DE1216010B - Selective herbicide - Google Patents

Description

FEDERAL REPUBLIC OF GERMANY

GERMAN

PATENT OFFICE

EDITORIAL

Int. Cl .:

Number:
File number:
Registration date:
Display day:

AOIn

German class: 451-19 / 02

1216 010
B 74860IV a / 451
December 31, 1963
May 5th 1966

It is known compounds of the formula

Selective herbicide

in which R is a phenylpest, X is a possibly through a chloroacetyl or ^, ^, ^ - trichlorohydroxyethyl radical substituted amino group or a dimethylformamidine group and Y is halogen, for Use to combat unwanted vegetation. They have the disadvantage that their effect occurs slowly, especially in dry climates.

It has been found that these disadvantages do not occur with means in addition to the above Compounds additionally a compound of the formula

: c = o

contain, in which R is an alkyl radical containing 1 to 2 carbon atoms and R 'is an aliphatic radical with 3 to Means 4 carbon atoms.

Such compounds are, for example: 1-methylpyrrolidone- (5), l-methylpiperidone- (6), 1-ethylpiperidone- (6) and 1,2-dimethylpyrrolidone- (5).

After their application, the agents according to the invention develop a herbicidal effect which occurs quickly, even if there is no rain for a long time. They are applied, for example, in such a way that from the Pyridazon with the lactam a solution is prepared, optionally the usual emulsifiers can be added. This solution, when poured into a large amount of water, gives a dispersion which is sprayed onto the plants as an aqueous spray mixture.

The agents according to the invention can also contain other herbicidal active ingredients, for example α, α-dichloropropionic acid-zS-chloroethyl ester ,, 2 ', 3-dichloroallyl

Applicant:

Aniline & Soda Factory in Baden

Aktiengesellschaft, Ludwigshafen / Rhein

Named as inventor:

Dr. Adolf Fischer, mother city;

Dr. Gotthard Synnatschke,

Dr. Franz Reicheneder, Ludwigshafen / Rhine;

Dr. Karl Dury f, Kirchheimbolanden;

Dr. Günter Scheuerer, Ludwigshafen / Rhine

NjN-diisopropylthiolcarbamate, phenylcarbamic acid isopropylejsr, are added,

The following examples show the superiority of the agents according to the invention over known ones Means.

example 1

In the greenhouse, beets (Beta vulgaris), white goosefoot (.Chenopodium album), chamomile (Matricaria chamomilla), stickwort (Galium aparine), wild oats (Avena fatua), black foxtail (Älopecurus myosuroides), mustard (Sinapis alba), small nettle (Urtica urens), knotweed species (PoIygonum sp.), French wort (Galinsoga parviflora) and sorrel (Rumex acetosa) at an average height of plants from 5 to 7 cm with two different means (I) and (II) each in one Application rate corresponding to the use of 2.4 kg of active ingredient per hectare dispersed in 600 l of water sprayed per hectare. The plants are kept relatively dry during the duration of the experiment. 14 days after the treatment it is found that the means II almost all weeds better and faster fights as means I. The beets (Beta vulgaris) are only slightly damaged by means II. This does not affect the weight of the sugar beets harvested from these plants.

609 567/511

The table below shows the degree of damage to the plants in percent:

The table below shows the degree of damage to the plants in percent:

Useful plant
Beta vulgaris

Unwanted plants
Chenopodium album ...
Matricaria hemomilla.

Galium aparine

Avenä fatüa

Alopecurus myosuroides

Sinapis alba

Urtica urens

Polygonum sp

GaÜnsoga parviflora ...
Rumex acetosa ....

0 = without damage.
100 = total damage.

middle

45

30 to 40 30 to 40

20 20 to 30

50

45

40

40

30th

10

90 to 100 90 to 100

95

30 to 40 40 to 50

100

95 to 100 90 to 100 90 to 100 90 to 100 crop
Beta vulgaris

Unwanted plants

Chenopodium album

Matricaria chämomilla ...

Galium aparine

Avena fatua

Alopecurus myosuroides ..

