(19) TZZ ¥ _T

(11) EP 2 632 265 B1

(12) EUROPEAN PATENT SPECIFICATION

(45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A01N 43/90 (2006.01) A01N 41/06 (2006.01) 11.01.2017 Bulletin 2017/02 A01P 13/00 (2006.01) A01N 57/20 (2006.01)

(21) Application number: 11837050.1 (86) International application number: PCT/US2011/057972 (22) Date of filing: 27.10.2011 (87) International publication number: WO 2012/058361 (03.05.2012 Gazette 2012/18)

(54) SYNERGISTIC HERBICIDAL COMPOSITION CONTAINING PENOXSULAM AND ORYZALIN SYNERGISTISCHE HERBIZIDZUSAMMENSETZUNG ENTHALTEND PENOXSULAM UND ORYZALIN COMPOSITION SYNERGIQUE CONTENANT DU PENOXSULAM ET DE L’ORYZALINE

(84) Designated Contracting States: (72) Inventor: MANN, Richard K. AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Franklin GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO IN 46131 (US) PL PT RO RS SE SI SK SM TR Designated Extension States: (74) Representative: f & e patent BA ME Fleischer, Engels & Partner mbB, Patentanwälte Braunsberger Feld 29 (30) Priority: 28.10.2010 US 407486 P 51429 Bergisch Gladbach (DE)

(43) Date of publication of application: (56) References cited: 04.09.2013 Bulletin 2013/36 WO-A2-2006/086640 WO-A2-2011/056631 WO-A2-2011/094386 WO-A2-2011/097187 (73) Proprietor: Dow AgroSciences LLC US-A1- 2009 042 728 US-A1- 2010 069 247 Indianapolis, IN 46268 (US)

Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 632 265 B1

Printed by Jouve, 75001 PARIS (FR) EP 2 632 265 B1

Description

[0001] This invention concerns a synergistic herbicidal composition containing (a) penoxsulam and (b) oryzalin in which the weight ratio of oryzalin to penoxsulam on an active indredient (ai) basis is form 40:1 to 960:1 for controlling 5 growth of undesirable vegetation, particularly in fruit trees, including pome fruit, stone fruit, tree nut, citrus, olives, gra pe- vines and other perennial fruit producing trees, as well as in turf, in sugar cane, in parks and alleyways, in range and pasture and in industrial vegetation management (IVM). [0002] The protection of crops from weeds and other vegetation which inhibit crop growth is a constantly recurring problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an 10 extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth. Chemical of many types have been disclosed in the literature and a large number are in commercial use. [0003] In some cases, herbicidal active ingredients have been shown to be more effective in combination than when applied individually and this is referred to as "synergism." As described in the Herbicide Handbook of the Weed Science Society of America, Ninth Edition, 2007, p. 429, "’synergism’ [is] an interaction of two or more factors such that the effect 15 when combined is greater than the predicted effect based on the response to each factor applied separately." Synergistic mixtures comprising penoxsulam are described in WO 2011/094386, WO 2011/056631, WO 2011/097187 and WO 2006/086640. The present invention is based on the discovery that oryzalin and penoxsulam, already known individually for their herbicidal efficacy, display a synergistic effect when applied in combination. [0004] The present invention concerns a synergistic herbicidal mixture comprising an herbicidally effective amount of 20 (a) penoxsulam and (b) oryzalin in which the weight ratio of oryzalin to penoxsulam on an active ingredient (ai) basis is from 40:1 to 960:1. The compositions may also contain an agriculturally acceptable adjuvant or carrier. [0005] The present invention also concerns a method of controlling the growth of undesirable vegetation, particularly in fruit trees, including pome fruit, stone fruit, tree nut, citrus, olives, grapevines and other perennial fruit producing tre es, as well as in turf, in sugar cane, in parks and alleyways, in range and pasture and in industrial vegetation management. 25 [0006] Penoxsulam is the common name for (2-(2,2-difluoroethoxy)- N-(5,8- dimethoxy-[1,2,4]triazolo[1,5-c]pyrimidin- 2-yl)-6- (trifluoromethyl)benzenesulfonamide. Its herbicidal activity is described in The Manual, Fifteenth Edi- tion, 2009. Penoxsulam controls barnyard grass, as well as many broadleaf and sedge weeds in rice, turf, tree nut and vineyard crops, cereal and grain crops, and IVM. [0007] Oryzalin is the common name for 4-(dipropylamino)-3,5-dinitrobenzenesulfonamide. 30 [0008] Its herbicidal activity is described in The Pesticide Manual, Fifteenth Edition, 2009. Oryzalin controls grasses and small seeded broad-leaved weeds in tree nut and vine crops, fruit trees, soybeans and turf. [0009] The term herbicide is used herein to mean an active ingredient that kills, controls or otherwise adversely modifies the growth of plants. An herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect and includes deviations from natural development, killing, regulation, desiccation, 35 retardation, and the like. The terms plants and vegetation include germinant seeds, emerging seedlings, plants emerging from vegetative propagules, and established vegetation. [0010] Herbicidal activity is exhibited by the compounds of the synergistic mixture when they are applied directly to the plant or to the locus of the plant at any stage of growth or before planting or emergence. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray 40 drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted as is known in the art to promote non-selective or selective herbicidal action. Generally, it is preferred to apply the composition of the present invention postemergence to relatively immature undesirable vegetation to achieve the maximum control of weeds. 45 [0011] In the composition of this invention, the active ingredient ratio (weigh-to-weight, wt:wt) of oryzalin to penoxsulam at which the herbicidal effect is synergistic is preferably 300:1. [0012] The rate at which the synergistic composition is applied will depend upon the particular type of weed to be controlled, the degree of control required, and the timing and method of application. In general, the composition of the invention can be applied at an application rate from about 2005 grams active ingredient per hectare (gai/ha) to about 50 4850 gai/ha based on the total amount of active ingredients in the composition. An application rate from about 2405 gai/ha to about 4850 gai/ha is preferred. In an especially preferred embodiment of the invention, oryzalin is applied at a rate from about 2400 gai/ha to about 4800 gai/ha, and penoxsulam is applied at a rate from about 6 gai/ha to about 35 gai/ha. [0013] The components of the synergistic mixture of the present invention can be applied either separately or as part 55 of a multipart herbicidal system. [0014] The synergistic mixture of the present invention can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied

