DD157298A5 - PREPARATION HERBICIDE - Google Patents

Abstract

The invention relates to a group of N-hydrocarbyloxy-methyl-2-haloacetanilide compounds, herbicidal preparations which contain these compounds as active ingredient, and to processes for using these herbicides in various crops, in particular soybeans, cotton, peanuts, rapeseed and bush beans. The herbicides according to the invention are particularly effective against hardy perennial herbaceous weeds such as Wheatweed and Cyperus esculentus, as well as perennial weeds such as e.g. Sida spinosa, Sesbania exaltata, Sorghum halepense seedlings, Sorghum bicolor, etc.

Description

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

'Characteristic ei istics <3.θϊ bekannteη t_echm ^ g ^ ^ he Lgsungen Among publications ^ to this invention relate _s are numerous descriptions found of 2-Halogenacetanilidenj. which may be unsubstituted or substituted with a plurality of substituents on the anilide nitrogen atom or on the anilide ring, for example with alkyl, alkoxy, alkoxyalkyl, halogen or other radicals.

The compounds of the present invention characterized by an alkoxyiryl radical on the anilide nitrogen, an alkoxy radical in an ortho position, and a specific alkyl radical in the other ortho position are, as far as known, most likely to be those of U.S. Patents 3,442,945 and 3 5 47 ₅ 62O notably the compounds 2 ^f -tert-butyl-2-chloro-N-methoxymethyl-6 ^f -methoxyacetanilid and their Bromanalog (see FIG. Examples 18 and 34 in US Patent No. 3,547,620 * and Examples 18 "and 36 in U.S. Patent 3,442,945).

U.S. Patents Nos. 4,070,389 and 4,152,137 show a general formula which includes compounds of the type described in U.S. Patents 3,442,945 and 3,547,620.

O O O

The only example compound described having one alkyl radical in one ortho position and one alkoxy radical in the other ortho position, however, has an alkoxyethyl radical on the anilide nitrogen atom; Links of this kind are discussed in detail below.

Other less pertinent 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 H 152,137, characterized by an alkoxyalkyl radical having two or more carbon atoms between the anilide nitrogen atom and the oxygen atom of the alkoxy moiety. The closest specific disclosures in BE-PS 810,763 and German application 2 402 983 are compounds j which are an ethoxyethyl radical on the anilide nitrogen atom, a methoxy or ethoxy radical in an ortho position and a methyl or ethyl radical in the other ortho radical. Own position (see 810 763, compounds Nos. 7, 13 and 18); other less relevant homologs of these compounds are also described, e.g. Compounds Nos. 6, 9, 16 and 17 which have methypoxyethyl or methoxypropyl radicals substituted on the nitrogen atom, a methoxy or ethoxy radical in an ortho position and a methyl radical in the other ortho position.

U.S. Patent 3,442,945 contains some herbicide data ₅

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relating to those compounds mentioned above whose chemical configuration is most closely related to the compounds of the invention; some data are also given in the other patents for other analogous and homologous compounds which are less closely related in their chemical structure, e.g. In particular, these references describe herbicidal activity against a variety of weeds, but do not provide data for compounds which additionally and / or simultaneously kill the perennial weeds such as couch grass and yellow reed grass, which are difficult to kill , as well as a wide range of annual weeds including hardy annual broadleaf weeds such as thorny sida, hemp sesbania, datura, etc., and annual grasses such as sorghum halepense seedlings, sorghum bicolor, brachiaria, panicum species, red rice and raoulgras while also controlling other harmful annual or perennial weeds, such as knotweeds, Melde, Amaranthus, fox tails, Digitaria sanguinalis and Echinochloa crus-galli.

An extremely useful and desirable property of herbicides is the ability to control weeds over a longer period of time, the better during each growing season. With many known herbicides, sufficient weed control is only achieved for 2-3 weeks,

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in some very good cases, maybe up to 4 to 6 weeks before the chemical loses its phytotoxic potency. A disadvantage of most known herbicides is their relatively short life in the soil.

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

I

inactivate.

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

Yet another disadvantage of many known herbicides is the limitation to a particularly effective mode of use, i. Application to the surface before emergence or incorporation into the soil. The ability to deploy a herbicide by any means, by application to the surface or incorporation * into the soil, is highly desirable. Finally, there is a disadvantage of some herbicides

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in need of special care · for their handling due to their toxicity. A herbicide should therefore also be safe to handle.

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

The invention provides herbicides that control hard-to-kill perennial and annual weeds, such as couch grass, yellow reed grass, sorghum halepense seedlings, sida spinosa, hemp sesbania _s sorghum bicolor, brachiaria, '° an ic species, red rice and Raoulgras, as well as a broad spectrum of other harmful weeds, such as knotweed, Melde, Amaranthus datura, foxtails, Echinochloa and Digitaria. They also allow for increased repellency of resistant weeds such as Ambrosiaceae, Abutilon, Winds and Xanthium, while they are harmless to many crops such as soybeans, cotton, peanuts, rapeseed and / or bush beans.

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

The invention also relates to herbicides _s . against leaching or dilution in high humidity, eg in heavy rainfall, are resistant. '

Further, the invention relates to herbicides which are effective in a wide range of soils, from light to medium organic soils to heavy clay or loam.

Another advantage of the herbicides of the invention is

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a flexible application, e.g. by application to the surface before emergence or by incorporation into the soil. ·

Finally, the herbicides of the invention have the advantage that they are safe and do not require special handling precautions.

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

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

It has now been found that a selective group of 2-haloacetanilides formed by specific hydrocarbyloxymethyl radicals on the anilide nitrogen atom, specific alkoxy

1- ? 9Ö

Radicals in an ortho position and hydrogen or a methyl or ethyl radical in the other ortho position are of unexpectedly superior and superior herbicidal properties compared to known herbicides, including related and known homologous compounds.

An essential property of the herbicidal preparations according to the invention is their ability to control a broad spectrum of weeds. These include weeds, which can be controlled by conventional herbicides, and in addition a variety of weeds, individually or collectively so far the control of a single class of known herbicides -entgingen. At the same time they are harmless to crops of one or more crops, including in particular soybeans, cotton, peanuts, rape, kidney beans and others. While the known herbicides are useful for controlling a variety of weeds and, occasionally, certain resistant weeds, the unique herbicides of the present invention have been found to be capable of controlling or largely restraining a variety of resistant perennial and annual weeds, such as the perennial weeds and yellow cowslip, annual broadleaf weeds such as thorny sida, hemp sesbania, datura ·, knotweed plants, reporting, goosefoot plants, as well as annual grasses such as shattercane,

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Brachiaria, sorghum halepense seedlings, Panicum species, red JReis _s Raoul grass, and other noxious weeds such Herbstpanicum "foxtail, barnyardgrass and Digitaria. Improved weed population reduction has also been seen in resistant weeds such as Ambrosi'aceae, Äbutilon, Winde

and xanthiyme scored.

The compounds according to the invention are represented by "the formula

ClCH C CH ^ OR ^2/2

^OR 1

in which

R is ethyl, n -propyl, isopropyl, isobutyl, sec-butyl,

Cyclopropylmethyl, allyl or propargyl; R is methyl, ethyl, n-propyl or isopropyl, and R _? means hydrogen, methyl or ethyl, with the proviso

that if

R "represents hydrogen, R. represent ethyl and R represents allyl, if

R _{2 is} ethyl, R _{1 is} methyl and R is isopropyl if =

R is methyl, R is ethyl, isopropyl, isobutyl, sec-butyl

or cyclopropylmethyl, when R _{1 is} ethyl, R is sec-butyl, allyl or propargyl.

O O O / Ί /

&'Fca »I = J ^ ⁵ I' 1 ^ ¹ I *

represents when · ·. ,

R. n-P.ropyl means R ethyl and if

R. isopropyl, R represents ethyl or n-propyl.

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

Other compounds of the invention are:

2 ¹ ~ methoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide,

2'-methoxy-6'-niethyl-N- (l-sec-butoxymethyl) -2-chloracet-

anilide,

2 ^t -thoxy-6 ^f -methyl-N- (allyloxymethyl) -2-chloroacetanilide,

2 '-ethoxy-6 ^1-methyl-N- (propargyloxymethyl) -2-chloracetani-

2'-ethoxy-N- (allyloxy-ethyl) -2-chloroacetanilide,

2'-methoxy-6'-ethyl-N- (isopropoxymethyl) -2-chloroacetanilide, 2 ¹ -ethoxy-6'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetate

anilide,

2'-n-propoxy-6'-methyl-N-Cethoxym8thyl) -2-chloroacetanilide, 2'-isopropoxy-6 ^f-methyl-N- (ethoxymethyl) -2-chloroacetanilide

2'-isopropoxy-6 | methyl-N- (n-propoxymethyl) -2-chloracetani-

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

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

Another method described in more detail below provides for the transetherification of the appropriate N-methylene ether-2-haloacetanilide with the desired alcohol to the corresponding transesterified N-hydrocarbylmethyl-2-haloacetanilide.

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

Example 1 .

In this example, the preparation of a preferred embodiment, namely 2'-methoxy-6'-ir.ethyl-N-cisopropoxy

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2 2 8 414

methyl) -2-chloroacetanilide.

