DE1215437B - Weed control in onion crops - 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

1215 437
C 29016IV a / 451
January 28, 1963
April 28, 1966

The present invention relates to the use of a compound of the formula

(n) C ₄ H ₉ -O ■

NH-C-N

CH ₃

for combating undesired plant growth in crops of onion plants while protecting the latter, in which X is O or S and R is a hydrogen atom, an alkyl radical with 1 to 3 carbon atoms or the group -CH ₂ -CN.

None of the numerous herbicidally active urea derivatives described is such a selective one Known effect. The test showed that ζ. B. the N-p-ethoxyphenyl-N ', N'-dimethylurea or the N-p-methoxyphenyl-N ', N'-dimethylurea do not have the mentioned selective effect.

In U.S. Patent 2,655,447, column 3, line 64, 3- (4-isobutoxyphenyl) -l, l-dimethylurea is used described as a herbicide; it is intended to control weeds that are resistant to 2,4-D be used. This urea has the desired selectivity of the ureas mentioned above Formula does not open, d. that is, it damages both weeds and bulbous plants.

It is particularly surprising and particularly valuable that the active ingredients of the above general formula killing not only dicots, but also monocot undesirable plants under Protection of the onion plants, which are monocotyledons themselves. Is of the greatest value also that the application of the remedy regardless of the stage of development of the onions can be done.

The active ingredient can be used in the form of dusts, in emulsified, dispersed or dissolved form will. A very suitable form of application is also the combination with m-chlorophenyl isopropyl carbamate.

For the production of directly sprayable solutions come z. B. mineral oil fractions of high to medium boiling range, such as diesel oil or kerosene, also coal tar oils or vegetable oils or of animal origin as well as hydrocarbons such as alkylated naphthalenes, tetrahydronaphthalene, into consideration, optionally using xylene mixtures, cyclohexanols, ketones, furthermore Weed control in onion crops

Applicant:

CIBA Aktiengesellschaft, Basel (Switzerland)

Representative:

Dr.-Ing. Dr. jur. F. Redies,

Dr. rer. nat. B. Redies, Dr. rer. nat. D. Turk

and Dipl.-Ing. Ch. Gille, patent attorneys,

Opladen, Rennbaumstr. 27

Named as inventor:

Dr. Henry Martin, Basel;

Dr. Ludwig Ebner, Stein, Aargau (Switzerland)

Claimed priority:

Switzerland of January 29, 1962 (1055)

chlorinated hydrocarbons such as tetrachloroethane, trichlorethylene or trichlorobenzene.

Aqueous application forms are made from emulsion concentrates, Pastes or wettable powders are prepared by adding water. Quaternary emulsifiers or dispersants are used Ammonium compounds, soap, soft soap, aliphatic sulfuric acid ester salts, aliphatic-aromatic Sulphonic acid salts, alkoxyacetic acids, polyglycol ethers of fatty alcohols and polyethylene oxide condensation products called.

For the production of dusts, talc, kaolin, bentonite, calcium carbonate, Calcium phosphate, but also coal, cork flour and wood flour and other vegetable materials Origin are used. The various forms of use can be used in the usual way by adding substances that improve distribution, adhesive strength, rain resistance or the Improve penetration, be provided; as such substances are mentioned: fatty acids, resins, Glue, casein or ζ. B. also alginates. The preparation can also be used as granules.

Under "weeds" are also undesired, z. B. at an earlier point in time on the to be treated Understand cultivated crops on the ground,

609 560/465

The following are some of the compounds encompassed by the above general formula: their production by methods known per se, for. B. by implementing the appropriate Amine can be carried out with the corresponding isocyanate or isothiocyanate:

(n) C ₄ H ₉ O-

-NH-C-N ((A)

II ^X CH3
O

(Melting point: recrystallized from acetonitrile, 118 to 119 ⁰ C)

(n) C ₄ H ₉ O-

-NH-C-N

Il ο

/ CH ₃
CH ₃

(B)

(Melting point: recrystallized from acetonitrile to 116 to 117.5 ⁰ C)

(n) C ₄ H ₉ O

.. / CH _3. (C)

(Melting point: recrystallized from acetonitrile, 109 to 110 ^° C.) · '■ ■ ^! "

(n) C ₄ H ₉ -O-

-NH-C-N

\ _f

^ CH ₃
^ CH ₃

b) Wettable powders of the following composition were produced, each containing 20% one of the active ingredients described above under (A) to (E):

50% Bolus alba (kaolin),

25% finely divided SiO ₂ [product sold under the brand name »HISIL«],

9.5% of a condensation product of 1 mole of dodecyl mercaptan with 12 moles Ethylene oxide,

1.5% of a condensation product of p-nonylphenol with 9 moles of ethylene oxide.