2 EP 2 632 265 B1

sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the synergistic composition of the present invention include: 4-CPA, 4-CPB, 4-CPP, 2,4-D, 3,4-DA, 2,4-DB, 3,4-DB, 2,4- DEB, 2,4-DEP, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, , , , acrolein, , allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, , 5 , amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, , atraton, , azafeni- din, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, , benfuresate, ben- sulfuron, , bentazone, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, ben- zoylprop, benzthiazuron, bicyclopyrone, , bilanafos, bispyribac, borax, bromacil, bromobonil, bromobutide, bro- mofenoxim, , brompyrazon, , , butamifos, butenachlor, buthidazole, buthiuron, butralin, 10 butroxydim, buturon, butylate, , cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, car- basulam, carbetamide, carboxazole, chlorprocarb, carfentrazone, CDEA, CEPC, chlomethoxyfen, , chlo- ranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlo- rflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon, chlorotoluron, , chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate, clodina- 15 fop, clofop, , clomeprop, cloprop, cloproxydim, , cloransulam, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, , cycloate, cyclosulfamuron, cycloxydim, cycluron, cyhalofop, cyper- quat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, di- camba, dichlobenil, dichloralurea, dichlormate, , dichlorprop-P, diclofop, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimetham- 20 etryn, , dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, , di- noterb, diphenamid, dipropetryn, , disul, , diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz,EPTC, erbon, esprocarb, ethalfluralin,ethametsulfuron, ethidimuron, ethiolate,ethofumesate, ethoxyfen, ethox- ysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, , fenoxaprop, fenoxaprop-P, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, florasulam, , fluazifop-P, 25 fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr, flumetsulam, flumezin, flumiclorac, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, , flurtamone, fluthiacet, , foram- sulfuron, fosamine, furyloxyfen, , glufosinate-P, , halosafen, halosulfuron, haloxydine, haloxyfop, haloxyfop-P, hexachloroacetone, hexaflurate, , imazamethabenz, imazamox, , , ima- 30 zaquin, imazethapyr, imazosulfuron, indanofan, , iodobonil, iodomethane, iodosulfuron, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, , lenacil, , MAA, MAMA, MCPA, MCPA-thioethyl, MCPB, , mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, , metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthi- 35 azuron, methalpropalin, , methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bro- mide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, , metosulam, metoxuron, , metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, , nitrofluorfen, nor- flurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oxadiargyl, oxadiazon, oxapyrazon, ox- 40 asulfuron, oxaziclomefone, oxyfluorfen, parafluron, , pebulate, pelargonic acid, , pentachloroph- enol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phe- nobenzuron, phenylmercury acetate, , picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron, procyazine, prodiamine, profluazol, profluralin, profoxydim, proglinazine, , prometryn, , , propaquizafop, propazine, propham, propisochlor, propoxycarbazone, pro- 45 pyrisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen, pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazoxyfen, , pyributicarb, pyriclor, pyridafol, pyridate, pyrift- alid, pyriminobac, pyrimisulfan, pyrithiobac, pyroxasulfone, pyroxsulam, , quinmerac, quinoclamine, quinon- amid, quizalofop, quizalofop-P, rhodethanil, rimsulfuron, , S-metolachlor, sebuthylazine, secbumeton, sethox- ydim, siduron, , simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, 50 , sulfometuron, sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam, , tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, , terbutryn, tetrafluron, thenylchlor, thiazafluron,thiazopyr, thidiazimin, thidiazuron,thiencarbazone-methyl, thifensulfuron, thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron, tricamba, , tridiphane, trietazine, tri- floxysulfuron, , triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, 55 vernolate and xylachlor. [0015] The synergistic mixture of the present invention can additionally be employed to control undesirable vegetation in many crops that have been made tolerant to or resistant to them or to other herbicides by genetic manipulation or by mutation and selection. The synergistic mixture of the present invention can be used on acetolactate synthase inhibitor

3 EP 2 632 265 B1

tolerant crops. The synergistic composition of the present invention can, further, be used in conjunction with 2,4-D, glyphosate, glufosinate, , sulfonylureas or imidazolinones on 2,4-D tolerant, glyphosate-tolerant, glufosinate- tolerant, dicamba-tolerant, sulfonylurea-tolerant crops or imidazolinone-tolerant crops. It is generally preferred to use the synergistic composition of the present invention in combination with herbicides that are selective for the crop being 5 treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. It is further generally preferred to apply the synergistic composition of the present invention and other complementary herbicides at the same time, either as a combination formulation or as a tank mix. [0016] The synergistic composition of the present invention can generally be employed in combination with known herbicide safeners, such as benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, cyprosulfamate, 10 daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofen- im, furilazole, harpin proteins, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, MG 191, MON 4660, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. [0017] In practice, it is preferable to use the synergistic composition of the present invention in mixtures containing an herbicidally effective amount of the herbicidal components along with at least one agriculturally acceptable adjuvant 15 or carrier. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water dispersible granules, or wettable 20 powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. [0018] Suitable agricultural adjuvants and carriers that are useful in preparing the herbicidal mixtures of the invention are well known to those skilled in the art. Some of these adjuvants include, but are not limited to, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)); nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt;

blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C 9-C11alkylpolyglycoside; phosphated 25 alcohol ethoxylate; natural primary alcohol (C12-C16) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysi- loxane-methyl cap; nonylphenol ethoxylate + ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99. [0019] Liquid carriers that can be employed include water and organic solvents. The organic solvents typically used include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, 30 and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Specific organic solvents include 35 , xylene, petroleum naphtha, crop oil, , methyl ethyl ketone, cyclohexanone, trichloroethylene, perchlo- roethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol mono- methyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. Water is generally the carrier of choice for the dilution of concentrates. 40 [0020] Suitable solid carriers include talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, dia- tomaceous earth, lime, calcium carbonate, bentonite clay, Fuller’s earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, and the like. [0021] It is usually desirable to incorporate one or more surface-active agents into the compositions of the present invention. Such surface-active agents are advantageously employed in both solid and liquid compositions, especially 45 those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants conventionally used in the art of formulation and which may also be used in the present formulations are described, inter alia, in "McCutcheon’s Detergents and Emulsifiers Annual," MC Publishing Corp., Ridgewood, New Jersey, 1998 and in "Encyclopedia of Surfactants," Vol. I-III, Chemical Publishing Co., New York, 1980-81. Typical 50 surface-active agents include salts of alkyl sulfates, such as diethanolammonium lauryl sulfate; alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C 18 ethox- ylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C 16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as 55 lauryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono- and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseed/canola oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils,

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particularly methyl esters. [0022] Oftentimes, some of these materials, such as vegetable or seed oils and their esters, can be used interchange- ably as an agricultural adjuvant, as a liquid carrier or as a surface active agent. [0023] Other adjuvants commonly used in agricultural compositions include compatibilizing agents, antifoam agents, 5 sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilize r carriers such as ammonium nitrate, urea and the like. 10 [0024] The concentration of the active ingredients in the synergistic composition of the present invention is generally from 0.001 to 98 percent by weight. Concentrations from 0.01 to 90 percent by weight are often employed. In compositions designed to be employed as concentrates, the active ingredients are generally present in a concentration from 5 to 98 weight percent, preferably 10 to 90 weight percent. Such compositions are typically diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds or the locus of weeds generally contain 15 0.0001 to 1 weight percent active ingredient and preferably contain 0.001 to 0.05 weight percent. [0025] The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation water, and by other conventional means known to those skilled in the art. [0026] The following examples illustrate the present invention. 20 Examples

Evaluation of Postemergence Herbicidal Activity of Mixtures under Field Conditions

25 Methodology

[0027] Trials were conducted under field conditions in France. Trial sites were located in commercially grown European grape crop (Vitis vinifera). The grapes were grown using normal cultural practices for fertilization, seeding, and mainte- nance to ensure good growth of the crop and the weeds. The trials were conducted using normal research methodology. 30 Trial plots were between 2 to 4.5 meters (m) wide by 5.5 to 10 m long. All treatments were applied using a randomized complete block trial design with 3 or 4 replications per treatment. The trial sites had naturally occurring populations of weeds. The weed spectrum included, but was not limited to, black nightshadeSolanum ( nigrum; SOLNI), common lambsquarter (Chenopodium album; CHEAL), common groundsel Senecio( vulgaris; SENVU), round-leaved fluellen (Kickxia spuria; KICSP) and common purslane (Portulaca olerace;, POROL). 35 [0028] Treatments consisted of tank mixes of an oil dispersion of penoxsulam and commercially available formulations of oryzalin. Glyphosate was tank mixed with all treatments to provide complete foliar control of all weeds so that the residual weed control after application could be evaluated. The application volumes were between 150-325 liters per hectare (L/ha) of water. All application were made using precision gas hand sprayers using a 2 or 3 m boom using flat fan (80° or 110°) nozzles to broadcast the treatments on the soil. 40 Evaluation

[0029] The treated plots and control plots were rated blind at various intervals after application. Ratings were based of Percent (%) Visual weed control, where 0 corresponds to no injury and 100 corresponds to complete kill. 45 [0030] Data were collected for all trials and analyzed using various statistical methods. [0031] Colby’s equation was used to determine the herbicidal effects expected from the mixtures (Colby, S. R. Cal- culation of the synergistic and antagonistic response of herbicide combinations. Weeds 1967, 15, 20-22). [0032] The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B: 50

55 A = observed efficacy of active ingredient A at the same concentration as used in the mixture;

B = observed efficacy of active ingredient B at the same concentration as used in the mixture.

