FR2510103A1 - HERBICIDE COMPOUNDS DERIVED FROM PHENOXYBENZOIC ACIDS - Google Patents

Abstract

NEW HERBICIDE FOR CEREALS OR SOY, HAS THE FORMULA: (CF DRAWING IN BOPI) IN WHICH: -Y IS AN ATOM OF NITROGEN OR A -CH GROUP; -Y IS AN ATOM OF NITROGEN OR A -CX GROUP, THIS LATEST POSSIBILITY ONLY TAKING PLACE WHEN THERE IS A -CH; -X, X, X, IDENTICAL OR DIFFERENT GROUP, REPRESENTING A HALOGEN ATOM OR A POLYHALOALKYL, CYANO, NITRO, ALKYL, ALKOXYL, ALKYROSULHONYLE, NITRO, NITRO, ALKOXYL, ALKYROSULHONYLE, NITRO , ALKYL CARBOXYLATE; -X IS HYDROGEN ATOM OR ONE OF THE MEANINGS GIVEN BY XAX; -Y IS HYDROXYL OR HALOGEN ATOM; -R IS A HYDROCARBON RADICAL, SUBSTITUTED OR NOT, OR A SUBSTITUTE HETEROCYCLE OR NOT

Description

The invention relates to selective herbicides of the family of the acids

phonoxybenzoic substances and their

  procode of preparation and their application.

  Herbicides derived from phenolic acid are known

  xybenzo Xque and more particularly 5-l 2-chloro-4 (trifluoromethyl) phenoxyl-nitrobenzoic acid, known as

name of acifluorfen.

  Various derivatives of these compounds have already been proposed.

  including alkyl esters of cycloalkyl, thioal-

  kyle, phenyl, mono or dialkylated amides, chlo-

  Among the US patents describing such compounds are US Pat. Nos. 3,652,645, 3,784 and US Pat.

  635, 3,873,302, 3,983, 68, 3,907,866, 3,798,276, 3,928,416,

4,063,929.

  The chemical name of the products in the pre-

  This statement is made according to the French nomenclature but using the numbering of the positions of the substituents according to the Anglo-Saxon nomenclature (number placed before the

name of the substituent).

  Malgro the large number of phenoxy acid derivatives

  benzoic substances, or even simple diphenyl ethers,

  it is desirable to have other herbs available

  bicides of these families so 4 can solve all

  possible cases of desirable herbicide treatments,

especially in pre-emergence.

  In this paper, the terms pre-emergence and pre-emergence are used as synonyms and the terms

  postlevee and postemergence as synonyms.

  The subject of the invention is therefore new herbicidal compounds of formula: Y X 2 CO-N-SO-R (I)

X 1 2 O X 3

  Wherein Y 1 is a nitrogen atom or a CH = group, Y 2 is a nitrogen atom or a -CX 4 = group, this last possibility occurring only when Y 1 is a group -CH =, X 1, X 2, X 3, which may be identical or different, represent a halogen atom (in particular chlorine, bromine or

  fluorine), a polyhaloalkyl group, in particular trifluoromethyl

  thyl, a cyano or nitro group, an alkyl, alkoxy, SO 2 alkyl, 502 NH 2, nitroso, alkyl carboxylate group, the alkyl part of these radicals preferably having 1 to 4 carbon atoms, X 4 has the same meanings as those given for X 1 to X and may be, in addition, the hydrogen atom, R is a hydrocarbon radical S, substituted or unsubstituted, having

  generally from 1 to 12 carbon atoms, including a

  dical alkyl or aryl, substitutes or not, or a h Stocyclocycle

  substituted or unsubstituted, having 5 to 7 atoms in the ring.

  Y is a hydroxyl group or a halogen atom,

Feel the chlorine.

  As examples of R radicals, there may be mentioned more particularly the alkyl radicals of 1 to 4 carbon atoms; aryl radicals, especially ph Snyl, unsubstituted or substituted by alkyl radicals each having 1 to 4 carbon atoms, or by chlorine or bromine atoms, or by hydroxy, SH, CN, COOH, or by alkoxy, thioalkyl, alkyl carboxylate groups, the alkyl portions of these radicals having from 1 to 4

  carbon atoms in the alkyl part; groups alce-

  nyl and alkynyl having 26 carbon atoms.

