DE2039041A1 - Herbicides - Google Patents

Description

Conventional weed control agents, e.g. triazine, urea or Phenoxy fatty acid derivatives, in a number of agricultural crops, have had good results in controlling broad- " leaved weeds delivered. However, difficulties arise from the control of weed grasses, e.g. Avena fatua (flying oats) and Alopecurus myosuroides (black foxtail), which have spread unusually in recent years due to the increase in cereal crops and a reduction in root crop cultivation have found.

The control of these and other weeds in cereals, i.e. cultivated grasses, has been difficult up to now. There are herbicides such as triallate or 2-chloro-3- (4t-chlorophenyl) methyl propionate, the effective as post-emergence or pre-emergence agent, especially against wild oats are without substantially damaging wheat or barley, but these remedies are ineffective against broad-leaved weeds.

The present invention relates to herbicidal compositions for selective Control of weeds (grass weeds) in cereals, also in cotton, peanuts and legumes. They contain as active Substance the known compounds N-4-isopropylphenyl-N'-methyl-urea (USP 2,655,447) and N-4-isopropylphenyl-N ', N'-dimethyl urea (Bio. Chira Biophys. Acta 66 (1963) 78-85;) of the formulas:

./2

209 808/1964

ORIGINAL INSPECTED

-NH-C-NH-

Il

and

These agents are characterized by their gentle properties on a number of crops, especially cereals such as wheat, barley, maize, rice, also cotton, peanuts, legumes such as soybeans or French beans.

The compounds according to the invention have the advantage over other known agents for the selective control of grass weeds at the same time to show a good effect against a number of broad-leaved weeds.

It is surprising that the present compositions with the above active ingredients at application rates which include cereals such as wheat, barley, Rice and maize no longer damage or only slightly damage them, nor a practically complete destruction of the undesired ones Cause weeds. According to the above-mentioned patent specification and literature reference, this was not to be expected.

The agents according to the invention can be used as wettable powders, emulsifiable Concentrates, sprayable solutions, dusts or granules are used. Wettable powders are in water uniformly dispersible preparations which, in addition to the active ingredient, besides a diluent or inert substance, also wetting agents, e.g. polyoxyethylene alkyl phenols, polyoxyethylene oleyl or

209808/19 6 4

Stearylamines, alkyl or alkylphenyl sulfonates and dispersants e.g. sodium lignin sulfonic acid, 2,2'-dinaphthylmethane-6, 6'-disulfonic acid sodium, dibutylnaphthalenesulfonic acid sodium or contain sodium oleylmethyltaurate.

Emulsifiable concentrates are made by dissolving the active ingredient obtained in an organic solvent, e.g. butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics. In order to achieve good suspensions or emulsions in water, wetting agents from the series mentioned above are also added.

Dusts are obtained by grinding the active ingredients with nan * finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophyllite or diatomaceous earth. Sprayable solutions, as they are often traded in spray cans, contain the active ingredient dissolved in an organic solvent, alongside a mixture of chlorofluorocarbons, for example, as a fuel.

Granules can be prepared either by spraying the active compound onto adsorptive, granulated inert material or be by applying active compound concentrates by means of adhesives, for example polyvinyl alcohol, sodium polyacrylate or else mineral oils on the surface of carriers such as sand, kaolinites or granulated inert material λ. Suitable active ingredients can also be produced in the manner customary for the production of fertilizer granules - if desired, in a mixture with fertilizers.

In the case of herbicidal agents, the concentrations of the active ingredients in the commercially available formulations can be different. In wettable powders, the active ingredient concentration varies, for example, between about 10 % and 95%, the remainder being made up of the formulation additives given above. In the case of emulsifiable concentrates, the active ingredient concentration is around 10% to 80%. Dust-like formulations usually contain 5 - 20% active ingredient, ver -n.

2098Ό8 / 196Α

ORIGINAL INSPECTED

sprayable solutions about 2 - 20%. In the case of granules, it hangs Active ingredient content partly depends on whether the active compound is liquid or solid and which granulation aids, Fillers, etc. can be used.

The commercially available concentrates are optionally used for use diluted in the usual way, 25.B. with wettable powders and emulsifiable concentrates using water. Dusty and Granulated preparations and sprayable solutions are no longer diluted with other inert substances before use. The required application rate varies with the external conditions such as temperature, humidity, etc. It amounts to in generally about 0.015-0.25 g / m², preferably about 0.03 to 0.12 g of active ingredient per m².

In addition, the active compounds according to the invention can be used with others Herbicides and soil insecticides are combined.