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[0033] The results are summarized in Tables 1 through 2.

Table 1. Synergistic weed control following an application of Penoxsulam + Oryzalin 56 to 109 days after application 5 Percent Control Application Rate (g ai/ha) SOLNI (1) SOLNI (2) CHEAL Penoxsulam Oryzalin Ob Ex Ob Ex Ob Ex

10 5.6 0 78---- - 0 3,0000---- - 5.6 3,000 99 78 - - - - 70--17-13- 15 02,400--25-13- 7 2,400 - - 94 38 43 24 SOLNI (1) -- 56 DAA, Bourdic, France SOLNI (2) -- 68 DAA, Eshallat, France 20 CHEAL - 109 DAA, Fronton, France SOLNI - black nightshade (Solanum nigrum) CHEAL - common lambsquarter (Chenopodium album) g ai/ha - grams of active ingredient per hectare Obs - percent control observed 25 Ex - percent control expected by Colby equation

Table 2. Synergistic weed control following an application of Penoxsulam + Oryzalin 103 days after application 30 in Fronton, France. Percent Control Application Rate (g ai/ha) POROL KICSP SENVU Penoxsulam Oryzalin Ob Ex Ob Ex Ob Ex 35 700 0 27 0 2,400 80 0 23 7 2,400 100 80 43 0 60 44

40 POROL - common purslane (Portulaca oleracea) KICSP - round-leaved fluellen (Kickxia spuria) SENVU - common groundsel (Senecio vulgaris) g ai/ha - grams of active ingredient per hectare Obs - percent control observed 45 Ex - percent control expected by Colby equation

Claims

50 1. A synergistic herbicidal mixture comprising an herbicidally effective amount of (a) penoxsulam and (b) oryzalin in which the weight ratio of oryzalin to penoxsulam on an active ingredient (ai) basis is from 40:1 to 960:1.

2. The synergistic herbicidal mixture of Claim 1 in which the weight ratio of oryzalin to penoxsulam on an active ingredient (ai) basis is 300:1. 55 3. A synergistic herbicidal composition comprising an herbicidally effective amount of the synergistic herbicidal mixture of Claim 1 and an agriculturally acceptable adjuvant or carrier.

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4. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with an herbicidally effective amount the synergistic herbicidal mixture of Claim 1.

5. The method of Claim 4, wherein the undesirable vegetation is controlled in fruit trees, including pome, stone, tree 5 nut, citrusand olives, grapevines,turf, sugar cane, parks and alleyways,range and pastureand inindustrial vegetation management.

6. The method of Claim 4 or 5, wherein the composition is applied at an application rate from 2005 grams active ingredient per hectare (gai/ha) to 4850 gai/ha based on the total amount of active ingredients in the composition, 10 preferably from 2405 gai/ha to 4850 gai/ha, wherein preferably oryzalin is applied at a rate from 2400 gai/ha to 4800 gai/ha, and penoxsulam is applied at a rate from 6 gai/ha to 35 gai/ha.

7. The method of any of Claims 4 to 6, wherein the mixture is applied in conjunction with one or more other herbicides, which are preferably selected from the group consisting of 4-CPA, 4-CPB, 4-CPP, 2,4-D, 3,4-DA, 2,4-DB, 3,4-DB, 15 2,4-DEB, 2,4-DEP, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, acetochlor, acifluorfen, aclonifen, acrolein, alachlor, al- lidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone, amidosulfuron, aminocy- clopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, benazolin, bencarbazone, benfluralin, benfuresate,bensulfuron, bensulide, bentazone,benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, 20 benzofluor, benzoylprop, benzthiazuron, bicyclopyrone, bifenox, bilanafos, bispyribac, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole, chlorprocarb, carfentrazone, CDEA, CEPC, chlomethoxy- fen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlo- 25 rfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, clethodim,cliodinate, clodinafop,clofop, clomazone,clomeprop, cloprop, cloproxydim, clopyralid, cloransulam,CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclosulfamuron, cy- cloxydim, cycluron, cyhalofop, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, 30 desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlorprop, dichlorprop-P, diclofop, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethamet- 35 sulfuron, ethidimuron, ethiolate, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxaprop, fenoxaprop-P, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, florasulam, fluazifop, fluazifop-P, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr, flumetsulam, flumezin, flumiclorac, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, 40 flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fu- ryloxyfen, glufosinate, glufosinate-P, glyphosate, halosafen, halosulfuron, haloxydine, haloxyfop, haloxyfop-P, hex- achloroacetone, hexaflurate, hexazinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, im- azethapyr, imazosulfuron, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isopro- 45 turon,isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop,karbutilate, ketospiradox,lactofen, lenacil, linuron, MAA, MAMA, MCPA, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, meso- prazine, mesosulfuron, mesotrione, metam, metamifop, metamitron, metazachlor, metazosulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methopro- tryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosu- 50 lam, metoxuron, metribuzin, metsulfuron, molinate, monalide, monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene, orthosulfamuron, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phen- 55 medipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picloram, picolinafen, pinoxaden, pip- erophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron, procyazine, prodi- amine, profluazol, profluralin, profoxydim, proglinazine, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyrisulfuron, propyzamide, prosulfalin, prosulfocarb, pro-

7 EP 2 632 265 B1

sulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen, pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazox- yfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyriftalid, pyriminobac, pyrimisulfan, pyrithiobac, py- roxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, quizalofop, quizalofop-P, rhodethanil, rimsulfuron, saflufenacil, S-metolachlor, sebuthylazine, secbumeton, , siduron, simazine, simeton, sim- 5 etryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosulfuron, sulfuric acid, sulglycapin, swep, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin, thidiazuron, thiencarbazone-methyl, thifensulfuron, thiobencarb, tiocarbazil, tioclorim, topramezone, tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron, tricamba, triclopyr, tridiphane, trietazine, trifloxysulfuron, 10 trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron, vernolate and xylachlor.

8. The method of any of Claims 4 to 7, wherein the undesirable vegetation is controlled in crops that have been made tolerant to or resistant to the herbicides of the mixture or to other herbicides by genetic manipulation or by mutation 15 and selection, preferably in acetolactate synthase inhibitor tolerant crops or in conjunction with 2,4-D, glyphosate, glufosinate, dicamba, sulfonylureas or imidazolinones on 2,4-D tolerant, glyphosate-tolerant, glufosinate-tolerant, dicamba-tolerant, sulfonylurea-tolerant crops or imidazolinone-tolerant crops.

9. The method of any of Claims 4 to 8, wherein the mixture is employed in combination with a herbicide safener, 20 preferably selected from the group consisting of benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyo- metrinil, cyprosulfamate, daimuron, dichlormid, dicyclonon, dietholate, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, mefenpyr-diethyl, mephenate, MG 191, MON 4660, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides.

25 10. The method of any of Claims 4 to 9, wherein the mixture further comprises at least one agriculturally acceptable adjuvant or carrier.

11. The composition of Claim 3 or the method of Claim 10, wherein the mixture or the composition is in form of a solid, preferably selected from dusts, granules, water dispersible granules, and wettable powders, or a liquid, preferably 30 selected from emulsifiable concentrates, solutions, emulsions, and suspensions.

