CS201039B2 - Herbicide - Google Patents

Abstract

Herbicidal aqs. suspension contains a substituted benzofuran herbicide of formula (I): (where R1,R2,R3 independently = H or alkyl or R1 and R2 together or R2 and R3 together=alkylene; R4=hydroxy, opt. substd. alkoxy, opt. substd. alkenyloxy, opt. substd. alkynyloxy, opt. substd. aryloxy, alkylthio, NR6R7, -OOCR13, -OSO2R14 or -OOR15 or R3 and R4 together = O or =N-R16. R6, R7 = opt. substd. alkyl or together with the N atom form an opt. substd. heterocyclic; R13 = opt. substd. alkyl, opt. substd. alkenyl, opt. substd. alkynyl, opt. substd. aryl, mono- or dialkylamino, opt. substd-alkoxy, opt. substd. aryloxy, opt. substd. arylamino, opt. substd. alkenyloxy or opt. substd. alkynyloxy; R14= opt. substd. alkyl or opt. substd. aryl; R15= alkyl, alkenyl or alkynyl; R16 = alkyl or cycloalkyl; R5= R8CO-, R9SO2-, R9-SO-, R31R32NSO2; R8 = halogenated alkyl; R9 = opt. substd. alkyl or opt. substd. aryl; R31, R32 independently = H or opt. substd. alkyl and R10, R11, R12 independently = H, alkyl, halo, cyano, acyl or alkoxy). (I) has m.pt. >=50 degrees C and a water solubility >=0.1% at 25 degrees C. In addn. to water the compsn. also contains a polycarboxylated vinyl polymer as suspension agent, a surface activeaagent having a reversible thickening temp. of 45 degrees C or above and, when the surface active agent is not a sequenced copolymer of ethyleneoxide and propylene oxide, a deflocculating agent. Esp. useful for control of weeds in sugar beet but may also be used to control weeds in sunflowers, tobacco, pastures, crucifers etc. Usually 0.5-8kg/hectare (pref. 1-4 kg/hectare) of (I) are applied, after sowing. The suspension may be used at the post-emergent stage but is pref. used pre-emergence. The pref. cpd. (I) is 2-ethoxy-2,3-dihydro-3,3-dimethyl-benzofuran-5-yl methanesulphonate (ethofumesate).

Description

The invention relates to novel, particularly preferred formulations of certain known substituted benzofuran herbicides. Many of these herbicides are described in British Patent Specification 1,271,659.

Accordingly, the present invention provides a herbicidal composition comprising 0.05 to 700 g / l of a substituted benzofuran herbicide of formula I,

(I) wherein is ethoxy, propoxy or isopropoxy and

9

R 'group of the formula -S0 R _o -, u <wherein R is a methyl or ethyl group, provided that the compound has a melting point at least 50 ° C and a solubility in water at ° C at most 0.1%, wherein at least 85 % by weight of the particles of this compound have a diameter of less than 5 µm as measured by a Coulter Counter, which composition is characterized in that it is an aqueous suspension containing as suspending agent 0.5 to 50 g / l of xanthomonas hydrophilic colloid, and 0.5 to 30 µm. by weight, based on the amount of the compound of the formula I, of a block copolymer of ethylene oxide with propylene oxide as a surfactant, having a return temperature of at least 45 ° C.

A particularly preferred compound which can be formulated according to the invention is 2-ethoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulfonate (common name ethofumesate).

In one variation, the invention provides a herbicidal aqueous suspension comprising water, at least one compound of Formula I, a polycarboxylated vinyl polymer as a suspending agent, a reversible thickening surfactant as defined below, at least 45 ° C, and a deflocculating agent when: a compound other than a block copolymer of ethylene oxide with propylene oxide is used as the surfactant.

As used in this specification, the return thickening temperature is understood to mean the temperature at which there is a significant change in viscosity when the ground aqueous suspension containing 48.5 w / v is heated. % pure ethofumesate, 1.5 w / v% % surfactant, 4.85 w / v% % anionic sulfonated condensation sodium salt deflocculating agent (Dyapol PFS from Yorkshire Chemica Is Limited) and 0.1 w / v%; % of a silicone-based antifoam (Antifoam RD from Dow Corning).

In another variation, the invention provides a herbicidal aqueous suspension comprising water, at least one compound of formula I, an ethylene oxide-propylene oxide block copolymer as a surfactant having a return thickening temperature as defined above of at least 45 ° C, and a suspending agent.

