US 2011 0065579A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0065579 A1 Sievernich et al. (43) Pub. Date: Mar. 17, 2011

(54) HERBICIDAL COMPOSITION COMPRISING (52) U.S. Cl...... SO4/128 Syrgos TE, GLUFOSINATE OR THEIR (57) ABSTRACT The present invention relates to a herbicidal composition (75) Inventors: Bernd Sievernich, Hassloch (DE); which comprises: William Karl Moberg, Hassloch a) at least one herbicide A selected from glyphosate, glufosi

(DE);DE): Anja Simon, Weinheim- 0 bia nerb1c1de SEE's 3 win1cn 1S 3-lo-(d1Iluoromeunoxy)-1-meunyl 5-(difl thoxy)-1-methyl (DE);( ); HelmutRichard Walter, R. Evans, Obrigheim Raleigh 3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl-4,5-dihyyl)py y y y y NC (US) s s dro-5,5-dimethyl-1,2-oxazole common name: pyroxasul fone. The ppresent invention relates in pparticular to a herbicidal (73) Assignee: BASF SE composition comprising: a) at least one herbicide A selected from glyphosate, glufosi (21) Appl. No.: 12/992,096 nate and their salts, b) a herbicide B which is 3-5-(difluoromethoxy)-1-methyl (22) PCT Filed: May 20, 2009 3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl-4,5-dihy dro-5,5-dimethyl-1,2-oxazole common name: pyroxasul (86). PCT No.: PCT/EP09/56105 fone, and - 0 c) at least one further herbicide C, which is selected from the S371 (c)(1) herbicide groups C.1 to C.8: s C.1 herbicides of the group of acetolactat SVnthase inhibi (2),2). (4) DateDate: Nov.OW. 11,II, 2010 tors (ALS inhibitors),group y O O C.2 herbicides of the group of protoporphyrinogen oxidase Related U.S. Application Data inhibitors (PPO inhibitors), (60) Provisional application No. 61/055,040, filed on May C.3 herbicides of the group of auxines, 21, 2008, provisional application No. 61/056,622, C.4 herbicides of the group of 4-hydroxyphenyl-pyruvate filed on May 28, 2008, provisional application No. dioxygenase inhibitors (HPPD inhibitors), 61/118,895, filed on Dec. 1, 2008. C.5 herbicides of the group of phytoene desaturase inhibi tors (PDS inhibitors), Publication Classification C.6 herbicidesSt. Air of the group off pnotosystemphotosystem 11II 1inhibit 1OS (51) Int. Cl. C.7 herbicides of the group of microtubulin inhibitors, and AOIN 57/20 (2006.01) C.8 herbicides of the group of inhibitors of the synthesis of AOIPI3/00 (2006.01) very long chain fatty acids (VLCFA inhibitors). US 2011/0065579 A1 Mar. 17, 2011

HERBICIDAL COMPOSITION COMPRISING harmful plants, i.e. they should effect damaging of the harm GLYPHOSATE, GLUFOSINATE OR THEIR ful plants more quickly in comparison with application of the SALTS individual herbicides. 0007. These and further objects are achieved by the com positions described hereinafter. 0001. The present invention relates to a herbicidal com 0008. Therefore the present invention relates to a herbi position which comprises at least one herbicide A selected cidal composition comprising: from glyphosate, glufosinate and their salts. The composition 0009 a) at least one herbicide A selected from glyphosate, is particularly useful for preplant burndown. glufosinate and their salts, and 0002 Burndown, i.e. the complete removal of weeds from (0010 b) a herbicide B which is 3-5-(difluoromethoxy)- the Soil by application of herbicides prior to planting or emer 1-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfo gance of a crop, is an important tool of modern weed man nyl-4,5-dihydro-5,5-dimethyl-1,2-oxazole common agement. Weeds present at planting will generally grow much name: pyroxasulfone. quicker than crop plants and thus compete very early in the 0011. It has been proven particular advantageous to com growing season thereby damaging the crop plants and reduc bine the herbicides A and B with at least one further herbicide ing crop yield. Thus, it is desirable to plant the crop in a C, which is selected from weed-free seedbed or to assure that essentially no weeds are 0012 C.1 herbicides of the group of acetolactate synthase present when the crop emerges. inhibitors (ALS inhibitors), 0003 Glyphosate and its salts are non-selective systemic 0013 C.2 herbicides of the group of protoporphyrinogen herbicides having a good post-emergence activity against oxidase inhibitors (PPO inhibitors), numerous grass weeds. So far, glyphosate is one of the most 0014 C.3 herbicides of the group of auxins, commonly used burndown herbicides. Likewise, glufosinate 0015 C.4 herbicides of the group of 4-hydroxyphe and its salts are non-selective systemic herbicides having a nylpyruvate dioxygenase inhibitors (HPPD inhibitors), good post-emergence activity against numerous grass weeds 0016 C.5 herbicides of the group of phytoene desaturase and thus can be used in burndown programs. However, Solo inhibitors (PDS inhibitors), application of glyphosate or glufosinate often yields unsatis 0017 C.6 herbicides of the group of photosystem II inhibi factory weed control, and several applications and/or high tors (PSII inhibitors), dosage rates are often required. Moreover, the effectiveness 0018 C.7 herbicides of the group of microtubulin inhibi of glyphosate and glufosinate against difficult-to-control tors, and broadleaf species (hereinafter broadleaves) and rhizomatous 0019 C.8 herbicides of the group of inhibitors of the syn grasses is poor. Therefore, it is frequently recommended to thesis of very long chain fatty acids (VLCFA inhibitors). apply glyphosate or glufosinate in combination with at least 0020. Therefore, the present invention relates in particular one second herbicide. Such as 2,4-D, dicamba, triazines Such to a herbicidal composition comprising: as atrazine or metribuzin, chloroacetanilides such as meth 0021 a) at least one herbicide A selected from glyphosate, olachloror dimethenamid (including dimethenamid-P), linu glufosinate and their salts, ron and/or pendimethalin. However, the effectiveness of such 0022 b) a herbicide B which is 3-5-(difluoromethoxy)- combinations is often not satisfactory and high application 1-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfo rates are still required to achieve an acceptable control of nyl-4,5-dihydro-5,5-dimethyl-1,2-oxazole common grass weeds and broadleaves. Moreover, the reliability of name: pyroxasulfone, and Such combinations depends strongly on the weathering con 0023 c) at least one further herbicide C, which is selected ditions and certain difficult to control weed species may from the herbicide groups C.1 to C.8 as defined herein. escape. In addition, the herbicidal activity of these composi 0024. The invention furthermore relates to the use of a tions persists only for a short time, which allows effective composition as defined herein for controlling undesirable burndown only within a small timeframe prior to planting a Vegetation. When using the compositions of the invention for crop. Moreover, the persistence of the herbicidal activity this purpose the at least one herbicide A and the herbicide B strongly depends upon the weathering conditions. and optionally C can be applied simultaneously or in Succes 0004 U.S. Pat. No. 6,413.909 suggests a composition Sion, where undesirable vegetation may occur. comprising ametryn, atrazin and paraquat for burndowntreat 0025. The invention furthermore relates to the use of a ment. Paraquat, however is rather toxic to mammals and thus composition as defined herein for controlling undesirable its use is restricted by legal regulations. Vegetation for burndown, i.e. for controlling undesirable veg 0005 US 2005/0256004 discloses a herbicidal composi etation in a locus, e.g. a field, where crops will be planted, tion comprising an isoxazoline derivatives and at least one before planting or emergence of the crop. further herbicide. Neither the combination of glyphosate and 0026. The invention furthermore relates to the use of a pyroxasulfone nor the use of Such compositions in a burn composition as defined herein for controlling undesirable down program have been described therein. Vegetation in crops which, by genetic engineering or by 0006 Thus, it is an object of the present invention to breeding, are resistant to one or more herbicides and/or patho provide a herbicidal composition, which allows efficient and gens Such as plant-pathogenous fungi, and/or to attack by reliable control of grass and broadleaf weeds in a burndown insects; preferably resistant to glyphosate or glufosinate, and program. Moreover, the persistence of the herbicidal activity optionally resistant to the one or more optional herbicides C. of the composition should be sufficiently long in order to 0027. The invention furthermore relates to a method for achieve control of the weeds over a sufficient longtime period controlling undesirable vegetation, which comprises apply thus allowing a more flexible application. The composition ing an herbicidal composition according to the present inven should also have a low toxicity to humans or other mammals. tion to the undesirable vegetation. Application can be done The compositions should also show an accelerated action on before, during and/or after, preferably during and/or after, the US 2011/0065579 A1 Mar. 17, 2011

emergence of the undesirable vegetation. The at least one action of combinations of herbicides A+B against undesirable herbicide A, the herbicide B and the optional at least one Vegetation, in particular against difficult to control species, herbicide C can be applied simultaneously or in Succession. and/or show Superior crop compatibility with certain conven 0028. The invention in particular relates to a method for tional crop plants and with herbicide tolerant crop plants, i.e. controlling undesirable vegetation in crops, which comprises their use in these crops leads to a reduced damage of the crop applying plants and/or does not result in increased damage of the crop 0029 a) at least one herbicide A selected from glyphosate, plants. Apart from that, these compositions may also show an glufosinate and their salts, and optionally accelerated action on harmful plants, i.e. they may effect 0030 b) a herbicide B which is 3-5-(difluoromethoxy)- damage of the harmful plants more quickly in comparison 1-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfo with solo application of the individual herbicides. nyl-4,5-dihydro-5,5-dimethyl-1,2-oxazole, 0036. As used herein, the terms “controlling” and “com 0031 c) one or more herbicides C, selected from the her bating are synonyms. bicides of the groups C.1 to C.8 as defined herein, 0037. As used herein, the terms “undesirable vegetation', to a locus of planted crops where undesirable vegetation “undesirable species”, “undesirable plants”, “harmful occurs or might occur or to a locus where crops will be plants”, “undesirable weeds', or “harmfull weeds' are syn planted before planting or emergence of the crop. onyms. 0032. In the methods of the present invention it is imma 0038 Glyphosate common name of N-(phosphonom terial whether the at least one herbicide A and the herbicide B ethyl)glycine is a well known non-selective systemic herbi and the one or more optional herbicides C are formulated cide, which has been described e.g. in U.S. Pat. No. 3,799,758 jointly or separately and applied jointly or separately, and, in and US 4.4505.531. Glyphosate is commercially available the case of separate application, in which order the applica e.g. from Monsanto under the tradenames RoundupTM and tion takes place. It is only necessary, that the at least one Touchdown.T.M. Glyphosate is also available and marketed in herbicide A and the herbicide B and the one or more optional the form of its agriculturally acceptable salts such as glypho herbicides C are applied in a time frame, which allows simul sate-diammonium 69254-40-6, glyphosate-isopropylam taneous action of the active ingredients on the undesirable monium 38641-94-0, glyphosate-monoammonium plants. 40465-66-5, glyphosate-potassium 70901-20-1, glypho 0033. The invention also relates to an herbicide formula sate-sesquisodium 70393-85-0, glyphosate-trimesium tion, which comprises a herbicidally active composition as 81591-81-3). Preferably, glyphosate is used in the form of its defined herein and at least one carrier material, including monoammonium, diammonium, isopropylammonium or tri liquid and/or Solid carrier materials. mesium salt. 0034. The compositions of the present invention have sev 0039 Glufosinate common name of DL-4-hydroxy eral advantages over Solo application of either glyphosate/ (methyl)phosphinoyl-DL-homoalaninate and its salts such glufosinate or pyroxasulfone. The composition of the present as glufosinate ammonium and its herbicidal acitivity have invention show enhanced herbicide action in comparison been described e.g. by F. Schwerdtle et al. Z. Pflanzenkr. with the herbicide action of solo action glyphosate or pyroxa Pflanzenschutz, 1981, Sonderheft IX, pp. 431-440. Glufosi Sulfone against undesirable vegetation, in particular against nate and its salts are commercially available, e.g. from Bayer difficult to control species such as Alopecurus myosuroides, CropScience under the tradenames BastaTM and LibertyTM. Avena fatua, Bromus spec. Echinocloa spec. Ipomea spec. 0040. 3-5-(Difluoromethoxy)-1-methyl-3-(trifluorom Lolium spec., Phalaris spec. Setaria spec. Digitaria spec. ethyl)pyrazol-4-ylmethylsulfonyl-4,5-dihydro-5,5-dim Brachiaria spec. Amaranthus spec., Chenopodium spec. ethyl-1,2-oxazole common name: pyroxasulfone has been Abutilon theophrasti, Galium aparine, Veronica spec., or described as a preemergent herbicide in EP-A 1364946. Solanum spec. Moreover, the compositions of the invention 0041. In the compositions of the invention the weight ratio show a persistant herbicidal activity, even under difficult of herbicide A to herbicide B is preferably from 2000:1 to weathering conditions, which allows a more flexible applica 1:10, in particular from 500:1 to 1:6 and more preferably from tion in burndown applications and minimizes the risk of 100:1 to 1:2. weeds escaping. The compositions are generally non-toxic or 0042. In the compositions of the invention, wherein at of low toxicity against mammals. Apart form that, the com least one herbicide C is present, the weight ratio of herbicide positions of the present invention show Superior crop com A to herbicide B+C is preferably from 1500:1 to 1:100, in patibility with certain conventional crop plants and with her particular from 1000:1 to 1:50 and more preferably from bicide tolerant crop plants, i.e. their use in these crops leads to 500:1 to 1:2O. a reduced damage of the crop plants and/or does not result in 0043. If the compounds of herbicide compounds men increased damage of the crop plants. Thus, the compositions tioned as herbicides A, herbicides C and safeners D (see of the invention can also be applied after the emergence of the below) have functional groups, which can be ionized, they crop plants. The compositions of the present invention may can also be used in the form of their agriculturally acceptable also show an accelerated action on harmful plants, i.e. they salts. In general, the salts of those cations are Suitable whose may effect damage of the harmful plants more quickly in cations have no adverse effect on the action of the active comparison with solo application of the individual herbi compounds (“agricultural acceptable'). cides. 0044. In general, the salts of those cations are suitable 0035 Although, these advantages may be achieved by whose cations have no adverse effect on the action of the combining glyphosate and/or glufosinate with pyroxasul active compounds (“agricultural acceptable'). Preferred cat fone, it is particularly beneficial to further combine these ions are the ions of the alkali metals, preferably of lithium, herbiccles A and B with at least one further herbicide C of the Sodium and potassium, of the alkaline earth metals, prefer herbicide groups C.1 to C.8. These compositions show ably of calcium and magnesium, and of the transition metals, enhanced herbicide action in comparison with the herbicide preferably of manganese, copper, Zinc and iron, furthermore US 2011/0065579 A1 Mar. 17, 2011

ammonium and Substituted ammonium (hereinafter also ron, halosulfuron, imaZosulfuron, iodosulfuron, mesosulfu termed as organoammonium) in which one to four hydrogen ron, metSulfuron, nicosulfuron, oxasulfuron, primisulfuron atoms are replaced by C-C-alkyl, hydroxy-C-C-alkyl, prosulfuron, pyrazosulfuron, rimsulfuron, Sulfometuron, Sul C-C-alkoxy-C-C-alkyl, hydroxy-C-C-alkoxy-C-C- fosulfuron, thifensulfuron, triasulfuron, tribenuron, triflox alkyl, phenyl or benzyl, preferably ammonium, methylam ysulfuron, triflusulforon and tritosulfuron and the salts, and monium, isopropylammonium, dimethylammonium, diiso esters thereof. propylammonium, trimethylammonium, 0050 Triazolopyrimidine herbicides (C.1.3) include e.g. tetramethylammonium, tetraethylammonium, tetrabutylam cloranSulam-methyl, dicloSulam, floraSulam, flumetSulam, monium, pentylammonium, hexylammonium, heptylammo metoSulam, penoXSulam and pyroxSulam. nium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)eth 0051 Pyrimidinylbenzoate herbicides (C.1.4) include e.g. 1-ylammonium, (diglycolamine salts), di(2-hydroxyeth-1- bispyribac, pyribenzoxim, pyriftalid, pyrithiobac and pyrimi yl)ammonium (diolamine salts), tris(2-hydroxyeth-1-yl) nobac and the salts and esters thereof Such as bispyribac ammonium (trolamine salts), tris(3-propanol)amonium, Sodium, pyrithiobac-Sodium and pyriminobac-methyl. benzyltrimethylammonium, benzyltriethylammonium, fur 0.052 Sulfonylaminocarbonyltriazolinone herbicides thermore phosphonium ions, Sulfonium ions, preferably tri (C.1.5) include e.g. flucarbazone, propxycarbazone and (C-C-alkyl)sulfonium such as trimethylsulfonium, and Sul thiencarbazone, and the salts and esters thereof such as flu foXonium ions, preferably tri(C-C-alkyl)sulfoxonium. carbazone-sodium, propxycarbazone-sodium and thiencar 0045. In the compositions according to the invention, the bazone-methyl. compounds C or D that carry a carboxyl group can also be 0053. In the compositions of this preferred embodiment 1 employed in the form of agriculturally acceptable derivatives, the relative weight ratio of pyroxasulfone to herbicide C.1 is for example as amides such as mono- or di-C-C-alkyla preferably in the range from 1:500 to 500:1, in particular in mides or arylamides, as esters, for example as allyl esters, the range from 1:250 to 250:1 and more preferably from propargyl esters, C-Co-alkyl esters or alkoxyalkyl esters, 100:1 to 1:100. The relative weight ratio of herbicide A to and also as thioesters, for example as C-Co-alkylthioesters. herbicide B+herbicide C.1 is preferably in the range from Preferred mono- and di-C-C-alkylamides are the methyl 1500:1 to 1:20, in particular from 1000:1 to 1:10 and more and the dimethylamides. Preferred arylamides are, for preferably from 500:1 to 1:5. example, the anilidines and the 2-chloroanilides. Preferred 0054 According to a particular preferred embodiment of alkyl esters are, for example, the methyl, ethyl, propyl, iso the invention, the component c) comprises at least one imi propyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl) or dazolinone herbicide (embodiment 1.1). Imidazolinone her isooctyl (2-ethylhexyl) esters. Preferred C-C-alkoxy-C- bicides (group C.1.1) are known e.g. from Shaner, D. L. C-alkyl esters are the straight-chain or branched C-C- O'Conner, S. L. The Imidazolinone Herbicides, CRC Press alkoxyethyl esters, for example the methoxyethyl, ethoxy Inc., Boca Raton, Fla. 1991 and also from The Compendium ethyl or butoxyethyl esters. An example of the straight-chain of Pesticide Common Names http://www.alanwood.net/pes or branched C-Co-alkyl thioesters is the ethyl thioester. ticides/. Preferred derivatives are the esters. 0055 Imidazolinone herbicides include imazamethabenz, 0046 According to a first preferred embodiment of the imaZamox, imazapic, imazapyr, imaZaquin and imaZethapyr. invention (embodiment 1), the herbicidal compositions of the their salts, in particular their sodium salts, potassium salts, invention additionally comprise at least one further herbicide ammonium salts or substituted ammonium salts as defined C selected from the group of acetolactate synthase inhibitors, above, in particular mono-, diand tri-C-C-alkylammonium also termed as ALS inhibitors (also termed AHAS inhibitors salts such as isopropylammonium salts and their esters, in or inhibitors of acetohydroxy acid synthase). ALS inhibitors particular their C-C-alkyl esters, such as methylesters, are compounds, which have a mode of action comprising the ethylesters, iso propyl esters. Suitable examples of such salts inhibition of a step of the branched chain amino acids bio include imaZamoX-ammonium, imazapic-ammonium, synthesis in plants and which belong to the group B of the imazapyr-isopropylammonium, imaZaquin-ammonium, HRAC classification system (see HRAC, Classification of imaZaquin-sodium and imazethapyr-ammonium. Suitable Herbicides According to Mode of Action, http://www.plant examples of such esters include imazamethabenZ-methyl and protection.org/hrac/MOA.html). imaZaquin-methyl. 0047 According to the present invention the ALS inhibi 0056 Preferred imidazolinone herbicides include tor is preferably selected from the group consisting of imaZamox, imaZapic, imazapyr, imaZaquin, imaZethapyr. their salts and their esters, as well as mixtures thereof, in particular imaZamox, imazapic, imazapyr and imazethapyr, C.1.1 imidazolinone herbicides; their salts and their esters, as well as mixtures thereof, in C.1.2 Sulfonylurea herbicides; particular mixtures of imaZamox with imazapyr and/or C.13 triazolopyrimidine herbicides; imazethapyr and mixtures of imazapic with imazapyr and/or C.1.4 pyrimidinylbenzoate herbicides; and imazethapyr. C.1.5 Sulfonylaminocarbonyltriazolinone herbicides. 0057 The imidazolinones may be present in the form of their racemate or in the form of the pure R- or S-enantiomers 0048. Imidazolinone herbicides (C.1.1) include e.g. (including salts and esters as defined above). Very suitable imazapic, imazamethabenZ-methyl, imaZamox, imazapyr, Imidazolinones are the R-isomers, e.g. R-imazamethabenz imaZaquin, and imazethapyr and the salts thereof. methyl, R-imaZamox, R-imazapic, R-imazapyr, R-imaza 0049 Sulfonylurea herbicides (C.1.2) include e.g. ami quin, R-imazethapyr, in particular R-imaZamoX. These com dosulfuron, azim Sulfuron, benSulfuron, chlorimuron, chlor pounds are known e.g. from U.S. Pat. No. 5,973,154 B Sulfuron, cinosulfuron, cycloSulfamuron, ethametSulfuron, (American Cyanamid Company) and U.S. Pat. No. 6,339,158 ethoxysulfuron, flazasulfuron, flupyrsulfuron, foramsulfu B1 (American Cyanamid Company). US 2011/0065579 A1 Mar. 17, 2011