12. The composition or the method of any of Claims 3, 10 or 11, wherein the adjuvants are selected from the group consisting of crop oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt; blend of petroleum hydrocarbon, alkyl esters, organic acid, anionic surfactant; C 9-C11 alkylpolyglycoside; phosphated 35 alcohol ethoxylate; natural primary alcohol (C 12-C16) ethoxylate; di-sec-butylphenol EO-PO block copolymer; polysi- loxanemethyl cap; nonylphenol ethoxylate + urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8EO); tallow amine ethoxylate (15 EO); PEG(400) dioleate-99, compatibilizing agents, anti- foam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, and 40 antimicrobial agents.

13. The composition or the method of any of Claims 3 or 10 to 12, wherein the liquid carrier is selected from water and organic solvents, the organic solvent preferably being selected from the group consisting of petroleum fractions, hydrocarbons, vegetable oils, esters of these vegetable oils, esters of monoalcohols or dihydric, trihydric, or other 45 4-6 hydroxy containing polyalcohols, and esters of mono, di and polycarboxylic acids, more preferably being selected from the group consisting of mineral oil, aromatic solvents, paraffinic oils, soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil; 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di- butyl adipate, di-octyl phthalate; even more preferably being selected from the group consisting of toluene, xylene, 50 petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether, diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl- 2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, and liquid fertilizers and the solid carriers are selected from the group consisting of talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous 55 earth, lime, calcium carbonate, bentonite clay, Fuller’s earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, and lignin.

14. The synergistic herbicidal mixture, the composition or the method of any of the preceding Claims, wherein the mixture

8 EP 2 632 265 B1

or composition further comprises one or more surface-active agents, preferably being selected from the group consisting of salts of alkyl sulfates, alkylarylsulfonate salts, alkylphenol-alkylene oxide addition products, alcohol- alkylene oxide addition products, soaps, alkylnaphthalene-sulfonate salts, dialkyl esters of sulfosuccinate salts, sorbitol esters, quaternary amines, polyethylene glycol esters of fatty acids, block copolymers of ethylene oxide and 5 propylene oxide;salts of mono- and dialkyl phosphate esters; vegetableor seed oils and estersof these vegetableoils.

15. The synergistic herbicidal mixture, the composition or the method of any of the preceding Claims, wherein the mixture or composition further contains other herbicides, plant growth regulants, fungicides, insecticides, liquid fertilizers, or solid, particulate fertilizer carriers. 10

Patentansprüche

1. Eine synergistische herbizide Mischung umfassend eine herbizid wirksame Menge von (a) Penoxsulam und (b) 15 Oryzalin, in welcher das Gewichtsverhältnis von Oryzalin zu Penoxsulam auf einer Wirkstoffbasis (ai) von 40:1 bis 960:1 beträgt.

2. Die synergistische herbizide Mischung gemäß Anspruch 1, in welcher das Gewichtsverhältnis von Oryzalin zu Penoxsulam auf einer Wirkstoffbasis (ai) 300:1 beträgt. 20 3. Eine synergistische herbizide Zusammensetzung umfassend eine herbizid wirksame Menge der synergistischen herbiziden Mischung gemäß Anspruch 1 und einen landwirtschaftlich akzeptablen Hilfs- oder Trägerstoff.

4. Ein Verfahren zur Bekämpfung unerwünschter Vegetation, welches das In-Kontakt-Bringen der Vegetation oder 25 des Ortes derselben mit einer herbizid wirksamen Menge der synergistischen herbiziden Mischung gemäß Anspruch 1 umfasst.

5. Das Verfahren gemäß Anspruch 4, wobei die unerwünschte Vegetation in Obstbäumen, inklusive Kernobst, Stein- obst, Schalenfrüchten, Zitrusfrüchten und Oliven, Wein, Rasen, Zuckerrohr, Parks und Alleen, Wiesen- und Wei- 30 deland und im industriellen Vegetationsmanagement bekämpft wird.

6. Das Verfahren gemäß Anspruch 4 oder 5, wobei die Zusammensetzung in einer Anwendungsmenge von 2.005 Gramm Wirkstoff pro Hektar (gai/ha) bis 4.850 gai/ha, bezogen auf die Gesamtmenge an Wirkstoffen in der Zusam- mensetzung, angewandt wird, vorzugsweise von 2.405 gai/ha bis 4.850 gai/ha, wobei vorzugsweise Oryzalin in 35 einer Menge von 2.400 gai/ha bis 4.800 gai/ha aufgebracht wird und Penoxsulam in einer Menge von 6 gai/ha bis 35 gai/ha aufgebracht wird.

7. Das Verfahren gemäß einem der Ansprüche 4 bis 6, wobei die Mischung zusammen mit einem oder mehreren weiteren Herbiziden angewandt wird, die vorzugsweise aus der Gruppe bestehend aus 4-CPA, 4-CPB, 4-CPP, 2,4- 40 D, 3,4-DA, 2,4-DB, 3,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, Acetochlor, Acifluorfen, Aclo- nifen, Acrolein, Alachlor, Allidochlor, Alloxydim, Allylalkohol, Alorac, Ametridion, Aametryn, Amibuzin, Amicarbazon, Amidosulfuron, Aminocyclopyrachlor, Aminopyralid, Amiprofos-Methyl, Amitrol, Ammoniumsulfamat, Anilofos, Ani- suron, Asulam, Atraton, Atrazin, Azafenidin, Azimsulfuron, Aziprotryn, Barban, BCPC, Beflubutamid, Benazolin, Bencarbazon, Benfluralin, Benfuresat, Bensulfuron, Bensulid, , Benzadox, Benzfendizon, Benzipram, Ben- 45 zobicyclon, Benzofenap, Benzofluor, Benzoylprop, Benzthiazuron, Bicyclopyron, Bifenox, Bilanafos, Bispyribac, Borax, Bromacil, Bromobonil, Bromobutid, Bromfenoxim, Bromoxynil, Brompyrazon, Butachlor, Butafenacil, Buta- mifos, Butenachlor, Buthidazol, Buthiuron, Butralin, Butroxydim, Buturon, Butylat, Dimethylarsinsäure, Cafenstrol, Calciumchlorat, Calciumcyanamid, Cambendichlor, Carbasulam, Carbetamid, Carboxazol, Chlorprocarb, Carfen- trazon, CDEA, CEPC, Chlomethoxyfen, Chloramben, Chloranocryl, Chlorazifop, Chlorazin, Chlorbromuron, Chlor- 50 bufam, Chloreturon, Chlorfenac, Chlorfenprop, Chlorflurazol, Chlorflurenol, Chloridazon, Chlorimuron, Chlornitrofen, Chloropon, , Chloroxuron, Chloroxynil, Chlorpropham, Chlorsulfuron, Chlorthal, Chlorthiamid, Cinidon- Ethyl, Cinmethylin, Cinosulfuron, Cisanilid, Clethodim, Cliodinat, Clodinafop, Clofop, Clomazon, Clomeprop, Clop- rop, Cloproxydim, Clopyralid, Cloransulam, CMA, Kupfersulfat, CPMF, CPPC, Credazin, Kresol, Cumyluron, Cya- natryn, Cyanazin, Cycloat, Cyclosulfamuron, Cycloxydim, Cycluron, Cyhalofop, Cyperquat, Cyprazin, Cyprazol, 55 Cypromid, Daimuron, Dalapon, Dazomet, Delachlor, Desmedipham, Desmetryn, Diallat, Dicamba, Dichlobenil, Di- chloralharnstoff, Dichlormat, Dichlorprop, Dichlorprop-P, Diclofop, Diclosulam, Diethamquat, Diethatyl, Difenopen- ten, Difenoxuron, Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperat, Dimethachlor, Dimethametryn, Dimethenamid, Dimethenamid-P, Dimexan, Dimidazon, Dinitramin, Dinofenat, Dinoprop, Dinosam, Dinoseb, Dino-