  Among the compounds of formula (I), a class all

  particularly advantageous is represented by the

  in which X 1 and X 2 are polyhaloal-

  kyle or atoms d: halog Qne, Y 1 and Y 2 are the group

  -CH =, X 3 is the nitro group or a halogen atom.

  More particularly preferred are the compounds in

  which X 1 is CF 3, X 2 is Cl, X 3 is Cl or NO 2, Y 1 and Y 2 are -CH = It is therefore in particular of compounds of formula: ## STR1 ##

3 {ô {ô N 2 (II)

CF 3 3 O NO 2

  In these compounds, those for

  which R is an alkyl group and Y is a chlorine atom.

  On a fairly general level, compounds according to the

  vention can be most often prepared from formula precursors: Ys

X 2 CO-N-SO 2-R

X 14 X (III)

0 X 3

  in which Y 'is the hydrogen atom or an alkali metal atom, preferably sodium, the other symbols having the various meanings given above. Most of the compounds of formula (III), or their direct counterparts, are already described in the

  European Patent Nos. 3416 or 23,392.

  The compounds according to the invention in which Y is a halogen atom are conveniently prepared by reaction of a hypohalogenite with a precursor of formula (III) in

  Y 'is a hydrogen or alkali metal atom.

  The reaction is generally carried out in solution or

  aqueous or hydroorganic suspension in the presence of

  being miscible with water such as alcohols or ketones

  including methanol, ethanol, acetone, methylene

  ethylcetone, methyl isobutyltone The reaction is

  most often between 10 and 60 ° C., preferably between 10 and 400 ° C., the concentration of the reactive medium of formula (III) and product of formula (I) according to the invention being between 0.5 and 30 ° C. % by weight, preferably between 2 and 10%; the amount of hypohalogenite used is generally between 1 and 3 times

  stoichiometry The p H, during the reaction is gene-

  typically greater than 10, preferably greater than 11.5.

  The compounds according to the invention in which Y is a hydroxyl group are prepared genally according to the invention.

  reaction scheme in which the symbol Ar represents

feel the radical:

X

X 2 X 1 o x 3

Y 1 Y 2

  Reaction Scheme Ar-CO Cl + R-502-NHOH 4 Ar-CO-N-SO 2 R Ar-CO-O + HC 1 l then Ar-CO-N-SO 2 R> Ar-CO-N-SO 2 R (+ Ar COOR)

I

Ar-CO-O (+ R OH) OH

  The first of these reactions is advantageous.

  in the presence of an acid acceptor such as

  Tertiary, including pyridine.

  The second of these reactions that is an alcoholysis

  by the action of an alkaline alkoxide (or hy

  alkaline hydroxide in solution in an alcohol denotes R 1 OH in the scheme) Duis Dar action of a strong acid such as

hydrochloric acid.

  The compounds according to the invention are especially advantageous by virtue of their effectiveness, as well as by their herbicidal activity in pre-emergence and post-emergence. Among the cultures which can be treated by the products of the invention, mention may be made of soybeans, cotton, rice, peanuts, cereals, including maize

  Some examples given below in a nonlimited

  illustrate the invention and show how it can

to be put into practice.

  Example 1: In 20 cm 3 of aqueous hypochlorite solution

  sodium rite containing 1.5 mole / l of hypochlorite and

  soda so that p H is equal to 12,

  0.5 g of 5-l 2,4-dichlorophenoxy-2-nitro-N-methanesulfonylbenzamide (melting point: 18 ° C.) was stirred for 30 min. 4 200 ° C. Acetic acid was added dropwise. Until we reach a pH of 7.5; we then continue

stirring for another 30 minutes.

  Filter, wash the precipitate with cold water and air dry; 0.3 g of 5-l-2,4-dichlorophonoxy-2-nitro-N-chloro-N-methanesulphonylbenzamide, mp 161 ° -163 ° C., and of formula: ## STR2 ## CO-N-SO 2-CH 3 OLNO

  This compound has an infra-red absorption band

  red 1728 cm-1 (carbonyl band) while the band

  corresponding on the starting reagent is 1688 cm-1.

