DD203454A5 - HERBICIDAL AGENT - Google Patents

Abstract

A new herbicidal composition containing mainly for selective weed killing in cereal or soybean plantations i. Contains, as an active ingredient a Phenoxybenzoesäureverbindg. the general formula I. D. agent works very well against Spitzklette, purple winds or Indian Mallow u. is advantageously used in an application rate of 0.1 to 2 kg of active ingredient per hectare. A herbicidally active compound is prepared, for example, by first reacting a phenoxyacetic acid of the general formula II with chlorosulfonyl isocyanate and reacting the reaction product of the general formula III with a compound R & exp1! H in the presence of a acid acceptor.

Description

The invention relates to novel selective herbicidal compositions containing as active ingredient a compound of the family of phenoxybenzoic acids.

Characteristic of the known technical solutions:

Various herbicidal derivatives of 15 Acifluorfens,. also as 5 - / "2-chloro-4- (tri-

f luormethyl) phenoxy - / - 2-nitrobenzoic acid, its salts and in particular derivatives of the alkyl, cycloalkyl, thioalkyl and phenylestej type, and acid amides or acid chlorides. Such compounds are described in US Pat. Nos. 3,652,645, 3,784,635, 3,873,302, 3,983,168, 3,907,866, 3,798,276, 3,928,416, 4,063,929.

OBJECT OF THE INVENTION:

The aim of the invention is to provide new herbicidally active agents. It is indeed desirable to be able to dispose of the largest possible number of herbicides from the contemplated family so that as many cases of weed killing as possible can be solved.

10 Presentation of the essence of the invention:

The invention thus relates to herbicidal compositions containing as active ingredient a compound of general formula I ₍ in the

W is a group -CH = or -CX ⁴ = or the nitrogen atom -N =,

12 3 4 X, X, X and X are each a halogen atom,

2 0; especially for F, Cl and Br ₇ for a poly

haloalkyl such as CF ₃ , for NO ₃ , CN, for an alkyl, alkoxy, alkylsulfonyl, suifonamide,; Nitroso or an alkyl carboxylate group, wherein the various alkyl groups and alkoxy I groups usually have 1 to 4 carbon atoms;

     M

R represents a group -OM or -N-COR or -N ^{/ R} or -XR ⁵ ; ^X R "

μ represents a hydrogen atom or an agriculturally acceptable cation, for example an alkali metal cation, in particular a sodium cation or an ammonium cation, which is optionally substituted;

/ 3

X is an oxygen or a sulfur atom,

2 5

R and R represent a hydrocarbon group, e.g.

an aryl group or a heterocyclic group which may be optionally substituted

may and preferably has from 1 to 12 carbon atoms;

3 4

R and R 'have the meaning given to R

and each may additionally be a hydrogen atom or an alkoxy group or together form a single divalent, optionally substituted hydrocarbon group;

15 R has one of the meanings given for M and can furthermore be an alkyl group having 1 to 4 carbon atoms.

2 3 4 5

Specifically, R, R, R * and R, the

may be the same or different, for an Aikylgruppe preferably having 1 to 4 carbon atoms and substituted with a maximum of 4 substituents such as aryl, especially phenyl, chlorine or bromine, OH group, .Alkoxygruppe, SH, alkylthio, carboxyl, or Alkylcarboxylat- cyano group; an alkenyl-ether alkynyl group having preferably 2 to β carbon atoms; an aryl group, in particular the phenyl group, optionally sub-

3 0 is substituted with a maximum of 4 substituents such as

Cl, Br, an alkyl, cyano, carboxyl-Aikylcarboxylatgruppe, NO ₂ , OK, alkoxy, SK, alkylthio group, wherein the various alkyl or alkoxy groups, which have been mentioned as substituents here, preferably 1 to have carbon atoms.

241980 6

Each of R and R can also be a hydrogen atom or together form an alkylene group having preferably 4 or 5 carbon atoms.

