NZ214880A

NZ214880A - Herbicidal composition containing an n-(phosphonomethylglycyl)sulphonylamine and another known herbicide

Info

Publication number: NZ214880A
Application number: NZ214880A
Authority: NZ
Inventors: Albert Bertrand; Guy Borrod
Original assignee: Rhone Poulenc Agrochimie
Priority date: 1985-01-23
Filing date: 1986-01-21
Publication date: 1990-12-21
Also published as: OA08194A; EP0192583B1; ATE43222T1; GB2169806A; GB8601468D0; FI82877C; AU577658B2; JPS61172805A; BR8600228A; CN86100691A; DD251701A5; PH21453A; KR920007584B1; KR860005586A; GB2169806B; AU5259586A; MA20611A1; EP0192583A1; FR2576181B1; DE3663436D1

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

<div class="application article clearfix" id="description"> New Zealand Paient Spedficaiion for Paient Number £14880 NO DRAWINGS Priority Date(s): ...3.". .1. Complete Specification Filed: 2.\: .I'&fcv Class: .. Publication Date: P.O. Journal, No: . vagf?. 2f 48 80 NEW ZEALAND FII 405- fv Ia21 JAN I986 £! V /i A' THE PATENTS ACT 1953 \^c e , s, tV 1 PATENTS FORM NO. 5 COMPLETE SPECIFICATION II HERBICIDAL MIXTURES BASED ON A COMPOUND OF THE N-(PHOSPHONOMETHYLGLYCYL)SULPHONYLAMINE TYPE" WE, RHONE-POULENC AGROCHIMIE, a French Body Corporate, of 14-20 Rue Pierre Baizet, Lyon 9e, France, hereby declare the invention for which we pray that a patent may be granted to us and the method by which it is to be performed, to be particularly described in and by the following statement: i V y.v ■ • !- | >m' 2 148 80 "* - la- HERBICIDAL MIXTURES BASED ON A COMPOUND OF THE N-(PHOSPHONOMETHYLGLYCYL)SULPHONYLAMINE TYPE ^ The present invention relates to new herbicidal compositions containing herbicidal mixtures of one herbicide of the N-(phosphonomethylglycyl)sulphonylamine chemical family, as well as to the application of these 5 herbicidal compositions in agriculture. Many compounds are known which possess an aminomethylphosphonic group and have herbicidal properties, in particular in French Patents 2,129,327, 2,281,375, 2,251,569, 2,413,398 and 2,463,149, European 10 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. 15 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 aminomethylphosphonic group are known, but these products are either of low activity or inactive. 20 It 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 herbicidal compositions possessing a G j . 2' 488-6 7 * I - 2 - 5 broad spectrum of activity, which have at least f partially a descending systemic effect and are possibly i 5 selective for certain crops. f A further object of the invention is to provide 5 herbicidal compositions which have persistence in the ^ soil, in particular sufficient persistence to act ! O against staggered sproutings (i.e. against weeds and other plants, the growth and development of which are spread out over a period of time). 10 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 15 (A) an active substance of formula: OR2 I ! 0 = P - CH- - NH - CH0 - CO - N - SO- - R (I) I 3 2 2 I 2 OR-3 R in which: R^" denotes an optionally substituted hydrocarbon CJ radical, in particular an alkyl, aryl or cycloalkyl 20 radical, each of which may be substituted; suitable substituents include halogen atoms and phenyl, cyano, alkyl, 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 1 i 2 J 488 - 3 - atoms, preferably from 1 to 7 carbon atoms and more especially from 3 to 7 carbon atoms when it is a cycloalkyl group; it is most preferably an alkyl radical having from 1 to 4 carbon atoms, which may optionally be 5 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 R^, which may be identical or different, denote a 2 3 hydrogen atom or are such that OR and OR are 2 3 hydrolysable groups; R and R can be, in particular, alkyl or aryl radicals, preferably alkyl or phenyl radicals, which are optionally substituted; suitable 15 substituents are those specified in the definition of 12 3 R ; R and R 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, 20 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 O gfwKwp w . ft *.° ""-rfr'' n i • 21 4SS-0 - 4 - equal to 2.5; and B) at least one active substance which is a chloroacetamide (in particular alachlor or i metolachlor), triazine (in particular simazine, ! 5 atrazine or prometryne), phenylurea (in particular diuron, isoproturon or linuron), thiadiazolylurea ■ I (in particular tebuthiuron or ethidimuron) , sulphonylurea (in particular sulfometuron, chlorsulfuron or metsulfuron), benzothiazolylurea 10 (in particular methabenzthiazuron) , nitroaniline (in particular oryzalin or trifluralin), phenoxynicotinanilide (in particular diflufenican), amide (in particular napropamide or propanil), oxadiazole (in particular oxadiazon or dimefuron) , 15 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), 29 phenoxypropionic derivative (in particular f"\ quizalofop-ethyl or fluazifop-butyl), aryloxyacid (in particular 2,4-D, 2,4-DP, MCPA or MCPP), benzoic acid (in particular dicamba), propionic acid (in particular dalapon), triazinone (in 25 particular metribuzin), carbamate (in particular carbetamide, 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 (I), the preferred compounds are those in which R and R* are each 2 an alkyl group having from 1 to 4 carbon atoms, and R and R"* are each a hydrogen atom or an alkyl group having 1 to 4 carbon atoms or a phenyl group, as well as the 2 salts of these compounds: R preferably represents hydrogen. Among the compounds of the group B), the preferred compounds are, if good persistance is sought: simazine, atrazine, prometryne, diuron, chlorsulfuron, oryzalin, napropamide, oxadiazon, dimefuron, picloram, fomesafen, bromacil