DE3110523A1 - 2-HALOGEN ACETANILIDES AND THEIR USE AS HERBICIDES - Google Patents

Description

DR. BERG DPPL.-ING. STXPF- _: DIPL.-ING. SCHWABE DR. DR, SANÜMAIK.

PATENT LAWYERS Poetfach 860245 8000 Munich 86 J I I U O Z 3

Lawyer files: 31 311 * - / f * f ~ f March 8, 1981

MONSANTO COMPANY iJT. LCHJl: S, .MISSOURI / U.S

2-Kalogenacetanilides and their use as herbicides

MO ») 91U 72 Telegr« mmo: ^ 30062/0660 BuiUnnien: Hypo-B »nk Munich« 10122850

9JI27J BEROSTAPFPATENT Munich (BLZ 7OOJ0OU) Swift Code HYPO DE MM

9ttm TELEXt " Biyet Veteinibink Munich 453100 (BLZ 70020270)

* »"> 0 05245 «BEROd Pmlicheck Munich i534J-8O8 (BLZ 70010OgO)

Description · '

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

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

The compounds according to the invention, which are characterized by a hydrocarbyloxymethyl radical on the anilide nitrogen, a trifluoromethyl radical in an ortho position, and a methyl radical or, in specific cases, an ethyl radical or hydrogen in the other ortho position, correspond, as far as known, most closely to those of BE PS 810 763. The most relevant descriptions in this patent are the general descriptions of N-alkoxyethyl or alkyl-substituted alkoxyethyl-2-chloroacetanilides, which may be substituted on the anilide ring in the ortho and meta positions with one or more radicals derived from a variety of radicals including halogen, alkyl, alkoxy or trifluoromethyl (-CF ₃ ). The list of connections

- / 15

130062/0660

-jit-

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

- / 16

; 0

Prove spectrum and harmlessness for the cultivated plants.

Other less relevant relevant publications than the aforementioned BE PS 810 763 include US Patents 3,966,811 and 4,152,137, German application 2 402 983, British application No. 2 013 188 and ZA-PS 74/0767. Although these references contain general descriptions of 2-haloacetanilides which, among other substituents, can also have “CF ₃ substitution on the anilide ring, the only descriptions of such types of compounds are found in US Pat. No. 3,966,811 and ZA-PS 74/0767. However, neither of these two patents contain, either generally or in particular, ortho-CF_-substituted compounds which would also be substituted in the other ortho position with a methyl or ethyl radical; the only -CF ^ -substituted compounds described in these patents are meta-CF_ -substituted compounds Furthermore, in both patents, as in the above-mentioned BE PS 810 76 3, there is a requirement that there be at least 2 carbon atoms between the anilide nitrogen and the oxygen of the alkoxy moiety, a condition which is prescribed in all of the above references is, with the exception of US Pat. No. 4,152,137, in which no -CFg -substituted compound at all gen are described.

- / 17

Of the relevant publications listed above, only BE PS 810 76 3 and ZA-PS 74/076 7 contain data for the herbicidal activity of N-alkoxyalkyl-2-haloacetanilides with -CF ₃ substitution on the anilide ring. However, this information is vague, inaccurate and incomplete. For example, BE PS 810 76 3 contains limited herbicide data for only one -CF ^ -substituted compound, namely compound no. (Which is the same compound as in Example 2), ie 2-trifluoromethyl-N- (2'-methoxyethyl) -2-chloroacetanilide. In Table III of BE PS 810 76 3 it is shown that compound no. 37 kills or seriously damages certain unidentified species of "Cuperus", Setaria, Digitaria and Echinochloa, with little damage to the weeds Avena fatua and an unidentified Lolium species in certain cultures. Since there is no precise identification of 5 of the 6 weeds tested, a meaningful assessment of the herbicidal effectiveness of the compound 37 is not possible.

Audi ZA-PS 7M / O767 contains only limited herbicide data for only one -CF ₃ -substituted compound, namely compound no. 78, ie 2,6-dimethyl-3-trifluoromethyl-N- (2'-methoxyethyl) -N -2-chloroacetanilide. The only herbicidal data for this compound is found in Example 5, which is stated to show very strong growth inhibition in U species of grass weeds. However, no laboratory or field test data are published on the effect of Compound No. 7 8 in a culture, including whether this compound is a

130062/0660 ~ ^{/ 18}

shows selective control of a weed in a crop, making meaningful evaluation of that compound impossible. The relevant references listed above describe the herbicidal effectiveness against a large number of weeds, but they do not give any data for -CF ₃ -SUbStI-tuierte N-alkoxyalkyl compounds which additionally and / or simultaneously control or control perennial weeds which are difficult to kill in one or more crops push back, such as couch grass, yellow or purple sedge (Cyperaceae), as well as a broad spectrum of annual weeds, including annual weeds that are difficult to kill, such as Sorghum halepense seedlings, Sorghum bicolor, Brachiaria plantaginea, Panicum species (texanum and miliaceum), Oryza Rottboellia exaltata, while they also control or push back other harmful perennial and annual weeds, for example Herbstpanicum, Polygonum sp., Chenopodium album, Amaranthus, foxtails (e.g. Setaria faberi and lutescens), Digitaria sanguinalis, Echinochloa crus-galli, Ipomoea sp. , Abutilon theophrasti, Xanthium pensylvanicum, Portulac, Se sbania exaltata, Sida spinosa etc.

An extremely useful and desirable property of herbicides is the ability to control weeds for an extended period of time Keeping it under control, the longer during each growing season, the better. With many known herbicides

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130062/0660

Adequate weed control is only achieved for 2 to 3 weeks, in some very good cases maybe up to H to 6 weeks before the chemical becomes phytotoxic ^ Loses effectiveness. A disadvantage of most of the known herbicides is their relatively short lifespan in the soil.

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

Another disadvantage of many known herbicides is the limitation their applicability to certain types of soil, i.e., while some herbicides are found in soils with little organic Proportionately effective, they are highly organic in other soils Part ineffective, or vice versa. It is therefore advantageous when a herbicide is used in all types of soil from slightly organic Soils up to heavy clays and peat soils can be used.

Another disadvantage of many known herbicides is the limitation to a particularly effective mode of application, i.e. application on the surface before emergence or working into the soil, application before and / or after planting. The ability to apply a herbicide in any way, by applying it to the surface or

- / 20 130062/0660

Working into the ground is very desirable.

Finally, a disadvantage of some herbicides is the need to be specific because of their toxicity Must take precautions for their handling. A herbicide should therefore also be safe to use.

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

The invention provides herbicides which control and / or suppress difficult-to-kill perennial and annual weeds, as described above, while remaining harmless to a large number of crops, especially maize and soybeans, but also others, including cotton, Peanuts, canola, French beans, wheat and / or sorghum.

A further object of the invention is to maintain the herbicidal activity in the soil for periods of up to 12 weeks.

The invention also relates to herbicides that are effective against leaching or dilution at high humidity, e.g.

- / 21

Rains, are persistent.

The invention further relates to herbicides which are effective in a wide range of soils, from light to soil medium organic soils to heavy clays or Peat earth.

Another advantage of the herbicides according to the invention is that they can be used flexibly, for example by application on the surface before emergence or by working it into the ground. Finally, the herbicides of the invention have the advantage that they are harmless and do not require any special handling precautions. From the These and other objects of the invention will become more apparent from the following detailed descriptions.

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

It has now been found that a selective group of 2-haloacetanilides formed by specific combinations of specific hydrocarbyloxymethyl radicals on the anilide nitrogen atom, a trifluoromethyl radical (-CF ₃ ) in one ortho position, and a methyl or ethyl radical or hydrogen atom in the other ortho position Position marked

- / 22

• T30062 / 0660

are, unexpectedly superior and excellent herbicidal properties compared to known herbicides including closely related and known homologous compounds own.

An essential property of the herbicide preparations according to the invention is their ability to control a wide range of weeds. These include weeds, that can be controlled by common herbicides, as well as a variety of weeds that individually or collectively so far escaped control by a single class of known herbicides. Are at the same time they are harmless to crops of one or more crops, including in particular maize and soybeans, but also others such as cotton, peanuts, canola, sorghum, wheat and French beans. While the known herbicides for Control of a number of weeds and occasionally certain resistant weeds have been shown to be useful The unique herbicides of the invention are found to be able to cure a wide variety of resistant perennials and annuals To control weeds or to push them back to a large extent, so the perennial weeds couch grass, yellow and purple Sedge (Cyperaceae), annual broad-leaved weeds such as Sida spinosa, Sesbania exaltata, Polygonum sp., Chenopodium album, Amaranthus, and annual grasses such as Sorghum halepense seedlings, Sorghum bicolor, Brachiaria plantaginea, Panicum texanum, Panicum miliaceum, Oryza sativa,

- / 23

-2Ί ~

Rottboellia exaltata, as well as other harmful weeds such as Herbstpanicum, Foxtails, Echinochloa crus-galli, Digitaria sanguinalis, etc. An improved weed reduction has also been found in resistant weeds such as Ambrosiaceae, Abutilon theophrasti, Ipomoea sp., Xanthium pensylvanicum, Portulac, etc. achieved.

The compounds of the invention are represented by the formula

C1CH _? C .CH ₂ OR

_{characterized in which R 1 is} alkyl or alkoxyalkyl or alkenyl or alkynyl with up to 5 carbon atoms and R 1 is hydrogen, methyl or ethyl; with the proviso that,

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

Preferred compounds according to the invention are those in which R .. in the above formula is methyl or ethyl and R is a C _2-1 , alkyl radical. Individual preferred compounds according to the invention are the following:

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130082/0660

- OS-

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

anilide,

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

acetanilide,

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

acetanilide,

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

acetanilide,

N- (ethoxymethyl) -2 ^l -trifluoromethyl-6'-ethyl-2-chloroacet-

anilide,

N- (n-propoxymethyl) -2'-trifluoromethyl-6 ^l -methyl-2-chloro-

acetanilide,

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

acetanilide.