0058. In particular preferred compositions of the embodi ment 1.1, the herbicide C comprises or in particular is imaZamoX or a salt thereof such as imaZamox-ammonium. (C.2.1) 0059. In other particular preferred compositions of the R2 O embodiment 1.1, the herbicide C comprises or in particular is imazapic or a salt thereof Such as imazapic-ammonium. 0060. In further particular preferred compositions of the R4 N \ CF embodiment 1.1, the herbicide C comprises or in particular is N imazapyr or a salt thereof Such as imazapyr-ammonium or R1 R3 O) VR5 imazapyr-isopropylammonium. 0061. In further particular preferred compositions of the embodiment 1.1, the herbicide C comprises or in particular is (0071 wherein imazethapyr or a salt thereof Such as imazethapyr-ammo 0072 R is selected from the group consisting of the nium. radicals propargyloxy, allyloxy, isopropyloxy, C(=O) 0062. In further particular preferred compositions of the NHSONR'R'', C(=O)N NR'R'', embodiment 1.1, the herbicide C comprises or in particular is O CR'R' C(=O) OR', C(=O)C imaZaquin or a salt or ester thereof such as imaZaquin-ammo CR'R' C(=O) OR, C(=O)C R', C(=O) nium, imazaquin-sodium or imaZaquin-methyl. O CHR C(=O)NHSONR'R'', 0063. In further particular preferred compositions of the NHSONR'R'', SONHC(=O)NR'R'', CH, CH embodiment 1.1, the herbicide C comprises or in particular is (Cl)CO R'' and the radical of the formula OC(CH) a mixture of imaZamox and imazethapyr or salts thereof. C(=O) OR'; where 0064. In further particular preferred compositions of the 0073 R' is hydrogen or C-C-alkyl: embodiment 1.1, the herbicide C comprises or in particular is 10074) R' is C-C-alkyl; a mixture of imazapic and imazethapyr or salts thereof. 0075) R' is hydrogen or C-C-alkyl: 0065. In further particular preferred compositions of this (0076) R' is hydrogen or C-C-alkylor a agricultur embodiment 1.1, the herbicide C comprises or in particular is ally acceptable cation; and Rte is C-C-alkyl, prop a mixture of imaZamox and imazapyr or salts thereof. argyl or allyl, 0066. In a further particular preferred compositions of the 0.077 R’ is hydrogen, fluorine or chlorine; embodiment 1.1, the herbicide C comprises or in particular is 0078 R is hydrogen ortogether with R' forms amoiety a mixture of imazapic and imazapyr or salts thereof. - O C(R)=N or N=C(R) NH 0067. In the embodiment 1.1 the relative weight ratio of (0079 where RandR are selected, independently pyroxasulfone and imidazolinone herbicide is preferably of each other, from hydrogen, C-C-alkyl, C-C- from 1:500 to 500:1, in particular in the range from 1:250 to haloalkyl, C-C-alkenyl, C-C-haloalkenyl, C-C- 250:1 and more preferably from 100:1 to 1:100. The relative alkylnyl, C-C-haloalkylnyl, C-C-alkoxy, C-C- weight ratio of herbicide A to herbicide B+herbicide C.1.1 is cycloalkyl and C-C-alkyl substituted by a C-C- preferably in the range from 1500:1 to 1:20, in particular from cycloalkyl radical; with RandR preferably being 1000:1 to 1:10 and more preferably from 500:1 to 1:5. selected, independently of each other, from C-C- 0068 According to a second preferred embodiment of the alkyl, C-C-haloalkyl, and C-C2-alkyl Substituted invention (embodiment 2), the herbicidal compositions of the by a C-C-cycloalkyl radical with R" and R more invention additionally comprise at least one further herbicide preferably being selected, independently of each C.2 which is an inhibitor of protoporphyrinogen-IX-oxidase other, from methyl, ethyl, n-propyl, isoprobly, n-bu (PPO inhibitor). PPO inhibitors are compounds, which have a tyl, 2-methylpropyl, trifluoromethyl and cyclopropy mode of action comprising the inhibition of a step of the lmethyl; chlorophyll biosynthesis in plants and which belong to the 0080) R' is halogen or cyano, in particular chlorine or group E of the HRAC classification system (see HRAC, Clas fluorine; and sification of Herbicides According to Mode of Action, http:// I0081) R' is selected from hydrogen amino, methyl or www.plantprotection.org/hrac/MOA.html). propargyl and wherein R is preferably methyl. 0069. According to the present invention the PPO inhibi I0082. The organic moieties mentioned in the above defi tor of the group C.2 is preferably selected from the group nitions of the variables are—like the term halogen—collec consisting of: tive terms for individual listings of the individual group mem bers. The prefix C-C, indicates in each case the possible number of carbon atoms in the group. I0083. The term halogen denotes in each case fluorine, C.2.1 phenyluracil herbicides; bromine, chlorine or iodine, in particular fluorine, chlorine or C.2.2 dicarboximide herbicides: bromine. C.23 triazolone and oxadiazolone herbicides; C.2.4 nitrophenylether herbicides; I0084. The term “alkyl as used herein denotes in each case C.2.5 pyrazole herbicides; a straight-chain or branched alkyl group having usually from C.26 triazindione herbicides; and 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, C.2.7 dicarboxamide herbicides. more preferably from 1 to 3 carbon atoms. Examples of an alkyl group are methyl, ethyl, n-propyl, iso-propyl. n-butyl, 0070 Phenyluracil herbicides, which are also termed as 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-me pyrimidinedioneherbicides (group C.2.1) include benzfendi thylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, Zone and compounds of the formula C.2.1 and the salts n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methyl thereof, pentyl, 2-methylpenty1.3-methylpentyl, 4-methylpentyl, 1.1- US 2011/0065579 A1 Mar. 17, 2011 dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2.2- preferably from 3 to 4 carbon atoms, wherein the hydrogen dimethylbutyl, 2,3-dimethylbutyl, 3.3-dimethylbutyl, atoms of this group are partially or totally replaced with 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1.2.2-trim halogen atoms. ethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methyl 0093. The term “alkyl substituted by analkoxy radical as propyl. used herein refers to linear or branched alkyl having usually 1 0085. The term “haloalkyl as used herein denotes in each to 4 carbonatoms, wherein 1 of those carbonatoms carries an case a straight-chain or branched alkyl group having usually alkoxy radical usually having 1 to 4 carbon atoms. Examples from 1 to 6 carbon atoms, preferably from 1 to 4 carbon are CHOCH, CH, OCHs, n-propoxymethyl, CH atoms, wherein the hydrogenatoms of this group are partially OCH(CH), n-butoxymethyl, (1-methylpropoxy)-methyl, or totally replaced with halogen atoms. Preferred haloalkyl (2-methylpropoxy)methyl, CH2—OC(CH), 2-(methoxy) moieties are selected from C-C-haloalkyl, more preferably ethyl, 2-(ethoxy)ethyl 2-(n-propoxy)-ethyl, 2-(1-methyl from C-C-haloalkyl, in particular from C-C-fluoroalkyl ethoxy)-ethyl, 2-(n-butoxy)ethyl 2-(1-methylpropoxy)- such as fluoromethyl, difluoromethyl, trifluoromethyl, ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1,1-dimethylethoxy)- 1-fluoroethyl 2-fluoroethyl, 2,2-difluoroethyl, 2.2.2-trifluo ethyl, 2-(methoxy)-propyl. 2-(ethoxy)-propyl, 2-(n- roethyl, pentafluoroethyl and the like. propoxy)-propyl. 2-(1-methylethoxy)-propyl. 2-(n-butoxy)- I0086. The term “alkoxy” as used herein denotes in each propyl. 2-(1-methylpropoxy)-propyl, 2-(2-methylpropoxy)- case a straight-chain or branched alkyl group which is bound propyl. 2-(1,1-dimethylethoxy)-propyl, 3-(methoxy)-propyl. via an oxygenatomat any position in the alkyl group and has 3-(ethoxy)-propyl, 3-(n-propoxy)-propyl, 3-(1-methyl usually from 1 to 6 carbon atoms, preferably 1 to 4 carbon ethoxy)-propyl, 3-(n-butoxy)-propyl, 3-(1-methylpropoxy)- atoms. Examples of an alkoxy group are methoxy, ethoxy, propyl, 3-(2-methyl propoxy)-propyl, 3-(1,1-dimethyl n-propoxy, iso-propoxy, n-butyloxy, 2-butyloxy, iso-buty ethoxy)-propyl. 2-(methoxy)-butyl, 2-(ethoxy)-butyl, 2-(n- loxy, tert.-butyloxy and the like. propoxy)-butyl, 2-(1-methylethoxy)-butyl, 2-(n-butoxy)- 0087. The term “haloalkoxy” as used herein denotes in butyl, 2-(1-methylpropoxy)-butyl, 2-(2-methyl-propoxy)- each case a straight-chain or branched alkoxy group having butyl, 2-(1,1-dimethylethoxy)-butyl, 3-(methoxy)-butyl, from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, 3-(ethoxy)-butyl, 3-(n-propoxy)-butyl, 3-(1-methylethoxy)- wherein the hydrogen atoms of this group are partially or butyl, 3-(n-butoxy)-butyl, 3-(1-methylpropoxy)-butyl, 3-(2- totally replaced with halogen atoms, in particular fluorine methylpropoxy)-butyl, 3-(1,1-dimethylethoxy)-butyl, atoms. Preferred haloalkoxy moieties include C-C-ha 4-(methoxy)-butyl, 4-(ethoxy)-butyl, 4-(n-propoxy)-butyl, loalkoxy, in particular C-C-fluoroalkoxy, such as fluo 4-(1-methylethoxy)-butyl, 4-(n-butoxy)-butyl, 4-(1-methyl romethoxy, difluoromethoxy, trifluoromethoxy, 1-fluoroet propoxy)-butyl, 4-(2-methylpropoxy)-butyl, 4-(1,1-dimeth hoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2.2.2- ylethoxy)-butyl and the like. trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- 0094. The term “alkyl substituted by cycloalkyl radical as difluoro-ethoxy, 2,2-dichloro-2-fluorethoxy, 2.2.2- used herein refers to linear or branched alkyl having usually 1 trichloroethoxy, pentafluoroethoxy and the like. to 2 carbon atoms, wherein 1 of those carbon atoms carries a 0088. The term “cycloalkyl as used herein and in the cycloalkyl radical usually having 3 to 6 carbon atoms. cycloalkyl moieties of cycloalkyl-alkyl denotes in each case a Examples are CH-cylcopropyl (cyclopropylmethyl), CH monocyclic Saturated carbocyclic radical having usually cylcobutyl (cyclobutylmethyl), CH-cylcopentyl (cyclo from 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, pentylmethyl), CH-cylcohexyl (cyclohexylmethyl), cyclopenty1 and cyclohexyl. CHCH-cylcopropyl (2-cyclopropylethyl), CHCH-cyl cobutyl (2-cyclobutylethyl), CHCH-cylcopentyl (=2-cy 0089. The term “alkenyl' as used herein denotes in each clopentylethyl), CHCH-cylcohexyl (2-cyclohexylethyl), case a singly unsaturated hydrocarbon radical having usually CH(CH)-cylcopropyl (=1-cyclopropylethyl), CH(CH)-cyl 3 to 6, or preferably 3 to 4 carbon atoms, such as vinyl, allyl cobutyl (=1-cyclobutylethyl), CH(CH)-cylcopentyl (=1-cy (2-propen-1-yl), 1-propen-1-yl, 2-propen-2-yl, methallyl clopentylethyl) or CH(CH)-cylcohexyl (=1-cyclohexyl (2-methylprop-2-en-1-yl), ethyl). 2-buten-1-yl, 3-buten-1-yl, 2-penten-1-yl, 3-penten-1-yl, 0.095 According to a preferred embodiment of the inven 4-penten-1-yl, 1-methylbut-2-en-1-yl, 2-ethylprop-2-en-1-yl tion, the phenyluracil herbicides (group C.2.1) are selected and the like. from benzfendizone and compounds of the formula C.2.1a 0090 The term “haloalkenyl as used herein denotes in and the salts thereof, each case a straight-chain or branched alkenyl group, as defined above, having usually from 3 to 6 carbon atoms, preferably from 3 to 4 carbon atoms, wherein the hydrogen (C.2.1a) atoms of this group are partially or totally replaced with halogen atoms. 0091. The term “alkynyl as used herein denotes in each case a singly unsaturated hydrocarbon radical having usually from 3 to 6 carbon atoms, such as ethynyl, propargyl (2-pro pyn-1-yl), 1-propyn-1-yl, 1-methylprop-2-yn-1-yl), 2-butyn 1-y1,3-butyn-1-yl, 1-pentyn-1-yl, 3-pentyn-1-yl 4-pentyn-1- yl, 1-methylbut-2-yn-1-yl, 1-ethylprop-2-yn-1-yl and the like. wherein 0092. The term “haloalkynyl as used herein denotes in 0.096 R" is selected from the group consisting of the radi each case a straight-chain or branched alkynyl group, as cals propargyloxy, allyloxy, isopropyloxy, C(=O) defined above, having usually from 3 to 6 carbon atoms, NHSONR'R'', C(=O)N NRiaR', C(=O)C US 2011/0065579 A1 Mar. 17, 2011

CR'R' C(=O) OR, C(=O)C R', C(=O)C 0114 R is chlorine, R is chlorine, R is methyland R' CHR C(=O)NHSONR'R'', NHSONR'R'', is ethyl, SONHC(=O)NR'R'', CH, CH(CI)CO R'' and 0115 R is fluorine, R is chlorine, R is methyland R' the radical of the formula OC(CH), C(=O) OR': is trifluoromethyl or where 0116 R is chlorine, R is chlorine, R is methyland R' 0097) R' is hydrogen or C-C-alkyl: is trifluoromethyl. 0098) R' is C-C-alkyl: 0117. An especially preferred compound of this embodi 0099 R' is hydrogen or C-C-alkyl: ment is a compound of the formula C.2.1b, wherein R is (0.100) R' is hydrogen or C-C-alkylora agriculturally fluorine, R is chlorine, R is methyl and R is cyclopropyl acceptable cation; and methyl. 10101) R' is C-C-alkyl, propargyl orallyl; and 0118. According to another preferred embodiment of the 0102 R is hydrogen, fluorine or chlorine. invention the phenyluracil herbicides (group C.2.1) are 0103 Examples of particularly preferred compounds of selected from compounds of the formula C.2.1c and the salts formula C.2.1a include thereof, 01.04 butafenacil (R'=C(=O)C) C(CH), C (=O) OCH-CH=CH R–H), (C.2.1c) 0105 flupropacil (R'=C(=O)C)-CH(CH), R2 O R’—H), and 0106 saflufenacil (R'—C(=O)NHSON(CH)(CH (CH)), R°—F), R4 N \ CF with a particular preference given to saflufenacil. N 0107 According to another preferred embodiment of the V 5 invention the phenyluracil herbicides (group C.2.1) are HN 2N O R selected from compounds of the formula C.2.1b and the salts thereof, R3b

(C.2.1b) wherein R. R. RandR areas defined herein, and wherein R2 O R. R. R. and R, independently of each other, and more preferably in combination have one of the following mean ings R4 N \ CF R’ is preferably fluorine or chlorine, R" is preferably chlorine, ) N R is preferably methyl and N N O O R5 R is preferably selected from C-C-alkyl, C-C-haloalkyl, and C-C2-alkyl Substituted by a C-C-cycloalkyl radical with R" being more preferably selected from methyl, ethyl, andE. cyclopropylmethyl. E. buyl. 2-methylpropyl, trifluoromethyl wherein R. R. RandR areas defined herein, and wherein 0119 Examples of particularly preferred compounds of R. R. R. and R, independently of each other, and more t S. a sell from the group of compounds of preferably in combination have one of the following mean the formula C.2.1c, wherein ings 0120 R is fluorine, R is chlorine, R is methyland R' R’ is preferably fluorine or chlorine, is cyclopropylmethyl, R" is preferably chlorine, 0121 R is chlorine, R is chlorine, R is methylandR R is preferably methyl and is cyclopropylmethyl, R" is preferably selected from C-C-alkyl, C-C-haloalkyl, I0122) R' is fluorine, R is chlorine, R is methylandR and C-C2-alkyl Substituted by a C-C-cycloalkyl radical is methyl, with R" being more preferably selected from methyl, ethyl, (0123 R’ is chlorine, Rischlorine, R is methylandR n-propyl, isoprobly, n-butyl, 2-methylpropyl, trifluoromethyl is methyl, and cyclopropylmethyl. (0.124 R is fluorine, R is chlorine, R is methylandR 0108 Examples of particularly preferred compounds of is ethyl, formula C.2.1b are selected from the group of compounds of 0.125 R is chlorine, R is chlorine, R is methylandR the formula C.2.1 b, wherein is ethyl, 0109 R is fluorine, R is chlorine, R is methyland R' 0.126 R is fluorine, R is chlorine, R is methyland R' is cyclopropylmethyl, is trifluoromethyl or 0110 R is chlorine, R is chlorine, R is methyland R' I0127 R’ is chlorine, Rischlorine, R is methylandR is cyclopropylmethyl, is trifluoromethyl. 0111 R is fluorine, R is chlorine, R is methyland R' I0128. An especially preferred compound is a compound of is methyl, the formula C.2.1c, wherein R is fluorine, R is chlorine, R 0112 R is chlorine, R is chlorine, R is methyland R' is methyl and R is trifluoromethyl. is methyl, I0129. Phenyluracil herbicides herbicides (group C.2.1) 0113 R’ is fluorine, R is chlorine, R is methyland R' are known from e.g. G. Theodoridis “Protoporphyrinogen is ethyl, IX-oxidase Inhibitors’ in “Modern Crop Protection Com US 2011/0065579 A1 Mar. 17, 2011 pounds' Vol. 1, Wiley-VHC 2007, pp 153-186: C. D. S. 0141 R is fluorine or chlorine; Tomlin, “The Pesticide Manual”, 13th Edition, BCPC (2003), 0142) R' is CH, tert-butyl: and also from The Compendium of Pesticide Common 0.143 R'' is CHF, or together with R' may for 1,4- Names http://www.alanwood.net/pesticides/. butandiyl: 0130 Dicarboximide herbicides (C.2.2) include com I0144) R' is hydrogen, C-C-alkyl or a agriculturally pounds of the formula C.2.2, acceptable cation. 0145 Examples of the compounds of formula C.2.3 include azafenidin, carfentraZone, SulfentraZone, oxadiaZon (C.2.2) and oxadiargyl. Also included are the salts of carfentraZone, R13 O in particularits sodium salt, potassium salt, ammonium salt or Substituted ammonium salts as defined above, in particular mono-, diand tri-C-C-alkylammonium salts such as isopro R15 N pylammonium salts and the esters of carfentraZone, in par ticular its C-C-alkyl esters, such as methylesters, ethylest R 14 O ers, isopropyl esters. A Suitable example of Such an ester is carfentraZone-ethyl. wherein 0146 Triazolone and oxadiazolone herbicides (group C.2. 0131) R' is hydrogen, fluorine or chlorine; 3) are known from e.g. G. Theodoridis “Protoporphyrinogen (0132) R'' is selected from the group consisting of propar IX-oxidase Inhibitors’ in “Modern Crop Protection Com gyloxy, allyloxy, 1-methyl-2-propinyloxy, O—CH2CO pounds” Vol. 1, Wiley-VHC 2007, pp 153-186: C. D. S. R", CH=C(Cl)CO R'' and isopropyloxy: Tomlin, “The Pesticide Manual”, 13th Edition, BCPC (2003), 0133) R' is fluorine or chlorine; or and also from The Compendium of Pesticide Common 0134) R'' and R' together form a moiety O CH-C Names http://www.alanwood.net/pesticides/. (=O) NR'', where R'' is a propargyl radical and where 0147 Nitrophenylether herbicides (C.2.4) include fury the oxygenatom is meta with regard to the position of R: loxyphen and compounds of the formula C.2.4. I0135) R' is hydrogen, C-C-alkyl or an agriculturally acceptable cation. 0.136 Examples of compounds of formula C.2.2 include (C.2.4) cinidon, flumioxazin, flumiclorac and flumipropyn. Also C R19 included are the salts ofcinidon and flumiclorac, in particular their sodium salts, potassium salts, ammonium salts or Sub R18 O NO stituted ammonium salts as defined above, in particular mono-, diand tri-C-C-alkylammonium salts such as isopro pylammonium salts, and the esters of cinidon and flumiclo R20 rac, in particular their C-C-alkyl esters, such as methylest ers, ethylesters, isopropyl esters. Suitable examples of Such wherein esters are cinidon-ethyl and flumiclorac-pentyl. 0148) R' is chlorine or trifluoromethyl:y 0.137 Dicarboximide herbicides (group C.2.2) are known 0149 R' is selected from the group consisting9. of hydroy from e.g. G. Theodoridis “Protoporphyrinogen-IX-oxidase gen, C-C-alkoxy, Inhibitors' in “Modern Crop Protection Compounds' Vol. 1, Wiley-VHC 2007, pp 153-186: C. D. S. Tomlin, “The Pesti O150 CO. R', C(=O)C CH-CO, R', C(=O) cide Manual, 13th Edition, BCPC (2003), and also from The O CH(CH)CO, R2, C(=O)NH SO, R’’: Compendium of Pesticide Common Names http://www.alan 0151) R' is hydrogen, fluorine or chlorine; wood.net/pesticides/. I0152 R is hydrogen, C-C-alkyl or a agriculturally 0138 Triazolone and oxadiazolone herbicides (C.2.3) acceptable cation; and include in particular compounds of the formula C.2.3 and 0153 R’ is C-C-alkyl. their salts, 0154 Examples of compounds of formula C.2.4 include nitrofen, bifenox, oxyfluorfen, acifluorfen, fluoroglycofen, fluorodifen, fomesafen, lactofen, halosafen, chlornitrofen, (C.2.3) fluornitrofen, chlomethoxyfen and nitrofluorfen and their salts and esters. In particular included are the salts of acifluo rfen and fluoroglycofen, in particular the sodium salts, potas sium salts, ammonium salts or Substituted ammonium salts as defined above, in particular mono-, diand tri-C-C-alkylam monium salts such as isopropylammonium salts and the R10 esters of acifluorfen and fluoroglycofen, in particular their R8 C-Cs-alkyl esters, such as methylesters, ethylesters, isopro pyl esters. A Suitable example of Such a salt is acifluorfen wherein sodium. Suitable examples of such esters are acifluorfen 0139 X is O or NR'', methyl and fluoroglycofen-ethyl. I0140 R is selected from the group consisting of propar 0155 Nitrophenylether herbicides (group C.2.4) are gyloxy, allyloxy, isopropyloxy, the radical of the formula known from e.g. G. Theodoridis “Protoporphyrinogen-IX CH-CH(CI)CO R'' and the radical of the formula oxidase Inhibitors' in “Modern Crop Protection Compounds NH SO CHs: Vol. 1, Wiley-VHC 2007, pp 153-186: C. D. S. Tomlin, “The US 2011/0065579 A1 Mar. 17, 2011

Pesticide Manual, 13th Edition, BCPC (2003), and also from 0163 According to a further preferred embodiment of the The Compendium of Pesticide Common Names http://www. invention, the pyrazole type herbicides (group C.2.5) are alanwood.net/pesticides/. selected from compounds of the formula C.2.5b and the salts 0156 Pyrazole type herbicides (group C.2.5) include thereof, compounds of the formula C.2.5 and the salts thereof,

(C.2.5b) (C.2.5)

RI

wherein (0164) R' is selected from the group consisting of the radi wherein R', R, R and Rare as defined for formula C.2.1 cals propargyloxy, allyloxy, isopropyloxy, C(=O) and wherein NHSONR'R'b,C(O)N NR'R'', O CR'R's C R is selected from difluoromethoxy, trifluoromethyl and (—O) OR, C(=O)C CR'R' C(=O) OR'e, methylsulfonyl: C(=O)C R', C(=O)C CHR C(=O) R’ is selected from halogen or methyl, in particular from NHSONR'R'', NHSONR'R'', SONHC(=O) chlorine or bromine. NR'R'', CH, CH(CI)CO, R'' and the radical of the 0157 According to another preferred embodiment of the formula OC(CH), C(=O) OR'; where invention the pyrazole type herbicides (group C.2.5) are (0165) R' is hydrogen or C-C-alkyl: selected from compounds of the formula C.2.5a and the salts (0166 R' is C-C-alkyl: thereof, (0167) R' is hydrogen or C-C-alkyl: (0168) R' is hydrogen or C-C-alkyl or a agriculturally acceptable cation; and

(C.2.5a) (0169) R' is C-C-alkyl, propargyl or allyl: (0170 R is hydrogen, fluorine or chlorine; (0171) R' is selected from difluoromethoxy, trifluorom ethyl and methylsulfonyl; and (0172 R is selected from halogen or methyl, in particular from chlorine or bromine. 0173 Examples of particularly preferred compounds of formula C.2.5b include 0.174 fluazolate (R'=C(=O)C CH(CH), R—F, R=trifluoromethyl, R'-bromine), and (0175 pyraflufen-ethyl (R'—O CH C(=O)C)— wherein R. R. R. R. and R7 are as defined herein, and CHCH, R—F, R=difluoromethoxy, R7-chlorine). wherein R, R, R, R and 0176 Triazinedione type herbicides (group C.2.6) include R", independently of each other, and more preferably in com e.g. compounds of the formula C.2.6 and the salts thereof, bination have one of the following meanings R’ is preferably fluorine or chlorine, (C.2.6) R" is preferably chlorine, R23 O R25 R is preferably difluoromethoxy, / R’ is preferably chlorine or bromine and N R" is preferably selected from C-C-alkyl, C-C-haloalkyl, O N X=Y and C-C2-alkyl Substituted by a C-C-cycloalkyl radical y-NV with R" being more preferably selected from methyl, ethyl, N O R26 n-propyl, isoprobly, n-butyl, 2-methylpropyl, trifluoromethyl V and cyclopropylmethyl. O R24 0158 Examples of particularly preferred compounds of formula C.2.5 are selected from the group of compounds of wherein the formula C.2.5a, wherein (0177 R’ is hydrogen, fluorine or chlorine; 0159 R is fluorine, R is chlorine, R is methyl, R is (0178) R' is selected from hydrogen, C-C-alkyl, C-C- difluoromethoxy, R is chlorine and R is ethyl, haloalkyl, C-C-alkenyl, C-C-haloalkenyl, C-C-alky (0160 R is chlorine, R is chlorine, R is methyl, R is nyl, C-C-haloalkynyl, C-C-alkoxy, C-C-cycloalkyl difluoromethoxy, R is chlorine and R is ethyl, and C-C2-alkyl Substituted by a C-C-cycloalkyl radical; (0161 R is fluorine, R is chlorine, R is methyl, R is (0179 R is selected from hydrogen, amino, methyl and difluoromethoxy, R is bromine and R' is ethyl, or propargyl; (0162 R is chlorine, R is chlorine, R is methyl, R is 0180 R is selected from hydrogen and methyl: difluoromethoxy, R is bromine and R is ethyl. and Y is O or S. US 2011/0065579 A1 Mar. 17, 2011

0181 Preference is given to compounds of the formula (0195I R is selected from halogen and C-C-alkyl, in C.2.6, wherein Y. R. R. R. and R, independently of particular methyl; each other, and more preferably in combination have one of (0196) R’ is selected from halogen, C-C-alkyl and a the following meanings: radical COR', it being possible for n=2 or 3 that the radicals R are identical or different from each other; Y is S, (0197) R is C-C-alkyl. 0182 R is preferably fluorine or chlorine, 0198 A particular preferred compound of the formula R is preferably C-C-alkyl, C-C-alkenyl, or C-C-alky C.2.7 is the compound of the following formula C.2.7a: nyl, in particular C-C-alkynyl, and especially propargyl. R’ is preferably methyl, and (C.2.7a) R’ is preferably methyl. H3C 0183 In a particular preferred compound of the formula C.2.6 the variable Y is S, R is fluorine, R is propargyl, R is methyl and R is methyl. 0184 Dicarboxamide type herbicides (group C.2.7) include e.g. compounds of the formula C.2.7 and the salts thereof,

(C.2.7) 21 + (R), 1S Preferred PPO inhibitors include 0199 pyrimidinedione herbicides (also termed as phe N O nyluracil herbicides), in particular benzfendizone and (R28,-- compounds of the formula C.2.1a Such as butafenacil, 21 O flupropacil and saflufenacil, 0200 triazolinones such as azafenidin, carfentraZone and the salts and esters thereof Such as carfentraZone HNN R27 ethyl and SulfentraZone, 0201 oxadiazoles Such as oxadiazon and oxadiargyl, wherein 0202 thiadiazoles such as fluthiazet and thidiazimin, 0185 m is 0, 1, 2, or 3, in particular 1 or 2: 0203 N-phenylphthalimide herbicides (also termed as 0186 n is 0, 1, 2, 3 or 4, in particular 1 or 2: dicarboximide herbicides) Such as cinidon, flumioxazin, 0187 R’ is selected from C-C-alkyl, C-Ca-haloalkyl, flumiclorac, and flumipropyn, C-C-alkenyl, C-C-haloalkenyl, C-C-alkylnyl, 0204 nitrobiphenylethers such as nitrofen, bifenox, C-C-haloalkylnyl, C-C-cycloalkyl, C-C-alkyl Sub oxyfluorfen, acifluorfen, fluoroglycofen, fluorodifen, stituted by a C-C-alkoxy radical, and C-C-alkyl Sub fomesafen, lactofen, halosafen, chlornitrofen, fluorni stituted by a C-C-cycloalkyl radical; trofen, chlomethoxyfen and nitrofluorfen and the salts 0188 R is selected from halogen, C-C-alkyl, C-C- and esters of the aforementioned compounds. haloalkyl, C-C-alkoxy, and C-C-alkyl Substituted by a Preferred PPO inhibitors also include C-C-alkoxy radical, it being possible for m=2 or 3 that 0205 pyrimidinedioneherbicides of the formulae C.2.1 the radicals R are identical or different from each other, b and C.2.1c, in particular compounds of the formula (0189 R’ is selected from halogen, cyano, nitro, C-C- C.2.1b, wherein alkyl, C-C-haloalkyl, C-C-alkylsulfonyl, C-C- 0206 R is fluorine, R is chlorine, R is methyl and alkoxy, C-C-alkyl Substituted by a C-C-alkoxy radical, R" is cyclopropylmethyl, C-C2-alkyl Substituted by a C-C-cycloalkyl radical and 0207 R’ is chlorine, R is chlorine, R is methyl and a radical COR', it being possible for n=2, 3 or 4 that the R" is cyclopropylmethyl, radicals Rare identical or different from each other; (0208 R is fluorine, R is chlorine, R is methyl and (0190I R' is selected from C-C-alkyl, C-C-haloalkyl, R" is methyl, C-C-alkenyl, C-C-haloalkenyl, C-C-alkylnyl, (0209 R is chlorine, R is chlorine, R is methyl and C-C-haloalkylnyl, C-C-cycloalkyl, C-C-alkyl Sub R'' is methyl, stituted by a C-C-alkoxy radical and C-C-alkyl Substi 0210 R is fluorine, R is chlorine, R is methyl and tuted by a C-C-cycloalkyl radical. R'' is ethyl, 0191 Preference is given to compounds of the formula 0211 R is chlorine, R is chlorine, R is methyl and C.2.7, wherein m, n, R7, R7, Rand R', independently of R" is ethyl, each other, and more preferably in combination have one of 0212 R is fluorine, R is chlorine, R is methyl and the following meanings: R" is trifluoromethyl or (0192 m is 1: 0213 R’ is chlorine, R is chlorine, R is methyl and 0193 n is 1, 2 or 3: R" is trifluoromethyl; and compounds of formula (0194 R is selected from C-C-alkyl, Ca-Ca-cycloalkyl, C.2.1c, wherein and C-C2-alkyl Substituted by a C-C-cycloalkyl radical, 0214) R is fluorine, R is chlorine, R is methyl and in particular cyclopropylmethyl; R is cyclopropylmethyl, US 2011/0065579 A1 Mar. 17, 2011