0.025 mol of 2 ^ ~ methoxy ~ 6 ^l-methyl-N- (methoxymethyl) -2-chloro> acetanilide in 100-150 ml isopropanol which contained about 0.02 mol of methanesulfonic acid, was maintained in a Soxhlet extractor under reflux, the Thimble contained 25 g of activated 3A molecular sieve to absorb the released methanol. The course of the reaction was monitored by gas-liquid chromatography. After completion of the reaction, the excess alcohol was removed in vacuo and the residue taken up in ether or chloroform. The solution was washed with 5% sodium carbonate solution, dried (Mg ₂ SO ₄ ) and evaporated. The product was purified by Kugelrohr distillation. Yield 55%; pale amber solid, mp HO-HI ° C

Elementaranalyseiberech.net for C ^ H ₂₀ ClNO ₃ C%):

C: '58, 84; H: 7.05; N: 4.90; Cl: 12,41

Found: C: 58.55; H: 7.08 ·; N: 4.89; Cl: 12.45 The product was identified as the entry-mentioned compound. '

Examples 2 to 9

There have been practically used the same procedure _s described in Example 1, reagent amounts and general conditions, however, the appropriate alcohol was used for the final product to re-etherification substituted to another, the

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J & TT

the above formula corresponding N-Hydrocarbyloxyinethyl-2-halogenacetanilj.de produce; these compounds are listed in Table I.

connection Table I Bp ° C (mm Hk) Ele ment analysis Found At game no. 2'-methoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide Empirical formula 170 (0.1) C H N Calculated 57.19 6.70 5.11 2 2'-Methoxy-i-6'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide C ₁₃ H ₁₈ ClNO ₃ C H N Cl 57.46 6.67 5 _S 16 59.90 7.36 4.62 11.97 3 2 ^K-ethoxy. 6 ^f -methyl- N - (allyloxymethyl) -. 2-chloroacetanilide C ₁₅ H ₂₂ ClNO ₃ no '(0,07) C H N Cl 60.10 7.40 4.67 11.83 60,30 6,80 4,64 11,69 4 2 ^! -Ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide C ₁₀ H ₂₀ ClNO ₃ 140 (0.1) C H N Cl 60,50 6,77 4,70 11,91 60.98 6.14 4.74 11.94 5 · 2 '' -Ethoxy-6-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide C ₁₅ H ₁₈ ClNO ₃ 135 (0.09)   C- H N Cl 60.91 6.13 • 4.74 11.99 60.98 7.59 4.42 11.22 cn 2'-methoxy-6'-methyl-N- (isobutoxymethyl) -2-chloroacetanilide C ₁₆ H ₂₄ ClNO ₃ 140 (0.1) C H N Cl 61.24 7.71 4.46 11.30 5,9,8 3 7,41 4,62 11,82 7 C ₁₅ H ₂₂ ClNO ₃ 60, -10 7,40 4,57 11,83

Table e I. - Continuation

example

analysis

connection

Empirical formula

^{2'-methoxy-6-r} -methy1 N- (cyclopropylmethoxy methyl) -2-chioracetanilid

2 ^f ~ methoxy ~ 6 ^f -ethyl-N- (isopropoxymethyl) -2-chloroacetanilide

C ₁₅ H ₂₂ ClNO ₃

Kp. ⁰ C .EIe- Calculated Found , 26 (mm Hg) . ' ment 60,50 60 77 145 C • 6.77 6 , 66 (0.1) H- 4.70 4 80 • N 11.91 11 , 81     egg 60.10 59 , 46 oil Q 7.40   7 , 61 H 4.6 7 4 , 71 • Ν 11.83 11 Cl

Be ispiel 10 '

Preparation of the tertiary N- (methoxymethyl) -anilide starting materials used to make the final products of Examples 1 to 3. , ·

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

0.025 mol of 2'-methoxy ~ 6 ^! -methyl-2-chloroacetanilide, 0.05 mol Brornmethylme thy ether and 2 g Benzyltrxethylammoniumbromid were dissolved in 70 ml of methylene chloride. 40 ml of 50% sodium hydroxide solution was then added portionwise with stirring and cooling, whereby the temperature between 20 and 25 ⁰ C was maintained. When the addition was complete, the mixture was stirred for a further 1.5 h. 100 ml of water were then added with cooling and the layers separated. The methylene chloride layer was washed twice with 30 ml of saturated sodium chloride solution, dried (MgSO ₄ ) and evaporated. The residue was crystallized or distilled in vacuo to give a yellow liquid, bp IUO ⁰ C at 1.2 mm Hg.

Elemental analysis; Calculated for C ₁₂ H ₁₆₃

C: 55.92; H: 6.26; N :. 5, MU • Found: C: 56.15; H: 6.33; N: 5.36

The product was identified as ^2f -methoxy-6'-methyl-N-methoxymethyl-2-chloroacetanilide.

Similarly, the N-methylene ether-substituted chloroacetanilide starting materials of Examples 2 to 9 were prepared by alkylation of the corresponding secondary anilide with brothine thyl ether, and the analogous chloromethyl and iodomethyl methyl ethers may also be used.

The secondary anilide starting material ₅ used in this example to prepare the tertiary N-methoxymethyl compound was prepared by chloroacetylation of the corresponding primary amine as follows:

0.03 mol of 2-methoxy-6-methylaniline in 30 ml of methylene chloride was stirred vigorously with O ₅ 05 mol of 10% sodium hydroxide solution while a solution of 0.033 mol of chloroacetyl chloride in 20 ml of methylene chloride was added; while the temperature was maintained by means of external cooling between 15 to 25 ⁰ C. The reaction mixture was stirred for a further 30 minutes after completion of the addition, the layers were separated and the methylene chloride layer was washed with water, dried and evaporated in vacuo. The product was crystallized from a suitable solvent to give white needles,

Mp. 130-131 ⁰ C, received.

Elemental Analysis: Calculated for, C ₁₀ H ₁₂ ClNO ₂ (%):

C: 56.21; H: 5.66; N: 6.56; Cl: 16.59 Found: C: 56.16; H: 5.66; N: 6.57; Cl: 16.55

The product was identified as ^2f -methoxy-6'-methyl-2-chloroacetanilide.

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

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

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

Example 11

4 ^»l 35 g 2"-n-propoxy-6'-methyl ~ 2 ~ chloroacetanilide, 3.4 g Chlorinethylethylether _s 1.5 g of benzyltriethylammonium chloride were mixed in 250 ml of methylene chloride and cooled; To the mixture was added 50 ml of 50% igeSNa0H at 15 ° C and stirred for 2 h when 100 ml of water were added, the layers were separated, washed with water, then dried over MgSO 4 and evaporated The product was purified by Kugelrohr distillation to give 4.8 g (89%). Yield) clear liquid, bp 130 ⁰ C at 0.07 mm Hg.

elemental analysis: Calculated for C.rH _?

C: 60.10; H: 7.40; Cl: 11.83 Found: C: 59.95; H: 7.39; Cl: 11,79

The product was identified as 2'-n-propoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide.

Example 12.

5.55 g of 2'-isopropoxy-6'-methyl-2-chloroacetanilide, 4.4 g of chloromethyl ethyl ether, 2.5 g of benzyltriethylammonium chloride in 2 50 ml of methylene chloride were mixed and cooled to 0 ⁰ C "To the mixture, 50 ml 50% NaOH was added all at once while keeping the temperature below 15 ° C. The mixture was stirred for 2 h, cooled, then 100 ml of water was added. The layers were separated, washed with water, ₁ .getrocknet over MgSO ^ and evaporated to give 4.7 g of

(69% yield) yielded product "in forin of a yellow

Eleinentar analysis: Calculated for C ^ H ^ CINO ₃ (%):

C: 60 _s 10; H: 7.40; N: 4.67; Cl: 11.83 Found: C: 60.10; H: 7.40; N: 4.64; Cl: 11,73

The product was identified as "2'-isopropoxy-6" ^{f "} -methyl-N- (ethoxymethyl) -2-chloroacetanilide.

Example 13

Practically the same procedure as described in Examples 11 and 12 was used, but chloromethyl propyl ether was used as the alkylating agent. 5.0 g (88% yield) of a yellow oil were obtained. ElementaranalyseiBerechnet for C ₁₆ H ₂₄ ClNO ₃ (I):

C: 61.24; H: 7.71; N: 4,46; Cl: 11.30 Found: C: 61.18; H: 7 _S 76; N: 4.43; Cl: 11.31

The product was identified as 2'-isopropoxy-6-methyl-N- (n-propoxymethyl) -2-chloroacet.silide.

Example 1.4. ,

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

However doors are less tolerant than the Kulturpflanzen..Für above generally opposite the inventive herbicides the skilled artisan will appreciate that not all of the weeds above selectively through all inventive compounds in all conditions, which air _s Bodenartj moisture and / or method of application be -, hits, controls, becomes.

To illustrate the unexpectedly superior properties of the compounds of the present invention both on an absolute and relative basis5, comparative greenhouse and field assays were performed with:

1. Known compounds which are closest in their chemical structure to the compounds according to the invention

'are; , ,

2. other homologs from the area of the known compounds known, which possess outstanding herbicidal properties; , , ·

3. commercial. Herbicidal compounds whose chemical structure is generally related to that of the compounds of the invention. All compounds in the comparative assays listed below are generally defined as substituted phenyl-N-alkoxyalkyl-2-haloacetanilides. In the tables the compared known compounds are identified as follows:

Elemental Analysis: Calculated for C ^ H ₁₈₃

C: 59.26; H: 6.39; N: 6.94; .Cl: 12.49. Found: C: 59.20; H: 6.41; N: 6.95; Cl: 12.52

The product was identified as 2 ^{L of} ethoxy-N- (allyloxymethyl) -2-chloroacetanilide.

It has been found that the herbicides of the present invention are unexpectedly superior as pre-emergence herbicides, especially for the selective control of hard-to-kill perennial and annual weeds; these include perennial weeds such as couch grass and yellow reed grass, one-year broadleaf

oily weeds such as thorny sida, hemp sesbania, datura, knotweed plants, - reporting, goosefoot plants, as well as annual grasses such as sorghum halepense seedlings, shattercane, brachiaria plantaginea, texan panicum, red rice, wild millet, raoulgrass, foxtails (eg large), Barnyard grass and large Digitaria; Also, as compared to known acetanilides, improved weed reduction in other resistant species, e.g. Ambrosiaceae, Abutilon, Winds and Xanthium scored.

