DE2257034A1 - HERBICIDE - Google Patents

Description

and

Hydrogen, alkyl radical with 1-3 carbon atoms or -OCH,

Hydrogen or alkyl radical with 1-3 carbon atoms

Hydrogen or methyl radical

Hydrogen, halogen, alkyl radicals with 1-3 carbon atoms or -OCH-, and of the E ^, R ₁ -I Eg and Er _{7 groups are} at least 3 hydrogen radicals each and only one represents another radical «

409822/1118

Preferably is

R ₁ »hydrogen, methyl or -OCH,

Ep - hydrogen, methyl

R., Hydrogen, Methyl

R _{/ +} , R ₁ -, R ₆ , hydrogen, chlorine, methyl or -OCH,

The compound class of coumarilic acid amides is known from the prior art, but it is new that one
certain group of these ¹ substances has herbicidal effects. The compounds act in particular in the post-emergence phase, showing partly selective and partly total herbicidal action.

The production of the CuDiarilsäui-eamide happens in itself in a known manner by reacting the corresponding coumaric acid chlorides with .Ammoniak or primary or secondary amines, possibly with the addition of one with water not miscible inert solvents such as benzene, diethyl ether or chloroform.

The active ingredients can be formulated into emulsion concentrates, wettable powders or dusting agents by customary methods will.

Emulsion concentrates contain about
10 - 50% by weight of active ingredients

25 - 80 wt% organic solvent, for example.

Benzene, toluene, xylene, cyclohexanone, iso-propanol, butanol, glycol ether, Ethoxymethanol, butoxyethanol and

5-15% by weight of dispersing agents, such as.

Sodium alkylbenzenesulfonate, calcium dodecylbenzenesulfonate, Alkyl polyglycol ethers, alkyl phenol ethylene oxide

409822/1118 - 3 -

Densation products and sodium alkylnaphthalene sulfates.

They are made by intimately mixing the ingredients in one Manufactured stirred tank.

In general, wettable powders contain

30 -. 80% by weight of active compound

some .. wt% Dispergierhilfsaiittel and optionally

Ί0 - 60 wt% inert ingredients, such as kaolin, · Eont-.

morillonite, china clay, magnesium carbonate, Calcium carbonate, kieselguhr, highly dispersed silica.

The dusts mostly consist of 5-25% by weight of active ingredient as well

Inert components, whereby the same can be used as with wettable powders.

In these powder formulations, the active ingredient is intimately mixed with the other substances, then by one Hammer mill or other suitable grinding device grind to a grain fineness of mostly below 20 / u, mixed again and finally cleaned through a sieve.

In addition to the active ingredients according to the invention, known active ingredients, such as from the class of ureas, aryloxy fatty acids, triazines, carbamates and thiol carbamates, the dinitroalkylanilines, the acylanilides and the dinitrophenols are combined.

In this way, effects can be increased or even better Culture compatibility can be achieved.

409822/1118

Example 1 (manufacture)

The compounds listed in the table below are prepared analogously to the following general preparation procedure Insofar as no literature is listed above in Table 1 the compounds mentioned are described for the first time.

The corresponding substituted coumaryl chloride is dissolved in 10 times the amount of benzene. For this purpose, v / ground with stirring at 30-50 ^° C. per. mol of acid chloride used 2.1 mol of ammonia or the correspondingly substituted amine or aqueous solutions thereof (in the case of reactions with ammonia, methylamine and dimethylamine) are added. After the addition has ended, the mixture is stirred at JQ ⁰ G for a further half an hour. Subsequently, water, 2 η HCl and twice with saturated sodium bicarbonate solution are extracted one after the other with 1/10 part by volume, based on the volume of the benzene solution.

After drying over anhydrous sodium sulfate and evaporation of the solvent in a water jet vacuum, the corresponding coumaril gmireanide is obtained in 95-97% purity (80-90 % yield) from the benzene solution.

In the case of the compounds that were obtained as oily liquids, the position of the proton resonance signal of the C hydrogen atoms of the substituent esa »nitrogen atom is used for characterization instead of the melting point. The S values for ßubst, No. 2 are 2.92 ppm and for substances No. 9 and 14- are 5 »^ 2

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409822/1118

Example 2 emulsion concentrate

Active ingredient ■ 10 - 50%

Cyclohexanone 20 - 60%

Xylene 5 - 20%

Emulsifier IPIS * 5-15 %

Mixture of sodium alkyl benzene sulfonate, alkyl polyglycol ether and solvents - trade name of the chemical works

Example 3 wettable powder

Active ingredient

Sodium sulfobernst one acid edi oc tyl ester

Sodium lig / iinsulfonate

highly dispersed
Silica

kaolin

Example 4

Active ingredient 5-25

highly disporsc

Silicic acid 0 - 1

Calcium carbonate 70-95

Example 5

The test for herbicidal properties was carried out as follows by * - guided:

The following plants were sown in planters in the greenhouse

Zea-Mays (maize), Hordeum (barley), Digitaria (blood millet), Avena fatua (wild oats), Sinapis (mustard), Centaurea (cornflower), GaIi a aparine (sticky herb), beta (sugar beet).

Jm,:, - :: Ä / 0: .- 9 8 2 2/1 118

30 - % 2 - % 0 - % 0 - 90 10 - cL - 80 dust - 3 ■ 4 - 3 - 60

14 days after emergence the plants were with 6 kn; / iio Active ingredient ^ which is called 'fhulcionskonsentrat as folfrt f o.r-r: ul: i ert vai ·, treated.

Active ingredient 20% Cy c 1 ohciX 3Jicn 50 % Xylene
■ λ. 20 % Emulsifier JHS 10 % I ^ aulgator ^ emiscl ι from Hatriunalkylbenvoolcullonat, All: ylj) oly- fcv'l-yko 1 ether and Solvent.

Rated vrarde the »last time 20 days after the spraying., The Results can be seen from Table 2.

Table 2

bdg. Mail · "Gers'cs * millet ^l? Lug- mustard turnip 'grain Klebkrsut

oat flower

1 3 2 3 3 - 2 4th 5 5 1 6th 1 7th 10 8th 10 9 10 12th 6th 13th 8th 14th 10 Key may be:

3 9 8 2 9 1 7 9 6

6 9 7 2 3 2

2 4 5

7 7 8

4 5 5

7 5 7 111 2 2 1

8 6 8

0 - no effectiveness 10 = plants completely destroyed

9 9 3 10 7th 7th 8th 10- 9 6th 5 7th 8th 8th 6th 8th 7th 9 1 1 3 4th 10 9

3 4th 2 3 1 4th 2 4 · 3 3 2 2 7th 9 0 3 2 7th 0 . 1 0 0 3 8th

409822/1118 " ⁸

As Table 2 shows, compounds 1 and 5 control grass weeds in maize largely without damaging the crops.

In contrast, preparations 9 and 14 herbicides are not used will be found in ornamental crops that belong to the sunflower family.

409 822/1 1 18

Claims (1)

Patent application Herbicides, characterized by a content of one or several gumarilic acid amides of the general formula Rr whereby Hydrogen? -, alkyl radical with 1-3 carbon atoms or -OCH-. 3 Hydrogen or alkyl radical with 1-3 carbon atoms Hydrogen or methyl radical Rc, hydrogen, halogen, alkyl radical with 1-3 Carbon atoms or -OCH-, mean and of the Residues R ^ ,, Rc, R ^ - and R "at least 3 hydrogen x ^ estes each and only one represents another remainder. 409822/1