0215 R is chlorine, R is chlorine, R is methyl and 0242. In this embodiment 2, the relative weight ratio of R is cyclopropylmethyl, pyroxasulfone to herbicide C.2 is preferably in the range from 0216 R is fluorine, R is chlorine, R is methyl and 1:500 to 500:1, in particular in the range from 1:250 to 250:1 R is methyl, and more preferably from 100:1 to 1:100. The relative weight 0217 R is chlorine, R is chlorine, R is methyl and ratio of herbicide A to herbicide B+herbicide C.2 is prefer R is methyl, ably in the range from 1500:1 to 1:20, in particular from 0218 R is fluorine, R is chlorine, R is methyl and 1000:1 to 1:10 and more preferably from 500:1 to 1:5. R is ethyl, 0243 According to a particular preferred embodiment of 0219 R is chlorine, R is chlorine, R is methyl and the invention, the component c) comprises at least one pyri R is ethyl, midindione herbicide C.2.1 (embodiment 2.1). Preferred 0220 R is fluorine, R is chlorine, R is methyl and pyrimidindione herbicides C.2.1 are butafenacil and R is trifluoromethyl or saflufenacil. Likewise preferred pyrimidindione herbicides 0221) R' is chlorine, R is chlorine, R is methyl and C.2.1 are compounds of the formula C.2.1b, wherein R is R is trifluoromethyl. fluorine, R is chlorine, R is methyl and R is cyclopropyl 0222 Preferred PPO inhibitors also include pyrazole type methyl. Likewise preferred pyrimidindione herbicides C.2.1 herbicides, in particular are compounds of the formula C.2.1c, wherein R is fluorine, 0223 compounds of the formula C.2.5a, wherein R" is chlorine, R is methyl and R is trifluoromethyl. 0224 R is fluorine, R is chlorine, R is methyl, Ris 0244. In particular preferred compositions of this embodi difluoromethoxy, R is chlorine and R is ethyl, ment 2.1, the herbicide C comprises or in particular is 0225 R is chlorine, R is chlorine, R is methyl, R is difluoromethoxy, R is chlorine and R is ethyl, butafenacil. 0226 R is fluorine, R is chlorine, R is methyl, Ris 0245. In other particular preferred compositions of this difluoromethoxy, R is bromine and R is ethyl, or embodiment 2.1, the herbicide C comprises or in particular is 0227 R’ is chlorine, R is chlorine, R is methyl, R saflufenacil. is difluoromethoxy, R is bromine and R is ethyl, 0246. In other particular preferred compositions of this and embodiment 2.1, the herbicide C comprises or in particular is 0228 compounds of the formula C.2.5b, which are a compound of the formula C.2.1b, wherein R is fluorine, R' selected from fluazolate and pyraflufen-ethyl. is chlorine, R is methyl and R is cyclopropylmethyl. 0229. Preferred PPO inhibitors also include triazinedione 0247. In other particular preferred compositions of this type herbicides, in particular compounds of the formula C.2.6 embodiment 2.1, the herbicide C comprises or in particular is and more preferably those, wherein the variable Y is S, Rf is a compound of the formula C.2.1c, wherein R is fluorine, R' fluorine, R is propargyl, R is methyl and R is methyl. is chlorine, R is methyl and R' is trifluoromethyl. 0230 Preferred PPO inhibitors also includedicarboxam 0248. In this embodiment 2.1 the relative weight ratio of ide type herbicides, in particular compounds of the formula pyroxasulfone and an herbicide of the group C.2.1 is prefer C.2.7 and more preferably the compound of the formula ably from 1:100 to 100:1 and more preferably from 50:1 to C.2.7a. 1:50. The relative weight ratio of herbicide A to herbicide 0231. The PPO inhibitor is more preferably selected from B+herbicide C.2.1 is preferably in the range from 1000:1 to the group consisting of 1:10 and more preferably from 500:1 to 1:5. 0232 C.2.1 pyrimidinedione herbicides (also termed as 0249 According to another particular preferred embodi phenyluracil herbicides), in particular compounds of the ment of the invention, the component c) comprises at least formulae C.2.1a, C.2.1b and C.2.1c and one dicarboximide herbicide of the group C.2.2 (embodiment 0233 C.2.2 N-phenylphthalimide herbicides (also termed 2.2). Preferred dicarboximide herbicides include cinidon, flu as dicarboximide herbicides), in particular compounds of mioxazin, flumiclorac, and flumipropyn. Also included are the formula C.2.2. the salts ofcinidon and flumiclorac, in particular their sodium 0234. Likewise, the PPO inhibitor is more preferably salts, potassium salts, ammonium salts or Substituted ammo selected from the group consisting of: nium salts as defined above, in particular mono-, di and tri 0235 C.2.5 pyrazole herbicides, in particular of the for C-Cs-alkylammonium salts such as isopropylammonium mula C.2.5 and most preferably of the formula C.2.5a, salts, and the esters of cinidon and flumiclorac, in particular especially compounds of the formula C.2.5a, wherein their C-C-alkyl esters, such as methylesters, ethylesters, 0236 R is fluorine, R is chlorine, R is methyl, R is isopropyl esters. Suitable examples of Such esters are cini difluoromethoxy, R is chlorine and R is ethyl, don-ethyl and flumiclorac-pentyl. 0237 R’ is chlorine, R is chlorine, R is methyl, R is 0250 In preferred compositions of this embodiment 2.2, difluoromethoxy, R is chlorine and R is ethyl, the herbicide C comprises or in particular is cinidon, flumi 0238 R is fluorine, R is chlorine, R is methyl, R is oxazin, flumiclorac, or flumipropyn, or a salt or an ester of difluoromethoxy, R is bromine and R is ethyl, or cinidon or flumiclorac. 0239 R is chlorine, R is chlorine, R is methyl, R is 0251. In a particular preferred composition of this difluoromethoxy, R is bromine and R is ethyl: embodiment 2.2, the herbicide C comprises or in particular is 0240 C.2.6 triazinedione herbicides, in particular com flumioxazin. pounds of the formula C.2.6, and most preferably a com 0252. In another particular preferred composition of this pound of the formula C.2.6, wherein the variable Y is S, R embodiment 2.2, the herbicide C comprises or in particular is is fluorine, R is propargyl, R is methyl and R is flumiclorac. methyl: 0253) In a further particular preferred composition of this 0241 C.2.7dicarboxamide herbicides, in particular of the embodiment 2.2, the herbicide C comprises or in particular is formula C.2.7 and most preferably of the formula C.2.7a. flumipropyn. US 2011/0065579 A1 Mar. 17, 2011

0254. In this embodiment 2.2 the relative weight ratio of 0269. In a particular preferred composition of this pyroxasulfone and an herbicide of the group C.2.2 is prefer embodiment 2.7, the herbicide C comprises or in particular is ably from 100:1 to 1:100, in particular from 50:1 to 1:50. The a compound of the formula C.2.7a. relative weight ratio of herbicide A to herbicide B+herbicide 0270. In this embodiment 2.7 the relative weight ratio of C.2.2 is preferably in the range from 1000:1 to 1:10 and more pyroxasulfone and an herbicide of the group C.2.7 is prefer preferably from 500:1 to 1:5. ably from 100:1 to 1:100, in particular from 50:1 to 1:50. The 0255 According to another particular preferred embodi relative weight ratio of herbicide A to herbicide B+herbicide ment of the invention, the component c) comprises at least C.2.7 is preferably in the range from 1000:1 to 1:50 and more one pyrazole herbicide of the group C.2.5 (embodiment 2.5). preferably from 500:1 to 1:10. 0256 Preferred pyrazole herbicides include compounds 0271 According to a third preferred embodiment of the of the formula C.2.5a and compounds of the formula C.2.5b, invention (embodiment 3), the herbicidal compositions of the which are preferably selected from fluazolate and pyraflufen invention additionally comprise at least one further herbicide ethyl C.3 which is a synthetic auxin. Synthetic auxins are com 0257. In preferred compositions of this embodiment 2.5, pounds wich act like the phytohormones auxins such indole the herbicide C comprises or in particular is compound of the 3-acetic acid. Synthetic auxins belong to the group O of the formula C.2.5a, which is selected from the compounds, HRAC classification system (see HRAC, Classification of wherein Herbicides According to Mode of Action, http://www.plant 0258 R is fluorine, R is chlorine, R is methyl, R is protection.org/hrac/MOA.html). difluoromethoxy, R is chlorine and R is ethyl, Herbicide compounds belonging to the group of synthetic (0259 R is chlorine, R is chlorine, R is methyl, R is auxins include e.g. difluoromethoxy, R is chlorine and R is ethyl, 0260 R is fluorine, R is chlorine, R is methyl, R is difluoromethoxy, R is bromine and R is ethyl, or C3.1 benzoic acid herbicides: C32 quinolinecarboxylic acid herbicides; 0261) R' is chlorine, R is chlorine, R is methyl, R is C.3.3 pyridine carboxylic acid herbicides; difluoromethoxy, R is bromine and R is ethyl. C.34 phenoxycarboxylic acid herbicides; 0262. In a particular preferred composition of this embodiment 2.5, the herbicide C comprises or in particular is a compound of the formula C.2.5a, wherein R is fluorine, R' 0272 Benzoic acid herbicides herbicides (C.3.1) include is chlorine, R is methyl, R is difluoromethoxy, R is chlorine e.g. dicamba, tricamba, chloramben and 2.3.6-TBA (2.3.6- trichlorobenzoic acid) and the salts and esters thereof. and R' is ethyl, 0273 Quinolinecarboxylic acid herbicides herbicides 0263. In another particular preferred composition of this (C.3.2) include e.g. quinclorac and quinmerac and the salts embodiment 2.5, the herbicide C comprises or in particular is and esters thereof. a compound of the formula C.2.5a, wherein R is chlorine, R' (0274 Pyridinecarboxylic acid herbicides herbicides (C.3. is chlorine, R is methyl, R is difluoromethoxy, R is bromine 3) include e.g. aminopyralid, clopyralid, picloram, triclopyr and R is ethyl. and fluoroxypyr and their salts and their esters. 0264. In this embodiment 2.5 the relative weight ratio of 0275 Phenoxycarboxylic acid herbicides (C.3.4) include, pyroxasulfone and an herbicide of the group C.2.5 is prefer e.g. phenoxyacetic acid herbicides Such as 2,4-D, 3,4-DA, ably from 100:1 to 1:100, in particular from 50:1 to 1:50. The MCPA, 2,4,5-T phenoxypropionic acid herbicides such as relative weight ratio of herbicide A to herbicide B+herbicide 2,4-DP (dichlorprop), 2,4-DP-P 4-CPP, 3,4-DP, fenoprop, C.2.5 is preferably in the range from 1000:1 to 1:50 and more CMPP (mecoprop), CMPP-P, and phenoxybutyric acid her preferably from 500:1 to 1:10. bicides such as 4-CPB, 2,4-DB, 3,4-DB, 2,4,5-TB, MCPB, 0265 According to another particular preferred embodi their salts and theiresters. Phenoxycarboxylic acid herbicides ment of the invention, the component c) comprises at least (b4) include 2,4-D, MCPA, 2,4-DP (dichlorprop), 2,4-DP-P, one triazindione herbicide of the group C.2.6 (embodiment CMPP (mecoprop), CMPP-P, MCPB, their salts and their 2.6). Preferred triazindione herbicides include compounds of esterS. the formula C.2.6, wherein wherein the variable Y is S, R is 0276. In this embodiment 3, the relative weight ratio of fluorine, R is propargyl, R is methyl and R is methyl. pyroxasulfone to herbicide of the group C.3 is preferably in 0266. In a particular preferred composition of this the range from 1:500 to 500:1, in particular in the range from embodiment 2.6, the herbicide C comprises or in particular is 1:250 to 250:1 and more preferably from 100:1 to 1:100. The a compound of the formula C.2.6 wherein the variable Y is S. relative weight ratio of herbicide A to herbicide B+herbicide R’ is fluorine, R is propargyl, R is methyl and R is C.3 is preferably in the range from 1500:1 to 1:20, in particu methyl. lar from 1000:1 to 1:10 and more preferably from 500:1 to 0267 In this embodiment 2.6 the relative weight ratio of 1:5. pyroxasulfone and an herbicide of the group C.2.6 is prefer 0277 According to a particular preferred embodiment of ably from 100:1 to 1:100, in particular from 50:1 to 1:50. The the invention, the component c) comprises at least one ben relative weight ratio of herbicide A to herbicide B+herbicide Zoic acid herbicide C.3.1 (embodiment 3.1). C.2.6 is preferably in the range from 1000:1 to 1:50 and more 0278 Preferred benzoic acid herbicides C.3.1 include preferably from 500:1 to 1:10. dicamba, tricamba, chloramben and 2.3.6-TBA (2.3.6- 0268 According to another particular preferred embodi trichlorobenzoic acid) and the salts the esters thereof, in par ment of the invention, the component c) comprises at least ticular their SSodium salt, potassium salt, ammonium salt or one triazindione herbicide of the group C.2.7 (embodiment Substituted ammonium salts as defined above, in particular 2.7). Preferred triazindione herbicides include the compound mono-, di- and tri-C-C-alkylammonium salts such as of the formula C.2.7a. methylammonium, dimethylammonium and isopropylam US 2011/0065579 A1 Mar. 17, 2011 monium, mono-, di- and tri-hydroxy-C-C-alkylammonium one pyridinecarboxylic acid herbicide C.3.3 (embodiment salts such as hydroxyethylammonium, di(hydroxyl-ethyl) 3.3). Pyridinecarboxylic acid herbicides (group C.3.3) are ammonium, tri(hydroxyethyl)ammonium, hydroxypropy known e.g. f. D. S. Tomlin, “The Pesticide Manual, 13th lammonium, di(hydroxypropyl)ammonium and tri(hydrox Edition, BCPC (2003), and also from The Compendium of ypropyl)ammonium salts and their esters, in particular its Pesticide Common Names, http://www.alanwood.net/pesti C-C-alkyl esters and C-C-alkoxy-C-C-alkyl esters, cides/. Such as methylesters, ethylesters, iso-propyl, butyl, hexyl, 0287 Pyridinecarboxylic acid herbicides include ami heptyl, iso-heptyl, isooctyl, 2-ethylhexyl and butoxyethyl nopyralid, clopyralid, picloram, triclopyr and fluoroxypyr esters. Suitable examples of Such salts are dicamba-Sodium, and their salts and their esters, in particular their sodium salt, dicamba-potassium, dicamba-methylammonium, dicamba potassium salt, ammonium salt or Substituted ammonium isopropylammonium, dicamba-olamine, dicamba-diola salts as defined above, in particular mono-, di- and tri-C-C- mine, dicamba-trolamine, tricamba-Sodium, tricamba-potas alkylammonium salts such as methylammonium, dimethy sium, tricamba-methylammonium, tricamba lammonium and isopropylammonium, mono-, di- and tri isopropylammonium, tricamba-olamine, tricamba hydroxy-C-C-alkylammonium salts Such aS diolamine, tricamba-trolamine, chloramben-ammonium, hydroxyethylammonium, di(hydroxyethyl)ammonium, tri chloramben-methylammonium, chloramben-sodium, (hydroxyethyl)ammonium, hydroxypropylammonium, chloramben-diolamine, 2.3.6-T-sodium, 2.3,6-dimethylam di(hydroxypropyl)ammonium and tri(hydroxypropyl)ammo monium. Suitable examples of Such esters are dicamba-me nium salts and their esters, in particular its C-Cs-alkyl esters thyl and chloramben-methyl. and C-C-alkoxy-C-C-alkyl esters, such as methylesters, 0279. In particular preferred compositions of this embodi ethylesters, iso-propyl, butyl, hexyl, heptyl, iso-heptyl, isooc ment 3.1, the herbicide C comprises or in particular is tyl, 2-ethylhexyl and butoxyethyl esters. Suitable examples of dicamba or a salt thereof. Such salts and esters are aminopyralid-potassium, aminopy 0280. In this embodiment 3.1 the relative weight ratio of ralid-tris(2-hydroxypropyl)ammonium, clopyralid-potas pyroxasulfone and a benzoic acid herbicide is preferably sium, clopyralid-olamine, clopyralid-tris(2-hydroxypropyl) from 1:250 to 250:1, in particular from 100:1 to 1:100. The ammonium, clopyralid-methyl, picloram-potassium, relative weight ratio of herbicide A to herbicide B+herbicide picloram-triethylammonium, picloram-tris(2-hydroxypro C.3.1 is preferably in the range from 1000:1 to 1:10 and more pyl)ammonium, picloram-methyl, picloram-2-ethylhexyl, preferably from 500:1 to 1:5. picloram-isooctyl, fluoroxypyr-meptyl, fluoroxypyrbutom (0281. According to another particular preferred embodi ethyl, triclopyr-triethylammonium, triclopyr-ethyl and triclo ment of the invention, the component c) comprises at least pyr-butotyl. one quinolinecarboxylic acid herbicide C.3.2 (embodiment 0288. In particular preferred compositions of this embodi 3.2). Quinolinecarboxylic acid herbicides (group C.2.2) are ment 3.3, the herbicide C comprises or in particular is flu known e.g. from C. D. S. Tomlin, “The Pesticide Manual”. oroxypyr or a salt or ester thereof. 13th Edition, BCPC (2003), and also from The Compendium 0289. In this embodiment 3.3 the relative weight ratio of of Pesticide Common Names, http://www.alanwood.net/pes pyroxasulfone and pyridinecarboxylic acid herbicide is pref ticides/. erably from 250:1 to 1:250, in particular from 100:1 to 1:100. 0282 Preferred quinolinecarboxylic acid herbicides The relative weight ratio of herbicide A to herbicide B+her include quinclorac, quinmerac, their salts and their esters, in bicide C.3.3 is preferably in the range from 1000:1 to 1:10 and particular their sodium salt, potassium salt, ammonium salt or more preferably from 500:1 to 1:5. Substituted ammonium salts as defined above, in particular 0290 According to a further embodiment of the invention, mono-, di- and tri-C-C-alkylammonium salts such as the component c) comprises at least one phenoxycarboxylic methylammonium, dimethylammonium and isopropylam acid herbicide C.3.4 (embodiment 3.4). Phenoxycarboxylic monium, mono-, di- and tri-hydroxy-C-C-alkylammonium herbicides (group C.3.4) are known e.g. from C. D. S. Tomlin, salts such as hydroxyethylammonium, di(hydroxyethyl)am “The Pesticide Manual, 13th Edition, BCPC (2003), and monium, tri(hydroxyethyl)ammonium, hydroxypropylam also from The Compendium of Pesticide Common Names, monium, di(hydroxypropyl)ammonium and tri(hydroxypro http://www.alanwood.net/pesticides/. pyl)ammonium salts and their esters, in particular its C-Cs 0291 Preferred phenoxycarboxylic acid herbicides alkyl esters and C-C-alkoxy-C-C-alkyl esters, such as include 2,4-D, 2,4-DP (dichlorprop), 2,4-DP-P, CMPP methylesters, ethylesters, iso-propyl, butyl, hexyl, heptyl, (mecoprop), CMPP-P, MCPA, MCPB, their salts and their iso-heptyl, isooctyl, 2-ethylhexyl and butoxyethyl esters. esters, in particular their sodium salt, potassium salt, ammo 0283. In particular preferred compositions of this embodi nium salt or Substituted ammonium salts as defined above, in ment 3.2, the herbicide B comprises or in particular is quin particular mono-, di- and tri-C-C-alkylammonium salts clorac or a salt or ester thereof. Such as methylammonium, dimethylammonium and isopro 0284. In other particular preferred compositions of this pylammonium, mono-, di- and tri-hydroxy-C-C-alkylam embodiment 3.2, the herbicide B comprises or in particular is monium salts such as hydroxyethylammonium, di(hydroxy quinmerac or a salt or ester thereof. ethyl)ammonium, tri(hydroxyethyl)ammonium, 0285. In this embodiment 3.2 the relative weight ratio of hydroxypropylammonium, di(hydroxypropyl)ammonium pyroxasulfone and quinolinecarboxylic acid herbicide is and tri(hydroxypropyl)ammonium salts and their esters, in preferably from 1:250 to 250:1, in particular from 100:1 to particular its C-Cs-alkyl esters and C-C-alkoxy-C-C- 1:100. The relative weight ratio of herbicide A to herbicide alkyl esters, such as methylesters, ethylesters, iso-propyl. B+herbicide C.3.2 is preferably in the range from 1000:1 to butyl, hexyl, heptyl, iso-heptyl, isooctyl, 2-ethylhexyl and 1:10 and more preferably from 500:1 to 1:5. butoxyethyl esters. Suitable examples of such salts and esters 0286 According to another particular preferred embodi are When this Substance is used as an ester or a salt, its identity ment of the invention, the component c) comprises at least should be stated, for example 2,4-D-ammonium, 2,4-D-bu US 2011/0065579 A1 Mar. 17, 2011 totyl, 2,4-D-2-butoxypropyl. 2,4-D-3-butoxypropyl. 2,4-D- 0301 In a particular preferred compositions of this butyl, 2,4-D-diethylammonium, 2,4-D-dimethylammonium, embodiment 4, the herbicide C comprises or in particular is 2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-D-ethyl, isoxaflutole. 2,4-D-2-ethylhexyl, 2,4-D-heptylammonium, 2,4-D-isobu 0302) In another particular preferred compositions of this tyl, 2,4-D-isoctyl, 2,4-D-isopropyl. 2,4-D-isopropylammo embodiment 4, the herbicide C comprises or in particular is nium, 2,4-D-lithium,2,4-D-meptyl, 2,4-D-methyl, 2,4-D-oc mesotrione. tyl, 2,4-D-penty1, 2,4-D-propyl. 2,4-D-Sodium, 2,4-D- 0303. In a further particular preferred compositions of this tefuryl, 2,4-D-tetradecylammonium, 2,4-D- embodiment 4, the herbicide C comprises or in particular is triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonium, Sulcotrione. 2,4-D-trolamine, MCPA-butotyl, MCPA-butyl, MCPA-dim ethylammonium, MCPA-diolamine, MCPA-ethyl, MCPA-2- 0304. In a further particular preferred compositions of this ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopro embodiment 4, the herbicide C comprises or in particular is pyl, MCPA-methyl, MCPA-olamine, MCPA-potassium, tembotrione. MCPA-sodium, MCPA-trolamine, dichlorprop-butotyl, 0305. In another particular preferred compositions of this dichlorprop-dimethylammonium, dichlorprop-ethylammo embodiment 4, the herbicide C comprises or in particular is nium, dichlorprop-2-ethylhexyl, dichlorpropisoctyl, dichlor toprameZone. prop-methyl, dichlorprop-potassium, dichlorprop-sodium, 0306 In the compositions of this embodiment 4, the rela dicloprop-P-dimethylammonium, mecoprop-dimethylam tive weight ratio of pyroxasulfone to herbicide C.4 is prefer monium, mecoprop-diolamine, mecoprop-ethadyl, meco ably in the range from 1:100 to 100:1 and more preferably prop-isoctyl, mecoprop-methyl, mecoprop-potassium, from 50:1 to 1:50. The relative weight ratio of herbicide A to mecoprop-sodium, mecoprop-trolamine, mecoprop-P-dim herbicide B+herbicide C.4 is preferably in the range from ethylammonium, mecoprop-P-isobutyl, mecoprop-P-potas 1500:1 to 1:20, in particular from 1000:1 to 1:10 and more sium, MCPB-methyl, MCPB-ethyl and MCPB-sodium. preferably from 500:1 to 1:5. 0292. In particular preferred compositions of this embodi 0307 According to a fifth preferred embodiment of the ment, the herbicide C comprises or in particular is 2,4-D or a invention (embodiment 5), the herbicidal compositions of the salt or ester thereof. invention additionally comprise at least one further herbicide 0293. In particular preferred compositions of this embodi C.5 which is an inhibitor of the phytoene desaturase (PDS inhibitor). PDS inhibitors are compounds which have a mode ment, the herbicide C comprises or in particular is MCPA or of action comprising the inhibition of the carotenoid biosyn a salt or ester thereof. thesis in plants at the phytoene desaturase step and which 0294. In particular preferred compositions of this embodi belong to the group F 1 of the HRAC classification system ment, the herbicide C comprises or in particular is dicloprop, (see HRAC, Classification of Herbicides According to Mode dicloprop-P or a salt or ester thereof. of Action, http://www.plantprotection.org/hrac/MOA.html). 0295. In particular preferred compositions of this embodi (0308 Suitable PDS inhibitors of the group C.5 are known ment, the herbicide C comprises or in particular is mecoprop, from e.g. G. Hamprecht et al. “Phytoene Desaturase Inhibi mecoprop-P or a salt or ester thereof. tors' in “Modern Crop Protection Compounds' Vol.1, Wiley 0296. In particular preferred compositions of this embodi VHC 2007, pp 187-211; from EP 723960 C. D. S. Tomlin, ment, the herbicide C comprises or in particular is MCPB or “The Pesticide Manual, 13th Edition, BCPC (2003) and also a salt or ester thereof. from The Compendium of Pesticide Common Names http:// 0297. In this embodiment 3.4 the relative weight ratio of www.alanwood.net/pesticides/. pyroxasulfone and phenoxycarboxylic acid herbicide is pref (0309 Suitable PDS inhibitors of the group C.5 include e.g. erably from 500:1 to 1:500, in particular from 250:1 to 1:250. pyridaZinone herbicides, such as norflurazon, pyridinecar The relative weight ratio of herbicide A to herbicide B+her boxamide herbicides, such as flufenican, diflufenican and bicide C.3.4 is preferably in the range from 1000:1 to 1:10 and picolinafen, as well as herbicides not belonging to a common more preferably from 500:1 to 1:5. group, Such as beflubutamid, fluridone, fluorochloridone and 0298. According to a fourth preferred embodiment of the flurtamone. Preferred PDS inhibitors according to the present invention (embodiment 4), the herbicidal compositions of the invention are selected from the group consisting of pyridin invention additionally comprise at least one further herbicide ecarboxamide herbicides, such as flufenican, diflufenican and C.4 which is an inhibitor of 4-hydroxyphenylpyruvate dioxy picolinafen. genase (HPPD inhibitor). HPPD inhibitors belong to the 0310. In particular preferred compositions of this embodi group F2 of the HRAC classification system (see HRAC, ment 5, the herbicide C comprises or in particular is picolin Classification of Herbicides According to Mode of Action, afen. This compound is known e.g. from EP 447004 (Shell http://www.plantprotection.org/hrac/MOA.html). Int. Res.). 0299 Herbicide compounds belonging to the group of 0311. In other particular preferred compositions of this HPPD inhibitors include toprameZone, tembotrione, isox embodiment, the herbicide C comprises or in particular is aflutole, mesotrione and Sulcotrione. diflufenican. This compound is known e.g. from EP 53011 0300 Isoxaflutole is a well known herbicide and commer (May & Baker Ltd.). cially available, e.g. under the trade name BALANCE(R) and 0312. In the compositions of the embodiment 5the relative MERLINR). Mesotrione is a well known herbicide and com weight ratio of pyroxasulfone to herbicide C.5 is preferably in mercially available, e.g. under the trade name CALLISTOR). the range from 1:200 to 200:1 and more preferably from Sulcotrione is a well known herbicide and commercially 100:1 to 1:100. The relative weight ratio of herbicide A to available, e.g. under the trade name MIKADOR. Tro herbicide B+herbicide C.5 is preferably in the range from pramzeone is a well known herbicide and commercially 1500:1 to 1:20, in particular from 1000:1 to 1:10 and more available, e.g. under the trade names IMPACTR) and CLIOR). preferably from 500:1 to 1:5. US 2011/0065579 A1 Mar. 17, 2011