Selective control and improved repulsion of the above-mentioned weeds with the herbicides of this invention has been observed in a variety of crops, including soybeans, cotton, peanuts. Rapeseed and bush beans. Selectivity has also been demonstrated in some tests on sugar beet, field corn, sweet corn, wheat, barley and sorghum; these KuI

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A. 2 ^t ~ ^t ~ methoxy-6-tert-butyl-N- (methoxymethyl) -2-chloroacetanilide (Example 18, U.S. Patents 3,442,945 and 3,547,620). . ' .

2 ^t -methoxy-6'-tert-butyl-N- (methoxy-ethyl-ethyl) -2-bromoacetanilide (Example 34 of U.S. Patent 3,547,620 and U.S. Pat

Example 36 of US Pat. No. 3,442,945). "

C. 2 ^{T, l} 6 -diethyl-N- (methoxymethyl) -2-chloroacetanilide

(Example 5 of U.S. Patent Nos. 3,547,620 and 3,442,945, this compound is known by the name "alachlor" and represents the active ingredient in the commercial herbicide LASSO, registered trademark of Monsanto Company).

D. 2 ^t -Methyl 6'-ethyl-N- (ethoxymethyl) -2-chloroacetani-

lid (Example 53 of US Pat. No. 3,547,620, general designation "acetochlor").

E. 2 ¹ , 6 ^l -dimethyl-N- (isopropoxymethyl) -2-chloroacetanilide (Example 31 of U.S. Patent 3,547,620 and Example 33 of U.S. Patent 3,442,945).

F. 2'-methoxy-6'-methyl-N- (methoxyethyl) -2-chloroacetanilide (Compound No.6 of BE-PS 810,763).

G. 2'-Methoxy-6- ^t- methyl-N- (ethoxyethyl) -2-chloroacetanilide (Compound No. 7 of BE-PS 810,763).

H. 2'-methoxy-6'-methyl-N- (1-methoxyprop-2-yl) -2-chloroacetanilide (Compound No. 9 of BE-PS 810 76 3) and

I .. 2 ^I -methyl-6 ^L -ethyl "N - (1-methoxyprop-2-yl) -2-chloroacetanilide (US Pat. No. 3,937,730, general name

f% f * \ f%

"Metolachlor"; this compound is the active ingredient in the commercial herbicide "Dual", registered trademark of Ciba-Geigy Corporation).

In pre-emergence herbicide tests, compounds of the invention were compared with the known compounds A to I for the control of several perennial or annual weeds, the severely killed species infesting predominantly important crops such as soybeans, cotton, peanut oilseed rape and bush beans , were particularly taken into account. The test results are summarized below.

In the following discussion of the data, reference will be made to herbicidal rates represented by "GR." And "GRg ₅ "; these amounts are given in pounds per acre (lbs / A), which is. can be converted by multiplying it with I ₅ 12 in kg per hectare (kg / ha). GL ₁ - defines the maximum amount of herbicides causing damage to 15% or less of the crops, while GR _{c is} the minimum amount necessary to achieve an 85% inhibition of the weeds. The GR. - and GR '^ amounts are used as a measure of the potential performance of commercially available products, of course, suitable commercial herbicides within reasonable limits may have greater or lesser plant damage.

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Another note 'on. the effectiveness of a chemical as a selective herbicide is the "selectivity factor"("SF") for a herbicide in certain crops and weeds. It is a measure of the degree of harmlessness of crops and is expressed as the ratio GR '- / GR, ie GR. (Quantity of crop divided by GR _O p ^ amount for the weed, both amounts expressed in lhs / A biw kg / ha. In the tables, the selectivity factors, if used, are given in parenthesis after the weed "NS" means "non-selective", insignificant or indefinite selectivity is indicated with a dash after the weed, a blank indicates that the plant species was not involved in a particular test, that the data was not obtained for any reason For example, shorter-term observations, such as long-term data, are not reported, or longer-term data are omitted because data were definitive for a shorter term for a given herbicidal activity.

Since crop tolerance and weed control are _{interrelated%} is a kur'ze discussion of this ratio, expressed as a selectivity factor, attached. In general, it is desired that the harmlessness factors for the crop be high * because, for one reason or another, higher herbicide concentrations are often desired.

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Conversely, for economic and possibly ecological reasons, the amounts for weed control should be small, i.e., the herbicide should have high activity of activity. However, small amounts of a herbicide may not be enough to control certain weeds, and more is needed, so the best herbicides are those that control the largest number of weeds at the lowest rate and the greatest harmlessness to the herbicide Thus, the selectivity factors (defined above) are used to quantify the relationship between crop harmlessness and control of weeds, and for the selectivity factors listed in the tables, the higher the numerical value, the greater the selectivity of the herbicide for the weed control in a given culture.

The listed pre-emergence tests include both greenhouse and field tests. In the greenhouse tests, the herbicide is either applied to the surface after planting seeds or offshoots, or it is incorporated into a certain amount of soil to be spread over test seeds in seeded test containers as a topcoat. In the field tests, the herbicide is pre-seeded Plants incorporated into the soil (PPI) ie, it gets to the earth's surface

applied, then mixed with the soil, then the crop seeds are planted out.

The surface test method used in the greenhouse is carried out as follows: Containers, eg aluminum pans of about 2 x 4x13x7 cm, or plastic pots of about 9,5x9,5x8 cm, with drain holes in the bottom, are filled to the brim with Ray Schlufflehmerde, then to to a height of 1 _S 3 cm below the pot edge is tapped. The pots are then seeded with a plant species to be tested and covered with a 1.3 cm high layer of the tester's debris. The herbicide is then applied to the earth's surface with a belt sprayer.

brought: (187 l / ha, 2,11 kgf / cm); on occasion, other spraying devices, e.g. a DeVilbiss sprayer • uses. Each pot is watered from above with 0.64 cm of water, then the pots are placed on garbage tables and watered as needed from 'below. In an alternative method, the irrigation from above can also be omitted. About 3 weeks after the treatment, the effect of the herbicide is determined. '

The herbicide treatment by incorporation into the soil is done in greenhouse tests as follows:

Good topsoil is placed in aluminum pans and tapped down to 1 to 1.3 cm below the rim. On the earth will be a number of seeds or offshoots of various plant species

distributed. 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 the treatment, the pans are given an initial irrigation, which corresponds to 0.64 cm of precipitation, then they are watered from below as needed, so that adequate moisture for germination and growth is present. The irrigation from above can also be omitted. Appraisal takes place about 3 weeks after sowing and treatment.

Table II lists the data for herbicidal activity in a first pre-emergence test series; This compares the relative efficiency of compounds of the invention with related known compounds in the control of yellow reed grass and couch grass in soybean, cotton and maize crops.

Table II

Quantity for GRg ₁ . (kg / ha) Quantity for (kg / ha)

Compound Cyperus Wheatgrass

E F

G H

Ex. 1

> 2.2

0.69 0.45 0.2

0.17 0.34

0.25

1.5

1,7, 0,10

1.6 2.8 0.56 0.18

0.27 0.20 0.36

0.9 0.2

soybeans

cotton

3.1 (-) 0.28 (NS)

0.56 (NS) .1.1 (NS)

1.7 (4)

1.1 (2)

0.39 (1.5 0.39 (2)

0.21 (1)

0,2l '(NS) 0,21 (NS)

<0.07 (NS) <0.07 (NS)

2.2 (1.5)

2.2 (6)

<1.7 (NS)

1.3 (1.5) 0.2 8 (3) 0.28 (1.5:

0.25 (1)

0.48 (3)

0.21 (NS)

0.39 (1.5)

2.9 (2) 2.7 (7.5)

: l, 7 (NS.) 1.3 (1.5) 0.2 8 (3)

Corn

0.17. (NS) 0.28 (NS)

0.034 (NS) 0.07 (NS)

0.78 (2) 0.84 (1.5)

0.22 (1) 0.22 (1)

0.09 (NS)

<O, 22 (NS) <O, 22 (NS)

<0.07 (NS) <0.07 (NS)

<1.5 (NS) 1, 25 "(3, 5)

<1.7 (NS) <0.9 (NS) <0.07. (NS) <0.07 (NS)

CiS? ΰ I

Table II - continued

Second amount , for GR ₈₅ Abandon soy Quantity for Eq ) Corn (NS) 3 (k s / ha) 0.17 (1) 0.13 (2) ' (kg / ha). 0) <0.17 <0.07 (NS) 4 Cyoerus couch-grass 0.77 (3) 0.81 (6) cotton 0) <O, 26 (NS) 5 0.17 0.07 1.0 (3.0) 1.0 (4.5) 0.17 (1) 0.07 (1) ) <0.34 <O, 22 (NS) connection 5 Ο, · 2 6 0.13 3,4 (12,0) 3,4 (12,0) 0.7 7 (3) 9) <O, 28 <O, 28 (NS) Ex. 7 0.34 0.22 2.0 (8.0) 2.2 (8.0) 1.0 (3rd, 0th ) <O, -26 <0.23 (NS) '(NS) Ex. 8th 0.28 0.28 0,90 (4,0) 0,90 (1,6) 2.8 (10, <0.15 <0.15 (NS) Ex. , 9 .0,26 0.2 8 0.56 (1.5) 0.56 (3.3) 2.5 (10, <0.13 <0.13 (NS) Ex. 0,2 2 0.56 5,6 (10,0) 5,5 (11,9) '1.5 (5.5 <O, 28 <O, 23 Ex. 0.37 0.17 0.72 (1, Ex. 0.56 0.47 1.7 (3.0 Ex. Ex.

