LU84301A1 - HERBICIDE COMPOUNDS DERIVED FROM PHENOXYBENZOIC ACIDS AND PROCESSES FOR THEIR PREPARATION AND USE - Google Patents

Description

*. *. 1

The present invention relates to novel selective herbicides of the phpnoxybenzoic acid family as well as their preparation process and their application.

We know various herbicidal derivatives of acifluor-fen, also called 5-j ^ 2-chloro-A- (trifluorom ^ thyl) ph ^ noxyJ-2-nitrobenzoic acid, and its salts, and in particular * d ^ riv ^ s of esters of alkyl, cycloalkyl, thioal-kyie, phenyl and acid amides or chlorides. Such composites are described in US patents US 3652645, 3784635, 3873302, 3983168, 3907866 ,. 3798276, 3928416, 4063929.

In this presentation, the chemical compounds are designated by their name expressed according to the French nomenclature; however the figures indicating the position of the substituents are placed before the relevant substituent following the Anglo-Saxon nomenclature. .

An object of the present invention is to provide new herbicidal compounds. It is in fact desirable to have the greatest possible number of herbicides in the family in question so as to be able to resolve the maximum number of possible cases of weed control.

The present invention therefore relates to compounds of formula *

R

X CO - N - S02 ”in which: - W is a group -CH = or -CX ^ = or the nitrogen atom -N =, - X ^, X2, X ^, X4 represent a halogen atom , especially F, Cl and Br; a polyhaloalkyl group such as CF ^; NO2, CN; an alkyl, alkoxyl, alkylsulfonyl, sulfonamide, nitroso, alkyl carboxylate radical; the various above-mentioned alkyl or alkoxyl groups having the most (r t 2 * \ often 1 to A carbon atoms, m 1 "2 ^ - R represents a group -0M or -N-COR or -N ^ ^ or

-X-R5 R

- M represents a hydrogen atom or an acceptable cation: in agriculture such as an alkali metal cation, in particular: sodium, or an ammonium cation, substituted or not.

- X is 0 or S, 2 5 - R and R represent a hydrocarbyl group, in particular aryl, or alkyl, or heterocyclic, substituted or not, | preferably having from 1 to 12 carbon atoms, I 3 δ, | 3 - R and R have one of the meanings given for R ^, and may further represent the hydrogen atom, or an alkoxyl radical or form together a single divalent hydrocarbon radical, ever substituted, - R a one of the meanings given for M and can also represent an alkyl group having from 1 to 4 carbon atoms. ''

More precisely, R ^, R "5, R ^ and R ^, which may be identical or different, may represent an alkyl group, preferably having from 1 to 4 carbon atoms and substituted by a maximum of 4 substituents such as an aryl group (particularly phenyl ), a chlorine or bromine atom, a hydroxyl, alkoxyl, SH, alkylthio, carboxyl, alkyl carboxylate group, cyano; an alkenyl or alkynyl group preferably having from 2 to 6 carbon atoms; an aryl group, particularly phenyl, optionally substituted With a maximum of 4 substituents such as Cl, Br, an alkyl, cyano, carboxyl, alkyl carboxylate, NO2, OH, alkoxyl, I SH, alkylthio, the various alkyl or alkoxyl groups mentioned. , · Born above as substituents preferably having from 1 to 4 carbon atoms 3 4 - R and R can also represent the hydrogen atom I or together constitute an alkylene radical having preferably ~! Rence 4 or 3 carbon atoms.

j A preferred subfamily among the compounds of for- | mule (I) is represented by the compounds such that is I ίίΛ jf 3 the chlorine atom, X2 is CF ^, is Cl or preferably ^ NCL, w is -CH = and R has the same meaning that Mr.

Z ^ _

One composes cheerfully the composites where R is the hydrogen atom.

The invention cheerfully relates to the processes for preparing the products according to the invention.

These procedures include the implementation of a chemical reaction according to one or other of the following reaction schemes, in which, unless otherwise indicated,. the various symbols have the meanings indicated above. ' high.

