

644 584

12

TABLE V

connection

GRi5 amount

(kg / ha)

Sugar beet

WHERE

BYG

GRss amount

(kg / ha) LCG

BG

YFT

O

0.84

0.80 (1.1)

<0.14 (> 6.0)

<0.14 (> 6.0)

0.28 (3.0)

0.14 (6.0)

E

<0.14

0.56 (NS)

<0.14 (-)

<0.14 (-)

2.24 (NS)

<0.14 (-)

H

<0.14

0.86 (NS)

<0.14 (-)

<0.14 (-)

1.12 (NS)

<0.14 (-)

M "

> 1.01

> 1.68 (NS)

<0.14 (> 7.2)

<0.14 (> 7.2)

1.87 (NS)

<0.14 (> 7.2)

Ex. Lb

> 2.05

0.44 (> 4.7)

<0.14 (> 14.6)

<0.14 (> 14.6)

<0.14 (> 14.6)

<0.14 (> 14.6)

Ex. 2

1.12

0.56 (2.0)

<0.14 (> 8.0)

<0.14 (> 8.0)

0.14 (8.0)

<0.14 (> 8.0)

Example 3a

> 2.24

0.84 (2.7)

<0.14 (> 16.0)

<0.14 (> 16.0)

<0.14 (> 16.0

<0.14 (> 16.0)

Ex. 4a

1.54

0.70 (2.2)

<0.14 (> 11.0)

<0.14 (> 11.0)

0.81 (> 1.9)

<0.14 (11.0>

Ex. 5

1.12

0.42 (> 8.0)

<0.14 (> 8.0)

<0.14 (> 8.0)

0.42 (> 8.0)

<0.14 (> 8.0)

Ex. 6

2.24

1.12 (2.0)

<0.14 (> 16.0)

<0.14 (> 16.0)

0.38 (3.0)

<0.14 (> 16.0)

Ex. 7

2.24

2.24 (1.0)

<0.14 (> 16.0)

<0.14 (> 16.0)

0.56 (4.0)

<0.14 (> 16.0)

Ex. 8

2.24

1.68 (1.3)

<0.14 (> 16.0)

<0.14 (> 16.0)

0.56 (4.0)

0.14 (16.0)

a. Average of 2 repetitions b Average of 3 repetitions

Table V shows that each compound according to the invention had a significantly higher harmlessness factor for sugar beets than all previously known compounds. Particular attention should be paid to the harmlessness factors of the compounds of Examples 1, 3 and 6 to 8, which are 2.2 to over 16 times larger than those of the known compounds. In addition, the compounds according to the invention showed uniformly and outstandingly superior selectivity factors compared to the known compounds, with the exception of individual cases. The selectivity factors of compound C compared to Avena f. slightly larger than that of Example 7, slightly larger than that of the compound of Example 4 and equivalent to Example 6 compared to Alopecurus. The known compounds E, H and M showed no selectivity towards Avena f. and Alopecurus, and the selectivity of compounds E and H over the remaining weeds was questionable or, at best, poor; in any case, the low harmlessness factors of these compounds make them unsuitable as sugar beet herbicides.

Since the pre-run dates of Tebelle IV and V were obtained with the same routine methods, a comparison of the herbicidal activity of the compounds according to the invention from Table IV with the known compounds from Table V, which are not listed in Table IV, can also be carried out, and vice versa. Here too it is clear that each of the compounds according to the invention was clearly and without exception superior to all known and most closely related known compounds, with regard to the harmlessness for the crop as well as with regard to the selective weed control, which is indicated by the selectivity factor; individual exceptions also apply here. The selectivity factor of a certain known compound for a specific weed can be greater than for a specific compound according to the invention; in each of these cases, however, the low beet harmlessness factor makes the corresponding compound known as beet-

30th

herbicidal unsuitable. For example, the selectivity factor 2.0 of compound B (Table IV) compared to Avena f. for sugar beet larger than that of the compounds of Examples 7 and 8 (1.0 and 1.3, Table V). However, the harmlessness factors of both compounds according to the invention for sugar beets are 8 times larger than for compound B, and the selectivity factors of the compounds according to the invention mentioned are at least 4 times larger than for compound B compared to echinochloa, digitaria and yellow foxtail, and are equivalent to Compound B versus Alopecurus.

In a further comparative test of the herbicidal activity, the compound from Example 1 and the compounds I and J were tested against Avena f., Echinochloa, Digi-45 taria, Alopecurus and yellow foxtail. The test results (average of 2 replicates) are summarized in Table VI; the assessment was made about 18 days after treatment; the selectivity factors for each weed are given in parentheses below the GR85 levels.

13

644584

TABLE VI

connection

GRi5 amount kg / ha

Sugar beet

WHERE

BYG

GRss amount kg / ha LCG

BG

YFT

E.g.

<1.12

0.35

<0.14

<0.14

<0.14

<0.14

(> 3.2)

(> 8.0)

(> 8.0)

(> 8.0)

(> 8.0)

I.

<0.28

-0.99

<0.14

<0.14

0.21

<0.14

(NS)

(—2.0)

(-2.0)

(-1.3)

(—2.0)

J

<0.21

0.28

<0.14

<0.14

0.21

<0.14

(NS)

(—1.5)

(—1.5)

(NS)

(—1.5)

The superiority of the compound of Example 1 over Compounds I and J results from the harmlessness factor for the crop and the selectivity to each weed tested; Compound J was nonselective to Avena f. and Alopecurus, and Compound I was nonselective to Avena f. and just selective towards Alopecurus.