A preferred group of the inventively provided as active compounds of the general formula (I) are compounds in which X is a

2 3

Chlorine atom, X = CF-, X = Cl or preferably

N0 _? , W = -CH = and R has the same meaning as M.10

Preference is also given to the compounds in which R is a hydrogen atom.

The compounds are prepared according to any of the Ί5 reaction schemes "I to IH, in which, unless stated otherwise, the various substituents have the same meaning as given above.

Thus, in the process of Reaction Scheme II, a compound of the general formula (II) is first reacted with chlorosulfonyl isocyanate in a solvent or in a large excess of chlorosulfonyl isocyanate. The temperature is generally in the range from 20 to 200 ^° C., preferably in the range from 40 to 80 ^° C. The concentration of compounds of the general formulas (II) and (III) generally makes from 5 to 70% by weight. out. If work is carried out in the presence of a solvent, this may be, for example, an optionally halogenated, aliphatic or aromatic hydrocarbon, in particular toluene or a nitrile or an ether.

/ 5

241980

The reaction between the compound of general formula (III) and the compound of the general formula R-H is generally carried out at a temperature in the range from -40 ⁰ C to +60 ⁰ C, preferably in the range from -20 ⁰ C to +30 ⁰ C. Suitable solvents are the same as in the previous reaction stage. The concentration of compounds of general formulas (III) and (I) is generally in the range of 5 to 50%. The reaction is advantageously carried out in the presence of tertiary amines, in particular triethylamine and pyridine. Instead of a common acid acceptor, the compound RH itself can be used; this is then used in a considerably larger amount than is usually used if this compound is only the reaction partner.

The preparation of inventively provided as active compound 0 compounds will be explained in more detail below.

Preparation of compounds 1 to 19

To 20 ml of chlorosulfonyl isocyanate was added 18.1 g of acifluorfen; then, while stirring, the mixture was gradually warmed to 50 ^° C. until evolution, from HCl, ceased, followed by cooling. Then 50 ml of hexane were added; the precipitate was filtered off, washed with hexane and dried in vacuo. 22.2 g of 5- / 2 "-glor-4- (trifluoromethyl) phenoxy / 2-nitro-N-chloronylbenzamide were obtained, which were dissolved in 100 ml of acetonitrile

35 stirred, cooled to 0 ⁰ C and dropwise, a solution of 4.4 g of dimethylamine in 20 ml

241

Acetonitrile added. Thereafter, the temperature of the reaction mixture was allowed to rise to 20 ° C and then stirred for a further hour at this temperature. The acetonitrile was evaporated and the residue was dissolved in chloroform. This chloroform solution was washed with water, dried, concentrated and the residue purified by chromatography on silica using chloroform as eluent. This gave 10.8 g of compound no. 5 of the formula: I A

The various compounds Nos. 1 to 19 were prepared in the same way by replacing D'imethyiamine with the corresponding axnin or the corresponding alcohol. The formulas and physical characteristics of these compounds are summarized in Table 1.

24198 0

The herbicidal compositions of the invention contain as active ingredient a compound of general formula 1 in combination with agriculturally acceptable solid or liquid carriers and 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 protective colloids, adhesives, thickeners ,. thixotropic agents, penetrants, stabilizers, scavengers and a.jh. as well as other known active compounds with pesticidal properties, especially insecticides, fungicides and herbicides or with properties that promote the "growth of the plants, especially fertilizers or plant growth regulating properties all solid and liquid additives that are common for the manufacture of pesticides.