The invention also provides a method for combating weeds in contaminated areas or in areas where contamination could occur, which method is characterized in that the areas are treated with an effective amount of a suspension according to the invention.

These suspensions are prepared by mixing the individual components together. The particle diameter of the active ingredient in the suspension is preferably less than 5 microns, preferably at least 85% by weight of the particles have a diameter less than this limit. The particle sizes reported in this specification are measured with a Coulter * Counter. Suitably, the active ingredient of a larger particle size than the size required for the suspension is mixed with other ingredients, including an optionally present copolymer of ethylene oxide with propylene oxide, and milled to this size in, for example, a ball mill. The polycarboxylated vinyl polymer or other suspending agent may suitably be added in the form of an aqueous solution or suspension.

The suspensions according to the invention suitably comprise a total of 0.05 to 700 g / l, preferably 0.05 to 600 g / l of active ingredient.

Usually, the suspension is first prepared in the form of a concentrate suitably containing 100 to 700 g / l, preferably 100 to 600 g / l, and in particular at least 300 g / l, for example 500 g / l, of the active ingredient or all active ingredients.

For use, the concentrate is then usually diluted with water, usually so that the final concentration of the active ingredient is 0.05 to 5 g / l, preferably 0.5 to 5 g / l. However, higher concentrations may also be used, especially when the application is low volume.

The suspensions usually contain 0.5 to 50 g / l, preferably 0.5 to 35 g / l of suspending agent. In particular, the suspending agent is present in an amount of from 0.5 to 10 g / l.

Where the suspending agent is a polycarboxylated vinyl polymer, it is preferably one in which some or all of the carboxyl groups are in the form of ammonium, amine or alkali metal salts. These polymers have neutralization equivalents in the range of 71 to 800 (expressed as the number of grams of dry polymer that is neutralized with one equivalent of sodium or potassium hydroxide). 1% aqueous solutions of these polymers typically have a Brookfield viscosity (20 rpm) of less than 7 Pa.s, although after neutralizing such solutions to pH 7, their viscosity increases to 10 to 70 Pa.s. Examples of such polymers are carboxyvinyl polymers (e.g. Carbopol, especially Carbopol 941 from Goodrich Chemical Company) or acrylic copolymers containing carboxyl groups (e.g. Viscalex, especially Viscalex HV 3 ° from Allied Colloids Company).

Other suitable suspending agents are high molar polysaccharide resins obtained by fermentation of starch derived sugars. . These resins, usually molecular hooonoot, of about 2,000,000 to 50,000,000, contain reactive hydroxyl and carboxyl groups, are slightly hygroscopic, dissolve easily and perfectly in cold water to form highly viscous colloidal solutions, and swell quickly in hydrated aqueous solutions to provide in the undersized non-natural, oethixltrlpo stable solutions.

The polysaccharide resin is preferably a xanthomonas hyddooid colloid, also known as xanthan gum, which is available, for example, under the name Kelzan from Kelco Commarny. Xanthomonas hyoid The colloidal colloid is obtained by fermentation with Xanthomonas, for example Xanthomonas campus.

As used herein, the term surfactant is used in a broader sense and includes substances called emulsifiers, dispersants, and mixtures thereof; it is known to use these substances in the formulation of herbicides.

Surface. Active substances having a return temperature of concentration. at least 45 ° C, may include animic surfactants, for example, phosphoric acid molol ethers or diesters with ethoxylated fatty alcohols or salts of such esters, such as ethylene oxide condensates of alkylphenols, ethoxylated fatty alcohol sulfates, lignin sulfonates, petroleum sulphonates, sulphonated condensates of naphthalene-formaldehyde, salts of sulphonated phenol-formaldehyde condensates, or more complex sulphonates, such as sidium hydrates, for example the sulphonated oleic acid-N-molar acid condensate or disalkyl sulphonates.

The surfactants may alternatively include nonionic agents, for example, the condensation products of bridged acid esters, bridged alcohols, bridged acid amides, or alkylsubstituted phenols with ethylene oxide, esters of polyhydric alcohols with fatty acids, such as esters of salts of salts with salts. condensation products of such esters with ethylene oxide, such as pllyoxyethylenated sorbitone fatty acid esters, ethylene oxide propylene oxide block copolymers, acetylene alcohols such as 2,4,7,9-tetraethyl ethyl-D-diol, or ethoxyethyl acetylene álykoly ·

The surfactants may alternatively include catalyzing agents, for example, alkyl and / or aryl-substituted quaternary ammonium compounds such as cetyltrioethylsmonium bromide, or ethoxylated tertiary bridge amoys.