0313 According to a sixth preferred embodiment of the 0322 Methylthiotriazine herbicides (C.6.8) include e.g. invention (embodiment 6), the herbicidal compositions of the ametryn, aZiprotryne, cyanatryn, desmetryn, dimethametryn, invention additionally comprise at least one further herbicide methoprotryne, prometryn, simetryn and terbutryn. A pre C.6 which is an inhibitor of electron transfer in photosynthe ferred methylthiotriazine herbicide is ametryn. sis in plants. These compounds have a mode of action com 0323. In the compositions of the embodiment 6 the relative prising the inhibition of the electron transfer in photosystem weight ratio of pyroxasulfone to herbicide C.6 is preferably in II of the photosynthesis in plants (PSII inhibitors). They the range from 1:500 to 500:1, in particular in the range from belong to the groups C to C of the HRAC classification 1:250 to 250:1 and more preferably from 100:1 to 1:100. The system (see HRAC, Classification of Herbicides According to relative weight ratio of herbicide A to herbicide B+herbicide Mode of Action, http://www.plantiprotection.org/hrac/MOA. C.16 is preferably in the range from 1500:1 to 1:20, in par html). ticular from 1000:1 to 1:10 and more preferably from 500:1 to Suitable PSII inhibitors are selected from the group consist 1:5. ing of 0324 Particular preference is given to PSII inhibitors of the herbicide groups 0325 C.6.1, in particular chlortoluron, diuron, linuron, isoproturon and/or tebuthiuron C.6.1 arylurea herbicides; C.6.2 triazin(di)one herbicides; 0326 C.6.2, in particular hexazinon, metamitron and/or C.63 chlorotriazine herbicides: metribuzin, C64 pyridaZinone herbicides; 0327 C.6.3, in particular atrazine and/orterbuthylazine C.6.5 phenylcarbamate herbicides; and C.6.6 nitrile herbicides: 0328. C.6.8, in particular ametryn, C.6.7 bentazone and its salts such as bentazone sodium; and C.6.8 methylthiotriazine herbicides. and mixtures thereof. 0329. More preference is given to compostions of the embodiment 6, where the PSII inhibitor is selected from the 0314 PSII inhibitors are known e.g. from K.-W. Munks group of atrazine, terbuthylazin, ametryn, hexaZinone, and K.-H. Miller “Photosynthesis Inhibitors” in “Modern metribuzin, diuron, isoproturon and their agriculturally Crop Protection Compounds” Vol. 1, Wiley-VHC 2007, pp acceptable salts and mixtures thereof. 359-400; C. D. S. Tomlin, “The Pesticide Manual, 13th 0330. In particular preferred compositions of this embodi Edition, BCPC (2003) and also from The Compendium of ment 6, the herbicide C comprises or in particular is hexazi Pesticide Common Names, http://www.alanwood.net/pesti OC. cides/. 0331. In other particular preferred compositions of this 0315 Arylurea herbicides herbicides (C.6.1) include e.g. embodiment 6, the herbicide C comprises or in particular is chlorbromuron, chlorotoluron, chloroXuron, dimefuron, diu metribuzin. ron, ethidimuron, fenuron, fluometuron, isoproturon, isuron, 0332. In other particular preferred compositions of this linuron, methabenzthiaZuron, metobromuron, metoxuron, embodiment 6, the herbicide C comprises or in particular is monolinuron, neburon, siduron, tetrafluoron and thebuthi diuron. uron. Preferred arylurea herbicides herbicides (C.6.1) include 0333. In other particular preferred compositions of this chlortoluron, diuron, linuron, isoproturon and tebuthiuron. embodiment 6, the herbicide C comprises or in particular is 0316 Triazin(di)one herbicides (C.6.2) (i.e. triazinone isoproturon. and triazindione herbicides) include e.g. ametridione, 0334. In other particular preferred compositions of this amibuzin, hexazinone, isomethiozin, metamitron and embodiment 6, the herbicide C comprises or in particular is metribuzin. Preferred triazin(di)one herbicides (C.6.2) atrazine. include hexazinon, metamitron and metribuzin. 0335. In other particular preferred compositions of this 0317 Chlorotriazine herbicides (C.6.3) include e.g. atra embodiment 6, the herbicide C comprises or in particular is Zine, chlorazine, cyanazine, cyprazine, eglinazine, ipazine, ametryn. mesoprazine, procyazine, proglinazine, propazine, Sebuthy 0336. In other particular preferred compositions of this lazine, simazine, terbuthylazine and trietazine. Preferred embodiment 6, the herbicide C comprises or in particular is chlorotriazine herbicides (C.6.3) include atrazine, terbuthy terbuthylazin. lazine and Simazine. 0337. In other particular preferred compositions of this 0318 Pyridazinone herbicides (C.6.4) include e.g. bro embodiment 6, the herbicide C comprises or in particular is a mpyrazon, chloridazon, dimidazon, mefflurazon, norflura mixture of atrazine and ametryn. Zon, oxapyrazon and pydanon. A preferred pyridazinone her 0338. In other particular preferred compositions of this bicide is chloridazon. embodiment 6, the herbicide C comprises or in particular is a 0319 Phenylcarbamate herbicides (C.6.5) include e.g. mixture of atrazine and metribuzin. desmedipham, phenisopham, phenmedipham and phenme 0339 According to a seventh preferred embodiment of the dipham-ethyl. invention (embodiment 7), the herbicidal compositions of the 0320 Nitrile herbicides (C.6.6) include e.g. bromobonil, invention additionally comprise at least one further herbicide bromoxynil, chloroxynil, dichlobenil, iodobonil and ioxynil C.7 which is an inhibitor of microtubule assembly (MTA and their salts and esters, in particular in case of bromoxynil. inhibitor). MTA inhibitors are compounds which have a mode chloroxynil and ioxynil. A preferred nitrile herbicide is bro of action comprising the inhibition of the microtubule assem moxynil. bly in plants and which belong to the group K1 of the HRAC 0321 Benzothiadiazinone herbicides (C.6.7) include ben classification system (see HRAC, Classification of Herbi taZone and its salts, in particular its alkalimetal salts such as cides According to Mode of Action, http://www.plantprotec bentaZone-sodium. tion.org/hrac/MOA.html). US 2011/0065579 A1 Mar. 17, 2011

0340 MTA inhibitors include e.g. dinitroanilide herbi cides, such as benfluralin, butralin, dinitramine, ethalfluralin, -continued oryzalin, pendimethalin, and trifluralin, phosphoroamidate C.8.1 oxyacetamide herbicides, such as flufenacet and mefenacet, herbicides, such as amiprophos-methyl and butamiphos, C.8.3 acetamide herbicides, such as as diphenamid, napropamide and pyridine herbicides, such as dithiopyr and thiazopyr, benza naproanilide, mide herbicides, such as propyZamide and tebutam, and ben C.8.3 tetrazolinone herbicides, such as fentraZamide as well as Zoic acid herbicides, such as chlorthal. The term "MTA C.8.4 VLCFA-herbicides not belonging to a common group, such as inhibitor is meant herein to also include the respective salts, anilofos, cafenstrole and piperophos. isomers and esters of the above mentioned compounds. Suit able salts are e.g. salts of alkaline or earth alkaline metals or 0347 The term “VLCFA inhibitor is meant hereinto also ammonium or organoammonium salts, for instance, Sodium, include the respective salts, isomers and esters of the above potassium, ammonium, isopropyl ammonium etc. Suitable mentioned compounds. Suitable salts are e.g. salts of alkaline isomers are e.g. Stereo isomers such as the enantiomers. Suit or earth alkaline metals or ammonium or organoammonium able esters are e.g. C-C-(branched or non-branched) alkyl salts, for instance, sodium, potassium, ammonium, isopropyl esters, such as methylesters, ethylesters, isopropyl esters. ammonium etc. Suitable isomers are e.g. Stereo isomers such 0341 Preferred MTA inhibitors according to the present as the enantiomers. Suitable esters are e.g. C-C-(branched invention are selected from the group consisting of dinitroa or non-branched) alkyl esters. Such as methylesters, ethylest niline herbicides, in particular benfluralin, butralin, dinitra ers, isopropyl esters. mine, ethalfluralin, fluchloralin, isopropalin, methalpropalin, (0348 Preferred VLCFA inhibitors according to the nitralin, ory Zalin, pendimethalin, prodiamine, profluralin and embodiment 8 are selected from the group consisting of chlo trifluralin, more preferably oryzalin, pendimethalin and tri roacetamide herbicides (embodiment 8.1), in particular fluralin. Dinitroaniline herbicides are known e.g. from U.S. acetochlor, dimethachlor, dimethenamid, dimethenamid-P, Pat. No. 3,257, 190: U.S. Pat. No. 3,321,292; U.S. Pat. No. metaZachlor, propisochlor, pethoxamide, metolachlor, and 3,367,949; C. D. S. Tomlin, “The Pesticide Manual, 13th metolachlor-S and oxyacetamide herbicides (embodiment Edition, BCPC (2003) and also from The Compendium of 8.2), in particular flufenacet. Pesticide Common Names, http://www.alanwood.net/pesti 0349. In the compositions of the embodiment 8 (and like cides/. wise in embodiments 8.1 and 8.2) the relative weight ratio of 0342. In the compositions of the embodiment 7 the relative pyroxasulfone to herbicide C.8 is preferably in the range from weight ratio of pyroxasulfone to herbicide C.7 is preferably in 1:250 to 250:1, in particularintherange of 1:200 to 200:1 and the range from 1:500 to 100:1 and more preferably from 50:1 more preferably from 150:1 to 1:150. The relative weight to 1:300. The relative weight ratio of herbicide A to herbicide ratio of herbicide A to herbicide B+herbicide C.8 is prefer B+herbicide C.7 is preferably in the range from 1500:1 to ably in the range from 1500:1 to 1:20 and more preferably 1:100, in particular from 1000:1 to 1:80 and more preferably from 1000:1 to 1:10. from 500:1 to 1:50. 0350. In particular preferred compositions of this embodi 0343. In particular preferred compositions of this embodi ment 8.1, the herbicide C comprises or in particular is ment 7, the herbicide C comprises or in particular is oryzalin. acetochlor. 0344. In further particular preferred compositions of this 0351. In other particular preferred compositions of this embodiment 7, the herbicide C comprises or in particular is embodiment 8.1, the herbicide C comprises or in particular is pendimethalin. dimethachlor. 0345. In the particular preferred compositions of embodi 0352. In further particular preferred compositions of this ment 7 the relative weight ratio of pyroxasulfone and dini embodiment 8.1, the herbicide C comprises or in particular is troaniline herbicide is preferably from 100:1 to 1:500 and dimethenamid. more preferably from 50:1 to 1:300. The relative weight ratio 0353. In further particular preferred compositions of this of herbicide A to herbicide B+herbicide C.7 is preferably in embodiment 8.1, the herbicide C comprises or in particular is the range from 1500:1 to 1:100, in particular from 1000:1 to dimethenamid-P. 1:80 and more preferably from 500:1 to 1:80. 0354. In further particular preferred compositions of this 0346 According to a eighth preferred embodiment of the embodiment 8.1, the herbicide C comprises or in particular is invention (embodiment 8), the herbicidal compositions of the metaZachlor. invention additionally comprise at least one further herbicide 0355. In further particular preferred compositions of this C.8 which is an inhibitor of the VLCFA synthesis (VLCFA embodiment 8.1, the herbicide C comprises or in particular is inhibitor). VLCFA inhibitors are compounds which have a propisochlor. mode of action comprising the inhibition of the VLCA syn 0356. In further particular preferred compositions of this thesis and/or the inhibition of cell division in plants and which embodiment 8.2, the herbicide C comprises or in particular is belong to the group K3 of the HRAC classification system flufenacet. (see HRAC, Classification of Herbicides According to Mode 0357. In further preferred compositions of this embodi of Action, http://www.plantprotection.org/hrac/MOA.html). ment 8, the herbicide C comprises or in particular is a mixture VLCFA inhibitors include e.g. of at least one VLCFA inhibitor herbicide, in particular at least one chloroacetamide herbicide and/or at least one oxy acetamide, with at least one herbicides of the group C.3, in particular of the group C.3.1 Such as dicamba or a salt thereof, C.8.1 chloroacetamide herbicides, such as acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metaZachlor, or of the group C.3.2 Such as quinmerac or a salt thereof metolachlor, S-metolachlor, pethoxamid, pretilachlor, propachlor, (embodiment 8.3) and/or with clomazone (embodiment 8.4). propisochlor and thenylchlor, In these preferred compositions of the embodiments 8.3 and 8.4 the chloroacetamide herbicide is preferably selected from US 2011/0065579 A1 Mar. 17, 2011

acetochlor, dimethachlor, dimethenamid, dimethenamid-P, 0372. In further particular preferred compositions of this metaZachlor, metolachlor, S-metolachlor, pethoxamide and embodiment 8.5, the herbicide C comprises or in particular is propisochlor. In these preferred compositions the oxyaceta a mixture of flufenacet and at least one PSII inhibitor selected mide herbicide is preferably flufenacet. from atrazine, metribuzine and terbuthylazine. 0358. In further particular preferred compositions of this 0373). In the embodiment 8.5 the relative weight ratio of embodiment 8.3, the herbicide C comprises or in particular is pyroxasulfone and herbicide C.8+C.6 is preferably from a mixture of quinmerac or a salt thereof and metaZachlor. 500:1 to 1:500 and more preferably from 250:1 to 1:250. The 0359. In further particular preferred compositions of this relative weight ratio of herbicide A to herbicide B+herbicide embodiment 8.3, the herbicide C comprises or in particular is C.6+herbicide C.8 is preferably in the range from 1000:1 to a mixture of dicamba or a salt thereof and metaZachlor. 1:50 and more preferably from 500:1 to 1:30. 0360. In further particular preferred compositions of this 0374. In further preferred compositions of the invention, embodiment 8.3, the herbicide C comprises or in particular is the herbicide C comprises or in particular is a mixture of an a mixture of dicamba or a salt thereof and flufenacet. VLCFA inhibitor, in particular an oxyacetamide and/or a 0361. In further particular preferred compositions of this chloroacetamide, at least one auxin herbicide C.3, in particu embodiment 8.3, the herbicide C comprises or in particular is lara herbicide of the groups C.3.1, C.3.2 and/or C.3.4, and at a mixture of dicamba or a salt thereof and dimethenamid-P, least one PSII inhibitor, in particular selected from the groups optionally comprising a PSII inhibitor herbicide such as atra C.6.1, C.6.2. C.6.3 and C.6.8 (embodiment 8.6). Zine or metribuzin. 0375. In the preferred compositions of the embodiment 0362. In further particular preferred compositions of this 8.6 the auxin herbicide C.3 is at least one benzoic acid her embodiment 8.4, the herbicide C comprises or in particular is bicide of the group C.3.1, such as dicamba or a salt thereof, or a mixture of clomaZone and metaZachlor. quinolinecarboxylic acid herbicide of the group C.3.2. Such as 0363. In further particular preferred compositions of this quinmerac or a salt thereof. embodiment 8.4, the herbicide C comprises or in particular is 0376. In the preferred compositions of the embodiment a mixture of clomaZone and dimethenamid-P. 8.6 the chloroacetamide herbicide is preferably selected from 0364. In the embodiment 8.3 the relative weight ratio of acetochlor, dimethachlor, dimethenamid, dimethenamid-P, pyroxasulfone and herbicide C.8+C.3 is preferably from metaZachlor, metolachlor, S-metolachlor, pethoxamide and 500:1 to 1:500 and more preferably from 250:1 to 1:250. The propisochlor. In these preferred compositions the oxyaceta relative weight ratio of herbicide A to herbicide B+herbicide mide herbicide is preferably flufenacet. C.3+herbicide C.8 is preferably in the range from 1000:1 to 0377. In the preferred compositions of the embodiment 1:50 and more preferably from 500:1 to 1:30. 8.6 the PSII-inhibitor is preferably selected from atrazine, 0365. In the embodiment 8.4 the relative weight ratio of terbuthylazin, ametryn, hexazinone, metribuzin, diuron, iso pyroxasulfone and herbicide C.8+clomazone is preferably proturon. from 500:1 to 1:500 and more preferably from 250:1 to 1:250. 0378. In particular preferred compositions of this embodi The relative weight ratio of herbicide A to herbicide B+clo ment 8.6, the herbicide C comprises or in particular is a mazone+herbicide C.8 is preferably in the range from 1000:1 mixture of dimethenamid-P, at least one PSII inhibitor to 1:50 and more preferably from 500:1 to 1:30. selected from atrazine, metribuzine and terbuthylazine, and 0366. In further preferred compositions of the invention, an auxin herbicide, in particulara benzoic acid herbicide Such the herbicide C comprises or in particular is a mixture of an as dicamba. VLCFA inhibitor, in particular an oxyacetamide and/or a 0379. In particular preferred compositions of this embodi chloroacetamide, and at least one PSII inhibitor, in particular ment 8.6, the herbicide C comprises or in particular is a selected from the groups C.6.1, C.6.2. C.6.3 and C.6.8 (em mixture of metazachlor, at least one PSII inhibitor selected bodiment 8.5). from atrazine, metribuzine and terbuthylazine, and an auxin 0367. In the preferred compositions of the embodiment herbicide, in particular a benzoic acid herbicide such as 8.5 the chloroacetamide herbicide is preferably selected from dicamba. acetochlor, dimethachlor, dimethenamid, dimethenamid-P, 0380. In particular preferred compositions of this embodi metaZachlor, metolachlor, S-metolachlor, pethoxamide and ment 8.6, the herbicide C comprises or in particular is a propisochlor. In these preferred compositions the oxyaceta mixture of alachlor, at least one PSII inhibitor selected from mide herbicide is preferably flufenacet. atrazine, metribuzine and terbuthylazine, and an auxin herbi 0368. In the preferred compositions of the embodiment cide, in particular a benzoic acid herbicide Such as dicamba. 8.5 the PSII-inhibitor is preferably selected from atrazine, 0381. In particular preferred compositions of this embodi terbuthylazin, ametryn, hexazinone, metribuzin, diuron, iso ment 8.6, the herbicide C comprises or in particular is a proturon. mixture of flufenacet, at least one PSII inhibitor selected from 0369. In particular preferred compositions of this embodi atrazine, metribuzine and terbuthylazine, and an auxin herbi ment 8.5, the herbicide C comprises or in particular is a cide, in particular a benzoic acid herbicide Such as dicamba. mixture of dimethenamid-P and at least one PSII inhibitor 0382. In the embodiment 8.6 the relative weight ratio of selected from atrazine, metribuzine and terbuthylazine. pyroxasulfone and herbicide C.8+C.6+C.3 is preferably from 0370. In further particular preferred compositions of this 500:1 to 1:500 and more preferably from 250:1 to 1:250. The embodiment 8.5, the herbicide C comprises or in particular is relative weight ratio of herbicide A to herbicide B+herbicide a mixture of metazachlor and at least one PSII inhibitor C.3+herbicide C.6+herbicide C.8 is preferably in the range selected from atrazine, metribuzine and terbuthylazine. from 1000:1 to 1:50 and more preferably from 500:1 to 1:30. 0371. In further particular preferred compositions of this 0383. In further preferred compositions of the invention, embodiment 8.5, the herbicide C comprises or in particular is the herbicide C comprises or in particular is a mixture of an a mixture of alachlor and at least one PSII inhibitor selected VLCFA inhibitor, in particular an oxyacetamide and/or a from atrazine, metribuzine and terbuthylazine. chloroacetamide, and at least one protoporphyrinogen oxi US 2011/0065579 A1 Mar. 17, 2011

dase inhibitor which is in particular selected from the groups 0396. In particular preferred compositions of this embodi C.2.1 and C.2.2 (embodiment 8.7). ment 8.9, the herbicide C comprises or in particular is a 0384. In the preferred compositions of the embodiment mixture of metazachlor, at least one PSII inhibitor selected 8.7 the PPO inhibitor heribicide is select from the group of from atrazine, metribuzine and terbuthylazine, and a HPPD pyrimidinedioneherbicides, in particular saflufenacilor a salt inhibitor herbicide, in particular toprameZone. thereof. 0397. In particular preferred compositions of this embodi 0385. In the preferred compositions of the embodiment ment 8.9, the herbicide C comprises or in particular is a 8.7 the chloroacetamide herbicide is preferably selected from mixture of alachlor, at least one PSII inhibitor selected from acetochlor, dimethachlor, dimethenamid, dimethenamid-P, atrazine, metribuzine and terbuthylazine, and a HPPD inhibi metaZachlor, metolachlor, S-metolachlor, pethoxamide and tor herbicide, in particular toprameZone. propisochlor. In these preferred compositions the oxyaceta 0398. In particular preferred compositions of this embodi mide herbicide is preferably flufenacet. ment 8.9, the herbicide C comprises or in particular is a 0386. In the embodiment 8.7 the relative weight ratio of mixture of flufenacet, at least one PSII inhibitor selected from pyroxasulfone and herbicide C.2+C.8 is preferably from atrazine, metribuzine and terbuthylazine, and a HPPD inhibi 200:1 to 1:200 and more preferably from 100:1 to 1:100. The tor herbicide, in particular toprameZone. relative weight ratio of herbicide A to herbicide B+herbicide 0399. In the embodiment 8.9 the relative weight ratio of C.2+herbicide C.8 is preferably in the range from 1000:1 to pyroxasulfone and herbicide C.8+C.6+C.4 is preferably from 1:10 and more preferably from 500:1 to 1:10. 200:1 to 1:500 and more preferably from 100:1 to 1:250. The 0387. In further preferred compositions of the invention, relative weight ratio of herbicide A to herbicide B+herbicide the herbicide C comprises or in particular is a mixture of an C.4+herbicide C.6+herbicide C.8 is preferably in the range VLCFA inhibitor, in particular an oxyacetamide and/or a from 1500:1 to 1:50 and more preferably from 500:1 to 1:30. chloroacetamide, and at least one HPPD inhibitor (embodi 0400. In further preferred compositions of the invention, ment 8.8). the herbicide C comprises or in particular is a mixture of an 0388. In the preferred compositions of the embodiment VLCFA inhibitor, in particular an oxyacetamide and/or a 8.8 the HPPD inhibitor heribicide is select from the group of chloroacetamide, and at least one herbicide of the group of toprameZone, tembotrione, isoxaflutole, mesotrione and Sul microtubulin inhibitors (embodiment 8.10). cotrione or a salt thereof. 04.01. In the preferred compositions of the embodiment 0389. In the preferred compositions of the embodiment 8.10 the MTA inhibitor herbicide (herbicide C.7) is select 8.8 the chloroacetamide herbicide is preferably selected from from the group of dinitroanilines, in particularpendimethalin. acetochlor, dimethachlor, dimethenamid, dimethenamid-P, metaZachlor, metolachlor, S-metolachlor, pethoxamide and 0402. In the preferred compositions of the embodiment propisochlor. In these preferred compositions the oxyaceta 8.10 the chloroacetamide herbicide is preferably selected mide herbicide is preferably flufenacet. from acetochlor, dimethachlor, dimethenamid, dimethena 0390. In the embodiment 8.8 the relative weight ratio of mid-P, metaZachlor, metolachlor, S-metolachlor, pethoxam pyroxasulfone and herbicide C.4+C.8 is preferably from ide and propisochlor. In these preferred compositions the 200:1 to 1:200 and more preferably from 100:1 to 1:100. The oxyacetamide herbicide is preferably flufenacet. relative weight ratio of herbicide A to herbicide B+herbicide 0403. In the embodiment 8.10 the relative weight ratio of C.4+herbicide C.8 is preferably in the range from 1500:1 to pyroxasulfone and herbicide C.7+C.8 is preferably from 1:20 and more preferably from 1000:1 to 1:10. 500:1 to 1:500 and more preferably from 250:1 to 1:250. The 0391. In further preferred compositions of the invention, relative weight ratio of herbicide A to herbicide B+herbicide the herbicide C comprises or in particular is a mixture of an C.7+herbicide C.8 is preferably in the range from 1500:1 to VLCFA inhibitor, in particular an oxyacetamide and/or a 1:50 and more preferably from 1000:1 to 1:30. chloroacetamide, at least one HPPD inhibitor herbicide C.4 04.04. In further preferred compositions of the invention, and at least one PSII inhibitor, in particular selected from the the herbicide C comprises or in particular is a mixture of an groups C.6.1, C.6.2. C.6.3 and C.6.8 (embodiment 8.9). imidazolinone herbicide or a salt thereof and at least one PSII 0392. In the preferred compositions of the embodiment inhibitor, in particular selected from the groups C.6.1, C.6.2, 8.9 the HPPD inhibitor heribicide is select from the group of C.6.3 and C.6.8 (embodiment 9). toprameZone, tembotrione, isoxaflutole, mesotrione and Sul 0405. In the preferred compositions of the embodiment 9 cotrione or a salt thereof. the imidazolinone herbicide is preferably selected from 0393. In the preferred compositions of the embodiment imaZamox, imaZapic, imazapyr, imaZaquin, imaZethapyr. 8.9 the chloroacetamide herbicide is preferably selected from their salts and their esters, as well as mixtures thereof, in acetochlor, dimethachlor, dimethenamid, dimethenamid-P, particular imaZamox, imazapic, imazapyr and imazethapyr, metaZachlor, metolachlor, S-metolachlor, pethoxamide and their salts and their esters, as well as mixtures thereof, in propisochlor. In these preferred compositions the oxyaceta particular mixtures of imaZamox with imazapyr and/or mide herbicide is preferably flufenacet. imazethapyr and mixtures of imazapic with imazapyr and/or 0394. In the preferred compositions of the embodiment imazethapyr. 8.9 the PSII-inhibitor is preferably selected from atrazine, 0406. In the preferred compositions of the embodiment 9 terbuthylazin, ametryn, hexazinone, metribuzin, diuron, iso the PSII-inhibitor is preferably selected from atrazine, ter proturon and terbuthiuron. buthylazin, ametryn, hexaZinone, metribuzin, diuron, isopro 0395. In particular preferred compositions of this embodi turOn. ment 8.9, the herbicide C comprises or in particular is a 0407. In the embodiment 9 the relative weight ratio of mixture of dimethenamid-P, at least one PSII inhibitor pyroxasulfone and herbicide C.1.1+C.6 is preferably from selected from atrazine, metribuzine and terbuthylazine, and a 500:1 to 1:500 and more preferably from 250:1 to 1:250. The HPPD inhibitor herbicide, in particular toprameZone. relative weight ratio of herbicide A to herbicide B+herbicide US 2011/0065579 A1 Mar. 17, 2011

