US 2011 OO15068A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0015068 A1 Sievernich et al. (43) Pub. Date: Jan. 20, 2011

(54) HERBICIDAL COMPOSITIONS Related U.S. Application Data COMPRISING PYROXASULFONE V (60) Provisional application No. 61/037,144, filed on Mar. 17, 2008, provisional application No. 61/118,803, (75) Inventors: Bernd Sievernich, Hassloch (DE); filed on Dec. 1, 2008. Anja Simon, Weinheim (DE); Publication Classification William Karl Moberg, Hassloch (51) Int. Cl. (DE); Richard R. Evans, Raleigh, AOIN 43/64 (2006.01) NC (US) AOIN 43/54 (2006.01) AOIN 43/56 (2006.01) Correspondence Address: AOIN 43/40 (2006.01) BRINKS, HOFER, GILSON & LIONE AOIPI3/00 (2006.01) P.O. BOX 110285 AOIPI3/02 (2006.01) RESEARCH TRIANGLE PARK, NC 27709 (US) (52) U.S. Cl...... 504/134: 504/136:504/139; 504/130 (57) ABSTRACT (73) Assignee: BASF SE, Ludwigshafen (DE) The present invention relates to herbicidally active composi tions, which comprise 3-5-(difluoromethoxy)-1-methyl-3- (trifluoromethyl)pyrazol-4-ylmethylsulfonyl-4,5-dihydro (21) Appl. No.: 12/922,811 5,5-dimethyl-1,2-oxazole common name pyroxasulfone and at least one B which is an selected from proto porphyrinogen-IX-Oxidase inhibitors. (22) PCT Filed: Mar. 16, 2009 The invention furthermore relates to the use of a composition as defined herein for controlling undesirable vegetation in (86). PCT No.: PCT/EP2009/053076 crops. When using the compositions of the invention for this purpose the herbicide A and the at least one herbicide B can be S371 (c)(1), applied simultaneously or in Succession in crops, where unde (2), (4) Date: Sep. 15, 2010 sirable vegetation may occur. US 2011/OO15068 A1 Jan. 20, 2011

HERBICIDAL COMPOSITIONS 0010 Unfortunately, it is usually not possible to predict COMPRISING PYROXASULFONE V synergistic activity for combinations of known , even if the compounds show a close structural similarity to known synergistic combinations. 0001. The present invention relates to herbicidally active compositions, which comprise 3-5-(difluoromethoxy)-1- SUMMARY OF THE INVENTION methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl-4,5- dihydro-5,5-dimethyl-1,2-oxazole common name pyroxas 0011. It is an object of the present invention to provide ulfone and at least one herbicide B. herbicidal compositions, which show enhanced herbicide action in comparison with the herbicide action of pyroxasul BACKGROUND OF THE INVENTION fone against undesirable harmful plants, in particular against Alopecurus myosuroides, Avena fatua, Bromus spec. Echin 0002. In crop protection, it is desirable in principle to ocloa spec. Lolium spec., Phalaris spec. Setaria spec. Digi increase the specificity and the reliability of the action of taria spec. Brachiaria spec. Amaranthus spec., Chenopo active compounds. In particular, it is desirable for the crop dium spec. Abutilon theophrasti, Galium aparine, Veronica protection product to control the harmful plants effectively spec., or Solanum spec. and/or to improve their compatibility and, at the same time, to be tolerated by the useful plants in with crop plants, in particular improved compatibility with question. wheat, barley, rye, rice, , Sunflower, brassica crops 0003. Pyroxasulfone has been described in EP-A 1364946 and/or cotton. The composition should also have a good her and US 2005/0256004. bicidal activity in post-emergence applications. The compo 0004 Although pyroxasulfone is a highly effective pre sitions should also show an accelerated action on harmful emergence herbicide, its activity at low application rates is plants, i.e. they should effect damaging of the harmful plants not always satisfactory. Moreover, pyroxasulfone is known to more quickly incomparison with application of the individual have only poor post-emergence activity (Y. Yamaji et al., herbicides. Application timing and field performance of KIH-485”. 