Further compounds of the invention are described below.

The usefulness of the compounds according to the invention as active ingredients in the herbicide preparations produced therewith> and the method of application are described below.

The compounds according to the invention can, as in Example 1 described by N-alkylation of the anion of the appropriate secondary 2-haloacetanilide with an alkylating agent can be produced under basic conditions. A modification of the N-alkylation process sees the in situ - / 95

-U-

Manufacture of Halogenmethylalky lethern before that as starting materials used in said N-alkylation process; it is in Example 2 for manufacture a further type of compounds according to the invention described.

example 1

This example describes the preparation of N- (ethoxymethyl) -2 ^l -trifluoromethyl-6'-methyl-2-chloroacetanilide.

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

- / 26

Ethyl acetate in cyclohexane was used. More Kugelrohr distillation of peak fraction gave 3.2 g (6 5% yield) of colorless oil, b.p. 100-110 ⁰ C at 0.1 mm Hg. on standing crystallized a white solid, mp. 41-43 ⁰ C, out.

Elemental analysis for C ₁ 2H ₁₅ ClF ₃ NO ₂ (%): Calculated: C: 50.41; H: 4.88; N: 4.52; Found: C: 50.02; H: 4.81; N: 4.38.

Example 2

This example describes the use of an improved alternative method by which the inventive Connections can be made. A peculiarity of this process is the in situ production of the alkylating agent, making the process more effective, economical and simpler.

A slurry of 7.3 grams (0.096 moles) of ethylene glycol monomethyl ether and 1.44 g (0.048 mol) of paraformaldehyde in 100 ml of methylene chloride solvent was cooled in an ice water bath and 5.9 g (0.048 mol) of acetyl bromide were added. After stirring for 45 minutes, 4.0 g (0.016 mol) of 2'-trifluoromethyl-6'-methyl-2-chloroacetanilide were obtained and 2.0 g of benzyl triethylammonium chloride admitted. Then 50 ml of 50% NaOH were added all at once. Gas chromatography showed that the Reaction was complete in about 5 minutes. To the mixture was

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13G062 / Q660

added to the ice and water to effect phase separation, the organic phase was then separated, dried, filtered off and stripped. The residue was distilled in vacuo to give 4.2 g (7 7% yield) of a clear colorless oil, bp. 150-160 ⁰ C at 0.05 mm Hg.
_{Elemental Analysis} for C 11+ H ₁₇ ClF ₃ NO ₃ ( ¹ U: Calculated: C: 49.49; H: 5.04; N: 4.12; Found: C: 49.3-3; H: 5.04; N: 4.08.

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

Leaving the N-alkylation process too high or too low Develop temperatures, then various impurities can arise, e.g. secondary anilide, the corresponding imidate, α-alkoxyamide or diketopiperazines. Such impurities can be removed by washing out the organic layer with a dilute aqueous hydrochloric acid solution, e.g. 2-3% NaCl or 5% HCl.

Examples 3 to 13

It was practically the same, under example 1 or 2 The procedures, amounts of reactants and general conditions described were used, but each was suitable secondary starting anilides and alkylating agents used to produce the end product, namely further inventive

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130062/0660

-23-

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

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130062/0660

Table I. Elemental analysis

Ex.
No.

link

Empirical formula

Kp. C EIe- (me. Hg) ment

Be accounted for

N- (isppropoxymethyl) -2'-tri-

fluoromethyl-2-chloroacet-

anilide

N- (n-Prop.oxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide

N- (isopropoxymethyl) -2'-trifluorine, ethyl-6 '-methyl-2-chloroacetanilide

N- (isobutoxymethyl) -2'-tri- C. fluoromethyl-6'-methy1-2-chloroacetanilide

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

N- (n-butoxymethyl) -2'-tri- (fluoromethyl-6 ^J -methy1-2-chloroacetanilide

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

C ₁₃ H ₁₅ F ₃ ClNO ₂

₁ H ₁ -ClF-NO ^{17 3}

C ₁₄ H ₁₇ ClF ₃ NO ₂

C ₁₉ H ₁ -ClF, NO.

₁ "C1F.N0,

100-101
(0.05)

110-120
(0.1)

110-120
(0.1)

130-140
(0.1)

C.
H
N

C.
H
N

C.
H
N

C.
H
N

135-138
(0.05)

135-142
<0.05)

C.
H

H
N

50.41
4.88
4.52

51.94
5.29
4.33

51.94
5.29
4.33

53.34
5.67
4.15

C. 48 , 47 H 4th , 43 N 4th , 74

53.34
5.67
4.15

53.34
5.67
4.15

50.52 4.89 4.46

51.80 5.17 4, 28

51.69 5.23 4.22

53.07 5.61 4.01

49.94 4.44 4.70

53.32 5.68

4.14

53.23 5.67 4, 13

Uf

CO

Table I. Elemental analysis

Ex.

No.

10

Link.

N- (Allyloxymethyl) -2'-trifluoromethyl-6 ^f -methyl-2-chloroacetanilide

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

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

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

N- (n-Propoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide

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

Loading

Empirical Kp. ⁰ C EIe- calc- fun formula (mm Hg) ment net den

C ₁₁₁ H ₁₁ -ClF-NO, 123-125 C
15 ei 2 _{(01) H.}

C ₁₁₁ H ₁₃ ClF ^ NO

Oil C
j. η j. ο ο e. _u

C ₁ -H ₉₁ ClF-NO ₉ 150 C

^{ίλ ä l} (0.05) H

C ₁ H ₁₇ ClF ^ NO ₉ 133-135 C
^{X / l} (0.02) H

C ₁₁ -H ₁₀ ClF-JNO- colorless- C
^{lb 19 ό 2} ses oil H

C ₁₁ -H ClF ^ NO 100-105 C
^{ä J} (0.01) H

52.27 4.70 4.35

52.59 4.10 4.38

54.63 6.02 3.98

51.94 5.29 4.33

53.34 5.67 4.15

53.34 5.67 4.15

52.11 4.74 4.34

52.44 4.14 4.34

54.66 6.03 4.00

51.32 5.26 4.39

53.74 5.77 4.16

53.43

5.74 4.18

co

-3S.-

For the preparation of the compounds according to the invention as Secondary anilides used as starting material are best obtained with conventional chloractylation of the appropriate primary amine prepared as described in Example 14.

Example IU

The production of the secondary anilide is described here, which is used as a starting material for the production of a Compound, i.e. the compound of Example 13 is used.

6.0 g (0.03174 mol) of 2-trifluoromethyl-6-ethylaniline were dissolved in 75 ml of toluene and 3.77 g (0.033 mol) of chloroacetyl chloride were carefully added. The resulting slurry was heated to reflux temperature and held there for 4 hours. Then the mixture was diluted with an equal amount of hexane, then the mixture was allowed to stand. The product crystallized out and the solid obtained was filtered off and air-dried to give 5.8 g (69% yield); the filtrate was stripped to give an additional 2.7 g of white solid, mp. 121-124 ⁰ C (sealed tube).

Elemental Analysis for C ₁₁ H ₁₁ ClF ₃ NO (%): Calculated: C: 49.73; H: 4.17; N: 5.27; Found: C: 49.36; H: 4.09; N: 5.38.

The product was found to be 2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide identified. - / 32

130062/0660

Primary amines of the kind used to make secondary anilides by haloacetylation, such as as described above are known in the literature; See, for example, U.S. Patent 3,966,811 and U.S. Patent No. 3,966,811, cited above British Application No. 2 013 188.

The compounds of the invention were found to be effective Herbicides, especially as pre-emergence herbicides, although post-emergence activity has also been demonstrated. The pre-emergence tests referred to here include both greenhouse and field tests. In the greenhouse tests, the herbicide is either used after planting the seed or offshoot applied to the surface, or incorporated into a certain amount of soil, which is spread as a top layer over the test seeds in sown test containers will. In field tests, the herbicide can either be incorporated into the soil before planting ("P.P.I."), that is, the herbicide is applied to the surface of the earth, then mixed in, then the cultivation seeds sown, or the herbicide is applied to the surface ("S.A.") after the crop seeds are planted are.

The surface test method used in the greenhouse ("S.A.") is carried out as follows: Container, e.g. aluminum pans with about 2Mxl3x7 cm, or

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130082/0660

Plastic pots with about 9.5x9.5x8 cm, with drainage holes in the Soil, are filled to the brim with Ray silt loam, which is then pounded down to a height of 1.3 cm below the edge of the pot. The pots will then come with a The plant species to be tested was sown and covered with a 1.3 cm high layer of the test soil. The herbicide is then applied e.g.

applied to the surface of the earth with a belt sprayer

2
(187 l / ha, 2.11 kgf / cm); each pot then receives 0.64 cm of water from above. Then the pots are placed on greenhouse tables and watered from below as required. In another possible method, watering from above can also be omitted. The herbicidal effects are assessed about 3 weeks after the treatment.