and imazaquin. for example, according to the procedure described in New Zealand patent specification 209010. compounds most of them being described in detail in works such as "The Pesticide Manual" published by "The British Crop Protection Council", the 7th edition of which dates from 1983 . The chemical names of rrost of the oroducts of the group 3) used in Tabl.e-^ftTi * y r* '• > * are given in Table (IV) . //'V The compounds of formula (I) can be prepared, The compounds of the group B) include known : ■ i to," T-">s|,n' '-"Jr. * r> n r--. C 21488© - 6 - The compositions according to the invention are generally of the binary type (a single compound of formula (I) and a single active substance of the group B)} but ternary combinations (eg two active substances 5 of the group B)), quaternary combinations (eg three active substances of the group B)) or others can be used. The ratio by weight of active substance of formula (I) relative to the active substance of the 10 group B) is generally from 0.2:1 to 10:1, and is preferably from 0.25:1 to 4:1; this ratio can, however, be higher, e.g. 100:1, when active substances such as picloram and, in particular, sulphonylureas are used. The Examples in this specification are given to 15 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 20 post-emergence. In practice the compositions according to the invention usually contain a solid or liquid carrier which is agriculturally acceptable and/or a surfactant which is also agriculturally acceptable. In particular, 25 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 sub.stances possessing pesticidal (in particular insecticidal, fungicidal or herbicidal) 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. compositions of the present invention can vary within wide limits according to the nature of the weeds to be eliminated and the degree of infestation of the loci which have to be cleared of weeds. invention usually contain 0.05 to 95% of active substance [formula (I) 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 surfactants. 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 carrier is hence generally inert and it must be agriculturally acceptable, in particular The proportions of active substances used in the In general, the compositions according to the In the present disclosure, the term "carrier" on the treated plant. y.ii*. f... ■: V- '. S-itWV > -.:, : ., „,v,......;.™V.'^ r .-, : . . l J ' '6 Zl4-g%o % | - 8 - •t' | As solid carriers (or fillers), inorganic or 1 j synthetic fillers may be mentioned, e.g. kaolin, t attapulgite, montmorillonite, bentonite, talc, fuller's earth, diatomaceous earth, kieselguhr, calcium and 5 magnesium carbonates, precipitated synthetic silica, alumina, alkali metal silicates and silicoaluminates, | fy\ resins, waxes and solid fertilizers. Water-soluble J "W1' I \ fillers, e.g. sodium sulphate or ammonium sulphate and urea, can also be used. 10 As liquid carriers, there may be mentioned i water, alcohols (in particular butanol), esters (in \ \ particular methylglycol acetate), ketones (in particular r j j cyclohexanone and isophorone), petroleum fractions, aromatic hydrocarbons (in particular xylenes) or 15 paraffin hydrocarbons, chlorinated aliphatic hydrocarbons (in particular trichloroethane) or chlorinated aromatic hydrocarbons (in particular chlorobenzenes), and water-soluble solvents such as dimethylformamide, dimethyl sulphoxide and ■ 20 N-methylpyrrolidone. 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 25 mentioned ethylene oxide-treated alkylphenols (in particular octyl-, nonyl- and tributylphenols having 6 to 18 oxyethylene units), ethylene oxide-treated fatty o r* * 2 1 483(0 - 9 - alcohols (in particular C^q to C^g alcohols having 6 to 18 oxyethylene units), ethylene oxide-treated fatty amines (in particular tallow amine or tall oil having from 2 to 40 oxyethylene units), and esters of fatty 5 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 10 alkylnaphthalenesulphonate ester salts (in particular sodium or potassium isopropyl-, butyl- and dibutylnaphthalenesulphonates), sulphate ester salts of fatty alcohols (in particular sodium or potassium lauryl sulphate), sulphosuccinate ester salts of fatty alcohols 15 (in particular sodium or potassium dioctyl sulphosuccinate), and taurine derivatives (in particular \ alkyltaurates, aryl-N-methyltaurides and sodium oleylmethyltauride). As nonionic dispersants, there may be mentioned 20 ethylene oxide-treated arylphenols (in particular bis- (~^) and tr is (phenylethyl) phenols containing 18 to 40 oxyethylene units]. As anionic dispersants, there may be mentioned salified polycarboxylic polymers (such as sodium 25 polycarboxylate and polyacrylate polymers), polycondensates of formaldehyde and diphenolsulphonates / or alkylnaphthalenesulphonates (in particular sodium methylnaphthalenesulphonate), phosphoric acid ester salts or acid esters of ethylene oxide-treat#»d 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 to fatty alcohols having 6 to 18 oxyethylene units), and alkali metal or alkaline earth metal 1ignosulphonates. 