NL8202974A - HERBICIDE COMPOUNDS DERIVED FROM PHENOXYBENZOIC ACID AND THE METHODS OF PREPARING AND USING IT. - Google Patents

Description

ir-. 4 "· 1 - v £

Herbicidal Compounds Derived From Phenoxybenzoic Acid And Its Methods For Its Preparation And Use.

The invention relates to new selective herbicides from the phenoxybenzoic acid family, to an preparation for their preparation and to their use.

Various herbicidal derivatives of acifluoro-5-phene, also referred to as 5- /, 2-chloro (trifluoromethyl) phenoxy / 2-nitrobenzoic acid, and its salts, and in particular derivatives of the type consisting of alkyl cycloalkyl, thioalkyl and phenyl esters and acid amides or chlorides are known. Such compounds are described in U.S. Pat. Nos. 3,652,6it5, 3,778,635, 3,873,302, 3,983,168, 3,907,866, 3,798,276, 3,928.U16, and U.063,929.

An object of the invention is to provide new herbicidal compounds. In fact, it is desirable to have the greatest number of herbicides from the family in question available to be able to solve the maximum number of potential weed destruction problems.

The invention therefore relates to compounds of the formula 1, wherein W is a group -CH = or -CX ^ = or the nitrogen atom, -N =; X ^, Xg, X ^ and a halogen atom, especially fluorine, chlorine and bromine; a polyhaloalkyl group, such as CF 4; Yet; CN; or an alkyl, alkoxy, alkylsulfonyl, sulfonamide, nitroso, or alkylcarboxylate radical, wherein the various alkyl or alkoxy groups mentioned above usually have 1-¾ carbon atoms; a group -OM, 25 M / », -N-COR ^, -N or -X-Rc; M a hydrogen atom or a cation acceptable in agriculture, such as an alkali metal cation, in particular a sodium cation, or an unsubstituted or substituted ammonium cation; X is 0 or S; R 9 and R 8 represent a substituted or unsubstituted hydrocarbyl group, such as alkyl or aryl group 8202974-2s or a heterocyclic group preferably having 1-12 carbon atoms; R 1 and have given one of the meanings for R 8 and may also represent hydrogen whether an alkoxy residue, or together may form a single optionally substituted carbohydrate hydrocarbon residue; and Reen has given the meanings for M and may also be an alkyl group having 1-¾ carbon atoms.

More precisely, Rg j., Which may be the same or different, may represent an alkyl group having 1-¾ carbon-10 atoms, which is substituted by up to four substituents, such as an aryl group (especially a phenyl group), a chlorine or bromine atom or a hydroxyl, alkoxy, SH, alkylthio, carboxyl, alkyl carboxylate or cyano group; an alkenyl or alkynyl group preferably having from 2 to 6 carbon atoms; or an aryl group, especially a phenyl group, optionally substituted by up to four substituents, such as chlorine, bromine or an alkyl, cyano, carboxyl, alkyl carboxylate, NO5, OH, alkoxy, SH or alkylthio group, in addition to the various alkyl or alkoxy groups mentioned above as substituents, preferably have 1-¾ carbon-20 atoms; R 1 and R 2 may also represent hydrogen or together form an alkylene radical, preferably with carbon atoms.

The preferred subfamily of the compounds of the formula 1 is represented by the compounds, wherein the chlorine atom, Xg e CF ^, X ^ = Cl or preferably NOg, W is the group -CH = and R has the same meaning as M.

The compounds where hydrogen is hydrogen are also preferred.

The invention also relates to the inventions for preparing the products according to the invention.

These selections consist of carrying out a chemical reaction according to one of the reaction schemes on the formula sheet, in which the various symbols have the meanings indicated previously, unless stated otherwise.

In the procedure of reaction scheme B, the first stage is a product of the formula 2 to be reacted with 8202974 ............ δ ί - 3 - chlorosulfonyl isocyanate in a solvent or in a large excess of this chlorosulfonyl isocyanate. The temperature is generally 20-100 ° C, preferably 100-80 ° C. The concentration of the products of formulas 2 and 3 is generally between 5-70 ° C. When a solvent is used, it can be, for example, an optionally halogenated aliphatic or aromatic hydrocarbon, in particular toluene, or a nitrile or an ether.

