DD202372A5 - HERBICIDAL AGENT - Google Patents

Abstract

A new herbicidal agent, which is particularly suitable for selective weed eradication in cereal or soybean plantings, contains as active ingredient a Phenoxybenzoesäureverbindung the general formula I. The agent acts especially against Gaensefuss, foxtail grass, ragweed, chickweed, Spitzklette, Pupurwinde or Indian Mallow and acts advantageous applied in an application rate of 0.1 to 2 kg of active ingredient per hectare. A herbicidally active compound is prepared, for example, by reacting an acid chloride of the general formula II with a sulfonamide of the general formula III.

Description

The invention relates to a herbicidal composition containing as active ingredient certain phenoxybenzoic acid derivatives having a sulfonamide group. These agents are especially useful for controlling weeds in soybean and cereal crops.

Characteristic of the known technical solutions:

Herbicides derived from phenoxybenzoic acids and their esters are described in U.S. Patent Nos. 3,652,645, 3,784,635, 3,798,276, 3,873,302, 3,907,866, 3,928,416, 3,983,168, 4,063,929 and EU Patents 3416 and 23 392.

Object of the invention:

The aim of the invention is to provide new active herbicidal compositions based on Phenoxybenzoesaurederivaten, which are particularly suitable for selective weed killing in soybean and cereal crops.

Explanation of the essence of the invention:

24 198

The invention relates to herbicidal compositions which contain as active ingredients benzoic acid derivatives with sulfonamide groups which are of the general formula I

correspond in the 12 3

X, X, and X are each a halogen atom, for example a fluorine, chlorine or bromine atom, a polyhalogenated alkyl group having 1 to 4 carbon atoms, in particular CF.sub.1, NO.sub.N, CN, an alkyl group having 1 to 4 carbon atoms , an SO ~ alkyl group having 1 to 4 carbon atoms, for SO ₂ NH ₂ , NO, COO alkyl having 1 to 4 carbon atoms in the alkyl part,

- Y ¹ -N = or -CH = is

Y ^{2 represents} -N or -CX ⁷ , provided that Y is not -N = when Y ^{2 is} -CX ⁷ ,

Y is an oxygen or sulfur atom,

X is a hydrogen atom or an alkyl group

to 4 carbon atoms, which is optionally substituted by in particular halogen atoms, meaning

2 0 tet,

X is a hydrogen atom or an alkali metal atom, in particular a sodium or potassium atom, or a cationic optionally quaternary ammonium group, or an alkyl group having 1 to 4 carbon atoms which is optionally substituted by, in particular, halogen atoms, or a halogen atom, in particular a chlorine atom,

he

- X is an optionally substituted alkyl group having preferably 1 to 4 carbon atoms or an optionally substituted aryl group, in particular phenyl group, wherein as substituents halogen atoms or alkyl, amino, cyano, nitro, alkoxy, hydroxyl, formyl or Mercapto groups come into question, - X is a hydrogen atom or a halogen atom.

A preferred family of the active ingredients provided according to the invention is characterized in that in the formula I

X ¹ = CF-, X ² = Cl,

X = Cl or preferably NO-,

- X ⁵ = H, Na or Cl and - Y ¹ and Y ^{2 are} each -CH =.

The new herbicidally active substances can be prepared in various ways:

According to a first procedure, an acid chloride of general formula II is reacted with a sulfonamide of general formula III, wherein the various groups and / or substituents have the meaning given in connection with the general formula (I).

The reaction is advantageously carried out at temperatures of 50 to 15O ⁰ C, preferably between 80 and HO ⁰ C, in a solvent such as an optionally halogenated aliphatic or aromatic hydrocarbon. The concentration of compounds of the general formula (II) and (I) is generally in the range of 1 to 80%, preferably in the range of 10 to 30%. Preference is given to working in the presence of an acid acceptor, for example a tertiary amine, in particular triethylamine and pyridine

 30

In the just described reaction between the compounds of the general formulas (II) and (III)

X is preferably not a halogen atom. The compounds of the general formula (I) in which X "denotes a halogen atom are generally obtained by

241981

effect of a hypohalite on the corresponding compound in which X represents a hydrogen atom. This reaction is generally carried out in an aqueous medium at a pH above 10, preferably above 11.5 and at a temperature in the range of 0 to 50 ^° C.

The acid chloride of the general formula (II) is prepared in a conventional manner by the action of SOCl »on the corresponding acid of the general formula IV. The acid of the general formula (IV) and of the sulfonamide of the general formula (III) is prepared by means of known from the literature method.