: Diagram (I)

Xl CO-C1 Χ97Λο / Λ_χ, + R-NH-SQoR1 acceptor V- / vv 3 2,

S

formula (II)

K

• co-n-so2-rx * ^ "Cy · ° '{^ y x3 + hci Λ formula (I)

Diagram (II)

Χχ COOH

X2 X3 + C1 S02 "N == C = O -> formula (II) x1 co-kh-so2ci - * Xs + c ° 2 formula (III) then X. C0-NH-S0oCl / 1/2 Y - ( Ψ \ - π - (V0 V- v JL T »1 TT / ___« 1 - -. · ”2 \ 'rf ~ \ 1 /“ 3' * v ~ 11 ^ xv - n eu j. Dosence '- ” '-' acid acceptor), formula (III), 4 t. ·. · · Χ CO-NH-SO ^ I ^

Compounds of formula (I) in which R is the hydrogen atom Scheme (III) (special case of scheme (II)) χχ CO - NH - S02C1 X „_ /" v \ -0 -ΛΛ- x- > + 3M0H (M being other had the atom 2 - \ JJ- 3 of hydrogen) '

formula (III) M

X'- CO - N - S02-0M

Formula (IV)

Λ X

NOT

S

X

y __5_ s.

In the process applying the reaction scheme (II), one therefore begins by reacting a product of formula (II) with chlorosulfonylisocyanate in a solvent or in a large excess of this chlorosulfonylisocyanate. The temperature is generally between 20 and 100 ° C, preferably between 40 and 80 ° C; the concentration of products of formulas (II) and (III) is generally between 5 and 70% by weight. When a solvent is used, it may for example be an aliphatic or aromatic hydrocarbon, optionally halogenated, in particular toluene, or a nitrile or an ether.

The reaction between compound of formula (III) and the "product of formula R ^ -H generally takes place between -40 ° C and + 60 ° C, preferably between -20 ° C and + 30 ° C. The solvents that can be used are the same as those of the preceding reaction step. The concentration of products of formulas (III) and (I) is generally between 5 and 50%. The reaction is advantageously carried out in the presence of tertiary amines, in particular triethylamine and pyridine; instead of the usual acid acceptor, it is possible to use the compound R ^ -H itself which is therefore in an amount very much greater than the amount normally used when it is simply a reagent.

The following examples, given without limitation, illustrate the invention and show how it can be used.

* '' Examples 1 to 19: To 20 cm of chlorosulfonyl isocyanate, 18.1 g of acifluorfen are added, then, while stirring, the reaction mixture is gradually heated to 50 ° C. until the end of the evolution. HCl gas. Cool, add 50 cm3 of hexane, filter the precipitate, wash the latter with hexane, then dry under vacuum. This gives 22.2 g of 5- | 2-chloro-4- (trifluorom ^ thyl) ph ^ noxy -2-nitro-N-chlo-rosulfonylbenzamide which is dissolved in 100 cm ^ of acetonitrile . Stirred, cooled to 0 ° C and added dropwise * 3 'a solution of 4.4 g of dimethylamine in 20 cm of ac ^ -tonitrile. The reaction medium is then allowed to return to; 20 ° C and then stirring is continued for 1 hour at this temperature.

The acetonitrile is evaporated and the residue is dissolved in chloroform. This chloroform solution is washed with water, dried, concentrated and the residue is purified by chromatography on silica with chloroform as glutinous * 0 °, thus obtaining 10.8 g of compound No. 4 of formula:

Ci ^ CQ-NH-SO ^ N (CH ^) 2 cf3 -M- ° N ° 2 'Λ.

The various compounds n ° 1 to 19 are prepared from. the same way by replacing dimethylamine with amine I or the corresponding alcohol. The formulas and physical characteristics I of these products are collated in table (I).

îi Example 20: Herbicide application, preemergence I (= preemo ^ oence) of plant species g In 9 x 9 x 9 cm pots filled with light agricultural soil, a number of seeds is sown determined in func * tion of the plant species and the size of the seed.

dd ‘^ i The pots are treated by spraying porridge p in an amount corresponding to a volume dose of applicative- dd 7 of 500 1 / ha and containing the active material at the desired concentration.

The treatment with the porridge is therefore carried out on seeds not covered with soil (the term porridge is used to denote, in general, the diluted compositions cj water, such as they are applied to vegetables).

The slurry used for the treatment is an aqueous suspension of the active material containing 0.1% by weight of C ^ mulsol NP10 (surfactant consisting of al-kylphpnol poly ^ thoxyl ^, mainly nonylph ^ noldçca ^ -thoxylp ) and 0.04% by weight of Tween 20 (surfactant consisting of laurate of polyoxy ^ thylenf derivative of sorbitol).