The reaction of the compound of the formula III with the product of the formula R1H is generally carried out between -1 ° 0 ° C and + 60 ° C, preferably between -20 ° C and + 30 ° C C. The solvents that can be used are the same as those of the previous reaction step. The concentration of the products of formulas 3 and 1 is generally between 5-50 ¢. The reaction is advantageously carried out in the presence of tertiary amines, in particular triethylamine and pyridine; instead of a conventional acid acceptor, it is possible to use the compound R H itself, which is then present in a very much greater amount than that commonly used, if it is simply a reagent.

The invention will now be illustrated in a non-limiting manner with the following examples.

Examples I-XIX

18.1 g of acifluorphene are added to 20 ml of chlorosulfonyl isocyanate and the reaction mixture is then gradually warmed to 50 ° C with stirring until the release of hydrogen chloride gas ceases. The mixture is cooled, 50 ml of hexane is added and the precipitate is filtered off, solid with hexane and dried in vacuo. 22.2 g of 5- / 2-chloro- (trifluoromethyl) phenoxy / 2-nitro-N-chlorosulfonyl-benzamide are obtained, which is dissolved in 100 ml of aceto-nitrile. The solution is stirred and cooled to 0 ° C, and a solution of g of dimethylamine in 20 ml of acetonitrile is added dropwise. The reaction medium is then allowed to come to 20 ° C for a long time and stirring is continued for 1 hour at this temperature. The acetonitrile is evaporated and the residue is dissolved in chloroform. This chloroform solution is fixed with water, dried and concentrated and the residue is purified and purified by chromatography on silica, chloroform being used as the eluent. This gives 10.8 g of the compound No. * 4 of the formula.

The different compounds Nos. 1-19 are prepared in the same medium, replacing the dimethylamine with the corresponding amine or alcohol. The formulas and physical properties of these products are summarized in Table A.

Example XX

Herbicide application in the pre-germination treatment of plant-10 species.

A number of seeds are sown in pots of 9 x 9 x 9 cm filled with light agricultural soil, the number of seeds being determined as a function of the plant species and the size of the seed.

The pots are treated by spraying with an amount of spray mixture corresponding to a volumetric application dose of 500 l / ha and contain the active ingredient at the desired concentration.

Treatment with the spray mixture is therefore carried out on seeds which are not covered with soil (the term "spray mixture" generally refers to the preparations which are diluted with water as they are applied to the plants).

The spray mixture used for the treatment is an aqueous suspension of the active ingredient, containing 0.1% # Cemulsol NP10 (a surfactant consisting of an ethylene oxide / alkyl phenol condensate, mainly a 10: 1 ethylene oxide / nonyl phenol condensate) and 0.0 * 1 wt% Tween 20 (a surfactant consisting of the laurate of an ethylene oxide / sorbitol condensate).

This suspension is obtained by mixing and grinding the ingredients in a mill to obtain an average particle size of less than 40 microns.

According to the concentration of active ingredient 8202974 S i - 5 - in the spray mixture, the applied dose of active ingredient is 0.25-¾ kg / ha.

After treatment, the seeds are covered with an approximately 3 mm thick layer of soil.

The pots are then placed in trays, which are intended to receive the humidification water by sub-irrigation and are kept at a temperature of 22-2¾0 C and 70% relative humidity for 21 days.

After 21 days, the number of live plants in the pots is treated with a spray mixture containing the active ingredient to be tested, and the number of live plants in a bianco pot is treated under the same conditions, but by means of a spray mixture, which is not an active ingredient contains, counted. The percentage destruction of the treated plants with respect to the untreated bianco is thus determined. A percentage destruction equal to 100% indicates that there is complete destruction of the plant species in question and a percentage of 0% indicates that the number of live plants in the treated pot is equal to that in the bianco pot.

Example XXI

Herbicide application in the post-germination treatment of plant species and.