In a test, the compound of Example 1 and the compounds I and J were also tested against fluffy trespe (DB), amaranthus (RRP) and annual ryegrass (AR) in sugar beets, with application rates between 0.07 and 1.12 kg /Ha; the assessment was carried out 18 days after treatment; the test results are summarized in Table VII; the selectivity factors are given in parentheses under each weed.

TABLE VII

Connect

GRis amount

GR85 quantity

dung

(kg / ha)

(kg / ha)

Sugar beet

DB

RRP

AR

Ex. 1

> 1.12

0.07

> 1.12

<0.09

(> 16.0)

(-) '

(> 12.0)

I.

0.07

<0.14

0.07

0.28

(NS)

(1.0)

(NS)

J

<0.07

<0.09

<0.07

<0.07

(NS)

(-)

(-)

The data show that known compounds I and J were harmful to beets at levels as low as 0.07 kg / ha and below, and that Compound I was not-20 selective for downy broth and annual ryegrass, while Compound J was fluffy trespe was non-selective and only scarcely or indefinitely at application rates below 0.07 kg / ha. The compound of Example 1, on the other hand, was harmless for sugar beet at the maximum test amount of 1.12 kg / ha and controlled fluffy bristle and annual ryegrass with selectivity factors of about 16 and 12, however, the control of amaranthus was scarce or indefinite Quantities over 1.12 kg / ha. Another greenhouse test was carried out to compare the compounds of Examples 2 and 5 according to the invention with the compounds K and D, i.e. with the closest related known compounds. Example 2 and compound K are characterized by an isopropyl radical in one ortho position, an alkoxy radical in the other ortho position, and an alkoxyalkyl radical at the anilide nitrogen atom. Compound D and the compound of Example 5 are characterized by alkenyloxymethyl radicals on the nitrogen atom and a methyl radical in an ortho position. The herbicides were applied at application rates of 0.07 to 1.12 kg / ha; 40 The assessment was made 19 days after treatment; the results are summarized in Table VIII.

TABLE VIII

connection

GRi5 amount kg / ha

Sugar beet

WHERE

BYG

GR85 quantity kg / ha LCG

BG

YFT

Ex. 2

> 1.12

0.14

<0.07

<0.07

0.24

<0.07

(> 8.0)

(> 16.0)

(> 16.0)

(> 4.7)

(> 16.0)

K

0.19

0.07

<0.07

<0.07

0.49

<0.07

(2.7)

(2.7)

(2.7)

(NS)

(2.7)

Example 5

1.12

0.14

<0.07

<0.07

0.78

0.09

(8.0)

(> 16.0)

(> 16.0)

(1.4)

(11.1)

D

0.19

0.19

<0.07

<0.07

0.56

<0.07

(1.0)

(> 2.7)

(> 2.7)

(NS)

(> 2.7)

65 The data in Table VIII clearly show the superiority of the compounds according to the invention over the compounds D and K. In particular, the compounds of Examples 2 and 5 were harmless to sugar beet

644584

14

at application rates of 1.12 kg / ha and more, while the compounds D and K had GR15 amounts of only 0.19 kg / ha. Furthermore, the selectivity factors of the compounds according to the invention exceeded the selectivity factors of the known compounds several times over each weed tested in sugar beets; the known compounds were non-selective towards Alopecurus.

Further tests were carried out to demonstrate the superior herbicidal properties of other io compounds according to the invention. In a series of greenhouse tests, the compounds of Examples 9 to 12 were tested against Avena, Echinochloa crus-galli, Digitaria, Alopecurus and yellow foxtail in sugar beets; the results are summarized in Table IX. 15

TABLE IX

connection

GRi5 amount

(kg / ha)

Sugar beet

WHERE

BYG

GR85 quantities (kg / ha) LCG

YFT

BG

Ex. 9a

1.0

0.55

<0.14

<0.14

0.19

<0.14

(1.8)

(7.1)

(7.1)

(5.2)

(7.1)

Ex. 10 "

> 1.12

0.34

<0.14

<0.14

<0.14

<0.14

(> 3.3)

(> 8.0)

(> 8.0)

(> 8.0)

(> 8.0)

Ex. IIe

> 1.12

0.19

<0.14

<0.14

<0.14

<0.14)

(> 5.9)

(> 8.0)

(> 8.0)

(> 8.0)

(> 8.0)

Ex. 12

> 1.12

0.84

<0.14

0.14

0.14

0.14

(> 1.3)

(> 8.0)

(> 8.0)

(> 8.0)

(> 8.0)

a Average of 4 repetitions b Average of 2 repetitions c Average of 3 repetitions

Once again, the superior pre-emergence activity of the compounds according to the invention could be shown both on an absolute basis and in comparison with the performance of relevant known compounds, as is shown in Tables IV to VIII with regard to harmlessness factors for the crop plants, unit activities, weed control and crop plants / weed selectivity factors was shown.

As already mentioned, the data for the compounds tested in several runs were obtained from tests with herbicide application rates within a range from 0.14 to 1.12 kg / ha. However, additional tests with selected compounds according to the invention showed harmlessness to sugar beets at quantities of at least 4.48 kg / ha, and selective control of various weeds at quantities as low as 0.07 kg / ha. For example, the compound of Example 1 selective control of the more resistant weeds Alopecurus and downy trespe, as well as the less resistant weeds Echinochloa, Digitaria, yellow foxtail and annual ryegrass at as low as 0.07 kg / ha and below. Similarly, other compounds according to the invention controlled one or more of the above less resistant weeds at 0.07 kg / ha.