9 EP 2 632 265 B1

terb, Diphenamid, Dipropetryn, Diquat, Disul, Dithiopyr, Diuron, DMPA, DNOC, DSMA, EBEP, Eglinazin, Endothal, Epronaz, EPTC, Erbon, Esprocarb, Ethalfluralin, Ethametsulfuron, Ethidimuron, Ethiolat, Ethofumesat, Ethoxyfen, Ethoxysulfuron, Etinofen, Etnipromid, Etobenzanid, EXD, Fenasulam, Fenoprop, Fenoxaprop, Fenoxaprop-P, Fen- oxasulfon, Fenteracol, Fenthiaprop, Fentrazamid, Fenuron, Eisen(II)sulfat, Flamprop, Flamprop-M, Florasulam, Flu- 5 azifop, Fluazifop-P, Fluazolat, Flucarbazon, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenican, Flufenpyr, Flu- metsulam, Flumezin, Flumiclorac, Flumi-oxazin, Flumipropyn, Fluometuron, Fluordifen, Fluorglycofen, Fluoromidin, Fluoronitrofen, Fluothiuron, Flupoxam, Flupropacil, Flupropanat, Flupyrsulfuron, Fluridon, Flurochloridon, Fluroxy- pyr, Flurtamon, Fluthiacet, Fomesafen, Foramsulfuron, Fosamin, Furyloxyfen, Glufosinat, Glufosinat-P, Glyphosat, Halosafen, Halosulfuron, Haloxydin, Haloxyfop, Haloxyfop-P, Hexachloraceton, Hexaflurat, Hexazinon, Imazame- 10 thabenz, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Indanofan, Indaziflam, lodobonil, lodmethan, Iodsulfuron, lofensulfuron, loxynil, Ipazin, Ipfencarbazon, Iprymidam, Isocarbamid, Isocil, Isomethiozin, Isonoruron, Isopolinat, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortol, Isoxaflutol, Isoxapyrifop, Karbu- tilat, Ketospiradox, Lactofen, Lenacil, Linuron, MAA, MAMA, MCPA, MCPA-thioethyl, MCPB, Mecoprop, Mecoprop- P, Medinoterb, Mefenacet, Mefluidid, Mesoprazin, Mesosulfuron, Mesotrion, Metam, Metamifop, Metamitron, Me- 15 tazachlor, Metazosulfuron, Metflurazon, Methabenzthiazuron, Methalpropalin, Methazol, Methiobencarb, Methio- zolin, Methiuron, Methometon, Methoprotryn, Methylbromid, Methylisothiocyanat, Methyldymron, Metobenzuron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron, Molinat, Monalid, Monisouron, Mo- nochloressigsäure, Monolinuron, Monuron, Morfamquat, MSMA, Naproanilid, Napropamid, Naptalam, Neburon, Nicosulfuron, Nipyraclofen, Nitralin, Nitrofen, Nitrofluorfen, Norflurazon, Noruron, OCH, Orbencarb, ortho-Dichlor- 20 benzol, Orthosulfamuron, Oxadiargyl, Oxadiazon, Oxapyrazon, Oxasulfuron, Oxaziclomefon, Oxyfluorfen, Paraflu- ron, Paraquat, Pebulat, Pelargonsäure, Pendimethalin, Pentachlorphenol, Pentanochlor, Pentoxazon, Perfluidon, Pethoxamid, Phenisopham, Phenmedipham, Phenmedipham-Ethyl, Phenobenzuron, Phenylquecksilberacetat, Pic- loram, Picolinafen, Pinoxaden, Piperophos, Kaliumarsenit, Natriumazid, Kaliumcyanat, Pretilachlor, Primisulfuron, Procyazin, Prodiamin, Profluazol, Profluralin, Profoxydim, Proglinazin, Prometon, Prometryn, Propachlor, Propanil, 25 Propaquizafop, Propazin, Propham, Propisochlor, Propoxycarbazon, Propyrisulfuron, Propyzamid, Prosulfalin, Pro- sulfocarb, Prosulfuron, Proxan, Prynachlor, Pydanon, Pyraclonil, Pyraflufen, Pyrasulfotol, Pyrazolynate, Pyrazosul- furon, Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyriclor, Pyridafol, Pyridat, Pyriftalid, Pyriminobac, Pyrimisulfan, Pyrithiobac, Pyroxasulfon, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamin, Quinonamid, Quizalofop, Quizalofop- P, Rhodethanil, Rimsulfuron, Saflufenacil, S-Metolachlor, Sebuthylazin, Secbumeton, Sethoxydim, Siduron, Sima- 30 zin, Simeton, Simetryn, SMA, Natriumarsenit, Natriumazid, Natriumchlorat, Sulcotrion, Sulfallat, Sulfentrazon, Sul- fometuron, Sulfosulfuron, Schwefelsäure, Sulglycapin, Swep, TCA, Tebutam, Tebuthiuron, Tefuryltrion, Tembotrion, Tepraloxydim, Terbacil, Terbucarb, Terbuchlor, Terbumeton, Terbuthylazin, Terbutryn, Tetrafluron, Thenylchlor, Thiazafluron, Thiazopyr, Thidiazimin, Thidiazuron, Thiencarbazon-Methyl, Thifensulfuron, Thiobencarb, Tiocarbazil, Tioclorim, Topramezon, Tralkoxydim, Triallat, Triasulfuron, Triaziflam, Tribenuron, Tricamba, Triclopyr, Tridiphan, 35 Trietazin, Trifloxysulfuron, Trifluralin, Triflusulfuron, Trifop, Trifopsim, Trihydroxytriazin, Trimeturon, Tripropindan, Tritac, Tritosulfuron, Vernolat und Xylachlor ausgewählt ist.

8. Das Verfahren gemäß einem der Ansprüche 4 bis 7, wobei die unerwünschte Vegetation in Nutzpflanzen bekämpft wird, die gegenüber den Herbiziden der Mischung oder weiteren Herbiziden mittels genetischer Manipulation oder 40 durch Mutation und Selektion tolerant oder resistent gemacht wurden, vorzugsweise in Acetolactatsynthaseinhibitor- toleranten Nutzpflanzen oder zusammen mit 2,4-D, Glyphosat, Glufosinat, Dicamba, Sulfonylharnstoffen oder Imi- dazolinonen auf 2,4-D-toleranten, Glyphosattoleranten, Gluphosinat-toleraten, Dicamba-toleranten, Sulfonylharn- stofftoleranten Nutzpflanzen oder Imidazolinon-toleranten Nutzpflanzen.

45 9. Das Verfahren gemäß einem der Ansprüche 4 bis 8, wobei die Mischung in Kombination mit einem Herbizid-Safener verwendet wird, vorzugsweise ausgewählt aus der Gruppe bestehend aus Benoxacor, Benthiocarb, Brassinolid, Cloquitocet (Mexyl), Cyometrinil, Cyprosulfamat, Daimuron, Dichlormid, Dicyclonon, Dietholat, Dimepiperat, Disul- foton, Fenchlorazol-Ethyl, Fenclorim, Flurazol, Fluxofenim, Furilazol, Harpin-Proteinen, Isoxadifen-Ethyl, Mefenpyr- Diethyl, Mephenat, MG 191, MON 4660, Naphthalinsäureanhydrid (NA), Oxabetrinil, R29148 undN -Phenylsulfo- 50 nylbenzoesäureamiden.

10. Das Verfahren gemäß einem der Ansprüche 4 bis 9, wobei die Mischung weiterhin mindestens einen landwirtschaft- lich akzeptablen Hilfs- oder Trägerstoff umfasst.

55 11. Die Zusammensetzung gemäß Anspruch 3 oder das Verfahren gemäß Anspruch 10, wobei die Mischung oder die Zusammensetzung in Form eines Feststoffs, vorzugsweise aus Stäuben, Granulaten, wasserdispergierbaren Gra- nulaten und wasserdispergierbaren Pulvern ausgewählt, oder in Form einer Flüssigkeit, vorzugsweise aus emul- gierbaren Konzentraten, Lösungen, Emulsionen und Suspensionen ausgewählt, vorliegt.