According to a second procedure, the inventively provided compounds of the formula I in which X is not a halogen atom, by reacting an acid of the general formula (IV) with 0 an isocyanate of the general formula (V). wherein, in the formulas, the various substituents or groups have the same meaning as in the general formula (I). This reaction is advantageously carried out in the presence of a solvent and preferably in the presence of a catalytic amount of an organic base. The reaction temperature is usually in the range from 20 to 100 ^° C., preferably in the range from 40 to 80 ^° C. The concentration of products of the general formulas O (IV) and (I) generally makes up 5 to 70% by weight.

Useful solvents for this are aliphatic or aromatic solvents which are optionally halogenated, for example benzene, toluene and xylene.

- he -

The organic base is, for example, p- (dimethylamine) pyridine.

The isocyanates of the general formula (V) can be prepared by methods known per se.

The first method of the invention using a reactant of the general formula (III) is preferred when X is an aliphatic group; the second procedure, in which an isocyanate of the general formula (V) is used, is group.

is preferred, when X is an aromatic

The compounds of the general formula (I) in which X represents a hydrogen atom can be converted into the corresponding compounds in which X is an alkali metal atom in a manner known per se, in particular by means of the processes known to those skilled in the art of phenoxybenzoic acids with sulfonamide group are applicable.

For further explanation, the preparation of the following compounds is given:

Compound of the formula I A:

In 15 ml of toluene containing 2 g of thionyl chloride was dissolved 3 g (6.9 mmol) of 1- (1-carboxyethyl) -5-2-chloro-4-trifluoromethylphenoxy-2-nitrobenzoate.

The solution was refluxed for 4 hours; then it was cooled. The solvent and the excess thionyl chloride were distilled off under reduced pressure. The residue became

241981 4

taken up in 25 ml of tetrahydrofuran. There were added 0.9 g of methanesulfonamide (CH ₂ SO ₂ NH ₂ ) and a catalytic amount (about 5 mg) of p-dimethylaminopyridine. Further, 10 ml of a solution of 0.77 g of triethylamine in anhydrous tetrahydrofuran was added dropwise. After completion of the addition, stirring was continued for a further 2 hours, 50 ml of tetrahydrofuran were added again, and the solution was washed twice with 25 ml of aqueous, 100% strength by weight hydrochloric acid and with brine each time. It was then dried over MgSO ₄ , filtered and the solvent removed under reduced pressure.

The residue was purified by chromatography using a SiO ₂ column (solvent: 10% acetic acid in CHCl-).

0.5 g of compound of the formula I A was obtained.

0 compound of the formula IB:

150 ml of a solution of 50 g (261 mmol) of p-toluenesulfonyl isocyanate in toluene were added dropwise and with stirring to 350 ml of a solution of 100 g (239 mmol) of carboxymethyl-5- 2-chloro-4- (trifluoromethyl) phenoxy 2- nitrobenzoate and a catalytic amount (about 5 mg) of p- (dimethylamino) pyridine in toluene.

After completion of the addition, the whole was refluxed for 6 hours. It was then cooled and the solvent was distilled off in vacuo. A crude compound was obtained which was recrystallized from a mixture of toluene and hexane.

There were then obtained 115 mg (209 mmol) of (4-methylphenyl) sulfonylaminocarbonylmethyl-5-2-chloro-4- (trifluoromethyl) phenoxy-2-nitrobenzoate of the formula I B.

This compound melted at about 130 ^° C. and exhibited IR absorption bands (in KBr) at 3205, 1705 and 1580 cm.

In the NMR spectrum (recorded in CD ₃ -CO-CD ₃ with tetramethylsilane as standard), pics were 2.35 ppm (singlet for 3 protons), 5 ppm (singlet for 2 protons), and 7.3 to 8.5 ppm (Multiplet for 10 protons) observed.

1 5 compounds of formula IC and IC ¹ :

The sodium salt of Compound IB (Group N-Na) was obtained by reacting the compound obtained in Example 2 in anhydrous tetrahydrofuran with sodium hydride. Subsequently, the solvent was distilled off in vacuo. The IR spectrum of Compound I C had absorption bands at 1600 and 1735 cm.

In the same way compound C was obtained as the sodium salt (group N-Na) of compound I A.

Connection ID:

The procedure was as in 'Compound I B, but reacted carboxyethyl-5- 2-chloro-4- (trifluoromethyl) phenoxy -2-nitrobenzoate with p-toluenesulfonyl isocyanate. This gave 0.3 g of compound of the formula -I D.

4198 1 4

In the IR range, an absorption band at 1690 cm was observed; in the NMR spectrum, chemical shifts (indicated in ppm) of 1.42 (doublet, corresponding to 3 protons, coupling constant = 14 Hz) were observed,

2.4 (singlet, corresponding to 3 protons),

5.24 (quadruplet, corresponding to one proton, coupling constant = 14 Hz).

7.2 to 8.2 (multiplet, corresponding to 10 protons).

Connection IE:

The procedure was as for compound I A, but the starting compound used is carboxymethyl-5- 2-chloro-4-trifluoromethylphenoxy-2-nitrobenzoate.