The finely ground mixture obtained in this way can be made into a ready-to-use mixture with water in any desired manner Dilute the spray liquid.

Example 2

In the greenhouse, clay pots were filled with earth and sown with seeds of the following types of plants; Allium cepa, Medicago sativa, Lactuca sativa, Spinacia oleracea, Linum usitatissimum, Cucumis sativum, Beta vulgaris, Sinapis alba, Alopecurus myosuroides and Poa trivialis.

10 days after sowing, i.e. H. in the cotyledon stage of. named plants, these were with a Dispersion according to Example 1, containing the compound described above under (B), accordingly Treated application rates of 6 kg of active ingredient per hectare.

During the evaluation, 18 days after the treatment, the effect on the individual plant : Species with values from 0 to 10 (0 = no effect, 10 = completely killed) were found.

The result is shown in the following table:

-Table 1

^S CH ₃
O (D)

(Melting point: recrystallized from acetonitrile, 107-108 ⁰ Q

jK / CH ₃

(n) C ₄ H ₉ -O <> -NH-CN (

^^ Il> CH ₃

(E)

(Melting point: recrystallized from acetonitrile, 112 to 114 ° C)

B e i s ρ i e 1 1

a) Wettable powders were prepared, each containing 50 parts of one of the above under (A) to (E) Contained active ingredients, 45 parts of kaolin and 5 parts of lignin sulfonic acid.

Instead of kaolin, another filler can be used, z. B. talc or chalk can be used; Instead of lignin sulfonic acid, another one can be used Dispersants, e.g. B. an alkylarylsulfonate or a nonionic dispersant or their Mixture can be used. The wettable powder obtained in this way can be mixed with water in any desired manner a finely divided dispersion.

Test plant

Allium

Medicago.
Lactuca ..,
Spinacia ..,
Linum
Cucumis ..
Beta .....
Sinapis
Alopecurus
Poa

Active ingredient in kg / ha
6.0

οίο

10
10
9
10
10
10

The active ingredient described above under (B) therefore does not impair the growth of Allium cepa while having a good effect on the other plants listed.

Example 3

The dependency of the tolerance of the active ingredient described above under (B) for onions became and the weed effect of soil type and time of application are checked.

Soil types: a with 1.5% humus,
b with 6.3% humus,
c with 12.7% humus.

The treatments were carried out:

1. On the day of the sowing of Allium and Sinapis.

2. 4 days after the sowing of Allium and Sinapis.

3. 10 days after sowing (Allium in the iron stage, Sinapis in the second leaf stage).

A spray mixture prepared according to Example 1, a) was used, which has the above under (B) contained the active ingredient described.

The application rates of the active ingredient corresponded to 2.5 and 5.0 kg / ha.

Table 2

The result is shown in the following table (0- = no effect; 10 = completely killed). - .; =

Test plants Allium cepa 5.0 2.5 5.0 Earth types and Sinapis alba Application rate 9 0 0 Application 10 0 0 time Kilograms of active ingredient per hectare 10 0 0 2.5 10 0 0 l, a 5 10 0 0 2, a 10 2 B 10 2, c 10 3, c 10

20th

For treatments before weeds and onions emerge, 2.5 to 5.0 kg of active ingredient are required necessary to achieve a good weed effect. Shortly after the weeds and germination Even before the onions emerge (2, a, b, c), 2.5 kg of active ingredient per hectare are sufficient for a good Weed effect, with even 5.0 kg of active ingredient per hectare from the onions without damage will.

In the ironing stage of the onions in humus-rich soil (3, c), both 2.5 kg 'of active ingredient per Hectares as well as 5.0 kg of active ingredient per hectare endured by the onion plants without damage, whereby the other plants listed above are completely killed.

45

Example 4

Clay pots were filled with earth and sown with the following types of plants: Allium cepa, Poa nemoralis, Beta vulgaris, Lactuca sativa and Medicago sativa.

Pre-emergent treatment

Two days after the sowing, the surface of the earth became in the clay pots which the above mentioned Contained plant seeds, with a spray mixture according to Example 1, b), containing the above under (A) described active ingredient, treated according to an application rate of 6.0 kg / ha. The evaluation occurred 18 days after treatment.