This suspension was obtained by mixing and grinding the ingredients in a micronizer, so as to obtain an average particle size of less than 40 microns. i

Depending on the concentration of active ingredient in the spray, the dose of active ingredient applied was 0.25 to 4 kg / ha.

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

The pots are then placed in tanks intended to receive the irrigation water, under sub-irrigation, and kept * for 21 days ^ temperature of 22-24 ° C under 70% relative humidity.

After 21 days, count the number of live plants in the pots treated with the spray containing the active ingredient to be tested and the number of live plants. in a control pot treated according to the same conditions, but by means of a slurry containing no active material. The percentage of destruction of the treated plants is thus determined relative to the untreated control. A percentage of destruction equal to 100% indicates that there has been complete destruction of the plant species considered and a percentage of 0% indicates that the number of live plants in the treated pot are * · identical | the one in the witness jar.

V

• 8

Example 21: Herbicide application, post-emergence (= post-season) of plant species i In 9 x 9 x 9 cm pots filled with light agricultural soil, a number of seeds is determined depending on the plant species and the size of the seed.

The seeds are then covered with a layer of soil about 3 mm thick and the seed is allowed to germinate until it gives rise to a seedling at the appropriate stage of development. The processing stage for grasses is the "second leaf in formation" stage. The suitable stage for soybeans is the "first spreading trifoliate leaf" stage. The processing stage for other broadleaf weeds is the "spreading cotyledons, | first true leaf developing" stage.

The pots are then treated by spraying with a mixture of quantity corresponding to a volume dose j of application of 500 l / ha and containing the active material at i 'the desired concentration.

| The slurry was prepared in the same manner as in Example 20.

Depending on the concentration of active ingredient in the porridge, the dose of active ingredient applied was 0.25 | ^ 4 kg / ha. -! The treated pots are then placed in tanks intended to receive the irrigation water, under subirrigation, and] * maintained for 21 days at a temperature of 22-24 ° C. under 70% f of relative humidity.

; 5 After 21 days, the number of living plants I in the pots treated with the spray containing the active ingredient to be tested is counted and the number of living plants | in a control pot treated according to the same conditions, but by means of a slurry containing no active material.

! The percentage of destruction of the treated plants is thus determined relative to the untreated control. A percentage of j destruction equal to 100 8 "indicates that there has been destruction! 'complete of the plant species considered and a percentage! /

I a

| / 6-.

9 of Ο% indicates that the number of living plants in the treated pot is identical to that in the control pot.

The plant spaces on which herbicide applications have been carried out are indicated in Table (II).

The results obtained in Examples 20 and 21 were indicated in Table (III) which combines both the pre-emergence results (= preemergence) according to Example 20 and the post-emergence results (= post-emergence) according to Example- • . pie 21. During these tests, we were able to observe improved performance (in particular selectivity) compared to a product representative of the prior art (European patents 3416 and 23392) and having the formula: 'Cl ^ C0- NH-SO2-CH3 CF3 0 N02 ^

Example 21a:

Excellent herbicidal results are also obtained by using the sodium salts (N-Na group compounds) of compounds 4, 5 and 9.

The tests carried out show the remarkably advantageous properties of the compounds according to the invention, which can be used both for pre-emergence treatments of crops and more particularly soybeans, and for post-emergence treatments, in particular of soybeans and cereals, including corn. In the case of soybeans, the activity of the compounds is particularly interesting when this crop is infested with dicotyledonous weeds such as Abutilon, Xanthium and Ipomea. Compared to the reference product> the products of the invention have improved selectivity.

For their practical use, the compounds according to the invention are rarely used alone. Most often these compounds are part of compositions. These compositions, "which can be used as herbicidal agents, contain as active material a compound according to the invention as described above in combination with solid or liquid carriers, / annpnt.ahlpi pn anrimiltnrp and enant tensin-sntif aosnts. 10 i · ily acceptable in agriculture. In particular, the usual inert supports and the usual surfactants are usable. These compositions are cheerfully part of the invention.

|

These compositions can also contain all kinds of other ingredients such as, for example, colloids; protectors, adhesives, thickeners, thixotropic agents, penetration agents, stabilizers, sequestering agents, etc. as well as other known active ingredients ε} pesticidal properties (in particular insecticides, fungicides or herbicides) or with properties promoting plant growth (especially fertilizers) or with plant growth regulating properties. More generally, the compounds used in the invention can be combined with all the solid or liquid additives corresponding to the usual techniques of formulation.