This gave 1 g of an oil which was obtained from the compound of formula I E-.

0 The formula was determined by the IR and NMR spectra

confirmed.

Compound I F:

The procedure was as for compound I D, but the methanesulfonamide replaced by CH ^ -SOp-NH-CH. It was heated for a total of 8 9 hours. This gave 3 g of an oil consisting of the compound of the formula I F, which was confirmed by the IR and NMR spectra.

3 0 de.

The herbicidal compositions according to the invention contain as active ingredient a compound of the general formula I in combination with agriculturally acceptable solid or liquid carriers and also 5 surface-active agents. In particular, the inert and customary carriers and the conventional surfactants are suitable.

The compositions may also contain any other components, such as, for example, protective colloids, adhesives, thickeners, thixotropic agents, penetrating agents, stabilizers, scavengers: agents and a.m. as well as other known active compounds with pesticidal properties, especially insecticides, fungicides and herbicides, or with intrinsic., Which the growth of. Propagating plants, especially fertilizers or plant growth regulating properties. In general, the active ingredients provided according to the invention can be combined with all solid and liquid additives which are customary for the production of pesticides.

The application doses or expenditure amounts for the active substances provided according to the invention can vary within wide limits and depend above all on which weeds are involved and to what extent the plantings of the useful plants are usually affected.

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- ίο -

In general, the inventive compositions contain from 0.05 to 95 parts by weight of one or more I according to the invention provided active compounds, 1 to 95 wt .-% of one or more solid or liquid carrier and optionally O ₇ I to about 20 wt .-% of one or several surfactants.

As the carrier in the present description organic and inorganic substances of natural or synthetic origin are referred to, with which the active ingredient is combined to facilitate its application to the plant, on the seed or on the ground. This carrier is thus generally inert and must be agriculturally compatible, especially compatible. For the treated plant. The carrier may be a solid such as clays, natural or synthetic 'silicates, silicic acid'. Resins, waxes, solid fertilizers and the like; or it is liquid such as water, alcohols, especially butanol,: .Ester, in particular methyl glycol acetate, ketones, in particular cyclohexanone and isophorone, petroleum fractions, aromatic hydrocarbons, in particular the xylenes or paraffinic hydrocarbons, aliphatic chlorinated hydrocarbons, especially trichloroethane or aromatic chlorinated hydrocarbons, .insbesondere Chlorobenzenes, water-soluble or water-miscible solvents such as dimethylformamide, .Dimethylsulfoxid, N-methylpyrrolidone, liquefied gases' u , ,

'·

The surfactant may comprise an emulsifier, a dispersant or a wetting agent, as well as

ionic or non-ionic or a mixture of such agents. Examples thereof are the salts of polyacrylic acids, the salts of lignosulfonic acids, salts of phenolsulfonic acids or naphthalenesulfonic acids, polycondensation products of ethylene oxide and fatty alcohols or fatty amines, substituted phenols, especially alkylphenols or arylphenols, salts of succinic acid esters, taurine derivatives, especially alkyl taurates, esters Phosphoric acid and alcohols or polyoxyethylated phenols, esters of fatty acids and polyols and the derivatives of the above compounds with sulfate, sulfonate and phosphate groups. The presence of at least one surfactant is generally necessary when the active ingredient and / or the inert carrier are not water-soluble and the vehicle for the application is water.

The herbicidal compositions of the invention have very different 0 solid or liquid forms.

Examples of solid compositions are powders for dusts containing up to 100% of the compound of general formula (I) and granules, in particular those obtained by extrusion, by compression, by impregnation of a granulated support or by granulation starting from Powders have been obtained; the content of the compound of the general formula (I) in these granules is 0.5 to 80% in the latter case. The solid agents mostly contain 20 to 80% active ingredient.

24

4 - 12 -

Examples of liquid agents / i. Agents that are liquid in use are solutions, especially emulsifiable concentrates, emulsions, concentrated suspensions, aerosols, wettable powders or wettable powders, self-dispersible granules and pastes.

The .fluid agents usually contain 10 to 80% 'active ingredient · ·

The emuigierbaren or soluble concentrates usually contain 10 to 80% active ingredient; the ready-to-use emulsions or solutions in turn contain from 0.01 to 20% active ingredient. In addition to the solvent, the emulsifiable concentrates, if necessary, 2 to. 20% contain suitable additives, for example stabilizers, surfactants, penetrants, corrosion inhibitors, dyes and adhesives.

20 '·

Starting from these concentrates, it is possible by dilution with water to prepare emulsions or solutions of any desired concentration, which are particularly suitable for use on the plants.