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 compostion. As a natural binder, there may be mentioned starch and its derivatives (in particular modified starch and dextrin), cellulose derivatives (in particular carboxymethylcellulose, hydroxyethylcellulose and hydroxypropylmethylcellulose), 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 <W I 1 2 1 4-'&'$sQ - 11 - such as polyglycols; copolycondensates of maleic anhydride; polycondensates of formaldehyde and alkylnaphthalenesulphonates (e.g. the polycondensate of formaldehyde and sodium methylnaphthalenesulphonate) and 5 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 10 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, 15 marketing and storage, are, on the whole, concentrated i I '] compositions. J ^ (O} 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 20 100%) and pellets (preferably 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 (I) and group B) in these 25 pellets preferably being between 0.5 and 80% for these latter cases. As liquid forms of compositions, or forms •unu-A'Ui'- <rl'v**- '■ v. fa 2 1 488 - 12 - intended to make liquid compositions at the time of use, there may be mentioned solutions and flowables, or alternatively pastes. Concentrated compositions in the solid state are preferred. 5 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 10 agents, from 0 to 10% of suitable additives, e.g. antifoams, corrosion inhibitors, stabilizers, penetrants and adhesives, and, as a carrier, water or an organic liquid in which the active substances are of low solubility or insoluble: certain organic solid 15 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 1): 20 - active substances 500 g - polycondensate of ethylene oxide with tristyrylphenol phosphate 50 g - polycondensate of ethylene oxide with alkylphenol 50 g 25 - sodium polycarboxylate 20 g - ethylene glycol (antifreeze) 50 g - organopolysiloxane oil (antifoam) 1 g © i r\ 2 1 4< - 13 - - polysaccharide (thickener) 1.5 g - water 316.5 g According to this Example 1, compositions can be produced with, in particular, the following products: 5 Products of formula (I): Compound No. 1: compound of formula (I) in which 1 2 3 R and R are both methyl groups and R and R are both hydrogen atoms; Compound No. 2: compound of formula (I) in which 1 2 10 R and R are both methyl groups, R is a hydrogen atom and R^ is a phenyl group; Compound No. 3: compound of formula (I) in which 1 2 3 R and R are both methyl groups and R and R are both phenyl groups. 15 Products of group (B): simazine, atrazine, prometryne, diuron, isoproturon, linuron, metabenzthiazuron, oryzalin, trifluralin, diflufenican, napropamide, propanil, oxadiazon, aminotriazole, picloram, bifenox, acifluorfen-sodium, quizalofop-ethyl, 2,4-D, MCPA, MCPP, 20 carbetamide, asulam, bromoxynil, ioxynil. According to Example 1, Examples 2 to 10 are produced as defined in the following Table (I): W.-SvtWf • © O 10 15 20 25 ■2 1 488o - 14 - 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 (No. 1) 300 Atrazine 200 3 (No. 2) 250 Oryzalin 250 4 (No. 1) 450 Diflufenican 50 5 (No. 2) 350 Ox ad iazon 150 6 (No. 2) 250 Aminotr iazole 250 7 (No. 3) 300 Bifenox 200 8 (No. 1) 350 Acifluorfen Na 150 9 (No. 3) 250 Asulam 250 10 (No. 1) 350 Bromoxynil 150 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: Example 11: - active substances 50% - calcium lignosulphonate (deflocculant) 5% €> o C ST***.; ^J 48B© - 15 - - isopropylnaphthalenesulphonate (anionic wetting agent) 1% - anti-caking silica 5% - kaolin (filler) 39% 5 Example 12: - active substances 80% - sodium alkylnaphthalenesulphonate 2% - sodium lignosulphonate 2% i - anti-caking silica 3% _ kaolin 13% I Example 13: i | - active substances 50% | - sodium alkylnaphthalenesulphonate 2% J 1 - methylcellulose of low viscosity 2% I I 15 - diatomaceous earth 46% i J . j ] Example 14: - active substances 90% - sodium dioctyl sulphosuccinate 0.2% - synthetic Silica 9.8% 20 Example 15: ' - active substances 400 g - sodium lignosulphonate 50 g - sodium dibutylnaphthalenesulphonate 10 g - silica 540 g 25 Example 16: - active substances 250 g - isooctylphenoxy(polyoxyethylene)ethanol 25 g a © /-> V / _ 16 _ - mixture of equal parts by weight of whiting and hydroxyethyLceLluLose 17 g - sodium a I urninosiIicate 543 g - k ieselguhr 165 g 5 Example 17; - active substances 100 g - mixture of sodium salts of saturated fatty ac id sulphates 30 g - condensation product of naphthalene- 10 sulphonic acid and formaldehyde 50 g - kaolin 820 g Example 18: - active substances 402 - sodium isopropylnaphthalenesulphonate 22 15 - sodium lignosulphonate 52 - precipitated silica 102 - kaolin q.s. 1002 Example 19; - active substances 402 20 - sodium lauryl sulphate 42 - tris(phenylethyl)phenol containing 40 oxy-ethyleneunits 62 -precipitatedsilica 152 - attapulgite q.s. 1002 25 Example 20: - active substances 402 - tallow amine containing 25 oxyethylene units 102 © /-"-N - 17 - - Ci3 alcohol containing 6 oxyethylene units 52 /"-•v -precipitatedsilica 15 X - attapulgite q.s. 1002 Example 21: 5 - active substances 502 - sodium oleylmethyltauride 22 - sodium methylnaphthalenesulphonate poly-condensed with formaldehyde 42 - diatomaceous earth 202 10 - kieselguhr q.s. 1002 Example 22: - active substances 502 - nonylphenol containing 18 oxyethylene units 22 - nonylphenol phosphate containing 10 o x y -15 ethylene units 42 -precipitatedsilica 102 - montmori11 onite q.s. 1002 Example 23: - active substances 602 20 - sodium dioctyl sulphosuccinate 7$ - polycondensed sodium methylnaphlenesulphonate 32 - sodium siIicoaluminate 152 -kaolin q.s. 1002 Example 24: 25 - active substances 602 - sorbitan stearate (stearate of dehydrated sorbitol) containing 25 oxyethylene units 52 214SS0 - 18 - - phosphated tris(phenylethyl)phenol containing 18 oxyethylene units 32 -precipitatedsilica 102 - kieselguhr q.s. 1002 Example 25: - active substances 602 - sodium oleylmethyltauride 22 - phosphated tris(phenyIethyI)phenoI containing 18 oxyethylene units 3% - silica 15% - kaolin q.s. 