A number of seeds are sown in 9 x 9 x 25 cm pots filled with light agricultural soil, the number of which is determined as a function of the plant species and the size of the seed.

The seeds are then covered with an approximately 3 mm thick layer of soil and the seed is allowed to germinate until it has developed a plant in the appropriate development phase.

The treatment phase for the grassy plants is the "second leaf formation" phase. The appropriate phase for soy is the "first triple leaf open" phase. The treatment phase for the other dicotyledons is the "cotyledons open, first true leaf developed" phase.

The pots are then treated by spraying 8202974 * s * - 6 - with an amount of spray mixture corresponding to a volumetric application dose of 500 l / ha and containing the active ingredient in the desired concentration.

The spray mixture is prepared in the same manner as in Example XX.

According to the concentration of active ingredient in the spray mixture, the applied dose of active ingredient is 0.25-1 * kg / ha.

The treated pots are then placed in 10 trays, which are intended to receive the humidifier by sub-irrigation, and kept at a temperature of 22-200C and a relative humidity of 70% for 21 days.

After 21 days, the number of live plants in the pots is treated with the spray mixture, which contains the active ingredient to be tested, and the number of live plants in a bianco pot is treated under the same conditions, but by means of a spray mixture, which is not an active ingredient. contains, counted. The percentage destruction of the treated plants, with respect to the untreated bianco, is thus determined.

20 A percentage of destruction equal to 100% indicates that there has been complete destruction of the plant species in cultivation, and a percentage of 0% indicates that the number of live plants in the treated pot is equal to that in the bianco pot .

The plant species for which the herbicidal application is applied are shown in Table B.

The results obtained in Examples XX and XXI are shown in Table C, enter the pre-germination results of Example XX when the post-germination results of Example XXI are collected. In the course of these tests it is possible to take advantage of improved behavioral properties (in particular the selectivity) compared to a product representative of the prior art (European patents 3.1 * 16 and 23,392) and that the formula 6 has. EXAMPLE XXI-bis 35 Excellent herbicidal results are also obtained 8202974 v - 7 - using the sodium salts (compounds containing the N-Na group) of compounds Nos. 5 and 9 ·

The tests carried out therefore demonstrate the remarkably advantageous properties of the compounds of the invention, so much when used for the pre-germination treatment of crops, more particularly of soy, as for the post-germination treatment, especially of soy and grains, including corn. In the case of soy, the activity of the compounds is particularly advantageous when this crop is infected with bilobed seeds, such as mallow, burdock and day flower. The products of the invention show an improved selectivity compared to the reference product.

In practice, the compounds of the invention are rarely used alone. Usually these compounds are part of preparations. These preparations, which can be used as herbicides, contain as active ingredient a compound according to the invention, as described above in combination with solid or liquid carriers, which are acceptable in agriculture and surfactants, which are also acceptable are 20 in agriculture. In particular, the usual inert carriers and the usual surfactants can be used. These preparations are also part of the invention.

These preparations may also contain all kinds of other ingredients, such as, for example, protective colloids, adhesives, thickeners, thixotropic agents, penetrants, stabilizers, sequestrants and the like, as well as other known active ingredients with pesticidal properties (in particular insecticide, fungicide or herbicide properties), properties that promote plant growth (especially fertilizers) or properties that control plant growth.

More generally, the compounds used in accordance with the invention can be combined with any of the solid or liquid additives, which are consistent with conventional formulation techniques.

The doses of the compounds according to 8202974 used

- V

The invention can vary within wide limits, in particular according to the nature of the plants to be removed and the usual degree of infection of the crops by these future plants.

Generally, the compositions of the invention usually contain 0.05-95 wt% of one or more active ingredients of the invention, 1-95% of one or more solid or liquid carriers and, if appropriate, 0 , 1-20% of one or more surfactants.

In accordance with what has already been said, the compounds of the invention are generally combined with carriers and, where appropriate, surfactants.

