GB2169806A

GB2169806A - Herbicidal mixtures based on n-(phosphonomethylglycyl)sulphonylamine

Info

Publication number: GB2169806A
Application number: GB08601468A
Authority: GB
Inventors: Albert Bertrand; Guy Borrod
Original assignee: Rhone Poulenc Agrochimie SA
Current assignee: Bayer CropScience SA
Priority date: 1985-01-23
Filing date: 1986-01-22
Publication date: 1986-07-23
Also published as: HU200897B; GR860116B; KR860005586A; DE3663436D1; CA1272890A; EP0192583B1; DK32986A; FR2576181A1; DK32986D0; PT81890A; NZ214880A; AU5259586A; NO860188L; MA20611A1; EP0192583A1; FR2576181B1; HUT40307A; GB8601468D0; BR8600228A; OA08194A

Abstract

A herbicidal composition comprises (A) an active herbicidal substance of formula: <IMAGE> in which: R<1> denotes an optionally substituted hydrocarbon radical; R denotes a hydrogen atom or is as defined for R<1>; R<2> and R<3>, which may be identical or different, denote hydrogen atoms or are such that OR<2> and OR<3> are hydrolysable groups, or a salt thereof; and (B) at least one active herbicidal substance which is a chloroacetamide, triazine, phenylurea, thiadiazolylurea, sulphonylurea, benzothiazolylurea, nitroaniline, phenoxynicotinanilide, amide, oxadiazole, aminotriazole, picolinic acid, phenoxybenzoic acid derivative, phenoxypropionic acid derivative, aryloxy acid, benzoic acid, propionic acid, triazinone, carbamate, pyridazinone, pyridone, guaternary ammonium compound, uracil, hydroxybenzonitrile or imidazolinone or a salt thereof.

Description

1 GB2169806A 1

SPECIFICATION

Herbicidal mixtures based on a compound of the N(phosphonomethyfglycyi)sulphonylamine type The present invention relates to new herbicidal compositions containing herbicidal mixtures of one herbicide of the N- (phosphonomethyigylcyi)sulphonylamine chemical family, as well as to the application of these herbicidal compositions in agriculture.

Many compounds are known which possess an aminomethylphosphonic group and have herbi- dical properties, in particular in French Patents 2,129,327, 2,281,375, 2, 251,569, 2,413,398 10 and 2,463,149, European Patents 53,871, 54,382 and 73,574, US Patents 3, 160,632, 3,455,675, 3,868,407, 4,388,103 and 4,397,676, British Patent 2,090,596, World Patent WO 83/03608 and Belgian Patents 894,244, 894,245, 894,590, 894,591, 894,592, 894,593, 894,594 and 894,595.

It is, however, always desirable to broaden the field of available herbicidal compositions, in order to meet more fully all the needs of farmers. Some amides possessing an aminomethyl phosphonic group are known, but these products are either of low activity or inactive.

It is is also desirable to have herbicidal compositions which are strong and rapid in their activity, and which have good biodegradability.

An object of the present invention is to provide post-emergence herbidical compositions 20 possessing a broad spectrum of activity, which have at least partially a descending systemic effect and are possibly selective for certain crops.

A further object of the invention is to provide herbicidal compositions which have persistence in the soil, in particular sufficient persistence to act against staggered sproutings (i.e. against weeds and other plants, the growth and development of which are spread out over a period of 25 time).

It has now been found that these objects may be attained, in whole or in part, by means of the compositions according to the invention.

The present invention provides herbicidal compositions comprising (A) an active substance of formula:

OR 2 1 1 0 = P - CH 2 - NH - CH 2 - CO - N - SO 2 - R (I 1 3 1 OR R in which:

R' denotes an optionally substituted hydocarbon radical, in particular an alkyl, aryl or cycloalkyl 40 radical, each of which may be substituted; suitable substituents include halogen atoms and phenyl, cyano, alky], alkoxy, and alkyl carboxylate groups, in which the alkyl groups and moieties preferably have 1 to 4 carbon atoms; R' generally has from 1 to 18 carbon atoms, preferably from 1 to 7 carbon atoms and more especially from 3 to 7 carbon atoms when it is a cycloaklyl group; it is most preferably an akyl radical having from 1 to 4 carbon atoms, which may optionally be halogenated, in particular chlorinated or fluorinated, for example CF, R denotes a hydrogen atom or has one of the meanings given for R', and is preferably an alkyl group having 1 to 4 carbon atoms, R2 and R3, which may be identical or different, denote a hydrogen atom or are such that OR2 and OR3 are hydrolysable groups; R2 and R3 can be, in particular, alkyl or aryl radicals, preferably alkyl 50 or phenyl radicals, which are optionally substituted; suitable substituents are those specified in the definition of R'; R2 and R3 generally have from 1 to 12 carbon atoms, and preferably have from 1 to 8 carbon atoms, or a salt thereof, in particular the salts of the P-OH groups and those of the nitrogen atom of the NH group, which then becomes an ammonium group, especially the agriculturally acceptable salts of these products, for example the salts with alkali metals, in particular sodium and potassium, alkaline earth metal salts, primary, secondary, tertiary or quaternary ammonium salts and sulphonium salts, addition salts with acids, such as chlorides, sulphates, phosphates and other salts derived from acids having a pK value of less than or equal to 2.5; and B) at least one active substance which is a chloracetamide (in particular alachor or metolachlor), triazine (in particular simazine, atrazine or prometryne), phenylurea (in particular diuron, isoproturon or linuron), thiadiazolylurea (in particular tebuthiuron or ethidimuron), sulphonylurea (in particular sulforneturon, chlorsulfuron or metsulfuron), benzothiazolylurea (in particular metha benzthiazuron), nitroaniline (in particular oryzalin or trifluralin), phenoxynicotinanilide (in particular diflufenican), amide (in particular napropamide or propanil), oxadiazole (in particular oxadizon or 65 2 GB2169806A 2 dimefuron), aminotriazole, picolinic acid (picloram), phenoxybenzoic acid derivative (in particular bifenox, acifluorfen, acifluorfen-sodium, fomesafen, oxyfluorfen or an ester of acifluorfen and an aliphatic alcohol, glycolate or lactate, phenoxypropionic derivative (in particular quizalofop-ethyl or fluazifop-butyl), aryloxyacid (in particular 2,4-13, 2,4-13P, MCPA or MCPP), benzoic acid (in particu lar dicamba), propionic acid (in particular dalapon), triazinone (in particular metribuzin), carbamate 5 (in particular cabertamide, EPTC or asulam), pyridazinone (in particular norflurazon), pyridone (in particular fluridone), quaternary ammonium compound (in particular diquat or paraquat), uracil (in particular bromacil), hydroxybenzonitrile (in particular bromoxynil or ioxynil) or imidazolinone (in particular imazaquin or imazapur).

Among the compounds of formula (1), the preferred compounds are those in which R and R' 10 are each an alkyl group having from 1 to 4 carbon atoms, and R2 and R3 are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or a phenyl group, as well as the salts of these compounds: R2 preferably represents hydrogen.