Table II _ Continued '

Quantity for GRg

(Kg / ha)

Compound Cyperus Wheatgrass soybeans

Quantity for (kft / ha)

cotton

Corn

Ex. 12 Ex. 13 Ex. 14

0.12 0.2 2 0.36

0.11 0.2 8 0.50

0.28 (2.5) 0.28 (2.5)

0.45 (2.0) 0.56 (2.0)

> 5.6 (> 15.6> 5.6 (> 11.1

0.25 (2.0) 2.7 (12.0) 1.4 (3.9)

<0.12 (NS) <0, ll (NS)

<O, 22 (NS) <O, 28 (NS)

5,6 (15,6) 5,6 (11,1)

- pr -

From Table II it can be seen that in general the compounds of the invention are significantly more active as a class, i. have a higher unit activity against Cyperus esculentus and couch grass, and a higher harmlessness to soybeans and cotton than the reference compounds. ',

With regard to the control of Cyperus esculentus, it should be noted that each tested compound of the invention tested was significantly more active than Compounds A and B, which are structurally different from the reference compounds; and also as compound H, which is less related than A and B, but which in some respects may be considered more closely related to the compounds of the invention than are compounds C, D, E and I. In particular note that the compound of Example 1 with a _0.85 kg / ha GR _{ß5 was} about 2 times as active as the most active reference compound E (GR _RI -0.17 kg / ha); times as high harmlessness factor as compound E for soybeans and an equivalent harmlessness for cotton possessed. The compounds according to the invention of Examples 2 and 12 also had equivalent or greater unit activity than Compound E over Cyperus esculentus. Although reference compounds F and G have fairly high unit activity, none of the compounds were selective to Cyperus

in soybeans, compound F was still selective in cotton. Compound G checked though. Cyperus in cotton, but the harmlessness was lower than that of all compounds of the invention, except Example 2, and significantly lower than that of Examples 5,6 and 13. The selectivity factors of the compounds of Examples 9 and 14 against Cyperus in soybeans were particularly outstanding.

Regarding the Quecken control, the compound of Example 2 was nearly 3 times as active as the most active reference compound, Compound D, while achieving equivalent harmlessness to soybeans. The compound of Example 3 according to the invention had a higher unit activity against couch grass and a 3 times higher harmlessness for soybeans such as compound D. Again, it should be noted that each fiction, -gette tested compound against Quecke excellent superior unit activity compared to the compounds A and B. ., which are the closest related reference compounds tested. Although the unit activity of Compound H over Wheatgrass was slightly higher than in the compounds of Examples 9-14, the selectivity factors of these latter compounds in Wheatgrass in soybeans were about 2 times those of Compound H, the closest related reference compound. Incidentally, the reference compounds A, B,... F and G were not selective to whey in soybeans.

Table II also shows that of all the compounds tested, the compounds of Examples 5, 6, 9 and 14 had by far the highest harmless factors for soybean relative to cyperus and couch grass. The compounds of Examples 5, 6 and 13 further had the highest safety factors for cotton, relative to Cyperus escu- 'lentus. It should also be noted that the exceptionally good harmlessness factors of the compounds of Examples 5, 6, 9, 13 and IU were associated with very low levels of GR _O. , Indicating high unit activity against cyperus and couch grass. In these tests, most compounds of the invention were not selective in quays, the same applies to all but three reference compounds. The compound of Example 14, however, showed exceptionally superior selectivity relative to couch grass and cyperus in maize.

In further comparative tests, the herbicidal pre-emergence activity of reference compounds C and D and the compound of Example 1 was tested on various annuals of broadleaf weeds at a rate of 3.36 kg / ha. The assessment was carried out 6 to 7 weeks after treatment (WAT) and the percentage control of weed growth was recorded. The data from this test are summarized in * Table III.

Table III

Control of annual broadleaf weeds

Leading run »'6 to. 7 WAT

weed % Control on connection 3, C 36 kg / ha example 1 35 D Sida Spinoza 93 0 73 Sesbania exaltata 100 62 69 Amaranthusj 83 64 88 Polygonum 88 61 , 76 reporting 75 53 81 Ambrosiaceae 72 68 43 Datura 98 9 8

From Table III it can be seen that the compound of Example 1 showed outstandingly superior activity compared to Compound C over each broadleaf weed tested. Likewise, the compound of Example 1 exhibits markedly superior activity compared to Compound D over Sida spinosa, Sesbania exaltata, Polygonum and Ambrosiaceaes while having equivalent activity against datura, and slightly lower Amaranthus activity and reporting. ,

For further comparisons, field tests were performed to assess the relative pre-emergence activity and selectivity of the compound

of Example 1 compared to the reference compounds C, D, E and I towards Echinochloa, Sidä spinosa and Sesbania exaltata in soybeans. These tests were conducted on individual parcels of Sharkey clay containing 2.0% organics; this was behandelt- with various concentrations of each herbicide which ί as an emulsifiable concentrate in an up-

amount of 2 80.6 l / ha was applied. The assessment took place H weeks and 7 weeks after the treatment. The test data, which are based on 3 runs, show that after 7 weeks only the compound of Example 1 selectively controlled Sesbania exaltata; this control (GRgr) was reached at only 1.9 6 kg / ha, while GR _{8I was} 5.6 kg / ha for each of compounds C, E and I and 5.0 kg / ha for compound D. GR. . in soybeans was 3.9 kg / ha, giving a 2.0-fold safety factor for Example 1 compound. Thus, in order to achieve the same GRpr-number, approximately three times the amount of the compound of Example 1 was required for the reference compounds, but without selectivity in soybeans.

Compounds C and D were non-selective to Sida spiapsa in soybeans at 7 VJAT. Of compound I were 4.2 kg / ha and compound E 2.8 kg / ha to achieve GR _O r and 1,1-resp. 1.5 times selectivity factors required. With compound of Example 1, however, GRoc at 0.8 kg / ha and a 4.7-fold selectivity factor in

- /> he

Soybeans reached. ·

Compounds C, D and E were non-selective at 7 WAT over echinochloa in soybeans. Compound I and Compound of Example 1 had virtually equivalent innocuity factors, i. 1.5 times compared to '1.4 times. ,

The field tests thus show that, with the exception of comparable control of echinochloa by Compound I, the compound of Example 1 was significantly superior to Reference Compounds C, D, E and I in the selective control of all three annual weeds in soybeans 7 weeks after treatment.

In further tests to determine the relative herbicidal activities and selectivities over even longer periods of time, the same herbicides were again field-tested as in the previous tests, this time in individual plots of silty clay to schluffige clay with 3 _s 0 to 3.5% share on organic matter. In parallel tests, emulsifiable concentrates of the respective herbicides were applied to the surface for pre-emergence control or incorporated into the soil prior to planting, again at 280.5 l / ha containing the appropriate herbicidal concentration as the active ingredient! In these tests, herbicides have been used in the control of perennial

J-% άΖ * ύ

year old broadleaf weeds Ambrosiaceae, Amaranthus and Polygonum in soybeans. These tests were subject to heavy rainfall, 4.4 5 cm on the fifth day after treatment ("DAT"), and 2 ₅ 29 cm, 1.52 cm, 1.27 cm on the following days. The data is shown in Table IV. ,

Table IV pre-emergence activity

Incorporation before planting GR ₈₅ ~ quantity (kg / ha)

GR ₁₅ quantity (kg / ha)

connection 1. WAT Wheatgrass Ambrosiaceae 5.6> 6.7 Amaranthus 2 _} 5 2.5 4.5 4.5 5.0 4,5 3,4 Polygonurri soybeans Ex. to cn co cn 2.2 2.2 2.5 · > 6.7> 6.7 2.2 5.9> 6.7> 6.7 > 6.7> 6.7 , 4.5 5.0 2.5 .3.4 1.7 2.5> 3.4 C 3 6 9.5 > 6.7> 6.7> 6.7 > 6.7,> 6.7 > 6.7 > 6, V> 6,7 > 4.5> 4.5> 4.5 D. 3 6 9.5 5.6> 6.7 6.7 > 6.7> 6.7 > 6.7 5.6> 6.7 3, 9 4,2 4,5 e 3 '6 9.5 > 6.7> 6.7> 6.7 > 6.7> 6.7 4.2 · 4,5 4,5 2.2 2.8. 4,2 ' I 3 6 9.5 > 6.7> 6.7> 6.7 > 6.7 > 6.7 5.9 1.7 3.9 5.0 1 Surface treatment Ex. 3 6 9.5 3,4,4,8 1.5 3.4 4.2 C 3 6 9.5 > 6.7 5.9 3.9 2.2> 4.5

Table IV - Continuation pre-emergence activity

Training before planting

GR ₈₅ quantity (kg / ha) · GR ^ quantity (kg / ha)

Connection- WAT couch-grass An> bros laceae Amaranthus , 7 Polygonum • 4,5 " Abandon soy D- ·. 3 > 6, 7 , 0 5.6 0.34 6 > 6.7 > 6 , 7 6 7.0 3.9 9- 5 > 6, 7 > 6 , 7 5 , 6 • 6,7 > 6.7 5, 3 e 3 5.6 , 0 > 6, 7 • 2.5 6 > 6.7 > 6 , 7 5 2.0 9.5 > 6, 7 > 6 , 7 5 , 7   4.8 to, * I 3 > 6.7 , 7 4.5 6 > 6, 7 > 6 -.7 > 6 4.5 9.5 > 6.7 > 6 , 7 > 6 4.5

Table IV shows that when incorporated prior to planting, none of the reference compounds at rates of 6.7 kg / ha, maximum test amount, 6 weeks, and 9.5 weeks after treatment selectively controlled any of the weed tested weeds. As already mentioned, the selectivity is given by the selectivity factor, ie the ratio GR.r / GRg ₅₅ which gives a value of 1.0 or more; the higher the value, the greater the selectivity. The compound of Example 1, on the other hand, showed selective control of couchwort, .maranthus and. Polygonum 6.0 WAT, and control of Wheatgrass and Polygonum 9.5 WAT. The herbicidal activity of the compound of Example 1 is on the order of 3 times or greater than that of the reference compounds against wheat and polygonum (excluding compound D), and about 2 times or more as active as the reference compounds (excluding compound D 6 and 9.5 WAT and Compound E 9.5 VJAT). None of the herbicides selectively controlled Ambrosiaceae in this assay, but the compound of Example 1 was 6 VJAT more active towards this weed than the reference compounds.