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

24 1980

In general, the agents according to the invention contain from 0.05 to 95% by weight of one or more of the active compounds provided according to the invention, from 1 to 95% by weight, of one or more solid or liquid carriers and, if appropriate, 0.1. to about 20% by weight of one or more 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 can be a solid like clays, natural or synthetic silicates, silicic acid, resins, waxes, solid fertilizers and the like; or it is liquid, such as water, alcohols, in particular butanol, esters, in particular methylglycol acetate, ketones, in particular cyclohexanone and isophorone, petroleum fractions, aromatic hydrocarbons, especially xylenes or paraffinic hydrocarbons, aliphatic chlorohydrocarbons, in particular trichloroethane or aromatic chlorohydrocarbons. in particular the chlorobenzenes, water-soluble or water-miscible solvents such as dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, liquefied gases and the like , ,

The surfactant may be an emulsifying agent, a disoiser or a wetting agent, as well as

38 0

ionic or non-ionic or a mixture of 'such' agents. Examples thereof are the salts of polyacrylic acids, the salts of xylene 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 from 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 if the active ingredient and / or the inert carrier is not are water-soluble and the adjuvant for the application is water.

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

Examples of solid agents are powder for dusts containing compound of general formula (I) up to 100% and granules, in particular those produced by extrusion, by compression, by impregnation of a granulated support or by granulation obtained from a powder; the content of the compound of the general formula (I) in these granules is 0.5 to 8% in the latter cases. The solid agents usually contain '' 20 to 80% active ingredient.

24 1980

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

The liquid funds contain mostly TO up to 80%; Active ingredient. '\ -

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

  ·. "·

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 in such a way as to obtain a stable flowable product in which the individual components do not settle (fine grinding);

24 19 8 0

usually contain 10 to 75 l of 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 a organic liquid in which the active ingredient is little or not soluble. Certain solid organics or inorganic salts may be dissolved in the carrier to additionally counteract sedimentation or antifreeze. the water.

The wettable powders are usually prepared to contain from 20 to 95% by weight of active ingredient and, 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 production of these wettable powders or .. wettable. Powder, the active ingredients are mixed in appropriate mixers: intimately with the further additives or the porous carrier is impregnated with the molten active substance and the whole is ground in mills or other suitable reducing devices. In this way, spray powders are obtained which can advantageously be wetted and brought into suspension. You can in any concentration you want. Ln be suspended in water; These suspensions are particularly suitable for application to the leaves of Pflan

241980

The "self-dispersible" granules (English term "dry flowable" - are slightly water-dispersible granules) have a composition which is substantially equal to that of the wettable powders. They can be prepared by granulating the formulations described for the wettable powders or by wet method, ie 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 fine ver - · divided active ingredient with the aqueous solution of dispersing agent or binder, followed by ¹ .Trocknen and sieving ', or, in the dry way by compression and subsequent grinding or milling and sieving. , , '

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

As already mentioned, the aqueous dispersions and emulsions, for example the agents obtained by diluting a wettable powder or an emulsifiable concentrate with water, belong to the applicable agents provided according to the invention. in oil or oil-in-water emulsions and having a thick mayonnaise-arabic consistency.

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

241980

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

\ : The granules used for soil treatment,

, are generally 'made so that their dimensions' 0.1 to 2 mm; they can be made by agglomeration or impregnation. Preferably, the granules contain from T to 25% active ingredient and from 0 to 10% additives. Such as stabilizers. Release inhibitors, binders and solvents. 15

The agents according to the invention are used for the destruction of weeds in crops, in particular in cereal crops, such as vejane crops, and in soybean, in which case the plants and / or the soil of the area which is to be freed from weeds. an effective and non-phytotoxic plant to the crops is applied to at least one of the compounds according to the invention These compounds are used in practice in the form of the herbicidal compositions described in detail above from 0.01 to 5 kg / ha, preferably from 0, "1 to 2 kg / ha to good results, 0 of course, the choice of the amount of active substance to be applied, of the problem to throw solved, from the climatic Conditions.

241380

and the crops considered. Behanöbng can ei. "Neither before emergence of crops and weeds.oder before sowing the crops .unter incorporated into the soil - this incorporation is thus an additional measure in the inventively provided treatment, or after emergence - done. ,

: Other types of treatment are also possible: For example, you can apply the active ingredient to the soil. with or without training, and before

^; Pikieren the. Crop-planting.