The concentrated suspensions which can be sprayed are prepared so as to give a stable flowable product, in which the individual components do not settle (fine grinding); they

u ι 9 8 ι ** - ¹³ -

usually contain 10 to 75% active ingredient, 0.5 to 15% surfactants, 0.1 to 10% thixotropic agents, 0 to 10% further additives such as anti-foaming agents, corrosion inhibitors, stabilizers, penetrants and adhesives and as a carrier water or an organic liquid in which the active ingredient is little or insoluble. Certain solid organics or inorganic salts may be dissolved in the carrier to further counteract sedimentation or as antifreeze agents. the water.

The wettable powders are usually prepared to contain from 20 to 95% active ingredient plus, in addition to the solid support, from 0 to 5% of a wetting agent, from 3 to 10% of a dispersing agent and, if required, from 0 to 10% of one or more stabilizers and / or other additives such as penetrants, adhesives or anticaking agents, dyes and the like

'For the preparation of these wettable powders or wettable. Powder, the active ingredients are mixed in appropriate mixers intimately with the other additives or it is the porous Träger.imprägniert with the molten Wirkstoff.bei and the whole is milled in mills or other suitable reduction devices / obtained in this way spray powders, which advantageously wetted and in suspension. They can be suspended in any desired concentration in water; These suspensions are particularly well suited for application to the foliage of the plants. ,

24 1 9 B1 4

The "self-dispersible" granules (English term "dry flowable" - are slightly water-dispersible granules) have a composition that i_rn substantially equal to that of wettable powders. They can be prepared by granulating the formulations described for the wettable powders or by wet method, i. by contacting the finely divided active substance with the inert carrier or filler and with a little water, for example 1 to 20%, or by contacting the finely divided active substance with the aqueous solution of the dispersing agent or binder and then drying and sieving ', or else dry way by pressing and. subsequent crushing or grinding and sieving.

Pastes can also be made instead of wettable powders. The conditions and modalities of production and use of these pastes are the same or comparable to those of wettable powders or wettable powders.

As already said, the aqueous dispersions and emulsions include, for example, the agents. · Obtained by diluting a wettable powder or an emulsifiable. Concentrate with water, to the applicable according to the invention applicable agents. The emulsions may be water-in-oil or oil-in-water emulsions and have a thick mayonnaise-like consistency. ·

All these aqueous dispersions or emulsions or spray mixtures can be applied to the cultures or

Use plantings to be weed-cleared by any suitable means, generally by spraying or spraying, in dosages generally on the order of 100 to 1200 sprayings per hectare.

The granules used for soil treatment are generally prepared so that their dimensions are 0.1 to 2 mm, and they can be made by agglomerating or impregnating. " Preferably, the granules contain 1 to 25% active ingredient and 0 to 10% additives. Such as stabilizers, release inhibitors, binders and solvents.

The compositions of the invention are used for weed killing in crops, especially in cereal crops such as wheat crops. As well as soybean. For this purpose, an effective and non-phytotoxic amount of at least one of the compounds according to the invention is applied to the plants and / or to the soil of the area which is to be freed from weeds. These compounds are used in practice in the form of the herbicidal compositions of the invention described above. In general, amounts of active ingredient of 0.01 to 5 kg / ha, preferably from 0.1 to 2 kg / ha lead to good results, of course, the choice of the amount of active substance to be applied, of the problem to be solved by the climatic conditions.

2419

and the . in consideration 'drawn crops. The treatment can ei.-neither before emergence of the crops and the weeds or before sowing the crops incorporating into the soil - this incorporation is thus an additional measure in the inventively provided treatment, or after emergence - .. Other Types of treatment are also in question: For example, you can apply the drug on the ground with or. Without incorporation, and before Pikieren the. Crop-planting.

The compounds according to the invention can be used to treat both one-year-old useful plants and perennial crops. In the latter case, the active ingredients are preferably localized, for example, applied in the rows between the crops. -

In the case of soya, the activity of the agents according to the invention is particularly interesting when the soya plantings are infested by dicotyien weeds such as Indian Mallow, Spitzklette, purple winds and Windenknöterich. In the case of cereals, the activity of the funds is particularly interesting if the cereal crops with dicotyien Weeds, especially goosefoot, arched foxtail, high Ainbrosie, Windenknöterich, Chrysanthemum, Ackersenf and in particular chickweed and lab herb are infested.