Also, in the herbicidal surface application tests, none of the reference chemicals of one of the soybean weeds selectively controlled at rates of 6.7 kg / ha at 6 and 9.5 WAT, respectively, except compound D at 9.9 in Amaranthus. Selective weed control of the compound of Example 1 in wheat and poly

gonum observed at 6 WAT, and at 9.9 WAT Amaranthus; the factor of harmlessness was slightly greater than that for compound D, i. 1.3 times greater than 1.1 times. Also in these tests, the compound of Example 1 showed a much higher herbicidal activity than the reference compounds. , '

From the table it can be seen that, due to the following criteria, namely the unit activity against the weeds, the tolerance of the soybeans to the herbicides, the harmlessness factors and the methods of application, the compound of Example 1 had substantially superior properties as a pre-emergence herbicide than the comparative reference. · Links.

The sustained weed control by the compound of Example 1 under heavy precipitation showed that the compound did not leach out easily.

Further field comparison tests tested the compounds of Example 1 and Reference Compounds D and E 'for the selective control of Sida spinosa and Digitaria sanguinalis in cotton, where the herbicide was applied both to the surface and to the soil before planting 'incorporated; Yellow sedge grass was included in the pre-plant incorporation test. The soil used for the tests was loam clay with

1.7% organic share. Assessment was done 2, 6 and 9 weeks after the treatment. The data for the application on the surface, which are based on 3 runs, show that Compound 1 possessed more than 2 times the unit activity over Sida spinosa, such as Compounds D and E at 6 WAT, and 1.5 times their activity at 9 WAT. Compound D was non-selective to Sida spinosa in cotton at 6 and 9 WAT, respectively. The selectivity selectivities for Compound E 'at 6 and 9 WAT, respectively, were 1.1 and 1.3, respectively, compared to 3.3 and 1.8 for the Compound of Example 1. Although the unit activities of each tested Compound versus Digitaria were at 6 WAT were comparable, the compound of Example 1 at 9 ViAT was more active than Compound E, and more selective (ie, S-.F,> 4.0) than Compound D, the SF 2.8.

In the pre-plant herbicidal incorporation tests, the unit activity of Compound Example 1 after 9 WAT over Cyperus was over 2 times greater than that of the reference chemicals, slightly less than 2 times greater for Digitaria, and greater than 11 for Sida spinosa / 3 times as big. In this field test, the compound of Example 1 Cyperus in cotton selectively controlled up to 6 VJAT, while the reference chemicals did not show selectivity even at 2 WAT. None of the test chemicals selectively controlled Sida spinosa in this PPI test, the compound of Example 1 was compared to the other compounds

¥ 3

but much better. The compound of Example 1 and Compound E controlled Digitaria at just 2 WAT, but warm thereafter non-selectively; Compound D was at no time selective to Digitaria.

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

Further comparative tests were conducted with the compound of Example 1 and compounds D and E to determine their relative herbicidal activity and soil duration of the perennial weeds Cyperus exculentus and Wheatgrass. Compounds D and E are among the most active selective herbicides of the known 2-haloacetanilides and have been classed as standards in this class of tests for other herbicides against Cyperus and Wheatweed and other weeds. At the here discussed

-IyC

h u

Tests were carried out for 2 runs. Each treatment planted 25 cyperus tubers and 2.5 pieces of heather rhizomes. The herbicides were incorporated into the soil cover layer with amounts sufficient to determine the amount of GR ' ₀ , ie the minimum amount necessary to achieve 50% control of the weeds; 11.2 kg / ha was the

'-

Maximum quantity, and 1.4 kg / ha, the minimum quantity actually applied. Appraisal was done 3, 6, 12 and 18 weeks after the treatment. After each inspection, the soil cover layer was removed, the old tubers and rhizome fragments removed, planted again, then placed in the greenhouse for the next cycle. The test results are summarized in Table V, "VJAT" means "weeks after treatment".

Table V Duration of action in the soil , GR ₅₀ kg / ha connection Cyperus esculentus Beisp.1 <1.4 1.4 8.4 D 1 * 12 5.9 •. e * 1 * 4 7,8> 11 ₅ 2

couch-grass

1.4 11.2

<1.4 1.4 5.6

1.7 • 11.2

WAT

12 18

12 18

12 18

O Q / 1

The counts for the control of Cyperus in Table V show that at 3 WAT, the GR, -Q amount of each compound was below 1.4 kg / ha, while at 6 ViAT some significant differences occurred. At 12 WAT significant differences in the control of Cyperus were evident. While only 1.4 kg / ha of the compound of example! were needed to. To control 50% of the weeds required 5.9 kg / ha of compound D and 7.8 kg / ha of compound E to achieve the same degree of control over Cyperus esculentus. , At 18 WAT only 8 ^ 4 kg / ha of the compound of Example 1 was needed for the 50% control of Cyperus, compared to a mean value above 11.2 kg / ha (the maximum used) of Compounds D and E.

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

A key benefit of a herbicide is its ability to act in a variety of soil types. Accordingly

For example, Table VI summarizes the herbicidal activity of the compound of Example 1 aif Cyperus in cotton and soybeans in a variety of soil types having varying levels of organics and clay. The herbicides were incorporated into the soil, the seeds planted 0.9 5 cm deep, watered from the top with 0.6 4 cm. The assessment took place 18 days after the treatment.

- / 5

Soil table VI Volume, % ^GR 85 (kg / ha) ^GR 15. (Kg / ha] ) soybeans connection Ray sissy Organic shares,% 9.6 Cyperus cotton 0.56 Ex. 1 Sarpy clay clay • 1.0 - 0.22 0.73 0.95 Georgeville silty clay clay 2.3 37.0 '0.07 0.95 0.56 Wabash clay clay 2.9 33.0 0.12 0.47 0.95 Drummer silty clay clay  ♦, 3 37.0 0.22   1.12 0.87 Florida sand 6.0 1.8 0.22 0.95 0.4 8 6.8 0.27 0.5 6

From Table VI it can be seen that the compound of Example 1 appears to be quite insensitive to soil type and organic matter content; it shows selective control of Cyperus in both cotton and soybeans in soils containing 1.0 to 5.8% organic matter and 1.8 to 9.6% clay. The selectivity factors were highest in Sarpy Tonlehm.

Further tests were carried out to determine the herbicidal performance of the compound of Example 1 in soils with a high content of organic matter. In three repeated field tests, the activity of the compound of Example 1 versus Amaranthus and reporting was tested in soybeans planted in black peat. Compounds C, D, E and I were also tested for comparison. These tests were carried out with both methods of application, namely incorporation into the soil or application to the surface, carried out in black peatland containing 2-3% organics. In these assays, the compound of Example 1 exhibited the highest unit activity in both the P.P.I. and S.A. procedures against the 4.WAT reporting and, in the P.P.I. method, the highest selectivity factor in soybean, i. greater than 2.7 versus 1.1 for each of compounds C and D; Compounds E and I were non-selective at 4 WAT. All compounds were non-selective to reporting at 7 WAT, and although not in either application method;

H- 9

Compound E was slightly more active than the compound of Example 1 at 7 WAT 'in both methods of application. Compared to Amaranthus, the compound, D has the highest unit activity and the highest selectivity factor (1.9), 7 WAT in both methods of application; in the surface application method, the selectivity factor of the compound D was almost 2 times that of the compound of Example 1 and Compound E; no other compounds selectively controlled Amaranthus at 7 WAT in either application. The compound of Example 1 (S.F. 2.0) and Compounds C and E (S.F., 1.0 each) selectively controlled Amaranthus H WAT by the P.P.I. method.

Thus, the above tests show that, when compared to the reference compounds in black peat, the best selective control of reporting in soybeans is obtained when the compound of Example 1 is incorporated into the soil; this compound had the highest unit activity and the highest selectivity factor at 4 WAT of all tested compounds. In addition, the compound of Example 1 selectively controlled Amaranthus up to 7 WAT by the surface method, and up to 4 WAT with the P.P.! Method. Compound D gave the best control of Amaranthus at 7 VJAT with both application methods. The relative performance of the compound of Example 1 and Compound D in

black peat should be further compared to the relative performance of these two compounds in soils containing less organic matter, e.g. 3.0 to 3.5% in which the compound of Example 1 shows superior soil activity and soil life along with selectivity to soybean in both applications, as shown in Table IV.

The above description emphasized the excellent herbicidal activity of the compounds of the present invention in controlling perennial weeds and annual broadleaf weeds in soybeans and cotton. Furthermore, it was mentioned above and occasionally also shown e.g. in the. Tests with Echinochloa and Digitaria indicate that the compounds of the invention also exhibit excellent herbicidal activity against annuals of narrow-leaved weeds, i. Grasses, own. In fact, compounds of the present invention, as will be illustrated below with respect to particular annual grasses, demonstrate marked superiority over the herbicidally most active and / or commercially available known 2-haloacetanilides. From the test data, cases are seen in which a related known 2-haloacetanilide shows superior herbicidal activity compared to compounds of the invention with respect to certain annual weeds under comparable conditions. From the comparative tests available here, however, it is also apparent that inventive. Total connections

the best 2-haloacetanilides as selective herbicides for the control of annual and perennial narrow-leaved weeds in soybeans. Cotton, peanuts and other crops are at least comparable and often superior, sometimes outstanding.