In a field test, the ratio of the harmlessness for sugar beet to the weed control was tested with the compounds of Example 1 and the known compounds C, E and M, namely against Echinochloa and green foxtail (Setaria viridis); Application rates of 1.12 kg / ha to 4.48 kg / ha were either applied to the surface ("SA") or incorporated into the soil before planting ("PPI"). The treatment was on

Ray Schiuff clay with 1.8% organic matter; the conditions were relatively dry, since only 0.03 cm of rain fell within the first 7 days after treatment; the results of the field test are summarized in Table X.

TABLE X

Compound quantity% inhibition (kg / ha) sugar beet Echinochloa Grüner

Foxtail

PPI SA PPI SA PPI SA

Ex. 1

1.12

0

0

85

27th

85

57

2.24

10th

3rd

92

48

92

65

4.48

12

13

98

78

98

85

C.

1.12

10th

5

78

42

88

77

2.24

22

18th

87

77

93

87

4.48

57

25th

98

90

98

88

E

1.12

30th

30th

87

68

88

85

2.24

80

63

100

95

100

95

4.48

100

90

100

98

100

97

M

1.12

15

15

95

40

95

62

2.24

30th

23

100

78

100

85

4.48

63

45

100

93

100

92

65

The data in Table X show that of all the compounds tested, only the compound from Example 1 is harmless to sugar beet (i.e. damage up to

15

644584

15%) at up to at least 4.48 kg / ha (maximum test amount) while selectively controlling both Echinochloa and green foxtail at 1.12 kg / ha under PPI conditions; not even at 2.24 kg / ha did any of the known compounds selectively control one of the 5 weeds; Compound M selectively controlled both weeds under PPI conditions at 1.12 kg / ha, but had a narrow margin for crop tolerance.

The compound of Example 1 was also tested in field 10 to test its pre-emergence selectivity to Setaria species, Echinochloa and Panicum miliaceum in several cultures; data for three repeat runs are presented in Table XI for surface application (SA) and incorporation into the soil (PPI) 15 of the herbicide. The seeds were planted in a fine seed bed of silt loam of medium moisture 5.08 cm deep. The first rain (0.51 cm) fell the day after the treatment, the second rain (0.64 cm) two days after the treatment; the total amount of rain 22 days after 20

the treatment was 4.57 cm. The assessment was carried out 6 weeks after the treatment. TABET 1

% Inhibition

Connection- Amount- Toma- Gur- Bush- Earth- Tree- Soy- Sugar- Rape Fuchs- Echino- Panicum-

dung (kg / ha) ten beans nuts wool beans beet tail chloa milia

weise (Spp) ceum

Ex. 1 S.A.

P.P.I.

0.58

0

0

0

0

0

0

0

0

33

33

1.12

0

0

0

0

0

0

0

0

82

82

20th

2.24

0

10th

0

0

0

0

0

0

93

93

4.48

7

0

3rd

0

0

0

0

0

93

93

100

0.58

0

0

0

0

0

0

0

0

63

63

25th

1.12

5

0

3rd

0

3rd

0

3rd

0

75

85

17th

2.24

5

5

0

0

0

0

0

0

90

98

50

4.48

43

40

17th

3rd

13

0

8th

0

97

97

73

Table XI shows that the compound of Example 1 generally gave equivalent performance up to application rates of 4.48 kg / ha under SA and PPI conditions (except for tomatoes, cucumbers and P. miliaceum at 4.48 kg / ha PPI and against foxtails and echinochloa at 0.58 kg / ha). Under SA conditions, the compound of Example 1 selectively controlled foxtails and Echinochloa in all test cultures with amounts slightly above 1.12 kg / ha, and Panicum miliaceum with 4.48 kg / ha. Echinochloa was selectively controlled at 1.12 kg / ha under PPI conditions, and foxtails at between 1.12 and 2.24 kg / ha, the harmlessness for the culture reaching up to 4.48 kg / ha for all cultures, except tomatoes, cucumbers and bush beans.

A definite advantage of a herbicide is that it can work in a wide variety of soil types. Accordingly, Table XII summarizes data comparing the herbicidal activity of the compound of Example 1 and the compounds C and M on various annual grasses in sugar beets in a variety of soil types with varying proportions of organic substances and clays. For these tests, pots were filled with Ray Schluff-loam soil, which was compacted up to 0.95 cm below the pot surface, then sugar beets, Avena f .. Echinochloa, Digitaria, Alopecurus and yellow foxtail were sown. The seeds were each made with 0.13 cm Ray silt clay, Florida peat clay, Florida sand, Wabash silty clay, drummer silty

40 clay or sarpy silty clay covered. Each herbicide was applied to the surface with a belt sprayer at 187 l / ha, 2.11 kp / cm2. Each pot was irrigated with 0.64 cm from above before it was placed on a greenhouse table 45 for subsequent irrigation. The assessment was carried out 15 days after the treatment. The results of the soil tests, which are the average of 2 runs, are summarized in Table XII; the selectivity factors are given in brackets after the GR85 amount for the weeds. 50 The soil composition was as follows:

55

Soil type organic matter

volume

Shares of silt

Sand pH

Ray silt clay

1.2

6.4

74.8

18.8

6.5

60

Florida peat clay

22.1

N / A"

N / A"

N / A"

5.2

Florida (Leon) sand

2.3

1.8

N / A"

N / A"

6.1

Drummer silty

loam

3.6

12.4

52.8

34.8

7.0

65

Wabash tone

2.7

44.4

34.8

20.8

6.2

" unavailable

644584

16

TABLE XII

Soil type and connection

GRi5 amount

(kg / ha)

Sugar beet

Avena

Echinochloa

GR85 quantities (kg / ha) Digitaria

Alopecurus yellow

Foxtail

Ray silt clay

Ex. 1

2.24

1.12 (2.0)

<0.14 (> 16.0)

<0.14 (> 16.0)

0.14 (> 16.0)

<0.14 (> 16.0)

C.