Known herbicides that are suitable for a combination with the claimed new products include, for example:

Urea derivatives linuron, chloroxuron, monolinuron,

Fluometuron, diuron;

Triazine derivatives Simazine, Atrazine, Ametryn, Prometryn,

Desmetryn, Methoprotryn;

Urazil derivatives lenacil, bromacil;

Pyrazone derivatives l-phenyl-4-amino-5-chloropyrazidone- (6); Growth substance preparations 2,4-dichloro-phenoxy-acetic acid,

4-chloro-2-methylphenoxy-acetic acid, 2,4,5-trichlorophenoxy-acetic acid, 4-chloro-2-methyl-phenoxy-butyric acid, 2,3,6-trichlorobenzoic acid;

Carbamic acid derivatives Barban, Phenmedipham, Triallat,

Dialate, vernolate and 2-chlorallyl-Ν, Ν-diethyldithiocarbamate, Swep;

Dinitrophenol derivatives Dinitro-o-cresol, Dinitro-sec.

butylphenol or dinoseb, dinoseb acetate;

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Chlorinated aliphatic

Acids sodium trichloroacetate;

Amide diphenamide, N, N-diallyl chloro

acetamide;

Dipyridilium compounds Paraquat, Diquat, Morfamquat;

Anilide N-CS ^ -Dichlorpheny ^ -methacryl-amid,

Propanil, Solan, Monalide, 2-chloro-2 ', 6'-diethy1-N- (methoxymethyl) -acetanilide, Propachlor;

Nitriles dichlobenil, ioxynil; ·

other preparations flurenol, 3,4-dichloropropionanilide,

Trifluralin, bensulide, 4-trifluoromethyl-2,4'-dinitrodiphenyl ether, Monosodium methyl arsonate.

There is another form of application of the present active ingredients in their mixture with fertilizers, whereby fertilizing and herbicidal agents are obtained at the same time.

The claimed agents have a very good effect on weed grasses that are difficult to control and, as already mentioned above, are gentle on a number of important crops such as wheat, barley, maize, rice, as well as cotton, peanuts, legumes and cabbage, known herbicides, for example fluometuron, monuron, diuron, terbutryn and a triallate, superior.

example 1

A wettable powder which is easily dispersible in water is obtained, by

25 parts by weight of N-4-isopropylphenyl-N'-methylurea as

Active ingredient.

64 parts by weight of kaolin-containing quartz as an inert substance 10 parts by weight of potassium lignosulfonate and 1 part by weight of sodium oleylmethyltaurate as wetting agent

and dispersants

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mixes and grinds in a pin mill.

Example 2

A dust that is used as a herbicide well suited, is obtained by one

10 parts by weight of N ~ 4-isopropylphenyl-N ', N ^l -dimethyl urine-

substance as active ingredient and 90 parts by weight of talura as Iiiertstoff

mixed and crushed in a hammer mill.

Example 3

An emulsifiable concentrate consists of

15 parts by weight of N-4-isopropyl-phenyl-N'-methyl-urea 75 parts by weight of cyclohexanone as a solvent and 10 parts by weight of nonylphenol (10 AeO) as an emulsifier.

Example 4 Pre-emergence procedure

Seeds from various weeds or crops were each in pots - i.e. each species for itself - which were filled with clay, sown and covered with a layer of soil about 1 cm thick covered.

On the day of sowing, aqueous suspensions of a wettable powder of the various preparations suspended in water were made sprayed onto the soil surface according to Example 1. The concentrations result from Table I. The following products are involved:

- // \ -NH-CN

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: cH

! - If \ -NH-C-

NH-C-Nt

CH,

Suspensions of the following substances prepared in an analogous manner were used as comparison agents:

-NH-C-N

■ ι

CH ₃

CH,

Monuron

Vnh-c-n:

egg

.CH,

Diuron

NS,

Terbutryn

CH,

CH,

: cH

-NCS-CH ₂ -CCl-CCl ₂ triallate

Triallate was used as an aqueous emulsion with the top layer of soil mixed·

The pots were then placed in a greenhouse. After 4 days the effects of the remedies on the weeds became apparent

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and cultivated plants, expressed as the degree of damage in percent, determined; i.e. lOO - complete destruction of the plants, O - no harm. Details can be found in Table I.