In a pre-emergence test in the greenhouse, the compounds of Examples 1 and 11 with compounds C and E (both being commercial 2-haloacetanilides) were evaluated for their relative herbicidal activity against one-year narrow-leaved weeds, i. Grasses tested in soybeans. In this test, the herbicides were incorporated in the soil before planting the seeds, and the observation was carried out and recorded 17 days after the treatment; the test data are summarized in Table VII and represent the average of 2 passes.

Table VII

GR ₈₅ Amount GR ^ Amount

(kg / ha) (kg / ha)

Pani-Rottboellia

Sorghum h, sorghum cum milia- Oryza exaltata compound seedlings bicolor brachia ceum sativa soybeans

Ex. 1 0.14 0.84 ' 0.28 0 , 56 0 , 95. 0 , 84 Ex. 11 0.28 0.2 8 0.14 .. o , 56 , 1 ,1 0 , 28 C 0.56 0.28 0.28 0 , 56 1 ,1 1 ,1 I 1.1 1.1 0.56 > 1 ,1 > 1 > 1 1

Looking at the data in Table VII, the following are

Main points to note:

1) Compound I showed the lowest unit activity and selectivity of all compounds over each weed tested} and showed no selectivity in soybeans with respect to Panicum miliaceum, Oryza sativa or Rottboellia;

2) Compound C was as active as the more active compounds of Examples 1 and 11 over Sorghum bicolor and Panicum miliaceum;

3) The compounds of Examples 1 and 11 were both superior to the known compounds in sorghum halepense seedlings and Rottboellia, and

U) the compound of Example 11 was more active towards Brachiaria pl. ₉ and the compound of Example 1 was more active towards Gryza s. as the known compounds.

From the comparative data of Table VII it can be said that one or the other of the two compounds according to the invention was herbicidally active against two one-year narrow-leaved weeds (Sorghum bicolor and Panicum miliaceum) as well as the best known reference compounds, and clearly better against four narrow-leaved weeds ( Halepense sorghum seedlings, Brachiaria plantaginea, Oryza sativa and .Rottboellia exaltata). Of particular note is the excellent unit activity of the Compound 'of Example 1' over sorghum

th

ryji '* ^ - * - * ** "β Β ·

halepense seedlings (GR ₈ ^ = O ₉ IU kg / ha), giving an excellent selectivity factor of about 8.0 in soybeans, compared to a selectivity factor of> 2.0 for compound C, which is the better of the known compounds tested is. Similarly, the compound of Example 11 showed excellent unit activity against Brachiaria pl. and Rottboellia e., with selectivity factors of> 8.0 and *> 4.0, respectively, in soybeans compared to respective selectivity factors of> 4.0 and> 1.0 for compound C.

In soybeans, another test was performed using seeds from Texas and autumn panicum in addition to the other annual grasses already mentioned in the previous test. In this test, the compounds of Examples 1 and 12 were compared with the known compounds C, D and I for their herbicidal pre-emergence activity. The herbicides were incorporated into the soil and irrigated from below as needed. The maximum amount of herbicide that was used in this test was 1.2 kg / ha, which are genauen- GR _R _- and GR .. ^ quantities over 1.2 kg / ha therefore uncertain to some extent. Assessment was made two weeks after treatment, the data of this test are summarized in Table VIII.

Table VIII

, GR ₁₅ ~ Quantity (kg / ha) ' ___ (kg / ha)

Panicum Sorghum Sorghum Bracha- Panicum Autumn- Oryza Rott-

Connection tex. · H. bicolor ria pi. m. panicum sativa boellia e. So abjhnen

<0.07 0.28 0.56> 1.1

<0.07 0.21 0.07> 1.1

<0.07 0.28> 1.1> 1.1 <0.07 <0.07 0.56 1.1

<0.07 0.56 0.84> l, l '

Ex. 1 1.1 <: 0.07 0.14 0.56 0.56 Ex. 12 0.28 <0.07 0.14 0.14 0.56 C 0 ·, 5 6 0.07 0.2 8 0.56 ' 1.1 D 0.14 0.07 0.28 0.07 0.56 I > 1.1 0.28 0.50 0.50 1.1

An analysis of Table VIII reveals that the compounds of Examples 1 and 12 of this invention exhibited the highest unit of activity and selectivities of all compounds tested against sorghum halepense and sorghum b.icolor; the compound of Example 12 had the highest activity and selectivity to Rottboellia, and the compounds of Examples 1 and 12 had the highest activities over Pancreatic miliaceum along with Compound Dj and against Autumn spanicum along with each of the known compounds. However, the compounds of this invention were more selective in soybeans than Compound D with respect to Panicum miliaceum. The compound of Example was also the second most active compound against Panicum texanum and Oryza sativa, and the compound of Example! had the second highest activity against Rottboellia along with Compound D. Compound D was the most active test compound against Panicum texanum, Brachiaria p. and Oryza sativa.

From the foregoing comparative data on the herbicidal activity towards other grasses, it is therefore apparent that the compounds according to the invention have a herbicidal activity which is superior to that of the leading related known compounds over certain annual grasses, e.g. against 'Echinochloa, Digitaria (S.I.), Sorghum bicolor and Rottboellia, and that they have an equivalent or generally comparable herbicidal activity

<Γ7- &·> L · Ö £!

to other weeds, e.g. towards Digitaria (S.A.), Panicum species, Brachiaria and Oryza sativa. ''

Other greenhouse and / or field tests have found selective control by the compounds of the invention of other weed species in soybeans, cotton and / or other crops. For example. the compound of Example 1 selective control of purple cowslip and Setaria faberi in cotton, and Setaria faberi and Abutilon th. in soybeans. Compared with known related acetanilide herbicides, the compound of Example 1 showed improved repellency of such resistant weeds as Ambrosiaceae, Ipomoea and Xanthium. Other weeds to which the compounds according to the invention have proven to be herbicidally active, i.a. Creeping thistle, field winch, fluffy Trespe> Windscrew etc.

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

In a greenhouse test, the herbicidal pre-emergence efficacy of the compounds of Examples II and II. 12 tested,

and indeed, incorporated into the soil, against couch grass in rape, bush beans, sorghum and wheat. Both compounds tested selectively controlled wheat grasses in rape and bush beans, the selectivity factor of the compound of Example 11 was 3.5 in both crops, that of the compound of Example 12 was 3.0 in both cultures. In this test, both compounds were not selective for wheatgrass in wheat and sorghum.

In separate greenhouse tests, the compound of Example 1 was also tested for its herbicidal activity against yellow grassgrass in oilseed rape, peanuts, sugar beets, sorghum, wheat and barley; the herbicide was incorporated into the soil. In these tests, the compound D was used as a reference compound against seaweed, and the compound E as a reference compound against yellow reed grass. In the testis with Wheatgrass, the evaluation was carried out 19 days after the treatment (DAT), in the test with yellow reed grass 18 DAT; the test data are summarized in Table IX; the selectivity factors for the herbicides are given in parenthesis after the GR.r levels for the respective cultures, j

Table IX

Weed culture

^GR 85 ^GR 15 (kg / ha); (kft / ha)

Compound Quecke Peanuts Rapeseed Beet Sorghum Wheat Barley

0.28 (6.0) 0.13 (3.0) 0.28 (6.0) <0.034 (NS) 0.06 (1.0) 0.07 (1.5)

0.034 Ö, O34 ('l, O) 0.06 (1.5) 0.06 (1.5) <0.034 (NS) Ό, 034 (1.0) 0.11 (3.0)

Ex, 1 0,045 • D 0.034 Cyperus esculentum Ex. 1 0.12 · e 0.12

0.87 (7.0) 0.48 (4.0) 0.022 (NS) 0.13 (1.0) 0.13 (1.0) 0.28 (2.0) 0.95 (8, 0) 0.87 (7.0) 0.022 '(NS) 0.011 (NS) 0.105. (NS) 0.13 (1.0)

ίο

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

The high unit activity of Compounds D and E appearing in Table IX is characteristic of short-term greenhouse performance (i.e., 2 to 6 weeks) in these compounds against Wheatgrass and Cyperus esculentus. However, with the relevant test data from both greenhouse and field assays compiled here, it has been demonstrated that the compound of Example 1 over compounds D and E has uniformly superior unit activity against couch grass and cyperus and superior selectivity in cultures for much longer time periods. In this context, reference is again made to:

.1) Table IV, which shows comparative data from field trials up to 9.5 weeks for the performance of these compounds against couch grass and other weeds in soybeans; (neither compound D nor compound E controlled couch

-fir-

in soybeans selectively themselves. in .3 WAT); ,

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

3) Table 'V, in which comparative data for the duration of action in the soil of the compound of Example 1 and the compounds D and E: against Cyperus and Quecke for 3, 6, 12 and 18 weeks are included; ^: .

The compound of Example 1 showed unit activities that were higher than those of compounds D and E at 3 WAT (several orders of magnitude in observation 12 'WAT) and an indeterminate value at 18 WAT observation. It should also be pointed out here that the combination of superior unit activity, soil duration and selectivity in cultures of the compound of Example 1 as compared to compounds D and E over Cyperus and Quecke also accounts for the relative performance of these compounds in many others Weeds, especially Sorghum h'alepense seedlings, Sesbania exaltata, Sida sspinosa, Polygonum, etc.

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

In parallel tests, the herbicides were either applied to the surface or incorporated into the soil before planting. Assessment and recording of the data will take place 33 days after treatment in the soil incorporation prior to planting and 34 days after treatment in the herbicidal application tests. In both tests, the compound of Example 1 selectively controlled Echinochloa and Setaria viridia in corn, soybeans, cotton, bush beans and peanuts; Reporting was also controlled in soybeans. In the P. P.I. tests, Echinochloa and Setaria were also selectively controlled in. Sorghum and sweet corn.