0.56

1.12 (NS)

<0.14 (4.0)

0.14 (> 4.0)

0.14 (4.0)

<0.14 (> 4.0)

M

0.28

1.12 (NS)

<0.14 (2.0)

0.14 (2.0)

0.56 (NS)

<0.14 (> 2.0)

Florida peat clay

Ex. 1

> 2.24

> 2.24 (-)

> 2.24 (-)

> 2.24 (-)

> 2.24 (-)

2.24 (> 1.0)

C.

> 2.24

> 2.24 (-)

> 2.24 (-)

2.24 (> 1.0)

> 2.24 (-)

2.24 (> 1.0)

M

> 2.24

> 2.24 (-)

> 2.24 (-)

> 2.24 (-)

> 2.24 (-)

> 2.24 (-)

Florida sand

Ex. 1

> 2.24

> 2.24 (-)

1.12 (> 2.0)

1.12 (> 2.0)

> 2.24 (-)

1.07> 2.1)

C.

1.12

2.24 (NS)

2.24 (NS)

1.12 (1.0)

> 2.24 (NS)

1.12 (1.0)

M

1.12

> 2.24 (NS)

> 2.24 (NS)

2.24 (NS)

> 2.24 (NS)

0.56 (2.0)

Wabash tone

Ex. 1

> 2.24

1.12 (> 2.0)

0.21 (> 10.7)

<0.14 (> 16.0)

0.23 (> 9.7)

0.21 (> 10.7)

C.

0.38

1.12 (NS)

0.14 (2.7)

0.56 (NS)

0.56 (NS)

<0.14 (2.7)

M

0.38

1.12 (NS)

0.14 (2.7)

0.28 (1.4)

1.68 (NS)

0.14 (2.7)

Drummer silt clay

Ex. 1

0.56

2.24 (NS)

0.52 (1.1)

0.56 (1.0)

2.24 (NS)

0.43 (1.3)

C.

1.12

1.12 (1.0)

0.28 (4.0)

0.56) 2.0)

1.12 (1.0)

0.28 (4.0)

M

1.68

> 2.24 (NS)

0.28 (> 6.0)

0.96 (> 1.8)

> 2.24 (NS)

0.56 (> 3.0)

Table XII shows that the compound of Example 1 showed clearly superior harmlessness to sugar beet and higher selectivity factors than the compounds C and M over all weeds (with two minor exceptions) in three out of five soils, i.e. in Ray silt clay, Florida sand and Wabash clay. The compound of Example 1 was the only compound (the Avena in Ray silt and Wabash clay, Echinochloa in Florida sand and Alopecurus in Wabash clay selectively controlled. The results for Florida peat soil (22.1% organics) were fairly inaccurate in the test amount However, indicate that a high level of organics tends to reduce the effectiveness of each of the test compounds .. In Drummer silt loam, the compound of Example 1 did not work as well as the known compounds, but overall showed higher activity in a number of soil types.

Laboratory tests were carried out in order to determine the relative resistance of the herbicides and known compounds according to the invention to leaching into the soil and the resulting herbicidal activity. In these tests, the compound of Example 1 and compounds C and M were dissolved in acetone, then sprayed in various concentrations onto weighed amounts of Ray silt clay contained in pots in which the drain holes in the bottom of the pot were covered with filter paper . The pots of treated earth were leached out by placing them on a turntable rotating under two nozzles of a water container; the nozzles were set to deliver 2.5 cm of water per hour and simulate rain. The leaching rates were adjusted to 40 by varying the time on the turntable. The water was piped into the bottom of the pots, then it was drained through the filter paper and drain holes. The pots then stood at room temperature for 7 days. Then the treated soil was removed from 45 pots, crumbled, and spread as a surface layer on other pots containing Ray silt clay seeded with beet, Avena, Echinochloa, Digitaria, Alopecurus and yellow foxtail seeds. The pots were then placed on greenhouse tables for 2 weeks and watered from below. The percentage growth observations were recorded; data for the test compounds are averages of two runs and are summarized in Table XIII; the weed abbreviations correspond to the earlier tables.

TABLE XIII

connection

Amount (kg / ha)

Rain (cm)

Sugar beet

WHERE

BYG

% Inhibition LCG

BG

YFT

Ex. 1

2.24

0

10th

100

100

100

100

100

1.27

15

100

100

100

100

100

2.54

10th

100

100

100

100

100

5.08

10th

95

100

100

100

100

10.16

10th

75

100

85

90

95

17th

644 584

TABLE XIII (continued)

Connection quantity (kg / ha)

Rain (cm)

Sugar beet

WHERE

BYG

% Inhibition LCG

BG

YFT

0.56

0

0

95

100

100

100

100

1.27

0

95

100

100

100

100

2.54

0

95

100

100

100

100

5.08

0

85

100

95

95

100

10.16

0

30th

75

20th

20th

'50

0.14

0

0

85

100

95

95

100

1.27

0

85

100

95

95

100

2.54

0

75

95

95

75

100

5.08

0

50

95

85

75

95

10.16

0

30th

50

30th

20th

50

c

2.24

0

30th

100

100

100

100

100

1.27

40

100

100

100

100

100

2.54

40

95

100

100

95

100

5.08

15

30th

95

95

85

95

10.16

0

20th

75

50

20th

50

0.56

0

15

95

100

100

95

100

1.27

25th

85

100

95

95

100

2.54

10th

50

95

85

75

95

5.07

0

85

75

65

50

95

10.16

0

15

30th

30th

20th

50

0.14

9

10th

50

95

95

40

95

1.27

0

30th

95

85

40

85

2.54

0

30th

85

60.