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Table I Action against weeds and crop plants in the preemergence method; Dosage in g active substance per qxn soil surface.

according to the invention 0.03 B. 0.015 0.03 C. 0.015, 0.03 Comparison means 0.015 0.03 E. 0.015 0.03 F. 0.03 I.
CO 10 203 Plant type preparation A. D. 0.015 dosage 0.015 100 89 95 80 90 20th 65 20th 40 100 0 Weeds (grasses) 100 95 100 75 80 90 100 80 100 95 70 10 Avena fätua 100 100 95 100 95 100 85 100 100 100 40 75 ** Alopecurus myosuroides 100 100 100 100 100 ' 100 100 100 90 100 50 . 30th 0 coApera spicae-venti 100 20th _o Poa annua 100 95 75 90 95 100 90 100 90 100 Ot 0 ^ Broad-leaved weeds 85 *** Mixture of the below * ■ * th species 30th 0 1.0 60 70 45 90 15th 25th Cultivated plants: * Triticum aestivium 10 20th 0 10 35 65 40 80 10 20th (Wheat) Hordeum distichum 0 (Barley)

The figures in this table show that in the herbicidal action against broad-leaved or dicotyledonous weeds, here a mixture from Sinapis arvensis, Chrysanthemum segetum, Chenopodium album, Viola tricolor and Anthemis arvensis, the compounds according to the invention A and B are as good as the chemically related comparison agents C and D or like the one that is often used in cereals Product E are.

They protect wheat and barley as well as product E, while preparations C and D are too good for cereals damage. The two weed grasses Poa and Apera are controlled by the two products according to the invention as well as by the comparison remedies C, D and E. Against Alopecurus myosuroides, especially the preparation A showed an excellent effect, too At 0.03 g of active ingredient per square meter, product B was on a par with comparison agents D and E, and was superior to preparation C. Farther A showed an excellent and B a good effect against Avena fatua; they outperformed comparison means D and E by far. Comparative agent C also worked well, but damaged the crop plants. Comparison agent F is a Special preparation for combating Avena and Alopecurus in grain, so the effect was very good against Avena, at 0.03 g / qm against Alopecurus only just enough against most other weeds much too weak.

The table shows that substances A and B according to the invention in cereals using the pre-emergence method, in addition to broad-leaved or dicotyledonous weeds, weed grasses that are difficult to control (Gramineae) such as Avena fatua and Alopecurus myosuroides destroy sufficiently, while the comparison means either in their broad impact not enough or damage the crops too much. Compared to the comparison means F results also an application-related advantage insofar as it sufficient to spray the new substances onto the floor, whereas Preparation F must be worked mechanically into the soil, in practice e.g. by means of a harrow, which is an additional Operation means.

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Example 5 Pre-emergence procedure

In a manner similar to Example 4, seeds of Alopecurus, Triticum and Hordeum sown in pots and on the day of sowing treated. Here were the substances A and B (see. Example 4), E (Terbutryn) and the product

-NH-C-N

Chlortoluron (cf. U. S.P. 2.655.455 Nieder1.P. Annm. 6,902,214)

used. The two preparations Terbutryn and Chlortoluron are used as specific comparative agents for combating Alopecurus used in cereal crops.

The result after 4 weeks looked like this:

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ORIGINAL INSPECTED Table II

Pre-emergence effect against weeds in cultivated plants, Dosage in g of active substance per square meter of soil surface.

CO OO O

Plant species preparation 0.0075 Degree of damage in % DL 95 at ro 95 0.03 Alopecurus 039041 Alopecurus myosuroides A. 75 100 0.0075 B. 25th 100 0.015 E. 65 100 0.0195 G O 95 0.023 Triticum aestivum A. O 35 B. O 20th E. O 20th G O 15th Hordeum distichum 'A O 30th B. O 20th E. O 15th G 20th 0.015 100 95 85 90 10 0 5 0 5 5 10 0

■ -. ■■■■ - 13 -

A comparison of the substances A and B according to the invention with known standard products showed that the former against Alopecurus are significantly more effective than the comparison remedies. If you use the dosages for a precise comparison, the are needed to damage the weeds to 95%, so gets the values given in the last column under DL 95 (partly interpolated with the help of logarithmic curves); one sets furthermore the value of the comparison agent G (chlorotoluron) and If the value of the other substances relates to this value, the following relative numbers are obtained:

DL 95 in Alopecurus G (chlorotoluron) - 100 {

B (Terbutryn) - 85

Preparations A - 35

Preparations B - 65

So you need A and B of the substances according to the invention only 35% or 65% of the dosage of the comparison agent chlorotoluron, to adequately combat the weed Alopecurus.

The figures also given in Table IV for the damage to the crop plants show that the inventive Preparations in relation to their weed effects wheat and Preserve barley just as well as the comparison agents.

Example 6 /

Post-emergence method .