100% Example 26: -active substances 70 2 - sodium isopropylnaphthaLenesuLphonate 22 - condensed sodium roethyLnaphthaLenesuLphonate 32 -synthetics ilica 152 -kaolin q.s. 1002 • . .Example 27: -activesubstances 802 - sodium Lauryl sulphate 32 -sodiumpolycarboxylate 32. - sodium silicoaluminate q.s. 1002 In these Examples 11 to 27, one of the compounds used a sail active substance is compound No. 1,2 or 3 and the other is simazine, atrarine, prometryne, diuron, isoproturon, linuron, metabenth iazuron, t r i f L u r a I i n , M'K fi u f e rvfc an , y'V -0\y napropamide, oxadiazon, dimefuron, bif&ir'ox, qu i j a l"t\t o o-ethyl, 214880 o, O O 15 - 19 - da lapon, carbetamideor another active substance mentioned in Table (IV). Examples 28' to 39 are defined in Table (II). The mix- tures given in Table (V) can also be used. TABLE (II) 10 20 Example' Composition derived from Examples 11 to 17 Amount in grams (or percentage) of one of the compounds 1 to 3 Nature and amount in grams (or percentage) of compound of the grouD .B) 28 11 (No. 1) 30% Atrazine 20% 29 12 (No. 2) 50% Diuron 30% 30 13 (No. 3) 30% Simazine 20% 31 14 (No. 3) 60% Dimefuron 30% 32 11 (No. 2) 25% Isooroturon 25% 33 16 (No. 3) 150 g Bifenox 100 g 34 15 (No. 1) 200 g Naprooamide 200 g 35/ 12 (No. 1) 55% Oxadiazon 25% 3* 17 (No. 2) 85 g Quizalofoo- 15 g ethyl 37 13 (No. 2) 20% Carbetamide 30% 38 15 (No. 3) 300 g Diflufenican 100 g 39 14 (No. 1) 30% Dalaoon 60% • To obtain powders for spraying or wettaoie powders, the active substances are intimately mixed in suit-25 able blenders with the additional substances, or the porous filler is impregnated with the molten JUL 1989 */) v?-'^,,,.7_v„,,^iV. ,u.-r.^4^.^,^. ,,,.,,,4,,.-,, 214880 | -20- | substances and ground with suitable mills or other grinders ! \ i Powders for spraying which have advantageous- wettability and suspendibiIity are thereby obtained; they can be suspended in water at any desired concentration and this sus-5 pension can be very advantageously used, especially for ; C'^ application on plant leaves. I The "dry flowables" (more precisely, these are 'Z | pellets which can be easily dispersed in water) are sub- I | stantially similar in their composition to the wettable 10 powders. They can be prepared by granulation of formula-I tions described for the wettable powders, either by a wet i method [bringing the finely divided active substances into contact with the inert filler and with a little water, e.g. i 1 to 202, or a little of an aqueous solution of dispersant 15 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: 20 Example 4C.: o - active substances 800 g _ - sodium alkylnaphthalenesulphonate 20 g - sodium methylenebis(naphthalene)sulphonate 80 g -kaolin 100 g 25 Example 41: - active substances 40% - tallow amine containing 25 oxyethylene un$\ 1*^ ^ r) V J \K*° JUL1989' - •••'•\i»i>f)*,vi'Ki/.->wMH'"Virif.,s".'>.V\?-fTjjn?ttt<?.1r}"{'S"5;T' V.,'*,ft."^vi^ ft 214880 - 21 - -precipitated synthetic silica , 10 g -polyvinylpyrrolidone 52 -bentonite q.s. 1002 Example 42; # 5 - active substances 402 /Ok - C13 alcohol containing 6 oxyethylene units 52 -precipitated synthetic silica 52 - ammonium sulphate 202 - hydroxyethyIcellulose 22 10 - starch q.s. 1002 Example 43" : - active substances 402 - nonylphenol containing 10 oxyethylene units 22 - calcium lignosulphonate 102 15 -polyvinylpyrrolidone 52 - kaolin q.s. 1002 The exact examples of active substances and special proportions to be produced according to these Examples 40' to 43 ' 3 r e similar to those for the mixtures of active sub-20 stances in Tables (II) and (V). In place of the wettable powders, pastes 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. 25 The aqueous dispersions and emulsions, e.g. the compositions obtained by diluting with water a wettable powder or a flowable accor O u . r-; v. 214B3® - 22 - invention, are included within the general 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 5 a "mayonnaise". All these dispersions, aqueous emulsions or G 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 the order of 10 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 (I) and the group B) are applied to the areas to be cleared of weeds-in a 15 single application; mixing of the two active substances can be carried out beforehand with dilution of the J ^ concentrate with water at the time of use, or extemporaneously by mixing two active substances or concentrates of active substances directly in the water 20 which is to serve for the application. According to another method of the invention, the compound of formula (I) and the compound of the group B) are applied sequentially: and the latter compounds can then optionally be applied on the soil. 25 Thus, the invention also provides a two component pack comprising a first component which comprises a herbicidally active substance of formula (I) as hereinbefore defined and a second component which comprises at least one herbicidally active substance of group B) as hereinbefore defined which can be applied simultaneously or separately. When sequential treatments 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 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 possess a green foliage. The herbicidal 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 (I) is 21 43 - 24 - applied at doses of between 0.1 and 10 kg/ha, 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. I 21488$ © I - 25 - J I j Thus, when a t r i a z i n e , e.g. atrazine, is used, it { /^s is preferably applied at between 0.125 and 4 kg/ha, the weight ratio of the compound of formula (I) to the tri-azine advantageously being between 1:32 and 32:1, prefer-5 ably between 1:16 and 8:1. 