20th

85

5.08

0

30th

65

40

20th

75

16.16

'0

30th

0

30th

0

40

M

2.24

0

40

85

100

100

95

100

1.27

30th

95

100

100

85

1Q0

2.54

20th

85

100

100

60

100

5.08

10th

30th

95

85

30th

95

10.16

10th

30th

60

50

15

50

0.56

0

15

85

100

100

95

100

1.27

15

40

100

100

65

100

2.54

0

50

95

95

30th

95

5.08

0

20th

75

85

20th

75

10.16

0

0

30th

40

0

20th

0.14

0

0

85

95

95

75

100

1.27

0

50

95

85

60

95

2.54

0

40

75

50

30th

95

5.08

0

0

60

30th

20th

60

10.16

0

0

0

0

0

0

Table XIII shows that the compound of Example 1 was harmless to sugar beets up to at least 2.24 kg / ha and selectively controlled all weeds under a simulated rain of 10.16 cm, except Avena, which controls up to 7.62 cm has been. At 2.24 kg / ha, compounds C and M were harmful to sugar beets until they were diluted with 5.08 cm of rain; under these conditions none of the compounds controlled Avena selectively. Compound M also not Alopecurus. At the lowest application rate of 0.14 kg / ha, the compound of Example 1 selectively controlled all weeds tested under an amount of rain up to 1.27 cm, and Echinochloa, Digitaria and yellow foxtail up to 5.08 cm of rain. At 0.14 kg / ha, however, under no control

55 Amount of rain neither compound C nor M selectively Alopecurus, compound C nor Avena, and both compounds had lost their selectivity to all weeds tested in sugar beets with 5.08 cm of rain. This clearly shows that the compound according to the invention is much more resistant to leaching into the soil under different rain conditions than ied of the known compounds, so that it offers a more reliable and prolonged herbicidal activity.

Finally, in order to further demonstrate the unexpected nature and superiority of the compounds according to the invention, table XIV also contains data for the herbicidal pre-emergence effect of further compounds with a similar structure, including homologues of the invented

644584

18th

compounds according to the invention. Compounds N to T of Table XIV are identified as follows:

N. N- (isopropoxymethyl) -2'-methoxy-6'-methyl-2-chloro

acetanilide. 5

O. N- (IsobutoxymethyI) -2'-ethoxy-2-chloroacetanilide. P. N- (isobutoxymethyl) -2'-methoxy-2-chloroacetanilide. Q. N- (Isobutoxymethyl) -2'-methoxy-6'-methyl-2-chloroacetanilide.

R. N- (Ethoxymethyl) -2'-methoxy-6'-methyl-2-chloroacet-10 anilide.

S. N- (l-methylpropoxymethyl) -2'-methoxy-6 'lmethyl-2-

-chloroacetanilide. T. N- / ethoxymethyl) -2'-isopropoxy-6'-methyl-2-chloroacet-

anilide. ) 5

TABLE XIV

connection

GRi5 amount

(kg / ha)

Sugar beet

WHERE

BYG

GR85 amount (kg / ha) LCG

BG

YFT

N / A

<0.14

0.14 (NS)

<0.14 (-)

<0.14 (-)

0.14 (NS)

<0.14 (-)

O

<0.14

> 2.24 (NS)

<0.14 (-)

<0.14 (-)

1.90 (NS)

0.14 (NS)

P

<0.14

> 2.24 (NS)

0.14 (NS)

0.14 (NS)

0.56 (NS)

0.28 (NS)

Q

<0.14

0.28 (NS)

<0.14 (-)

<0.14 (-)

0.14 (NS)

<0.14 (-)

R

<0.07

0.09 (NS)

<0.07 (-)

<0.07 (-)

0.07 (NS)

<0.07 (-)

S

0.14

0.49 (NS)

<0.07 (> 2.0)

<0.07 (> 2.0)

0.14 (1.0)

<0.14 (> 1.0)

Ta

0.23

0.26 (NS)

<0.14 (> 1.6)

. <0.14 (> 1.6)

0.12 (1.9)

<0.14 (> 1.6)

a Average of 2 repetitions

It is pointed out that the compounds N to T, like the compounds according to the invention of Examples 1 to 12, fall under the general description of the above-mentioned US Pat. Nos. 3,442,945 and 3,547,620, but that they are not specifically described there . It would therefore be expected that compounds of the type described there generally have comparable herbicidal properties. However, the completely unexpected and outstanding properties of the compounds according to the invention compared to homologous and closely related compounds are further demonstrated by the data for the compounds N to T in Table XIV. Again, it should be noted that the compounds N to T (as well as related known compounds, which are particularly shown in Tables IV to VIII) had very low harmlessness factors for sugar beet, as is demonstrated by the low GR1S application rates. Furthermore, none of the compounds in Table XIV showed selective control of Avena f. in sugar beets. It is also interesting to note that Compound P was not selective to any of the weeds tested and that Compound N, O, Q and R was completely non-selective and / or slightly selective to all weeds tested. Of the compounds in Table XIV, only the compounds S and T showed a selective control of Echinochloa, Digitaria, Alopecurus and yellow foxtail.