Seeds of the broad-leaved weed Sinapis arvensis, Chrysanthemum segetum, Chenopodium album, Viola tricolor and Anthemis arvensis and seeds of the weed Avena fatua and the cultivated plant Triticum aestivum (wheat) were sown in pots, the plants germinated and after 3 weeks sprayed with aqueous suspensions of the preparations A and B according to the invention.

A product emulsified in water was used as a comparison medium, the active ingredient 2-chloro-3- (4'-chlorophenyl) methyl propionate

209808/1964 originally inspected

CH ₀ -CH-C-OCIL Cl O

contained. The experiment was evaluated 4 weeks after the treatment. The result is shown in Table III below:

Table III

1 Preparation:
Dosage: Weed: A.
0.03 0.06 B.
0.06 • 95 Avena fatua * ■.
Ir ".
H
0.06 0.5 Broad-leaved species: 95 100 95 10 Mixture of different
species 10 O Crop plant:
Triticum aestivum 96 100 93 O * 10 O O O

These figures show that the preparations according to the invention also are effective in the post-emergence method, whereby product A was already effective at 0.03 g / m² and excellent at 0.06 g / m² against broad-leaved weeds and wild oats. Almost as good B showed effects; the wheat remained undamaged in any case.

The comparison agent H, on the other hand, is a special preparation for combating the airport after emergence was practically ineffective as a herbicide at 0.06 g / m²; it required eight times the dosage, in order to control the wild oats sufficiently, but even then showed no effect against broad-leaved weeds.

209808/1964

ORIGINAL INSPECTED

Example 7 Pre-emergence procedure

In a manner analogous to Example 4, weeds and Cultivated plants sown and treated. Here again the Preparations A and B according to the invention used. The product served as a means of comparison

-nh-c-n:

Fluometuron

CH ₃

a frequently used preparation for cotton.

The result, recorded 4 weeks after the treatment, is shown in the following table.

Table IV

Pre-emergence action against weeds and crops; Dosage in g more active Substance per square meter of soil surface.

Preparation: A. 0.03 0.12 B. 0.03 0.12 J 0.03 0.12 Dosage: Weeds: 95 1OO 40 Xanthium pungens 100 95 30th Bidens pilosa 100 1OO 100 Amaranthus retroflexus 1OO 95 85 Chenepodiura album. 95 95 85 Setarla faberii 100 100 85 Eleusine indica Cultivated plants: 0 20th 10 50 40 85 Oryza sativa (Rice)

/ NSPECTEO

Preparation:
Dosage: A.
0.03 0.12 B.
0.03 0.12 J
0.03 0.12 Zea mais
(Corn) 0 40 0 25th 30th 90 Gossypium hirsutum
(Cotton) 0 0 0 20th 0 40 Arachis hypogaea
(Peanut) O 10 10 50 30th 80 Glycine soy
(Soybean) 0 50 0 60 60 90 Phaseolus vulgaris
(French bean) 10 60 0 10 20th 90

From these figures it can be seen that the substances according to the invention A and B in a dosage of 0.03 g / m² work well to very well against the weeds listed. The comparator product J (Fluoraeturon), on the other hand, had one against Xanthium and Bidens too little effect. Here, too, it was found that the inventive Substances have a selective herbicidal action against difficult-to-control weeds in cereals, in the present case in rice and corn and other crops.

At a four times higher dosage (0.12 g / m2) all products had against all weeds 100% effect. So here is just that nor the action against cultivated plants given to show like this in the case of severe overdose, which is common in practice occurs, react to the respective preparation.

This shows that the substances according to the invention in the normal dosage (0.03 g / m2) do not damage cotton, for example, as well as fluometuron. In the case of overdoses, on the other hand, the differences become clear. Fluometuron damages cotton

209808/1964

significantly stronger than the substances according to the invention.

These can also be used in peanuts, soybeans and French beans, i.e. they are harmful in the herbicidally effective dosage of 0.03 g / m² the crops concerned do not. Even in overdoses, the cultures partly remain practically undamaged, Good uses can be found in peas, cabbage and tobacco. The comparison agent, on the other hand, caused damage in almost all of them mentioned cultures too strong.

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Claims (1)

Claim: Herbicidal agents for the selective control of weeds in cereals, cotton, peanuts, legumes and cabbage, marked by the content of an active ingredient according to the formula CH ₃ -nh-c-n: where R - is hydrogen or methyl, as well as a network, Adhesives, dispersants, liquid or solid carrier material, grinding aids, granulating agents y> the one other biocidal Active ingredient or fertilizer. 209808/1964