In the present description, the term "carrier" is understood to mean an organic or inorganic, natural or synthetic material, with which the active ingredient is combined to facilitate its application to the plant, to seeds or to the soil. This carrier is therefore generally inert and should be acceptable in agriculture, especially on the treated plants. The carrier may be solid (clays, natural or synthetic silicates, silicon oxide, resins, solids, solid fertilizers and the like, or liquid (water, alcohols, especially butanol, esters, especially methyl glycol acetate, ketones, especially cyclohexanone and isophorone, petroleum fractions, aromatic hydrocarbons, especially xylenes, or paraffinic hydrocarbons, aliphatic chlorohydrocarbons, especially trichloroethane, or aromatic chlorohydrocarbons, especially chlorobenzenes, water-soluble solvents, such as dimethylformamide, dimethyl sulfoxide, , liquefied gases and the like).

The surfactant can be an emulsion, dispersion or wetting agent of the ionic or non-ionic type or a mixture of such surfactants. Examples that may be mentioned are salts of polyacrylic acids, salts of lignosulfonic acids, salts of 8202974

V

- 9 - phenylsulfone or naphthalene sulfonic acids, polycondensates of ethylene oxide with fatty alcohols, fatty acids or fatty acid amines, substituted phenols (in particular alkyl phenols or aryl phenols), salts of sulfosuccinic esters, taurine derivatives (in the particular 5 alkyl esters of condensates of phosphates of phosphates) of ethylene oxide with alcohols or phenols, fatty acid esters of polyols, and derivatives of the above compounds containing sulfate, sulfonate and phosphate groups. The presence of at least one surfactant is generally essential if the active ingredient and / or the inert carrier are insoluble in water and if the application agent is water.

For their use, the compounds of the formula I are therefore generally in the form of preparations; these compositions of the invention are themselves in a relatively wide variety of solid or liquid forms.

As forms of solid preparations can be mentioned spraying powders (with a content of compound of the formula 1, which can go up to 100 #) and granules, in particular those obtained by extrusion, by compression, by impregnation of a granular carrier or by the formation of granules from a powder (the compound content of the formula 1 in these granules is between 0.5-80% for the latter cases).

The solid preparations usually contain 20-80% active ingredient.

As forms of liquid preparations or preparations to be diluted into liquid compositions upon application, solutions can be mentioned, in particular emulsifiable concentrates, emulsions, suspension concentrates,. aerosols, wettable powders, or scattering powders, dry flowables and pastes.

The liquid preparations usually contain 10-80% active ingredient.

The emulsifiable or soluble concentrates usually contain 10-80% active ingredient, and the emulsions or solutions ready for application contain 0.01-20% active ingredient. In addition to the solvent, the emulsifiable 8202974-10 concentrates may contain 2-20%, if necessary, suitable additives such as stabilizers, surfactants, penetrants, corrosion inhibitors, dyes and adhesives.

Starting from these concentrates, emulsions or solutions of any desired concentration, which is particularly suitable for application to the plants, can be obtained by dilution with water.

The compositions of some emulsifiable concentrates will now be given as examples: 10 Active ingredient 250 g

Ethylene oxide / alkyl phenyl condensate 30 g

Calcium alkylaryl sulfonate 50 g

Petroleum distillate fraction distilling at 160-185 ° C 670 g 15 Another preparation is:

Active ingredient 350 g

Ethylene oxide / castor oil condensate 6θ g

Sodium alkylaryl sulfonate Uo g

Cyclohexanone 150 g 20 Xylene ^ 00 g

Another preparation is:

Active ingredient 1 * 00 g

Ethylene oxide / alkyl phenol condensate 100 g

Ethylene glycol methyl ether 250 g 25 Aromatic petroleum fraction which distills at 160-185 ° C 250 g

Another preparation is:

Active ingredient HOO g

Phosphate of ethylene oxide / tristyryl-30 phenol condensate 50 g

Phosphate of ethylene oxide / alkyl phenol condensate 65 g

Sodium alkyl benzene sulfonate 35 g

Cyclohexanone 300 g 35 Aromatic petroleum fraction, which distills at 160—185 ° C ----------- - 150 g 8202974 - 11 -

Another preparation is:

Active ingredient UOO g / l alkali metal dodecylbenzene sulfonate 2k g / l 10: 1 Ethylene oxide / nonylphenol condensate 16 g / l 5 Cyclohexanone 200 g / l