However, it is again pointed out that the unacceptably low tolerance of sugar beet to the compounds S and T, together with the non-selectivity to Avena and the low selectivity to the other weeds in the test make these compounds completely unacceptable as sugar beet herbicides. It is also found (with reference to Tables IV to VIII) that the harmlessness factors

40 for sugar beet and the selectivity factors of the compounds according to the invention compared to the above weeds are overwhelmingly superior to those of the compounds S and T.

It follows from the preceding detailed description that the compounds according to the invention have shown unexpected and outstanding herbicidal properties, both absolutely and relative to the known, structurally relevant compounds, other related homologues and the like. Analogs, including commercial 2-haloacetanilides. In particular, the compounds according to the invention showed excellent harmlessness to sugar beets, as well as excellent selectivity factors, in particular with regard to weeds which are difficult to kill, such as Avena fatua, Alopecurus mysuroides and fluffy bristle, as well as other problem weeds such as yellow foxtail, Echinochloa crus-galli, Digitaria sanguinalis, and annual ryegrass ., as compiled in Tables II to X.

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 mixed with the active ingredient

65 an adjuvant, which includes diluents, extenders, carriers and conditioning agents, so that preparations in the form of finely divided solid particles, granules, pellets, solutions, dispersions or

19th

644584

Emulsions are created. 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 agents 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 lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate, and polymethylene bisnaphthalene sulfonates.

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. The wettable powders according to the invention usually contain about 0.5 to 60 parts (preferably 5 to 20 parts) of active ingredient, about 0.25 to 25 parts (preferably 1 to 15 parts) of wetting agent, about 0.25 to 25 parts (preferably 1.0 up to 15 parts) of dispersant and 5 to about 95 parts (preferably 5 to 50 parts) of inert extendable solid, all parts being based on the weight of the entire preparation. If necessary, about 0.1 to 2 parts 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 is formed which is dispersed in an aqueous phase. In one embodiment, very small capsules are formed by bringing together an aqueous phase containing a lignin sulfonate emulsifier, a water-immiscible chemical and polymethylene polyphenyliso-5 cyanate that disperses the water-immiscible phase in the aqueous phase and then a polyfunctional one Amin 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 15 in solvents that are immiscible or only partially miscible with water, together with a surfactant. Suitable solvents for the active ingredient according to the invention include Dimethylformide, dimethyl sulfoxide, N-methylpyrrolidone, hydrocarbons and water-immiscible ethers, 20 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.

30 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 substance from the particles, a surface-active agent as described 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 adjuvants listed above. 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, 60 biphenyl ethers and the like, such as:

Heterocyclic nitrogen / sulfur derivatives 2-chloro-4-ethylamino-6-isopropylamino-s-triazine

2-chloro-4,6-bis (isopropylamino) -s-triazine 65 2-chloro-4,6-bis- (ethylamino) -s-triazine

3-isopropyl-1H-2, 1, 3-benzothiadiazin-4- (3H) -on-2,2-dioxide 3-amino-1,2,4-triazole

6,7-Dihydrodipyrido- (1,2-a: 2 ', r-c) -pyrazidiinium salt

644584

20th

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

Ureas

N '- (4-Chlorophenoxy) phenyl-N, N-dimethylurea N.N-dimethylI-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-dimethyl urea

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

Carbamate / T hiolcarbamate 2-ChlorallyldiethyIdithiocarbamat S- (4-chlorobenzyl) -N, N-diethylthiolcarbamat Isopropyl-N- (3-chlorophenyl) -carbamat S-2,3-DichIoralIyl-N, N-diisopropyIthiolcarbamat EthyI-N, N- dipropylthiol carbamate S-propyl dipropyl thiol carbamate

Acetamidef A cetanilidef aniline / amide 2-chloro-N, N-diallylacetamide N, N-dimethyl-2,2-diphenylacetamide

N- (2,4-dimethyl-5 - {[(trifluoromethyl) sulfonyl] amido} -phe-

nvl) -acetamide N-isopropyl-2-chloroacetanilide 2 ', 6'-diethyl-N-methoxymethyl-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- (l, l-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] propionate

3-amino-2,5-dichlorobenzoic acid 2-methoxy-3,6-dichlorobenzoic acid 2,3,6-trichlorophenylacetic acid

N-1 -N aphthalylphthalamic acid

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

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

N- (phosphonomethyl) glycine and its CH monoalkylamine and alkali metal salts and combinations thereof

Ether

2,4-dichlorophenyl-4-nitrophenyl ether

2-chloro-a, a, "- trifluoro-p-tolyI-3-ethoxy-4-nitrodiphenyl ether

Miscellaneous 2,6-dichlorobenzonitrile monosodium methanarsonate 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 see: nd and others. Substances in which plant organisms root 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.

I. Emulsifiable concentrates

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

B. Connection of Example No. 2

Calcium dodecyl sulfonate / alkylaryl poly ether alcohol mixture

C9 aromatic hydrocarbon solution; medium

Connection of Example No. 11

Calcium dodecylbenzenesulfonate / polyoxy-

ethylene ether mixture

(e.g. Atlox 3437F)

