DE1039779B - Herbicides - Google Patents

Description

GERMAN

It has been found that compounds of the general formula

Herbicides

v ^ · Χίο Ks JrLo - v ^ XN Xi ■

• X

in which X stands for hydrogen, halogen or alkyl or nitro radicals and in which the propionyl radical, if appropriate still z. B. can be substituted by halogen atoms, very good as a weed control or defoliation agent suitable.

The compounds according to the invention obtained drawings ¹ S NEN compared to the analog formyl or acetyl odef compounds which contain an acyl group with a higher number of carbon atoms, by a particularly pronounced effect of. Compared to the isobutyric acid compounds known from German Auslegeschrift 1 005 784 as weed control agents, the compounds according to the invention are distinguished by a better activity against Bellis and Phaseolus species. The allylic acid derivatives known from the same patent specification are considerably more unstable than the derivatives to be used according to the invention.

In the mustard-oat pre-emergence test, too, it was found that larger amounts of mustard are destroyed and oats were not damaged, whereas the isobutyric acid derivatives obtained from the German Auslegeschrift 1005 784 as a weed control agent are known, damage has also been observed in oats.

Finally, an advantage of the compounds according to the invention that should not be underestimated is that from German Auslegeschrift 1 005 784 known weed control agents compared to their lighter technical ones Accessibility.

Weeds in the broadest sense of this invention are intended to apply to plants which grow in places where they are are undesirable. The representatives of the above-mentioned classes of compounds are both effective in low concentrations as herbicides. It has been found that seedlings and young plants are very badly damaged or destroyed become and that ζ. B. in soil treatment, the seed germination is prevented.

Since the effect is directed in suitable concentrations, especially against dicotyledonous plants (Hederich, mustard, Cress and others), the representatives of the above-mentioned class of substances can be used for selective weed control Find. Since in higher concentrations all vegetation is destroyed and - as already above - the seed germination is prevented, these substances are also suitable as total applicants:

Farbenfabriken Bayer Aktiengesellschaft, Leverkus en-B ay erwerk

Dr. Werner Schäfer, Cologne-Stammheim,

Dr. Richard Wegler, Leverkusen,

and Dr. Ludwig Eue, Cologne-Mülheim,

have been named as inventors

herbicidal. The destruction of the weeds can be quite general at any stage of development Plants are made.

The weed remedies can also consist of a mixture of several representatives of the above-mentioned group of substances and a solid or liquid extender, the addition of known herbicides or fertilizers being possible.

Aqueous or oily dispersions, emulsions or solutions can be wetting agents, emulsifiers or others Contain dispersants. When using dust or grit, the addition of adhesives is essential necessary or at least desirable.

The compounds, a large part of which are known in the literature, are by conventional methods so z. B. from acid chlorides, anhydrides, esters, amides or other reactive acid derivatives and aromatic Amines can be produced in mostly good yields.

example

Propionic acid (p-chloro-anilide) in 0.05 ⁰ Z ₀ IgCr emulsion with the addition of acetone or dimethylformamide as a solubilizer and emulsifier destroys mustard and Hederich in mixed sowing with oats and an application rate of 1000 l / ha while largely protecting the oats .

At a concentration of 0.2 ° / ₀ mustard and oat are completely destroyed. In O, l ° / _O sodium treatment react beans with leaf shedding. When seed beds are treated with 30 kg / ha, seed germination is completely prevented.

The effect of this compound and other substituted propionic anilides is described below Table shown. For comparison, the table contains a number of other acylanilides that have the particular effectiveness illustrate the compounds used according to the invention.

809 639/473

CH ₃ - 3 formula NH- ' Cl 1 1 > —Cl cress 4th Phaseolus 3 i Obis I 0.1 Mustard oat
mixture
(Spray
at 10 cm
Height) 5 " 0 ',1 4 - test / \
\ / / \
X / Mustard oat
pre-emergence Concentration% 5 NH- / C. / \ 0.005 0.1 0 0 ( 4th 1 CH ₃ -CH ₂ - / \
\ / 0 5 0 1 NH- < Cl > -Α 3 3 1 CH ₃ -CH ₂ - C. . / 0 0 0 0 2 NH- < > —Cl 2 5 4th Cl-CH ₂ -CH- ' \ 1 to 2 2 to 3 0 3 Cl 1 3 H ₃ C-CH ₂ - NH- < 1 to 2 5 2 3 4th 3 0 V / 3 H ₃ C- CH ₂ - NH- < -Cl 3 0 5 0 0 0 Cl - Cl-CH ₂ -C- NH- / -Cl 0 0 0 6th Cl 3 0 Cl
I. NH- / -Cl Obis I 0 I.
CH ₃ -C- 0 2 7th Cl NH- / -Cl 3 0 H- 0 0 8th NH- / -Cl 0 1 CH ₃ - 0 0 9 0 - C H2 C H2 C ΧΧ2 - 0 10 2 -c - O - ( ό -c - O -c - O -C -
I. Il
O -c - O -c -
I. O -C -
i O _ Q
I. O -C - O

Explanation of symbols for the above table 2 = strongly inhibited,

65 3 = very strongly inhibited.

1st cress test: 2nd spray test:

Sprout growth inhibition as a sign of growth One to five degrees of damage to Phaseolus and

Effect of mustard and oats

0 = no effect, 0 = no effect,

1 = inhibited, 70 1 = individual light burn marks,

= significant edge burns, = severe damage, = half leaves destroyed, = whole plant destroyed.

3. '> Pre-emergenceÄ test:

One to three degrees of damage in the »pre-emergence« - Test on mustard oats

= no effect, = peak damage, = significant damage, = severe damage or not accrued.

Treated plant

Mustard and oat mixture (spray
at 8 to 10 ecm
Height)

Galeopsis tetrahit
(Fieldwood tooth)
three true pairs of leaves

Κέη centra- tion

o / / o

0.1

0.05

0.01

0.2 0.1 0.05

Propionic acid p-chloroanilide

Isobutyric acid p-chloraixilide

Degree of damage mustard oats I mustard oats

5 5 5 In the previous comparative experiments, propionic acid p-chloroanilide and isobutyric acid p-chloroanilide juxtaposed. The values shown in the table were measured here.

From these values it can be seen that the mustard-oat mixtures according to the invention in low concentrations Compounds are fully effective with mustard, whereas the oats are no longer harmed. the The corresponding isobutyric acid compound is equally effective against mustard and oats with the same ίο test arrangement. - In the field hollow tooth, the connection according to the invention is namely, propionic acid p-chloroanilide, more effective in both higher and lower concentrations than the corresponding - isobutyric acid compound.

Claims (1)

PATENT CLAIM: 4 to 3 1 Galeopsis tetrahit 5 5 3 5 5 2 4 to 4 2 Galeopsis tetrahit ^a5 3 2 2 Weedkillers based on carboxylic acid anilides, the anilide radical of which can be substituted by alkyl, halogen or the nitro group and the carboxylic acid radical of which can be substituted by halogen, characterized in that the carboxylic acid radical is a propionic acid radical. Considered publications:
German interpretative document No. 1 005 784.