Those suspensions which do not contain an ethylene oxide block polymer with propylene oxide contain at least one surfactant, and preferably contain at least one blocker of ethylene oxide and propylene oxide or a salt of a mixture of phosphoric acid mono-ethers or diesters with ethoxylated fatty alcohols.

Preferred salts of a mixture of oonnoethers or diesters of phosphoric acid with ethoxylated fatty alcohols are those available under the designation of Croda Chemicals Limited, in particular those designated O 2 (2 moles of oleyl alcohol), 0.5 (5 moles of alrylalcohol). 0.10 (10 moles), CS 10 (10 moles of cetyl / stearyl alcohol), T 10 (10 moles of tridecanol) and ID 10 (10 moles)

Where a surfactant is used to block ethylene oxide block copolymer with propylene oxide, it is preferably a copolymer formed by adding ethylene oxide to the polyoxypropylene chain to form a polyol. Particular preference is given to those polyols which have a polyol. a polyoxypropylene chain of molecular weight. It is desirable that the polyol contain 30 to 70% by weight, for example 40 to 60% by weight, i.e. about 50% by weight, of ethylene oxide. Of these polyols, those available under the name Pluronic by Ugioe Kuhlmann are preferred, especially those designated F68, F127, L62, L103, P75, P94, P104 and P105. These are solid (F), liquid (L) or pasty (P) copolymers having a molecular weight of the polyoxypropylene moiety of 2,250 (F68), 4,000 (F127), 1,750 (L62), 3,250 (L103), 2,050 (L75) ), 2,750 (P94), 3,250 (P104 and P105) and contents. polyoxyethylene 80% (F68), 70% (F127), 20% (L62), 30% (L103), 50% (P75), 40% (P94), 40% (P104), and 50% (P105) .

It should be noted, however, that there are many other suitable surfactants which can be used. The suitability of any of these can be readily determined by determining its return temperature as described above.

The surfactant is suitably present at a level of from 0.5 to 30 wt%, preferably from 3 to 15 wt%, based on the content of the compound of formula (I).

The flocculating agent which must be present when the surfactant is a compound other than a propylene oxide block copolymer, but which may be present if the surfactant is a compound, may be any conventional deflocculating agent. Preferably, however, it is a sodium salt of an anionic sulfonated condensation product such as Dyapol DFS from Yorkshire Chemieal Limited. .

The deioculant is suitably present in the? From 0.5 to 30% by weight, preferably up to 15% by weight, based on the mono-ionic compound of the formula (I).

The suspensions may contain further compaction, water-soluble substances. as carrier, although preferably the sole carrier is water.

The suspensions may contain additives such as antifoams, for example based on silicones, for example in an amount of 0.02 to 2% by weight, based on the continuous phase, antifouling additives such as ethylene, e.g. in the range of 5 to 20% by weight. or preservatives, such as formaldehyde, for example at 0.02 to 2% by weight, based on the continuous phase.

Other pesticides, such as herbicides, insecticides, fungicides or plant growth regulators, may also be present in concentrated suspensions or in diluted formulations. It is particularly desirable to add at least one herbicide, in particular a herbicide to selectively combat weeds in sugar beet. Examples of such herbicides which can be suitably used in the maintenance of functional derivatives, for example metal salts, include phenoxyxaliphatic acids such as 2,4-D, i.e. 2,4-decilsphenoxyacetic acid, MCPA, i.e. 4-ciloric acid. 2,4,5-T, ie 2,4,5-tic acid;