The herbicide treatment by working into the soil CS.I. ") takes place in greenhouse tests as follows: Good topsoil is placed in aluminum pans and pounded down to 1 to 1.3 cm below the edge. A number of seeds or cuttings of various kinds of plants are placed on the earth. The one to fill up completely soil necessary for the pans after sowing or planting is weighed into a pan. The earth 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. Received after treatment the pans an initial watering from above,

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130062/0660

which corresponds to 0.6 * 4 cm of rain, then they will be as needed watered from below so there is adequate moisture for germination and growth. The watering from above can also be omitted. Observation takes place about 2 to 3 weeks after sowing and treatment.

The results of the tests are summarized in Tables II and III, which were carried out to increase the herbicidal pre-emergence activity of the compounds of the invention determine; in these tests, the herbicides were worked into the soil and watered only from below. The evaluation of the herbicidal activity was obtained using a fixed scale based on the percentage of damage to each plant species. The ratings are defined as follows:

% Control valuation 0-24 0 25 - 49 1 50-74 2 75-100 3 indefinite 5

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

A Canada Thistle Cirsium arvense

B Cocklebur Xanthium

pensylvanicum

C Velvetleaf Abutilon theophrasti

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130062/0660

D Moraingglory bindweed Ipomoea sp.

E Lambsquarters report Chenopodium album

F Smartweed Polygonum sp.

G Yellow Nutsedge Cyperus esculentus

H Quackgrass couch grass Agropyrum repens

I Johnsongrass Sorghum halepense

J Downy Brome fluffy brindle, Bromus tectorum

K Barnyardgrass Echinochloa

crus-galli

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130062/0660

kg / ha Tabel II B. C. D. P. Plant species
FGHIJ 3
3 3
3 3
3 3
3 K 11.2
5.6 3
2 3
2 3
3 3
3 3
3 3
0 3
2 3
2 3
3 3
3 Connection of
Example No. 11.2
5.6 1
2 1
1 3
3 2
2 2
3 ' 3
3 3
3 2
1 3
3 3
3 1 11.2
5.6 Pre-emergence test 1
0 2
2 3
3 3
3 3
2 3
3 3
3 3
3 3
3 3
3 2 11.2
5.6 Λ 3
2 2
1 3
2 3
3 3
3 3
3 3
3 3
1 3
3 3
3 3 11.2
5.6 5
5 3
0 2
0 3
3 3
3 3
3 3
3 3
3 3
3 3
3 3
3 4th 11.2 2
3 2
2 1
0 3
1 3
3 3
3 2
2 3
3 1
1 3
3 3
3 5 - 11.2
5.6 3
2 1
0 2
1 2
1 3
3 0
0 3
3 3
3 3
2 3
3 3
3 6th 11.2
5.6 5
5 2
1 0
0 2
3 3
3 3
3 3
3 3
3 3
1 3
3 3
3 7th 11.2
5.6 5
5 2
2 2
1 3
2 3
3 3
3 3
3 3
3 3
0 3
3 3
3 8th 11.2
5.6 5
5 2
1 1
1 3
2 3
3 3
3 3
1 3
3 0
1 3
3 3
3 9 11.2
5.5 3
1 1
1 1
1 3
2 3
3 3
3 3
3 3
3 0
3 3
3 3
3 10 11.2
5.6 3
3 2
1 0
0 2
2 3
1 3
2 3
3 3
3 3
2 3
3 3
3 11 11.2
5.6 3
3 2 2
2 3
3 3
3 3
3 3
3 12th 3
3 13th 3
3 3
3 3
3

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130062/0660

- -97- -

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

Soybeans

Sugar beet

wheat

rice

Sorghum

L soybean

M sugarbeet

N Wheat

O Rice

P sorghum

B Cocklebur

Q Wild Buckwheat Morning Glory Knotweed

D Morningglory

R Hemp sesbania

E Lambsquarters report

F Smartweed

C Velvetleaf

J Downy brome downy brome

S Panicum species

K Barnyardgrass

T Crabgrass

Xanthium pensylvanicum Polygonum convulvulus Ipomoea sp.
Sesbania exaltata Chenopodium album Polygonum sp.
Abutilon theophrasti Bromus tectorum Panicum spp.
Echinochloa crus-galli Digitaria sanguinalis

The results are shown in Table III.

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kg / ha Tabel III M. N 0 P. B. ο Plant species R. 3 F. C. J S. K T 5 ^ 6 2 3 3 3 0 3 3 3 3 2 3 3 3 3 1.12 1 1 2 3 0 1 D. 2 2 2 0 3 3 3 3 Connection of 0.23 Pre-emergence test 1 0 2 1 0 1 3 3 1 3 0 2 3 3 3 Example No. 0.055 0 0 0 0 0 0 2 1 1 1 0 0 2 2 3 1 0.0112 0 0 0 0 0 0 0 0 3 1 0 0 1 2 2 5.6 L. 3 2 3 3 1 2 0 3 2 3 0 3 3 • ^ 5 1 32 1 3 2 3 2 0 1 0 1 1 2 0 3 3 3 5 0.28 0 2 0 1 1 0 0 3 1 0 0 3 3 3 5 0 3 2 0 1 0 1 0 0

0.055 01000 00000001135 0.0112 0 000 0 00000000015

1.12 0.28 0.05

0333313333313333 0113310313 003333

0002200003001333 0001 000002300333 0.0112 00000000 0 1 0 0 0 3 3 3

0.0055 00000000

03000101

5-6 2333323333313333

1.12 1323313233313333

0.28 0122101013302333

0.055 01112210 2 1100223

0.0112 0 10 0 0 0 0 00 10 0 0 3 3 3

12333133 33313333 02233020233 0 3333 0 2 13322323303333 20 13102333 003 10123 3

5.6

1.12 0.28 0.05Π 0 10 12 1 0.0112 0 10 0 0 11

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130083/0860

ι 10 kg / ha ■ Ί0 III- continuation M. N 0 P. B. Q 3110523 R. E. F. C. J S. K T 5.6 Pre-emergence test 3 3 3 3 2 3 3 3 3 1 3 3 3 3 1.12 1 0 3 3 1 3 1 3 3 0 3 3 3 3 0.28 L. 2 0 2 2 2 2 Plant species 3 3 3 0 3 3 3 3 Verb, from 0.055 Tabel 1 2 0 1 2 1 2 D. 2 3 1 0 2 3 3 3 Example No. 11 0.0112 0 2 0 1 0 2 2 3 2 3 1 0 1 1 3 3 S. 5.6 0 3 2 2 3 0 2 3 2 3 0 0 3 3 3 3 1.12 0 1 0 0 1 0 1 1 0 2 0 0 C. 2 3 3 0128 0 0 0 0 0 0 1 2 0 0 0 0 0 2 2 3 0.056 0 1 0 1 0 0 0 2 0 3 2 0 0 0 2 3 12th 5.6 0 3 3 3 3 2 3 2 3 3 3 1 3 3 3 3 7 · 1 12 0 2 3 3 3 0 2 0 1 3 3 0 3 3 3 3 0.28 0 1 2 1 2 0 2 2 2 1 1 0 2 3 3 3 0.055 2 0 1 1 1 0 0 0 0 1 1 0 1 3 3 3 13th 0.0112 1 0 0 C. 0 1 0 3 1 0 0 0 1 0 2 3 8th 5.5 0 2 3 3 3 2 3 0 3 2 3 1 3 3 3 3 1.12 0 2 3 3 1 1 3 0 2 2 2 0 3 3 3 3 0.2ß 1 2 2 3 2 0 1 0 2 1 1 0 3 3 3 3 0.055 2 0 0 0 0 0 0 0 0 2 1 0 2 3 3 3 0.0112 1 0 0 0 0 0 0 3 0 0 0 0 0 0 3 3 9 5.6 1 3 3 3 3 2 3 1 3 3 3 0 3 3 3 3 1.12 0 2 3 3 3 0 3 1 2 2 3 0 3 3 3 3 0 ₇ 28 0 2 2 2 2 0 1 0 2 3 2 0 3 3 3 3 0.055 3 1 0 1 0 0 0 0 1 0 0 0 0 3 3 3 0.0112 1 0 0 0 0 0 0 3 0 0 0 0 0 1 2 3 5.5 0 3 3 3 3 1 3 3 3 3 3 1 3 3 3 5 1.12 0 3 1 3 1 1 1 0 1 2 2 0 3 3 3 5 0 28 0 2 1 2 1 0 0 0 1 1 1 0 3 3 3 5 0.055 0 1 0 0 0 0 0 0 5 0 0 0 1 2 3 5 0.0112 0 1 0 0 0 0 0 3 0 0 0 0 0 1 3 5 5.6 0 2 2 3 3 1 2 2 0 2 1 0 3 3 3 3 1Ϊ12 0 2 1 2 3 0 2 0 1 2 2 0 3 3 3 3 0.28 0 1 0 1 0 0 1 0 0 1 0 0 1 2 3 2 O ₇ O56 1 5 0 0 0 0 5 0 0 0 0 0 0 0 2 0 5.6 1 3 3 3 3 2 ' 3 2 3 3 3 2 3 3 3 3 1 12 0 2 3 3 3 0 2 2 3 2 3 0 3 3 3 3 0.28 0 2 3 3 1 0 1 0 3 1 3 0 3 3 3 3 0.055 2 1 1 1 0 0 1 0 0 0 0 0 2 3 3 3 1 3 2 2 0 0 0

0.0112 000000001 5500022

13QQ62 / 0660 ~ ^A0

It has been found that the herbicides of the invention are unexpected superior properties as pre-emergence herbicides own, especially in the selective control of difficult-to-kill perennial and annual weeds, including perennial weeds such as couch grass, yellow and purple sedge (Cyperaceae), annual broad-leaved ones Weeds such as Sida spinosa, Sesbania exaltata, Polygonum sp., Chenopodium album, Amaranthus and annual grasses such as Sorghum bicolor, Brachiaria plantaginea, Sorghum halepense, Panicum texanum, Panicum miliaceum, Oryza sativa, Rottboellia exaltata, foxtails (e.g. Setaria veridi s, lutescens and faberi), Echinochloa crus-galli and Digitaria sanguinalis. There was also a decrease in other resistant species of the weed population, e.g. Ambrosiaceae, Abutilon theophrasti, Ipomoea sp., Xanthium pensylvanicum, Portulac etc.