With the means according to the invention, one-year crops as well as perennial crops can be treated. In the latter case ·. "The" means preferably localized, for example applied in the rows between the crops. ^ - ''

24 1 98 0

embodiments

I Examples of the composition of emulsifiable concentrates:

a) active ingredient

polyethoxylated 'alkylphenol Caiciumalkylarylsulfonat petroleum fraction, die.bei 160 bis

^: 185 ⁰ C goes over '

G

30 g

50 g

G

b) active ingredient

Polyethoxylated castor oil Sodium alkylarylsulfonate Cyclohexanone ^ ylOI

ic) Active ingredient 0 polyethoxylated alkylphenol

Ethyl narrow-lyc-myrether * 'petroleum fraction, which passes at 160 to 185 ⁰ C -

5 d) active ingredient.

polyethoxylated tristyrolphenol phosphate. · '' ''.

polyethoxylated alkylphenol phosphate. ·

Sodium alkylbenzene sulfonate ·

Cyclohexanone * Erdöfraktion mt Fp 1.60 'to 185 ⁰ C.

3 50 00 G 60 G 40 G 1 50 G 4 00 G 4 00 G 1 00 G 2 50 G 250 G 4 G

50 g

"65 9 35 g

.150 g

* aromatic

241980

250 G 25 G   ioo G 50 G 575 G

e) Active substance _:. 4U0 g / 1

Alkyldodecylbenzenesulfonate. 24 g / 1 oxyethylated nonylphenol with

10 ethylene oxide units. 16 g / 1 cyclohexanone - made up to 200 g / l of aromatic solvent. 11-

 f) active ingredient

· Epoxidized.plant.oil. Mixture of .Alkylarylsulfonat and polyglycol fatty alcohol ether

Dimethylformamide '. Xylene 15 II suspension concentrate:

Active ingredient 50 g

polyethoxylated tristyrylphenol-0-phosphate

polyethoxylated alkylphenol sodium polycarboxylate ethylene glycol ...

Organopolysiloxane. (Antifoam)

polysaccharide

V7asser

III wettable powders: 30

a) active ingredient 50%

Calcium lignosulfonate, deflocculant '· 5%

5 0. G G 5 0 G G 2 0 G 5 0 G 1 G - 2, 5 31 6 5

241980

Isopropyinapbtalinsulfonat, anionic wetting agent '. , ·. 1% silica for. Prevention of lump formation. , \. 5% kaolin, filler '. , "· 39%

b) active ingredient. '80% sodium alkylnaphthalenesulfonate 2% sodium lignosulfonate'. , 2%

10 silicic acid to prevent the

; Lump formation. 3%

, '. Kaolin. · 13%

c) active ingredient. , 50%

, Sodium alkylnaphthalenesulfonate. 2% low viscosity methyl cellulose. , ·. 2% diatomaceous earth 46%

d) Active substance 90%

Sodium dioctylsulfosuccinate. 0.2%

synthetic.silicic acid. 9.8%

 : e) active ingredient. 4 00 g

Sodium lignosulfonate 50 g

Sodium dibutylnaphthalenesulfonate 10 g.

Silica. , 54g

• f); Active ingredient: 25 g of isooctylphenoxy-polyoxyethylene

Ethanol ^'25 Mixture of equal parts by weight of chalk from Champagne and hydroxy

ethylcellulose '. "17 g

241980 6

Sodium tri-aluminum-silicate silicate 542 g

Diatomaceous earth 165 g

g) active ingredient .- -. 10og

.Mixture of .sodium salts of

saturated fatty acid sulfates. , 30 g

; Condensation product of naphthalene sulfonic acid and formaldehyde 50 g

Kaolin. '.,. · · 820 g

10IV granules for soil treatment

Active ingredient · 50 g

Propylene glycol 25 g

Clay (sieve size 0.3 to 0.8 ram) - 925 g

'

; V self-dispersible G

Active ingredient. 80g

0 sodium alkylnaphthalenesulfonate · .2Og

 Sodium in-ethylene-bis-naphthalene sulfonate. 80 g

Kaolin "." 10 g

Vl application examples :

a) Pre-storage of plants.