C.1.1+herbicide C.6 is preferably in the range from 1000:1 to compound of the formula C.2.6, wherein the variable Y is S. 1:50 and more preferably from 500:1 to 1:30. R’ is fluorine, R is propargyl, R is methyl and R is 0408. In further preferred compositions of the invention, methyl. the herbicide C comprises or in particular is a mixture of an 0422. In other preferred compositions of the embodiment HPPD-inhibitor herbicide or a salt thereof and at least one 11 the PPO inhibitor herbicide is select from the group of PSII inhibitor, in particular selected from the groups C.6.1, dicarboxamide herbicides of the formulae C.2.7, in particular C.6.2. C.6.3 and C.6.8 (embodiment 10). the compound of the formula C.2.7a. 04.09. In the preferred compositions of the embodiment 10 0423. In the embodiment 11 the relative weight ratio of the HPPD-inhibitor herbicide is preferably selected from pyroxasulfone and herbicide C.1.1+C.2 is preferably from isoxaflutole, mesotrione, tembotrione, Sulcotrione and tro 500:1 to 1:500 and more preferably from 250:1 to 1:250. The pameZone, their salts, as well as mixtures thereof. relative weight ratio of herbicide A to herbicide B+herbicide 0410. In the preferred compositions of the embodiment 9 C.1.1+herbicide C.2 is preferably in the range from 1000:1 to the PSII-inhibitor is preferably selected from atrazine, ter 1:50 and more preferably from 500:1 to 1:30. buthylazin, ametryn, hexaZinone, metribuzin, diuron, isopro 0424. In further preferred compositions of the invention, turOn. the herbicide C comprises or in particular is a mixture of an 0411. In the embodiment 10 the relative weight ratio of auxin herbicide or a salt thereof (herbicide C.3) and at least pyroxasulfone and herbicide C.4+C.6 is preferably from one protoporphyrinogen oxidase inhibitor, in particular 500:1 to 1:500 and more preferably from 250:1 to 1:250. The selected from the groups C.2.1, C.2.2, C.2.5. C.2.6 and C.2.7 relative weight ratio of herbicide A to herbicide B+herbicide (embodiment 12). C.4+herbicide C.8 is preferably in the range from 1000:1 to 0425. In the preferred compositions of the embodiment 12 1:50 and more preferably from 500:1 to 1:30. the auxin herbicide is a benzoic acid herbicide of the group 0412. In further preferred compositions of the invention, C.3.1 such as dicamba or a salt thereof, or of the group C.3.2 the herbicide C comprises or in particular is a mixture of an Such as quinmerac or a salt thereof. ALS-inhibitor herbicide, in particular an imidazolinone her 0426 In the preferred compositions of the embodiment 12 bicide or a salt thereof and at least one protoporphyrinogen the PPO inhibitor heribicide is select from the group of pyri oxidase inhibitor, in particular selected from the groups C.2.1 midinedione herbicides, in particular saflufenacil or a salt and C.2.2, C.2.5. C.2.6 and C.2.7 (embodiment 11). thereof. 0413. In the preferred compositions of the embodiment 11 0427. In other preferred compositions of the embodiment the imidazolinone herbicide is preferably selected from 12 the PPO inhibitor herbicide is select from the group of imaZamox, imaZapic, imazapyr, imaZaquin, imaZethapyr. pyrimidinedioneherbicides of the formulae C.2.1b or C.2.1 c. their salts and their esters, as well as mixtures thereof, in in particular the compound of the formula C.2.1 b, wherein R particular imaZamox, imazapic, imazapyr and imazethapyr, is fluorine, R is chlorine, R is methyl and R is cyclopro their salts and their esters, as well as mixtures thereof, in pylmethyl, and the compound of the formula C.2.1c, wherein particular mixtures of imaZamox with imazapyr and/or R’ is fluorine, R is chlorine, R is methyl and R is trifluo imazethapyr and mixtures of imazapic with imazapyr and/or romethyl imazethapyr. 0428. In other preferred compositions of the embodiment 0414. In the preferred compositions of the embodiment 11 12 the PPO inhibitor herbicide is select from the group of the PPO inhibitor herbicide is select from the group of pyri pyrazole herbicides of the formulae C.2.5, in particular com midinedione herbicides, in particular saflufenacil or a salt pounds of the formula Csa, and more preferably the com thereof. pounds of the formula C.2.5a, wherein 0415. In other preferred compositions of the embodiment 0429 R is fluorine, R is chlorine, R is methyl, R is 11 the PPO inhibitor herbicide is select from the group of difluoromethoxy, R is chlorine and R is ethyl, pyrimidinedioneherbicides of the formulae C.2.1b or C.2.1c, 0430 R is chlorine, R is chlorine, R is methyl, R is in particular the compound of the formula C.2.1 b, wherein R difluoromethoxy, R is chlorine and R is ethyl, is fluorine, R is chlorine, R is methyl and R is cyclopro 0431) R' is fluorine, R is chlorine, R is methyl, R is pylmethyl, and the compound of the formula C.2.1c, wherein difluoromethoxy, R is bromine and R is ethyl, or R’ is fluorine, R is chlorine, R is methyl and R' is trifluo 0432 R is chlorine, R is chlorine, R is methyl, R is romethyl difluoromethoxy, R is bromine and R is ethyl. 0416) In other preferred compositions of the embodiment 0433. In other preferred compositions of the embodiment 11 the PPO inhibitor herbicide is select from the group of 12 the PPO inhibitor herbicide is select from the group of pyrazole herbicides of the formulae C.2.5, in particular com triazindioneherbicides of the formulae C.2.6, in particular the pounds of the formula Csa, and more preferably the com compound of the formula C.2.6, wherein the variable Y is S. pounds of the formula C.2.5a, wherein R’ is fluorine, R is propargyl, R is methyl and R is 0417 R is fluorine, R is chlorine, R is methyl, R is methyl. difluoromethoxy, R is chlorine and R is ethyl, 0434 In other preferred compositions of the embodiment 0418 R is chlorine, R is chlorine, R is methyl, R is 12 the PPO inhibitor herbicide is select from the group of difluoromethoxy, R is chlorine and R is ethyl, dicarboxamide herbicides of the formulae C.2.7, in particular 0419 R is fluorine, R is chlorine, R is methyl, R is the compound of the formula C.2.7a. difluoromethoxy, R is bromine and R is ethyl, or 0435. In the embodiment 12 the relative weight ratio of 0420 R is chlorine, R is chlorine, R is methyl, R is pyroxasulfone and herbicide C.1.1+C.2 is preferably from difluoromethoxy, R is bromine and R is ethyl. 500:1 to 1:500 and more preferably from 250:1 to 1:250. The 0421. In other preferred compositions of the embodiment relative weight ratio of herbicide A to herbicide B+herbicide 11 the PPO inhibitor herbicide is select from the group of C.1.1+herbicide C.2 is preferably in the range from 1000:1 to triazindioneherbicides of the formulae C.2.6, in particular the 1:50 and more preferably from 500:1 to 1:30. US 2011/0065579 A1 Mar. 17, 2011

0436. In further preferred compositions of the invention, 0450. In further preferred compositions of the invention, the herbicide C comprises or in particular is a mixture of an the herbicide C comprises or in particular is a mixture of an PPO inhibitor, in particular of the groups C.2.1 and/or C.2.2 PDS inhibitor, in particular an pyridinecarboxamide herbi and/or C.2.5 and/or C.2.5 and/or C.2.7 and at least one PSII cide, and at least one herbicide of the group of microtubulin inhibitor, in particular selected from the groups C.6.1, C.6.2, inhibitors (embodiment 14). C.6.3 and C.6.8 and optionally one or more auxin herbicides 0451. In the preferred compositions of the embodiment 14 C.3, in particular a herbicide of the groups C.3.1, C.3.2 and/or the MTA inhibitor heribicide (herbicide C.7) is select from C.3.4. (embodiment 13). the group of dinitroanilines, in particular pendimethalin. 0437. In the preferred compositions of the embodiment 13 0452. In the preferred compositions of the embodiment 14 the PPO inhibitor herbicide is select from the group of pyri the PDS herbicide is selected from the group of pyridinecar midinedione herbicides, in particular saflufenacil or a salt boxamide herbicides, in particular from flufenican, diflufeni thereof. can and picolinafen, more preferably picolinafen. 0438. In other preferred compositions of the embodiment 0453. In the embodiment 14 the relative weight ratio of 13 the PPO inhibitor herbicide is select from the group of pyroxasulfone and herbicide C.5+C.7 is preferably from pyrimidinedioneherbicides of the formulae C.2.1b or C.2.1c, 200:1 to 1:200 and more preferably from 100:1 to 1:100. The in particular the compound of the formula C.2.1 b, wherein R relative weight ratio of herbicide A to herbicide B+herbicide is fluorine, R is chlorine, R is methyl and R is cyclopro C.7+herbicide C.5 is preferably in the range from 1000:1 to pylmethyl, and the compound of the formula C.2.1c, wherein 1:50 and more preferably from 500:1 to 1:30. R’ is fluorine, R is chlorine, R is methyl and R is trifluo 0454. In further preferred compositions of the invention, romethyl the herbicide C comprises or in particular is a mixture of 0439. In other preferred compositions of the embodiment HPPD-inhibitor herbicide and at least one protoporphyrino 13 the PPO inhibitor herbicide is select from the group of gen oxidase inhibitor, in particular selected from the groups pyrazole herbicides of the formulae C.2.5, in particular com C.2.1 and C.2.2, C.2.5. C.2.6 and C.2.7 (embodiment 15). pounds of the formula Csa, and more preferably the com 0455. In the preferred compositions of the embodiment 15 pounds of the formula C.2.5a, wherein the HPPD-inhibitor herbicide is selected from the group of 0440 R is fluorine, R is chlorine, R is methyl, R is toprameZone, tembotrione, isoxaflutole, mesotrione and Sul difluoromethoxy, R is chlorine and R is ethyl, cotrione and the salts thereof. 0441 R is chlorine, R is chlorine, R is methyl, R is 0456. In the preferred compositions of the embodiment 15 difluoromethoxy, R is chlorine and R is ethyl, the PPO inhibitor herbicide is select from the group of pyri 0442 R is fluorine, R is chlorine, R is methyl, R is midinedione herbicides, in particular saflufenacil or a salt difluoromethoxy, R is bromine and R is ethyl, or thereof. 0443 R’ is chlorine, R is chlorine, R is methyl, R is 0457. In other preferred compositions of the embodiment difluoromethoxy, R is bromine and R is ethyl. 15 the PPO inhibitor herbicide is select from the group of 0444. In other preferred compositions of the embodiment pyrimidinedioneherbicides of the formulae C.2.1b or C.2.1 c. 13 the PPO inhibitor herbicide is select from the group of in particular the compound of the formula C.2.1b, wherein R triazindioneherbicides of the formulae C.2.6, in particular the is fluorine, R is chlorine, R is methyl and R is cyclopro compound of the formula C.2.6, wherein the variable Y is S. pylmethyl, and the compound of the formula C.2.1 c. R’ is fluorine, R is propargyl, R is methyl and R is 0458 wherein R is fluorine, R is chlorine, R is methyl methyl. and R is trifluoromethyl 0445. In other preferred compositions of the embodiment 0459. In other preferred compositions of the embodiment 13 the PPO inhibitor herbicide is select from the group of 15 the PPO inhibitor herbicide is select from the group of dicarboxamide herbicides of the formulae C.2.7, in particular pyrazole herbicides of the formulae C.2.5, in particular com the compound of the formula C.2.7a. pounds of the formula Csa, and more preferably the com 0446. In the preferred compositions of the embodiment 13 pounds of the formula C.2.5a, wherein the PSII-inhibitor is preferably selected from atrazine, ter 0460 R is fluorine, R is chlorine, R is methyl, R is buthylazin, ametryn, hexaZinone, metribuzin, diuron, isopro difluoromethoxy, R is chlorine and R is ethyl, turOn. 0461) R' is chlorine, R is chlorine, R is methyl, R is 0447. In the preferred compositions of the embodiment 13 difluoromethoxy, R is chlorine and R is ethyl, the optional auxin herbicide C.3 is at least one benzoic acid 0462 R is fluorine, R is chlorine, R is methyl, R is herbicide of the group C.3.1, such as dicamba or a salt thereof, difluoromethoxy, R is bromine and R is ethyl, or or quinolinecarboxylic acid herbicide of the group C.3.2 such 0463 R’ is chlorine, R is chlorine, R is methyl, R is as quinmerac or a salt thereof. difluoromethoxy, R is bromine and R is ethyl. 0448. In particular preferred compositions of this embodi 0464. In other preferred compositions of the embodiment ment 13, the herbicide C comprises or in particular is a mix 15 the PPO inhibitor herbicide is select from the group of ture of saflufenacil, at least one PSII inhibitor selected from triazindioneherbicides of the formulae C.2.6, in particular the atrazine, metribuzine and terbuthylazine, and an auxin herbi compound of the formula C.2.6, wherein the variable Y is S. cide, in particular a benzoic acid herbicide Such as dicamba. R’ is fluorine, R is propargyl, R is methyl and R is 0449 In the embodiment 13 the relative weight ratio of methyl. pyroxasulfone and herbicide C.2+C.6 or C.2+C.6+C.3 is 0465. In other preferred compositions of the embodiment preferably from 500:1 to 1:500 and more preferably from 15 the PPO inhibitor herbicide is select from the group of 250:1 to 1:250. The relative weight ratio of herbicide A to dicarboxamide herbicides of the formulae C.2.7, in particular herbicide B+herbicide C.2+herbicide C.6 or herbicide C.2+ the compound of the formula C.2.7a. herbicide C.3+herbicide C.6 is preferably in the range from 0466. In the embodiment 15 the relative weight ratio of 1000:1 to 1:50 and more preferably from 500:1 to 1:30. pyroxasulfone and herbicide C.4+C.2 is preferably from US 2011/0065579 A1 Mar. 17, 2011 20

500:1 to 1:500 and more preferably from 250:1 to 1:250. The 0480. In the preferred compositions of the embodiment 17 relative weight ratio of herbicide A to herbicide B+herbicide are selected from the group consisting of chloroacetamide C.1.1+herbicide C.2 is preferably in the range from 1000:1 to herbicides (embodiment 17.1), in particular acetochlor, 1:50 and more preferably from 500:1 to 1:30. dimethachlor, dimethenamid, dimethenamid-P metaZachlor, 0467. In further preferred compositions of the invention, propisochlor, pethoxamide, metolachlor, and metolachlor-S the herbicide C comprises or in particular is a mixture of and oxyacetamide herbicides (embodiment 17.2), in particu microtubulin-inhibitor herbicide and at least one protopor lar flufenacet. phyrinogen oxidase inhibitor, in particular selected from the 0481. In the compositions of the embodiment 17 (and groups C.2.1 and C.2.2, C.2.5. C.2.6 and C.2.7 (embodiment likewise in embodiments 17.1 and 17.2) the relative weight 16). ratio of pyroxasulfone to herbicide C.8 is preferably in the 0468. In the preferred compositions of the embodiment 16 range from 1:250 to 250:1, in particular in the range of 1:200 the microtubulin-inhibitor herbicide is selected from the to 200:1 and more preferably from 150:1 to 1:150. The rela group of dinitroaniline herbicides, in particular selected from tive weight ratio of herbicide A to herbicide B+herbicide C.8 the group of benfluralin, butralin, dinitramine, ethal fluralin, is preferably in the range from 1500:1 to 1:20 and more fluchloralin, isopropalin, methalpropalin, nitralin, oryzalin, preferably from 1000:1 to 1:10. pendimethalin, prodiamine, profluralin and trifluralin, more 0482 In particular preferred compositions of this embodi preferably selected from the group of oryzalin, pendimethalin ment 17.1, the herbicide C comprises or in particular is and trifluralin. acetochlor. 0469. In the preferred compositions of the embodiment 16 0483. In other particular preferred compositions of this the PPO inhibitor herbicide is select from the group of pyri embodiment 17.1, the herbicide C comprises or in particular midinedione herbicides, in particular saflufenacil or a salt is dimethachlor. thereof. 0484. In further particular preferred compositions of this 0470. In other preferred compositions of the embodiment embodiment 17.1, the herbicide C comprises or in particular 16 the PPO inhibitor herbicide is select from the group of is dimethenamid. pyrimidinedioneherbicides of the formulae C.2.1b or C.2.1c, 0485. In further particular preferred compositions of this in particular the compound of the formula C.2.1 b, wherein R embodiment 17.1, the herbicide C comprises or in particular is fluorine, R is chlorine, R is methyl and R is cyclopro is dimethenamid-P. pylmethyl, and the compound of the formula C.2.1c, wherein 0486 In further particular preferred compositions of this R’ is fluorine, R is chlorine, R is methyl and R is trifluo embodiment 17.1, the herbicide C comprises or in particular romethyl. is metaZachlor. 0471. In other preferred compositions of the embodiment 0487. In further particular preferred compositions of this 16 the PPO inhibitor herbicide is select from the group of embodiment 17.1, the herbicide C comprises or in particular pyrazole herbicides of the formulae C.2.5, in particular com is propisochlor. pounds of the formula Csa, and more preferably the com 0488. In further particular preferred compositions of this pounds of the formula C.2.5a, wherein embodiment 17.2, the herbicide C comprises or in particular 0472 R is fluorine, R is chlorine, R is methyl, R is is flufenacet. difluoromethoxy, R is chlorine and R is ethyl, 0489. In the preferred compositions of the embodiment 17 0473 R’ is chlorine, R is chlorine, R is methyl, R is the PPO inhibitor herbicide is select from the group of pyri difluoromethoxy, R is chlorine and R is ethyl, midinedione herbicides, in particular saflufenacil or a salt 0474 R is fluorine, R is chlorine, R is methyl, R is thereof. difluoromethoxy, R is bromine and R is ethyl, or 0490. In other preferred compositions of the embodiment 0475 R is chlorine, R is chlorine, R is methyl, R is 17 the PPO inhibitor herbicide is select from the group of difluoromethoxy, R is bromine and R is ethyl. pyrimidinedioneherbicides of the formulae C.2.1b or C.2.1 c. 0476. In other preferred compositions of the embodiment in particular the compound of the formula C.2.1b, wherein R 16 the PPO inhibitor herbicide is select from the group of is fluorine, R is chlorine, R is methyl and R is cyclopro triazindioneherbicides of the formulae C.2.6, in particular the pylmethyl, and the compound of the formula C.2.1c, wherein compound of the formula C.2.6, wherein the variable Y is S. R’ is fluorine, R is chlorine, R is methyl and R is trifluo R’ is fluorine, R is propargyl, R is methyl and R is romethyl. methyl. 0491. In other preferred compositions of the embodiment 0477. In other preferred compositions of the embodiment 17 the PPO inhibitor herbicide is select from the group of 16 the PPO inhibitor herbicide is select from the group of pyrazole herbicides of the formulae C.2.5, in particular com dicarboxamide herbicides of the formulae C.2.7, in particular pounds of the formula Csa, and more preferably the com the compound of the formula C.2.7a. pounds of the formula C.2.5a, wherein 0478. In the embodiment 16 the relative weight ratio of 0492 R is fluorine, R is chlorine, R is methyl, R is pyroxasulfone and herbicide C.7+C.2 is preferably from difluoromethoxy, R is chlorine and R is ethyl, 500:1 to 1:500 and more preferably from 250:1 to 1:250. The 0493 R’ is chlorine, R is chlorine, R is methyl, R is relative weight ratio of herbicide A to herbicide B+herbicide difluoromethoxy, R is chlorine and R is ethyl, C.1.1+herbicide C.2 is preferably in the range from 1000:1 to 0494 R is fluorine, R is chlorine, R is methyl, R is 1:50 and more preferably from 500:1 to 1:30. difluoromethoxy, R is bromine and R is ethyl, or 0479. In further preferred compositions of the invention, 0495 R is chlorine, R is chlorine, R is methyl, R is the herbicide C comprises or in particular is a mixture of difluoromethoxy, R is bromine and R is ethyl. VLCFA inhibitor herbicide and at least one protoporphyrino 0496. In other preferred compositions of the embodiment gen oxidase inhibitor, in particular selected from the groups 17 the PPO inhibitor herbicide is select from the group of C.2.1 and C.2.2, C.2.5. C.2.6 and C.2.7 (embodiment 16). triazindioneherbicides of the formulae C.2.6, in particular the US 2011/0065579 A1 Mar. 17, 2011 21 compound of the formula C.2.6, wherein the variable Y is S. 0500. In further particular preferred compositions of this R’ is fluorine, R is propargyl, R is methyl and R is embodiment 17.3, the herbicide C comprises or in particular methyl. is a mixture of PPO inhibitor, quinmerac or a salt thereof and 0497. In other preferred compositions of the embodiment metaZachlor. 17 the PPO inhibitor herbicide is select from the group of 0501. In further particular preferred compositions of this dicarboxamide herbicides of the formulae C.2.7, in particular the compound of the formula C.2.7a. embodiment 17.3, the herbicide C comprises or in particular 0498. In the embodiment 17 the relative weight ratio of is a mixture of PPO inhibitor, dicamba or a salt thereof and pyroxasulfone and herbicide C.7+C.2 is preferably from metaZachlor. 500:1 to 1:500 and more preferably from 250:1 to 1:250. The 0502. In further particular preferred compositions of this relative weight ratio of herbicide A to herbicide B+herbicide embodiment 17.3, the herbicide C comprises or in particular C.1.1+herbicide C.2 is preferably in the range from 1000:1 to is a mixture of PPO inhibitor, dicamba or a salt thereof and 1:50 and more preferably from 500:1 to 1:30. flufenacet. 0499. In further preferred compositions of this embodi 0503. In further particular preferred compositions of this ment 17, the composition additionally contains at least one embodiment 17.3, the herbicide C comprises or in particular herbicides of the group C.3, in particular of the group C.3.1 is a mixture of PPO inhibitor, dicamba or a salt thereof and Such as dicamba or a salt thereof, or of the group C.3.2 Such dimethenamid-P, optionally comprising a PSII inhibitor her as quinmerac or a salt thereof (embodiment 17.3) and/or bicide Such as atrazine or metribuzin. clomazone (embodiment 17.4). In these preferred composi 0504. In further particular preferred compositions of this tions of the embodiments 17.3 and 17.4 the VLCFA-inhibitor embodiment 17.4, the herbicide C comprises or in particular is preferably selected from chloroacetamide herbicides, in is a mixture of PPO inhibitor, clomazone and metazachlor. particular selected from acetochlor, dimethachlor, dimeth 0505. In further particular preferred compositions of this enamid, dimethenamid-P, metaZachlor, metolachlor, S-meto embodiment 8.4, the herbicide C comprises or in particular is lachlor, pethoxamide and propisochlor. In these preferred a mixture of PPO inhibitor, clomazone and dimethenamid-P. compositions the oxyacetamide herbicide is preferably 0506 Examples of suitable compositions are given in the flufenacet. following table 1:

erbicide A:(B+C) NO. : Herbicide B Herbicide C* B:C Wiw ww

ypnosate pyroxaSuIIone — 2OOO:1-1:10 ufosinate pyroxasulfone — 2OOO:1-1:10 ypnosate pyroxasulfone imaZamox SOO:1-1:500 SOO:1-1:20 ufosinate pyroxasulfone imaZamox SOO:1-1:500 SOO:1-1:20 ypnosate pyroxasulfone imazapyr SOO:1-1:500 SOO:1-1:20 ufosinate pyroxasulfone imazapyr SOO:1-1:500 SOO:1-1:20 ypnosate pyroxasulfone imazapic SOO:1-1:500 SOO:1-1:20 ufosinate pyroxasulfone imazapic SOO:1-1:500 SOO:1-1:20 ypnosate pyroxasulfone imazethalpyr SOO:1-1:500 SOO:1-1:20 ufosinate pyroxasulfone imazethalpyr SOO:1-1:500 SOO:1-1:20 ypnosate pyroxasulfone imaZamox + SOO:1-1:500 SOO:1-1:20 imazethalpyr ufosinate pyroxasulfone imaZamox + SOO:1-1:500 SOO:1-1:20 imazethalpyr ypnosate pyroxasulfone imaZamox + SOO:1-1:500 SOO:1-1:20 imazapyr ufosinate pyroxasulfone imaZamox + SOO:1-1:500 SOO:1-1:20 imazapyr ypnosate pyroxasulfone imazapic + SOO:1-1:500 SOO:1-1:20 imazethalpyr ufosinate pyroxasulfone imazapic + SOO:1-1:500 SOO:1-1:20 imazethalpyr ypnosate pyroxasulfone imazapic + SOO:1-1:500 SOO:1-1:20 imazapyr 8 9. ufosinate pyroxasulfone imazapic + SOO:1-1:500 SOO:1-1:20 imazapyr ypnosate pyroxasulfone saflufenacil 100:1-1:100 OOO:1-1:10 2O ufosinate pyroxasulfone saflufenacil 100:1-1:100 OOO:1-1:10 21 ypnosate pyroxasulfone butafenacil 100:1-1:100 OOO:1-1:10 22 ufosinate pyroxasulfone butafenacil 100:1-1:100 OOO:1-1:10 23 ypnosate pyroxasulfone flumioxazin 100:1-1:100 OOO:1-1:10 24 ufosinate pyroxasulfone flumioxazin 100:1-1:100 OOO:1-1:10 25 ypnosate pyroxasulfone flumiclorac 100:1-1:100 OOO:1-1:10 26 ufosinate pyroxasulfone flumiclorac 100:1-1:100 OOO:1-1:10 27 ypnosate pyroxasulfone flumipropyn 100:1-1:100 OOO:1-1:10 28 ufosinate pyroxasulfone flumipropyn 100:1-1:100 OOO:1-1:10 29 ypnosate pyroxasulfone dicamba 2SO:1-1:250 OOO:1-1:10 30 ufosinate pyroxasulfone dicamba 2SO:1-1:250 OOO:1-1:10 31 ypnosate pyroxasulfone 2,4-D SOO:1-1:500 OOO:1-1:10 32 ufosinate pyroxasulfone 2,4-D SOO:1-1:500 OOO:1-1:10 US 2011/0065579 A1 Mar. 17, 2011 22

-continued

e bicide No. Herbicide B Herbicide C* B:C Wiw

33 OS8. pyroxasu Ole toprameZone 100:1-1:100 :20 34 osina pyroxasu Ole toprameZone 100:1-1:100 :20 35 OS8. pyroxasu Ole isoxaflutole 100:1-1:100 :20 36 osina pyroxasu Ole isoxaflutole 100:1-1:100 :20 37 OS8. pyroxasu Ole mesotrione 100:1-1:100 :20 38 osina pyroxasu Ole mesotrione 100:1-1:100 :20 39 OS8. pyroxasu Ole Sulcotrione 100:1-1:100 :20 40 osina pyroxasu Ole Sulcotrione 100:1-1:100 :20 41 OS8. pyroxasu Ole flufenican 100:1-1:100 :20 42 osina pyroxasu Ole flufenican 100:1-1:100 :20 43 OS8. pyroxasu Ole diflufenican 100:1-1:100 :20 44 osina pyroxasu Ole diflufenican 100:1-1:100 :20 45 OS8. pyroxasu Ole icolinafen 100:1-1:100 :20 46 osina pyroxasu Ole picolinafen 100:1-1:100 :20 47 OS8. pyroxasu Ole 8.trazine SOO:1-1:500 :20 48 osina pyroxasu Ole 8.trazine SOO:1-1:500 :20 49 OS8. pyroxasu Ole metribuzin SOO:1-1:500 :20 50 osina pyroxasu Ole metribuzin SOO:1-1:500 :20 51 OS8. pyroxasu Ole terbuthylazine SOO:1-1:500 :20 52 osina pyroxasu Ole terbuthylazine SOO:1-1:500 :20 53 OS8. pyroxasu Ole ametryn SOO:1-1:500 :20 S4 osina pyroxasu Ole ametryn SOO:1-1:500 :20 55 OS8. pyroxasu Ole hexazinone SOO:1-1:500 :20 56 osina pyroxasu Ole hexazinone SOO:1-1:500 :20 57 OS8. pyroxasu Ole diuron SOO:1-1:500 :20 58 osina pyroxasu Ole diuron SOO:1-1:500 :20 59 OS8. pyroxasu Ole isoproturon SOO:1-1:500 :20 60 osina pyroxasu Ole isoproturon SOO:1-1:500 :20 61 OS8. pyroxasu Ole atrazine + SOO:1-1:500 :20 ametryn 62 9. osina pyroxasu Ole atrazine + SOO:1-1:500 :20 ametryn 63 9. y OS8. pyroxasu Ole atrazine + SOO:1-1:500 :20 metribuzin 64 9. l osina pyroxasu Ole atrazine + SOO:1-1:500 :20 metribuzin