Selective control and increased suppression of the above-mentioned weeds with the aid of the herbicides according to the invention has been found in, a wide variety of crops of useful crops, including corn and soybeans of particular interest, but also others such as cotton, peanuts, rapeseed, French beans, wheat, and sorghum; these last two crops are usually less tolerant of those of the invention Herbicides as other of the crop plants mentioned; this reduced tolerance can be achieved through the use of protective agents, e.g., herbicidal antidotes.

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130062/0860

In the following discussion of the data, reference will be made to herbicide _{application rates represented by "GR ^ 5} ¹ 'and" GRgj. "These amounts are given in kg / ha, this value can be obtained by dividing by 1.12 in lbs / A are converted. GR ₁₅ defines the maximum amount of herbicide, at 15% or less of crop damage occurring in the while GR _SST. the minimum necessary amount, at which a 85% inhibition of weeds is achieved. the GR _1, .- and GR ", - quantities are used as a measure of the possible performance of commercially available products, it being understood that 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 on 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 GR., _C / GR _OC , ie GR ₁₅ ~ amount for the crop divided by the GR _fi amount for the weeds , both amounts in kg / ha. In the tables below, the selectivity factors are given in brackets after the GR-g amount for each weed; "NS" means "non-selective"; insignificant or indeterminate selectivity is indicated with a dash (-).

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130062/0660

Because crop tolerance and weed control are related to each other are related, eat a brief discussion of that relationship, expressed as a selectivity factor. In general, it is desirable that the harmless factors for the crop, i.e. the herbicide tolerance values of the crop, are high, since the for one reason or another, higher herbicide concentrations are often desired. Conversely, the quantities for Weed control should be small for economic and possibly environmental reasons, i.e. the herbicide should be one have high unit activity. However, small application rates of a herbicide may not be intended for control purposes Weeds enough and a larger amount is needed. The best herbicides are therefore the ones that come with control the greatest number of weeds and the greatest possible harmlessness to the Crop, i.e. crop tolerance, provide. The selectivity factors (defined above) are therefore used to quantify the relationship between harmlessness to the crop and control of weeds. The following applies to the selectivity factors specified in the tables: the higher the numerical value, the greater the urriHo Selectivity of the herbicide for weed control in a given Culture.

To the unexpectedly superior properties of the compounds according to the invention on both absolute and relative

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130062/0660

- 14 - "

On a tive basis, comparative tests were carried out in the greenhouse performed with known compounds that are in their chemical Structure are most closely related to the compounds of the invention. These known compounds are like is identified as follows (the same nomenclature is used as for the compounds according to the invention):

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

B. N- (ethoxyethyl) -2'-trifluoromethyl-2-chloroacetanilide.

Tables IV and V provide data for pre-emergence herbicidal activity 'compiled with which the relative Effectiveness of the compounds according to the invention and the known compounds as selective herbicides against the resistant ones and pesky perennial weeds, couch grass and Cyperus esculentus in soybeans and corn, respectively. These Weeds are usually associated with such larger crops as corn and soybeans. The test data in the tables IV and V were obtained under identical conditions and represent the average of 2 runs (except Compound of Example 13, which was only used in a comparative test). The testing procedure was the same as it for Tables II and III, one modification consisted of an initial watering from above, which corresponded to 1 inch of rain; the subsequent irrigation took place from below. "NS" means non-selective within the test limits.

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130062/0660

Table IV

(kg / ha) (kß / ha)

A. 1 > 2.24 B. 3 1.96 Ex. 4th 2.67 Ex. 5 1.68 Ex. 13th 1.12 Ex. 1.46 Ex. 2.13

Compound soybean couch grass Cyperus esculentus

> 2.39 (NS) 1.13 (1.98)

0. bl (3.21) 0.44 (4.45)

0.17 (15.6) 0.17 (15.6)

0.27 (6.22) 0.19 (8.84)

0.13 (8.62) 0.17 (6.59)

0.26 (5.62) 0.26 (5.62)

0.20 (10.65) 0.17 (12.53)

From Table IV it can be seen that each compound of the invention significantly higher selectivity factors (values in brackets) than the known compounds. In particular it should be noted that the unit activities (relative phytotoxicity per herbicide unit) of the invention Connections was noticeably higher compared to couch grass and Cyperus esculentus than those of the known compounds, while the harmlessness for the cultivated plants was retained. Particularly noteworthy are the extraordinary high selectivity factors of the compounds of Examples 1 and B.

Further comparative data, which the effectiveness of the invention Compounds in comparison to the above known

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130062/0660

The th compounds against couch grass and Cyperus esculentus in maize are summarized in Table V.

1 GR, .- quantity
(kg / ha) Tabel V GR _g5 amount
(kg / ha) (NS) 1.13 esculentus 3 Corn (1.33) 0.44 (1.98) 4th > 2.24 Couch grass (4.47) 0.17 (1.84) 5 0.81 > 2.39 Cyperus (7.19) 0.19 (4.47) link 13th 0.76 0.61 (5.85) 0.17 (10.2) A. 1.94 . 0.17 (7.04) 0.26 (4.47) B. 0.76 0.27 (11.2) 0.17 (7.04) Ex. 1.83 0.13 (13.18) Ex. 2.24 0.26 Ex. 0.20 Ex. Ex.

From Table V it can be seen that each compound of the invention significantly higher selectivity factors compared to couch grass and Cyperus esculentus in maize as the known compounds. It can again be stated that the unit activities of the compounds according to the invention against couch grass and Cyperus esculentus were markedly higher than those of the known compounds, while being innocuous for the culture was preserved. Particular attention should be paid to the high selectivity factors for the compounds of Example 3, 5 and 13, especially in comparison with those of the known ones Links.

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130062/0660

From the comparative data in Tables IV and V it can be seen that the compounds according to the invention are extraordinary higher and unexpectedly superior herbicidal effectiveness compared to the resistant perennial weeds couch grass and Cyperus esculentus in two main crops, i.e. soybeans and maize, showed, as compounds A and B, which are the most closely related of the known compounds.

Data from further pre-emergence tests also indicated that the Compounds according to the invention also couch grass, Cyperus esculentus and / or other weeds in one or more crops of cotton, peanuts, French beans, wheat, sorghum and / or selectively inspect rapeseed. For example, Table VI summarizes data showing herbicidal selectivity of the compounds of Examples 1 and 3 show against couch grass in rapeseed, French beans, sorghum and wheat. Provided nothing else is noted, the herbicide was incorporated into the soil for the greenhouse tests in Table VI and other tables, and after an initial top watering, bottom watering was done as described above is.

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130062/0680

Table VI

GR.g-Kenge
(kg / ha )

GR quantity (kg / ha)

Compound canola French beans sorghum wheat

Ex. 1 0.86 Ex. 3 1.9

0.90

2.24

Couch grass

0.12 (7.2)

0.12 (7.5)

0.24 - 0.12 (2.0)

0.21 0.12 (1.8)

0.28 (6.8)

0.28 (8.0)

0.84-0.28 (3.0)

0.28 0.28 (1.0)

The compound of Example 1 was also tested in the field for its pre-emergence selectivity towards foxtail Species, Echinochloa crus-galli and Panlcum miliaceum in to identify multiple cultures. The data (obtained from three runs) are in Table VII for both the application on the surface (S.A.) as well as for the incorporation into the soil (PPI, i.e. incorporation before planting) of the herbicide listed. The seeds were placed in a fine silt loam seedbed with medium moisture at a depth planted by 2 inches. The first rain (0.51 cm) fell that day after treatment, the second rain (0.64 cm) two days after treatment; the total rainfall 2 2 days after the Treatment was 4.5 7 cm. The assessment took place 6 weeks after the treatment.

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Example 1

0 lot Field cutie pie Table VII Earth % flaming Sorghum bush Rapeseed Fox Echi- Panicum I. 1 (kg / ha) inais Corn nuts 0 beans 0 tail no- milia- f
I ι To whom- 2 , 56 0 0 0 tree 3 0 0 soecies chloa ceum (P manic 4th , 12 0 0 soy 0 wool 17th 8th 5 62 63 63 P. , 24 0 7th beans 8th 0 77 20th 33 92 93 83 1 , 48 15th 27 0 22nd 13th 32 32 0 93 93 95 2 , 56 0 0 5 17th 20th 53 23 0 98 98 97 4th , 12 0 3 0 13th 25th 92 10 15th 75 75 23 j proceed 24 5 27 13th 15th 13th 98 37 40 90 93 58 S.A. , 48 32 40 5 28 32 43 98 98 80 7th 37 100 100 85 20th 82 40 P.P.I.

Table VII shows that the compound of Example 1 generally performed better as a selective herbicide when it was applied to the surface as if it were incorporated into the ground. In the surface tests the herbicide selectively controlled the three tested weeds at application rates above 0.5-8 kg / ha while it for the crops field maize and soybeans up to 4.48 kg / ha remained harmless (i.e. up to about 15% maximum Damage); for sweet maize, peanuts and rapeseed the harmlessness was maintained up to over 2.24 kg / ha, for For cotton, sorghum and French beans it was just under 2.2U kg / ha. In the PPI tests, the compound controlled • from Example 1 selectively the foxtail species and Echinochloa crus-galli with less than 1.12 kg / ha, while the harmlessness for field maize, peanuts and rape in quantities up to 2.2U kg / ha, and for soybeans at quantities just below 2.24 kg / ha was retained.