Sinapis alba

Urtica urens

Polygonum sp

GaÜnsoga parviflora

Senecio vulgaris

0 = without damage.
100 = total damage.

middle

II

40

40 30 to 40

20th

30th

55

50

40

45 30 to 40

10 to 15

95 to 100 90 to 100 90 to 100 50 to 60

60 100

95 to 100 90 to 100 90 to 100

90

Composition of funds
(Data in percent by weight)

I: 80% l-phenyl-4-amino-5-chloropyridazon- (6), 2% sperm oil alcohol sulfonate, 8% lignin sulfonate,
10% kaolin.

II: 20% l-phenyl-4-amino-5-chloropyridazon- (6), 20% polyglycol,
10% castor oil polyglycol ether, 50% l-methylpyrrolidone- (5).

The same effect as the means II have means that, with otherwise the same composition, instead of. 50 percent by weight of l-methylpyrrolidone- (5) the same amount of l-ethylgyrrolidone- (5) or 1-methylpiperidone- (6) or l-ethylpiperidone- (6) contain.

25 Composition of funds:
(Data in percent by weight)

I: 80% l-phenyl-4-amino-5-chloropyridazon- (6), 2% sperm oil alcohol sulfonate, 8% lignin sulfonate,
10% kaolin.

35

40

Example 2

In the greenhouse, beets (Beta vulgaris), white goosefoot (Chenopodium album), chamomile (Matricaria chamomÜla), sticky herb (Galium aparine), wild oats (Avena fatua), small nettles (Urtica urens), knotweed species (Polygonum sp.), French herb (GaHnsoga parviflora) and ragwort (Senecio vulgaris) with an average height of the plants of 5 to 7 cm with two different agents (T) and (JI) each at an application rate corresponding to the use of 2.4 kg of active ingredient per hectare dispersed in 6001 Water sprayed per hectare. The plants are kept relatively dry during the duration of the experiment. 14 days after the treatment, it is found that means II combats almost all weeds better and faster than means I. Slight damage to beets caused by means II has grown out again after about 2 weeks. This does not affect the weight of the sugar beets harvested from these plants.

Active ingredient.

Π: 10% l-phenyl- ^ amino-S-chloro-

pyridazon- (6)
10% α, α-dichloropropionic acid

/ 3-chloroethyl ester
15% sodium salt of sulfosuccinic acid-bis-

(2-ethylhexyl) ester,
15% xylene,
50% 1-methylpyrrolidone- (5).

45 The different surface-active agents used in Examples 1 and 2 for agents I and II Substances do not cause differences in the biological effects of these agents.

Biologically just as effective as the agents I and II in Examples 1 and 2 are the corresponding Agents that replace l-phenyl ^ -amino-S-chlorpyridazon- (6) contain any of the following compounds:

1-phenyl-4 - («- hydroxy - ^ ', | S', / S-trichloroethyl) -

amino-5-bromyridazon- (6), l-phenyl-4 - («- hydroxy- _i 5 ', / 3', | 8-trichloroethyl) -

amino-5-chloropyridazon- (6), l-phenyl- ^ chloroacetylamino-S-bromo-

pyridazon- (6),
N- [4- (l-phenyl-5-bromopyridazon-6) -yl] -N'-dimethylformamidine,

l-phenyl-4-amino-5-bromopyridazon- (6), l-phenyl-4-amino-5-iodopyridazon- (6), 1-phenyl-4-amino-5-fluoropyridazone- (6).

Claims (1)

5 6 Claim: amino group or substituted hydroxyethyl radical Selective herbicide that is a compound of a DimethyhOrmamidine group and Y halogen Formula means, contains, characterized by X net that there is also a connection to the 5 formula R ' "^ C = O N contains, in which R contains 1 to 2 carbon atoms in which, R contains a phenyl radical, X optionally an alkyl radical and R 'an aliphatic radical by a chloroacetyl or β, β, β-ΊήοΙΑοτ- 3 to 4 carbon atoms. 609 567/511 4.66 © Bundesdruckerei Berlin