Among the compounds of the group B), the preferred compounds are, if good persistance is sought: simazine, atrazine, prometryne, diuron, chlosuffuron, oryzalin, napropamide, oxadiazon, 15 dimefuron, picloram, fomesafen, bromacil and imazaquin.

The compounds of formula (1) can be prepared, for example, according to the procedure described in European Patent Application No. 135,454.

The compounds of the group B) include known compounds most of them being described in detail in works such as---ThePesticide Manual- published by---TheBritish Crop Protection Council-, the 7th edition of which dates from 1983. The chemical names of most of the products of the group B) used in the Examples are given in Table (R).

The compositions according to the invention are generally of the binary type (a single cornpound of formula (1) and a single active substance of the group B)) but ternary combinations (eg two active substances of the group B)), quaternary combinations (eg three active substances of 25 the group B)) or others can be used.

The ratio by weight of active substance of formula (1) relative to the active substance of the group B) is generally from 0.2A to 10A, and is preferably from 0.25:1 to 4:1; this ratio can, however, be higher, e.g. 100A, when active substances such as picloram and, in particular, sulphonylureas are used.

The Examples in this specification are given to illustrate how compositions according to the invention can be produced and employed; except where otherwise stated, the percentages are percentages by weight; the terms pre-sprouting and pre-emergence are synonymous. The same applies to the terms post-sprouting and post-emergence.

In practice the compositions according to the invention usually contain a solid or liquid carrier 35 which is agriculturally acceptable and/or a surfactant which is also agriculturally acceptable. In particular, the usual inert supports and usual surfactants can be used.

These compositions can also contain other ingredients, e.g. protective colloids, adhesives, thickeners, thixotropic agents, penetrants, stabilizers and sequestering agents as well as other known active substances possessing pesticidal (in particular insecticidal, fungicidal or herbicidal) 40 properties or possessing plant growth regulatory properties. More generally, the compounds used in the invention can be combined with solid or liquid additives corresponding to the customary techniques of preparing formulations.

The proportions of active substances used in the compositions of the present invention can vary within wide limits according to the nature of the weeds to be eliminated and the degree of 45 infestation of the loci which have to be cleared of weeds.

In general, the compositions according to the invention usually contain 0. 05 to 95% of active substance (formula (1) and group B)], approximately 1% to 95% of one or more solid or liquid carriers and optionally approximately 0.1 to 50% preferably 5 to 40%, of one or more surfac tants.

In the present disclosure, the term -carrier- denotes an organic or inorganic natural or synthetic material with which the active substances are combined to facilitate their application on the plant, on seeds or on the soil. This carier is hence generally inert and it must be agricultu rally acceptable, in particular on the treated plant.

As solid carriers (or fillers), inorganic or synthetic fillers may be mentioned, e.g. kaolin, 55 attapulgite, montmorillonite, bentonite, talc, fuller's earth, diatomaceous earth, kieselguhr, calcium and magnesium carbonates, precipitated synthetic silica, alumina, alkali metal silicates and sili coaluminates, resins, waxes and solid fertilizers. Water-soluble fillers, e.g. sodium sulphate or ammonium sulphate and urea, can also be used.

As liquid carriers, there may be mentioned water, alcohols (in particular butanol), esters (in 60 particular methylgylcol acetate), ketones (in particular cyclohexanone and isophorone), petroleum fractions, aromatic hydrocarbons (in particular xylenes) or paraffin hydrocarbons, chlorinated aliphatic hydrocarbons (in particular trichloroethane) or chlorinated, aromatic hydrocarbons (in particular chlorobenzenes), and water-soluble solvents such as dimethylformamide, dimethyl sul- phoxide and N-methylpyrrolidone.

3 GB2169806A 3 The surfactant can be an emulsifying agent, dispersant or wetting agent of the ionic or nonionic type, or a mixture of such surfactants.

As nonionic wetting agents, there may be mentioned ethylene oxide-treated alkylphenols (in particular octyi-, nonyi- and tributylphenols having 6 to 18 oxyethylene units), ethylene oxide treated fatty alcohols (in particular C,() to C,, alcohols having 6 to 18 oxyethylene units), ethylene 5 oxide-treated fatty amines (in particular tallow amine or tall oil having from 2 to 4 oxyethylene units), and esters of fatty acids and polyols (of the glycerine type or sugar type) which have been treated with ethylene oxide (in particular sorbitan laurate and stearate having 5 to 20 oxyethylene units).

As wetting agents, there may be mentioned alkyinaphthalenesulphonate ester salts (in particu- 10 lar sodium or potassium isopropyl-, buty]- and dibutyinaphthalenesulphonates), sulphate ester salts of fatty alcohols (in particular sodium or potassium lauryl sulphate), sulphosuccinate ester salts of fatty alcohols (in particular sodium or potassium dioctyl sulphosuccinate), and taurine derivatives (in particular alkyltaurates, aryi-N-methyitaurides and sodium oleyimethyltauride).

As nonionic dispersants, there may be mentioned ethylene oxide-treated arylphenols [in parti- 15 cular bis and tris(phenylethyl) phenols containing 18 to 40 oxyethylene units].

As anionic dispersants, there may be mentioned salified polycarboxylic polymers (such as sodium polycarboxylate and polyacrylate polymers), polycondensates of formaldehyde and diphenoisulphonates or alkyinaphthalenesulphonates (in particular sodium methyinaphthalenesulphonate), phosphoric acid ester salts or acid esters of ethylene oxide-treated alkyl- or arylphenols [in particular phosphoric esters of nonylphenols having 6 to 18 oxyethylene units, in acid form or potassium salt form, as well as phosphoric esters of bis- or tris(phenylethyl) phenol having 18 to 40 oxyethylene units, in acid or salt form], phosphated ethylene oxide- treated fatty alcohols (in particular C,, to C, fatty alcohols having 6 to 18 oxyethylene units), and alkali metal or alkaline earth metal lignosulphonates.

The compositions according to the invention, especially when they are in the form of dry flowables, can also contain a. natural or synthetic binder preferably in a proportion of 1 to 50% by weight relative to the weight of the total composition.

As a natural binder, there may be mentioned starch and its derivatives (in particular modified starch and dextrin), cellulose derivatives (in particular carboxymethylcellulose, hydroxyethylcellu- 30 lose and hydroxypropyimethylcellulose), sugars (e.g. lactose, mannitol and sorbitol) and gums (e.g. gum arabic and xanthan gums).

As a synthetic binder, there may be mentioned polymers (in particular polyvinyl alcohol, polyvinyl acetate, polyvinylpyrrolidone and alkali metal polyacrylates), polycondensates (especially polyethers such as polyglycols; copolycondensates of maleic anhydride; polycondensates of 35 formaldehyde and alky[naphthalenesulphonates (e.g. the polycondensate of formaldehyde and sodium methyinaphthalenesulphonate) and alkali metal lignosulphonates.

The presence of at least one surfactant in the compositions according to the invention is generally essential when the active substances and/or inert carrier are not soluble in water and when the vector agent for the application is water.

For their application, the compositions according to the invention may be in solid or liquid form; these forms are relatively dilute. The compositions which are suitable for transportation, marketing and storage, are, on the whole, concentrated compositions.