  EXAMPLE 2 In 10 liters of water, 4.46 liters of bleach containing 1.57 moles / l of sodium hypochlorite and 105 ml of 30% by weight NaOH are added so that the pH is cal at 12.2.

  It is added gradually to 18-20 ° C. under stirring.

  45 hours, 458 g of 5-12-chloro-4- (trifluoro-

  methyl) phinoxyl-2-nitro-N-mithane sulphonyl-benzamide with a melting point of 215-2180 ° C. and of formula: Cl CO-NH-502-CH 3

CF 3 O NO 2

  Stirring is continued for 4 hours. It is then neutralized by adding progressively in mn 215 ml of acetic acid while maintaining the temperature

18-20 C.

  The white precipitate is filtered, washed with water, drained and dried under vacuum in the presence of 205 g. 279 g of 2-chloro-4- (trifluoromethyl) phenoxy -2-nitro-N are obtained. 4-chloro-N-methanesulphonylbenzamide, m.p. 161162 ° C. It is recrystallizable from a diethyl ether / chloroform mixture and has the formula: ## STR1 ## CO-N-SO 2 -CH 3

CF 3 O NO 2

  In nuclear magnetic resonance it does not present NH band and in infrared it presents the band

  of carbonyl absorption 1728 cm 1.

Example 3

  In terraces of 20 cm x 25 cm containing soil, we have the species of crops and bad

  herbs in rows 10 cm long.

  The species used are indicated in the

table (I).

  Cotton, maize, soya and Xanthium are

  semos 4 reason 4 q 5 seeds per row.

  The smaller species (velvety mustard,

  vulture, amaranth, Italian millet and the green variety) are se-

  not counting the seeds but in sufficient numbers, however,

  to form a tight line of plan-

you're the.

  The initial watering until the period of the ómer-

  is carried out over the earth covering the

seeds.

  Premergence treatment is performed # minus

one day after sowing.

  The desired stage of development for treatment

  postemergence of cotton, soybean, xanthium, velvetleaf, wild mustard and chenopodium is the

  stage of a true leaf or trifoliate leaf

  For the Xs, the desired stage is 7.5 cm, whereas for grasses the desired stage is

a height of 2.5 cm.

  The compositions of the invention are applied by spraying at a pressure of 2.5 bar (= 36

  psi) 4 reason 375 1 / ha (= 40 gallons / acre)

  sprays consisted of a proportionate mixture of

  volume of 20 cm 3 of water and 0.1% of surfactant (polyoxyethylene ether mixture

  alkaline (C 6 -C 16) benzene sulfonates).

  After treatment, irrigation is done by undergoing

  rigidity for seedlings having emerged and by

  wise above for seeds that have not yet given

seedlings.

  2 weeks after treatment, the measurements are taken

  on a scale of 0 to 100%.

  This measure indicates the level of destruction; for the crops this measure indicates the degree of attack or degree of phytotoxicity, the zoro score being assigned 4 of the plants in the same state as the witness and the score of 100 being attributed to complete destruction.

  As regards the application rates, the cor-

  Correspondence between American and American units is the following S: Pounds / acres 10 4 2 1 0.5 0.25 0.125 0.0625 kg / ha 11.2 4.48 2.24 1.12 0, 56 0, 28 0.14 0.07 Table (II) gives the results obtained with

the compounds of Examples 1 and 2.

  Example 4: Herbicidal application, taken from vital species. In 9 x 9 x 9 cm pots filled with farmland, the number of seeds is determined according to the vege- tural space and the size of the seed. We then cover the seeds with a layer of

earth about 3 mm thick.

  After humidification of the earth, the pots are

  sprayed with a quantity of pulp

  laying at a chemical application rate of 500 1 / ha and

  containing the active ingredient at the desired concentration.

  The slurry was prepared by diluting a

  Wettable agent itself prepared from 500 g of active ingredient of sodium alkylnaphthalenesulfonate, methylene bis (sodium naphthalene sulphonate), silica 390 g of kaolin According to the concentration of active substance of the boiled, the dose of active ingredient applied at 0.25

4 2 kg / ha.