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 (I) to the phenylurea advantageously 10 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, 15 the weight ratio of the compound of formula (I) to the phenoxybenzoic 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 aci-f luorfen-sodium is used, it is preferably applied at 20 betwee-n 0.06 kg and 1 kg/ha, the weight ratio of the compound of formula (I) to the acifluorfen (sodium) most frequently being between 1:8 and 60:1, preferably between 1:4 and 32:1. When a uracil of the bromacil type is used, the 25 latter is applied at doses of between 0.125 and 10 kg/ha, and more especially between 0.125 and 3 kg/ha, the weight -ratio of the compound of formula (I) to the uracil O r - 26 - advantageously being between 1:80 and 32:1, preferably between 1:24 and 16:1. If a phenoxy acid derivative, e.g. 2,4-0, is used, 4 it is preferably applied at doses of between 0.1 and 5 kg/ha 5 and more especially between 0.1 and 2 kg/ha. The weight ratio of the compound of formula (I) to the phenoxy acid derivative is then advantageously between 1:40 and 40:1, preferably between 1:16 and 20:1. The phenoxy acid is advantageously used in the form of one of its alkali metal 10 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 be-tween 0.25 and 7 kg/ha, and more especially between 0.25 and 4 kg/ha, the weight 15 ratio of the compound of formula (I) to the carbamate generally being between 1:56 and 16:1, and more especially between 1:32 and 8:1. The asulam is preferably in the • form of an alkali metal salt, especially the spdium salt. When an aminotriazole is used, it is 20 preferably applied at between 0.5 and 4 kg/ha, the weight ratio of the compound of formula CI) to the aminotriazole generally being between 1:96 and 8:1, preferably between 1:32 and 4:1. If propanil is used, it ispreferably applied at between 25 0.25 and 6 kg/ha, the weight ratio of the compound of the formnlai I) to propanil advantageously being between 1:48 and 16:1, and preferably between 1:48 and 4:1. v. % ( ? • 6 21 - 27 - When quizalofop-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 (I) to the quizalofop-ethyl 5 then generally being between 1:8 and 250:1, and more advantageously between 1:4 and 60:1. 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 (I) 10 to diflufenican then generally being between 1:16 and 40:1, preferably between 1:6 and 20:1. If an imidazolinone herbicide is used, eg imazapur or imazaquin, the dose is preferably between 0.016 and 0.5 kg/ha, and the weight ratio of the 15 compound of formula (I) to the imidazolinone herbicide is most frequently between 1:4 and 250:1, more especially between 1:4 and 80:1. Imazapur is advantageously used in the form of its amine.salts, especially an isopropylamine salt. 20 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 (I) to-the benzonitrile derivative is advantageously between 1:8 and 60:1, preferably between 25 1:5 and 3 2:1. The bromoxynil can be in the form of alkali metal salts or advantageously in the form of esters (eg the octanoate) . Ioxynil 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 (I) to the thiadiazolylurea is most frequently between 1:56 and 32:1, especially between 1:16 and 8:1. 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 (I) to the derivative possessing an oxadiazole group is generally between 1:32 and 16:1, preferably between 1:20 and 8:1. 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 (I) to the oxadiazole then being 1:8 and 16:1, in particular between 1:8 and 8:1. When a benzoic acid, e.g. dicamba, is used, it is preferably applied at doses of between 0.05 and 5 kg/ha, preferably between 0.05 and 0.3 kg/ha, the weight ratio, of the compound of formula (I) 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. UMt.r<+)-Vl 2 1 488*6 - 29 - Thus pacaquat is preferably applied at between 0.125 and 2 kg/ha. The weight ratio of the compound of formula (I) to paraquat is generally between 1:16 and 32:1, more especially between .',l^ ' I 2148 8$ o 1 _ 30 _ | 1:8 and 16:1. j When the compound of formula (I) "is used with I | a triazine, especially good control of the following weeds | is observed: Xanthium pennsyLvanicum, Ipomea purpurea, 3 | 5 Polygonum convolvulus, Echinochloa crus-galli, Chenopodium, Amaranthus, S i nap i s, Capse11 a and Poa . When the compound of formula • (I) is used with a phenylurea, the activity is especially good on the following weeds: Abutilon theophrasti, Sesbania exaltata, 10 Xanthium pennsyLvanicum, Polygonum convolvuLus, Ipomea purpurea, Echinochloa crus-gaLLi, ALopecurus, Ape ra, Poa. AtripLex, S i n a p i s, Chenopodium, Chrysanthemum, Matricaria, Ranoncu L us and SteLLaria. When the compound of formula (I) is used with 15 phenoxybenzoic acid derivatives, good control of the following weeds is observed: Xanthium pennsyLvanicum, Ipomea purpurea, Sesbania exaltata, Abutilon theophrasti, Pol y -gonum convolvulus, Amaranthus, Chenopod ium, S i n a p i s, Datura, Sol anum, Se t a r i a , Euphorbia, B i dens and Gal i ns oga.. i'""**) 20 When the compound of '• formula (i) is used with a uracil, Xanthium pennsyLvanicum, Ipomea purpurea, Echinochloa crus-galli, Lolium multiflorum, Se t a r i a , Digitaria, Sromus, Ambros ia, Amaranthus, Agropyron, Cynodon, Taraxacum and P L antago are especially well controlled. 25 When the compound of formula (I) is used with the phenoxy acid derivative, good control of the following is observed: PortuL aca oleracea, Polygonum convolvulus. A?, , , 1 >-r - -.