Aromatic solvent made up to 1 1

Another preparation of an emulsifiable concentrate is:

Active ingredient 250 g

Epoxidized vegetable oil 25 g 10 Mixture of an alkyl aryl sulfonate and a polyglycol ether of fatty acid alcohols 100 g

Dimethylformamide 50 g

Xylene 575 g 15 The suspension concentrates, which can be applied by spraying, are prepared to give a stable flux which does not deposit (finely grind) and they usually contain 10-75% active ingredient, 0.5 -15% surfactants, 0.1-10% thixotropic agents, 0-10% suitable additives, such as anti-foaming agents, corrosion inhibitors, stabilizers, penetrating agents and adhesives, and as carrier water or an organic liquid, in which the active ingredient is poorly soluble or insoluble; certain organic solids or inorganic salts can be dissolved in the carrier to help prevent deposits or to act as antifreeze for the water.

A composition of a suspension concentrate will now be given as an example:

Active ingredient 50 g 30 Phosphate of ethylene oxide / tristyrylphenol condensate 50 g

Ethylene oxide / alkyl phenol condensate 50 g

Sodium polycarboxylate 20 g

Ethylene glycol 50 g 35 Organopolysiloxan oil (anti-foaming agent) 1 g 8202974 * s.

- 12 -

Polysaccharide 12.5 g

Water 316.5 g (The wettable powders (or sprays) are conventionally prepared to contain 20-95% active ingredients, and they typically contain 0-5% of a wetting agent in addition to the solid carrier, 3-10 % of a dispersant and, if necessary, 0-10% of one or more stabilizers and / or other additives, such as penetrants, adhesives, anti-caking agents, dyes and the like.

10 Different compositions of wettable powders will now be given as examples:

Active ingredient 50%

Calciuxnignosulfonate (flocculant) 5%

Isopropylnaphthalene snlphonate (anionic wetting agent) 1%

Kaolin (filler) 39%

Kiet / ^ bkend silica 5%

Another example of a wettable powder, this time of 80% strength, is: 20 Active ingredient 80%

Sodium alkyl naphthalene sulfonate 2%

Sodium lignosulfonate 2%

Ko,. . . .

· * - Nxet ^ counting silicon oxide 3 5 *

Kaolin 13% 25 Another example of a wettable powder is:

Active ingredient 50%

Sodium alkyl naphthalene sulfonate 2%

Low viscosity methyl cellulose 2%

Diatomaceous earth k6% 30 Another example of a wettable powder is:

Active ingredient 90%

Sodium dioctyl sulfosuccinate 0.2%

Synthetic silicon oxide 9j8%

Another composition of a spray powder, this time of U0% 35 strength, is: 8202974 - 13 -

Active ingredient ^ 00 g

Sodium lignosulfonate 50 g

Sodium dibutylnaphthalene sulfonate 10 g

Silicon oxide 5 ^ 0 g 5 Another spray powder now of 25% is:

Active ingredient 250 g

Isooctylphenoxy-polyoxyethylene ethanol 25 g

Mixture by weight parts of Champagne lime and hydroxyethyl cellulose 17 g 10 Sodium aluminosilicate 5 ^ 3 g

Kieselguhr 165 g

Another spray powder, now of 10% is:

Active ingredient 100 g

Mixture of sodium salts of saturated fatty acid sulfates 30 g

Naphthalene sulfonic acid / formaldehyde condensate 50 g

Kaolin 820 g

To obtain these spray powders or wettable powders, the active ingredients are thoroughly mixed with the further materials in suitable mixers, or the porous filler is impregnated with the molten active ingredient, and the mixture is ground in mills or other suitable pulverizers. This gives spray powders of advantageous wettability and suspensibility; they can be suspended in water at any desired concentration and this suspension can be used very advantageously, especially for application to the leaves of plants.