2.4-DB, i.e. 4- (2,4-dichlorophnoooxa) aseleate, MCCBftj. acid ^^ - chloro-NO-methylphenoxy) mPáelná and CMPP, i.e. 2- (4-cilor-penialfenoxy) propetonová further substituted motoviny like ponuron, i.e. 3- (4-еhlorfen ^г l) -1 1-bbetna-3- (3,4-dichlorophenyl) -1-methylurea, diuron, i.e. 3- (3,4-dichlorophenoxy) -1,1-depetiyl, urea, neburon, i.e. . 3- (4-cilornoay - 1-pei0o: YR-1-iethylpočovioa, linuroo, i.e. 3- (3,4-dich0ofnoyyl) -1onei0xay 1-peilyrlP0čovina, fenuron, i.e. 1,1-diiithi ^r l -3-pherylurea, and benzothiazurone, i.e. 1- (benzothiazol-2-yl) -3-methylpropyl, a protein such as a thioazine, i.e. 2-oxo-4,6-di (ethylapino- 1,3,5-triazio, atrazio, i.e. 2-ciloro-4-ethilapino-6-esopoopylamino-1,3,5-triazio, trietazio, i.e. 2-ciloro-4-diethylapeno-6-ethaloPino-1, 3,5-triazinyl, and · propetryn, i.e. _2> 4-di (6-ioopropalaPinoI pee-hathio-1,3,5-triazinyl, DNOC, i.e. 4,6- ^ 110 ^ ^ 00-0- 0 ^ sol, PCP, ie pentachlorophenol, ioxynO1, ie 4-iydiooyaЗ, 55dododibnoonol, r ^ о ^ у / П, ie.

3,5-dibrop-4-hiadrolidinone-100-di-dichlorobenzyl, i.e. 2,6-dichloro-benzoic acid, diquat, i.e. 1,1'-enialeo-2,2'-beparidalium ion, paraquat, i.e. 1,1'-piperidazole. 4,4'-bipaoidaliol ion, 2,3,6- ^ 1 ^ 10 ^ 0 ^ 0 ^, dalapon, ie 2,2- ^ е111огргорапо ^, dic ^ both, ie 3,6 ^ 1 10 10--2 о 6 010 010 0 0 00 00 П, TCA, i.e., P0 ^ ^^, loс г ch, chlooprofip, ie esopoopyl-3-cilorferylcarbamate, barban, ie 4-cilor-but-2 -inal 3-chlornorylLkarbap0á _l EPTC, i.e. S-eniyl dipropylth0okarbfpát, butyl, i.e. S-II-etiyl isobutylie0okarbípát, diallate, i.e. S-2,3-iiеilooalal-dieiooooopylie0okabbípát, allidoеiloo, i.e. N, ^N - propachlor, i.e. 2-chloro-N-isoropya-N-phenoxyacetate, bromoacation, i.e. 5-brop-33 sec-butyl-6-menuco, α, leoacH, i.e. 3-cycloyl. 7-chloro-1H-cyclopentopyrimidin-2,4-dione, maleic acid hydrazide, methanesonic acid salts, cacodylic acid, aminotriazole, i.e. 3-amino-1,2,4-triazole, pioloram, rj. 4-amino-3,5,6 -richlorpictine, trifluralio, i.e. 2,5-dioitro-N, N-dipropo-4-trifluoromethylanine, S, S-tributylphosphorothioate, phenmedipham, i.e. 3-m- tolylkarbamoyloχyfenylklrbamát, azoles ^ id, i.e. N-isobutyl - ^ - oxo-imidazolidin-1-kabboxlmid, triallate, i.e. --2.3 _g 3-Tric-lOoralУyl-disOsoprQlyttnOaarrbιmát, cycloate,. i.e. S-ethyl-cyclohexylphenylthiocarbamite, carbetamide, i.e., b-Cetylcarbamido-ω-ω-ω-γ-ifene-γ-carbamate, diphenamide, i.e. Ν, dimethyl-dimethyl-diphenylacetamide, S-pboppl-bbutlethythiocarbamite, benfubalin, i.e. n-butyl-N-Carbon-, 6-methyl-4-trifluoromethyl-anilio, metobromuron, ie 3- (4-benzophenyl) -1-l-ethoxy-1'-methyl- Methylmethyl-pyrazone, i.e. 5-amino-4-oxo-2-phenyl-4-pyridazin-3-one, 4 '(phenylenediamine) glycine, 34 (methoxycarbonyl) phenyl-N-43,5-dimethylphenylphenylcarbamate, and The preferred herbicides are phenmedipham, pybazone, lenacil and cycloet.

The compounds of the invention may be used in series with one or more of the above herbicides.

The ratio of the total homogeneous amount of the direct compounds of the formula I to the amount of added or each additional herbicide is preferably in the range of 1: 5 to 5: 1.

Said or any other herbicide may be added to the suspension according to the invention either before or after dilution of the concentrate, if this unacceptably does not impair the stability of the concentrate.