As solid forms of compositions, there may be mentioned wettable powders and powders for dusting (with a content of active substances which can range up to 100%) and pellets (prefera- 45 bly dry flowables) in particular those obtained by extrusion, by compaction, by impregnation of a granulated carrier and by granulation starting from a powder, the content of active substances of formula (1) and group B) in these pellets preferably being between 0.5 and 80% for these latter cases.

As liquid forms of compositions, or forms intended to make liquid compositions at the time of 50 use, there may be mentioned solutions and flowables, or alternatively pastes. Concentrated compositions in the solid state are preferred.

The flowables, which can be applied by 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 substances, from 0.5 to 15% of surfactants, from 0.1 to 10% of thixotropic agents, from 0 to 55 10% of suitable additives, e.g. antifoams, corrosion inhibitors, stabilizers, penetrants and adhe sives, and, as a carrier, water or an organic liquid in which the active substances are of low solubility or insoluble: certain organic solid substances or inorganic salts can be dissolved in the carrier to assist in preventing sedimentation, or as antifreeze for the water.

By way of example, a flowable composition is as follows (Example l):

4 GB2169806A 4 active substances 500 g polycondensate of ethylene oxide with tristyrylphenol phosphate 50 g - polycondensate of ethylene oxide with 5 alkylphenol 50 g - sodium polycarboxylate 20 g - ethylene glycol (antifreeze) 50 g - organopolysiloxane oil (antifoam) 1 g - polysaccharide (thickener) 1.5 g 10 - water 316.5 g According to this Example 1, compositions can be produced with, in particular, the following products:

Products of formula (I):

Compound No. 1: compound of formula (1) in which R and R' are both methyl groups and R2 and R3 are both hydrogen atoms, Compound No. 2: compound of formula (1) in which R and R' are both methyl groups, R2 is a hydrogen atom and 113 is a phenyl group; Compound No. 3: compound of formula (1) in which R and R' are both methyl groups and R2 20 and R3 are both phenyl groups.

Products of group (B): simazine, atrazine, prometryne, diuron, isoproturon, linuron, metabenzthi azuron, oryzalin, trifluralin, diflufenican, napropamide, propanil, oxadiazon, aminotriazole, picloram, bifenox, acifluorfen-sodium, quizalofop-ethyl, 2,4-D, MCPA, MWP carbetamide, asulam, bromox yni, ioxynil.

According to Example 1, Examples 2 to 10 are produced as defined in the following Table (I):

TABLE (I)

Example Amount in grams Nature and amount in of one of the com- grams of compounds pounds Nos. 1 to 3 of the group B) 2 1 300 Atrazine 200 (No. 11 3 (No. 2) 250 Oryzalin 250 4 (No. 1) 450 Diflufenican 50 (No. 2) 350 Oxadiazon 150 6 (No. 2) 250 Aminotriazole 250 7 (No. 3) 300 Bifenox 200 8 (No. 1) 350 Acifluorfen Na 150 9 (No. 3) 250 Asulam 250 (No. 1) 350 Bromoxynil 150 i Wettable powders (or powders for spraying) and dry flowables are the preferred compositions according to the invention. The wettable powders usually contain 20 to 95% of active substances and they usually contain, in addition to the solid carrier, from 0 to 25% of a wetting agent, from 1 to 15% of a dispersant and, when necessary, from 0 to 10% of one or more stabilisers and/or other additives e.g. penetrants, adhesives, anti-caking agents and colorants. By way of example, various wettable powder compositions are as follows:

GB2169806A 5 Example 11: - active substances - calcium lignosulphonate (deflocculant) - isopropyinaphthalenesulphonate (anionic wetting agent) anti-caking silica - kaolin (filler) 50% 5% 1% 5% 39% 10 Example 12:

- active substances 80% - sodium alkyinaphthalenesulphonate 2% - sodium lignosulphonate 2% 15 - anti-caking silica 3% - kaolin 13% 20 Example 13:

- active substances 50% - sodium alky[naphthalenesulphonate 2% methylcellulose of low viscosity 2% - diatomaceous earth 46% 25 Example 14:

- active substances 90% - sodium dioctyl sulphosuccinate 0.2% - synthetic Silica 9.8% Example 15:

- active substances 400 g - sodium lignosulphonate 509 - sodium dibutyl na phthalenesu 1 phonate 10 g - silica 540 g 40 Example 16:

- active substances 250 9 45 - isooctylphenoxy(polyoxyethylene)ethanol 25 g - mixture of equal parts by weight of whiting and hydroxyethylcellu lose 17 g - sodium aluminosilicate 543 g - kieselguhr 165 g 50 Example 17:

- active substances 1009 55 - mixture of sodium salts of saturated fatty acid sulphates 30 9 - condensation product of naphthalene sulphonic acid and formaldehyde 50 9 - kaolin 8209 60 6 GB2169806A 6 Example 18:

- active substances - sodium isopropyinaphthalenesulphonate 5 - sodium lignosulphonate - precipitated silica - kaolin q.s.

40% 2% 5% 10% 100% Example 19: - active substances - sodium lauryl sulphate - tris(phenylethyl)phenol containing 40 oxy- 40% 4% ethylene units 6% 15 - precipitated silica 15% - attapulgite q.s. 100% 20 Example 20:

- active substances 40% - tallow amine containing 25 oxyethylene units 10% - Cl, alcohol containing 6 oxyethylene units 5% - precipitated silica 15% 25 - attapulgite q.s. 100% Example 2 1: 30 - active substances 50% sodium oleyimethyitauride 2% - sodium methyinaphthalenesulphonate poly condensed with formaldehyde 4% - diatomaceous earth 20% 35 - kieselguhr q.s. 100% Example 22: 40 - active substances 50% - nonylphenol containing 18 oxyethylene units 2% - nonylphenol phosphate containing 10 oxy ethylene units 4% - precipitated silica 10% 45 - montmorillonite q.s. 100% Example 23: 50 - active substances 60% - sodium dioetyl sulphosuccinate 2% polycondensed sodium methyinaphienesulphonate 3% - sodium silicoaluminate 15% - kaolin q.s. 100% 55 7 GB 2 169 806A 7 Example 24: - active substances sorbitan stearate (stearate of dehydrated 5 sorbitol) containing 25 oxyethylene units - phosphated tris(phenylethyi)phenoi containing 18 oxyethylene units - precipitated silica - kieselguhr q.s.

60% 5% 3% 10% 100% Example 25: - active substances - sodium oleyimethyitauride phosphated tris(phenylethyl)phenol containing 18 oxyethylene units silica kaolin q.s.

60% 2% 3% 15% 100% Example 26: - active substances - sodium isopropyinaphthalenesulphonate - condensed sodium methyinaphthalenesulphonate - synthetic silica - kaolin q.s.

80% 2% 3% 15% 100% Example 27:

active substances 80% sodium lauryl sulphate 3% - sodium polycarboxylate 3% - sodium silicoaluminate q.s. 100% In these Examples 11 to 27, one of the compounds used as an active substance is compound No. 1, 2 or 3 and the other is simazine, atrazine, prometryne, diuron, isoproturon, linuron, metabenthiazuron, trifluralin, diflufenican, napropamide, oxadiazon, dimefuron, bifenox, quizalofop- 40 ethyl_dalapon, carbetamide or another active substance mentioned in Table (]V).