It thus appears from the foregoing detailed description that the compounds of the invention exhibited unexpectedly and excellently superior herbicidal properties, both absolutely and in comparison with the structurally most closely related compounds, other related homologues and analogs, and known commercially available 2-haloacetanilides , In particular, the compounds of the present invention exhibited excellent unit activity, soil duration, and harmless cultures in the control of perennial and annual broadleaf and narrow-leaved weeds in soybeans, cotton, peanuts, rapeseed, bush beans, and other crops. In particular, the compounds according to the invention showed superior herbicidal activity.

^ 3

cidal activity against the perennial weeds Cyperus esculentus and Wheatgrass (Agropyrum repens); one-year-old broad-leaved weeds such as Sesbania exaltata ₉ Sida spinosa, Chenopodium album 'and Polygonum, as well as annual narrow-leaved weeds such as Echinochloa crus-gallii Digitaria sanguinalis (PPI)' Sorghum bicolor and Rottboellia exaltata. In addition, the compounds of the present invention were found to be generally comparable to the best known compounds in the control of other annual grasses such as sorghum häuspense seedlings, Digitaria (SA), fox tails, Panicum species, Brachiaria plantaginea and Oryza sativa, as well as annual broadleaf weeds such as Amaranthus and Datura stramonium. ' Finally, the compounds of the invention showed increased activity in repressing resistant one year old broadleaf weeds such as Ipomoea, Xanthium pensylvanicum, Ambrosiaceae and Abutilon theophrasti.

Toxicological studies of the compound of Example 1 revealed that the compound is quite harmless. It was slightly toxic when taken orally (single dose oral LDr ₀ ~ 2600 mg / kg), slightly toxic with single dermal application (dermal LDcq - 5010 ^ g / kg) - it also produced mild eye and skin irritation. Special handling procedures beyond the normal precautions are not considered riotwendi.g.

The herbicidal preparations according to the invention, including the concentrates which have to be diluted before use, contain at least one active ingredient and an adjuvant in liquid or solid formin. The. Preparations are made by mixing the active ingredient with an adjuvant which includes diluents, diluents, carriers, and conditioning agents to form formulations in the form of finely divided solid particles, granules, pellets, solutions, dispersions or emulsions. Thus, the active ingredient may be used with an adjuvant such as a finely divided solid, an organic-based liquid, water, a wetting agent, a dispersing agent, an emulsifying agent or a suitable combination thereof.

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

(φ-

Preferred wetting agents are alkylbenzene and alkylnaphthalenesulfonates, sulfated fatty alcohols, amines or acid amides, long-chain acid esters of sodium isothionate, sodium sulfosuccinate esters, sulfated or sulfonated fatty acid esters, petroleum sulfonates, sulfonated vegetable oils, ditertiary acetylenic glycols, polyoxyethylene derivatives of alkylphenols (especially isooctylphenol and nonylphenol), and polyoxyethylene derivatives of higher fatty acid monoester of Hexitolanhydride (eg sorbitan). Preferred dispersants are methylcellulose, polyvinyl alcohol, sodium ligninsulfonates, polymeric alkylnaphthalenesulfonates, sodium naphthalenesulfonate, and polymethylenebisaphthalenesulfonate.

Wettable powders are water dispersible formulations containing one or more active agents, an inert stretched solid and one or more wetting and dispersing agents. The inert yield solids are usually of mineral origin, e.g. natural clays, diatomaceous earth and synthetic minerals of silica and the like. Such extenders include kaolinites, acetapulgite 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 2.5 parts (preferably 1 to 15 parts) of wetting agent, about 0.25 to 25 parts (preferably 1, 0 to

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

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

Aqueous suspensions or emulsions can be prepared by adding. aqueous mixture of a water-insoluble active ingredient and an emulsifying agent is stirred until it is uniform, and then homogenized, so as to obtain 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 compound, the upper limit being determined by the solubility limit of the active substance in the solvent.

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

fa -> r-

an aqueous phase dispersed microcapsule phase is formed. In one embodiment, very small capsules are formed by combining an aqueous phase containing a lignosulfonate emulsifier, a water immiscible chemical, and polymethylene polyphenyl isocyanate, dispersing the water immiscible phase in the aqueous phase, and then adding a polyfunctional amine. The isocyanate and amine compounds react and form a solid urea shell around particles of the water-immiscible chemical to form microcapsules thereof. In general, the concentration of the encapsulated material is about H80 to 700 g / liter, preferably 480 to 600 g / liter of the whole preparation. , , ·

Concentrates are usually solutions of drug in non or partially water miscible solvents, along with a surfactant. Suitable solvents for the active ingredient according to the invention include dimethylformide, dimethyl sulfoxide, N-methylpyrrolidone _s hydrocarbons and water-immiscible ethers, esters or ketones. However, other strong liquid concentrates may also be prepared by dissolving the active ingredient in a solvent and then diluting, for example with kerosene, to the 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 U to 94 parts of solvent; all parts _: are by weight and based on the total weight of the emulsifiable oil. , ·

Granules are physically stable particulate compositions containing an active agent adhered to or dispersed in a matrix of inert, finely divided, particulate extender. In order to assist the leaching of the active ingredient from the particles, a surfactant such as those listed above may be present in the preparation. Natural clays, pyrophyllites, illites and vermiculites are examples of useful types of particulate mineral diluents. Preferred extenders are porous, absorptive, preformed particles, such as preformed and sieved particulate attapulgite or heat expanded particulate vermiculite, and the finely divided clays, such as kaolin clays, hydrogenated attapulgite or bentonite clays. These extenders are sprayed or mixed with the active ingredient to prepare the herbicidal granules.

The granule preparations according to the invention may contain about 0.1 to 30 parts by weight, preferably about 3 to 20 parts by weight of active ingredient per 100 parts by weight of clay and 0 to about 5 parts by weight of surfactant per 100 parts by weight of clay particles. ,

ie ^ /

O O

The preparations according to the invention may also contain other additives, e.g. Fertilizers, other ierhicides or pesticides, protective substances and the like, which are used as adjuvants or in combination with one of the adjuvants listed above. Chemicals useful for combination with the active ingredients of the present invention include:

 Triazines, ureas, carbamates, acetamides, acetanilides, uracils, acetic or phenolic derivatives, thiolcarbamates, triazoles, benzoic acids, nitriles, biphenyl ethers, and the like, such as:

Heterocyclic nitrogen / sulfur derivatives

2-Chloro-i4-ethylamino-6-isopropylamino-s-triazine 2-Chloro-4,6-bis (isopropylamino) -s-triazine 2-Chloro-4,6-bis (ethylamino) -s-triazine

3-Isopropyl-lH-2 _s l, 3-benzothiadiazine-4- (3H) -one-2,2-dioxide

3-Amino-l, 2 4-triazol _s

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

S-bromo-S-isopropyl-S-methyluracil 1,1 ¹ -dimethyl- ¹ +, H '-bipyridinium

ureas

N ¹ - (4-chlorophenoxy) -phenyl-N, N-dimethylurea N, N-dimethyl-N '- (3-chloro-U-j-butylphenyl) -urea 3- (3, U-dichlorophenyl) -l, * i -dimethylurea 1,3-Dimethy1-3- (2-benzothiazolyl) urea 3- (p-Chlorophenyl) -1,1-dimethylurea

1-butyl-3- (3,4-dichlorophenyl) -1-methyl-urea - / β <T

Carbamate / thiocarbamates ·

2-Chloroallyl diethyldithiocarbamate S-CU-chlorobenzyD-N, N-diethylthiolcarbamate Isopropyl-N- (3-chlorophenyl) -carbamate.

S-2, S-dichloroallyl-N, N-diisopropylthiolcarbamate Ethyl-N, N-dipropylthiolcarbamate S-propyldiylphenylthiolcarbamate

Acetamide / acetanilides / Aniline / amides

N, N-dimethyl-2,2-diphenylacetamide

N- (2, H-dimethyl-5- [[(trifluoromethyl) sulfonyl-amino] -phenyl) -acetamide

N-Isopropyl-2-chloroacetanilide 2 ¹ , 6'-diethyl-N-methoxymethyl-2-chloroacetanilide

2'-methyl-6 ^f -ethyl-N- (2-methoxyprop-2-yl) -2-chloroacetanilide

α, α, α-trifluoro-2S 6-dinitro-N, N-dipropyl-p-toluidine N- (1,1-dimethylpropyl-D-SjS-dichlorobenzamide

Acids / esters / alcohols

2.2, -Dichlorpropionsäure

2-methyl-U-chlorophenoxyacetic acid ·

2, U-DxChIOr ¹ PhSnOXy acetic acid methyl 2- [H- (2, H-dichlorophenoxy) -phenoxy-3-propionate 3-amino-2,5-dichlorobenzoic acid

2-methoxy-3,6-dichlorobenzoic acid ·

_ C [i - -

ί _ 2 2 8 4

2,3,6-trichlorophenylacetic acid 'N'-1-phthalylphthalic acid

Sodium 5- (2-chloro-U- (trifluoromethyl-phenoxy) -2-nitrobenzoate 4,6-dinitro-o-sec-butylphenol

N- (phosphonomethyl) glycine and sarie C ^ _-6 monoalkylamine and Alkälirnetallsalze and combinations thereof

: *. Ether 2, H-dichlorophenyl-U-nitrophenyl ether

2-chloro-a, a ₅ a-trifluoro-p-tolyl-3-ethoxy-3'-H-nitrodiphenyl ether

various

2,6-dichlorobenzonitrile

Mononatriumsäuremethanarsonat

Dinatrxuminethanarsonat

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

For herbicide formulations of the type described above, various exemplary embodiments are set forth below.

2 0 O / i / L ·. Q H § H

I. Emulsifiable concentrates

Gev7.