The suspensions according to the invention, having excellent stability and comicates, maintain very well their homogeneous nature and flowability during storage and at alternating temperatures. In addition, they are distinguished by excellent dispersion in the medium used to dilute them for application. These suspensions are particularly suitable against weeds in crop plants, for example in sugar beet, sunflower, tobacco, fodder crops and crops, especially sugar beet.

The application rate is usually 0.5 and 8 kg of all compounds of the formula I per ha, for example 1 4 kg per ha.

The suspensions according to the invention can be applied before or after sowing the crops. They can be used in the erythremergent or more preferably in the prieriergenic stage.

The following examples illustrate the invention.

Peak 1 and dl

An aqueous liquid suspension endinrate is prepared from the following ingredients:

ethofer, technical, 98% purity 510 g block polymer, made of ethylene oxide with a 10,000xolrolylene chain having a molecular weight of about 2050, the polyoxyethylene constituting 50% by weight of the block polymer (Pluronic P75 ”, Ugine-Kuilmann) 15 * g sodium salt of ligoiotulfooar (Polyphon H”, Wesevaae Gopopation) 15 g silicone-based anti-emulsion emulsion (Antifoam RD ”, Dow Gorning Corporation) 0.5 g nthnlnoglnaol80 g xanrhantine resin ( Keezan, Kelco Co.) 2 g ftrilldehyde 1 g water to make up to a volume of 5 liters approx. 510 ml

360 ml of water, antifoam emulsion (Antifoam RD, block copolymer (Pluronic P75), sodium ligoiotulfooar (Polyfon H), n-nylnoline and ethofumesate) are introduced into a moving ball mill in succession. The mixture is milled for more than 95% by weight The ethofumesate has a particle size below 5 microns, as determined by a Coulter counter, then a solution of xanthan resin and formaldehyde (a preservative for xanthan resin) in 150 ml of water is added to the mill mixture, which is then mixed using a paddle stirrer until homogeneous. The pH of the suspension is then adjusted to 7.0 by addition of 10% aqueous hydrochloric acid.

Example 2

In a manner analogous to that described in Example 1, a liquid herbicidal concentrate of the same composition was prepared except that 2.5 g was used instead of xanthan resin and formaldehyde. Carbopol 941 carboxyvinyl polymer (Goodrich Chemical Compaq). As in Example 1, sodium salt was added from water, antifoam emulsion (Antifoam RD), block copolymer (Pluronic P75). ligoinsulfooate (Polyfon H), ethylene glycol and ethofumesate are prepared by suspensions. The pH of this suspension is adjusted to 7.0 by the addition of 10% aqueous hydrochloric acid, and then the solution of the carboxyvinyl polymer of Carbopol 94.1 is dispersed homogeneously in the suspension. The pH of the slurry was again adjusted to 7.0 by the addition of 10% aqueous sodium hydroxide.

Example 3

In a similar manner to that described in Example 1, a liquid herbicidal concentrate of the same composition was prepared, but the xanthan resin and formaldehyde were replaced with 32 g of an emulsion containing 30% carboxylic acid-containing acrylic copolymer (Viscalex HV 30 - Allied Cooid MannUaaCuring Company). The pH of the suspension was adjusted to 8.0 by addition of 10% aqueous hydrochloric acid.

Example 4

For comparison, suspension concentrates identical to those of Examples 1, 2 and 3 are prepared, but the suspending agent (i.e., xanthan resin, carboxyvinyl polymer [Carbopol 94l] and containing 30% acrylic copolymer containing) is always omitted carboxyl groups [Viscalex HV 30]).

Example 5

Also for comparison, suspension concentrates identical to those of Examples 1 to 3 were prepared, but instead of a block copolymer of ethylene oxide with propylene oxide (Pleuronic P75) g of lauryl alcohol condensate with 6 moles of ethylene oxide (Serfal LA 60, DG Bennet Chemicals Limited). Serfal LA60 is characterized by a return temperature as defined above, starting at 45 ° C.

Example 6

Suspension ^{kOlccenClrá,} those of Examples 1, 2 and 3 was compared to suspension concentrates of Examples 4 and. 5 comparative test involving storage at various temperatures (in one test, the temperature was kept at 40 ° C during the next test after for 6 months alternately every 12 hours at 12 ° C and 38 ° C). At the end of the storage period, it is found that the suspensions of Examples 1, 2 and 3 do not form a hard sediment and the suspensions are still liquid, while the suspensions of Example 4 settle to form a hard sediment and approximately 50 vol% clear liquid above the sediment. In addition, it has been found that the pellet cannot be re-dispersed in a liquid found above the pellet by methods that can be used by the consumer, including mixing and shaking.