*. ...... ! ^ 21488-0 n\ /"~N - 31 " Abutilon theophrasti , Xanthium penns y I v an i c um, Chenopodiuin, ■ S i nap i s, So Ianum, Ramunc ulus, Amaranthus, C i rs i um and Ipomea. When the compound of formula (I) is used with 5 a carbamate such as asulam, Xanthium pennsyI vanicum, Abutilon theophrasti and Sesbania exaltata. Sorghum hale-pense, Pteridium, Aqu iIi n i c um, Eleus ine. Pan i cum, D i g i -t a r i a, S e t a r i a, Rumex and E qu i s e tum are especially well control led. 10 When the compound of formula (I) is used with aminotriazole, good control of Portulaca oleracea, Abutilon theophrasti, Ag r opy r on, Cynodon, Agrostis, A rTe m i s i a , A r i s -tolochia, Rumex, Oxa I is , Rubus, Equisetum, Lep i di'um and Tussilago is noted. 15 When the compound of formula (I) is used with amides such as propanil, the efficacy is good on Ipomea purpurea. Polygonum convolvulus and Abutilon theophrasti. •When the compound of formula (I) is used with phenoxypropionic derivatives such as quizalofop-ethyl, 20 good control of Lolium multiflorum and Echinochloa crus-gaL I i as well as Sesbania exaltata, Alopecurus, Digitaria, Hordeum, Panicum miliaceum, Se t ari a and Sorghum halepense is observed. When the compound of formula CI) is used with 25 diflufenican, the activity becomes especially good on the following weeds: Portulaca oleracea, Polygonum convolvulus, Abutilon theophrasti, Sesbania exaltata, Ech inochloa © 2148810) - 32 - crus-galli, Galium, Veronica, Stellaria, Matricaria, Anthemis, Chrysanthemum, Papaver rhoeas, Raphanus and S i nap i s . When the compound of formula (I) is used with 5 an imidazolinone, good control of the following is observed: Xanthium pennsyLvanicum, Ipomea purpurea, Portulaca oleracea, Sesbania exal tata, Echinochloa crus-galli, L o I i u m multiflorum, Amaranthus, Chenopodium, Ambros i a. Hibiscus, S i da, D i g i t a r i a, Eleusine, Setar i a, Cyperus esculentus, 10 Abutilon theophrasti and Polygonum. When the compound of formula (I) is used with a benzonitrile derivative, the efficacy is good on Ipomea purpurea, Portulaca oleracea, Polygonum convolvulus, Amaranthus, Chenopod ium, Sol anum, Ambros ia, Matr icaria, 15 Atriplex, S i n a p i s and Xanthium. When the compound of formula (I) is used with a thiadiazolylurea, the efficacy is good on the following weeds: Xanthium pennsyLvanicum, Ipomea purpurea, Polygonum convolvulus, Abutilon theophrasti, Sesbania exaltata, 20 Echinochloa crus-galli. Gallium, S i n a p i s, Stellaria, Chenopodium, Chrysanthemum, S e t a r i a and Poa. When the compound of formula (I) is used with herbicides of the oxadiazole family, especially good control of the following weeds is observed: Xanthium pennsyl-25 van i cum. Polygonum convolvulus, Ipomea purpurea, Echinochloa crus-galli, Amaranthus, Sinapis, Capsella, Euphorbia, Portulaca, Agropyron, Agrostis, Rubus, Festuca, Dactyl is, n^. _ :._ ( © 2 t 48 - 33 - Galium and Polentilla. When the compound of formula (I) is used with a quaternary ammonium derivative, the efficacy is good on Xanthium pennsylvanicum, Ipomea purpurea, Polygonum 5 convolvulus, Alopecurus, Setar ia, Sinapis, Raphanus, Chrysanthemum and Amaranthus. When the compound of formula (I) is used with a benzoic acid such as dicamba, good control of Ipomea, Xanthium, Chenopodium, Polygonum, Amaranthus, Abutilon, 10 Galium, Matricar ia, Stellar ia, 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 15 dicotyledonous. In Table (III) , 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 20 established or undergo good subsequent development, as well as to obtain satisfactory clearing of weeds from perennial crops (vines, orchards) . It is sometimes possible to improve the efficacy of weed clearing by carrying out sequential treatments, optionally involving 25 a soil treatment. The example which follows illustrates the invention and shows how it can be employed. i ' ,:.... . i... . i *-......- ^ n( • 214880 o (7) - 34 - Example 55: Post-sprouting herbicidal activity on plant species in the greenhouse. In pots 9 x 9 x 9 cm filled with light agricultural soil, a number of seeds are sown which is determined 5 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. 10 The stage of treatment for grasses is the "second leaf forming" 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 15 of mixture per pot corresponding to a volume of 500 l/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 water, so as to obtain the desired concentration, on the one hand a 20 formulation of the dispersible pellet type containing 20% of active substance of the c-onrp-ound 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 25 in the mixture, the dose of active substance applied varies according to the products, from 16 to 1000 g/ha. The treated pots are then placed in troughs 2 14880 k 1 ■M n - 35 - 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 5 living plants in the pots treated with the mixture con-taining 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 10 plants is thereby determined relative to the untreated control. A percentage destruction equal to 100% indicates that there has been complete destruction of the plant species in question, and a percentage of 0% indicates that the number of .living plants in the treated pot is identi-15 cal to that in the control pot. The plant species on which the tests were performed are indicated in Table (III) by the abbreviation adjacent to the latin name. The results obtained according to this Example 20 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 25 naturally leads to still better results. In many