0 In 9'x9 χ 9 cm large pots that are lighter in weight

Arable soil was sown, a number of seeds were sown, the number of which was based on the considered plant species and the thickness of the seed.

241 980

The pots were treated with a spray mixture in an amount corresponding to an application rate (volume) of 500 l / ha containing the active ingredient in the. contained desired concentration.

The treatment with the spray mixture was thus carried out so along the seeds were not yet covered with soil again (spray liquor referred to here all diluted with water herbicidal agent, so.wie they are applied to the plants). The spray mixture used for the treatment was an aqueous suspension of the active ingredient containing. 0.1% by weight of surfactant consisting of a polyethoxylated alkylphenol,

15 especially decaoxyethylated nonylphenol

(Trade name Cemulsol NP10) and 0.04 wt. Surfactant consisting of the laurate of the polyoxyethylene derivative of sorbitol (Tween 20). , ,

This suspension was obtained by mixing the components together and grinding to a mean particle size below 40μΐη. Depending on the active substance concentration of the

Spray liquor was the applied dose _; Active ingredient 0.25 to 4 kg / ha.

After treatment, the seeds were covered with a layer of soil about 3 mm thick.

30. ,

The pots were then placed in trays in which they irrigated from below and for 21 days at a temperature of 22 to 24 ⁰ C and at 70% relative humidity

35 were held.

241980

After 21 days, the number of live plants in each treated pot was counted and compared with the number of live plants present in a pot treated for comparison under the same conditions but 5 with a non-drug spray liquor. In this way the percentage of eradication of the treated plants relative to untreated plants was determined. A percentage

Extermination of 100% means that the plant species in question had been completely destroyed; a percent kill of 0% means that the number of live plants in the pot treated was equal to the number of treated plants in the. Control pot ·

: 'b) post-emergence treatment of plants

In 9 χ 9 χ 9 cm pots, which were filled with light field soil, seed grains were seeded, the number of which was determined by the type of plowed seed and the thickness of the seed grain.

Subsequently, the grains were covered with a layer of soil about 3 mm thick and allowed to germinate when the plantlets had reached the desired stage of development. The growth stadiuiri targeted for the treatment of grass plants (monocotyledonous plants) was the stage of the "second leaf in distention". The

241980

suitable stage for soy was the stage "first three-leaved-spreading leaf". The stage of treatment for the other dicotyledonous plants was the stage "spreading cotyledons, first real leaf in development".

The pots were then sprayed with the spray mixture in an amount corresponding to an application rate (volume) of 500 l / ha and containing the active ingredient in the desired concentration.

The spray mixture was prepared in the same manner as in Example 20.

Depending on the drug concentration of the slurry, the applied drug dose was 0.25 to 4 kg / ha.

The treated pots were then placed in trays in which they were irrigated from below and kept at a temperature of 22 to 24 ° C and at a relative air temperature for 21 days. humidity of 70% were kept.

After / 21 days, the number of live plants in each treated pot was counted and compared with the number of live plants in a pot kept for comparison under the same conditions, but treated with a spray mixture without an active ingredient. In this way, the percentage of plant extermination was determined based on the untreated control pot. A percentage eradication of

24198

100% means that the plant species in question was completely destroyed; a percent kill of 0% means that the number of live plants in the pot treated was equal to the number in the pot provided for control.

The plant species used for these experiments are listed in Table 2. ^.