  The pots are then placed in sturdy tubs to receive irrigation water, under irrigation, and maintained for 21 days at a temperature of 22-24 C under

% relative humidity.

  After 21 days, we count the number of live plants in the pots treated by the slurry containing the active ingredient to be tested and the number of live plants in a witness pot treated under the same conditions, but

  by means of a slurry containing no active ingredient.

  This determines the percentage of destruction of

  treated with respect to the untreated witness

  level of destruction equal to 100% indicates that there were

  complete truction of the plant species considered and a

  percentage of 0% indicates that the number of live plants

  in the potty pot 'is identical to that in the pot witness. Example 5: Herbicide application, in postlevee species

vyggtales.

  In pots of 9 x 9 x 9 cm filled with leg 4 agricultural land, a number of seeds is sown according to the vegetable 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 4 cm high. The pots are then treated by pulverizing a quantity of slurry corresponding to an application volume dose of 500 l / ha and containing the active ingredient at room temperature.

the desired concentration.

  The porridge has been prepared in the same way as

example 4.

  Depending on the active ingredient concentration of the slurry, the dose of active ingredient applied

0.125 4 1 kg / ha.

  The treated pots are then placed in bins intended to receive the watering water, under irrigation, and maintained at a time of less than 22%.

% relative humidity.

  After 14 days, the number of live plants in the pots treated with the slurry containing the active ingredient to be tested and the number of live plants in a tea pot treated under the same conditions, but by means of a slurry containing no active ingredient.

  The percentage of Destruction of

  treated in relation to the untreated witness

  destruction rate of 4 100% indicates that there were

  complete truction of the plant space considered and a

  percentage of 0% indicates that the number of live plants

  in the potty pot is identical to that in the pot witness. The results of Examples 4 and 5 are indicated

in table (III).

  This table (III) comprises on the one hand the results of pre-emergence obtained according to example 4 and on the other hand

  postemergence results obtained according to Example 5.

  The tests carried out thus show the proprilths

  remarkably advantageous compounds according to the invention.

  tion, as well as pre-emergence treatments for cul-

  particularly in the case of soya bean and cereals, the activity of the compounds is particularly interesting when this crop is infested with dicotyledonous weeds such as

  Abutilon, Xanthium and Ipomea In the case of cereals

  the activity of the compounds is particularly interesting.

  when this crop is infested with

  dicotyledons, including Polygonum, Amarantus, Ambro-

  sia, Chrysanthenum, Stellaria and Galium.

  For their practical use, the compounds according to

  These compositions, which can be used as herbicidal agents, contain, as active ingredient, a compost according to the invention as dicrit precociously in association with the solid supports, or it can be used as herbicidal agents.

  liquids, acceptable in agriculture, and agents

  also active in agriculture.

  are used the inert and usual supports and

  the usual surfactants These compositions are óga-

  part of the invention. These compositions may also contain any kind of other ingredients such as, for example, protective colloids, adhesives, thickeners, thixotropic agents, penetration agents, stabilizers,

  sequestrants, etc. as well as other active materials

  known 4 pesticidal properties (especially insecticides)

  cides, fungicides or herbicides) or q proprilths favoring

  the growth of plants (especially fertilizers) or

  More generally, the compounds of the invention can be used to regulate the growth of plants.

  be combined with all solid or liquid additives

  corresponding to the usual techniques of formu-

lation.

  The doses of use of the compounds used in the

  may vary within a wide range of

  depending on the nature of the weeds to be eliminated and the degree of

  usual feast of crops for these weeds.

  In a general way, the compositions according to the invention

  vention usually contain about 0.05 to 95%

  (by weight) of one or more active ingredients according to

  about 1% to about 95% of one or more solid or liquid carriers and possibly about 0.1% to about 20%

  one or more surfactants.

  According to what has already been said, the compounds used in the invention are generally associated with

  and optionally surfactants.