Further field test data for the compound of Example 1 indicated selective pre-emergence control of other weeds in Soybeans, corn, cotton and / or peanuts; these included purple sedge, Setaria faberi and lutescens, Melde, Ipomoea, Xanthium pensylvanicum, Abutilon theophrasti, Polygonum pensylvanicum, Sida spinosa, Portulac, Digitaria sanguinalis, bedstraw, Panicum texanum, Richardia scabra, and / or Acanthospermum hispidum. Of course you can

- / 50

130082/0660

not all weeds mentioned are selectively controlled in all crops mentioned under all climatic, soil, moisture and / or application conditions. Selectivity data for the control of the above weeds in soybeans, corn, cotton and peanuts from a variety of field tests at different locations under different conditions of soil, moisture, etc. are shown collectively in Tables VIII-XI. In the. Tables, "WAT" means "weeks after treatment" of the plants with the herbicide, either applied to the surface ("SA") or incorporated into the soil before planting ("PPI"); the application rate for each crop / weed combination is given as GR .. or GR amount (as defined above). The GR ₁ ,. / GR ₈ ratio gives the selectivity factor "SF";"NS" means non-selective, and a dash (-) indicates insignificant or indeterminate selectivity, for example because the actual GR-I ₅ ^"nd GRg ₅ ~ amounts were or higher lower than the maximum or minimum amounts" in the In Tables VIII to XI, a vacancy means that the plant species was not present in a particular test plot, or that the data was not obtained, or that it was less significant than other available data, e.g. some 3 were omitted WAT observations in favor of 6 WAT data, or 6 WAT data were made

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130062/0680

- -S4- omitted, because the 3 WAT dates were definitive.

Tabel P.P.I. VIII G> K " _r / GK _no
15 85 S.F. Cultivated plant /
Connect-weed-
dunp. Combination' To whom
manic
procedure SA
PPI WAT > 4, 48 / <l, 12 C ^ U 0} Example l soybeans / SA
. Setaria faberi SA
PPI 3
5 > M, 48 / <1.12
> 4.48 / <1.12 P.P.I. 3
5
8th 2.52 / 2.8 (NS) Soybeans /
Setaria
lutescens 6th
6th 2.52 / 2.52
1.4 / 2.8 (1.0)
(NS) Soybeans /
Report 6th
6th 4.1 + 8 / 2.52 (1.8) Soybeans /
Polygonum
pensylvanicum 8th

The data in Table VIII show that this is the case. the connection of Example 1 selectively Setaria lutescens and faberi, Melde and Polygonum pensylvanicum in soybeans from 6 to 8 WAT either with the S.A. or the P.P.I. Process controlled.

130062/0660

- Vt -

TableelX

Cultivated / applied connection weeding combination method

Example l corn /

Setaria faberi

Corn/
Ipomoea

S.A. S.A.

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

S.A. S.A.

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

Corn / S.A.

Xanthium S.A. pensylvanxcum

P.P.I.

P.P.I.

WAT ^GR 15 ^{/ GR} 85

S.F.

6 4.48 / <1.12 (4.0)

6.5> 7.84 / 8.4 (NS)

6 4.76 / 1.96 (2.5)

6.5> 6.72 / 4.48 (1.5)

3> 4.48 /> 4.48 (-)

6> 4.48 /> 4.48 (-)

3 4.76 /> 4.48 (-)

6 4.76 /> 4.48 (-)

3> 4.48 /> 4.48 (-)

6> 4.48 /> 4.48 (-)

3 4.76 /> 4.48 (-)

6 4.76 /> 4.48 (-)

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

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130062/0660

- -ST -

Table X

Cultivated / Anwen-Verbin- Weeddungsdung ^ Kobmination process

Example l Cotton /
purple
Sedge

Cotton/

Sida

spinosa

Cotton/
Purslane

Cotton/
Digitaria
(smooth or
haired)

Cotton/
Bedstraw

S.A. S.A.

P.P.I.

S.A. S.A.

P.P.I. S.A.

S.A.

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

WAT

^GR 15 ^{/ GR} 85

3.64 / 1.68 3.36 / 2.24

3.36 / 4.2

3.64 / 3.08 3.36 / 4.76

3.36 / 4.76 3.36 / 1.96

S.F.

(2.17) (1.5)

(NS)

(1.18) (NS)

(NS) (1.7)

1.4 / <1.12 (> 1.25)

0.84 / 1.12 (NS) 0.84 / <1.12 (-)

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

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

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130062/0660

up to 12 WAT. The data in Table XI represent the average of 3 passes in sandi £ eni clay, which is 1.3% contained organics, 79.2% sand and 10% clay; the Herbicide was applied to the surface.

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130062/0860

ö O β »κ>

Cf) O

rienye
(kg / ha) Tabel XI % Panicum
texanum Heimung Acanthosperic space
H. 12th Richardia
SC. 12th 2.24
3.36
>
4.48 WAT WAT 40
60
100 WAT 95 peanuts 4 8 4 8 4 8 VJAT 50 67 '
68 63
85 83 12th 78
85
95 · 0 90
0
0 95 link 4 8 12th 40
55
78 Example 1 5 0
10 0
17 7 0
0
0

cn cn

cn CO

The data in Table XI show that the compound of Example 1 Texas panicum in peanuts selectively controlled for up to 8 weeks, and even at 12 WAT at 4.4 8 kg / ha showed a high degree of control; selective control of Acanthospermum h. was at 3.36 kg / ha for 8 weeks Achieved, and complete control was obtained for 12 WAT with 4.48 kg / ha maintained; selective control of Richardia se. was using less than 2.24 kg / ha for 8 WAT reached, and with 4.4 8 kg / ha one got 9 5% control with 12 WAT.

In further greenhouse tests, compounds according to the invention showed selective control of a large number of annual and perennial weeds in various crops. For example, the compound of Example 1 selectively controlled purple sedge in both corn and soybeans, and the corresponding crop / weed GR.p / GRgr ratios (expressed in kg / ha) were 0.67 / 0.25 (SF = 2, 7) in corn and 1.12 / 0.25 (SF = 4, .5) in soybeans. The compound of Example 11 showed selective control of yellow sedge and couch grass in corn and soybeans. The culture / sedge _{GR 15 ZGRg 5} ratios were> 2.24 / 0.95 (SF = 2.4) in maize; 2.24 / 0.5 (SF = 4.5) in soybeans and the corresponding GR ₅ / GR _ß5 ratios for corn and soybeans in couch grass were> 2.24 / 0.5 (SF => 4.5). In one

- / 57

The test against yellow sedge in cotton was the GR _C / GR _OC

15 ob

Ratio (average of 2 passes) 1.96 / 0.95 (SF = 2.1). The compound of Example 13 showed equally selective control of yellow sedge in cotton and of couch grass in wheat, the respective ^GR ₁₅ / ^GK ₈₅ ratios were 0.7 / 0.47 (SF = 1.7) in cotton and 0.58 / 0.47 (SF = 1.2) in wheat.

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

Cotton, So_j.abo.hnen and maize ^ * .. ,, ■, * sedge xn / determined for each of the compounds tested; the respective GR ₁₅ - and GR ^ quantities fo _r, these compounds are shown in Table XII; the selectivity factors are in brackets after each crop.

Table XII

^GR 85 ^GR 15

(kp7ha) (kft / ha)

Connected yellow

dung sedge cotton soybean corn

Example l 0.24 1.96 (8.2) 0.87 (3.6) 0.69 (2.9)

Example 13 0.21 2.52 (12.0) 1.96 (9.3) 2.52 (12.0)

Example lU 0.38 2.8 (7.4) 2.24 (5.9) 1.68 (4.4)

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

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130062/0660.

The compounds of Examples 1 and 13 to 15 were also tested against couch grass in wheat, soybeans and corn; every of the compounds were found to be non-selective in wheat. The selectivity data for the above compounds versus Mercury in soybeans and corn are summarized in Table XIII.

1 Tabel GP
° ^K 85 XIII ^GR 15 11.6) Corn 13th (kg / ha) (kg / ha) 4.7) 0.69 (9.9) IU Couch grass Soy off 3.2) 1.68 (4.7) 15th 0.07 0.8lC 2.6) 2.52 (5.6) 0.36 1.68 ( 2.24 (3.0) 0.45 1.46 ( link 0.75 1.96 ( Ex. Ex. Ex. Ex.

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

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130062 / 068Ö

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bb

Q)

• f

• Η ^ • · Η (U

ro

• ρ a

Il

CM O
. . J H T H • f — f CM -
-in
O f \ * J- O
H '
-CD
⁰ f \

γ ~ ο γ »- ο

O · "■ O» ν

OH OH

CM O CM

rH · »Η

VD O CM

OO O O CM G 0 Λ •H
Λ Care] OO
CM ■ H O O Sorghum O "XX3
r \ CM
H Λ _P. CM
H
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CM

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r- ΓΟ

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-H · Η

- / 60

130062/066

-GA-

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

A particular benefit of a herbicide is its ability to act in a wide variety of soil types. Table XV summarizes data showing the herbicidal effectiveness of the compound of Example 1 on couch grass in soybeans in a variety of soil types containing various levels of organics and clay. Herbicide treatments were by working into the soil, the seeds were planted 0.95 cm deep and received O ₃ SH cm irrigation from above. The observations were made about 3 weeks after treatment * The selectivity factors are given in brackets. .