The results obtained in the application examples a) and b) are summarized in Table 3; this thus includes both the results of the pre-emergence treatment according to application example a), as well as the results of post-emergence treatment according to application example b). In the course of these experiments, it was found that the compounds 0 provided according to the invention were more effective and, above all, more selectively effective than a known compound used for comparison (EU Patents 3 416 and 23 392), which corresponds to the formula V.

Excellent results were also obtained when using the sodium salts of compounds Nos. 4, 5 and 9 (compounds with the group N-Na).

30 c) Application Example a) was repeated by diluting an emulsifiable concentrate with water prepared using xylene as a solvent and containing only 10% active ingredients and 5% surfactant

contained. The amounts of the active ingredients were the same as in the application example a).

241980

d) Application _{Example c} ) was repeated by diluting an emulsifiable concentrate containing 50% active ingredient and 15% surfactant, with the ratio of 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 c) received. In the application, the same results were obtained for the protection of the plants.

e) Application Example _a ) was repeated by diluting an emulsifiable concentrate, which differed from that of the application

15 example a) differed only in that it

241980

Contained 20% surfactant. When applied the same results were obtained for the protection of the plants.

f) Application _{Example c} ) was repeated by successively using different pairs of surfactants in equal amounts; the one agent was ionic, the other agent was nonionic:

a) polyethoxylated hexylbenzene with 40 ethylene oxide units and sodium hexylbenzenesulfonate;

b) polyethoxylated dodecylbenzene with 4 ethylenioxide units and potassium butylbenzenesulfonate;

c) polyethoxylated castor oil and calcium hexanol ·

sulfate; i

'. d) polyethoxylated coconut oil and sodium dodecanol sulfate;

e) polyethoxylated hexanol with '20 ethylene oxide units and sodium dodecylbenzenesulfonate;

f) polyethoxylated styrylphenol with 1-O-1-ethylene oxide units and calcium decylbenzenesulfonate and

g) polyethoxylated tristyrylphenol with 8 ethylene oxide

units and calcium dodecylbenzenesulfonate.

241980

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

g) The procedure was as in Application Example c), 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 Xanthomonas bacteria had been added. One got comparable. Results as in application example a).

h) The procedure was as in Application Example _c ), but replacing the emulsifiable concentrate by a wettable powder containing 6 0% active ingredient, 2% sodium dodecylnaphthalenesulfonate, 2% sodium lignosulfonate, 3% silica as an anti-lumping agent and 13% kaolin.

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

i) The procedure was as in Application Example _c ), but the emulsifiable concentrate replaced by * a wettable powder containing 30% active ingredient, 2% sodium dodecylsulfonate and the rest 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-

241980 6

these agents are useful agents / both in the pre-emergence treatment of crops and in particular soy and cereals, as well as in the post-emergence treatment, especially soy and cereals. In the case of soya, the activity of the compounds according to the invention is of particular interest when the soybean plantings are infested with dicotyledonous weeds such as Indian mallow, Norway spike and purple worm. In the case of cereals, the activity of the compounds is of particular interest when the cereal crops are infested with di'cotyledonous weeds, especially curvaceous grass, recurved foxtail, high ragweed, chrysanthemum, subterranean and labweed.

Tables 1 to 3:

1 4 ι abu

Table (1) _: Compounds of the general formula ι

with W = -CH = X ¹ = Cl

X = CF, X ³ = NO,

Connection no. r ¹ i Fp ⁰ C Yield % 1 CHjCH ₂ -O- 'ISO '76.5 2 ^CH 3V CH ₃ > - ° - 110 85 3 CH ₃ -O- 150 .38 ⁴ (CH ₃ J ₂ N--: .. .-..: .- 73 48. 5 · CH ₃ -NH- 205 27 5 3 9 '' '7 • '192nd · ;. , -  , '4 6 8th , 140. "" 27   9 NH 2 135-140 5 9

Table (1) (continued)