The doses of use of the compounds used in the invention may vary within wide limits, in particular | according to the nature of the weeds to be eliminated the degree of in! usual culture of crops for these weeds, In general, the compositions according to the invention usually contain from about 0.05 to 95% | (by weight) of one or more active materials according to the invention, from 1% to 95% approximately of one or more supports j solid or liquid and optionally from 0.1 q 20¾ approximately | 'of one or more surfactants.

! "According to what has already been said about the compounds used | in the invention are generally associated with supports; and optionally surfactants.

By the term "support", in this paper, we | denotes an organic or mineral, natural or synthetic material, with which the active material is associated to facilitate its application to the plant, to seeds or to the soil. This support is therefore generally inert and it; must be acceptable in agriculture, especially on the treated plant b 1. The support can be solid (clays, silicates I ^; 11 natural or synthetic, silica, resins, waxes, solid fertilizers, etc.) or liquid (water; alcohols, in particular bu-tanol; esters, in particular acetate of m ^ thyl-glycol; cf-tones, in particular cyclohexanone and isophorone; petroleum fractions; aromatic hydrocarbons, in particular xylenes, or paraffinics; aliphatic chlorine hydrocarbons, in particular trichloro ^ thane, or aromatic, in particular chlorobenzene; solvents water-soluble such as dimethylformamide, dimethyl sulfoxide, N-mf-thyl-pyrrolidone; gas liqupfips "etc.).

The surfactant can be an emulsifying, dispersing or wetting agent of the ionic or nonionic type or a mixture of such surfactants. Mention may be made, for example, of salts of polyacrylic acids, salts of lignosulfonic acids, salts of phnolsulfonic or naphthalene sulfonic acids, polycondensates of ethylene oxide on fatty alcohols or on fatty acids or on fatty amines, substituted phenols (in particular alkylphenols or arylphenols), ester salts of sulphosuccinic acids, taurine derivatives (especially alkyltaurates), phosphoric esters of polyoxyethyl alcohols or phenols, esters of fatty acids and polyols, sulfates, sulfonates and phosphates of the above compounds. The presence of at least one surfactant is generally essential when the active material and / or the inert support are not soluble in water and the vector agent for the application is water.

• For their application, the compounds of formula (I) are therefore generally in the form of compositions; these compositions according to the invention are themselves in fairly diverse forms, solid or liquid.

As forms of solid compositions, mention may be made of dusting powders (with a content of compound of formula (I) which can range up to 100%) and granules, in particular those obtained by extrusion, by compacting, · by impregnation

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12 of a granulated support, by granulation from a powder (the content of compound of formula (I) in these granules being between 0.5 and 80% for the latter cases). The solid compositions most often contain 20 to 80% of active material.

As forms of liquid compositions or intended to constitute liquid compositions during application, mention may be made of solutions, in particular emulsifiable concentrates, emulsions, concentrated suspensions, aerosols, wettable powders (or spray powder). ), self-dispersing granules, pasta.

Liquid compositions most often contain 10 to 80% of active material.

I i

The emulsifiable or soluble concentrates also include: most often 10 to 80% of active material, emulsifiers or solutions ready for application containing, for their part, 0.01 to 20% of active material. In addition to the solvent, emulsifiable concentrates can contain, when necessary, 2 to 20% of suitable additives, such as stabilizers, surfactants, penetrating agents, corrosion inhibitors, colorants, adhesives.

From these concentrates, elutions of any desired concentration can be obtained by dilution with water, which are particularly suitable for application to plants.