Examples 30 to 41 are defined in Table (11). The mixtures given in Table (V) can also be used.

8 GB2169806A 8 TABLE (11)

A D Ex- Composition Amount in grams Nature and amount in ample derived from (or percentage) of grams (or percentage) Examples 11 one of the compounds of compound of the to -17 1 to 3 group B) 11 (No. 1) 30% Atrazine 207, 31 12 (No. 2) 50% Diuron 30% 13 32 (No. 3) 30% Simazine 20% 14 33 (No. 3) 60% Dimefuron 30% 11 34 (No. 2) 25% Isoproturon 25% 16 (No. 3) 150 g Bifenox 100 9 36 is (No. 1) 200 9 Napropamide 20 37 12 (No. 1) 55% Oxadiazon 25% i 38 17 (No. 2) 85 9 Quizalofop- 15 9 ethyl 39 13 (No. 2) 20% Carbetamide 30% 15 (No. 3) 300 9 Diflufenican 100 a 1 41 14 (No. 1) 30% Dalapon _ 1 60% 1 To obtain powders for spraying or wettable powders, the active substances are intimately mixed in suitable blenders with the additional substances, or the porous filler is impregnated with the molten active substances and the ground with suitable mills or other grinders. Powders for 45 spraying which have advantageous wettability and suspendibility are thereby obtained; they can be suspended in water at any desired concentration and this suspension can be very advantage ously used, especially for application on plant leaves.

The "dry flowables" (more precisely, these are pellets which can be easily dispersed in water) are substantially similar in their composition to the wettable powders. They can be prepared by 50 granulation of formulations described for the wettable powders, either by a wet method [bringing the finely divided active substances into contact with the inert filler and with a little water, e.g.

1 to 20%, or a little of an aqueous solution of dispersant or binder (described above), followed by drying and sieving] or by a dry method (compaction followed by grinding and sieving).

By way of example, a few dry flowable formulations are as follows:

Example 50:

- active substances 800 g sodium alkyInaphthalenesulphonate 209 - sodium methylenebis(naphthalene)sulphonate 809 - kaolin 100 g 9 GB2169806A 9 Example 5 1:

- active substances - tallow amine containing 25 oxyethylene units 5 precipitated synthetic silica - polyvinylpyrrolidone - bentonite q.s.

Example 52: - active substances C,., alcohol containing 6 oxyethylene units precipitated synthetic silica 15 ammonium sulphate hydroxyethylcellulose - starch q.s.

Example 53: - active substances - nonylphenol containing 10 oxyethylene units - calcium lignosulphonate 25 - polyvinylpyrrolidone - kaolin q.s.

40% 10% 10 g 5% 100% 40% 5% 5% 20% 2% 100% 40% 2% 10% 5% 100% The exact examples of active substances and special proportions to be produced according to these Examples 50 to 53 are similar to those for the mixtures of active substances in Tables (11) and (V).

In place of the wettable powders, pasts can be produced. The conditions and procedures for the production and use of these pastes are similar to those for the wettable powders or powders for spraying.

The aqueous dispersions and emulsions, e.g. the compositions obtained by diluting with water a wettable powder of a flowable according to the invention, are included within the general 35 scope of the compositions which can be used 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, aqueous emulsions or mixtures can be applied to the areas or crops to be cleared of weeds by any suitable means, mainly by spraying, at doses which are generally of 40 the order of 50 to 1,200 litres of mixture per hectare, and preferably from 80 to 250 1/ha.

According to one method according to the invention the compounds of formula (1) and the group B) are applied to the areas to be cleared of weeds in a single application; mixing of the two active substances can be carried out beforehand with dilution of the concentrate with water at the time of use, or extemporaneously by mixing two active substances or concentrates of active substances directly in the water which is to serve for the application.

According to another method of the invention the compound of formula (1) and the compound of the group B) are applied sequentially: and the latter compounds can then optionally be applied on the soil. Thus, the invention also provides a two component pack comprising a first compo nent which comprises a herbicidally active substance of formula (1) as hereinbefore defined and a 50 second component which comprises at least one herbidically active substance of group B) as hereinbefore defined which can be applied simultaneously or separately. When sequential treat ments are performed, the application intervals between the two treatments is advantageously from 1 to 3 weeks, and the compound of group B) can sometimes be applied first.

Thus to apply compounds of group B) which possess pre-sprouting activity, it is possible to 55 use, in the invention, pellets which are intended to be placed on the ground.

The present invention also provides a method of combating weeds at a locus which comprises applying thereto an effective amount of a composition according to the invention.

The compositions according to the invention are conveniently applied on vegetation, and in particular on the weeds to be eliminated when the latter posses a green foilage.

The herbidical compositions and the application thereof can also be employed shortly before harvesting, so as to kill the weeds, the roots of which persist in the soil after harvesting. It is thereby possible to sow very quickly after harvesting without the need to perform mechanical weed clearing operations (eg tilling).

In general, the compound of formula (1) is applied at doses of between 0. 1 and 10 kg/ha, 65 GB2169806A 10 preferably between 0. 1 and 6 kg/ha and especially between 0. 1 and 4 kg/ha. The preferred levels of application for the other active substances are given below.

Thus, when a triazine, e.g. atriazine, is used, it is preferably applied at between 0.125 and 4 kg/ha, the weight ratio of the compound of formula (1) to the triazine advantageously being between 1:32 and 32:11, preferably between 1:16 and 8A.

When a herbicide of the phenylurea family. e.g. isoproturon, is used, it is preferably applied at doses of between 0. 125 and 2 kg/ha, the weight ratio of the compound of formula (1) to the phenylurea advantageously being between 1: 16 and 32: 1, especially between 1: 12 and 8: 1.

When a herbicide of the phenoxybenzoic acid family, e.g. bifenox, is used, it is generally applied at between 0.125 and 4 kg/ha, preferably between 0.25 and 2 kg/ha, the weight of the 10 ratio of the compound of formula (1) to the phenozybenzoic acid, derivative being between 1:32 and 32: 1, more especially between 1: 16 and 8: 1.

When, in this same family, acifluorfen and/or acifluorfen-sodium is used, it is preferably applied at between 0.06 kg and 1 kg/ha, the weight ratio of the compound of formula (1) to the acifluorfen (sodium) most frequently being between 1:8 and 60A, preferably between 1:4 and 15 32A.

When a uracil of the bromacil type is used, the latter is applied at doses of between 0.125 and 10 kg/has, and more especially between 0.125 and 3 kg/ha, the weight ratio of the compound of formula (1) to the uracil advantageously being between 1:80 and 32:11, preferably between 1:24 and 16A.

If a phenoxy acid derivative, e.g. 2,4-1D, is used, it is preferablyapplied at doses of between 0.1 and 5 kg/ha and more especially between 0. 1 and 2 kg/ha. The weight ratio of the compound of formula (1) to the phenoxy acid derivative is then advantageously between 1:40 and 40A, preferably between 1:16 and 20A. The phenoxy acid is advantageously used in the form of one of its alkali metal salts, and more especially in the form of an amine salt or in ester form.