At the end of the storage tests, the suspensions of Example 5 were no longer liquid; furthermore, no methods which can be used by the consumer, including mixing and shaking, can be used anymore.

Example 1 and <17

Aqueous liquid suspension concentrates are prepared, identical to those of Examples 1, 2 and 3, except that the block copolymer (Pluronic P75) is replaced by 50 g of sodium anionic sulfonated condensation product (Dyapol PFS) and 5 g of salts of a mixture of mooosters or phosphoric acid diesters. with fatty alcohol alcohols (Crodafos T10, Croda Chemicals Limited). All of these suspensions remain liquid and do not form hard and clear liquid above the grounds as described in Example 6.

Example

Aqueous liquid suspension ends prepared as described in Examples 1, 2, 3 and 7 were prepared, except that the technical ethofumesate was replaced by the sunny amounts of the compounds listed below, which represent a preferred class of compounds for the compositions of the present invention. of the invention to achieve a concentration of 500 g / l of the compound itself.

2-Ethoxy-2,3-dihydro-3,3-dihydro-pentafluoro-yl-ethanesulfonate, 2-Inorolino-2,3-dihydro-3,3-diethylbenzofulan-5-yl-ethaneculfonate, 2-piperidios-2 3-dihydro-3,3-diethylbeta-phenylrao-5-yl-ethanesulfonate, 2-oxo-2,33-dihydro-3,3-dihydro-3-dihydroxybenzenesulfonate, 2-acetyloxy-2,3-iihydro-3,3-diethylbenzenesulfanate --5 ieΠhancuSfonát-yl, 2-ethoxy-2,3diihdirOd3,3 iiiethylbeozofuran-5ddl iethylaiincsulfonnt-2-ethoxy-2-dihydro-3, 3-iiieΠhylbenczOusan yldiiiethdlaiincsuSfsnát-5-ethoxy-2 _{J-2,3ddihdirOd3 >} · 3ddiiethylbeozofurand 5dyl iethyl-N-N-acetdlamioosulfonát 2-ethzxy 2,3diihdirOd3,3diiiethdlbeozzfurat-dl-5-N-N-ieehyd dhllracetylaiincsulfznOt, 2-propoxy-2,3-dihddro-3, 3-dimethylbnnzoflrao -5ddl iethdlaiintsuufonát-2-propoxx-2 2 3-iihydrs 3,3diiiethdlbenzzfuran-5-ylddiiethdlaiinzsulfonát 2-iuoprspoxy-2,3-dihydro-3,3-dl-dimethylbenzzflraOd5 iet d ^ ^r laiinosulfonát 2-iuspropzxy -2,3-β-β-3,3-cyclomethylbenzofuran-5-di-diethylsulphine sulphate, 2-alldloxyl-2,3-dihydroxy-3,3-iiie ELH ^г lbenzzSur an-5-yl iethylaIninosuSfonát 2-alldlsxd iihydrz-2,3-3,3-iiiethdlbenzzfuran 5-d1-iiiithdlaminosulfznOt, 2-prspΘrgdlsxd 2,3diihydrSd3,3-diiethdlbenzsflraOd5dyl iethdlaiinzsulfsnát-2-prspargyloxy -2,3-dihydro-3,3-diethyldibenzofuran-5-yldiethylamino-sulfonate, 2-isobenzoyl-2,3-methyl (2,3-ethoxybenzofuran-5-yl) ethylaminosulphonate, 2-2, 2-zebosulfonate 3-iihydrz-3,3-dimethyl-thylbeozzfurao 5dd1-iiietlh ^г lamicosulfonná.

After storage, as described in Example 6, all suspensions remain liquid and no hard sediment or clear liquid is formed above the liquid.

Example 9

Determination of the return temperature

A mixture of ground technical ethofumesate with a purity of 98% in quantity! 1020 g, 100 g of sodium anionic sulfonated condensation product (DyapoZL PFS, Yzokshire Chemiiais Limited) as deflocculating agent, 2 g of silicone-based antifoam (AaCífoam RD, Dow Corning) and 844 ml of water are milled for 5.5 hours, thereby a milk consistency suspension having a density of 1.12 is obtained. To 8.5 ml of this suspension was then added 1.5 ml of a 10% aqueous solution condensed with 10 ml of ethyl leoxide (Renex 690, Atlas Claemical Industies Co.) as a surfactant. The mixture is then slowly heated in a water bath at which temperature is maintained. At 45 ° C, the slurry thickens considerably and can be easily ignored. When the slurry is heated further, it remains in this state, but when it is cooled below 45 ° C, it returns to its original ionic reaction. Thus, the return temperature of the nonylphenol condensed with 10 moles of thioxydione (Renex 690) is 45 ° C.