The dry flowables (more precisely these granules, which are readily dispersible in water) have a composition substantially equal to that of the wettable powders. They can be prepared by forming granules from preparations described for the wettable powders, either by a wet process (contacting the finely divided active ingredient with the inert filler and with a small amount of water, for example, 8202974 - 1¼). 1-20%, or an aqueous solution of dispersant or binder, followed by drying and sieving) or by a drying process (compression, followed by grinding and sieving).

A dry flowable fabric recipe will now be given as an example:

Active ingredient 800 g

Sodium alkyl naphthalene sulfonate 20 g

Methylene bis (sodium naphthalene sulfonate) 80 g

Kaolin 100 g 10 Instead of the wettable powders, it is possible to produce pastes. The conditions and methods of production and use of these pastes are the same as those of the wettable powders or spray powders.

As already mentioned, the aqueous dispersions and emulsions, for example compositions obtained by dilution with water, a wettable powder or an emulsifiable concentrate according to the invention, fall within the general scope of the compositions which can be used according to the invention. The emulsions can be of the water-in-oil or oil-in-water type and they can have a thick consistency, such as "mayonnaise".

All these aqueous dispersions or emulsions, or spray mixtures, can be applied to the crops in which weeds are to be controlled, in any suitable manner, mainly by spraying, in doses generally of the order of 100-1200 L spray mixture per ha.

The granules intended to be applied to the soil are usually manufactured such that they have dimensions between 0.1-2 mm and they can be manufactured by agglomeration or impregnation. Preferably, the granules contain 1-25% active ingredient and 0-10% additives such as stabilizers, slow release modifiers, binders and solvents.

An example of the composition of grains 35 is: 8202974 - 15 -

Active ingredient 50 g

Propylene glycol 25 g KLei (particle size 0.3-0.8 mm) 925 g

As indicated, the invention also relates to a method of destroying weeds in crops, in particular cereals such as wheat and also corn and soy, in which methods an effective amount which is not toxic to the crop in question apply at least one of the compounds of the invention to the plants and / or to the soil in the zone in which weeds are to be destroyed. In practice, these compounds are used in the form of herbicidal compositions of the invention previously described. In general, amounts of active ingredient of 0.01-5 kg / ha, preferably 0.1-2 kg / ha give good results, it being clear that the choice of the amount of active ingredient to be used depends on the severity of the problem to be solved, the climatic conditions and the crop in question.

The treatment can be carried out either as a pre-germination treatment of the crops and future plants, or as a pre-sowing treatment of the crops with incorporation into the soil (this incorporation is therefore a complementary operation in the treatment process according to the invention) or as a post-germination treatment. Other embodiments of the treatment method of the invention may also be used. For example, it is possible to apply the active ingredient to the soil with or without uptake before a crop is planted.

The treatment method of the invention is applicable both in the case of annual and perennial crops. In the latter case, it is preferable to apply the active ingredients according to the invention in a local manner, for instance between the rows of said crops.

35 8202974 - 16 -

TABLE A: products of the formula J

Connection R1 Mp. in ° C Yield ncK ____________________________ 1 CH3-CH2-0- 150 76.5% 2 CH3 \ CH / CH-0- 110 85% 3 CH3-0- 150 38% (CH3) 2N- 73 It8% 5 CH3-NH - 205 27% 6 [^ N- 39% - O- 192 k6% y och3 8 1U0 27%

Nch3 9 NH2 135-1 ^ 0 59% 10 ^ -NH- 188 90% 11 Cl- ^ j ^ —NH- 190 8k l 12 190 68%

Cl 13 <$> - NH- 183 29.5%

Cl A C "- 155 t 3 ^% 15 ClvCl 80 79% 16 01 ciXjVm- 180 87% 17 (Λ-ηη- 65 25.5% ci - * - '18 Cl - ^ - NH- 180 72%

Cl> _.

19 (yaym- 185 76.5%

Cl * · * - '8202974 - 17 -

TABLE B

Name Latin name Abbreviation

Tarve WHE

Case ".