65 OS8. pyroxasu Ole endimethalin 100:1-1:500 :100 66 osina pyroxasu Ole pendimethalin 100:1-1:500 :100 67 OS8. pyroxasu Ole O ry Zalin 100:1-1:500 :100 68 osina pyroxasu Ole O ry Zalin 100:1-1:500 :100 69 OS8. pyroxasu Ole 8. cetochlor 2SO:1-1:250 :20 70 osina pyroxasu Ole 8. cetochlor 2SO:1-1:250 :20 71 OS8. pyroxasu Ole imethenamid 2SO:1-1:250 :20 72 osina pyroxasu Ole imethenamid 2SO:1-1:250 :20 73 OS8. pyroxasu Ole imethenamid-P 2SO:1-1:250 :20 74 osina pyroxasu Ole imethenamid-P 2SO:1-1:250 :20 75 OS8. pyroxasu Ole imethachlor 2SO:1-1:250 :20 76 osina pyroxasu Ole imethachlor 2SO:1-1:250 :20 77 OS8. pyroxasu Ole metaZachlor 2SO:1-1:250 :20 78 osina pyroxasu Ole metaZachlor 2SO:1-1:250 :20 79 OS8. pyroxasu Ole ropisochlor 2SO:1-1:250 :20 8O osina pyroxasu Ole ropisochlor 2SO:1-1:250 :20 81 OS8. pyroxasu Ole ufenacet 2SO:1-1:250 :20 82 osina pyroxasu Ole ufenacet 2SO:1-1:250 :20 83 OS8. pyroxasu Ole uinmerac + SOO:1-1:500 :50 metaZachlor 84 9. l osina pyroxasu Ole uinmerac + SOO:1-1:500 :50 metaZachlor 85 9. OS8. pyroxasu Ole uinmerac + SOO:1-1:500 :50 ufenacet 86 ufosina pyroxasu Ole uinmerac + SOO:1-1:500 OOO:1- :50 ufenacet 87 OS8. pyroxasu Ole icamba + SOO:1-1:500 OOO:1- :50 ufenacet 88 ufosina pyroxasu Ole icamba + SOO:1-1:500 OOO:1- :50 ufenacet 89 OS8. pyroxasu Ole metribuzin + SOO:1-1:500 OOO:1- :50 ufenacet 90 ufosina pyroxasu Ole metribuzin + SOO:1-1:500 OOO:1- :50 ufenacet 91 OS8. pyroxasu Ole 8.trazine + SOO:1-1:500 OOO:1- :50 ufenacet

US 2011/0065579 A1 Mar. 17, 2011 27

-continued

Herbicide No. A: Herbicide B Herbicide C* B:C Wiw

204 glu osinate pyroxasu Ole imazapic + SOO:1-1:500 OOO:1-1:SO imazethalpyr + terbuthylazine 205 phosate pyroxasu Ole imazapic + SOO:1-1:500 OOO:1-1:SO imazapyr + terbuthylazine osinate pyroxasu Ole imazapic + SOO:1-1:500 OOO:1-1:SO imazapyr + terbuthylazine OS86 pyroxasu Ole isoxaflutole + SOO:1-1:500 OOO:1-1:SO atrazine 208 osinate pyroxasu Ole isoxaflutole + SOO:1-1:500 OOO:1-1:SO atrazine 209 OS86 pyroxasu Ole Sulcotrione + SOO:1-1:500 OOO:1-1:SO atrazine osinate pyroxasu Ole Sulcotrione + SOO:1-1:500 OOO:1-1:SO atrazine OS86 pyroxasu Ole toprameZone + SOO:1-1:500 OOO:1-1:SO atrazine osinate pyroxasu Ole toprameZone + SOO:1-1:500 OOO:1-1:SO atrazine OS86 pyroxasu Ole mesotrione + SOO:1-1:500 OOO:1-1:SO atrazine osinate pyroxasu Ole mesotrione + SOO:1-1:500 OOO:1-1:SO atrazine OS86 pyroxasu Ole tembotrione + SOO:1-1:500 OOO:1-1:SO atrazine osinate pyroxasu Ole tembotrione + SOO:1-1:500 OOO:1-1:SO atrazine OS86 pyroxasu Ole isoxaflutole + SOO:1-1:500 OOO:1-1:SO metribuzin osinate pyroxasu Ole isoxaflutole + SOO:1-1:500 OOO:1-1:SO metribuzin OS86 pyroxasu Ole Sulcotrione + SOO:1-1:500 OOO:1-1:SO metribuzin 220 osinate pyroxasu Ole Sulcotrione + SOO:1-1:500 OOO:1-1:SO metribuzin 221 OS86 pyroxasu Ole toprameZone + SOO:1-1:500 OOO:1-1:SO metribuzin 222 osinate pyroxasu Ole toprameZone + SOO:1-1:500 OOO:1-1:SO metribuzin 223 OS86 pyroxasu Ole mesotrione + SOO:1-1:500 OOO:1-1:SO metribuzin 224 osinate pyroxasu Ole mesotrione + SOO:1-1:500 OOO:1-1:SO metribuzin 225 OS86 pyroxasu Ole tembotrione + SOO:1-1:500 OOO:1-1:SO metribuzin 226 osinate pyroxasu Ole tembotrione + SOO:1-1:500 OOO:1-1:SO metribuzin 227 OS86 pyroxasu Ole isoxaflutole + SOO:1-1:500 OOO:1-1:SO ametryn 228 osinate pyroxasu Ole isoxaflutole + SOO:1-1:500 OOO:1-1:SO ametryn 229 OS86 pyroxasu Ole Sulcotrione + SOO:1-1:500 OOO:1-1:SO ametryn 230 osinate pyroxasu Ole Sulcotrione + SOO:1-1:500 OOO:1-1:SO ametryn 231 OS86 pyroxasu Ole toprameZone + SOO:1-1:500 OOO:1-1:SO ametryn 232 osinate pyroxasu Ole toprameZone + SOO:1-1:500 OOO:1-1:SO ametryn 233 OS86 pyroxasu Ole mesotrione + SOO:1-1:500 OOO:1-1:SO ametryn 234 osinate pyroxasu Ole mesotrione + SOO:1-1:500 OOO:1-1:SO ametryn 235 OS86 pyroxasu Ole tembotrione + SOO:1-1:500 OOO:1-1:SO ametryn 236 osinate pyroxasu Ole tembotrione + SOO:1-1:500 OOO:1-1:SO ametryn 237 OS86 pyroxasu Ole dimethenamid SOO:1-1:500 OOO:1-1:SO P terbuthylazine US 2011/0065579 A1 Mar. 17, 2011 28

-continued

Herbicide No. A: Herbicide B Herbicide C* B:C Wiw

238 glufosinate pyroxasu Ole imethenamid SOO:1-1:500 OOO:1-1:SO erbuthylazine 239 glyphosate pyroxasu Ole imethenamid SOO:1-1:500 OOO:1-1:SO

240 glufosinate pyroxasu Ole SOO:1-1:500 OOO:1-1:SO

241 glyphosate pyroxasu Ole SOO:1-1:500 OOO:1-1:SO

242 glufosinate pyroxasu Ole SOO:1-1:500 OOO:1-1:SO

243 glyphosate pyroxasu Ole imethenamid SOO:1-1:500 OOO:1-1:SO P+ atrazine 244 glufosinate pyroxasu Ole imethenamid SOO:1-1:500 OOO:1-1:SO P+ atrazine 245 glyphosate pyroxasu Ole imethenamid 2OO:1-1:200 OOO:1-1:10 P+ saflufenacil 246 glufosinate pyroxasu Ole imethenamid 2OO:1-1:200 OOO:1-1:10 P+ saflufenacil 247 glyphosate pyroxasu Ole imethenamid SOO:1-1:500 OOO:1-1:SO P+ atrazine + icamba 248 glufosinate pyroxasu Ole imethenamid SOO:1-1:500 OOO:1-1:SO P+ atrazine + icamba 249 glyphosate pyroxasu Ole imethenamid 2OO:1-1:200 SOO:1-1:20

O)8(ZOile 250 glufosinate pyroxasu Ole imethenamid 2OO:1-1:200 SOO:1-1:20 P O)8(ZOile 251 glyphosate pyroxasu Ole imethenamid 200:1-1:500 SOO:1-1:SO P 862Ole -- camba 252 glufosinate pyroxasu Ole methenamid 200:1-1:500 SOO:1-1:SO

862Ole -- camba 253 glyphosate pyroxasu Ole ethenamid 200:1-1:500 SOO:1-1:SO atrazine + O)8(ZOile glufosinate pyroxasu Ole imethenamid 200:1-1:500 SOO:1-1:SO P+ atrazine + O)8(ZOile 255 glyphosate pyroxasu Ole imethenamid 200:1-1:500 SOO:1-1:SO P O)8(ZOle -- erbuthylazine glufosinate pyroxasu Ole imethenamid 200:1-1:500 SOO:1-1:SO P O)8(ZOle -- erbuthylazine 257 glyphOSale pyroxasu Ole saflufenaci + SOO:1-1:500 OOO:1-1:SO imazethalpyr 258 glufosinate pyroxasu Ole saflufenaci + SOO:1-1:500 OOO:1-1:SO imazethalpyr 259 glyphOSale pyroxasu Ole saflufenaci + SOO:1-1:500 OOO:1-1:SO dicamba 260 glufosinate pyroxasu Ole saflufenaci + SOO:1-1:500 OOO:1-1:SO dicamba 261 glyphOSale pyroxasu Ole terbuthylazin+ SOO:1-1:500 OOO:1-1:SO isoxaflutole 262 glufosinate pyroxasu Ole terbuthylazin+ SOO:1-1:500 OOO:1-1:SO isoxaflutole 263 glyphOSale pyroxasu Ole terbuthylazin+ SOO:1-1:500 OOO:1-1:SO Sulcotrione 264 glufosinate pyroxasu Ole terbuthylazin+ SOO:1-1:500 OOO:1-1:SO Sulcotrione glyphOSale pyroxasu Ole terbuthylazin+ SOO:1-1:500 OOO:1-1:SO toprameZone

US 2011/0065579 A1 Mar. 17, 2011 30

-continued Herbicide Herbicide A: (B+C)* No. Herbicide C1 Herbicide C2 C3 C4 B:C* wiw B:C1 B:C2 B:C3 B:C4 ww

317 saflufenacil metazachlor dicamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 318 saflufenacil terbuthiuron dicamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 319 saflufenacil clomazone dicamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 320 saflufenacil hexazinone diuron dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 321 saflufenacil isoxaflutole dicamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 322 compound A — SOO:1-1:SOO SOO:1-1:SOO OOO:1-1:10 323 compound A dimta-P SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 324 compound A dimta-P atrazine dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 325 compound A imazethalpyr SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 326 compound A dicamba SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 327 compound A. atrazine SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 328 compound A pendimethalin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 329 compound A flumioxazin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 330 compound A Sulfentrazone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 331 compound A imazaquin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 332 compound A imazapic SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 333 compound A imazapic imazapyr — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 334 compound A flufenaceet SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 335 compound A chloransulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 336 compound A diclosulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 337 compound A flumetSulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 338 compound A diuron SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 339 compound A metribuzin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 340 compound A hexaZinone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 341 compound A mesotrione SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 342 compound A ametryn SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 343 compound A terbuthylazine SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 344 compound A metaZachlor SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 345 compound A terbuthiuron SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 346 compound A clomazone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 347 compound A hexaZinone iuron SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 348 compound A isoxaflutole SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 349 compound A. atrazine icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 350 compound A pendimethalin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 351 compound A flumioxazin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 352 compound A Sulfentrazone icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 353 compound A imazaquin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 354 compound A imazapic icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 355 compound A imazapic imazapyr dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 356 compound A flufenaceet icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 357 compound A chloransulam icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 358 compound A diclosulam icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 359 compound A flumetSulam icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 360 compound A diuron icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 361 compound A metribuzin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 362 compound A hexaZinone icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 363 compound A mesotrione icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 364 compound A ametryn icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 365 compound A terbuthylazine icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 366 compound A metazachlor icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 367 compound A terbuthiuron icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 368 compound A clomazone icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 369 compound A hexazinone iuron dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 370 compound A isoxaflutole icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 371 compound B — SOO:1-1:SOO SOO:1-1:SOO OOO:1-1:10 372 compound B dimta-P SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 373 compound B dimta-P atrazine dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 374 compound B imazethapyr SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 375 compound B dicamba SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 376 compound B atrazine SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 377 compound B pendimethalin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 378 compound B flumioxazin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 379 compound B Sulfentrazone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 380 compound B imazaquin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 381 compound B imazapic SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 382 compound B imazapic imazapyr — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 383 compound B flufenaceet SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 384 compound B chloransulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 385 compound B diclosulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 386 compound B flumetSulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 387 compound B diuron SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 388 compound B metribuzin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 389 compound B hexazinone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO US 2011/0065579 A1 Mar. 17, 2011 31

-continued Herbicide Herbicide A: (B+C)* No. Herbicide C1 Herbicide C2 C3 C4 B:C* wiw B:C1 B:C2 B:C3 B:C4 ww 390 compound B mesotrione SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 391 compound B ametryn SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 392 compound B terbuthylazine SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 393 compound B metazachlor SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 394 compound B terbuthiuron SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 395 compound B clomazone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 396 compound B hexazinone iuron SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 397 compound B isoxaflutole SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 398 compound B atrazine icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 399 compound B pendimethalin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 400 compound B flumioxazin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 401 compound B sulfentraZone icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 402 compound B imazaquin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 403 compound B imazapic icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 404 compound B imazapic imazapyr dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 405 compound B flufenaceet icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 406 compound B chloransulam icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 407 compound B diclosulam icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 408 compound B flumetSulam icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 409 compound B diuron icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 410 compound B metribuzin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 411 compound B hexazinone icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 412 compound B mesotrione icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 413 compound B ametryn icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 414 compound B terbuthylazine icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 415 compound B metazachlor icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 416 compound B terbuthiuron icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 417 compound B clomazone icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 418 compound B hexazinone iuron dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 419 compound B isoxaflutole icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 420 compound C — SOO:1-1:SOO SOO:1-1:SOO OOO:1-1:10 421 compound C dimta-P SOO:1-1:SOO 450:1-1450 450:1-1:450 OOO:1-1:SO 422 compound C dimta-P atrazine dicamba 500:1-1:500 450:1-1:450 450:1-1:450 450:1-1:450 450:1-1:450 1000:1-1:50 423 compound C imazethalpyr SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 424 compound C dicamba SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 425 compound C atrazine SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 426 compound C pendimethalin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 427 compound C flumioxazin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 428 compound C SulfentraZone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 429 compound C imazaquin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 430 compound C imazapic SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 431 compound C imazapic imazapyr — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 432 compound C flufenaceet SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 433 compound C chloranSulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 434 compound C dicloSulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 435 compound C flumetSulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 436 compound C diuron SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 437 compound C metribuzin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 438 compound C hexazinone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 439 compound C mesotrione SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 440 compound C ametryn SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 441 compound C terbuthylazine SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 442 compound C metaZachlor SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 443 compound C terbuthiuron SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 444 compound C clomazone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 445 compound C hexazinone iuron SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 446 compound C isoxaflutole SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 447 compound C atrazine icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 448 compound C pendimethalin icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 449 compound C flumioxazin icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 450 compound C SulfentraZone icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 451 compound C imazaquin icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 452 compound C imazapic icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 453 compound C imazapic imazapyr dicamba 500:1-1:500 450:1-1:450 450: OOO:1-1:SO 454 compound C flufenaceet icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 455 compound C chloransulam icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 456 compound C diclosulam icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 457 compound C flumetSulam icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 458 compound C diuron icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 459 compound C metribuzin icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 460 compound C hexazinone icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 461 compound C mesotrione icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 462 compound C ametryn icamba — SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO US 2011/0065579 A1 Mar. 17, 2011 32

-continued Herbicide Herbicide A: (B+C)* No. Herbicide C1 Herbicide C2 C3 C4 B:C* wiw B:C1 B:C2 B:C3 B:C4 ww

463 compound C terbuthylazine dicamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 464 compound C metaZachlor dicamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 465 compound C terbuthiuron dicamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 466 compound C clomazone dicamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 467 compound C hexazinone diuron dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 468 compound C isoxaflutole dicamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 469 compound D — SOO:1-1:SOO SOO:1-1:SOO OOO:1-1:10 470 compound D dimta-P SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 471 compound D dimta-P atrazine dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 472 compound D imazethalpyr SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 473 compound D dicamba SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 474 compound D atrazine SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 475 compound D pendimethalin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 476 compound D flumioxazin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 477 compound D SulfentraZone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 478 compound D imazaquin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 479 compound D imazapic SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 480 compound D imazapic imazapyr — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 481 compound D flufenaceet SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 482 compound D chloranSulam SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 483 compound D diclosulam SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 484 compound D flumetSulam SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 485 compound D diuron SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 486 compound D metribuzin SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 487 compound D hexazinone SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 488 compound D mesotrione SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 489 compound D ametryn SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 490 compound D terbuthylazine SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 491 compound D metazachlor SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 492 compound D terbuthiuron SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 493 compound D clomazone SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 494 compound D hexazinone iuron SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 495 compound D isoxaflutole SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 496 compound D atrazine icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 497 compound D pendimethalin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 498 compound D flumioxazin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 499 compound D SulfentraZone icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 500 compound D imazaquin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 501 compound D imazapic icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 502 compound D imazapic imazapyr dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 503 compound D flufenaceet icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 504 compound D chloransulam icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 505 compound D diclosulam icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 506 compound D flumetSulam icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 507 compound D diuron icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 508 compound D metribuzin icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 509 compound D hexazinone icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 510 compound D mesotrione icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 511 compound D ametryn icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 512 compound D terbuthylazine icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 513 compound D metazachlor icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 514 compound D terbuthiuron icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 515 compound D clomazone icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 516 compound D hexazinone iuron dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 517 compound D isoxaflutole icamba — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 518 compound E — SOO:1-1:SOO SOO:1-1:SOO OOO:1-1:SO 519 compound E SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 520 compoun atrazine dicamba 500:1-1:500 450:1-1:450 450: 450:1-1450 450:1-1:4SO 1000:1-1:SO 521 compoun SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 522 compound E dicamba SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 523 compound E atrazine SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 524 compound E pendimethalin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 525 compound E flumioxazin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 526 compound E Sulfentrazone SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 527 compoun imaZaquin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 528 compound E imazapic SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 529 compound E imazapic imazapyr — SOO:1-1:SOO 450:1-1450 450: 450:1-1:450 - OOO:1-1:SO 530 compound E flufenaceet SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 531 compound E chloransulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 532 compound E diclosulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 533 compoun flumetSulam SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 534 compound E diuron SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO 535 compound E metribuzin SOO:1-1:SOO 450:1-1450 450: OOO:1-1:SO

US 2011/0065579 A1 Mar. 17, 2011

-continued Herbicide Herbicide A: (B+C)* No. Herbicide C1 Herbicide C2 C3 C4 B:C* wiw B:C1 B:C2 B:C3 B:C4 ww compoundB; Cl Br

(C) compound D: F O CH3 )- NM O N )- S X-NV N O CH O \ = (D) compound E: O-CH O C1 D v O O N N H H w A HC

HC (E)

Continuation 2 of Table 1: safener or virtually no safener (i.e. less than 1% by weight, based on the total amount of herbicide A and herbicide B). 0508 Mixtures 659 to 1044: These mixtures correspond to 0510 Suitable safeners, which can be used in the compo mixtures 273 to 658, wherein glyphosate has been replaced sitions according to the present invention are known in the art, by gluphosinate or a salt thereof. e.g. from 0509. The compositions of the invention may also com The Compendium of Pesticide Common Names (http://www. prise, as a component d), one or more safeners. Safeners, also alanwood.net/pesticides/); Farm Chemicals Handbook 2000 termed as herbicide Safeners are organic compounds which in Vol. 86, Meister Publishing Company, 2000; Some cases lead to better crop plant compatibility when applied jointly with specifically acting herbicides. Some B. Hock, C. Fedtke, R. R. Schmidt, Herbizide, Georg Thieme safeners are themselves herbicidally active. In these cases, the Verlag, Stuttgart 1995: safeners act as antidote or antagonist in the crop plants and thus reduce or even prevent damage to the crop plants. How W. H. Ahrens, Herbicide Handbook, 7th Edition, Weed Sci ever, in the compositions of the present invention, Safeners are ence Society of America, 1994; and generally not required. Therefore, a preferred embodiment of K. K. Hatzios, Herbicide Handbook, Supplement to 7th Edi the invention relates to compositions which contain no tion, Weed Science Society of America, 1998. US 2011/0065579 A1 Mar. 17, 2011 36

0511 Safeners include benoxacor, cloquintocet, cyo tortuosum, Kochia scoparia, Mercurialis annua, Myosotis metrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, arvensis, Papaver rhoeas, Raphanus raphanistrum, Salsola fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, kali, Sinapis arvensis, Sonchus arvensis, Thlaspi arvense, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, 2.2, Tagetes minuta, Richardia brasiliensis, and the like. 5-trimethyl-3-(dichloracetyl)-1,3-oxazolidine, 4-(dichloro 0516. The compositions of the present invention are also acetyl)-1-Oxa-4-azaspiro4.5 decane and oxabetrinil, as well Suitable for controlling a large number of annual and peren as thereof agriculturally acceptable salts and, provided they nial sedge weeds including cyperus species such as purple have a carboxyl group, their agriculturally acceptable deriva nutsedge (Cyperus rotundus L.), yellow nutsedge (Cyperus tives. 2.2.5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine esculentus L.), hime-kugu (Cyperus brevifolius H.), sedge CAS No. 52836-31-4 is also known under the name weed (Cyperus microiria Steud), rice flatsedge (Cyperus iria R-29148.4-(Dichloroacetyl)-1-oxa-4-azaspiro4.5 decane L.), and the like. CAS No. 71526-07-03 is also known under the names 0517. The compositions of the present invention are par AD-67 and MON 4660. ticularly useful in so-called burndown programms, in particu 0512. As safener, the compositions according to the inven lar preplant burndown programs. i.e. the compositions of the tion particularly preferably comprise at least one of the com invention are applied to a locus where crops will be planted pounds selected from the group of benoxacor, cloquintocet, before planting or emergence of the crop. cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flux 0518. Therefore, the present invention also relates to a ofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhy method for burndown treatment of undesirable vegetation in dride, 2.2.5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine, crops, comprising applying and 4-(dichloroacetyl)-1-Oxa-4-azaspiro4.5 decane and 0519 a) at least one herbicide A selected from glyphosate, oXabetrinil; and the agriculturally acceptable salt thereofand, glufosinate and their salts, and in the case of compounds having a COOH group, an agricul 0520 b) a herbicide B which is 3-5-(difluoromethoxy)- turally acceptable derivative as defined below. 1-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfo 0513. A preferred embodiment of the invention relates to nyl-4,5-dihydro-5,5-dimethyl-1,2-oxazole, compositions which contain no safener or virtually no safener to a locus where crops will be planted before planting or (i.e. less than 1% by weight, based on the total amount of the emergence of the crop. at least one herbicide A and herbicide B and optionally her 0521. In the burndown treatment of the present invention, bicide C) is applied. additionally at least one further herbicide C from the groups 0514. The compositions of the present invention are suit C.1 to C.8 as defined above can be applied together with the able for controlling a large number of harmful plants, includ herbicides A and B. The term “to apply together includes ing monocotyledonous weeds, in particular annual weeds simultaneous and Successive application. Likewise, applying Such as gramineous weeds (grasses) including Echinochloa the composition does not necessarily mean that the com species Such as barnyardgrass (Echinochloa crusgalli var. pounds A, B and optionally C must be applied as a single crus-galli), Digitaria species such as crabgrass (Digitaria formulation or as a tank mix. Rather, the composition sanguinalis), Setaria species such as green foxtail (Setaria includes separte formulations of herbicides A and B and viridis) and giant foxtail (Setaria faberii), Sorghum species optionally C, which can be applied as a single tank-mix or via Such as johnsongrass (Sorghum halepense Pers.), Avena spe separate application means. In any case, the at least one cies such as wild oats (Avenafatua), Cenchrus species such as herbicide A, the herbicide B and the one or more optional Cenchrus echinatus, Bromus species, Lolium species, herbicides C can be applied simultaneously or in Succession. Phalaris species, Eriochloa species, Panicum species, Bra 0522. However, it is also possible to apply the herbicide C chiaria species, annual bluegrass (Poa annua), blackgrass in the burndown treatment after seeding or even after emer (Alopecurus myosuroides), Aegilops cylindrica, Agropyron gence of the crop. repens, Apera spica-venti, Eleusine indica, Cynodon dacty 0523 Though possible, it is not necessary to formulate the lon and the like. herbicides A, B and optionally C in a single formulation. 0515. The compositions of the present invention are also Usually the herbicides A and B and optionally C are com Suitable for controlling a large number of dicotyledonous bined as a tank-mix prior to application. It is however also weeds, in particular broad leaf weeds including Polygonum possible to provide a premix of the herbicide B and the species such as wild buckwheat (Polygonum convolvOlus), optional herbicide C and to combine this premix with the at Amaranthus species such as pigweed (Amaranthus retrof. least one herbicide A. lexus), Chenopodium species Such as common lambsquarters 0524. The compositions of the present invention can be (Chenopodium album L.), Sida species Such as prickly sida applied in conventional manner by using techniques as skilled (Sida spinosa L.), Ambrosia species such as common rag person is familiar with. Suitable techniques include spraying, weed (Ambrosia artemisiifolia), Acanthospermum species, atomizing, dusting, spreading or watering. The type of appli Anthemis species, Atriplex species, Cirsium species, Convol cation depends on the intended purpose in a well known vulus species, Conyza species, Cassia species, Commelina manner, in any case, they should ensure the finest possible species, Datura species, Euphorbia species, Geranium spe distribution of the active ingredients according to the inven cies, Galinsoga Species, morning glory (Ipomoea species), tion. Lamium species, Malva species, Matricaria species, Sysim 0525. The compositions are applied to locus mainly by brium species, Solanum species, Xanthium species, Veronica spraying, in particular foliar spraying of an aqueous dilution species, Viola species, common chickweed (Stellaria media), of the active ingredients of the composition. Application can velvetleaf (Abutilon theophrasti), Hempsesbania (Sesbania be carried out by customary spraying techniques using, for exaltata Cory). Anoda Cristata, Bidens pilosa, Brassica example, water as carrier and spray liquor rates of from about kaber; Capsella bursa-pastoris, Centaurea cyanus, Galeopsis 10 to 2000 I/ha or 50 to 1000 I/ha (for example from 100 to tetrahit, Galium aparine, Helianthus annuus, Desmodium 500 I/ha). Application of the herbicidal compositions by the US 2011/0065579 A1 Mar. 17, 2011 37 low-volume and the ultra-low-volume method is possible, as 0532. Application may be effected, for example, by usual is their application in the form of microgranules. spraying techniques with water as the carrier, using amounts 0526 If the active ingredients are less well tolerated by of spray mixture of usuallay from 10 to 2000 I/ha, in particu certain crop plants, application techniques may be used in lar 50 to 1000 I?ha. which the herbicidal compositions are sprayed, with the aid of 0533. The required application rate of the composition of the spray apparatus, in Such a way that they come into as little the pure active compounds, i.e. of pyroxasulfone, herbicide A contact, if any, with the leaves of the sensitive crop plants and optionally herbicide C depends on the density of the while reaching the leaves of undesirable plants which grow undesired vegetation, on the development stage of the plants, underneath, or the bare soil (post-directed, lay-by). on the climatic conditions of the location where the compo 0527 The compositions can be applied pre- or post-emer sition is used and on the application method. In general, the gence, i.e. before, during and/or after emergence of the unde application rate of the composition (total amount of pyroxa sirable plants. sulfone, herbicide A and optional further actives) is from 55 to 0528. When the compositions are used in burndown pro 6000 g/ha, preferably from 100 to 5000 g/ha, from 200 to gramms, they can be applied prior to seeding (planting) or 4000 g/ha, and more preferably from 300 to 3000 g/ha of after seeding (or planting) of the crop plants but before the active ingredient (a.i.). emergence of the crop plants. The compositions are prefer 0534. The rate of application of herbicide A is usually ably applied prior to seeding of the crop plants. For burn from 50 g/ha to 3000 g/ha and preferably in the range from down, the compositions will generally be applied a date up to 100 g/ha to 2000 g/ha or from 200 g/ha to 1500 g/ha of active 9 month, frequently up to 6 month, preferably up to 4 month Substance (a.i.). prior to planting the crop. The burndown application can be 0535 The rate of application of pyroxasulfone is usually done at a date up to 1 day prior to emergence of the crop plant from 1 g/ha to 500 g/ha and preferably in the range from 5 and is preferably done at a date prior to seeding/planting of g/ha to 400 g/ha or from 20 g/ha to 300 g/ha of active sub the crop plant, preferably at a date of at least one day, prefer stance (a.i.). ably at least 2 days and in particular at least one 4 days prior 0536 The application rates of the herbicide C (total to planting or from 6 month to 1 day prior emergence, in amount of herbicide C) are generally in the range from 0.5 particular from 4 month to 2 days prior emergence and more g/ha to 5000 g/ha and preferably in the range from 1 g/ha to preferably from 4 month to 4 days prior emergence. It is, of 4000 g/ha or from 2 g/ha to 3000 g/ha of active substance. course, possible to repeat the burndown application once or 0537. The application rates of the herbicide C.1 (total more, e.g. once, twice, three times, four times or five times amount of herbicide C.1) are generally in the range from 0.5 within that time frame. g/ha to 1000 g/ha and preferably in the range from 1 g/ha to 0529. In the burndown treatment according to the present 500 g/ha or from 2 g/ha to 250 g/ha of active substance. The invention, the at least one herbicide A and the herbicide B are application rates of the herbicide C.1.1 (total amount of her applied to the field of the crop plants prior to the emergence of bicide C.1.1) are preferably in the range from 1 g/ha to 1000 the crop plants, in particular prior to seeding within the above g/ha and more preferably in the range from 5 g/ha to 500 g/ha time frame. In a specific embodiment of this burndown treat ment, the one or more herbicides C are also applied within or from 10 g/ha to 250 g/ha of active substance. this time frame. In this specific embodiment is also possible to 0538. The application rates of the herbicide C.2 (total additionally apply the one or more herbicides C and option amount of herbicide C.2) are generally in the range from 1 ally further pyroxasulfone after the planting or seeding or g/ha to 5000 g/ha and preferably in the range from 5 g/ha to even after emergence of the crop, preferably at a date until 12 2500 g/ha or from 10 g/ha to 2000 g/ha of active substance. weeks after emergence of the crop. In another specific The application rates of the herbicide C.2.1 (total amount of embodiment of this burndown treatment, the one or more herbicide C.2.1) are preferably in the range from 1 g/ha to 500 herbicides C and optionally further pyroxasulfone are only g/ha and more preferably in the range from 5 g/ha to 500 g/ha applied after the planting or seeding or even after emergence or from 10 g/ha to 250 g/ha of active substance. The applica of the crop, preferably at a date until 12 weeks after emer tion rates of the herbicides C.2.2 (total amount of herbicide gence of the crop. C.2.2) is preferably 1 to 1000 g/ha, more preferably 10 to 750 0530. It is a particular benefit of the compositions accord g/ha, most preferably 20 to 500 g/ha, of active substance ing to the invention that they have a very good post-emer (a.s.). gence herbicide activity, i.e. they show a good herbicidal 0539. The application rates of the herbicide C.3 (total activity against emerged undesirable plants. Thus, in a pre amount of herbicide C.3) are generally in the range from 1 ferred embodiment of invention, the compositions are applied g/ha to 3000 g/ha and preferably in the range from 5 g/ha to post-emergence, i.e. during and/or after, the emergence of the 2000 g/ha or from 10 g/ha to 1500 g/ha of active substance. undesirable plants. It is particularly advantageous to apply the (0540. The application rates of the herbicide C.5 (total mixtures according to the invention post emergent when the amount of herbicide C.5) are generally in the range from 5 undesirable plant starts with leaf development up to flower g/ha to 4000 g/ha and preferably in the range from 10 g/ha to ing. The compositions are particularly useful for controlling 2500 g/ha or from 20 g/ha to 1000 g/ha of active substance. undesirable vegetation which has already developed to a The rate of application of pyridinecarboxamide herbicides is state, which is difficult to control with conventional brun preferably from 5 to 500 g/ha, more preferably 10 to 400 g/ha, down compositions, i.e. when the individual weed is taller in particular 20 to 250 g/ha, of active substance (a.s.). than 10 cm (4 inches) or even taller than 15 cm (6 inches) 0541. The required application rates of the herbicide C.6 and/or for heavy weed populations. (total amount of herbicide C.6) are generally in the range 0531. In the case of a post-emergence treatment of the from 10 g/ha to 5000 g/ha and preferably in the range from 20 plants, the herbicidal mixtures or compositions according to g/ha to 4000 g/ha or from 50 g/ha to 3000 g/ha of active the invention are preferably applied by foliar application. Substance. US 2011/0065579 A1 Mar. 17, 2011