As an example, here is the composition of some emulsifiable concentrates: - active ingredient 250 g - polyethoxylated alkylphenol 30 g î - calcium alkylarylsulfonate 50 g • - petroleum distillation cut, distill-; lant between 160 and 185 ° C 670 g! Other formula: - active ingredient 350 g l - polyethoxylated castor oil 60 g I L · ^ \? 13 - sodium alkylarylsulfonate 40 g - cyclohexanone 150 g - xylene 400 g

Other formula: - active ingredient 400 g - alkyl phenol polyethoxylc 100 g - methyl ether of ethylene glycol 250 g - aromatic petroleum cut distilling between 160-185 ° C 250 g

Other formula: - active ingredient 400 g - tristyrylph phosphate ^ poly poly thoxyl ^ 50 g - alkylph ^ nol phosphate poly ^ thoxylp 65 g - sodium alkyl benzene sulfonate 35 g - cyclohexanone 300 g - distilled aromatic petroleum cut.

between 160-185 ° C 150 g

Other formula: - active ingredient 400 g / 1 - alkali dodecylbenzene sulfonate 24 g / 1 - oxyethylated nonylphenol containing 10 molecules of ethylene oxide 16 g / 1 - cyclohexanone 200 g / 1 - aromatic solvent q.s.p. 1 litre.

According to another formula of emulsifiable concentrate we use: '. - active ingredient - 250 g - epoxy vegetable oil 25 g - mixture of alkylaryl sulfonate and polyglycol ether and fatty alcohols 100 g - dimethylformamide 50 g - xylene 575 g

The concentrated suspensions, which are applicable in spraying, are prepared so as to obtain a stable fluid product which does not deposit (fine grinding) and they usually contain from 10 to 75% of active material,

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"14 ΐ 'from 0.5 to 15% of surfactants, from 0.1 to 10% of thixotropic agents, from 0 to 10% of suitable additives, such as defoamers, corrosion inhibitors, stabilizers, penetrating agents and adhesives and, as a carrier, water or an organic liquid in which the active ingredient is sparingly soluble or insoluble: some organic solids or mineral salts may be dissolved in the carrier to help to prevent sedimentation or as antifreeze for water.

By way of example, here is a concentrated suspension composition: - active material 50 g - polyethoxylated tristyrylphenol phosphate 50 g - polyethoxylated alkylphenol 50 g - sodium polycarboxylate 20 g - ethylene glycol 50 g \ | - organopolysiloxane oil (antifoam) 1 g J - polysaccharide 12.5 g | - water 316.5 g! Wettable powders (or spray powder) are usually prepared so that they contain 20 to 95% of active ingredient, and usually contain, in addition to the solid support, 0 to 5% of a wetting agent, from 3 to 10% of a dispersing agent, and, quant! if necessary, from 0 to 10% of one or more stabilizers I and / or other additives, such as penetration agents, des; adhesives, or anticaking agents, dyes, etc. By way of example, here are various compositions of I wettable powders: | - active ingredient 50% | - calcium lignosulfonate (deflocculant) 5% - isopropylnaphthalene sulfonate (anionic wetting agent) 1% 1 - anti-clumping silica 5% | - kaolin (charge) 39%

Another example of a wettable powder q 80% is

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L * 15 given below: - active material 80% i - sodium alkylnaphthalene sulfonate 2% - sodium lignosulfonate 2% - anti-clumping silica 3% - kaolin 13%

Another example of a wettable powder is given below: - active material 50% - alkylnaphthalene sodium sulfonate 2% - methyl cellulose of low viscosity 2% - diatomaceous earth 46%

Another example of a wettable powder is given below: ...

- active ingredient 90% - sodium dioctylsulfosuccinate 0.2%, - synthetic silica 9.8%

Another 40% spray powder composition uses the following constituents: - active ingredient 400 g - sodium lignosulfonate 50 g - dibutylnaphthalene sodium sulfonate 10 g - silica 540 g

Another powder composition ε | spray at 25% uses the following constituents: - active ingredient 250 g - isooctylphenoxy-polyoxyethylene-ethanol 25 g - edulponderal mixture of chalk

Champagne and hydroxyethylcellulose 17 g - sodium aluminosilicate 543 g - kieselguhr 165 g

Another 10% spray powder composition uses the following constituents: - active ingredient 100 g - mixture of sodium salts of saturated fatty acid sulfates 30 g 16 - condensation product of naphthalene sulfonic acid and formaldehyde 50 gj - kaolin 820 g | To obtain these sprayable powders or wettable powders, the active materials are intimately mixed in appropriate mixers with the additional substances or the molten active material is impregnated on the porous filler and milled with mills or other suitable grinders. This gives sprayable powders whose wettability and suspension are advantageous; 'they can be suspended with water at any desired concentration and this suspension can be used very advantageously in particular for application to plant leaves.