Connection no. R ¹ Fp ⁰ C. , Yield % IQ (Q) -NK- 188 90 11 Cl <g> -NH- 190 84 12 (Q-NH-Cl 190 68 13 O-NH- 183 29.5 14 · MW ¹ H- ^ Π 155 : 34 15 ^ NH- 80 • 79   lfi ' Cl-Qy-NH-- 18Π 87 17 · W " ^NH ~ 65 25.5 '' .18. . ""  -C1-0-KH , 180 72  19 ^c v O) -NH- 185 76.5 '

241380 6

table

crops:

Wheat soy

weeds:

Blackthorn Indian Mallow Blackleaf Ackermann mustard backward curved foxtail Echinochloa crus-galli EC Abutilon theophrasti AT Xanthiuin- pennsylvanicum XP Sinapis arvensis SA

Amaranthus retroflexus AR Ipomea purpurea IP

Connection No. '. {Dosi £ | preemergence

kg / te

EC

95

AT JIP

SA I "XP (S WE j SO

0.25

J 100 1100 .j 90 I 20S

20 J 95 I 100 SLOO I

1.

0.25

0.25

90

80

100

50

90

100

100

20

0.25

0.25

100

100

100

100

80

50

100

100

100

100

100

100 years

20

100

100

100

TOO

100

100

1

100

100

.100

100

100

100

100

100

100

100

ο! ο:

20

60

50 postemergence

EC

60

AT

IP

SA

XP

WE

J 100

100

80 1 100] 100 100

LIlILX

Ιοί 80

80

30

β 100

- 30

100

SO

j 100 j 100 y

.

100

50

'50

100

10Q

90

100

30

90

100

100

100

100

100

100

100

100

100

100

100

100

ϊ {100

100

80

98

30

60

100

100

80

30

100

100

100

100

100

100

100

100

100

100

100

100

100

100

100 '

100

30

table

Connection no.

-

!Dose

10

11

Preemergence.

EC

LiI.

ι.

0.25

• 4

AT

100

ΊοοΊ

80}

IP

SA J XP

ο 1100 i! ο

I Ji

oTiob ϊ ο

WE! SO

0 \ 0

"TTI"

ϊ

60

30

0.25

0.25

  0 ', 20

100

30

0.25 Γ Ό

90

30

100

100

100

100

100

0 8,100

100

oil ο!

postemergence

30

ο f

o i ο! ο I ο

80

80

30

30

100

100

98 -j - j-

100

30

100

100

100

olo

98

100 3100

100

100 AT

IP

100

Q ) 100

30

30

30

100

100

SA

XP

WE

100 UOO S

100-y

90

100

80

80

100

100

30

100

100

100

100

100

100

50

100

100

100

0 year

100

100

100

100 I100

100

80 years

100

100

100

100

100

100

100

100 '

so

Connection no.

O [80 I 80 j 100 j 0

Table (3) (continued)

Compound No. | kg / hj { ^{pre-emergence}

1719

EC AT IP! SA XP

50 ¹ J 100 JO 0

24 1980

formula sheet

R is CO-N-SO ₂ -R ¹

(U

scheme (I) χ ¹ / / CO-Cl R- acid ^ Λ > -X ³ 'H Χ ² _ P -NH-SO , R ¹

2 ^χ ^, p

aJczeptor

CO-N-SO ₂ -R

+ HCl

(D

/ 2

-Z

Scheme (II)

COOH

2 J \ _o / \ _X 3

(ID

X + Cl-SO., -

X ¹ CO-NH-SO ₀ Cl

/ / c

+ co.