  By the term "support" in this

  dfsigne an organic or mineral material, natural or '.

  synthetic material, with which the active ingredient is associated

  to improve its application on the plant, on

  This support is usually inert

25.10103

  and it must be acceptable in agriculture, especially on the

  treated plant The support can be solid (clays, sili-

  natural or synthetic cates, silica, resins, waxes,

  solid fertilizers, etc.) or liquid (water, alcohols, especially

  butanol; esters, in particular methyl acetate

  glycol; ketones, in particular cyclohexanone and isophor

  rone; petroleum fractions; aromatic hydrocarbons, especially xylenes, or paraffinics; hydrocarbons

  aliphatic chlorines, especially trichloroethane, or aro-

  substances, including chlorobenzenes; hyphenated solvents

  such as dimethylformamide, dimethylsulphonate,

  foxide, N-mithyl-pyrrolidone; liquefied gases, etc).

  The surfactant may be an emulsifying agent

  ionic or non ionic dispersant or wetting agent

  or a mixture of such surfactants include for example polyacrylic acid salts,

  lignosulfonic acid salts, salts of phenolic acids,

  sulphonic or naphthalene sulphonyl ethers, polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines, substituted phenols (especially alkylphenols or arylphenols), salts of sulphosuccinic acid esters, dirivis of the

  taurine (in particular alkyltaurates), phospho-

  of polyoxyethyl alcohol or phenol, esters

  of fatty acids and polyols,

  fats, sulfonates and phosphates of the preceding compounds The presence of at least one surfactant is generally essential when the active ingredient and / or the carrier

  inert are not soluble in water and that the agent

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 under

  quite diverse forms, solid or liquid.

  As forms of solid compositions, mention may be made of dusting powders (4 content of compound of formula (I) up to 100%) and granules, in particular

  those obtained by extrusion, compaction,

* Gnation of a granule carrier, by granulation 4 from a powder (the content of compound of formula (I) in these granules {as between 0.5 and 80% for the latter cases). Solid compositions contain most often 20 4

% of active material.

  As forms of liquid or intended compositions

  constitute liquid compositions during the application

  the solutions, in particular the

  centers, emulsions, suspensions

  centers, aerosols, wettable powders (or powder

  4 spray), self-dispersible granules and pastes.

  Liquid compositions contain the most

10 to 80% active ingredient.

  Emulsifiable or soluble concentrates include

  most often 10 4 80% of the active ingredient, emul-

  In addition to the solvent, the 'mulsionnables' concentrates can contain, when it is

  20% of appropriate additives, such as

  bilants, surfactants, pinitrating agents,

  corrosion inhibitors, dyes, adhesives. From these concentrates, emulsions or solutions of any desired concentration can be obtained by dilution with water, which are particularly suitable for

application on plants.

  By way of example, here is the composition of some impermeable concentrates: active ingredient 4, 250 g, alkylphenol polyithoxy, 30 g, calcium alkylarylsulfonate, 50 g

  oil distillation cup, distillate

  between 60 and 60% C 670 g Other formula: active ingredient 350 g polyethoxylated castor oil 60 g sodium alkylarylsulfonate 40 g cyclohexanone 150 g xylene 400 g Other formula: active ingredient 400 g alkyl phenol polyethoxyl 100 g ether Methyl ethylene glycol 250 g aromatic petroleum fraction distilling between 160-185 C 250 g Other formula: active ingredient 400 g polyethoxylated tristyrylphenol phosphate 50 g alkylphenol polyithoxyl phosphate 65 g alkyl benzyl sodium sulfonate 35 g cyclohexanone 300 g aromatic aromatic fraction distilling between 160-185 C 150 g Other formula: active ingredient 400 g / 1 dodicylbenz 4 sulfonate alkaline 24 g / 1 nonylphenol oxyethyl 410 molecules of ethylene oxide 16 g / 1 cyclohexanone 200 g / l

aromatic solvent q s p 1 liter.

  According to another formula of emulsifiable concentrate, the following is used: active material 250 g epoxidized vegetable oil 25 g mfium of alkylaryl sulphonate and polyglycol ether and fatty alcohols 100 g dimethylformamide 50 g xy 14 n 575 g Concentrated suspensions, which are applicable in spraying, are prepared so as to obtain a stable fluid product which does not settle (fine grinding) and they usually contain from 10 to 75% of active substance, from 0.5 to 15% of agents. surfactants, from 0.1 to 10% of thixotropic agents, from 0 to 10% of appropriate additives,

  like anti-foams, corrosion inhibitors, -

  stabilizers, penetrants and adhesives and, as a carrier, water or an organic liquid in which

  the active material is not very soluble or not soluble:

  organic solid materials or mineral salts may

  to be dissolved in the support to help prevent

  sedimentation or as antifreezes for water.