Post-emergent treatment

60

10 days after sowing, i.e. H. at the cotyledon stage, the above plants were placed in the clay pots with a spray liquor according to Example 1, b), containing the active ingredient described above under (A), treated according to an application rate of 6.0 kg / ha.

The evaluation was carried out 18 days after the treatment.

Allium

post-

Poa

pre-

post-

beta

pre-

post-

9 10 8 10 10 10

Lactucä

pre-

post-

Medicago

pre-

Example 5 '

Clay pots were filled with earth and sown with the following types of plants: Allium cepa, Poa nemoralis, Beta vulgaris and Medicago sativa.

The surface of the earth in the clay pots was made according to the im. Example 4 according to the manner described treated the pre-emergent process with a spray liquor according to Example 1, b), which as an active ingredient contained the compound described above under (D), the application rate of active ingredient 6.0 kg / ha corresponded. The result is shown in the following table:

Allium Poa beta Medicago 0 9 5 9

Example 6 _O

Clay pots were filled with earth and marked with 'follow- ^ sown the plant species: Allium cepa, Beta vulgaris, Lactuca sativa, Medicago sativa.

The plants in the clay pots were in the manner described in Example 4 by the post-emergent method treated, the application rate of active ingredient corresponding to 2.0 kg / ha.

The result is shown in the following table:

Allium beta Lactuca Medicago 2 8th 10 10

Similar good selective effects as in Examples 2 to 6 were achieved if one under the conditions described there spray mixtures according to Example 1, b) used, which as active ingredient contained the compounds described above under (C) or (E).

Example 7

a) A field culture of onions was cultivated 3 weeks after the onions were sown with a Spray liquor according to Example 1, a), containing the compound described above under (B) treated. the The application rates were 2.0, 3.0, 4.0 kg of active ingredient per hectare. The onions were in time treatment in the ironing to whipping stage. The weeds had second to third leaves developed.

The three existing weed species Amaranthus retoflexus, Chenopodium album and Mercurialis annua were completely controlled with each of the application rates mentioned, the onions were not harmed by the treatment.

b) A field culture of onions was cultivated 20 days after the onions were sown with a Spray liquor according to Example 1, a), containing the compound described above under (A) in one application rate of 2.0, 3.0, 3.5 and 4.0 kg of active ingredient each

Hectares, treated. The onions were in the whip stage at the time of treatment, the Weeds in the first leaf leaf stage. With each of the application rates mentioned, a complete Weed killing achieved with no harm to the onions.

The existing weeds were completely destroyed by the treatment, namely Sinapis arvensis, Fumaria officinalis, Senecio vulgaris, Sonchus arvensis, Mätricaria inodora, Polygonum sp., - Chenopodium album, Chenopodium rubrum, Mercurialis annüa, Stellaria media.

Example8

I. There were wettable powders in Example 1 under b) specified composition prepared, which as active ingredients in each case one of the following compounds contained·:

1. Connection (A),

2. connection (B),

3. Compound (C),

4. connection (D),
. 5. connection (E),

6. 3 - (4 - Isobutylphenyl) -1,1 - dimethylurea according to U.S. Patent 2,655,447.

II. It was dfe selective effectiveness of spray mixtures, which from those described under I above Wettable powders had been produced in the control of monocotyledonous and dicotyledonous test plants in the presence of onion plants compared. The test was carried out in the manner indicated in Example 2 of the invention. The application rate each corresponded to 4 kg / ha. When evaluated 18 days after the treatment, it became the following Result listed in the table (the numerical values have the following meaning: 0 = none Effect; 10 = plant completely killed; Values above 5 mean that the plant is so badly damaged is that she can no longer recover).

Test plant

Allium (onion)

Medicago sativa

Lactuca sativa

Sinapis alba

Alopecurus pratensis.
Poa trivialis

Effect of the spray liquid 12 3 4 5 6

10

10

10

10 10

2 9

10 9 9

10

The above results show that only in the case of the agents according to the invention (spray liquors 1 to 5) control of the test plants also tested is possible without damaging the bulbous plants. In the case of the known agents according to US Pat. No. 2,655,447 (Spray Mixture No. 6) the onion plants were almost as badly damaged as the test plants that were also tested.

Claims (1)

Claim: Use of a compound of the formula for combating undesired plant growth in crops of onion plants while protecting the latter, in which X is O or S and R is a hydrogen atom, an alkyl radical with 1 to 3 carbon atoms or the group -CH ₂ -CN. References considered: U.S. Patent No. 2,655,447. 609 560/465 4.66 © Bundesdruckerei Berlin