10 EP 2 632 265 B1

12. Die Zusammensetzung oder das Verfahren gemäß einem der Ansprüche 3, 10 oder 11, wobei die Hilfsstoffe aus der Gruppe bestehend aus Crop-Öl-Konzentrat, Nonylphenolethoxylat; quartärem Benzylcocoalkyldimethylammo- niumsalz; Mischung von Erdölkohlenwasserstoffen, Alkylestern, organischer Säure, anionischem oberflächenakti- vem Mittel; 9-C C11-Alkylpolyglycosid; phosphatiertem Alkoholethoxylat; natürlichem primärem Alko- 5 hol(C12-C16)ethoxylat; di-sec-Butylphenol/EO-PO-Blockcopolymer; methylverkapptem Polysiloxan; Nonylphenyle- thoxylat + Harnstoffammoniumnitrat; emulgiertem methylierten Samenöl; Tridecylalkohol(synthetisches)ethoxylat (8EO); Talkaminethoxylat (15 EO); PEG(400)-Dioleat-99, Kompatibilisierungsmitteln; Schauminhibitoren, Komple- xierungsmitteln; Neutralisierungsmitteln und Puffern; Korrosionsinhibitoren; Farbstoffen; Duftstoffen, Spreitmitteln, Penetrierhilfen, Anhaftmitteln, Dispergiermitteln, Verdickungsmitteln, Gefrierpunkterniedrigern und antimikrobiellen 10 Mitteln ausgewählt sind.

13. Die Zusammensetzung oder das Verfahren gemäß einem der Ansprüche 3 oder 10 bis 12, wobei der flüssige Trägerstoff aus Wasser und organischen Lösungsmitteln ausgewählt ist, wobei das organische Lösungsmittel vor- zugsweise aus der Gruppe bestehend aus Erdölfraktionen, Kohlenwasserstoffen, pflanzlichen Ölen, Estern dieser 15 pflanzlichen Öle, Estern von Monoalkoholen oder zweiwertigen, dreiwertigen oder anderen, 4 bis 6 Hydroxygruppen enthaltenden Polyalkoholen und Estern von Mono-, Di- und Polycarbonsäuren ausgewählt ist, bevorzugter aus der Gruppe bestehend aus Mineralöl, aromatischen Lösungsmitteln, paraffinischen Ölen, Sojaöl, Rapssamenöl, Oli- venöl, Rizinusöl, Sonnenblumenöl, Kokosnussöl, Mailöl, Baumwollsamenöl, Leinsamenöl, Palmöl, Erdnussöl, Saf- floröl, Sesamöl, Tungöl; 2-Ethylhexylstearat, n-Butyloleat, Isopropylmyristat, Propylenglykoldioleat, Dioctylsuccinat, 20 Dibutyladipat, Dioctylphthalat ausgewählt ist, noch bevorzugter aus der Gruppe bestehend aus Toluol, Xylol, Erd- ölnaphtha, Cropöl, Aceton, Methylethylketon, Cyclohexanon, Trichlorethylen, Perchlorethylen, Ethylacetat, Amyla- cetat, Butylacetat, Propylenglykolmonomethylether, Diethylenglykolmonomethylether, Methylalkohol, Ethylalkohol, Isopropylalkohol, Amylalkohol, Ethylenglykol, Propylenglykol, Glycerin, N-Methyl-2-pyrrolidinon, N,N-Dimethylalky- lamiden, Dimethylsulfoxid und flüssigen Düngemitteln ausgewählt ist und die festen Trägerstoffe aus der Gruppe 25 bestehend aus Talk, Pyrophyllitton, Siliciumoxid, Attapulgit-Ton, Kaolinton, Kieselguhr, Kreide, Diatomeenerde, Kalk, Calciumcarbonat, Bentonitton, Fullererde, Baumwollsamenhülsen, Weizenmehl, Sojamehl, Bimsstein, Holz- mehl, Walnussschalenmehl und Lignin ausgewählt sind.

14. Die synergistische herbizide Mischung, die Zusammensetzung oder das Verfahren gemäß einem der vorhergehen- 30 den Ansprüche, wobei die Mischung oder die Zusammensetzung weiterhin ein oder mehrere oberflächenaktive Mittel umfasst, die vorzugsweise aus der Gruppe bestehend aus Salzen von Alkylsulfaten, Alkylarylsulfonatsalzen, Alkylphenol-Alkylen-oxid-Additionsprodukten, Alkohol-Alkylenoxid-Additionsprodukten, Seifen, Alkylnaphalinsulfo- natsalzen, Dialkylestern von Sulfosuccinatsalzen, Sorbitolestern, quartären Aminen, Polyethylenglykolestern von Fettsäuren, Blockcopolymeren von Ethylenoxid und Propylenoxid, Salzen von Mono- und Dialkylphosphatestern, 35 Pflanzen- oder Samenölen und Estern dieser Pflanzenöle ausgewählt ist.

15. Die synergistische herbizide Mischung, die Zusammensetzung oder das Verfahren gemäß einem der vorhergehen- den Ansprüche, wobei die Mischung oder Zusammensetzung weiterhin andere Herbizide, Pflanzenwachstumsre- gulatoren, Fungizide, Insektizide, flüssige Düngemittel oder feste, partikelförmige Düngemittelträger umfasst. 40

Revendications

1. Mélange herbicide synergique comprenant, en quantité à effet herbicide, 45 a) du penoxsulame, b) et de l’oryzalin, dans lequel le rapport pondéral de l’oryzalin au penoxsulame, en ingrédients actifs (ia), vaut de 40/1 à 960/1. 50 2. Mélange herbicide synergique conforme à la revendication 1, dans lequel le rapport pondéral de l’oryzalin au pe- noxsulame, en ingrédients actifs (ia), vaut 300/1.

3. Composition herbicide synergique comprenant, en une quantité à effet herbicide, un mélange herbicide synergique 55 conforme à la revendication 1, et un adjuvant ou véhicule admissible en agriculture.

4. Procédé de lutte contre des végétaux indésirables, comportant le fait de mettre ces végétaux, ou un endroit où ils poussent, en contact avec un mélange herbicide synergique conforme à la revendication 1, utilisé en une quantité

11 EP 2 632 265 B1

à effet herbicide.

5. Procédé conforme à la revendication 4, dans lequel on lutte contre des végétaux indésirables dans des cultures d’arbres fruitiers, y compris d’arbres à fruits à pépins, à fruits à noyaux, à fruits amandes, d’agrumes et d’oliviers, 5 des vignes, du gazon, des champs de canne à sucre, des parcs, des allées, des prairies ou des pâturages, ou sur des sites d’aménagement végétal intégré.

6. Procédé conforme à la revendication 4 ou 5, dans lequel on applique la composition à un taux, calculé en quantité totale d’ingrédients actifs dans la composition, de 2005 à 4850 gia/ha (grammes d’ingrédients actifs par hectare), 10 de préférence de 2405 à 4850 gia/ha, étant entendu que de préférence, l’oryzalin est appliqué à un taux de 2400 à 4800 gia/ha, et le pénoxsulame est appliqué à un taux de 6 à 35 gia/ha.