The “self-dispersible” granules (in English “dry flowable”; more precisely, they are granules easily dispersible in water) have a composition substantially similar to that of wettable powders. They can be prepared by granulation of formulations described for wettable powders, either by the wet route (bringing the finely divided active material into contact with the inert filler and with a little water, for example 1 to 20%, or solution aqueous dispersant or binder, then drying and sieving), or by dry process (compacting then grinding and sieving).

As an example, here is a self-dispersible granule formulation:! - active ingredient 800 g | - sodium alkylnaphthalene sulfonate 20 g | - methylene bis naphthalene sulfonate | sodium 80 g! - kaolin 100 g | Instead of wettable powders, we can do it! pasta. The conditions and methods of realization and | # use of these pastes is similar to that of wettable powders or spray powders.

I ^ i v- '17

As already stated, the aqueous dispersions and ^ emulsions, for example compositions obtained by diluting with water a wettable powder or an emulsifiable concentrate according to the invention, are included in the general scope of the compositions. usable in the present invention. The emulsions can be of the water-in-oil or oil-in-water type and they can have a thick consistency like that of a "mayonnaise".

All these dispersions or aqueous or boiled emulsions are applicable to crops which weed everywhere. suitable means, mainly by spraying, at doses which are generally of the order of 100 q 1,200 liters of spray mixture per hectare.

The granules intended to be placed on the ground are usually prepared so that they have dimensions of between 0.1 and 2 mm and they can be produced by agglomeration or impregnation. Preferably, the granules contain 1 to 25% of active ingredient and 0 to 10% of additives such as stabilizers, slow release modifiers, binders and solvents.

According to an example of a granule composition, the following constituents are used: - active material 50 g ^; - propylene glycol 25 g | - clay (particle size: 0.3 to 0.8 mm) 525 g

As indicated above, the invention also relates to a process for weeding crops, in particular cereals such as wheat and including corn as well as | soybean, according to which an effective and non-phytotoxic amount vis-à-vis the crop concerned is applied to the plants and / or to the soil in the area to be weeded, of at least one of the compounds according to the invention. These are used practically in the form of the herbicidal compositions according to the invention which have been described above. Generally amounts of active ingredient ranging from 0.01 to 5 kg / ha, preferably from 0.1 to 2 kg / ha, give good results,.

: L · · - 18 "<it being understood that the choice of the quantity of active ingredient c | use depends on the intensity of the problem to be solved, the climatic conditions and the culture considered. The treatment can be carried out either in pre-emergence from crops and weeds, or in pre-sowing of crops with incorporation into the soil (this incorporation is therefore an operation complementary to the treatment process of the invention), or post-emergence. Other methods of implementing the treatment method according to the invention can also be used: thus the active material can be applied to the soil, with or without incorporation, before transplanting a culture.

The treatment method of the invention is applicable both in the case of annual crops and in the case of perennial crops; in the latter case, it is preferred to apply the active ingredients of the invention in a localized manner, for example between the rows of said cultures.

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Table (I): products of formula Cl CO-NH-SO ^ R1 cf3 \ v · 0 no2 "T î 'Γ

Ccmposed R point of others n ° fusion..en ° C ... characteristics 1 CHg ci ^ -o j 150. 76.5. %, CH? V.

2 ç ^^ pH-O- 110 85 fc · 3 CH3-O- i50 38% I ___________ 4 ÎCH3} 2N ”73 48. % 5 CH3-NH- 205 27% 6 {y- 39% 7 192 46% ch 8 —N 140 '27% __ ^ CH., _________ 9 NH 135-140 59% 2

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; ·. 20;

Table (I) (continued) i - - ............