A. Compound of Example No.-I ^- . 50.0 Calcxumdodecylbenzolsulfonat / polyoxyethylene ether mixture

, (e.g., Atlox 3437F and Atlox 3438F) 5.0

Monochlorobenzene 45.0

• ''; 100.0

B. Compound of Example No. 12 85.0 calcium dodecylsulfonate / alkylaryl polyether alcohol mixture 4.0 C _q ^ aromatic hydrocarbon solvent 11.0 •. , 100.0

C. Compound of Example No. 13. 5.0

Calcium dodecylbenzenesulfonate / polyoxyethylene ether mixture

(e.g., Atlox 3437F) 1.0

Xylene 94.0

100.0

II. Liquid concentrates

• % by weight

A. Compound of Example No. 1 10.0

Xylene = 90.0

100.0

, Wt.%

B. Compound of Example No. 2 85.0 dimethyl sulfoxide. 15.0

•. 'οι, ο

C. Compound of Example No. 3. '< 50.0 N-methylpyrrolidone 50.0

D. Compound of Example No. 4. 5.0 ethoxylated castor oil 20.0 Rhodamii) B 0.5 dimethylformamide. 74.5

III. emulsions

A. ' Connection of. Example No. 1. UO, 0

Polyoxyethylene / block

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

Water · 56.0

B. Compound of Example No. 5 5.0

Polyoxyethylene / polyoxypropylene

Block copolymer with butanol. 3.5

Water 91.5

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

i-H-

Wt.%

B. Compound of Example No. 6 80,00 Sodium dioctylsulfosuccinate · 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 sodium N-methyl-N-oleyl taurate 1.0 kaolinite clay.''.. 86.0

100.0

.-. · ... ^v · dusts '

A. Compound of Example No. 1 2.0

Attapulgite 98.0

100.0

B. Compound of Example No. 8 60.0 Montmoril Lonit. H0,0

100.0

C. Compound of Example No. 9 · 30.0 Bentonite 70.0

100.0

D. Compound of Example "No. 11 1.0 Diatomaceous earth" 99.0

, 100.0

VI. ' Granule

A. Compound of Example No. 1 · 15.0

Granulated attapulgite (20/40 sieve) 85.0

Β; Compound of Example No. 12 '. 30.0 diatomaceous earth (20/40) 70.0

V. ιοο, ο

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

D. Compound of Example No. 14 5.0 Pyrophyllite (20/40) '95.0

VII. Microcapsules

A. Compound of Example No. 1

encapsulated polyurea fs chale 49.2

Sodium lignosulphonate (eg Reax 88 B) 0.9 water. '49,9

B. Compound of Example no. 12 encapsulated in polyurea shell _y potassium lignosulfonate (for example, Reax C-21) Water

C. Compound of Example No. 13

encapsulated in polyurea shell '80.0 magnesium salt of lignosulfate

(Treax LTM) 2.0

'Water' 18,0

· 100.0

-M-

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

The application of an effective amount of the preparations according to the invention at the site of the unwanted weeds is essential and critical for the use according to the invention. The exact amount of active substance to be used depends on various factors, e.g. the type of plant and its stage of development, the type and condition of the soil, the amount of rainfall and the specific acetanilide used. With selective pre-emergence application to plants or soil, an application rate of 0.02 to 11.2 kg / ha, preferably from about 0.04 to 5.60 kg / ha, or 1.12 to 5.6 kg / ha is usually used Acetanilide used. In some cases, larger or smaller quantities may be needed. The expert can

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

The term "soil" is used in the broadest sense of the word and includes all common soil types as defined under "soils" in Webster's New International Dictionary, Second Edition, Unabridged (1961). The term thus refers to any substance or medium in which plants can rooted and grow, and includes not only soil, but also compost, manure, dung, humus, sand, and the like, which can sustain plant growth.

End of the description

Claims (33)

He finngs a η sprueh: A herbicidal preparation characterized in that it contains an adjuvant and a herbicidally effective amount of a compound of the formula I. ClCH ₂ C CH ₂ OR (D contains, in which R is ethyl, n -propyl, isopropyl, isobutyl, sec-butyl. Cyclopropylmethyl, allyl or propargyl, R _{1 is} methyl, ethyl, n-propyl or isopropyl, and. R _{2 is} hydrogen, methyl or ethyl, with the proviso that when R "is hydrogen, R _{1 is} ethyl and R is allyl, when R "ethyl means R _{1 is} methyl and R is isopropyl when v. R is methyl, R is ethyl, iso-propyl, iso-butyl, sec-butyl or cyclopropylmethyl, if R _{1 represents} ethyl, R represents sec-butyl, allyl or propargyl, if R ₁ 'n-propyl means ^: R is ethyl and if R _{1 is} isopropyl, R is ethyl or n-propyl 2 8 4 2. Preparation according to item I _1, characterized in that the compound of formula I is 2'-methoxy-6 ¹ -methyl-N- (isopropoxymethyl) -2-chloroacetanilide. 3. Preparation according to item 1, characterized in that the compound of formula I 2 ¹ -methoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 4. Preparation according to item I _1, characterized in that the compound of formula I is 2'-methoxy-6 ¹ -methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. 5. Preparation according to item 1, characterized in that the compound of formula I is 2'-ethoxy-6'-methyl-N- (allyloxymethyl) -2-chloroacetanilide. 6. Preparation according to item 1, characterized in that the compound of formula I 2 ^1- ethoxy-ö'-methyl-N- (propargyloxyrnethyl) -2-chloroacetanilide. 7. Preparation after point. I _1, characterized in that the compound of formula I is 2'-ethoxy-6'-methyl-N-Cl-methyl) -2-chloroacetamide. 8. Preparation according to item I _1, characterized in that the compound of the formula I 2'-n. ~ Propoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 9. Preparation according to item 1, characterized in that the compound of the formula I is 2'-isopropoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 10. Preparation according to item 1, characterized in that. the ¹ compound of the formula I is 2'-isopropoxy-6'-methyl-N- (n-propoxymethyl) -2-chloroacetanilide \ -s ° - 2284 U A preparation according to item 1, characterized in that the compound of formula I is 2'-ethoxy-IM-callyloxymethyl) 2- (chloroacetanilide). 12. A preparation according to item Ί, characterized in that the compound of formula I is 2'-methoxy-6'-ethyl-N- (isopropoxymethyl) -2-chloroacetanilide. 13. A method for controlling unwanted plants in Nlutzpfflanzenkultüren / characterized in that a herbicidally effective amount of a compound of formula I is applied to the plant location. j. , 14. Method according to item 13 / characterized in that the compound of formula I is 2'-methoxy-6'-methyl-N- (isopropoxymethyl) -2-chloroacetanilide. 15. The method according to item '13, characterized in that the compound of formula I is 2'-methoxy-6'-methyl-N- (ethoxymethyl) -2-chloroacetanilide. 16. The method according to item 13, characterized in that the compound of formula I is 2'-methoxy-ö'-methyl-N- (1-methylpropoxymethyl) -2-chloroacetanilide. 17. The method of item 13, characterized in _/ that the compound of formula I is 2'-ethoxy-6'-methyl-N- (allyloxymethyl) -2-chloroacetanilide. 18. The method according to item 13, characterized in that the compound of the formula I is 2'-ethoxy-6'-methyl-N- (propargyloxymethyl) -2-chloroacetanilide. 19. Verfahrennac.h point 13, characterized by / that     · the compound of formula I 2 ⁴ -ethoxy-6 is ^J- methyl-N- (1-methylpropoxymethyl) -2-chloroacetanolide. 20. The method according to item 13, characterized in that the compound of formula I 2'-n-propoxy-6'-methyl-N- (ethoxymethyl) -2-chloracetan.i lid is. 21. The method according to item 13, characterized in that the compound of formula I 2'-isopropoxy-6'-methyl-tö -. (Ethoxymethyl) -2-chloroacetanilide. 22. The method according to 'Punkt 13 .. characterized in that the compound of the formula I is 2'-ethoxy-N ~ (allyloxymethyl) -2-chloroacetanilide. 23. The method according to item 13, characterized in that the compound of formula I is 2'-methoxy-6'-ethyl-N- (isopropoxyethyl) -2-chloroacetanilide. , 24. Method according to item 13 / characterized in that the crops are soybeans, cotton, peanuts,
Rapeseed, bush beans / sugar beet, sorghum, wheat or barley are. 25. The method according to item 24, characterized in that the unwanted plants perennial grasses and
Riedgräser and annual weeds "are. 26. Method according to item 25 _X, characterized in that the perennial weeds are Wheatgrass (Agropyrum repens) and Cyperus esculentus. 27. The method according to item 25, characterized in that the annual weeds are broadleaf weeds 28. The method according to item 27, characterized in that the broad-leaved weeds Sida spinosa, Sesbania exaltata ,. Amaranthus retroflexus, Polygonum sp.,
Chenopodium album and Datura strarninium are. 29. Method according to item 25, characterized in that the annual weeds are grasses. Method according to item 29, characterized in that the grasses are Setaria spp, Echinochloa crus-galli, Digitaria sanguinalis, Panicum spp _e , Sorghum bicolor, Brachiaria plantaginea, Oryza sativa and Rottboellia exaltata. 31 * Process according to one of the items 24 to 30, characterized in that the compound of the formula I 2 ^f -methoxy- 6 ^f -methyl-N- (isopropoxymethyl) -2-chloroacetanilide « 32. A method for the selective control of the growth of weeds in soybeans, cotton, peanuts, oilseed rape, kidney beans, sugar beet, sorghum, wheat or barley, characterized in that at the location of the weeds' a herbicidally effective amount of 2 ^t -methoxy-6 ^t -methyl-N ~ (isopropoxymethyl) -2-chloroacetanilide is applied. 33 «A method for suppression of weed stock of Ambrosiaceae, Ipomoea spp., Xanthium pensylvanicum and Abutilon theophrasti, characterized in that at the location thereof a herbicidally effective amount of 2-methoxy ~ ^{f t} 6-methyl-N- (isopropoxymethyl) ~ 2 ~ chlqracetanilide is applied «