0012 We have found that this object is achieved, surpris Conference Abstract I-1-ii-12B of 11. IUPAC International ingly, by herbicidally active compositions comprising Congress of Pesticide Chemistry, 2006 Kobe, Japan). Apart 0013 a) pyroxasulfone, i.e. 3-5-(difluoromethoxy)-1- from that, its compatibility with certain dicotyledonous crop methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl plants such as cotton, Sunflower, soybean, brassica crops such as canola and oilseed rape and some graminaceous plants 4,5-dihydro-5,5-dimethyl-1,2-oxazole (hereinafter also Such as rice, wheat, rye and barley is not always satisfactory, referred to as herbicide A); i.e. in addition to the harmful plants, the crop plants are also and damaged to an extent which is not acceptable. Though it is in 0014 b) at least one herbicide B which is an selected from principle possible to spare crop plants by lowering the appli protoporphyrinogen-IX-Oxidase inhibitors. cation rates, the extent of the control of harmful plants is 0015 The invention relates in particular to compositions naturally also reduced. in the form of herbicidally active compositions as defined 0005. It is known that combined application of certain above. different herbicides with specific action might result in an 0016. The invention furthermore relates to the use of a enhanced activity of a herbicide component in comparison composition as defined herein for controlling undesirable with a simple additive action. Such an enhanced activity is Vegetation. When using the compositions of the invention for also termed a synergism or synergistic activity. As a conse this purpose the herbicide A and the at least one herbicide B quence, it is possible to reduce the application rates of herbi can be applied simultaneously or in Succession, where unde cidally active compounds required for controlling the harmful sirable vegetation may occur. plants. 0017. The invention furthermore relates to the use of a 0006 WO 2005/104848 describes compositions contain composition as defined herein for controlling undesirable ing a herbicidal 3-sulfonylisoxazoline compound Such as Vegetation in crops. When using the compositions of the pyroxasulfone and a herbicide-antagonistically active invention for this purpose the herbicide A and the at least one amount of a safener. Similar compositions are known from herbicide B can be applied simultaneously or in Succession in WO 2007/006509. crops, where undesirable vegetation may occur. 0007 US 2005/256004, for example, discloses that in a 0018. The invention furthermore relates to the use of a pre-emergence treatment, joint application of certain herbi composition as defined herein for controlling undesirable cidal 3-sulfonylisoxazoline compounds, Such as pyroxasul Vegetation in crops which, by genetic engineering or by fone, with or results in an increased overall breeding, are resistant or tolerant to one or more herbicides herbicide action against certain monocotyledonous and and/or pathogens such as plant pathogenous fungi, and/or to dicotyledonous annual broadleaf weeds (lambsquarter, green attack by insects; preferably resistant or tolerant to one or foxtail, Velvetleaf) in comparison with a simple expected more herbicides that act as protoporphyrinogen-IX-oxidase additive action. inhibitors. 0008 WO 2006/097322 discloses a herbicidal composi 0019. The invention furthermore relates to a method for tion comprising pyroxasulfone and a second herbicide controlling undesirable vegetation, which comprises apply selected from tembotrione, toprameZone and 4-hydroxy-3- ing a herbicidal composition according to the present inven 2-(2-methoxyethoxy)methyl-6-(trifluoromethyl-3-py tion to the undesirable plants. Application can be done before, ridinylcarbonylbicyclo[3.2.1]oct-3-ene-2-one. during and/or after, preferably during and/or after, the emer 0009 WO 2006/097509 discloses a herbicidal composi gence of the undesirable plants. The herbicide A and the at tion comprising a herbicidal 3-sulfonylisoxazoline com least one herbicide B can be applied simultaneously or in pound such as pyroxasulfone and a phenyluracil compound. Succession. US 2011/OO15068 A1 Jan. 20, 2011