cases, the combinations according to the invention show a synergistic effect with respect to the active substances taken - 36 - in isolation. TABLE (III) I American name Latin name i 1 pigweed amaranthus retroflexus 1 I velvet leaf adutiion tneopnrasti(ASuJI 1 prickly siaa sida spinosa 1 1 1 sesoania 1 1 1 1 1 cocklebur xanthium pennsylvanicum I (XAN)| 1 1 Diaens I I 1 convolvulus arvensis 1 I 1 1 1 1 1 1 chickweed stellaria media 1 1 corn marigold cnrysantnemum segetum 1 I crabgrass digitaria sanguinalis I 1 giant foxtail setaria faoerii 1 1 black nigntsnade solanum nigrum 1 I 1 cyperus esculentus 1 I barnyard grass echinochloa crus-galli 1 (ECH) I ] wild oat avena fatua 1 I rye grass lolium multifiorum 1 1 black grass alopecurus myosuroloes 1 1 quack grass agropyron "repens 1 1 bermuda grass cynodon dactylon 1 I wild mustard sinapis arvensis 1 1 morning glory ipomea purpurea ) 1 •; x ■■ I I 21:4880 - 37 - I bindweed 1 1 calystegia sepium 1 1 blackberry 1 rubus fructicosus 1 1 purslane 1 portulaca oleracea (POR)j 1 wild buckwheat 1 polygonum convolvulus 1 (POL)I 1 hemp sesbania 1 sesoania exaltata (SESJ 1 < * 1 I , ,_L *'^ Common names A t r a z i n e 5 Isoproturon B i fenox 10 Bromacil 2,4-D Asulam Aminotriazole 15 Propanil Qu i zalofop-ethyI D i flufen ican 20 Ima2apur Acifluorfen-sodium 25 Bromoxynil 2 t 4880 - 38 - TABLE (IV) Chemical name (standard IUPAC nomencI a tu re) 2-chloro-4-ethylamino-6-isopropyl-amino-1/3,5-triazine 3-(4'-isopropylphenyl)-1,1-dimethyl-urea methyl 5-(2',4'-dichlorophenoxy)-2-n i trobenzoate 5-bromo-3-sec-butyl-6-methyluracil ammonium (2,4-dichlorophenoxy)acetate methyl 4-aminobenzenesulphonyl-carbamate (sodium salt) 3-amino-1H-1,2,4-triazole N-(3,4-dichlorophenyl)propionamide ethyl 2-C4-(6-chloro-2-quinoxalinyloxy)' phenyloxy]propionate N-(2,4-difluorophenyl)-2-(3-tri-fluoromethylphenoxy)nicotinamide isopropylammonium 2-C4,5-dihydro-4-methyl-4-(isopropyl)-5-oxo-1H-imidazol-2-yl]-3-pyridinecarboxylate sodium 5-C2'-chloro-4'-(trifluoro-methyl)phenoxy]-2-nitrobenzoate 3,5-dibromo-4-hydroxybenzonitrile oc tanoate a i.'k, -N <: - 39 - r^- . ! ' Eth id imuron Oxad i azon Paraquat 0 imefuron 10 0 i camba 1-(5-ethylsulphonyl-1,3,5~thiadiazol- 2-yl)-1,3-dimethylurea 5-tert-butyl-3-(2,,4,-dichLoro-5'-isopropyloxyphenyl)-1,3,4-oxadi-azolin-2-one 1,1'-dimethyl-4,4'-bipyridiniuin chlor ide 3-C2-chloro-4-(3,3-dimethylureido)-phenyl3-5-(1,1-dimethylethyl)-3H-1,3,4-okadiazol-2-one dimethylammonium 3,6-dichloro-2-methoxybenzoate ri 5 10 15 20 25 30 35 . 40 2 1 48 - 40- TABLE (V) Compound 1 of the group b) | nature [ dose Compound No. 1 1 in g/hal xan 1 ipo 1 1 por 1 pol | 1 i 1 1 250 250 1 90 1 98 1 100 l 90 1 1 atrazine T" 1 1 500 125 I 80 1100 1 100 1 100 1 1 T 1 1 500 250 1 100 1100 1 100 l 100 1 1 1 250 250 1 100 1 98 1 100 l 30 I 1 isopro- T 1 turon 1 500 125 I 90 1 50 1 100 1 20- 1 1 T i 1 500 250 I 90 1 98 1 100 1 60 1 1 1 1 1 500 250 I 90 1 90 1 100 1 100 1 1 difenox 1 1 1 1000 125 I 50 1 90 1 100 1 98 1 1 T 1 1 1000 250 I 70 I 90 I 100 1 100 1 1 1 1 1 125 250 1 60 1 50 " 1 100 1 98 1 1 dromacilT" 1 1 250 125 1 100 I 98 1 100 1 100 1 i r 1 1 250 250 I 100 1100 1 100 1 100 1 1 1 1 1 125 250 1 ldd 1100 I 100 1 80 1 1 2,4-0 T 1 1 250 125 1 100 1100 I 100 60 1 1 T" 250 250 1 100 1100 1100 • 1 98 1 1 asulam 1 1 1 500 250 1 100 1 20 1 10 1 20 1 1 amino- I 1 triazole1 1000 250. I 20 1 0 • 1 80 1 20 1 1 1 1 I 500 156 i 90 1 90 1 30 1 60 1 1 propanil! 1 1 1000 125 1 100 1 100 1 100 1 100 1 i r 1 1 1000 250 1 100 1100 I 90 1 100 1 1 quizalo-l 1 fop-ethyl 1 31 250 I 20 1 0 1 50 1 20 1 1 caroeta-l 1 mide 1 4000 250 1 20 I 90 I 30 1 10 I ! ^ 1 diflufe-l 1 nican 1 1000 250. 1 50 I 1 40 100 98 ! j 1 I 1 1 31 250 1 -100 1 $0 98 90 1 5 1 imazapur1 1 1 62 125 1 100 1 1 80 100 100 1 1 T 1 1 62 250 1 100 1 1 90 100 100 1 : 0 10 1 1 1 1 62 250 1 80 1 I 100 100 100 1 i 1 1acifluor-T 1 fen 1 125 125 1 100 1 1100 100 100 1 i i 1 sodium T 1 1 125 250 1 lod 1 1100 100 100 I 15 1 1 62 250 1 ltid l 1 '80 30 80 | ; 1 bromo- T 1 xynil ' 1 125 125 I 100 l 1100 0 90 1 20 1 1 125 250. 1 90 1 1100 90 100 1 1 1 1 1 125 250 1 100 1 1100 100 100 I 1 ' . 4 1 ethidi- 1 1 muron 1 250 125 1 lot) 1 1100 100 100 1 25 1 T 1 1 250 250 1 100 1 1100 100 100 1 1 1 1 1 250 250 1 100 1 1100 100 100 1 30 1 oxadia- T 1 zon 1 500 125 1 30 1 1 40 100 100 1 • . 1 1 500 250 1 100 1 1100 100 100 1 1 1 1 1 125 250 1 100 1 I 100 98 98 1 35 1 para- T 1 quat 1 250 125 1 98 1 1 50 .100 . 90 1 1 T 1 1 250 250 1 100 1 1 90 98 90 1 . 40 1 dimefu- 1 1 ron 1 1000 250 I I 30 1 1 10 100 90 I •*, ? * • | -~0 z 14-^0 - 42 - S TABLE (V) : O" 5 1 Compound 1 1 of the group b) ' 1 nature 1 dose in Compound 1 No. 1 I q/ha I ABU 1 SES 1 ECH | 1 I 1 1 1 250 1 250 I I 60 1 100 60 I I 10 1 atrazine T 1 1 500 1 125 1 1 1100 98 1 1 ] T 1 1 500 ! 250 1 1 1100 3b i 1 1 1 250 1 250 1 1 0 1 100 60 1 1 15 1 isopro- T 1 turon 1 500 ! 125 1 1 100 1 100 50 ! 1 1 T 1 1 500 | 250 1 1 iOO 1100 100 i 1 20 1 1 500 I 250 i 1 90 1100 20 1 1 1 bifenox 1 1 1 1000 1 125 1 1 100 1100 20 I 1 1 T 1 1 1000 I 250 | 1 100 1 98 20 I 1 25 1 1 1 1 125 1 250 1 1 ao 1 80 40 | 1 1 DromacilT 1 1 250 1 125 | 1 90 1 100 98 1 1 30 1 T 1 1 250 I 250 1 1 100 1100 100 1 1 1 I 1 1 125 1 250 1 1 80 1100 20 1 1 1 2,4-0 T 1 1 250 1 125 I 1 50 1100 10 1 1 35 1 T 1 1 250 I 250 ! 1 100 1100 50 1 1 1 asulam 1 1 1 500 I 250 1 1 90 1100 20 1 1 40 1 am^.no- 1 1 triazolel 1000 1 250 1 1 100 iioo 60. 1 1 1 I 1 1 500 t 250 1 1 60 1100 10 1 1 1 propanilT 1 1 1000 1 125 I 1 60 1 100 20 1 1 1 T 1 1 1000 1 250 | 1 95 1100 70 1 1 1 quizalo-l j foo-ethyl1 31 1 250 i 1 80 iioo 100 ! 1 1 caraeta-l 1 mide 1 4000 1 250 I 1 80 1100 20 1 1 </div>