  For example, here is a composition of sus-

  pension concentrate: active ingredient 50 g polyphthalenyl phosphate polyphenoxyl 50 g alkylphenol polyithoxyl 50 g sodium polycarboxylate 20 g glycol 50 g organopolysiloxane oil (antifoam) 1 g polysaccharide 12.5 g water 316.5 g Powders wettable (or powder 4 spray)

  are usually prepared in such a way that they contain

  20 4 95% of active material, and they contain

  usually, in addition to the solid support, from 5% to 5% wetting agent, from 3% to 10% dispersing agent, and

  where necessary, from 0 to 10% of one or more

  bilisants and / or other additives, such as penetration agents

  adhesives, anti-caking agents, colourants

  For example, here are various compositions of wettable powders: sde calcium (dfloculant) 5% calcium lignosulfonate (deflocu 1 ant) 5% isopropylnaphtal 4 ne sulfonate (anionic wetting agent) anti-clumping silica -kaolin (charge) A Another example of soft powder given below: active ingredient sodium alkylnaphthalenesulphonate sodium lignosulphonate anti-kaolin fuming silica foolproof 1%% 9% 4 80% is% 2% 2% 3% 13% Another example of a wettable powder is given below. -apr 4 S: active ingredient 50% sodium alkylnaphthalenesulphonate 2% low viscosity mithyl cellulose 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 b'composition of powder 4 spray uses the following constituents: active ingredient 400 g sodium lignosulfonate 50-g dibutylnaphthalene sodium sulfonate 10 g silica 540 9 Another powder composition 4 uses the following constituents: active ingredient isooctylphinoxy-polyoxyethyline-ithanol mixed with champagne chalk and hydroxyethylcellulose sodium aluminosilicate kieselguhr pulverize 4 25% 250 ggggg% Another powder composition depicting 4 10% uses following components: active ingredient 100 g sodium salt mixture of saturated fatty acid sulphates 30 g condensation product of naphthalenesulphonic acid and formaldehyde 50 g kaolin 820 g To obtain these powders 4 spray or wettable powders, mix intimately active ingredients

  in appropriate mixers with the additives

  the active ingredient melted on the

  porous load and grind with mills or other bro-

  We obtain powder by powder 4

  riser whose wettability and suspension are advantageous; they can be suspended with water any concentration dosiree and this suspension is

  can be used very advantageously, particularly for

  plication on the leaves of plants.

  "Autodispersible" granules (in English language)

  "dry flowable"; it is more exactly granules made

  dispersible in water) have a sensitive composition

  sibly close to that of wettable powders They

  can be prepared by granulation of formulations of

  for the wettable powders, either wet (bringing the finely divided active material into contact with the inert filler and with a little water, for example 14%, or an aqueous solution of dispersant or binder, then drying and sieving), or by S 4 che (compaction

then grinding and sieving).

  For example, here is a self-dispersible granule formulation: active ingredient 800 g sodium alkyl naphthalene 4 sodium sulfonate 20 g sodium methylene bis naphthalene sulfonate 80 g kaolin 100 g In place of wettable powders, it is possible to carry out

  The conditions and methods for producing and using these pastes are similar to those of wettable powders or sprayable powders.

  As has already been said, dispersions and

  aqueous solutions, for example compositions obtained from

  dilute with water a wettable powder or concentrate

  tremulsifiable according to the invention, are included in the general context of the compositions usable in the present

  The emulsions may be of the water-in-water type

  oil or oil-in-water and they can have a

  thick consistency like that of a "mayonnaise".

  All these dispersions or aqueous or boiled emulsions are applicable to the crops 4 weeding by any suitable means, mainly by spraying, doses which are genially of the order of 100 4 1 200

liters of porridge 4 per hectare.