I Compound n "R1 Point de RendeInent ........ fusion ....... v 10 (^) - NH- 188 90% 11 C3 ^) - NH- 190 84% 12 (ÿ} - NH- 190 68% __h___ | 13 183 29 f 5% | 14 ^ S-NH- 155 34% 3 'Π! - crxi ---; -) 15 ®-NH- 80 79% j' -16 CÏV NH— I8n 87% i 17 65 25.5%!! __ C \ .1 ___; 18 Cl- (ÿ-NH- 180 72% 119 j ^ NH- 185 76.5%

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Claims (17)

1. X is 0 or S, 1 2 5 ;; - R and R represent a hydrocarbyl, aryl, jj or heterocyclic group, substituted or not, Ij - R ^ and R ^ have one of the meanings given for j R “, and can also represent the hydrogen atom or j an alkoxyl radical or form together a single radical equivalent to 1 hydrocarbon eventuU-emen't: substituted »I - R has one of the meanings given for M and may also represent l an alkyl group ae 1 to 4 C. I 2) Compounds according to claim 1, characterized in that the alkyl or alkoxyl radicals which they contain have from 1 to 2 5 £} 4 carbon atoms and / or that R and R are from 1 to 12 ri | carbon atoms. L · c «27 3. Composites according to one of claims 1 or 2, characterized in that R ^, R "5, R ^ and R5 represent an alkyl group substituted or not by at most 4 substituents such as an aryl group (particularly phenyl), a chlorine or bromine atom, a hydroxyl, alkoxyl, SH, alkylthio, carboxyl, alkyl carboxylate, cyano group; an alkenyl or alkynyl group preferably having from 2 to 6 carbon atoms; an aryl group, particularly phenyl, optionally substituted with a maximum of 4 substituents such as Cl, Br, an alkyl, cyano, carboxyl, alkyl carboxylate group, NO2, OH, alkoxyl, SH, alkylthio, the various alkyl or alkoxyl groups mentioned above q as substituents preferably having 1 q 4 carbon atoms. 4. Compounds according to one of claims 1 to 3, character-! laughed in that: K j - is Cl, X2 is CF ^, W is -CH =, 1 is Cl or NO2, R is a hydrogen or sodium I atom. j j 3) Compounds according to one of Claims 1 to 4, character. , 1 4 ns ^ s in that R "is -NH-R. 5. K I -X-R, M ′ - M represents a hydrogen atom or a cation acceptable in agriculture such as an alkali metal cation, or an ammonium cation, substituted or not. 6. Process for the preparation of compounds according to one of claims 1 to 5 characterized in that a * - acid of formula: is reacted! I 1 _ Χλ _ COOE. . j "; X2 0 - {ÿ -X3" n with chlorosulfonylisocyanate so as to obtain a product of formula ï X C0-NH-S02C1! 0 (iii)! 1 / L ·. .. · · ·. 28 j then that this product of formula (III) is reacted with a compound of formula R ^ -H. The various symbols used in these formulas may have the meanings indicated in claims 1 to 5. 7. Method according to claim 6, characterized in that the first phase is carried out between 20 and 100 ° C, in a solvent with a concentration of products of formulas (II) and (III) between 5 and 70% by weight . 8. Method according to one of claims 6 or 7, characterized in that the second phase of the reaction is carried out * between -40 ° C and + 60 ° C, in a solvent and with a concentration in products of formulas (III) and (I) between 5 and 50% by weight. 9. Herbicidal compositions characterized in that they contain as active material a compound according to one of claims 1 to 5, this active material being in combination | tion with at least one inert support acceptable in agriculture! ture. 10. Compositions according to claim 9, characterized in that they contain 0.05 to 95% by weight of material! active. 11. Compositions according to one of claims 9 or 10, characterized in that they are liquid and that they; hold 10 q 80% of active ingredients. ! 12. Compositions according to one of claims 9 or 10,! 'characterized in that they are solid and contain 20 1.% i; £} 80% active ingredients. ; 13) Compositions according to one of claims 9 to 12, j characterized in that they contain 0.1 to 20% of surfactant. ; 14) Method for weeding crops, characterized in that an effective and non-phytotoxic amount of a composition according to one of claims 9 to 13 is applied. J 15) Method according to claim 14, characterized in | that the composition is applied to a post-emergent or sampled soybean crop. ! L 29 16. Process according to claim 14, characterized in that the culture is a crop of cpr ^ ales infested or liable to be infested with at least one dicoty-1 ^ done weed, such as Abutilon, Xanthium and the Ipom ^ a. 17. Proc ^ d ^ according to one of claims 14 ε) 16, characterized in that the compound of formula (I) is applied èj i at a rate of 0.1 to 2 kg / ha. i ί; Λ K i j Λ i i i