Soy

bean SOY

fHanepoot Echinochloa crus-galli ECH

Mallow Abutilon theophrasti ABU

On-Burdock Xanthium pennsylvanicum XAN

herb Wild Sinapis arvensis SIN

mustard

Katte- Amaranthus retroflexus PW

tail

Dayflower Ipomea purpurea IPO

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Claims (14)

A compound derived from phenoxybenzoic acid of the formula 1, wherein W is a group -CH = or -CX ^ = or the silent atom, -N =; Xj, Xg, Xl and Xl a halogen atom, in particular F, Cl and Br; a polyhaloalkyl group, such as CF 4; NOg, CN, or an alkyl, alkoxy, alkylsulfonyl, sulfonamide, nitroso, or alkyl carboxylate moiety; a group ? / R 3 -O M, -N-CORg, -N or -X-Rtj M a hydrogen atom or a 10 'cation acceptable in agriculture, such as an alkali metal cation, or an unsubstituted or substituted ammonium cation; X is 0 or S; Rg and Rc represent a substituted or unsubstituted hydrocarbyl group or a heterocyclic group, Rg and Rc have one of the meanings indicated for R and may also represent the hydrogen atom or an alkoxy radical, or together form a single optionally substituted divalent hydrocarbon radical and R has given one of the meanings for M and may also be an alkyl group with 1 to 1 carbon atoms. A compound according to claim 1, characterized in that the alkyl or alkoxy radicals contained therein have 1-U carbon atoms and / or wherein Rg and R 1 have 1-12 carbon atoms. Compound according to either of Claims 1 and 2, characterized in that Rg, Rl, Rl and Rj. represent an alkyl group substituted or unsubstituted by up to four substituents such as an aryl group (especially a phenyl group), a chlorine or bromine atom or a hydroxyl, alkoxy, SH, alkylthio, carboxyl, alkylcarboxylate or cyano group, an alkenyl or alkynyl group, preferably with 2-6 carbon atoms; or an aryl group, especially a phenyl group, which is optionally substituted by up to four substituents, such as Cl, Br or an alkyl, cyano, carboxyl, alkyl carboxylate, NOg, OH, alkoxy, SH or alkylthio group, with the various above as substituents said alkyl or alkoxy groups preferably have 1-4 carbon atoms. Compound according to any one of claims 1-3, 8202974> ϊ-22 - characterized in that chlorine is, Xg is CF ^, W is -CH =, chlorine or NOg, and R is a hydrogen or sodium atom. Compound according to any one of claims 1-H, characterized in that it is -NH-R 4. 5 · 6. Process for preparing a compound according to any one of claims 1 to 5, characterized in that an acid of the formula 2 is reacted with chlorosulfonyl isocyanate to a product of the formula 3, which is reacted with a compound of the formula R1. H, it being possible for the various symbols used in these formulas to have the meanings indicated in claims 1-5. 7. Process according to claim 6, characterized in that the first step is carried out at 20-100 ° C in a solvent and with a concentration of products of formulas 2 and 15 between 5-70%. .%. 8. Process according to claim 6 or 7, characterized in that the second stage of the reaction is carried out between -k0 ° C and + 60 ° C in a solvent and with a concentration of products of formulas 3 and 1 between 5-50% by weight. Herbicidal composition, characterized in that it contains as active ingredient a compound according to any one of claims 1 to 5, in combination with at least one inert carrier, which is acceptable in agriculture. 10. A composition according to claim 9, characterized in that it contains 0.05-95% active ingredient. Preparation according to any one of claims 9-10, characterized in that it is liquid and contains 10-80% active ingredients. 12. A composition according to any one of claims 9 or 30, characterized in that it is solid and contains 20-80% active ingredients. Preparation according to any one of claims 9-12, characterized in that it contains 0.1-20% surfactant. 1¾. Method of destroying weeds between crops, characterized in that an effective non-plant toxic amount of a preparation according to any one of claims 9-13 is used. 15. A method according to claim 1H, characterized in that the preparation is applied to a soy crop as a post-germination or pre-germination treatment. Method according to claim 1U, characterized in that the crop is an agricultural crop which is infected or which is susceptible to infection by at least a two-lobed weed, such as mallow, burdock and day flower. 17. Process according to any one of claims 11-16, characterized in that the compound of the formula I is used in an amount of 0.1-2 kg / ha. 15 8202974