14 19 8 1 4

embodiments

4 - 17 -

Examples of the composition of emulsifying

strong concentrates: 5

a) active ingredient. 250 g

polyethoxylated alkylphenol - 30 g calcium alkylarylsulphonate - 50 g petroleum fraction, which at 160 to

185 ⁰ C passes over 670 g

_: b) active ingredient 350 G ^: polyethoxylated castor oil 60 G sodium alkylarylsulfonate '40 G 15 • cyclohexanone 150 G ifylol 400 G ^! c) active ingredient 400 G 20 polyethoxylated alkylphenol 100 G T 4- V, -ι τ Ι αηπΐ iiVnl -τη ο + Ή \ / Ί e> · (- Ή ι => Τ " 250 σ

* Petroleum fraction, which at 160 to

185 ⁰ C passes "'.""250 g

d) active ingredient. ⁴⁰⁰ 9 polyethoxylated tristyrolphenol

phosphate. , 50 g of polyethoxylated alkylphenol

phosphate. , '65 g

3Q-Sodium alkylbenzenesulfonate. 35 g

Cyclohexanone 300 g

* Petroleum fraction with mp 1.60 to 185 ⁰ C .150 g

* aromatic

250 G 25 G 100 G 50 G 575 G

e) active ingredient _; 4UO g / l alkyl dodecyl benzene sulfonate. 24 g / 1 oxyethylated nonylphenol with

10 Ethyilenoxideinheiten. 16 g / 1 5 cyclohexanone '\ 200 g / 1 of aromatic solvent filled up. 11 ·

f) active ingredient

10 · epoxidized plant, oil. Mixture of .Alkylarylsulfonat and polyglycol fatty alcohol ether

 Dimethylformamide xylene

5 '""

II suspension concentrate:

Active ingredient 50

polyethoxylated tristyryiphenol ^;

0 Phosphate Polyethoxylated Aikylphenol Sodium Polycarboxylate Ethylene Glycol Organopolysiloxane Oil. (Antifoam)

Polysaccharide VJa s s

III wettable powders: 30

a) Active ingredient - 50%

Calcium lignosulfonate, deflocculant. · 5% "

50 G G 50 G G 20 G 50 G ... 1 G 12 5 316 5

24 198 1 4

Isopropylaminaphthalene sulphonate, anionic wetting agent. , 1% silica to prevent clumping. , "5% kaolin, filler." 39%

 b) active ingredient.

Sodium alkylnaphthalenesulfonate Sodium lignosulfonate Silica to prevent lump formation kaolin. ·

c) "Active ingredient

 Sodium alkylnaphthalenesulfonate.

Methylcellulose of low viscosity. , · · 'Diatomaceous earth. ,

2 0 d) active ingredient

: Sodium dioctylsulfosuccinate. synthetische.Kieselsäure

e) Active substance 25 Sodium lignosulphonate

Sodium dibutylnaphthalenesulfonate silica.

'f) / active ingredient: isooctylphenoxy-polyoxyethylene

ethanol

Mixture of equal parts by weight of chalk from Champagne and hydroxy

ethyl cellulose '17 g

80 % 2 % 2 ^% 3 % 13 ^% 50 % 2 2 _% 46 ^% 90 % 0 , 2% 9 ,8th % 400 G 50 G 10 G 540 G 250 g 25 g

£ ^ i 3 8 ι ** - 20 -

Sodium aluminum silicate 543 g

Diatomaceous earth 165 g

g) active substance ... 100 g. Mixture of sodium salts of saturated fatty acid sulphates. , .... 30 g.

, Condensation product of naphthalene

  sulfonic acid and formaldehyde. 50 g

Kaolin. '. · 820 g of 10IV granules for soil treatment

Active ingredient '50 g

Propylene glycol 2 5 g

Clay (sieve size 0.3 to 0.8 mm) 925 g 15

; V self-dispersible G?

Active ingredient. 800 g

Sodium alkylnaphthalenesulfonate

NatriujTunethylen-bis-naphthalene sulphonate. 80 g

Kaolin. , .10Og

25 VI application examples :

a). In 20 cm × 25 cm containers filled with soil, crops and weeds were sown in rows of 10 cm in each case.The plant species used are listed in Table (I).

For cotton, corn, soy and 'Spitzklette' were each designed A to 5 grains per row 'and

the smaller species - Native American Mallow - Ackersenf, recurved foxtail, millet and green

241981

Borstenbinse were sown without counting the seeds, but in sufficient numbers, so that subsequently received a number of dense plantlets.

Until the plant emerged, the soil was watered from above.

Pre-emergence treatment was less than 1 day after sowing.

^; The desired stage of development for the postemergence treatment of cotton, soybeans, blackjack, Indian mallow, field mustard and goosefoot (Chenopodium)

the stage in which a real leaf or a true dreizelapptes sheet had formed. The maize plant had a height of 7.5 to 10 cm at the desired stage; in the case of (other) grass plants ¹ , the desired height was 2.5 cm.

The active compounds according to the invention were sprayed under a pressure of 2.5 bar at an application rate of 375 l / ha. The sprays consisted of a mixture in volumes of the 20 ml of water and 0.1. % surfactants (mixture of a polyoxyethyl ether and alkali metal (C 1 -C ₆ ) alkylbenzenesulfonates.