7. Procédé conforme à l’une des revendications 4 à 6, dans lequel le mélange est appliqué conjointement avec un ou plusieurs autre(s) herbicide(s), choisi(s) de préférence dans l’ensemble formé par les suivants : 4-CPA, 4-CPB, 4- 15 CPP, 2,4-D, 3,4-DA, 2,4-DB, 3,4-DB, 2,4-DEB, 2,4-DEP, 3,4-DP, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, acétochlore, aci- fluorfène, aclonifène, acroléine, alachlore, allidochlore, alloxydime, alcool allylique, alorac, amétridione, amétryne, amibuzine, amicarbazone, amidosulfuron, aminocyclopyrachlore, aminopyralide, amiprofosméthyl, amitrole, sulfa- mate d’ammonium, anilofos, anisuron, asulame, atraton, atrazine, azafénidine, azimsulfuron, aziprotryne, barbane, BCPC, béflubutamide, bénazoline, bencarbazone, benfluraline, benfurésate, bensulfuron, bensulide, bentazone, 20 benzadox, benzfendizone, benziprame, benzobicyclone, benzofénap, benzofluor, benzoylprop, benzthiazuron, bi- cyclopyrone, bifénox, bilanafos, bispyribac, borax, bromacil, bromobonil, bromobutide, bromophénoxime, bromoxy- nil, brompyrazone, butachlor, butafénacile, butamifos, buténachlore, buthidazole, buthiuron, butraline, butroxydime, buturon, butilate, acide cacodylique, cafenstrole, chlorate de sodium, cyanamide calcique, cambendichlore, carba- sulam, carbétamide, carboxazole, chlorprocarbe, carfentrazone, CDEA, CEPC, chlométhoxyfène, chlorambène, 25 chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufame, chloréturon, chlorfénac, chlorfenprop, chloroflu- razole, chlorflurénol, chloridazone, chlorimuron, chlornitrofène, chloropon, chlortoluron, chloroxuron, chloroxynil, chlorprophame, chlorsulfuron, chlorthal, chlortiamide, cinidon-éthyl, cinméthyline, cinosulfuron, cisanilide, cléthodi- me, cliodinate, clodinafop, clofop, clomazone, cloméprop, cloprop, cloproxydime, clopyralid, cloransulame, CMA, sulfate de cuivre, CPMF, CPPC, crédazine, crésol, cumyluron, cyanatrine, cyanazine, cycloate, cyclosulfamuron, 30 cycloxydime, cycluron, cyhalofop, cyperquat, cyprazine, cyprazole, cypromide, daimuron, dalapon, dazomet, déla- chlore, desmédiphame, desmétryne, diallate, dicamba, dichlobénil, dichloralurée, dichlormate, dichlorprop, dichlor- prop-P, diclofop, diclosulame, diéthamquat, diéthatyl, difénopentène, difénoxuron, difenzoquat, diflufénican, diflu- fenzopyr, diméfuron, dimépipérate, diméthachlore, diméthamétryne, diméthénamide, diméthénamide-P, diméxano, dimidazone, dinitramine, dinofénate, dinoprop, dinosame, dinosèbe, dinoterbe, difénamide, dipropétryne, diquat, 35 disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, églinazine, endothal, épronaz, EPTC, erbon, esprocarb, éthalfluraline, éthamétsulfuron, éthidimuron, éthiolate, éthofumesate, éthoxyfène, éthoxysulfuron, étinofène, etni- promide, étobenzanide, EXD, fénasulame, fénoprop, fénoxaprop, fénoxaprop-P, fénoxasulfone, fentéracol, fenthia- prop, fentrazamide, fénuron, sulfate ferreux, flamprop, flamprop-M, florasulame, fluazifop, fluazifop-P, fluazolate, flucarbazone, flucétosulfuron, fluchloraline, flufénacet, flufénican, flufenpyr, flumétsulame, flumézine, flumiclorac, 40 flumioxazine, flumipropyne, fluométuron, fluorodifène, fluoroglycofène, fluromidine, fluoronitrofène, fluothiuron, flu- poxame, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fluroxypyr, flurtamone, fluthiacet, fomé- safène, formasulfuron, fosamine, furyloxyfène, glufosinate, glufosinate-P, glyphosate, halosafène, halosulfuron, haloxydine, haloxyfop, haloxyfop-P, hexachloracétone, hexaflurate, hexazinone, imazaméthabenz, imazamox, ima- zapic, imazapyr, imazaquine, imazéthapyr, imazosulfuron, indanofan, indaziflame, iodobonil, iodométhane, iodo- 45 sulfuron, iofensulfuron, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamide, isocil, isométhiozine, isonoruron, isopolinate, isopropaline, isoproturon, isouron, isoxabène, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ké- tospiradox, lactofène, lénacile, linuron, MAA, MAMA, MCPA, MCPA-thioéthyl, MCPB, mécoprop, mécoprop-P, mé- dinoterbe, méfénacet, méfluidide, mésoprazine, mésosulfuron, mésotrione, métam, métamifop, métamitrone, mé- tazachlore, métazosulfuron, métflurazone, méthabenzthiazuron, méthalpropaline, méthazole, méthiobencarbe, mé- 50 thiozoline, méthiuron, méthométon, méthoprotryne, bromure de méthyle, isothiocyanate de méthyle, méthyldymron, métobenzuron, métobromuron, métolachlore, métosulame, métoxuron, métribuzine, metsulfuron, molinate, mona- lide, monisouron, acide monochloracétique, monolinuron, monuron, morfamquat, MSMA, naproanilide, napropami- de, naptalame, néburon, nicosulfuron, nipyraclofène, nitralin, nitrofène, nitrofluorfène, norflurazone, noruron, OCH, orbencarb, ortho-dichlorobenzène, orthosulfamuron, oxadiargyl, oxadiazon, oxapyrazone, oxasulfuron, oxaziclo- 55 méfone, oxyfluorfène, parafluron, paraquat, pébulate, acide pélargonique, pendiméthaline, pentachlorophénol, pen- tanochlore, pentoxazone, perfluidone, péthoxamide, phénisophame, phenmédiphame, phendmédiphame-éthyl, phénobenzuron, acétate de phényl-mercure, piclorame, picolinafène, pinoxadène, pipérophos, arsénite de potas- sium, azoture de potassium, cyanate de potassium, prétilachlore, primisulfuron, procyazine, prodiamine, profluazol,

12 EP 2 632 265 B1

profluraline, profoxydime, proglinazine, prométone, prométryne, propachlore, propanil, propaquizafop, propazine, prophame, propisochlore, propoxycarbazone, propyrisulfuron, propyzamide, prosulfaline, prosulfocarb, prosulfuron, proxane, prynachlore, pydanon, pyraclonile, pyraflufène, pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazoxyfène, pyribenzoxime, pyributicarbe, pyriclor, pyridafol, pyridate, pyriftalide, pyriminobac, pyrimisulfan, pyrithiobac, pyroxa- 5 sulfone, pyroxsulame, quinclorac, quinmérac, quinoclamine, quinonamide, quizalofop, quizalofop-P, rhodétanil, rim- sulfuron, saflufénacile, S-métolachlore, sébuthylazine, secbuméton, séthoxydime, siduron, simazine, simétone, si- métryne, SMA, arsénite de sodium, azoture de sodium, chlorate de sodium, sulcotrione, sulfallate, sulfentrazone, sulfométuron, sulfosulfuron, acide sulfurique, sulglycapin, swep, TCA, tébutame, tébuthiuron, téfuryltrione, tembo- trione, tépraloxydime, terbacil, terbucarbe, terbuchlore, terbuméton, terbuthylazine, terbutryne, tétrafluron, thényl- 10 chlore, thiazafluron, thiazopyr, thidiazimine, thidiazuron, thiènecarbazone-méthyl, thifensulfuron, thiobencarbe, tio- carbazil, tioclorime, topramézone, tralkoxydime, tri-allate, triasulfuron, triaziflame, tribénuron, tricamba, triclopyr, tridifane, triétazine, trifloxysulfuron, trifluraline, triflusulfuron, trifop, trifopsime, trioxytriazine, triméturon, tripropi nda- ne, tritac, tritosulfuron, vernolate et xylachlore.