0542. The application rates of the herbicide C.7 (total and lentils, peanut, Sunflower, Sugarbeet, potato, cotton, bras amount of herbicide C.7) are generally in the range from 10 sica crops, such as oilseed rape, canola, mustard, cabbage and g/ha to 4000 g/ha and preferably in the range from 50 g/ha to turnip, turf, pasture, rangeland, grapes, pomefruit, such as 3000 g/ha or from 100 g/ha to 2500 g/ha of active substance. apple and pear, Stonefruit, such as peach, almond, walnut, The rate of application of the dinitroanilines is preferably pecans, olive, cherry, plum and apricot, citrus, coffee, pista from 10 g/ha to 4000 g/ha and more preferably in the range chio, garden ornamentals, such as roses, petunia, marigold, from 50 g/ha to 3000 g/ha or from 100 g/ha to 2500 g/ha of Snap dragon, bulb ornamentals such as tulips and narcissus, active Substance (a.i.). conifers and deciduous trees such as pinus, fir, oak, maple, 0543. The application rates of the herbicide C.8 (total dogwood, hawthorne, crabapple and rhamnus. amount of herbicide C.8) are generally in the range from 10 0561. The compositions of the present invention are most g/ha to 5000 g/ha and preferably in the range from 20 g/ha to suitable for burndown of undesired vegetation in fields of the 4000 g/ha or from 50 g/ha to 3000 g/ha of active substance. following crop plants: Small grain crops such as wheat, bar 0544 The application rates of the safener, if applied, are ley, rye, triticale and durum, rice, maize, Sugarcane, Soybean, generally in the range from 1 g/ha to 5000 g/ha and preferably pulse crops such as pea, bean and lentils, peanut, Sunflower, in the range from 2 g/ha to 5000 g/ha or from 5 g/ha to 5000 cotton, brassica crops, such as oilseed rape, canola, turf. g/ha of active substance. Preferably no safener or virtually no pasture, rangeland, grapes, stonefruit, such as peach, almond, safener is applied and thus the application rates are below 5 walnut, pecans, olive, cherry, plum and apricot, citrus and g/ha, in particular below 2 g/ha or below 1 g/ha. pistachio. 0545. The compositions according to the present inven 0562. If not stated otherwise, the compositions of the tion are suitable for combating/controlling common harmful invention are suitable for application infields of any variety of plants in fields, where useful plants shall be planted (i.e. in the aforementioned crop plants. crops). The compositions of the present invention are gener 0563 The compositions according to the invention can ally suitable for burndown of undesired vegetation in fields of also be used in crop plants which are resistant to one or more the following crops: herbicides owing to genetic engineering or breeding, which 0546 Grain crops, including e.g. are resistant to one or more pathogens such as plant pathog 0547 cereals (small grain crops) such as wheat (Triti enous fungi owing to genetic engineering or breeding, or cum aestivum) and wheat like crops such as durum (T. which are resistant to attack by insects owing to genetic durum), einkorn (T. monococcum), emmer (T. dicoc engineering or breeding. Suitable are for example crop plants, con) and spelt (T. spelta), rye (Secale cereale), triti preferably corn, wheat, Sunflower, rice, canola, oilseed rape, cale (Tritiosecale), barley (Hordeum vulgare); Soybeans, cotton and Sugarcane, which are resistant or toler 0548 maize (corn: Zea mays); ant to glyphosate and/or glufosinate, crop plants which are 0549 sorghum (e.g. Sorghum bicolour); resistant or tolerant to auxins such as dicamba, crop plants 0550 rice (Oryza spp. such as Oryza sativa and which are resistant or tolerant to HPPD inhibitors, crop plants Oryza glaberrima); and Sugarcane; which are resistant or tolerant to ALS inhibitors such as crop 0551 Legumes (Fabaceae), including e.g. soybeans plants which are resistant or tolerant to imidazolinones, crop (Glycine max.), peanuts (Arachis hypogaea and pulse plants which are resistant or tolerant to PPO inhibitors or crop crops such as peas including Pisum sativum, pigeon pea plants which, owing to introduction of the gene for Bt toxin by and cowpea, beans including broad beans (Vicia faba), genetic modification, are resistant to attack by certain insects. Vigna spp., and Phaseolus spp. and lentils (lens culinaris 0564. In a particular a specific embodiment, the composi var.); tions of the present inventions are used for controlling unde 0552 brassicaceae, including e.g. canola (Brassica sirable vegetation to crop plants, which are tolerant to herbi napus), oilseed rape (OSR, Brassica napus), cabbage cides, in particular in crop plants that are resistant or tolerant (B. Oleracea var.), mustard Such as B. juncea, B. Campes to glyphosate and/or glufosinate and which are stacked with tris, B. marinosa, B. nigra and B. toumefortii, and turnip further resistance or tolerance against at least one further (Brassica rapa Var.); herbicide, in particular at least one of the following herbi 0553 other broadleaf crops including e.g. sunflower, cides: auxins such as dicamba, HPPD inhibitors, ALS inhibi cotton, flax, linseed, Sugarbeet, potato and tomato; tors, in particular imidazolinones, PPO inhibitors. 0554 TNV-crops (TNV: trees, nuts and vine) including 0565. In these herbicide resistant or tolerant crops, the e.g. grapes, citrus, pomefruit, e.g. apple and pear, coffee, compositions of the present invention can be used both for pistachio and oilpalm, Stonefruit, e.g. peach, almond, burndown and for control of undesired vegetation after emer walnut, olive, cherry, plum and apricot; gence of the crops. Therefor, a particular embodiment of the 0555 turf, pasture and rangeland; invention relates to a method for controlling undesirable veg 0556 onion and garlic; etation in herbicide resistant or tolerant crops, in particular in 0557 bulb ornamentals such as tulips and narcissus: crop plants which are resistant or tolerant to glyphosate and/ 0558 conifers and deciduous trees such as pinus, fir, or glufosinate and which are optionally stacked with further oak, maple, dogwood, hawthorne, crabapple, and rham resistance or tolerance against at least one further herbicide, nus (buckthorn); and in particular at least one of the following herbicides: auxins 0559 garden ornamentals such as roses, petunia, mari such as dicamba, HPPD inhibitors, ALS inhibitors, in particu gold and Snapdragon. lar imidazolinones, PPO inhibitors. In this particular embodi 0560. The compositions of the present invention are in ment, the compositions can be used for burndown but also for particular suitable for burndown of undesired vegetation in the control of undesirable vegetation aftert the crop plants. fields of the following crop plants: Small grain crops such as 0566 In this particular method of the invention, the com wheat, barley, rye, triticale and durum, rice, maize (corn), position of the invention can be applied at least once prior to Sugarcane, Sorghum, soybean, pulse crops such as pea, bean planting or emergence of the herbicide resistant or tolerant US 2011/0065579 A1 Mar. 17, 2011 39 crop plant to achieve effective burndown of the undesirable with further herbicide tolerance. These compositions can also Vegetation and the composition can also be applied after used for controlling undesirable vegetation in Such crops after emergence of the herbicide resistant or tolerant crop plants. emergence of the crop. 0567 If the compositions of the present invention are used 0573 For example, a composition comprising glyphosate in crop plants, i.e. if they are applied in fields of the crop and/or glufosinate oran agriculturally acceptable salt thereof, plants after emergence of the crops, application methods and pyroxasulfone and an PSII inhibitor herbicide of the group application rates as described for burndown can be applied. If C.6.2. C.6.3 or C.6.8 is particularly useful for burndown in the active ingredients are less well tolerated by certain crop fields both of conventional crops of maize or Sugercane and plants, application techniques may be used in which the her crops of maize or Sugarcane having glyphosate and/or glufo bicidal compositions are sprayed, with the aid of the spray sinate tolerance, optionally stacked with further herbicide apparatus, in Such a way that they come into as little contact, tolerance. These compositions can also used for controlling if any, with the leaves of the sensitive crop plants while undesirable vegetation in Such crops after emergence of the reaching the leaves of undesirable plants which grow under crop. neath, or the bare soil (post-directed, lay-by). However such 0574 For example, a composition comprising glyphosate methods are generally not necessary and the compositions and/or glufosinate oran agriculturally acceptable salt thereof, can be simply applied over the top (OTT). pyroxasulfone and an PSII inhibitor herbicide of the group 0568 For example, a composition comprising glyphosate C.6.1 is particularly useful for burndown in fields both of and/or glufosinate oran agriculturally acceptable salt thereof, conventional crops of Small grain cereals or Sugercane and pyroxasulfone and an imidazolinone herbicide is particularly crops of Small grain cereals or Sugarcane having glyphosate useful for burndown in fields, where a glyphosate tolerant and/or glufosinate tolerance, optionally stacked with further crop having imidazolinone tolerance shall be planted Such as herbicide tolerance. These compositions can also used for maize, canola, wheat, soybeans or Sunflower, all of which controlling undesirable vegetation in Such crops after emer having glyphosate and/or glufosinate tolerance and imida gence of the crop. Zolinone tolerance. Such compositions are also particularly 0575 For example, a composition comprising glyphosate useful for burndown in fields where sugarcane shall be and/or glufosinate oran agriculturally acceptable salt thereof, planted, the Sugarcane being conventional Sugarcane or Sug pyroxasulfone and a microtubulin inhibitor herbicide is par arcane being tolerant to glyphosate or glufosinate optionally ticularly useful for burndown in fields both of conventional stacked with tolerance against imidazolinones. These com crops of Small grain cereals, maize, soybean, Sunflower or positions can also used for controlling undesirable vegetation Sugercane and crops of small grain cereals, maize, soybean, in crops having glyphosate and/or glufosinate resistance Sunflower or Sugercane having glyphosate and/or glufosinate stacked with imidazolinone resistance after emergence of the tolerance, optionally stacked with further herbicide tolerance. crop. These compositions can also used for controlling undesirable 0569. For example, a composition comprising glyphosate Vegetation in Such crops after emergence of the crop. and/or glufosinate oran agriculturally acceptable salt thereof, 0576 For example, a composition comprising glyphosate pyroxasulfone and an auxin herbicide is particularly useful and/or glufosinate oran agriculturally acceptable salt thereof, for burndown in fields both of conventional crops such as pyroxasulfone and a VLCFA inhibitor herbicide is particu maize, canola, wheat, soybeans, Sunflower and Sugarcane and larly useful for burndown in fields both of conventional crops crops having glyphosate and/or glufosinate tolerance, option of Small grain cereals, maize, soybean, Sunflower or Suger ally stacked with auxin tolerance. These compositions can cane and crops of Small grain cereals, maize, soybean, Sun also used for controlling undesirable vegetation in crops hav flower or Sugercane having glyphosate and/or glufosinate ing glyphosate tolerance optionally stacked with auxin resis tolerance, optionally stacked with further herbicide tolerance. tance after emergence of the crop. These compositions can also used for controlling undesirable 0570 For example, a composition comprising glyphosate Vegetation in Such crops after emergence of the crop. and/or glufosinate oran agriculturally acceptable salt thereof, 0577. The active ingredients used in the compositions of pyroxasulfone and an PPO inhibitor herbicide is particularly the present invention are usually available as pure Substances useful for burndown in fields both of conventional crops such and as formulations. as maize, wheat, soybeans, Sunflower and Sugarcane and 0578. The formulations contain, besides the active ingre crops having glyphosate and/or glufosinate tolerance, option dient or the composition, at least one organic or inorganic ally stacked with PPO inhibitor tolerance. carrier material. The formulations may also contain, if 0571 For example, a composition comprising glyphosate desired, one or more Surfactants and, if desired, one or more and/or glufosinate oran agriculturally acceptable salt thereof, further auxiliaries customary for crop protection composi pyroxasulfone and an PPO inhibitor herbicide is particularly tions. useful for burndown in fields both of conventional crops of 0579. The formulation may be in the form of a single maize and Sugarcane and Such crops having glyphosate and/ package formulation containing both the at least one herbi or glufosinate tolerance, optionally stacked with further her cide A and the herbicide B and optionally the one or more bicide tolerance. These compositions can also used for con herbicides C together with liquid and/or solid carrier materi trolling undesirable vegetation in Such crops after emergence als, and, if desired, one or more surfactants and, if desired, one of the crop. or more further auxiliaries customary for crop protection 0572 For example, a composition comprising glyphosate compositions. The formulation may be in the form of a two or and/or glufosinate oran agriculturally acceptable salt thereof, multi (e.g. three, four or five) package formulation, wherein pyroxasulfone and an HPPD inhibitor herbicide is particu one package contains a formulation of pyroxasulfone while larly useful for burndown in fields both of conventional crops the other package contains a formulation of the at least one of small grain cereals and crops of small grain cereals having herbicide A and optionally one or more further formulations glyphosate and/or glufosinate tolerance, optionally stacked contains the at least one herbicide C, whereinall formulations US 2011/0065579 A1 Mar. 17, 2011 40 contain at least one carrier material, if desired, one or more Sorbitol esters, lignoSulfite waste liquors and proteins, dena Surfactants and, if desired, one or more further auxiliaries turated proteins, polysaccharides (e.g. methylcellulose), customary for crop protection compositions. In the case of hydrophobically modified starches, polyvinyl alcohol two or multi package formulations the formulation contain (Mowiol types Clariant), polycarboxylates (BASF AG, ing pyroxasulfone and the formulation containing the herbi Sokalan types), polyalkoxylates, polyvinylamine (BASF AG, cide A and optionally the one or more formulations contain Lupamine types), polyethyleneimine (BASF AG, Lupasol ing the one or more herbicides C are mixed prior to types), polyvinylpyrrolidone and copolymers thereof. application. Preferably the mixing is performed as a tank mix, 0584) Examples of thickeners (i.e. compounds which i.e. the formulations are mixed immediately prior or upon impart to the formulation modified flow properties, i.e. high dilution with water. Viscosity in the State of rest and low viscosity in motion) are 0580. In the formulations the active ingredients and polysaccharides, such as Xanthan gum (Kelzan(R) from optional further actives are present in Suspended, emulsified Kelco), RhodopolR 23 (Rhone Poulenc) or Veegum(R) (from or dissolved form. The formulation can be in the form of R.T. Vanderbilt), and also organic and inorganic sheet miner aqueous solutions, powders, Suspensions, also highly-con als, such as Attaclay R (from Engelhardt). centrated aqueous, oily or other Suspensions or dispersions, 0585 Examples of antifoams are silicone emulsions (such aqueous emulsions, aqueous microemulsions, aqueous as, for example, Silikon RSRE, Wacker or Rhodorsil R) from Suspo-emulsions, oil dispersions, pastes, dusts, materials for Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, spreading or granules. organofluorine compounds and mixtures thereof. 0581 Depending on the formulation type, they comprise 0586 Bactericides can be added for stabilizing the aque one or more liquid or Solid carriers, if appropriate Surfactants ous herbicidal formulations. Examples of bactericides are (such as dispersants, protective colloids, emulsifiers, wetting bactericides based on dichlorophen and benzyl alcohol hemi agents and tackifiers), and if appropriate further auxiliaries formal (Proxel R. from ICI or ActicideR RS from Thor Che which are customary for formulating crop protection prod mie and Kathon(R) MK from Rohm & Haas), and also isothia ucts. The person skilled in the art is sufficiently familiar with Zolinone derivates, such as alkylisothiazolinones and the recipes for such formulations. Further auxiliaries include benzisothiazolinones (Acticide MBS from Thor Chemie). e.g. organic and inorganic thickeners, bactericides, antifreeze 0587 Examples of antifreeze agents are ethylene glycol, agents, antifoams, colorants and, for seed formulations, adhe propylene glycol, urea or glycerol. SVS. 0588. Examples of colorants are both sparingly water 0582 Suitable carriers include liquid and solid carriers. soluble pigments and water-soluble dyes. Examples which Liquid carriers include e.g. non-aqeuos Solvents such as may be mentioned are the dyes known under the names cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahy Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1. dronaphthalene, alkylated naphthalenes and their derivatives, and also pigment blue 15:4, pigment blue 15:3, pigment blue alkylated benzenes and their derivatives, alcohols such as 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, methanol, ethanol, propanol, butanol and cyclohexanol, pigment yellow 13, pigment red 112, pigment red 48:2, pig ketones Such as cyclohexanone, strongly polar solvents, e.g. ment red 48:1, pigment red 57:1, pigment red 53:1, pigment amines Such as N-methylpyrrolidone, and water as well as orange 43, pigment orange 34, pigment orange 5, pigment mixtures thereof. Solid carriers include e.g. mineral earths green 36, pigment green 7, pigment white 6, pigment brown Such as silicas, silica gels, silicates, talc, kaolin, limestone, 25, basic violet 10, basic violet 49, acid red 51, acid red 52, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red calcium Sulfate, magnesium Sulfate, magnesium oxide, 108. ground synthetic materials, fertilizers such as ammonium 0589 Examples of adhesives are polyvinylpyrrolidone, Sulfate, ammonium phosphate, ammonium nitrate, ureas, and polyvinyl acetate, polyvinyl alcohol and tylose. products of vegetable origin Such as cereal meal, tree bark 0590 To prepare emulsions, pastes or oil dispersions, the meal, wood meal and nutshell meal, cellulose powders, or active the components, as Such or dissolved in an oil or other solid carriers. Solvent, can be homogenized in water by means of wetting 0583 Suitable surfactants (adjuvants, wetting agents, agent, tackifier, dispersant or emulsifier. Alternatively, it is tackifiers, dispersants and also emulsifiers) are the alkali possible to prepare concentrates consisting of active Sub metal salts, alkaline earth metal salts and ammonium salts of stance, wetting agent, tackifier, dispersant or emulsifier and, aromatic Sulfonic acids, for example lignoSulfonic acids (e.g. if desired, solvent or oil, and these concentrates are suitable Borrespers-types, Borregaard), phenolsulfonic acids, naph for dilution with water. thalenesulfonic acids (Morwet types, Akzo Nobel) and dibu tylnaphthalenesulfonic acid (Nekal types, BASF AG), and of 0591 Powders, materials for spreading and dusts can be fatty acids, alkyl- and alkylarylsulfonates, alkylsulfates, lau prepared by mixing or concomitant grinding of the active the ryl ether sulfates and fatty alcohol sulfates, and salts of sul herbicides A, B, optionally C and D with a solid carrier. fated hexa-hepta- and octadecanols, and also offatty alcohol 0592 Granules, e.g. coated granules, impregnated gran glycol ethers, condensates of Sulfonated naphthalene and its ules and homogeneous granules, can be prepared by binding derivatives with formaldehyde, condensates of naphthalene the active ingredients to Solid carriers. or of the naphthalenesulfonic acids with phenol and formal 0593. The formulations of the invention comprise a herbi dehyde, polyoxyethylene octylphenol ether, ethoxylated cidally effective amount of the composition of the present isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphe invention. The concentrations of the active the active ingre nyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl dients in the formulations can be varied within wide ranges. In alcohol, fatty alcohol/ethylene oxide condensates, ethoxy general, the formulations comprise from 1 to 98% by weight, lated castor oil, polyoxyethylene alkyl ethers or polyoxypro preferably 10 to 60% by weight, of active ingredients (sum of pylene alkyl ethers, lauryl alcohol polyglycol ether acetate, pyroxasulfone, herbicide A and optionally further actives). US 2011/0065579 A1 Mar. 17, 2011

0594. The active ingredients are employed in a purity of water gives a stable dispersion or solution of the active com from 90% to 100%, preferably 95% to 100% (according to pound. The formulation has an active compound content of NMR spectrum). 50% by weight. 0595. The active compounds A, B and optionally Caswell as the compositions according to the invention can, for G Water-Dispersible Powders and Water-Soluble Powders example, be formulated as follows: 0602 75 parts by weight of active compound (or compo 1. Products for Dilution with Water sition) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution A Water-Soluble Concentrates with water gives a stable dispersion or solution of the active compound. The active compound content of the formulation 0596) 10 parts by weight of active compound (or compo is 75% by weight. sition) are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other adju H Gel Formulations vants are added. The active compound dissolves upon dilu 0603 Inaball mill, 20 parts by weight of active compound tion with water. This gives a formulation with an active com (or composition), 10 parts by weight of dispersant, 1 part by pound content of 10% by weight. weight of gelling agent and 70 parts by weight of water or of an organic solvent are mixed to give a fine Suspension. Dilu B Dispersible Concentrates tion with water gives a stable Suspension with active com pound content of 20% by weight. 0597 20 parts by weight of active compound (or compo sition) are dissolved in 70 parts by weight of cyclohexanone 2. Products to be Applied Undiluted with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a I Dusts dispersion. The active compound content is 20% by weight. 0604 5 parts by weight of active compound (or composi tion) are ground finely and mixed intimately with 95 parts by C Emulsifiable Concentrates weight of finely divided kaolin. This gives a dusting powder 0598. 15 parts by weight of active compound (or compo with an active compound content of 5% by weight. sition) are dissolved in 75 parts by weight of an organic Solvent (e.g. alkylaromatics) with addition of calcium dode Granules (GR, FG, GG, MG) cylbenzenesulfonate and castor oil ethoxylate (in each case 5 0605 0.5 parts by weight of active compound (or compo parts by weight). Dilution with water gives an emulsion. The sition) are ground finely and associated with 99.5 parts by formulation has an active compound content of 15% by weight of carriers. Current methods here are extrusion, spray weight. drying or the fluidized bed. This gives granules to be applied undiluted with an active compound content of 0.5% by D Emulsions weight. 0599 25 parts by weight of active compound (or compo KULV Solutions (UL) sition) are dissolved in 35 parts by weight of an organic 0606 10 parts by weight of active compound (or compo Solvent (e.g. alkylaromatics) with addition of calcium dode sition) are dissolved in 90 parts by weight of an organic cylbenzenesulfonate and castor oil ethoxylate (in each case 5 Solvent, for example Xylene. This gives a product to be parts by weight). This mixture is introduced into 30 parts by applied undiluted with an active compound content of 10% by weight of water by means of an emulsifier (Ultraturrax) and weight. made into a homogeneous emulsion. Dilution with water 0607 Aqueous use forms can be prepared from emulsion gives an emulsion. The formulation has an active compound concentrates, Suspensions, pastes, wettable powders or water content of 25% by weight. dispersible granules by adding water. E Suspensions 0608. It may furthermore be beneficial to apply the com positions of the invention alone or in combination with other 0600. In an agitated ball mill, 20 parts by weight of active herbicides, or else in the form of a mixture with other crop compound (or composition) are comminuted with addition of protection agents, for example together with agents for con 10 parts by weight of dispersants and wetters and 70 parts by trolling pests or phytopathogenic fungi or bacteria. Also of weight of water or an organic solvent to give a fine active interest is the miscibility with mineral salt solutions, which compound Suspension. Dilution with water gives a stable are employed for treating nutritional and trace element defi Suspension of the active compound. The active compound ciencies. Other additives such as non-phytotoxic oils and oil content in the formulation is 20% by weight. concentrates may also be added. F Water-Dispersible Granules and Water-Soluble Granules USE EXAMPLES 0601 50 parts by weight of active compound (or compo 0609. The effect of the herbicidal compositions according sition) are ground finely with addition of 50 parts by weight of to the invention of herbicides A and B and, if appropriate, dispersants and wetters and made into water-dispersible or safener on the growth of undesirable plants compared to the water-soluble granules by means oftechnical appliances (for herbicidally active compounds alone was demonstrated by example extrusion, spray tower, fluidized bed). Dilution with the following greenhouse experiments: US 2011/0065579 A1 Mar. 17, 2011 42