After. Treatment was carried out from below by the plants which had already accumulated, and from above by the seeds, which had not yet risen.

• 2 weeks after treatment, the activity determinations are based on a scale of 0 to 100%.

For the weeds, this scale means the extent of the eradication. In the case of crops, this scale means the extent to which the plants are attacked by the active substances or their phytotoxicity. The value 0 was attributed to the plants which were in the same state as the control plants; the rating 100 corresponds to the complete eradication.

10 Table (2) summarizes the results obtained with the compounds of formulas IΆ to IF.

b) Pre-emergence treatment of the plants 15

9 χ 9 χ 9 cm pots filled with light field soil were sown with a number of seeds, the proportion of which was determined by the type of plant to be tested and the number of seeds. Thickness of the seed

2 0 directed. ;

The seeds were covered with a layer of earth about 3 mm thick. After the soil had been moistened, the pots were treated with a spray mixture in an amount equivalent to a chemical rate of 5 00 l / ha; the spray mixture., Contained the drug to be tested in the desired concentration.

0 The spray mixture was prepared by diluting a wettable powder; The wettable powder in turn consisted of 5 g of active ingredient, 83 g of xylene, 8 g of nonylphenol-decaoxyethylene and 4'-calcium dodecylbenzenesulfonate. Depending on the active ingredient

/ 11Q Q 1 / - 23 -

Concentration der.Spritzbrühe was the applied drug dose 0.25 to 2 kg / ha.

The treated pots were then placed in trays and received here the necessary water from below and were kept at a 21 days .Temperature 22-24 ⁰ C under 70% relative humidity.

: After 21 days, the number of surviving plants in the treated pots was counted

For comparison, the number of surviving plants in control pots that had been treated under the same conditions, but with a spray mixture without active ingredient. You determined

the

in this way /. Percent extermination of the treated .Pplanzen, based on the control experiment without active ingredient. A degree of erosion of 100 ° means that the species of plant considered has been completely destroyed; 0% depollution means that the number of surviving plants in the pot treated with active ingredient was equal to the number of plants in the control experiment.

2 5 ^c ) Casserole treatment of plants .

In 9 χ 9'χ 9 cm pots, which were filled with light field soil, seeds were sown, the number of which aligned according to the respective plant species and the thickness of the seed.

The seeds were covered with a layer of soil about 3 mm thick and the seeds were allowed to germinate until the plants reached a height of 5 to 10 cm.

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Then, the pots were treated with a spray mixture in an amount corresponding to an application rate of 500 l / ha; the spray mixture contained the active ingredient in the desired concentration and was prepared in the same manner as in application example b).

Depending on the active ingredient concentration in the spray mixture, the applied active ingredient dose was 0.125 to 1 kg / ha. 10

The treated pots were then placed in wells which were watered from below and kept at 22 to 24 ^° C. under 70% relative humidity for 14 days.

After 14 days, the number of surviving plants in the potions treated with the spray mixture was counted and compared with the number of plants present in a pot treated equally but without active ingredient. In this way, the percent kill 0 of the plants, based on the control experiment, was determined.

100% destroying means that the considered plant species has been completely destroyed; 0% depreciation means that the number of surviving plants in the pot treated was identical. plants

25 in the control pot. ·

The results of application examples b) and c) are summarized in Tables (3) and (4).

Each of these tables (3) and (4) comprises on the one hand the pre-emergence results according to application example b) and on the other hand the post-emergence results according to application example c).

Table (3) shows the results obtained with the active ingredient of formula I B results; Table (gives the results obtained with the active ingredient of formula I E results

 5

d) Application Example a) was repeated by diluting an emulsifiable concentrate with water prepared using xylene as a solvent containing only 10% active and 5% surfactant. The amounts of the active ingredients were the same as in the application example a).

Dilution was carried out by obtaining a spray mixture of the same concentration as in this application example a). When using the remedy, the same results were obtained for the protection of the plants. ^:

e) Application Example d) was repeated by diluting an emulsifiable concentrate containing 50% active ingredient and 15% surfactant with the ratio of the amounts of the two active ingredients reversed. The dilution was carried out in such a way that a spray mixture of the same concentration as in application example d) was obtained. In the application, the same 0 results were obtained for the protection of the plants.

f) Application Example d) was repeated by diluting an emulsifiable concentrate, which differed from that of Application Example d) only in that it

24

2 0% surfactant contained. In the application, the same results were obtained for the protection of the plants.

g) Application Example d) was repeated by successively using different pairs of surfactants in equal amounts; the one remedy was ionic, the other remedy was nonionic:

a) polyethoxylated hexylbenzene with 4 0 ethylene oxide units and Natriumhexylbenzolsulfonat;

15 J ₃ ) polyethoxylated dodecylbenzene with 4 ethylene oxide units and potassium kutylbenzenesulfonate;

c) polyethoxylated ricin pine oil and calcium hexanol

sulfate; 20

d) polyethoxylated copra and ^{Natriumdodecanol-:} sulfate;

e) polyethoxylated hexanol with '2 O ethylene oxide units and Natriumdodecylöenzolsulfonat;

; f) polyethoxylated. Styrylphenol with .10 ethylene oxide units and calcium decylbenzenesulfonate and

0: '

^: G) polyethoxylated tristyrylphenol with 8 ethylene oxide and calcium dodecylbenzenesulphonate.