If a carbamate, for example asulam, is used, it is generally applied at doses of between 0.25 and 7 kg/ha, and more especially between 0.25 and 4 kg/ha, the weight ratio of the compound of formula (1) to the carbamate generally being between 1:56 and 16A, and more especially between 1:32 and 8A. The asulam is preferably in the form of an alkali metal salt, especially 30 the sodium salt.

When an aminotriazole is used, it is preferably applied at between 0.5 and 4 kg/ha, the weight ratio of the compound of formula (1) to the aminotriazole generally being between 1:96 and 8A, preferably between 1:32 and 4A.

If propanil is used, it is preferably applied at between 0.25 and 6 kg/ha, the weight ratio of 35 the compound of the formula(l) to propanil advantageously being between 1:48 and 16A, and preferably between 1:48 and 4A.

When quizaolfop-ethyl is used, it is preferably applied at between 0.016 and 1 kg/ha, and more especially between 0.03 and 0.5 kg/ha, the weight ratio of the compound of formula (1) to the quizalofop-ethyl then generally being between 1:8 and 250A, and more advantageously between 1:4 and 60A.

If a nicotinamide, e.g. diflufenican, is used, it is generally applied at doses of between 0.1 and 2 kg/ha, the weight ratio of the compound of formula (1) to diflufenican then generally being between 1:16 and 40A, preferably between 1:6 and 20A.

If an imidazolinone herbicide is used, eg imazapur or imazaquin, the dose is preferably between 45 0.016 and 0.5 kg/ha, and the weight ratio of the compound of formula (1) to the imidazolinone herbicide is most frequently between 1:4 and 250A, more especially between 1:4 and 80A.

Imazapur is advantageously used in the form of its amine salts, especially an isopropylamine salt.

When a benzonitrile type herbicide, e.g. bromoxynil is used, it is preferably applied at from 0.06 kg to 1 kg/ha. The weight ratio of the compound of formula (1) to the benzonitrile derivative is advantageously between 1:8 and 60A, preferably between 1:5 and 32A. The bromoxynil can be in the form of alkali metal salts or advantageously in the form of esters (eg the octanoate). loxynil can be used in place of bromoxynil.

Thiadiazolylureas, e.g. ethidimuron, can also be used. They are preferably applied at between 0.125 and 7 kg/ha and more especially between 0.25 and 2 kg/ha. The weight ratio of the compound of formula (1) to the thiadiazolyiurea is most frequently between 1:56 and 32A, especially between 1:16 and 8A.

Among the products of the oxadiazole chemical family, oxadiazon is preferably used. It is applied at doses of between 0.25 and 4 kg/ha, especially between 0.25 and 2.5 kg/ha. The weight ratio of the compound of formula (1) to the derivative possessing an oxadiazole group is 60 generally between 1:32 and 16A, preferably between 1:20 and 8A.

In the same chemical family, dimefuron can also be used, and this is preferably applied at between 0.25 and 2 kg/ha, the weight ratio of the compound of formula (1) to the oxadiazole then being 1:8 and 16A, in particular between 1:8 and 8A.

When a benzoic acid, e.g. dicamba, is used, it is preferably applied at doses of between 0.05 65 11 GB2169806A 11 and 5 kg/ha, preferably between 0.05 and 0.3 kg/ha, the weight ratio of the compound of formula (1) to the benzoic acid derivative (in particular dicamba) then advantageously being between 1:40 and 80:1, preferably between 1:3 and 20:1.

Quarternary ammonium compounds are also used.

Thus paraquat is preferably applied at between 0.125 and 2 kg/ha. The weight ratio of the 5 compound of formula (1) to paraquat is generally between 1:16 and 32:1, more especially between 1:8 and 16:1.

When the compound of formula (1) is used with a triazine, especially good control of the following weeds is observed: Xanthium pennsylvanicum, lpomea purpurea, Polygonum convolvu- lus, Echinochloa crus-galli, Chenopodiurn, Amaranthus, Sinapis, Capselia and Poa.

When the compound of formula (1) is used with a phenylurea, the activity is especially good on the following weeds: Abutilon theiphrasti, Sesbania exaltata, Xanthiurn pennsylvanicum, Polygonum convolvulus, 1pomea purpurea, Echniochloa crus-gaiii, Alopecurus, Apera, Poa. Atriplex, Sinapis, Chenopodium, Chrysanthemum, Matricaria, Ranonculus and Stellaria.

When the compound of formula (1) is used with phenoxybenzoic acid derivatives, good control 15 of the following weeds is observed: Xanthiurn pennsylvanicurn, 1pomea purpurea, Sesbania exaltata, Abutilon theophrasti, Polygonum convolvulus, Amaranthus, Chenopodium, Sinapis, Da tura, Solanum, Setaria, Euphorbia, Bidens and Galinsoga.

When the compound of formula (1) is used with the phenoxy acid derivative, good control of the following is observed: Portulaca oleracea, Polygonum, convolvulus, Abutilon theophrasti, Xan- 20 thium pennsylvanicum, Chenopodium, Sinapis, Solanum, Ramunculus, Amaranthus, Cirsium and 1pomea.

When the compound of formula (1) is used with a carbarnate such as asulam, Xanthiurn pennsylvanicum, abutilon theophasti and Sesbania exaltata, Sorghum halepense, Pteridium, Aquil inicum, Eleucine, Panicum, digitaria, Setaria, Rumex and Equisetum are especially well controlled. 25 When the compound of formula (1) is used with aminotriazole, good control of Portulaca oleracea, Abutilon theophrasti, Agropyron, Cynodon, Agrostis, Artemisia, Aristolochia, Rumex, Oxalis, Rubus, Equisetum, Lepidium, and Tussilago is noted.

When the compound of formula (1) is used with amides such as propanil, the efficacy is good on 1pomea purpurea, Polygonum convolvulus and Abutilon thophrasti.

When the compound of formula (1) is used with phenoxypropionic derivatives such as quizalo fop-ethyl, good control of lolium multiflorum and Echinochloa crusgalli as well as sesbania exaltata, Alopecurus, Digitaria, Hordeum, Panicurn Miliaceum, Setaria and Sorghum halepense is observed.

When the compound of formula (1) is used with diflufenican, the activity becomes especially 35 good on the following weeds: Portulaca oleracea, Polygonurn convolvulus, Abutilon theophrasti, Sesbania exaltata, Echniochloa crus-galli, Galium, Veronica, Stellaria, Matricaria, Anthemis, Chy ranthemum, Papaver rhoeas, Raphanus and Sinapis.

When the compound of formula (1) is used with an imidazolinone, good control of the following is observed: Xanthiurn pennsulvanicum, 1pomea purpurea, Portulaca oleracea, Sesbania 40 exaltata, Echinochloa crus-galli, Loliurn multiflorum, Amaranthus, Chenopodium, Ambrosia, Hibis cus, Sida, Digitaria, Eleusine, Setaria, Cyperus esculentus, Abutilon theophrasti and Polygonum.