0610 For the pre-emergence treatment, directly after sow ing the active compounds, which had been Suspended or emulsified in water, were applied by means of finely distrib compound B: uted noZZles. The containers were irrigated gently to promote (B) germination and growth and Subsequently covered with trans parent plastic hoods until plant had rooted. This cover caused uniform germination of the tests plants, unless this was adversely affected by active compounds. 0611 For the post-emergence treatment, the test plants were first grown to a height of 3 to 20 cm, depending on the plant habit, and only then treated. Here, the herbicidal com positions were Suspended or emulsified in water as distribu compound D: tion medium and sprayed using finely distributing nozzles. (D) 0612. The respective herbicides B and/or safener were F CH3 / formulated as 10% by weight strength Suspension concen N trate and introduced to the spray liquor with the amount of Solvent system used for applying the active compound. Her N X=s bicides A, C and/or safener were used as commercially avail O N able formulations and introduced to the spray liquor with the y-N V O VCH3 amount of solvent system used for applying the active com pound. In the examples, the solvent used was water. 0613 Glyphosate was used as a commercially available 0627 The test period extended over 21 days. During this SL-formulation containing 360 g/l of glyphosate as its iso time, the plants were tended, and their response to the treat propylammonium salt. ments with active compound was evaluated. 0614 Pyroxasulfone was used as an emulsifiable concen (0628. The evaluation for the damage caused by the chemi trate having an active ingredient concentration of 5% by cal compositions was carried out using a scale from 0 to weight. 100%, compared to the untreated control plants. Here, 0 means no damage and 100 means complete destruction of the 0615. Imazamox was used as a commercially available plants. SL-formulation containing 120 g/l of imaZamox. 0629. The plants used in the greenhouse experiments 0616 Imazapic was used as a commercially available SL belonged to the following species: formulation containing 120 g/l of imazapic. 0.617 Pendimethalin was used as an emulsifiable concen trate having an active ingredient concentration of 396 g/l. Scientific Name Code Common Name 0618. Dimethenamid-P was used as an emulsifiable con Abution theophrasti ABUTH welvetleaf centrate having an active ingredient concentration of 720 g/l. Agropyron repens AGRRE quackgrass 0619 AtraZin was used as an aqueous Suspension concen Alopectiris myosiiroides ALOMY blackgrass Amaranthus retroflexus AMARE pig weed trate having an active ingredient concentration of 500 g/l. Ambrosia artemisifolia AMBEL common ragweed 0620 Dicamba was used as a commercially available SL Apera spica-venti APESV windgrass Avena fattia AVEFA wild oat formulation having an active ingredient concentration of 480 Brachiaria plantaginea BRAPL alexandergrass g/l. Bromits inermis BROIN awnless brome Bromus steriis BROST sterile brome 0621 Picolinafen was used as a commercially available Brassica naptis spp. naptis BRSNW winter oilseed-rape WG-formulation having an active ingredient concentration of Capsella bursa-pastoris CAPBP sheperd's-purse 75% by weight. Cenchrus echinaius CCHEC Sandbur Chenopodium album CHEAL lambsquarter 0622 Saflufenacil was used as an emulsifiable concentrate Commelina benghaiensis COMBE tropical spiderwort having an active ingredient concentration of 120 g/l. Digitaria Sangiinalis DIGSA large crabgrass Echinochloa crus-galli ECHCG barnyardgrass 0623 Flumioxazin was used as a WG-formulation having Eleusine indica ELEIN gOOSegraSS Galium aparine GALAP cleaver an active ingredient concentration of 51% by weight. Glycine max GLXMA Soybean 0624 Compound B was used as an emulsifiable concen Gossypium hirsuttin GOSH cottOn Helianthus annuit is HELAN Sunflower trate having an active ingredient concentration of 5% by Hordeum vulgare HORVW winter barley weight. Kochia Scoparia KCHSC kochia Lamiin purpurelim LAMPU red deadnettle 0625 Compound D was used as an emulsifiable concen Lolium multiflorum LOLMU italian ryegrass trate having an active ingredient concentration of 5% by Matricaria inermis MATIN scentless mayweed weight. Mercuria is annua MERAN annual mercury Orysa sativa ORYSA rice 0626 Isoxaflutole was used as a WG-formulation having Panicum dichotomiflorum PANDI fall panicum an active ingredient concentration of 75% by weight. US 2011/0065579 A1 Mar. 17, 2011 43

R. Colby (1967) “Calculating synergistic and antagonistic -continued responses of herbicide combinations'. Weeds 15, p. 22ff. For two component mixtures the value E was calculated by the Scientific Name Code Common Name following formula Panicum miliaceum PANMI proso millet Phaiaris canariensis canary graSS Ipomoea purpurea tall morningglory For three component mixtures the value E was calculated by Poa annia annual bluegrass Polygontin convolvulus wild buckwheat the following formula Secale cereaie winter rye 0631 E=X+Y+Z-(XY+XZ+YZ)/100+(XYZ/10000) Setaria faberii giant foxtail where Setaria itaica foxtail millet 0632 X-effect in percent using herbicide A at an appli Setaria initescens yellow foxtail Setaria viridis SE green foxtail cation rate a: Sinapis arvensis S wild mustard 0633 Y-effect in percent using herbicide Batan appli Soianum nigrum SOLNI black nightshade cation rate b: Sorghum halepense SOREHA johnsongrass Steiaria media STEME chickweed 0634 Zeffect in percent using herbicide Catan appli Thlaspi arvense THLAR field pennycress cation rate c; Trictim aestivum TRZAS spring wheat 0635 E=expected effect (in 96) of A+B at application Trictim aestivum TRZAW winter wheat rates a+b. or Veronica persica VERPE field speedwell Vioia arvensis VIOAR field pansy 0636 E=expected effect (in 96) of A+B+C at applica Xanthium strumarium XANST cocklebur tion rates a+b+c. Zea mays ZEAMX COil 0637. If the value observed in this manner is higher than the value E calculated according to Colby, a synergistic effect 0630 Colby's formula was applied to determine whether is present. the composition showed synergistic action. The value E, 0638 Tables 1 to 12 relate to the herbicidal activity of the which is to be expected if the activity of the individual com individual actives and of their combinations in post-emer pounds is just additive, was calculated using the method of S. gence application assessed 20 DAT.

TABLE 1 Application in Post-Emergence of Glyphosate, Pyroxasulfone and Imazanox solo application combination glyphosate + pyroxasulfone + imazanox glyphosate (A pyroxasulfone (B imaZamox (C Synergism % activity % activity % activity Observed % activity expected% activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT

ALOMY 100 40 25 50 10 30 1OO - 25 - 10 98 79 Y DIGSA 100 85 25 50 10 2O 1OO - 25 - 10 1OO 94 Y LOLMU 100 75 25 50 10 60 1OO - 25 - 10 98 95 Y LOLMU 50 40 12.5 50 5 40 SO - 12.5 - 5 85 82 Y ABUTH 50 O 12.5 40 5 50 SO - 12.5 - 5 90 70 Y CHEAL 100 50 25 2O 10 30 1OO - 25 - 10 95 72 Y CHEAL 50 40 12.5 2O 5 15 SO - 12.5 - 5 90 59 Y GALAP 100 15 25 8O 10 30 1OO - 25 - 10 95 88 Y GALAP 50 10 12.5 70 5 2O SO - 12.5 - 5 90 78 Y MATIN 50 65 12.5 O 5 25 SO - 12.5 - 5 8O 74 Y

TABLE 2 Application in Post-Emergence of Glyphosate, Pyroxasulfone and Inazapic Solo application combination glyphosate + pyroxasulfone + imazapic glyphosate (A pyroxasulfone (B imazapic (C Synergism % activity % activity % activity Observed % activity expected% activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 2OO 85 50 50 2O 45 2OO -- SO - 20 98 96 Y DIGSA 50 70 12.5 40 5 50 SO - 12.5 - 5 95 91 Y LOLMU 50 40 12.5 50 5 60 SO - 12.5 - 5 90 88 Y ABUTH 50 O 12.5 40 5 60 SO - 12.5 - 5 85 76 Y CHEAL 2OO 8O 50 2O 2O 40 2OO -- SO - 20 95 90 Y GALAP 50 10 12.5 70 5 55 SO - 12.5 - 5 95 88 Y US 2011/0065579 A1 Mar. 17, 2011 44

TABLE 3 Application in Post-Emergence of Glyphosate, Pyroxasulfone and Pendimethalin Solo application combination glyphosate + pyroxasulfone + pendimethalin glyphosate (A pyroxasulfone (B pendimethalin (C Synergism % activity % activity % activity Observed % activity expected% activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 200 85 50 50 400 40 2OO -- SO - 400 98 96 Y LOLMU 100 75 25 50 2OO 30 100 - 25 - 200 98 91 Y SETVI 50 70 12.5 70 1OO 30 SO - 12.5 + 100 95 94 Y AMARE 50 90 12.5 75 1OO 75 SO - 12.5 + 100 100 99 Y MATIN 400 95 100 15 800 O 400 - 100 - 8OO 100 96 Y MATIN 50 65 12.5 O 1OO O SO - 12.5 + 100 8O 65 Y

TABLE 4 Application in Post-Emergence of Glyphosate, PYTOxasulfone and Dimethenanid-P Solo application combination glyphosate + pyroxasulfone + dimethenanid-P glyphosate (A pyroxasulfone (B) dimethenanid-P (C Synergism % activity % activity % activity Observed % activity expected% activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 200 85 50 50 S4O 30 2OO -- SO - 540 100 95 Y ALOMY 100 40 25 50 270 2O 100 - 25 - 270 90 76 Y DIGSA 100 85 25 50 270 50 100 - 25 - 270 100 96 Y DIGSA SO 70 12.5 40 135 SO SO - 12.5 - 135 98 91 Y LOLMU 50 40 12.5 50 135 60 SO - 12.5 - 135 95 88 Y ABUTH 200 70 50 70 S4O 15 2OO -- SO - 540 95 92 Y ABUTH 50 O 12.5 40 135 15 SO - 12.5 - 135 70 49 Y CHEAL 100 50 25 2O 270 2O 100 - 25 - 270 95 68 Y MATIN 100 90 25 O 270 O 100 - 25 - 270 98 90 Y MATIN 50 65 12.5 O 135 O SO - 12.5 - 135 90 65 Y SINAR 50 8O 12.5 65 135 45 SO - 12.5 - 135 100 96 Y

TABLE 5 Application in Post-Emergence of Glyphosate, Pyroxasulfone and Atrazin Solo application combination glyphosate + pyroxasulfone + atrazin glyphosate (A pyroxasulfone (B atrazin (C Synergism % activity % activity % activity Observed % activity expected% activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 200 85 50 50 250 50 2OO -- SO - 250 100 96 Y DIGSA 50 70 12.5 40 62.5 O SO - 12.5 - 62.5 85 82 Y CHEAL 100 50 25 2O 125 60 100 - 25 - 125 98 84 Y CHEAL 50 40 12.5 2O 62.5 2O SO - 12.5 - 62.5 85 62 Y

TABLE 5 Application in Post-Emergence of Glyphosate, Pyroxasulfone and Dicamba solo application combination glyphosate + pyroxasulfone + dicamba glyphosate (A DYIOxasulfone (B dicamba (C Observed expected Synergism % activity % activity % activity % activity % activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 50 2O 12.5 30 25 10 SO - 12.5 - 25 55 50 Y LOLMU 100 75 25 50 50 O 1OO - 25 - SO 95 88 Y ABUTH 100 60 25 40 50 50 1OO - 25 - SO 95 88 Y US 2011/0065579 A1 Mar. 17, 2011 45

TABLE 5-continued Application in Post-Emergence of Glyphosate, Pyroxasulfone and Dicamba solo application combination glyphosate + pyroxasulfone + dicamba glyphosate (A pyroxasulfone (B dicamba (C Observed expected Synergism % activity % activity % activity % activity % activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT

CHEAL 100 50 25 2O 50 50 1OO - 25 - SO 90 8O Y MATIN 50 65 12.5 O 25 45 SO - 12.5 - 25 95 81 Y

TABLE 7 Application in Post-Emergence of Glyphosate, Pyroxasulfone and Picolinafen Solo application combination glyphosate + pyroxasulfone + picolinafen glyphosate (A pyroxasulfone (B picolina?en (C Synergism % activity % activity % activity Observed % activity expected% activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 200 85 50 50 25 O 2OO -- SO - 25 98 93 Y ALOMY 50 2O 12.5 30 6.25 O SO - 12.5 - 6.25 55 44 Y DIGSA 100 85 25 50 12.5 45 100 - 25 - 12.5 100 96 Y DIGSA 50 70 12.5 40 6.25 30 SO - 12.5 - 6.25 95 87 Y LOLMU 100 75 25 50 12.5 10 100 - 25 - 12.5 99 89 Y ABUTH 200 70 50 70 25 60 2OO -- SO - 25 98 96 Y ABUTH 50 O 12.5 40 6.25 30 SO - 12.5 - 6.25 70 58 Y CHEAL 100 SO 25 20 12.5 30 100 + 25 + 12.5 90 72 Y GALAP 50 10 12.5 70 6.25 30 SO - 12.5 - 6.25 90 81 Y MATIN 400 95 100 15 50 60 400 - 1 OO -- SO 100 98 Y POLCO 400 90 100 65 50 8O 400 - 1 OO -- SO 100 99 Y

TABLE 8 Application in Post-Emergence of Glyphosate, Pyroxasulfone and flunioxazin Solo application combination glyphosate + pyroxasulfone + flunioxazin glyphosate (A pyroxasulfone (B flumioxazin (C Synergism % activity % activity % activity Observed % activity expected% activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 100 30 25 70 12.5 2O 100 - 25 - 12.5 95 83 Y ALOMY 50 15 12.5 40 6.25 2O SO - 12.5 - 6.25 85 59 Y AVEFA 100 45 25 75 6.25 35 100 - 25 - 6.25 98 91 Y DIGSA 50 70 12.5 50 6.25 15 SO - 12.5 - 6.25 95 87 Y CHEAL 100 85 25 45 12.5 30 100 - 25 - 12.5 100 94 Y CHEAL 50 30 12.5 35 6.25 O SO - 12.5 - 6.25 98 55 Y GALAP 100 45 25 85 12.5 30 100 - 25 - 12.5 100 94 Y GALAP 50 40 12.5 40 6.25 30 SO - 12.5 - 6.25 98 75 Y MATIN 50 90 12.5 O 6.25 65 SO - 12.5 - 6.25 100 97 Y

TABLE 9 Application in Post-Emergence of Glyphosate, PYTOxasulfone and Safiufenacil Solo application combination glyphosate + pyroxasulfone + saflufenacil glyphosate (A pyroxasulfone (B saflufenacil (C Synergism % activity % activity % activity Observed % activity expected% activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 100 30 25 70 3.13 O 100 - 25 - 3.125 90 79 Y ALOMY 50 15 12.5 40 1.56 O SO - 12.5 - 1.56 70 49 Y US 2011/0065579 A1 Mar. 17, 2011 46

TABLE 9-continued

Application in Post-Emergence of Glyphosate, Pyroxasulfone and Safiufenacil

Solo application combination glyphosate + pyroxasulfone + saflufenacil

glyphosate (A) pyroxasulfone (B) saflufenacil (C) Synergism

% activity % activity % activity Observed % activity expected % activity YN weed 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT

DIGSA 50 70 12.5 50 1.56 O SO - 12.5 - 1.56 90 85 ECHCG 50 30 12.5 75 1.56 O SO - 12.5 - 1.56 85 83 ABUTH 50 O 12.5 60 1.56 45 SO - 12.5 - 1.56 95 78 CHEAL 50 30 12.5 35 1.56 40 SO - 12.5 - 1.56 90 73 GALAP 100 45 25 85 3.13 30 100 - 25 - 3.125 98 94 MATIN 100 95 25 O 3.13 55 100 - 25 - 3.125 100 98 MATIN 50 90 12.5 O 1.56 2O SO - 12.5 - 1.56 100 92 POLCO 100 50 25 50 3.13 55 100 - 25 - 3.125 98 89 POLCO 50 30 12.5 35 1.56 45 SO - 12.5 - 1.56 98 75

TABLE 10

Application in Post-Emergence of Glyphosate, Pyroxasulfone and Compound B

Solo application combination glyphosate + pyroxasulfone + Compound B glyphosate (A) pyroxasulfone (B) compound B (C) Synergism

% activity % activity % activity Observed % activity expected % activity YN weed 20 DAT gai?ha 20 DAT 20 DAT gai?ha 20 DAT 20 DAT 20 DAT

ALOMY 100 30 25 70 12.5 35 100 - 25 - 12.5 95 86 ALOMY 50 15 12.5 40 6.25 2O SO - 12.5 - 6.25 85 59 DIGSA 50 70 12.5 50 6.25 50 SO - 12.5 - 6.25 95 93 ABUTH 100 O 25 65 6.25 98 100 - 25 - 6.25 100 99 CHEAL 50 30 12.5 35 6.25 85 SO - 12.5 - 6.25 100 93 POLCO 50 30 12.5 35 6.25 90 SO - 12.5 - 6.25 100 95

TABLE 11 Application in Post-Emergence of Glyphosate, Pyroxasulfone and Compound D Solo application combination glyphosate + pyroxasulfone + compound D glyphosate (A pyroxasulfone (B compound D (C Observed expected Synergism % activity % activity % activity % activity % activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 100 30 25 70 6.25 40 100 - 25 - 6.25 98 87 ALOMY 50 15 12.5 40 3.13 30 SO - 12.5 - 3.125 75 64 AVEFA 100 45 25 75 6.25 75 100 - 25 - 6.25 98 97 DIGSA 50 70 12.5 50 3.13 35 SO - 12.5 - 3.125 95 90 LOLMU 50 45 12.5 55 3.13 40 SO - 12.5 - 3.125 95 85 CHEAL 50 30 12.5 35 3.13 45 SO - 12.5 - 3.125 90 75 GALAP 100 45 25 85 6.25 30 100 - 25 - 6.25 98 94 GALAP 50 40 12.5 40 3.13 30 SO - 12.5 - 3.125 98 75 POLCO 50 30 12.5 35 3.13 95 SO - 12.5 - 3.125 100 98 US 2011/0065579 A1 Mar. 17, 2011 47

TABLE 12 Application in Post-Emergence of Glyphosate, Pyroxasulfone and Isoxaflutole Solo application combination glyphosate + pyroxasulfone + isoxaflutole glyphosate (A pyroxasulfone (B isoxaflutole (C Synergism % activity % activity % activity Observed % activity expected% activity YN weed gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT gai?ha 20 DAT 20 DAT 20 DAT ALOMY 50 15 12.5 40 6.25 O SO - 12.5 - 6.25 8O 49 Y DIGSA 50 70 12.5 50 6.25 15 SO - 12.5 - 6.25 90 87 Y ABUTH 50 O 12.5 60 6.25 55 SO - 12.5 - 6.25 90 82 Y CHEAL 50 30 12.5 35 6.25 75 SO - 12.5 - 6.25 95 89 Y POLCO 200 50 50 50 25 45 2OO -- SO - 25 98 86 Y

1.-30. (canceled) C.1) herbicides of the group of acetolactat synthase inhibi 31. A herbicidal composition comprising tors, a) at least one herbicide A selected from glyphosate, glu C.3) herbicides of the group of auxines, fosinate and their salts, and C.4) herbicides of the group of 4-hydroxyphenylpyruvate b) a herbicide B which is 3-5-(difluoromethoxy)-1-me thyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl-4, dioxygenase inhibitors, 5-dihydro-5,5-dimethyl-1,2-oxazole. C.6) herbicides of the group of photosystem II inhibitors, 32. The herbicidal composition as claimed in claim 31, C.7) herbicides of the group of microtubulin inhibitors, and wherein the weight ratio of herbicide A to herbicide B is from C.8) herbicides of the group of VLCFA inhibitors. 2000:1 to 1:10. 39. The herbicidal composition as claimed in claim 38, 33. The herbicidal composition as claimed in claim 32, wherein the at least one further herbicide C comprises at least comprising at least one further herbicide C selected from the one acetolactate synthase inhibitor C. 1, selected from the group consisting of group of imidazolinone herbicides. C.1) herbicides of the group of acetolactate synthase 40. The herbicidal composition as claimed in claim 39, inhibitors, wherein the at least one acetolactate synthase inhibitor C. 1 is C.2) herbicides of the group of protoporphyrinogen oxi selected from the group consisting of imazapyr, imaZamox, dase inhibitors, imaZaquin, imazapic, imazethapyr, their agriculturally C.3) herbicides of the group of auxins, acceptable salts and mixtures thereof. C.4) herbicides of the group of 4-hydroxyphenylpyruvate 41. The herbicidal composition as claimed in claim 33, dioxygenase inhibitors, wherein the at least one further herbicide C comprises at least C.5) herbicides of the group of phytoene desaturase inhibi one auxin herbicide C.3, selected from the group consisting tors, of benzoic acid herbicides. C.6) herbicides of the group of photosystem II inhibitors, 42. The herbicidal composition as claimed in claim 41, C.7) herbicides of the group of microtubulin inhibitors, and wherein the at least one auxin herbicide C.3 is dicamba or an C.8) herbicides of the group of VLCFA inhibitors. agriculturally acceptable salt thereof. 34. The herbicidal composition as claimed in claim 33, 43. The herbicidal composition as claimed in claim 33, wherein the at least one further herbicide C comprises at least wherein the at least one further herbicide C comprises at least one acetolactate synthase inhibitor C. 1, selected from the one 4-hydroxyphenyl-pyruvate-dioxygenase inhibitor C.4. group of imidazolinone herbicides. selected from the group consisting of mesotrione, Sulcotri 35. The herbicidal composition as claimed in claim 34, one, tembotrione, isoxaflutole and toprameZone. wherein the at least one acetolactate synthase inhibitor C.1 is selected from the group consisting of imazapyr, imaZamox, 44. The herbicidal composition as claimed in claim 33, imaZaquin, imazapic, imazethapyr, their agriculturally wherein the at least one further herbicide C comprises at least acceptable salts and mixtures thereof. one phytoene desaturase inhibitor C.5, selected from the 36. The herbicidal composition as claimed in claim 33, group of pyridine carboxamide herbicides. wherein the at least one further herbicide C comprises at least 45. The herbicidal composition as claimed in claim 44, one protoporphyrinogen oxidase inhibitor C.2, selected from wherein the at least one phytoene desaturase inhibitor C.5 is the group consisting of pyrimidindione herbicides and selected from the group consisting of diflufenican, picolin N-phenylphthalimide herbicides. afen their agriculturally acceptable salts and mixtures 37. The herbicidal composition as claimed in claim 36, thereof. wherein the at least one protoporphyrinogen oxidase inhibitor 46. The herbicidal composition as claimed in 33, wherein C.2 is selected from the group consisting of saflufenacil, the at least one further herbicide C comprises at least one flumioxazin, the agriculturally acceptable salts thereof and photosystem II inhibitor C.6, selected from the group con mixtures thereof. sisting of chlorotriazine herbicides, triazin(di)one herbicdes, 38. The herbicidal composition as claimed in claim 36, methylthiotriazine herbicides and urea herbicides. comprising in addition to the at least one protoporphyrinogen 47. The herbicidal composition as claimed in claim 46, oxidase inhibitor C.2 at least one further herbicide compound wherein the at least one photosystem II inhibitor C.6 is C, which is selected from the group consisting of selected from the group consisting of atrazine, terbuthylazin, US 2011/0065579 A1 Mar. 17, 2011 48 ametryn, hexaZinone, metribuzin, diuron, isoproturon, ter 55. The method as claimed in claim 53, wherein the herbi buthiuron and their agriculturally acceptable salts and mix cide A is applied in an amount from 50 ga.i./ha to 2000 g tures thereof. a.i./ha. 48. The herbicidal composition as claimed in claim 33, 56. The method as claimed in claim 53, wherein the herbi wherein the at least one further herbicide C comprises at least cide B is applied in an amount from 1 ga.i./ha to 500 ga.i./ha. one microtubulin inhibitor C.7., selected from the group con 57. The method as claimed in claim 53, which further sisting of dinitroaniline herbicides. comprises applying a herbicide C prior to and/or after plant 49. The herbicidal composition as claimed in claim 48, ing of the crop, wherein the herbicide C is selected from the wherein the at least one microtubulin inhibitor C.7 is pen group consisting of: dimethalin or ory Zalin. 50. The herbicidal composition as claimed in claim 33, C.1) herbicides of the group of acetolactate synthase wherein the at least one further herbicide C comprises at least inhibitors, one VLCFA inhibitor C.8, selected from the group consisting C.2) herbicides of the group of protoporphyrinogen oxi of chloroacetamide herbicides. dase inhibitors, 51. The herbicidal composition as claimed in claim 50, C.3) herbicides of the group of auxins, wherein the at least one VLCFA inhibitor C.8 is selected from C.4) herbicides of the group of 4-hydroxyphenylpyruvate the group consisting of dimethenamid, flufenacet and dioxygenase inhibitors, metaZachlor. C.5) herbicides of the group of phytoene desaturase inhibi 52. A method for controlling undesirable vegetation, which tors, method comprises applying a composition according to claim C.6) herbicides of the group of photosystem II inhibitors, 31 to a locus where undesirable vegetation is present or is expected to be present. C.7) herbicides of the group of microtubulin inhibitors, and 53. A method for burndown treatment of undesirable veg C.8) herbicides of the group of VLCFA inhibitors. etation in crops, comprising applying 58. The method as claimed in claim 53, wherein the crop is a) at least one herbicide A selected from glyphosate, glu selected from the group consisting of rice, maize, pulse crops, fosinate and their salts, and cotton, canola, Small grain cereals, soybeans, peanut, Sugar b) a herbicide B which is 3-5-(difluoromethoxy)-1-me cane, Sunflower, plantation crops, tree crops, nuts and grapes. thyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl-4, 59. The method as claimed in claim 53, wherein the crop is 5-dihydro-5,5-dimethyl-1,2-oxazole, selected from herbicide tolerant crops. to a locus where crops will be planted before planting or 60. The method as claimed in claim 56, further comprising emergence of the crop. applying the at least one herbicide A and the herbicide B after 54. The method as claimed in claim 53, wherein the at least planting and/or emergence of the crops. one herbicide A and the herbicide B are applied at a date up to 9 month prior to planting the crop. c c c c c