4 1

With these different agents, comparable results were obtained as in application example a).

h) The procedure was as in the application example d), but the emulsifiable concentrate replaced by a concentrated suspension / emulsion of the same composition with the modification that the organic solvent was replaced by water and that 0.1% heteropolysaccharide obtained by fermentation of Xanthomonasbakterien , had been added. Comparable results were obtained as in application example a).

i) The procedure was as in Application Example d), but the emulsifiable concentrate replaced by a wettable powder containing 60% active ingredient, 2% sodium dodecylnaphthalenesulfonate, 2% sodium lignosulfonate, 3% silica as an anti-lumping agent and 0 13% kaolin.

The same results were obtained as in application example a).

j) The procedure was as in application example d), but the emulsifiable concentrate replaced by a wettable powder containing 3 0% active ingredient, 2% sodium dodecylsulfonate and balance to 100% diatomaceous earth.

'Comparable results were obtained as in .Application Example a).

The experiments carried out thus show the advantageous properties of the erfindungsge-

means in the treatment of crops, and in particular of soya and cereals, including maize, in both pre-emergence and postemergence treatment.

Tables 1 to 4

/ 1 Ω Ο

4 I j ti

- 29 -

1Α-56 172

table

crops:

Corn

Cotton wheat rice soy ..

MA BW WE RE SO

weeds:

barnyardgrass Echinociiloa crus-galli EC SF Giant foxtail Setaria faberii SV Green bristlebin Setaria viridis DS crabgrass Digitaria sanguinalis. AT Native American Abutilon mallow theophrasti SI Groundhog .. · Setaria italica XP cocklebur Xanthium pennsylvanicum SA Charlock. , Sinapis arvensis AR  Bent backwards · Amaranthus. foxtail retroflexus IP morning glory Ipomea purpurea SS (tropical weed) Sida spinosa. AF oats Avena fatua PC buckwheat Polygonum convolvulus AA High ragweed ambrosia artemisiifolia

table

Connection 'No.

Time of application related to emergence

1 2 3 '

3 to

after

in front

to

to

to

in front

to

before after

Dose in kg / ha

2.24 0.14 1, 12 1.12 2.24 2, 24 1.12 1.12 1.12 1.12

"weeds

EC

80

BO 0

100 60 90 50

80 70 60 90 80 10 00 50 60 0

DS

90

90 30 90 10 70 0

AT

70

10

30

100

70

40

100

70

70

50

XP

100

100

SA

100

100

in O

90

80

100

100

90

100

AR

80

90

100

100

90

60

100

100

100

50

SS

90 30

100 60

100 20 60 50

Slutzpflanzen

BW MA SO

40

30

9Π

50 10 50 90 10 70

30

50 0

20 3 0 30 10 50

4 ι a 8 ι ^

- 31 Table 3

preemergence 90 1 0.5 0.25 ! Jachauflauf 1 0.5 0.2 0 5 0.125 Dose in kg / ha 2 100 50 20 0 0 Agropyron 100 100 100 100 sorghum 100 100 100 90 50 20 0 0 Echinociiloa 100 100 100 100 80 80 0 0 Panicum 100 100 100 100 100 90 10 0 Digitaria 100 100 100 60 100 80 50 20 Abutilon 100 0 0 0 100 100 100 Xanthium 100 100 100 100 100 80 80 30 Chenopodium 100 100 100 100 100 100 100 90 Amaranthus 100 100 100 90 100 90 90 20 ambrosia 100 100 100 100 100 100 90 Polygonum 100 100 50 100 100 Ipomea 100 100 100 100 100 100 100 90 Sida 90 100 90 80 90 50 20 0 Galium is100 80 20 10 0 0 0 0 Alopecurus UE100 100 100 100 100 90 10 0 Setaria virid 100 100 100 100 90 60 20 0 Setaria faber 100 100 100 90 100 100 100 100 chrysanthemun 100 100 80 80 100 100 100 100 sinapis 100 100 100 80 20 0 0 Stellaria 0 10 0 0 0 10 0 0 0 wheat 10 10 0 0 10 0 0 barley 0 •O 0 0 0 0 0 Corn 30 0 .0 0 cotton o | ο 0 60 0 ο I ο soy