Xylene

II. Liquid concentrates

30th

A. Compound of Example No. 1 xylene

B. Compound of Example No. 2 dimethyl sulfoxide

C. Compound of Example No. 11 N-M ethyl pyrrole idon

D. Compound of Example No. 10 Ethoxylated Castor Oil Rhodamine B Dimethylformamide

III. Emulsions

55 A. Compound of Example No. 3

Polyoxyethylene / polyoxypropylene bloclc copolymer with butanol (e.g. Tergitol XH)

water

B. Compound of Example No. 4 polyoxyethylene / polyoxypropylene block copolymer with butanol water

Wt% 50.0

5.0 45.0

100.0

85.0

4.0

11.0

100.0

5.0

1.0 94.0

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

100.0

% By weight 40.0

4.0 56.0

100.0

5.0

3.5 91.5

100.0

21st

644 584

IV. Wettable powders

% By weight

A. Compound of Example No. 5 25.0

Sodium lignosulfonate 3.0

Sodium N-methyl-N-oleyl taurate 1.0

Amorphous silica (synthetic) 71.0

100.0

B. Compound of Example No. 6 80.00

Sodium dioctyl sulfosuccinate 1.25

Calcium lignosulfonate 2.75

Amorphous silica (synthetic) 16.00

100.00

C. Compound of Example No. 7 10.0

Sodium lignosulfonate 3.0

S atrium-N-methy 1-N-oley itatate 1.0

Kaolinite clay 86.0

100.0

V. dusts

% By weight

A. Compound of Example No. 1 2.0

Attapulgite 98.0

100.0

B. Compound of Example No. 8 60.0

Montmorillonite 40.0

100.0

C Compound of Example No. 9 30.0

Bentonite 70.0

100.0

D. Compound of Example No. 12 1.0

Diatomaceous earth 99.0

100.0

VI. Granule

% By weight

A. Compound of Example No. 1 15.0

Granulated attapulgite (20/40 sieve) 85.0

100.0

B. Compound of Example No. 11 30.0

Diatomaceous earth (20/40) 70.0

100.0

C. Compound of Example No. 10 0.5

Bentonite (20/40) 99.5

100.0

D. Compound of Example No. 3 5.0

Pyrophyllite (20/40) 95.0

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 € -21) 0.5

Water 89.5

100.0

C. Compound of Example No. 10

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. The preparations can be applied to the earth as liquids and solid particles 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 air 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 location of the undesired weeds is essential and critical for the use according to the invention. The exact amount of active ingredient to be used depends on various factors, e.g. on the type of plant and its stage of development, type and condition of the soil, the amount of rain and the specific acetanilide used. In the case of selective pre-run application to plants or soil, an application rate of 0.02 to 11.2 kg / ha, preferably of about 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. The person skilled in the art can, on the basis of 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 the usual types of soil, as defined under "soils" in Webster's New International Dictionnary, 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, dung, humus, sand and the like, which can maintain plant growth.

5

10th

15

20th

25th

30th

35

40

45

50

55

60

Claims (44)