  The granules intended to be placed on the floor are usually prepared so that they have dimensions of between 0.1 and 2 mm and can be manufactured by agglomeration or impregnation. Preferably, the granules contain 25% of active ingredient and O 4

  % of additives such as stabilizers, modifying agents,

  4 slow release, binders and solvents.

  According to an example of granule composition, the following constituents are used: active ingredient 50 g propylene glycol 25 g clay (particle size: 0.34 0.8 mm) 925 g

  As indicated above, the invention relates to

  A process of weeding crops, particularly cereals such as wheat and soybeans, in which the plants and / or the soil of the area is cultured is applied. po-s_ S e

  the concerned culture of at least one of the composites se-

  These are practically used in the form of the herbicidal compositions according to the invention which have

  ftf described above Generally the quantities of material

  active ingredient from 0.01 to 5 kg / ha, preferably from 0.1 to 2 kg / ha, give good results, it being understood that the

  choice of the quantity C of active ingredient to use is

  the intensity of the problem 4 to be solved, climatic conditions and culture considered.

  be carried out either pre-emergence (= pre-emergence)

  tures and weeds, or in

  corporation in the soil (this incorporation is therefore a

  complementary operation of the process for treating the in-

  vention), or in postlevee (= post-emergence) Other modes of implementation of the method of treatment according to the invention can still be used: thus one can

  apply the active ingredient to the soil, with or without

  poration, before transplanting a crop.

  The treatment process of the invention applies both in the case of annual crops and in the case of perennial crops; in the latter case, it is preferable to apply the active ingredients of the invention in a

  localized, for example between the rows of the said cultures.

TABLE I

  Name English Name Latin American Abreviation but Field corn CN Cotton Cotton CT Crops Bli Wheat WT Rice Rice RI Soybean Soybean SB Panisse Barnyardgrass Echinochloa BYG crus-galli Sftaire Giant foxtail Setaria faberii GTF Green Sitaire Green foxtail Setaria viridis GF Digitaria Crabgrass Digitaria CG sanguinalis Velvet leaf Abutilon VL theophrasti Italian Millet Foxtail millet Setaria italica FM Bad Cocklebur Xanthium CB herbs pennsylvanicum Wild mustard Wild mustard Sinapis arvensis WM Amaranth Pigweed Amaranthus PW retroflexus Bindweed purple Morningglory Ipomea purpurea MG (annual) Prickly AIDS Aids spinosa PS Wild oats Wild oat Avena fatua WO Renouje bindweed W Vild buckwheat Polygonum convolvulus Ambroisee Ragweed Ambrosia artemisiifolia 0 oz 01 Where 01 oz 06 oz Where 01 9 SIO qsod 1 01 OO op oz 09 06 OZ OL O 9 SIO 9 xd 1 OC O cry OO OZ OS 06 001 OT Cg OC oz oz oz T'O 01 O OO OO OZ 09 06 OOT OL 09 09 OZ az O ce Oz CE OO 09 09 06 001 001 06 09 OL O ú q S 'O -4 s Od z cc oz OO 09 this 06 ODT 001 001 09 OL OL ZT IT this OO oz al OB oz OOT OOT 06 06 09 os t TO 0 OE 00 T 09 00 T 00 T 00 T 001 00 T 00 T 9 z O qold Z Crl ce 001 OOT OOT OOT OOT OOT 00 TC) OT 95 10 os COE Op oz OOT OOT OOT 001 OOT 01 06 001 ZI "I qsocl ald im I las ND JD Sd D 14 my NM GD IA M JJID M andvfix no -oexa $ T sexn; Tn D saqxelq souje Anum ee ego (the help uolas in C) C> Ln r 4 Il C 4,

(II) Nvalani

TABLEM (Ill)

  0.5 0.25: i 0.5 0.25 0.125 f 90 60 f O 10-0 foo loo loo 100 100 go 60 30

100: O o 100 100 loo 100 -

  loo 100 100 100 loo go so loo 100 100 100 loo loo 100 loo loo loo loo 100 100 80 80 80 80