15 8. Procédé conforme à l’une des revendications 4 à 7, dans lequel on lutte contre des végétaux indésirables dans des cultures qui ont été rendues tolérantes ou résistantes aux herbicides du mélange ou à d’autres herbicides, par manipulation génétique ou par mutation et sélection, et de préférence, dans des cultures tolérantes aux inhibiteurs d’acéto-lactate synthétase, ou conjointement avec du 2,4-D, du glyphosate, du glufosinate, du dicamba, des sulfonyl- urées ou des imidazolinones, sur des cultures tolérant le 2,4-D, sur des cultures tolérant le glyphosate, sur des 20 cultures tolérant le glufosinate, sur des cultures tolérant le dicamba, sur des cultures tolérant les sulfonyl-urées, ou sur des cultures tolérant les imidazolinones.

9. Procédé conforme à l’une des revendications 4 à 8, dans lequel le mélange est employé conjointement avec un phytoprotecteur contre herbicide, de préférence choisi dans l’ensemble constitué par les suivants : bénoxacore, 25 benthiocarbe, brassinolide, cloquintocet, cloquintocet-mexyl, cyométrinil, cyprosulfamide, daimuron, dichlormide, dicyclonone, diétholate, dimépipérate, disulfoton, fenchlorazole-éthyl, fenclorime, flurazole, fluxofénime, furilazole, protéines harpines, isoxadifène-éthyl, méfenpyr-diéthyl, méphénate, MG 191, MON 4660, anhydride naphtalique (NA), oxabétrinil, R29148 et N-phényl-amides d’acide sulfonyl-benzoïque.

30 10. Procédé conforme à l’une des revendications 4 à 9, dans lequel le mélange comprend en outre au moins un adjuvant ou véhicule admissible en agriculture.

11. Composition conforme à la revendication 3 ou procédé conforme à la revendication 10, dans lequel le mélange, ou laquelle composition, se présente sous forme de solide, de préférence choisi parmi les poudres fines, granules, 35 granules dispersables dans l’eau et poudres mouillables, ou sous forme de liquide, de préférence choisi parmi les concentrés émulsifiables, solutions, émulsions et suspensions.

12. Composition ou procédé conforme à l’une des revendications 3, 10 et 11, dans laquelle ou lequel les adjuvants sont choisis dans l’ensemble formé par les suivants : concentrés d’huile pour cultures ; éthoxylate de nonyl-phénol ; sel 40 de benzyl-(coco-alkyl)-diméthylammonium quaternaire ; mélange d’hydrocarbure de pétrole, d’esters d’alkyle, d’aci-

de organique et de tensioactif anionique ; (alkyle en C 9-C11)-polyglycoside ; éthoxylate d’alcool phosphaté ; éthoxy- late d’alcool primaire naturel en C 12-C16 ; copolymère à blocs EO-PO de di-sec-butyl-phénol ; polysiloxane à coiffes méthyle ; éthoxylate de nonyl-phénol et urée / nitrate d’ammonium ; huile de graines méthylée et émulsifiée ; éthoxy- late (8 EO) d’alcool tridécylique (synthétique) ; éthoxylate (15 EO) d’amine de suif ; PEG(400)-dioléate-99 ; agents 45 compatibilisants, agents anti-mousse, agents séquestrants, agents de neutralisation et tampons, inhibiteurs de corrosion, colorants, parfums, agents de diffusion, auxiliaires de pénétration, agents d’adhésion, agents dispersants, agents épaississants, agents d’abaissement du point de congélation, et agents antimicrobiens.

13. Composition ou procédé conforme à l’une des revendications 3 et 10 à 12, dans laquelle ou lequel le véhicule liquide 50 est choisi parmi l’eau et les solvants organiques, le solvant organique étant de préférence choisi dans l’ensemble constitué par les fractions pétrolières, hydrocarbures, huiles végétales, esters de ces huiles végétales, esters de monoalcools ou de diols, triols ou autres polyols comportant 4 à 6 groupes hydroxyle, et esters d’acides monocar- boxyliques, dicarboxyliques ou polycarboxyliques ; et mieux encore, choisi dans l’ensemble constitué par les huiles minérales, solvants aromatiques, huiles paraffiniques, huile de soja, huile de colza, huile d’olive, huile de ricin, huile 55 de tournesol, huile de noix de coco, huile de maïs, huile de coton, huile de lin, huile de palme, huile d’arachide, huile de carthame, huile de sésame, huile d’abrasin, stéarate de 2-éthyl-hexyle, oléate de n-butyle, myristate d’iso- propyle, dioléate de propylèneglycol, succinate de dioctyle, adipate de dibutyle, et phtalate de dioctyle ; et surtout, choisi dans l’ensemble constitué par les toluène, xylène, naphta, huile pour cultures, acétone, méthyl-éthyl-cétone,

13 EP 2 632 265 B1

cyclohexanone, trichloroéthylène, perchloroéthylène, acétate d’éthyle, acétate d’amyle, acétate de butyle, éther monométhylique de propylèneglycol, éther monométhylique de diéthylèneglycol, méthanol, éthanol, isopropanol, alcool amylique, éthylèneglycol, propylèneglycol, glycérol, N-méthyl-pyrrolidine-2-one, N,N-diméthyl-alkylamides et diméthylsulfoxyde ; et les fertilisants liquides et les véhicules solides sont choisis dans l’ensemble constitué par les 5 talc, argile pyrophyllite, silice, attapulgite, kaolin, kieselguhr, craie, terre à diatomées, chaux, carbonate de calcium, bentonite, terre de Fuller, coques de graines de coton, farine de froment, farine de soja, pierre ponce, poudre de bois, poudre de coquilles de noix, et lignine.

14. Mélange herbicide synergique, composition ou procédé, conforme à l’une des revendications précédentes, lequel 10 mélange ou laquelle composition, ou dans lequel le mélange ou la composition, comprend en outre un ou plusieurs tensioactif(s) choisi(s) de préférence dans l’ensemble constitué par les suivants : sels alcane-sulfates, sels alkyl- arène-sulfonates, produits d’addition d’oxyde d’alkylène sur alkyl-phénol, produits d’addition d’oxyde d’alkylène sur alcool, savons, sels alkyl-naphtalène-sulfonates, esters dialkyliques de sels sulfo-succinates, esters de sorbitol, amines quaternisées, esters de polyéthylèneglycol et d’acides gras, copolymères à blocs d’oxyde de propylène et 15 d’oxyde d’éthylène, sels d’esters phosphates de monoalkyle ou de dialkyle, huiles végétales ou de graines et esters de ces huiles végétales.

15. Mélange herbicide synergique, composition ou procédé, conforme à l’une des revendications précédentes, lequel mélange ou laquelle composition, ou dans lequel le mélange ou la composition, contient en outre d’autres herbicides, 20 des agents de régulation de la croissance des végétaux, des fongicides, des insecticides, des fertilisants liquides, ou des véhicules fertilisants solides en particules.

25

30

35

40

45

50

55

14 EP 2 632 265 B1

REFERENCES CITED IN THE DESCRIPTION

This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description

• WO 2011094386 A [0003] • WO 2011097187 A [0003] • WO 2011056631 A [0003] • WO 2006086640 A [0003]

Non-patent literature cited in the description

• Herbicide Handbook. Weed Science Society of • Encyclopedia of Surfactants. Chemical Publishing America, 2007, 429 [0003] Co, 1980, vol. I-III [0021] • The Pesticide Manual. 2009 [0006] [0008] • COLBY, S. R. Calculation of the synergistic and an- • McCutcheon’s Detergents and Emulsifiers Annual. tagonistic response of herbicide combinations. MC Publishing Corp, 1998 [0021] Weeds, 1967, vol. 15, 20-22 [0031]

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