Table XV shows that the compound of Example 1 versus Soil types with different proportions of organic matter seems to be quite insensitive, she showed selective control of Quecki? in soybeans in soils that have a share of organic matter from 1.0% to 60%, and a clay content of at least 1.8% and about 37%. The data for soy

- / 62

Table XV

Connect Organic Soil type Fabrics volume (kg / ha) Soybeans "" 85 ' (5, 1) manure % % 1.12 (> 8 , 0) Ray Schlufflehir. 1.0 9.6 > 2.24 (- ) Example 1 Sarpy
silty clay 2.3 30.35 - (20 , 0) Wabash
silty clay U, 3 33.0 2.24 Couch grass (9, 8th) Drummer
silty clay 6.0 37.0 1.96 0.22 (> 3 , 9) Florida sand 6.8 1.8 > 2.24 0.28 Florida peat peat 60 0.28 0.11 0.2 0.58

Wabash silty clay beans were indeterminate in this test. Even the silty tone for sarpy and drummer as well Florida peat soil specified selectivity values are minimum values as the maximum test rate was 2.24 kg / ha, and that Herbicide for soybeans was harmless at the same amount above 2.24 kg / ha.

Laboratory tests have been carried out to determine the resistance of the herbicides of the invention to soil leaching and to determine the resulting herbicidal effectiveness. In these tests, the compounds of the examples 1 and 4 to 6 dissolved in acetone and then in various concentrations on a weighed amount of Ray silt loam and drummer sprayed silty clay that contained in pots whose drain holes in the bottom of the pot were covered with filter paper. The pots with the treated soil were made leached out by placing them on a turntable rotating under two nozzles of a water tank; these goods adjusted so that they gave off 2.5 cm of water per hour, simulating rain. The leaching rates were through Change of time set on the turntable. The water placed on the bottom of the pot was passed through Pass filter paper and the drainage holes. The pots were then left for 3 days at room temperature. The treated earth was then removed from the pots, crumbled and used as a surface layer on other pots with the same base.

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ben in which Echinochloa seeds had already been sown. The pots were then placed on greenhouse tables, watered from below, and left to grow for 2 to 3 weeks. The visual evaluation of the percentage growth inhibition was compared with untreated control pots, as was the Fresh weights of Echinochloa; the data for the controls were obtained from 6 runs, those for the 3-run test compounds; the data are summarized in Table XVI. The fresh weight of the weeds was not measured for the tests in Drummer silty clay loam. .

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Table XVI

Echinochloa crus-galli

Connect lot 0 rain manure (kg / ha) 0 (cm) O
Control ₀ 0
1.27- 5'J 08 Ct » 10.16 O

# eisp. l 2.24

0.56

0.14

isp. 4 2 _T 24

% Inhibition

Fresh weight (g)

- —— τ drummer

Ray 'silt loam drummer Schluffton Ra y silt loam silton

O 100 1.27 100 5.08 95 10.16 35 0 100 1.27 100 5.08 70 10.16 33 0 95 1.27 96 5.08 58 10.16 20th 0 100 1.27 100 5.08 100 10.16 95

100 100 100 100

100 100 100 100

100 97 95 20

100 100 100 100

Avg.

0.20 2.65

1.21 2.73

0.20 0.17 1 74 3.26

0
0
0
0.22

4.37 3.88 4.14 3.98

Table XVI

Echinochloa crus-galli

% Inhibition fresh weight (g)

Connected amount of rain. . · Drummer

^ dung (kg / ha) (cm) Ray Schluffle hm Drummer Schluffto n Ray_ Schlufflehm Schluffton

0.56 0 100 100 0

1.27 100 100 0

5.08 94 100 0.24

- * 10.16 52 100 1.97

g 0.14 0 99 81 0.05

U 1.27 95 99 0.22

_Μ · 5.08 63 94 1.53

** 10.16 14 54 3.15 ι

S Beisn 5 ² · ²⁴ ° ¹⁰ ° ¹⁰ ° ° E

g ^Beis P · ^5: _{χ 27,100. 100} ο - Ί

5.08 92 100 0.31

10.16 71 100 1.18

0.56 0 99 100 0.02 τ ~

1.27 "100 100 0

5.08 89 100 0.44

10.16 17 96 ■ 3.41

0.14 0 98 70 0

1.27 90 96. 0.41 _ω

, 5.08 38 85 2.77 ^

^ '10.61 12 47 3J62 ^ a

OT. O

Table XVI

Echinochloa crus-galli

Connection set
manure (kg / ha) rain
(cm) sisp. 6 °> ²⁴ 0
1.27
5.08
10.16 0 _? 56 0
1.27
5 ^ 08
10.16 0.14 0
1.27
5.08
10.16

% Inhibition fresh weight (g)

Drummer

Ray Schluffl eh with the drummer Schlufft on Ray Schluffleh with the Schluffton

100 0 -

100 0

100 0.03

100 0.64

<a 0.56 0 99 50 0.04

© 1.27 99 100 0.02

© 5 ^ 08 90 93 0.41

* 10.16 72 84 1.17> · \

12 0.66 ^

Qi ' 1.27 90 26 0.43 * ♦ "

«:. 5.08 58 20 1.72 '

^Ä - ■ ■ "29 12 2.92

cn ro co

Table XVI shows that the compounds of the invention are fairly good under various precipitation conditions were resistant to leaching in the soil. In particular, each of the compounds of the present invention controlled at the 2.24 kg / ha application rate Echinochloa below the equivalent of 10.16 cm precipitation in Ray silt loam and Drummer Schlufftonlehm, excluding the compounds of Example 1 and 5 in Ray Schluff, where control is under one Equivalent of 5.08 cm of precipitation was maintained. Even with the low application rate of 0.14 kg / ha controlled the compounds of Examples 1, 4 and 5 Echinochloa in Drummer silty clay loam under one equivalent of 5.08 cm of precipitation.

Toxicological studies of the compound of Example 1 indicated that the compound was fairly harmless. It is slightly toxic (OLD ₅₀ 2300 mg / kgj MLD ₅₀ > 5010 mg / kg), it causes slight eye irritation, but no skin irritation. Special handling measures beyond the normal precautionary measures are not considered necessary.

From the preceding detailed description it can be seen that the compounds according to the invention are unexpected and exhibited extraordinarily superior herbicidal properties, both absolutely and in comparison to the structurally most closely related known compounds. The compounds according to the invention were found to be in particular

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130062/0660

as excellently selective herbicides, especially when controlling hard-to-kill perennials and annuals Grasses in soybeans and corn, but also in peanuts, cotton and other crops. The compounds according to the invention especially showed excellent control of perennial weeds such as couch grass and sedge, as well resistant annual grasses such as Panicum texanum, Rottboellia, Panicum miliaceum, Brachiaria plantaginaria, Sorghum halepense seedlings, Sorghum bicolor and / or Oryza sativa, while also controlling and / or controlling less resistant annual grasses and perennial weeds pushed back.

- / 69

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 produced by mixing the active ingredient with an adjuvant, including diluents, extenders, carriers and conditioning agents, so that preparations in the form of finely divided solid particles, granules, pellets, solutions, dispersions or emulsions are produced. Thus, the active ingredient can be used with an adjuvant such as a finely divided solid, a liquid of organic origin, water, a wetting agent, a dispersing agent, an 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 surfactants in sufficient quantities to make a suitable preparation to make it easily dispersible in water or oil. The recording a surface active agent in the preparations promotes their effectiveness significantly. Under the term "Surfactant" includes wetting agents, dispersants, Suspending and emulsifying agents. Anionic, cationic and nonionic agents can

can be used equally.

- / 70

130062/0660

Preferred wetting agents are alkylbenzenes and alkylnaphthalene sulfonates, sulfated fatty acid alcohols, amines or acid amides, long-chain acid esters of sodium isothionate, Sodium sulfosuccinate esters, sulfated or sulfonated fatty acid esters, petroleum ulfonates, sulfonated vegetable oils, ditertiary acetylenic glycols, polyoxyethylene derivatives of alkylphenols (especially isooctylphenol and nonylphenol) and polyoxyethylene derivatives of the higher fatty acid monoesters of hexitol anhydrides (e.g. sorbitan). Preferred dispersants are methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalene sulfonates, Sodium naphthalene sulfonate and polymethylene bisnaphthalene sulfonate.

Wettable powders are water-dispersible preparations that contain one or more active ingredients, an inert extender solid and one or more wetting and dispersing agents contain. The inert extend solids are common of mineral origin, e.g. natural clays, .diatomaceous earth and synthetic minerals of silica and the like. Such extenders include kaolinites, attapulgite clay and synthetic magnesium silicate. The wettable powders of the invention usually contain about 0.5 to 60 parts (preferably 5 to 20 parts) active ingredient, about 0.25 to 2 5 parts (preferably 1 to 15 parts) wetting agent, about 0.25 to 25 parts (preferably 1.0 to

- / 71

15 parts) dispersing agent and 5 to about 95 parts (preferably 5 to 50 parts) inert extender solids, where all proportions are based on the weight of the total preparation are related. 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 that 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 adding an aqueous mixture of one in water. soluble active ingredient and an emulsifying agent is stirred until it is uniform, and then it is homogenized so that you get a receives stable emulsion of very finely divided particles. The resulting concentrated aqueous suspension is characterized by their extremely small particle size, so that after thinning and spraying the coating is very uniform is. Suitable concentrations of these preparations contain about 0.1 to 60% by weight, preferably 5 to 50% by weight Active ingredient, the upper limit being determined by the solubility limit of the active ingredient in the solvent.