100 100 loo 100 100 -

loo 100 loo 100 loo loo 100 -

loo loo loo 160 100 loo 100

100 50 100 100 90 90

  100 lon 100 100 100 100: -Setirie Viridis loo loo loo go go 80 lo

-80 80 10

80 60

100 100 80 20 O

100 100 100 100 100

  : S.inapis 100 100 100 100 100 100 100 J

100 100

  Ga.Li um 100 100 100 90 -90 90 10: wheat 80 60 10 10 10 O O

20 10 10 O O O

: but 50 20 10 O: Co Ton

0 O

O

0 20 O O O

: Cyperus 80 O 60 20 O O

Claims (9)

  1) Composts characterized in that they have the formula: Y X 2 CO S 02-R X O X 3   in which: Y 1 is a nitrogen atom or a -CH = group, Y 2 is a nitrogen atom or a -CX 4 = group, the latter possibility only occurring when Y 1 is a group -CH =, -XX, X 2, X 3, identical or different, represent a halogen atom or a polyhaloalkyl, cyano, nitro, alkyl, alkoxyl, alkylsulfonyl, -502 NH 2 group, nitroso, alkyl carboxylate.   X 4 is the hydrogen atom or has one of the significances given by X 1 i X 3.   Y is a hydroxyl group or a halogen atom.   R is a hydrocarbon radical S, substituted or unsubstituted, or a substituted or unsubstituted hitirocycle; 2) compounds according to claim 1, characterized in that X 1 is C 1 or CF 3 X is C 1 l Y 1 and Y 2 are -CH = X 3 is Cl or NO 2   3) Composs according to one of claims 1 or 2,   in that X 1, X 2 and X 3 are such that the alkyl group (s) contained therein have from 1 to 4 carbon atoms, and that R is a hydrocarbon radical having from 1 to 12 carbon atoms, or h 6 tercocycle having 5 7 atoms in the cycle.   4) Compounds according to one of claims 1 q 3 features rised in that Y is Cl   ) Compounds according to one of claims 1 to 4   in that R is an alkyl radical having from 1 to 4 carbon atoms;   carbon mon; or a phenyl radical, unsubstituted or substituted by alkyl radicals or by chlorine or bromine atoms, hydroxyl, SH, CN, COOH groups, or by alkoxy thioalkyl, alkyl carboxylate groups; or an alkinyl or alkynyl group.   6) Process for the preparation of compounds which is one of the   Claims 1 to 5 in the formula of which Y is a   halogen atom characterized in that a hypohalogenite is reacted on a compound of formula Y ' X CO-N-SO 2-R   wherein Y 'is a hydrogen atom or an alkali metal atom -7) A process according to claim 6 characterized in that   that one operates in aqueous medium between -10 and + 60 C, -the concentration   reaction of the reaction medium with a reagent of formula (III) and a reaction product of between 0.5 and 30% by weight and p H being greater than 10   8) Process according to one of claims 6 or 7, characterized   in that the temperature is between 10 and 40 ° C and the concentration is between 2 and 10% and the pH is greater than 11.5 9) Herbicidal compositions characterized in that they contain as active ingredient a composed according to one of the   claims 1 to 5, this active matter being in association   with at least one inert carrier acceptable in agriculture.   Culture) Compositions according to claim 9, characterized in that they contain 0.05% to 95% by weight of active ingredient. 11) Compositions according to one of claims 9 or 10 characterized in that they are liquid and that they   hold 10 4 80% of active ingredients.   12) Compositions according to one of claims 9 or 10,   characterized by being solid and containing 20 4 95% active ingredients.   13) Compositions according to one of claims 9 q 12,   characterized in that they contain 0.1 to 20% surfactant. 14) Procfdi for weeding crops, characterized in that an effective amount of an active ingredient is applied according to one of claims 1 5.   ) Process according to claim 14, characterized in that   the composition is applied to an   festfe or likely to be infested by at least one   Abutilon, Xanthium and Ipomea weeds.   16) Method according to claim 14, characterized in that   that the crop is an infested cereal crop or sus-   It can be infested with at least one of the weeds, Polygonum, Chrysanthenum, Amarantus, Stellaria, Gallum.   17) Procfdf according to one of claims 14 to 16, characterized   in that the compost of formula (I) is applied 0.14 2 kg / ha.