When the compound of formula (1) is used with a benzonitrile derivative, the efficacy is good on 1pomea purpurea, Portulaca oleracea, Polygonum, convolvulus, Amaranthus, Chenopodium, Solanum, Ambrosia, Matricaria, Atriplex, Sinapis and Xanthium.

When the compound of formula (1) is used with a thiadiozolylurea, the efficacy is good on the following weeds: Xanthium pennsulvanicum, 1pomea purpurea, Polygonum convolvulus, Abutilon theophrasti, Sesbania exaltata, Echinochloa crus-galli, Gallium, Sinapis, Stellaria, Chenopodium, Chrystanthemum, Setaria and Poa.

When the compound of formula (1) is used with herbicides of the oxadizole family, especially 50 good control of the following weeds is observed: Xanthiurn pennsylvanicum, Polygonum convol vulus, 1pomea purpurea, Echinochloa crus-galli, Amaranthus, Sinapis, Capsella, Euphorbia, Portu faca, Agropyron, Agrostis, Rubus, Festuca, Dactylis, Galium and Polentilia.

When the compound of formula (1) is used with a quaternary ammonium derivative, the efficacy is good on Xanthium pennsylvanicum, 1pomea purpurea, Polygonum convolvulus, Alope- 55 curus, Setaria, Sinapis, RaphanyS, Chrysanthemum and Amaranthus.

When the compound of formula (1) is used with a benzoic acid such as Dicamba, good control of 1pomea, Xanthium, Chenopodium, Polygonum, Amaranthus, Abutilon, Galium, Matricaria, Stel laria, Mercurialis, Veronica and Rumex is observed. The compositions according to the invention can have a very broad spectrum of activity, the weeds destroyed being annual or perennial, monocotyledonous or dicotyledonous. In Table (111), there are mentioned some of the weeds which it is important to destroy to enable crops such as cereals, maize, rice, cotton, soya, beetroot (in particular sugar beet), sunflower, colza, sugarcane and leguminous crops to become well established or undergo good subsequent development, as well as to obtain satisfactory clearing of weeds from perennical crops (vines, orchards). It is sometimes possible to improve 65 12 GB2169806A 12 the efficacy of weed clearing by carrying out sequential treatments, optionally involving a soil treatment.

The example which follows illustrates the invention and shows how it can be employed.

Example 55: Post-sprouting herbicidal activity on plant species in the greenhouse.

In pots 9X9X9 cm filled with light agricultural soil, a number of seeds are sown which is determined according to the plant species and the size of the seed.

The seeds are then covered with a layer of soil approximately 3 mm thick.

After the soil is moistened, the plants are allowed to sprout and grow to a height of approximately 5 to 10 cm. The stage of treatment for grasses is the "second leaf forming" 10 stage. The stage of treatment for dicotyledons is the "cotyledons spread, first true leaf developing" stage.

The pots are then treated by spraying an amount of mixture per pot corresponding to a volume of 500 1/ha and containing the active substance at the dose in question.

For each active substance, the mixture was prepared by diluting with a specified amount of 15 water, so as to obtain the desired concentration, on the one hand a formulation of the dispersible pellet type containing 20% of active substance of the compound No. 1, and on the other hand one of the formulations of active substances of the group B).

Depending on the concentration of active substance in the mixture, the dose of active sub- stance applied varies according to the products, from 16 to 1000 g/ha.

The treated pots are then placed in troughs designed to receive irrigation water, subirrigation being employed, and maintained for 35 hours at room temperature and at 70% relative humidity.

After 35 days, a count is made of the number of living plants in the pots treated with the mixture containing the active substance to be tested and the number of living plants in a control pot treated according to the same conditions but with a mixture not containing any active substance. The percentage destruction of treated plants is thereby determined relative to the untreated control. A percentage destruction equal to 100% indicates that there has been com plete destruction of the plant species in question, and a percentage of 0% indicates that the number of living plants in the treated pot is identical to that in the control pot.

The plant species on which the tests were performed are indicated in Table (111) by the 30 abbreviation adjacent to the latin name.

The results obtained according to this Example 55 are shown in Table (V). The doses of active substances employed in this example are generally relatively, low, so that the results obtained, even when modest, are frequently evidence of strong potential activity. The use of higher doses (in particular double doses) than those shown naturally leads to still better results. 35 In many cases, the combinations according to the invention show a synergistic effect with respect to the active substances taken in isolation.

13 GB2169806A 13 TABLE (III)

1 1 1 American name Latin name pigweed &maranthus retroflexus velvet leal" labutilon fFe-j5FFast7AB7i I prickly sioa I sica spinosa sest)ania 1 cocklebur I xantnium pennsylvan4icxr I (XAf) oiaens 1 1 1 i 1 1 convolvulus arvens-is 1 20 1 1 1 1 1 1 1 1 25 i corn marigola 1 cnrysantmemum segetim 1 1 thi.Ckweec 1 stellaria med-Ja 1 crabgrass i dici taria san;uinail-s-1 1 giant foxtail 1 setaria faDe.-.&.i 1 IclaCK nigntsnaciei cyperus esculentus solanum nigrum barnyard grass ecIiinocnloa crus-;a-li 1 (ECH) wila oat i Pena fatua ye grass 1 lolium mulkiflorum 1 black grass 1 alopecurus myosjrz-=es 1 1 quack grass bermuda grass agr3Pyron repens 1 1 1 i 1 1 1 sz.na:)is a:ven.s-s morning glory 1 1 - 1 cynocon cac:'ty!3-, 1 1 - Mustarc:

1 willi 1 1 1 14 GB2169806A 14 1 t)indweed 1 1 calystegia sepium 1 1 1 1 I blaCkberry 1 rubus fructicosus 1 1 1 1 purslane 1 portulaca oleracea-7P5-"0R-il 1 Qild bUCkQheat polygonum Convolvulus 1 1 (P3LM 1 hemp sescania sesbania exaltata CSES) 1 1 Common names TABLE (IV) Chemical name (standard IUPAC nomenclature Atrazine 2-chloro-4-ethylamino-6-isopropyi- amino- 1,3,5-triazine lsoproturon 3-(4-isopropylphenyi)- 1, 1 -dimethyl urea Bifenox methyl 5-(2',4-dichlorophenoxy)-2- 25 nitrobenzoate Bromacil 5-bromo-3-sec-butyi-6-methyluraciI 2,4-D ammonium (2,4-dichlorphenoxy)acetate Asularn methyl 4-aminobenzenesulphonyl carbamate (sodium salt) 30 Arninotriazole 3-amino- 1 H- 1,2,4-triazole Propanil N-(3,4-dichlorophenyi)propionamide Quizalofop-ethyl ethyl 2-[4-(5-chloro-2-quinoaxiinyloxy) phenyloxylpropionate Diflufenican N-(2,4-difluorophenyi)-2-(3-tri- 35 fluoromethylphenoxy)nicotinamide Impazapur isopropylammonium 2-[4,5-dihydro-4 methyi-4-(isopropyi)-5-oxo- 1 H imidazol-2-yil-3-pyridinecarboxylate Acifluorfen-sodium sodium 5-[2'-chloro-4'-(trifluoro- 40 methyi)phenoxy]-2-nitrobenzoate Bromoxynil 3,5-dibromo-4-hydroxybenzonitrile octanoate Ethidimuron 1-(5-ethisulphony]- 1,3,5 thiadiazol- 45 2-yl)- 1,3,-dimethylurea Oxidiazon 5-tert-butyi-3-(2',4' dichloro-5'-isopropyloxyphenyl)1,3,4-oxadiazolin-2-one Paraquat 1, 1'-dimethyi-4,4'-bipyridinium 50 chloride Dimefuron 3-[2-chloro-4 (3,3-dimethylureido)-phenyi]-5 (1, 1 -dimethylethyi)-3H- 1,3,4 oxadiazol-2-one 55 Dicamba dimethylammonium 3,6-dichloro-2 methoxybenzoate GB2169806A 15 TABLE (V)