Another type of aqueous suspension encapsulates a water-immiscible herbicide so that an in

- / 72

Microcapsule phase dispersed in an aqueous phase is formed. In one embodiment, very small capsules are formed, by making an aqueous phase containing a lif-ninsulfonate emulsifier contains, a water-immiscible chemical and polymethylene polyphenyl isocyanate that brings together water-immiscible phase is dispersed in the aqueous phase and then a polyfunctional amine is added. The isocyanate and amine compounds react and form a solid urea shell around particles that are immiscible with water Chemical so that microcapsules of the same are formed. In general, the concentration of the encapsulated material will be in the range at about 480 to 700 p./Liter, preferably 480 to 600 g / liter of the entire preparation.

Concentrates are usually solutions of active ingredient in water-immiscible or only partially water-miscible solvents with a surfing agent. Suitable solvents for the active ingredient according to the invention include dimethylformide, Dirr.ethyl sulfoxide, N-methylpyrrolidone, hydrocarbons and water-immiscible ethers, esters or ketones. However, other strong liquid concentrates can also be dissolved by dissolving them of the active ingredient in a solvent and then diluted, e.g. with kerosene, to spray concentration will.

The concentrate preparations generally contain about 0.1 to 95 parts (preferably 5 to 60 parts) of active ingredient,

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130065/0660

about 0.25 to 50 parts (preferably 1 to 2 5 parts) surfactant and, if necessary, from about M 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 that contain an active ingredient that adheres to a matrix made of inert, finely divided, particulate extender is liable or distributed in the same. To support the leaching of the active ingredient from the particles, in the Preparation a surface active agent, as they are listed above, be present. Natural clays, pyrophyllites, Ulits and vermiculites are examples of useful types of particulate mineral extenders. Preferred extenders are porous, absorptive, preformed particles, such as preformed and sieved particulate matter Attapulgite or, by heat, expanded, 'particle-shaped Vermiculite, as well as finely divided clays such as kaolin clays, hydrogenated attapulgite or bentonite clays. These extenders are used to produce 'the herbicidal granules rr.it the active ingredient sprayed or mixed.

The granule preparations according to the invention can be 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 Contains 5 parts by weight of surfactant per 100 parts by weight of clay particles.

130062/0660

The preparations according to the invention can also contain other additives, for example fertilizers, other herbicides or Pesticides, protective substances and the like. Used as adjuvants or in combination with one of the adjuvants listed above be used. Chemicals that are useful for combination with active ingredients according to the invention are i.a. Triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic acid or phenol derivatives, thiol carbamates, Triazoles, benzoic acids, nitriles, biphenyl ethers and the like, such as:

Heterocyclic nitrogen / sulfur derivatives

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

3-Isopropyl-1H-2,1,3-benzothiadiazin-4- (3H) -one-2,2-dioxide

3-amino-1,2, M-triazole

6,7-dihydrodipyrido (1,2-a: 2 ', 1'-C) -PyTaZIdUnIUmSaIz

5-bromo-3-isopropy1-6-methyJuraeil 1,1'-Dimethy1-4,4'-bipyridinium

Ureas

N ¹ - (4-chlorophenoxy) -phenyl-N, N-dimethylurea N, N-dimethyl-N '- (3-chloro-4-methylphenyl) -urea 3- (3,4-dichlorophenyl) -l, l- dimethylurea 1,3-dimethy1-3- (2-benzothiazoly1) -urea 3- (p-chlorophenyl) -1, 1-dimethylurea 1-butyl-3- (3,4-dichlorophenyl) -1-methylurea

- / 75

Carbamates / thiol carbamates "

2-chloroallyl diethyldithiocarbamate S-iU-ChlorobenzyD-NjN-diethylthiolcarbamate Isopropyl N- (3-chlorophenyl) carbamate S-2, S-dichloroallyl-NjN-diisopropylthiol carbamate Ethy1-N, N-dipropylthiol carbamate S-propyl dipropyl thiol carbamate

Acetamide / Acetanilide / Aniline / Amide

2-chloro-N, N-diallylacetamide N, N-dimethy1-2,2-diphenylacetamide

N- (2,4-Dimethyl-5- [[(trifluoromiethyD-sulfonyl] -amino] phenyl) -acetamide

N-isopropyl-2-chloroacetanilide 2 ', 6'-Diethyl-N-methoxymethyl-2-chloroacetanilide

2'-methyl-6'-ethyl-N- (2-niethoxyprop-2-yl) -2-chloroacetanilide

a, a, a-Trifluoro-2,6-dinitro-N, N-dipropyl-p-toluidine N- (1,1-Dimethylpropynyl) -3,5-dichlorobenzamide

Acids / esters / alcohols

2,2-dichloropropionic acid 2-methyl-U-chlorophenoxyacetic acid 2,1-dichlorophenoxyacetic acid methyl 2- [H- (2, U-dichlorophenoxy) phenoxy] propionate 3-amino-2, .5-dichlorobenzoic acid 2-methoxy 3,6-dichlorobenzoic acid

- / 76

-η-

2, 3,6-trichlorophenylacetic acid, N-1-naphthylphthalamic acid

Sodium 5- (jü-chloro-H-itrifluoromethyl) -phenoxy3-2-nitrobenzoate

4,6-dinitro-o-sec-butylphenol

N- (phosphonomethyl) glycine and sane C ^ _-6 Monoalkylamin- and alkali metal salts, and combinations thereof

Ether

2,4-dichlorophenyl-4-nitrophenyl ether

2-chloro-a, α, α-trifluoro-p-tolyl-3-ethoxy-H-nitrodiphenyl ether

Various

2,6-dichlorobenzonitrile Hononatri ums riuren.ethanarsonat Dinatriuinniethanar Sonat

Fertilizers that can be used in combination with the active ingredients are, for example, ammonium nitrate, urea, potash and superphosphate: Other useful additives include substances in which plant organisms take root and grow, e.g. compost, Dung, humus, sand and the like.

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

specified.

-777

13008270660

-W-

I. EmJgeable concentrates

Weight%

A. Compound of Example No. 1 50.0

Calcium dodecylbenzenesulfonate / polyoxyethylene ether mixture

(e.g. Atlox 3437F) 4.85

Calcium dodecylbenzenesulfonate (FIoMo 60H)
Cg aromatic solvent

0 , 15 45 , 00 100 , 00 85 , 0

B. Compound of Example No. 4
Calcium dodecyl sulfonate / alkylaryl polyether alcohol mixture 4.0 Cg aromatic hydrocarbon solvent

C. Compound of Example No. 6
Calcium dodecylbenzenesulfonate / polyoxyethylene ether mixture

(e.g. Atlox 3437F) xylene

II. Liquid concentrates

A. Compound of Example No. 4 10.0

Xylene 90.0

100.0

11 -L ⁰ . 100 , 0 5 , 0 1 , 0 94 100 , 0

- / 78

130062/0660.

Weight%

B. Compound of Example No. 5 85.0 Dimethylsulfoxide " IS ₈ O

100.0

C. Compound of Example No. 6 50.0 N-Methylpyrrolidone 50.0

100.0

D. Compound of Example No. 7 5.0 Ethoxylated Castor Oil 20.0 Rhodamine B 0.5 Dimethylformamide 7H, 5

100.0

III. Emulsions

Weight %

A. Compound of Example No. 12 40.0 Polyoxyethylene / polyoxypropylene block

Copolymer with butanol (e.g. Tergitol XH) 4.0

Water 56.0

100.0

B. Compound of Example No. 13 5.0 polyoxyethylene / polyoxypropylene

Block copolymer with butanol 3.5

Water 91.5

100.0

IV. Wettable powders

A. Compound of Example No. 1 25.0

Sodium lignosulfonate 3.0

Sodium N-methyl-N-oleyl taurate 1.0

Amorphous silica (synthetic) 71.0

100.0 - / 79

130062/0660

If weight%

B. Compound of Example No. 12 80.00 Sodium Dioctylsulfosuccinate 1.25 Calcium Lignosulfonate 2.75 Amorphous Silica (synthetic) 16.00

100.00

C. Compound of Example No. 13 Sodium Lignosulfonate Sodium N-methyl-N-oleyl taurate kaolinite clay

V. Dusts

A. Compound of Example No. 7 2.0

Attapulgite 98.0

100.0

B. Compound of Example No. 8 Montmorillonite

C. Compound of Example No. 9 30.0 Bentonite 70.0

100.0

D. Compound of Example No. 10 Diatomaceous Earth.

- / 80

130062/0660

VI. Granules

Weight%

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

100.0

B. Compound of Example No. 6 30.0 Diatomaceous Earth (20/40) 70 _? 0

100.0

C. Compound of Example No. 12 0.5 Bentonite (20/40) 99.5

100.0

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

100.0

VII. Microcapsules

Α. 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. Compound 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 lignosulphate

(Treax LTM) 2.0

Water 18.0

100.0

- / 81

130062/0660

When used according to the invention, effective amounts of Acetanilides according to the invention to those containing the plants Soil applied or appropriately absorbed in aqueous media. The application of the preparations as Liquids and solid particles on the earth can be done with conventional methods, e.g. with motorized atomizers, Tank and hand sprayers or spray atomizers. The preparations can also be used in small doses because of their effectiveness dispersed by airplanes as dust or spray. Herbicidal preparations are used in aquatic plants usually by adding the preparations to the aqueous medium in the area in which the aquatic plants are controlled it is asked for.

t applying an effective amount of the compositions of the invention at the site of the undesired weeds is essential and critical for the inventive application. The exact amount of active ingredient to be used depends on various factors, such as the type of plant and its stage of development, the type and condition of the soil, the amount of rain and the specific acetanilide used. In the case of selective pre-emergence application to plants or soil, an application rate of 0.02 to 11.2 kg / ha, preferably from about 0.04 to 5.60 kg / ha, or 1.12 to 5.6 kg / ha is usually required Acetanilide used. In some cases, larger

»Or smaller quantities are required. The skilled person can • - / 82

k ■

130062/0660

On the basis of the description, including the examples, it is easy to determine the optimum amount for each case.