644584 2. Compounds according to claim 1, characterized in that R is a C2_4 alkyl or allyl radical and Rj is a C3 or C4 alkyl radical. 2nd PATENT CLAIMS 1. Compounds of the formula: 0 II characterized in that R represents ethyl, n-propyl, isopropyl, isobutyl, allyl or butenyl; Rj is methyl, n-propyl, isopropyl, n-butyl, isobutyl or iso-amyl and R2 is methyl, ethyl or isopropyl; with the proviso that when R2 is isopropyl, R is ethyl and Ri is n-butyl; when Rjj is ethyl, R is ethyl, n-propyl or allyl and R, n-butyl or isobutyl; when R is n-propyl, Rx is n-butyl or isobutyl; when R represents isopropyl, Rj represents isobutyl; when R is isobutyl, Rx is n-propyl, isopropyl isobutyl or isoamyl, and when R is butenyl, Rt is methyl. 3rd 644584 3. Compounds according to claim 2, characterized in that Rj is an isobutyl radical. 4. A compound according to claim 3, characterized in that it is N- (n-propoxymethyl) -2'-isobutoxy-6'-methyl-2 - chloroacetaniîid. 5. A compound according to claim 3, characterized in that it is N- (isobutoxymethyl) -2'-isobutoxy-6'-methyl-2 - chloroacetanilide. 6. A compound according to claim 3, characterized in that it is N-isopropoxymethyl) -2'-isobutoxy-6'-methyl - 2-chloroacetanilide. 7. A compound according to claim 3, characterized in that it is N- (ethoxymethyl) -2'-isobutoxy-6'-ethyl-2-chloroacetanilide. 8. A compound according to claim 3, characterized in that it is N- (allyloxymethyl) -2'-isobutoxy-6'-ethyl-2 - chloroacetanilide. 9. A compound according to claim 2, characterized in that it is N- (ethoxymethyl) -2'-n-butoxy-6'-isopropyl-2 - chloroacetanilide. 10. A compound according to claim 2, characterized in that it is N- (isobutoxymethyl) -2'-isopropoxy-6'-methyl - 2-chloroacetanilide. 11. A compound according to claim 2, characterized in that it is N- (isobutoxymethyl) -2'-n-propoxy-6'-methyl-2 - chloroacetanilide. 12. A compound according to claim 2, characterized in that it is N- (n-propoxymethyl) -2'-n-butoxy-6'-ethyl-2 - chloroacetanilide. 13. A compound according to claim 2, characterized in that it is N- (allyloxymethyl) -2'-n-butoxy-6'-ethyl-2-chloroacetanilide. 14. Herbicide preparation, characterized in that it means an adjuvant and a herbicidally effective amount of the ver; 15. Preparation according to claim 14, characterized in that in the compound R a C2-4 alkyl or Allyl radical and Rx are a C3 or C4 alkyl radical. 16. Preparation according to claim 15, characterized in that Rj is an isobutyl radical. 17. Preparation according to claim 16, characterized in that the compound N- (n-propoxymethyl) -2'-iso- butoxy-6'-methyl-2-chloroacetanilide. 18. Preparation according to spoke 16, characterized in that the compound is N- (isobutoxymethyl) -2'-iso-butoxy-6'-methyl-2-chloroacetanilide. 45 19. Preparation according to claim 16, characterized in that the compound is N- (isopropoxymethyl) -2'-iso-butoxy-6'-methyl-2-chloroacetanilide. 20. Preparation according to claim 16, characterized in that the compound N- (ethoxymethyl) -2'-isobutoxy- 50 is -6'-ethyl-2-chloroacetanilide. 20 Ri denotes methyl, n-propyl, isopropyl, n-butyl, isobutyl or isoamyl and R2 denotes methyl, ethyl or isopropyl, with the proviso that when R2 is isopropyl, R is ethyl and Ri is n-butyl-25; when R2 is ethyl, R is ethyl, n-propyl or allyl and Rj is n-butyl or isobutyl; when R is n-propyl, Rx is n-butyl or isobutyl; 3o when R is isopropyl, Rj is isobutyl; if R means isobutyl, R! represents n-propyl, isopropyl, isobutyl or isoamyl and when R represents butenyl, Rj represents methyl. 21. Preparation according to claim 16, characterized in that the compound is N- (allyloxymsthyl) -2'-iso-butoxy-6'-ethyl-2-chloroacetanilide. 22. Preparation according to claim 15, characterized in that the compound N- (ethoxymethyl) -2'-n-but- oxy-6'-isopropyl-2-chloroacetanilide. 23. Preparation according to claim 15, characterized in that the compound is N- (isobutoxymethyl) -2'-iso-propoxy-6'-methyl-2-chloroacetanilide. 60 24. Preparation according to claim 15, characterized in that the compound is N- (isobutoxymethyl) -2'-n - propoxy-6'-methyl-2-chloroacetanilide. 25. Preparation according to claim 15, characterized in that the compound N- (n-propoxymethyl) -2'- 65-n-butoxy-6'-ethyl-2-chloroacetanilide. 26. Preparation according to claim 15, characterized in that the compound is N- (allyloxymethyl) -2'-n-but-oxy-6'-ethyl-2-chloroacetanilide. 27. A method for controlling unwanted plants in crops, characterized in that a herbicidally effective amount of a compound of the formula is used for the location of the unwanted plants C1CH "C. OR is applied in which R represents ethyl, n-propyl, isopropyl, isobutyl, allyl or butenyl; Rj represents methyl, n-propyl, isopropyl, n-butyl, isobutyl or isoamyl; and R2 represents methyl, ethyl or isopropyl; with the proviso that when R2 is isopropyl, R is ethyl and Rx is n-butyl; when Rz is ethyl, R is ethyl, n-propyl or allyl and Rj is n-butyl or isobutyl; when R is n-propyl, Rt is n-butyl or isobutyl; when R is isopropyl, Rx is isobutyl; when R is isobutyl, R is n-propyl, isopropyl, isobutyl or isoamyl and, when R is butenyl, Rj is methyl. 28. The method according to claim 27, characterized in that the crop plants are sugar beets, soybeans, cotton, peanuts, bush beans, rapeseed, cucumber or tomatoes. 29. The method according to claim 28, characterized in that the crop plants are sugar beets. 30. The method according to claim 29, characterized in that in the compound R is a C2_4 alkyl or allyl radical and Rj is a C3 or C4 alkyl radical. 31. The method according to claim 30, characterized in that Rj is an isobutyl radical. 32. The method according to claim 31, characterized in that the compound is N- (n-propoxymethyl) -2'-isobutoxy - 6'-methyl-2-chloroacetanilide. 33. The method according to claim 31, characterized in that the compound is N- (isobutoxymethyl) -2'-isobutoxy - 6'-methyl-2-chloroacetanilide. 34. The method according to claim 31, characterized in that the compound is N- (isopropoxymethyl) -2'-isobut-oxy-6'-methyl-2-chloroacetanilide. 35. The method according to claim 31, characterized in that the compound is N- (ethoxymethyl) -2'-isobutoxy-6 '- ethyl-2-chloroacetanilide. 36. The method according to claim 31, characterized in that the compound is N- (allyloxymethyl) -2'-isobutoxy - 6'-ethyl-2-chloroacetanilide. 37. The method according to claim 30, characterized in that the compound is N- (ethoxymethyl) -2'-n-butoxy-6 '- isopropyl-2-chloroacetanilide. 38. The method according to claim 30, characterized in that the compound is N- (isobutoxymethyl) -2'-isopropoxy - 6'-methyl-2-chloroacetanilide. 39. The method according to claim 30, characterized in that the compound is N- (isobutoxymethyI) -2'-n-propoxy - 6'-methyl-2-chloroacetanilide. 40. The method according to claim 30, characterized in that the compound is N- (n-propoxymethyl) -2'-n-butoxy - 6'-ethyl-2-chloroacetanilide. 41. The method according to claim 30, characterized in that the compound is N- (Allyloxymethyl) -2'-n-butoxy - 6'-ethyl-2-chloroacetanilide. 42. The method according to spoke 27 for controlling undesirable plants in sugar beets, characterized in that a herbicidally effective amount of N- (n-propoxymethyl) -2'-isobutoxy-6'-methyl-2 - anilide is applied to the site thereof . 43. The method according to spoke 27 for controlling undesirable plants in sugar beets, characterized in that a herbicidally effective amount of N- (ethoxymethyl) -2'-isobutoxy-6'-ethyl-2-chloroacetanilide is applied to the site thereof. 44. The method according to any one of claims 27 to 43, characterized in that the undesirable plants are annual narrow-leafed weeds.