Compound Cjoqomd 1 of the gTvf (B) No. 1 1 XAN 1 IPO 1 POR 1 POL 1 1 nature dose in a/ha 1 1 1 1 1 1. 1 250 1 250 1 90 1 98 1 loo T-90 i 1 1 1 1 1 1 1 latrazine 1 500 1 125 1 so iloo1 130 -1 1-00 1 . 1 1 1 1 1 1 1 1 500 1 250 1 100 1100 1 100 1 100 1 250 250 10c) 98 1 100 1 30 1 500 1 125 1 90 1 50 1 100 1 20 500 1 250 1 90 1 98 1 100 60 1 500 1 250 1 90 1 90 j 100 1 100 1 1 1 bifenox 1000 1 125 1 50 1 90 1 100 1 98 1000 1 230 1 70 j 90 1 100 1 1OU1 1 1 125 1 250 1 go 1 50 1 100 1 98 i 1 1 1 1 1 1 1 1 1 bromacill 230 1 125 1 100 1 98 1 100 1 100 i 1 1 1 1 1 1 1 250 1 230 1 loo j100 l loo F=1 1 1 1 1 1 1 1 125 1 250 1 100 1100 1 100 1 80 1 1 1 1 1 1 1 1 1 1 2,4-D 1 230 1 125 1 100 1100 1 100 4 60 1 1 1 1 1 1 11 1 1 250 1 250 1 100 1100 1100 1 98 1 1 1 1 1 1 1 1 1 1 1 1 1 1 1 isopro20 1 turon 1 1 1 1 35 1 1 1 asulam 500 250 1 100 1 20 1 10 2-0 1 amino- 1 1000 1 250 1 20 0 80 2 1 triazolel 1 1 1 250 90 1 95 30 1 propanill 1000 i 125 1100 1 loc) 1 loo 1 157 ' - i 1 1 1 1 1 -1 1 1 1 1 1000 1 250 1 100 1100 1 90 1 loo 1 quizalo-1 31 1 250 2 3 0 1 50 1 2 Z 1 Ifop-ethyll 1 1 1 1 carDeta-1 4000 1 250 1 20 1 90 1 3C 1!C 1 1 mide. 1 - 1 1 1 1 1 1 1 1 16 GB2169806A 16 diflufe-l 1000 250 nican 1 1 50 1 40 1 100 1 98 1 1 1 1 1 1 1 1 31 1 250 J-100 1 90 1 98 1 90 1 1 1 1 1 1 1 1 1 1 imazapurl 62 1 125 1 100 1 80 1 100 1 100 1 1 1 1 1 1 1 1 1 62 150 100 90 loo-T-ro-ol 1 62 1 250 1 80 lloo 1 loo 1 loo 1 1 1 1 1 1 1 - 1 lacifluor-1 125 1 125 1 100 1100 1100 j 100 1 Ifen 1 1 1 1 1 1 1 lsodium T 1-25 1 250 1 loo lloo 1 loo-l loo 1 1 1 1 1 1 1 1 1 1 62 1 250 1 100 J'80 1 30 1 80 1 1 1 1 1 1 1 1 1 125 1 125 1 100 1100 1 0 1 90 1 1 1 1 1 1 1 1 250 90 1100 1 90Moo 1 1 125 1 250 1 100 1100 1 100 1 100 1 1 1 1 1 1 1 1 1 250 1 125 1 100 1100 1 100 1 100 1 1 1 1 1 1 1 1 1 250 1 250 1 100 1100 1 100 1 100 1 1 1 1 1 1 1 1 1 250 1 250 1 100 1100 1 100 1 100 1 1 1 1 1 1 1 1 1 500 1 125 j 30 j 40 1 100 1 100 1 1 1 1 1 1. 1 1 1 500 1 250 1 loo lloo1 loo F-1-07-1 1 1 1 1 1 1 1 1 125 1 250 1 100 1 100 1 98 1 98 1 1 1 1 1 1 1 1 1 250 1 125 1 98 1 50 1 100 j 90 1 1 1 1 1 1 '1 1 1 250 1 250 1 100 1 90 1 98 1 90 1 dimefuro 1.116000 1 250 1 30 1 10 1 100 1 90 1 1 1 1 bromo xynil ethidimuron 1 1 oxadia1 zon 1 1 1 1 I I I paraI quat 17 GB2169806A 17 TABLE (V)

Compound 1 Compoundl 1 1 1 of the group (B) 1 No. 1 ASU SES ECH mature dose in Olha 2 5 0 1 250 i 60 1 100 60 latrazine 1 500 125 j - 1 500 1 250 1 - 1 1 1 250 250 1 0 1100 60 7 1 isopro- 1 50G 1 1,25 1 100 1100 1 50 1 turon 1 1 1 1 1 1 500 1 250 100 1130 1 ILU 1 500 1 250 90 ilOO 1 20 cifenox lOjO 1 1 iz)j 1 20 T-71 j 1 25S 1 IJU 1 98 f 2 J 25; 1 8j, 1 bromacill 2501 125 294-D 1 1 I1 1 1 1 1 90 1 100 1 98 F 1 1 1 1 1 250 1 250 1 100 110c) 1 JOG F 1 1 1 1 1 1 250 80 J100 20 T-2 5 0 1 17- 5 1 5c) 1 10c) 1 ICj 1 1 1 1 1 1 1 250 250 100 1100 50 asullam 50L) 7-50 90 1130 1 20 amino- 1 1000 250 100 i 100 60 -T triazolel 1 1 1 500 i 255 1 60!Ioj ic Propanill 1000 1 125 j 60 100 20 1000 1 250 95 1130 70 quiza.Lo-1 31 1 70 80 j100 lfop-ethyll 1 1 1-ca-r:)eta- 1 4Di:),,) 1 250 1 80 1 10i 1 Mide 1 1 1 1 1 1 1 1 1 1 1 1 1 1 18 GB2169806A 18 1 31 1 250 1 1 7 1 imazapuri 62 1 125 1 100 1 95 1 90 j 1 1 1 1 1 1 1 62 1 250 1 100 1 95 j 100 F 1 1 1 1 1 1 62 1.250 1 so 1130 1 20 1 lacifluor-1 125 1 125 60 1100 1 20 j Ifen 1 1 1 1 1 Isodium 1 125 1 250 80 1100 30 62 250 20 90 1 30 7 bromo- 1 125 1 125 50 95 10 xynil 1 1 1 125 1 250 1 60 80 30 r 1 125 1 250 j 100 1 98 1 jo 7 1 1 1 1 1 1 ethidi- 250 1 125 100 95 1 10 muron diflufe-1 1000 1 250 nican 1 1 1 1 1 1 1 1 1 1 1 1 153 1 250 1 100 J100 1 60 1 250 1 250 1 100 1100 1 90 1 1 1 1 1 1 1 1 500 1 125 1 100 li00 1 98 1 1 ' 1 1 1 1 1 1 500 j 250 1 100 1100 1 100 7 1 1 1 1 1 1 1 125 1 250 1 100 1 100 1 100 7 1 1 100 100 1 95 r 1 230 1 250 1 100 1 100 1 100 F 1 1 1 1 1 1 1 dime-f-u----f- 1-000 1 250 1100 1 100 F-550 7 1 ron 1 1 1 1 1 1 1 1 oxadia1 zon 1 1 1 1 1 para1 quat 1 1 1 1 1 1 19 GB 2 169 806A 19