1981

Table 4

preemergence S 1 0.5 0.25 IT chauffeured 1 0.5 0.25 0 0,1,25 Dose in kg / ha 2 100 100 60 100 90 90 0 90 Galium 100 90 20 20 0 0 Setaria Yiridi 60 10 10 0 Echinochloa 90 20 20 10 Panicum- 40 40 40 20 Digitaria abutilon 100 90 50 10 0 Xanthium 100 100 100 Chenopodium 100 100 100 100 100 100 80 Amaranthus 100 100 100 100 ambrosia 100 100 100 90 Polygonum Ipomea 100 100 100 100 100 100 100 Sida 80 100 1:00 100 100 Avena fatua 90 100 90 Alopecurus 100 20 0 0 LoIium 100 30 50 0 Setaria faberii 100 30 0 O Chryanthemum 100 100 100 100 80 10 0 sinapis 100 100 100 100 100 100 100 100 Stellaria 100 100 100 100 100 100 100 30 10 0 0 wheat 10 barley 10 0 0 20 0 0 Corn 10 0 ö 20 10 0 0 0 0

- Q M (ItH (I in. Λ <λ-

Claims (10)

invention claim 1. A herbicidal composition containing an active ingredient combined with at least one agriculturally acceptable inert carrier, characterized in that the active ingredient is a phenoxybenzoic acid compound of general formula I. is in the 12 3 X, X and X each represent a halogen atom, such as fluorine, Chlorine or bromine, a polyhalogenated alkyl group, NO ₂ , CN, an alkyl group, SO ₂ NH ₂ , NO, COO-alkyl, Y is one of the groups -N = or -CH =, Y is one of the groups -N = or -CX ₇ =, provided that Y ^{1 is} not N when Y ^{2 is} -CX ₇ 15 stands, Y is an oxygen or sulfur atom, X is a hydrogen atom or an optionally substituted alkyl group means - X represents a hydrogen atom or an alkali metal atom or a cationic, if appropriate 1 is a quaternary, ammonium group or an optionally substituted alkyl group or a halogen atom, X is an optionally substituted alkyl group 5 or an optionally substituted aryl group, in particular the optionally substituted phenyl group, - X is a hydrogen atom or a halogen atom. 2. Means according to item 1, characterized in that in formula I X ¹ = CF ₃ , X ² = Cl, - X ³ = Cl or ₃
- X ⁵ = H, Na. or Cl, - Y and Y are each the group -CH =. 3. Means according to one of the items 1 or 2, characterized by 2 0 that the alkyl group (s) in the formula I 1 to 4 carbon atoms. - 4. 'Appropriations under one of items 1 to 3, characterized in that in the form 4 25 mel I X is substituted by halogen atoms and / or X by halogen atoms or alkyl, amino, cyano, nitro, alkoxy, OH, formyl or mercapto groups. 5. Composition according to one of the items 1 to 4, characterized in that it contains 0.05 to 95 wt .-% of active ingredient. 6. Means according to one of the items 1 to 5 / characterized by 35 that it is liquid and contains 10 to 80% of active ingredient. - 30- 7. Means according to one of the items 1 to 5, characterized by that it is solid and contains 20 to 80% active ingredient. 8. Composition according to one of the items 1 to 7, characterized in that it contains 0.1 to 20% surfactant. 9. Use of the agent according to one of the items up to 8 in a soybean plantation which is infested or capable of being infested with at least one of the weeds: Indian mallow, Norway spike, Purple wind or Chickweed. 15. 10. Use of the agent according to any one of items 8 to 8 in a cereal plantation infested or infested with at least one of the weevil, foxtail, ragweed or chickweed weeds 2 0 can be. 11. Use according to one of the items 9 or 10, characterized in that the active substance of the general formula (I) in. used in an amount of 0.1 to 2 kg / ha. Blue Tzu_3__Seiten Drawings 7228 formula sheet χ ⁴ χ ⁵ CO-Y ³ -CH-CO-N-SO ₂ -X CO-Y ³ -CH-COCl "3 X ⁶ -SO ₂ -NH-X ⁵ (III) 3 I
CO-Y-CH-COOH (IV) if - I : ⁶ -so ₂ -n = c = o (V) CF. COO-CH-CO-Nh-SO ₂ -CH ₃ (I A) Cl. CF. A \ CO-O-CH ₂ -CO-NH-SO ₂ - no., ³ i (IB. '') N-Na salt of I..B (IC) N-Na salt of I A (I C)   Cl CH ₃
CO-O-CH-CO-NH-SO ₂ - ^ / ~ ^CH 3 NO- (I CF. Cl CO-O-CH ₂ -CO-NH-SO ₂ -Ch ₃
NO, (I E) 24 1 CF. Cl is CO-O-CH ₂ -CO-N-SO ₂ -CH ₃ CH, NO. (I F)