201039 8 Other surfactants are also evaluated in this way: achieved u some of which are: ethylene oxide block copolymer paste with Propylene oxide of molecular weight weight of the polyoxypropylene portion 2 050 and of a poly (oxyethylene) content 50% Pluronic P 75 Mp> 62 ° C dtto 4 000 70% (Pluronic Fri 27) Mp> 62 ° C dtto 3 250 50% Pluronic P 105 68 ° C dtto 2 750 Pluronic P 94 40% 68 ° C dtto (liquid) 3 250 (Pluronic L 103) » 30%. 68 ° C dtto (rigid) 1 750 Pluronic F 68 80% Deň: 32 ° C dtto (liquid) 1 750 (Pluronic L 62) 20% Deň: 32 ° C phosphoric acid ester with 10 moles of ethoxylated tridecanol (Crodafos T 10) Deň: 32 ° C with 10 moles of ethoxylated isodecanol (Crodafos ID-10) High: 34 ° C dtto - with 2 moles of ethoxylated oleyl alcohol (Crodafos 02) High: 34 ° C dtto - with 5 moles of ethoxylated oleyl alcohol (Crodafos 05) 60 ° C dtto - with 10 moles of ethoxylated oleyl alcohol (Crodafos 010) Deň: 32 ° C dtto - with 10 moles of ethoxylated cetyl / stearyl alcohol (Crodafos CS 10) Deň: 32 ° C nonylphenol condensed with 12 moles of ethylene oxide (Renex 30) Deň: 32 ° C lauryl alcohol condensate with 6 moles of ethylene oxide (Serfal LA 60) Deň: 32 ° C dtto - with 5 moles of ethylene oxide (Serfal LA 50) Deň: 32 ° C

SUBJECT OF THE INVENTION

Claims (8)

A herbicidal composition comprising from 0.05 to 700 g / l of a substituted benzofuran herbicide of the general formula I, wherein: R ⁴ ethoxy, propoxy or isopropoxy and 5 9 9 R group of the formula -SO ₂ R 'where R represents a methyl or ethyl group, provided that the compound has a melting point at least 50 ° C and a solubility in water at 25 ° C at most 0.1%, wherein at least 85 wt% The particles of this compound have a diameter of less than 5 µm as measured by a Coulter Counter, characterized in that the herbicidal composition is an aqueous suspension containing as suspending agent 0.5 to 50 g / l of xenthomonas hydrophilic colloid and 0.5 to 30 wt. to a weight amount of a compound of Formula I, block copolymers of ethylene oxide with propylene oxide as a surfactant, having a return thickening temperature of at least 45 ° C. 2. A composition according to claim 1, wherein:. that. as a suspending agent it comprises a polycarboxylated vioyl ‘polymer in which at least a part of the carboxyl groups are in the form of an ammonium salt or an amino or alkali metal salt. 3. The herbicidal composition as in points 1 or 2,. characterized in that it contains as a surfactant a block copolymer of ethylene oxide with propylene oxide either alone or in admixture with another surfactant. 4. The herbicidal composition of claim 1 comprising water, at least one compound of formula I, an ethylene oxide-propylene oxide block copolymer as a surfactant and a suspending agent. 5. The herbicidal composition of claim 3 or 4, wherein the surfactant comprises a block copolymer of ethylene oxide with propylene oxide which is a polyol obtained by adding ethylene oxide to the polyoxypropylene. wherein the polyoxypropylene chain has a molecular weight greater than 1,500. 6. The composition of claim 5, wherein the composition is as follows. the surfactant comprises a block copolymer of ethylene oxide with propylene oxide containing from 30 to 70 mol% of ethylene oxide. 7. The fungicidal composition of items 1 to 2. 6, comprising at least 100 g / l of the compound or compounds of formula I. 8. A fungicidal composition according to any one of Claims 1 to 7, characterized in that it contains 2-methyl-2,3-dihydro-3,3-dimethylimidazofuran-5-yl-oetholalkylsulfate as the active ingredient or as one of the active ingredients of the formula (I). .