(III)

AAnn

X / CO-NH-SO ₂ Cl

JT \ - 3 1 1

0 Λ Γ X + RH (or 2 R Hin Ab-

(III)

Entity of an acid acceptor)

Acid-X acceptor

CO-NH-SO ₂ -R

+ HCl

Compounds of the general formula (I) in which R = H

-έπο

241380

schema Ulli (~ sond.rerF.il of the scheme, H) V

 + 3 MOH (M 4 = H)

(III)

-O-

O -

+ MCl

(IV)

NO,

(I A)

CO-NH-SO ₂ -CH ₃

(V)

Claims (12)

He is entitled to claim 1. A herbicidal composition containing an active ingredient combined with at least one inert agriculturally acceptable carrier, g e kennz eichnet characterized in that the active ingredient is a Phenoxybenzoesäurederivat of the general formula I, in the W is a group -CH = - or -CX = or the nitrogen atom. -N =, 0 - 12 3 4
X, X, X and X "each represent a halogen atom, in particular F, Cl or Br or a polyhaloalkyl group such as CF-, NO ₉ , CN, an alkyl, alkoxy, alkylsulfonyl, sulfonamide, Nitroso or alkyl carboxylate group, M 3 1 12, x-R R is a group -OM or -N-COR or -N ₄ or -XR ^D means ^R M is a hydrogen atom or an agriculturally acceptable cation, for example an alkali metal cation or; optionally substituted ammonium cation, -X- 3 * 241 X = O or S, R and R represent an optionally substituted hydrocarbon or heterocyclic group, 3 4 2 R and R have one of the meanings given for R, and furthermore represent a hydrogen atom or if they represent an alkoxy group, or together they can form a single divalent optionally substituted hydrocarbon group, R has one of the meanings given for M and. Can also be an alkyl group having 1 to 4 carbon atoms. 2. Means according to item 1, g e k, e η η characterized in that the alkyl or 'alkoxy contained in the formula I of the active ingredient. 0 radicals have 1 to 4 carbon atoms and / or 2 p
R and. R 1 to 12 carbon atoms. 3. Means according to item 1 or 2, g e characterized in that in formula I 25 of the active ingredient R, R, R and R are each one Alkyl group which optionally has a maximum of 4 substituents, such as an aryl group, · in particular diphenyl group, a chlorine or bromine atom, an OH group, alkoxy group, SH, 0 alkylthio, carboxyl, alkylcarboxylate or cyano group; also an alkenyl or alkynyl group of 2 to 6 carbon atoms. an aryl group, in particular the phenyl group, optionally substituted by a maximum of 4. 3 5 substituents, such as Cl, 3r, an alkyl, cyano, 24 198 0 Carboxyl, alky! Carboxylate, NO ₂ , OH, alkoxy, -SH, alkylthio, with the various alkyl or alkoxy groups which have been cited as substituents each having 1 to 4 carbon atoms. 4. Means according to one of the items 1 to '3, gekennz eich net characterized in that in the formula I of the active ingredient X ¹ = Cl, X ² = CF, Vi is -CH =, X = Cl or NO ₂ and R is a hydrogen or sodium atom. 5. Composition according to one of the items 1 to 4, characterized in that in the formula I of the active ingredient R is -NH-R. 6. Composition according to one of the items 1 to 5, g ek enn e chenn et by virtue of that it contains 0.05 to 95 wt .-% of active ingredient. 7. Composition according to one of the items 1 to 6, characterized eic.hnet in that it is liquid and 10 to 8 0 wt .-% of active ingredient contains. , 8. Means according to any one of items 1 to 6, characterized in that it is solid and contains from 0 to 80% active ingredient. 9. A composition according to any one of items 1 to 8, characterized chnet by containing 0.1 to 20% surfactant. 24 198 0 10. Application of the agent according to one of the items 1 to 9 in soy plantations after emergence or before emergence of the plants. 11. Use of the agent according to any one of items 1 to 9 in cereal crops which are or may be infested with at least one dicotyledonous weed, such as Indian mallow, Norway spike and purple winds.
10 12. Application of the agent according to one of items 1 to 9 in an amount corresponding to 0.1 to 2 kg / ha of active compound of the general formula I. For this 3 leaves formulas