The term "soil" is used in the broadest sense of the word used and includes all common types of soil as described under "soils" in Webster's New International Dictionary, Second Edition, Unabridged (1961). So the name refers to every substance or every one Medium in which plants can take root and grow, and includes not only soil, but also compost, manure, dung, Humus, sand and the like that can sustain plant growth.

End of description

13Ö0R2 / 0860

Claims (1)

Claims characterized in that R CL _{5 is} alkyl or alkoxyalkyl or alkenyl or alkynyl with up to 5 carbon atoms, and R _{1 is} hydrogen, methyl or ethyl; with the proviso that when R 1 is hydrogen, R is isopropyl, and when R is ethyl, R is ethyl, n-propyl or isopropyl represents. 2. Compounds according to claim 1, characterized in that RC "_ _{u is} alkyl. 3. Compounds according to claim 2, characterized that R. is methyl. 130062 / ΟδδΟ - ^{/ 2} • (089) 911272 telegrams: Bank accounts: Hypo-Buik Manchen 4410122850 9 * 1273 BEROSTAPFPATENT Manchen (BLZ 70020011) Swift Code: HYPO DE MM 9 « 1274 TELEX: Biycc Vereinfbuik Manchen 453 100 (BLZ 70020270) '' W331O 0524560 BERG d Pwticheck Munich 65343-808 (BLZ 70010080) - O mm 4. A compound according to claim 3, characterized in that it is N ~ (ethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 5. Compound according to claim 3, characterized in that that they are N- (n-propoxymethyl) -2'- trifluorraethy1-6'-methyl-2-chloroacetanilide. 6. Preparation according to claim 3, characterized marked chnet that they are N- (isopropoxymethyl) -2'-trifluoromethyl-6 '-niethyl-2-chloroacetanilide is. 7. A compound according to claim 3, characterized in that it contains N- (isobutoxymethyl) -2'-tri- is fluoromethyl-6'-methyl-2-chloroacetanilide. 8. A compound according to claim 2, characterized in that R _{1 is} ethyl. 9. A compound according to claim 8, characterized in that it is N- (ethoxymethyl) -2'-trifluoromethyl-6 '-ethyl-2-chloroacetanilide is. 10. A compound according to claim 8, characterized in that it is N- (n-propoxymethyl) -2 · -trifluoromethyl-6'-ethyl-2-chloroacetanilide is. 130062/0660 11. A compound according to claim 8, characterized that they are N- (isopropoxymethyl) -2'-tri- is fluoromethyl-6'-ethyl-2-chloroacetanilide. 12. Compounds according to claim 2, characterized in that that R. means hydrogen. 13. A compound according to claim 12, characterized in that it is N- (isopropoxymethyl) -2 ^l -trifluoromethyl-2-chloroacetanilide. 14. A compound according to claim 1, characterized in that R is a C ", alkenyl radical. 15. A compound according to claim 14, characterized in that it is N- (allyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 16. A compound according to claim 1, characterized that R is a C-r alkynyl radical. 17. A compound according to claim 16, characterized in that it is N- (propargyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. - / 4 130062/0660 -I ₄ - 18. A compound according to claim 1, characterized in that R is an alkoxyalkyl radical with up to to 5 carbon atoms means. 19. A compound according to claim 18, characterized in that that they are N- (2-methoxyethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 20. Herbicide preparation, characterized in that that they are an adjuvant and a herbicidally effective amount of a compound of the formula CHOIR contains, wherein R is CLg-alkyl or alkoxyalkyl or Alkenyl or alkynyl with up to 5 carbon atoms, and R ^ are hydrogen, methyl or ethyl; with the Provided that, when R. is hydrogen, R is isopropyl, and, when R. is ethyl, R is ethyl, n-propyl or isopropyl represents. - / 5 130062/0660 21. Preparations according to claim 20, characterized in that in the compound RC _{2 is} _j, -alkyl. 22. A compound according to claim 21, characterized in that in the compound R _{1 is} methyl. 23. Preparation according to claim 22, characterized in that the compound N- (ethoxyrnethyl) -2 '-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 24. Preparation according to claim 22, characterized that the compound N- (n-propoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 25. Preparation according to claim 22, characterized in that the compound N- (isopropoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 26. Preparation according to claim 22, characterized in that the compound N- (isobutoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloro- is acetanilide. ._ 130062/0680 27. Preparation according to claim 21, characterized in that R _{1 is} ethyl. 28. Preparation according to claim 27, characterized in that the compound N- (ethoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide is. 29. Preparation according to claim 27, characterized in that the compound is N- (n-propoxymethyl-2 ¹ -trifluoromethyl-6'-ethyl-2-chloroacetanilide. 30. A compound according to claim 27, characterized in that the compound N- (isopropoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide is. 31. Preparation according to claim 21, characterized in that R ^ is hydrogen. 32. Preparation according to claim 31, characterized in that the compound N- (isopropoxymethyl) -2'-trifluoromethyl-2-chloroacetanilide is. - / 7 130062/0660 33. Preparation according to claim 20, characterized in that in the compound R means an alkenyl radical of up to 5 carbon atoms. 3 * 4. Preparation according to claim 33, characterized in that that the compound N- (allyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 35. Preparation according to claim 20, characterized in that that in the compound R is an alkynyl radical having up to 5 carbon atoms. 36. Preparation according to claim 35, characterized that the compound N- (propargyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 37. Preparations according to claim 20, characterized that in the compound R denotes an alkoxyalkyl radical having up to 5 carbon atoms. -/8th 130062/0660 38. Preparation according to claim 37, characterized in that the compound N- (methoxyethoxymethyl) -2'-trifluoroniethyl-6'-methyl-2-chloroacetanilide is. 39. A method for controlling unwanted plants in crops of useful plants, characterized that on the site thereof a herbicidally effective amount of a compound of the formula is applied, in the RC ₁ (.-alkyl or alkoxyalkyl or alkenyl or alkynyl with up to 5 carbon atoms, and R _{1 is} hydrogen, methyl or ethyl; with the proviso that, when R 1 is hydrogen, R is isopropyl, and when R _{1 is} ethyl, R is ethyl, n-propyl or isopropyl. HO. Process according to Claim 39, characterized in that in the compound R is C ₂ _ _u -alkyl. 130062/0660 - / 9 41. The method according to claim 40, characterized in that in the compound R _{1 is} methyl. 42. The method according to claim 41, characterized in that the compound N- (ethoxymethyl) - Is 2'-trifluoromethyl-6'-methyl-2-chloroacetanilide. 43. The method according to claim 41, characterized that the compound N- (n-propoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 44. The method according to claim 41, characterized in that the compound N- (isopropoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide
is. 45. The method according to claim 41, characterized that the compound N- (isobutoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 46. The method according to claim 40, characterized in that R _{1 is} ethyl. 47. The method according to claim 46, characterized that the compound N- (ethoxymethyl) -2'- - / 10 130062/0880 is trifluoromethyl-6'-ethyl-2-chloroacetanilide. 48. The method according to claim 46, characterized in that the compound N- (n-propoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide is. 49. The method according to claim 46, characterized in that the compound N- (isopropoxymethyl) -2'-trifluoromethyl-6'-ethyl-2-chloroacetanilide is. 50. The method according to claim 40, characterized in that R _{1 is} hydrogen. 51. The method according to claim 50, characterized in that the compound N- (isopropoxymethyl) -2'-trifluoromethyl-2-chloroacetanilide is. 52. The method according to claim 39, characterized that in the compound R denotes an alkenyl radical having up to 5 carbon atoms. 53. The method according to claim 52, characterized in that the compound N- (allyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. - / 11 130062/0660 54. The method according to claim 39, characterized that in the compound R is an alkynyl radical having up to 5 carbon atoms. 55. The method according to claim 54, characterized that the compound N- (propargyloxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. 56. The method according to claim 39, characterized in that in the compound R is an alkoxyalkyl radical means with up to 5 carbon atoms. 57. The method according to claim 56, characterized in that the compound N- (methoxyethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide
is. 58. The method according to claim 39, characterized in that the crop plants maize, sorghum, Soybeans, cotton, peanuts, French beans, wheat and canola are available. 59. The method according to claim 58, characterized in that the compound N- (ethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is. - / 12 130062/0660 60. methods of controlling undesirable plants in maize crops, characterized in that on the site thereof a herbicidally effective amount of N- (ethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is applied. 61. methods of controlling undesirable plants in soybean crops, characterized in that a herbicidally effective on the site of the same Amount of N- (ethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is applied. 62. A method for controlling unwanted plants in cotton crops, characterized in that that on the site of the same a herbicidally effective amount of N- (ethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is applied. 3. Methods for controlling undesirable plants in rapeseed crops, characterized in that on the site thereof a herbicidally effective amount of N- (ethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is applied. 61. Methods of controlling undesirable plants in French bean crops, characterized by - / 13 130062/0660 net that on the site of the same a herbicide effective amount of N- (ethoxymethyl) -2'-trifluoromethyl-6'-methyl-2-chloroacetanilide is applied. - / 14 130062/0660