Claims

1. A herbicidal composition comprising A) an active herbidical substance of formula:

OR 2 1 1 0 = P - CH 2 - NH - CH 2 - CO - N - SO 2 - R (I 1 3 1 OR R in which:

R' denotes an optionally substituted hydrocarbon radical; R denotes a hydrogen atom or is as defined for W; R2 and R3, which may be identical or different, denote hydrogen atoms or are such that OR2 15 and OR3 are hydrolysable groups, or a salt thereof; and B) at least one active herbicidal substance which is a chloroacetamide, triazine, phenylurea, thiadiazolylurea, sulphonylurea, benzothiazolylurea, nitroaniline, phenoxynicotinanilide, amide, oxa diazole, aminotriazole, picolinic acid, phenoxybenzoic acid derivative, phenoxypropionic acid deri- 20 vative, aryloxy acid, benzoic acid, propionic acid, triazinone, carbamate, pyridazinone, pyridine, quaternary ammonium compound, uracil, hydroxybenzonitrile or imidazolinone or a salt thereof.

2. A composition according to claim 1 wherein R' is a hydrocarbon radical optionally substi tuted by halogen, phenyl, cyano, alkyl, alkoxy, or alkyl carboxylate.

3. A composition according to claim 1 or 2 wherein the hydrocarbon radical represented by 25 R' is an alky], aryl or cycloalkyl radical.

4. A composition according to claim 1, 2 or 3 wherein the hydrocarbon radical contains from 1 to 7 carbon atoms or, when the hydrocarbon radical is a cycloalkyl group, from 3 to 7 carbon atoms.

5. A composition according to any one of the preceding claims wherein R' represents an 30 optionally halogenated alkyl radical containing from 1 to 4 carbon atoms.

6. A composition according to any one of the preceding claims wherein R represents an alkyl group containing from 1 to 4 carbon atoms.

7. A composition according to any one of the preceding claims wherein R2 and R3 each represent an alkyl or aryl radical optionally substituted by halogen, phenyl, cyano, alkyl, alkoxy or 35 alkyl carboxylate.

8. A composition according to claim 7 wherein R2 and R3 each contain from 1 to 12 carbon atoms.

9. A composition according to claim 7 wherein R2 and R3 each contain from 1 to 8 carbon atoms.

10. A composition according to any one of the preceding claims wherein R and W, which may be the same or different, each represent an alkyl radical having 1 to 4 carbon atoms and R 2 and R3, which may be the same or different, each represent a hydrogen atom or an alkyl radical having 1 to 4 carbon atoms or a phenyl radical.

11. A composition according to any one of claims 1 to 6 in which R and W, which may be 45 identical or different, are alkyl radicals having 1 to 4 carbon atoms and R2 is a hydrogen atom.

12. A composition according to any one of claims 1 to 6 in which R and W, which may be identical or different, are alkyl radicals having 1 to 4 carbon atoms and R2 and R3 are hydrogen atoms.

13. A composition according to any one of claims 1 to 12, in which the substance B) is 50 alachlor, metolachlor, simazine, atrazine, prometryne, diuron, isoproturon, linuron, tebuthiuron, ethidimuron, sulforneturon, chlorsulfuron, metsulfuron, methabenzthiazuron, oryzalin, trifluralin, difl ufenican, napropamide, propanil, oxadiazon, dimefuron, aminotriazole, picloram, bifenox, acifluor fen, acifluorfen-sodium, fomesafen, oxyfluorfen, esters of acifluorfen and aliphatic alcohol, glyco late or lactate, quizalofop-ethyl, fluazifop-butyl, 2,4,-D, 2,4-1)P, MCPA, MCPP, dicamba, dalapon, metribuzin, carbetamide, EPTC, asulam, norflurazon, fluridone, diquat, parquat, bromacil, bromo zynil, ioxynil, imazaquin or imazapur.

14. A composition according to any one of claims 1 to 13, in which the proportion of compound of formula (1) to the substance B) is from 0.2A to 10:1 by weight.

15. A composition according to claim 14 in which the proportion of compound of formula (1) 60 to the substance B) is from 0.25:1 to 4:1 by weight.

16. A herbicidal composition according to any one of claims 1 to 15 additionally comprising at least one inert carrier which is agriculturally acceptable.

17. A composition according to claim 16, which contains 0.05 to 95% of active substances relative to the total weight of the composition.

GB2169806A 20

18. A composition according to claim 16 or 17, which contains 5 to 40% of surfactant relative to the total weight of the composition.

19. A composition according to any one of claims 1 to 18, which is in the form of a soluble powder, wettable powder or dry flowable.

20. A herbicidal composition substantially as hereinbefore defined with reference to any one 5 of Example 1 to 53.

21. A two component pack comprising a first component which comprises a herbicidally active substance of formula (1) as defined in claim 1 and a second component which comprises at least one herbicidally active substance defined in group 13) in claim 1 which can be applied simultaneously or separately.

22. A two component pack according to claim 21 substantially as hereinbefore described.

23. A method of combating weeds at a focus which comprises applying thereto an effective amount of a composition according to any one of claims 1 to 22.

24. A method according to claim 23, wherein the active hericidal substances are applied in a total amount from 0. 1 to 10 kg/ha.

25. A method according to claim 24 wherein the active substances are applied in a total amount of from 0.5 to 8 kg/ha.

26. A method of combating weeds at a locus wherein an active herbidical substance of formula (1) as defined in claim 1 and an active herbicidal substance defined in group 13) of claim 1 are applied sequentially to weeds, the substance of group 13) being applied to the soil adjacent 20 to the weed.

27. A method according to claim 23 or 26 substantially as hereinbefore described.

Printed in the United Kingdom for Her Majesty's Stationery Office, Dd 8818935, 1986, 4235. Published at The Patent Office, 25 Southampton Buildings, London, WC2A 'I AY, from which copies may be obtained.

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