Claims

<div class="application article clearfix printTableText" id="claims"> o - 43- 1 diflufe-l 1 nican I 1000 250 1 100 1 1100 1 80 I 1 1 1 1 1 31 250 1 100 1 90 1 90 I 1 5 1 imazapurl 1 1 62 125 1 100 1 1 95 1 90 1 1 1 T 1 1 62 250 1 100 1 1 95 1 100 I 1 10 1 1 1 1 62 • 250 • I ao 1 1100 1 20 1 1 {acifluor-T 1 fen 1 125 125 t 60 1 iioo 1 2d 1 1 1 sodium T 1 1 125 £50 1 80 1 1100 1 30 1 1 15 1 1 I 1 62 250 1 20 1 1 90 1 30 1 1 1 bromo- T 1 xynil 1 125 125 1 50 1 95 1 10 I 1 20 1 T 1 1 125 250 1 60 1 1 80 1 30 1 1 1 1 125 250 1 100 1 1 98 1 10 1 1 1 ethidi- 1 1 muron 1 250 125 1 100 1 1 95 1 10 1 1 25 1 T 1 1 250 250 1 100 1 IIOO 1 60 I 1 1 1 1 1 250 250 1 100 1 1100 1 90 I 1 30 1 oxadia- T 1 zon 1 500 125 1 100 1 1100 1 98 1 1 1 T 1 1 500 250 I 100 1 1100 1 100 1 1 1 1 1 1 125 250 1 100 1 1 100 1 100 1 35 1 para- T 1 quat 1 250 125 1 100 1 1 100 1 95 1 1 T 1 1 250 250 1 100 1 1 100 1 100 | 1 40 1 dimefu- 1 ! ron 1 1000 250 1 100 1 1 100 1 50 1 1 - 44 - 2 1 48 WHAT WE CLAIM IS:

1) A herbicidal composition comprising

A) an active herbicidal substance of formula:

OR2

' l

Q = p - CH2 - NH - Crt2 - CO - N - S02 - R (I)

1 , I

in which: OR ^

R1 denotes an optionally substituted hydrocarbon radical;

R denotes a hydrogen atom or is as defined for R*"; 2 3

R and R , which may be identical or different, denote

2 3

hydrogen atoms or are such that OR and OR ace 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, 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 substituted by halogen, phenyl, cyano, alkyl, alkoxy or

- I - - ,

;

a',

I ..„ 214880

- 45 -

alkyl carboxylate.

3) A composition according to claim 1 or 2

wherein the hydrocarbon radical represented by R*" is an alkyl, aryl or cycloalkyl radical. 5

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 10 preceding claims wherein R* represents an 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

15 containing from 1 to 4 carbon atoms.

7) A composition according to any one of the

2 3

preceding claims wherein R and R each represent an alkyl or aryl radical optionally substituted by halogen, phenyl, cyano, alkyl, alkoxy or alkyl carboxylate.

2

20

8) A composition according to claim 7 wherein R

and R"* each contain from 1 to 12 carborw atoms.

2

9) A composition according to claim 7 wherein R

3

and R each contain from 1 to 8 carbon atoms.

10) A composition according to any one of the 25 preceding claims wherein R and R1, which may be the same or different, each represent an alkyl radical having 1 to 4 carbon atoms and R and R , which may be the same

f*®'13WaWU»4U»^».

n j ■«,

'i

148

- 46 -

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 R^, which may be identical or

5 different, are alkyl radicals having 1 to 4 carbon atoms 2

and R is a hydrogen atom.

12) A composition according to any one of claims 1 to in which R and R*, which may be identical or different

2

•are alkyl radicals having 1 to 4 carbon atoms and R and 10 R^ are hydrogen atoms.

13) A composition according to any one of claims 1 to 12, in which the substance B) is alachlor,

metolachlor, simazine, atrazine, prometryne, diuron, isoproturon, linuron, tebuthiuron, ethidimuron,

15 sulfometuron, chlorsulfuron, metsulfuron,

methabenzthiazuron, oryzalin, trifluralin, diflufenican, napropamide, propanil, oxadiazon, dimefuron,

aminotriazole, picloram, bifenox, acifluorfen, acifluorfen-sodium, fomesafen, oxyfluorfen, esters of 20 acifluorfen and aliphatic alcohol, glycolate or lactate, quizalofop-ethyl, fluazifop-butyl, 2,4-D, 2,4-DP, MCPA, MCPP, dicamba, dalapon, metribuzin, carbetamide, EPTC, asulam, norflurazon, fluridone, diquat, paraquat,

bromacil, bromoxynil, ioxynil, imazaquin or- imazapur. 25

14) A composition according to any one of claims

1 to 13, in which the proportion of compound of formula (I) to the substance B) is from 0.2:1 to 10:1 by weight.

214880

- 47 -

15) A composition according to claim 14 in which the proDortion of compound of formula (I) to the-

/""N

substance B) is from 0.25:1 to 4:1 by weight.

16) A herbicidal composition according to any one 5 of claims 1 to 15 additionally comprising at least one inert carrier which is agriculturally acceptable.

j

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

10

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 13, which is in the form of a soluble powder, .

15 wettable powder or dry flowable.

20) A herbicidal composition substantially as hereinbefore defined with reference to any one of Examples 1 to 42-"

214880

rv

-48-

■21,) A method of combating weeds at a locus which comprises applying thereto an effective amount of a composition according to any one of claims 1 to 20.. 22) A method according to claim 21, whefein the

5 compound of formula (I) is applied in an amount

from 0.1 to 10 kg/ha.

CE 22) A method according to claim <22 wherein the compound of formula (I) is applied in an amount of from */ 0.1' to 4 kg/ha.

20 24^ A method according to claim 21

substantially as hereinbefore described.

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