0020. The invention in particular relates to a method for 0036 Phenyluracil herbicides (group b. 1) include ben controlling undesirable vegetation in crops, which comprises Zfendizone and compounds of the formula I and the salts applying a herbicidal composition according to the present thereof, invention in crops where undesirable vegetation occurs or might occur. 0021. The invention furthermore relates to a method for (I) controlling undesirable vegetation, which comprises allow R2 ing a composition according to the present invention to act on plants, their habitat or on seed. R4 Het 0022. In the uses and methods of the present invention it is immaterial whether the herbicide A and the at least one her bicide Bareformulated and applied jointly or separately, and, RI R3 in the case of separate application, in which order the appli cation takes place. It is only necessary, that the herbicide A 0037 wherein and the at least one herbicide B are applied in a time frame, I0038) R' is selected from the group consisting of the which allows simultaneous action of the active ingredients on radicals propargyloxy, allyloxy, isopropyloxy, C(=O) the plants. NHSONR'R'', C(=O)N NR'R'', 0023 The invention also relates to an herbicide formula O CR'R' C(=O) OR'e, C(=O)C tion, which comprises a herbicidally active composition as CR'R' C(=O) OR, C(=O)C R', C(=O) defined herein and at least one carrier material, including O CHR's C(=O)NHSONR'R'', liquid and/or Solid carrier materials. NHSONR'R'', SONHC(=O)NR'R'', CH, CH (CI)CO. R'' and the radical of the formula OC(CH) DETAILED DESCRIPTION OF THE INVENTION C(=O) OR': where 0024 Surprisingly, the compositions according to the 0039) R' is hydrogen or C-C-alkyl: invention have better herbicidal activity against harmful 0040) R' is C-C-alkyl: plants than would have been expected by the herbicidal activ I0041) R' is hydrogen or C-C-alkyl; ity of the individual compounds. In other words, the joint I0042) R' is hydrogen or C-C-alkylor a agricultur action of pyroxasulfone and the at least one herbicide B ally acceptable cation; and results in an enhanced activity against harmful plants in the 10043 R' is C-C-alkyl, propargyl orallyl: sense of a synergy effect (synergism). For this reason, the 0044) R is hydrogen, fluorine or chlorine; compositions can, based on the individual components, be I0045 R is hydrogen ortogether with R' forms amoiety used at lower application rates to achieve a herbicidal effect - O C(R)=N or N=C(R) NH , where comparable to the individual components. Moreover, the 0046 RandR are selected, independently of each compositions of the present invention provide good post other, from hydrogen, C-C-alkyl, C-C-haloalkyl, emergence herbicidal activity, i.e. the compositions are par C-C-alkenyl, C-C-haloalkenyl, C-C-alkylnyl, ticularly useful for combating/controlling harmful plants C-C-haloalkylnyl, C-C-alkoxy, C-C-cycloalkyl after their emergence. Apart form that, the compositions of and C-C-alkyl substituted by a C-C-cycloalkyl the present invention show good crop compatibility, i.e. their radical; with R" and R preferably being selected, use in crops leads to a reduced damage of the crop plants independently of each other, from C-C-alkyl, and/or does not result in increased damage of the crop plants. C-C-haloalkyl, and C-C-alkyl substituted by a 0025. As used herein, the terms “controlling” and “com Ca-Ca-cycloalkyl radical with RandR more pref bating are synonyms. erably being selected, independently of each other, 0026. As used herein, the terms “undesirable vegetation' from methyl, ethyl, n-propyl, isopropyl. n-butyl, and “harmful plants' are synonyms. 2-methylpropyl, trifluoromethyl and cyclopropylm 0027. The compositions of the invention comprise pyroxa ethyl: Sulfone as a first componenta). I0047 R is halogen or cyano, in particular chlorine or 0028. As a second component b), the compositions of the fluorine; invention comprise at least oneherbicide B which is an inhibi 0048 and tor of protoporphyrinogen-IX-oxidase (PPO inhibitor). PPO 0049. Het is a heterocyclic radical of the formula A: inhibitors are compounds, which have a mode of action com prising the inhibition of a step of the biosynthesis in plants and which belong to the group E of the HRAC (A) classification system (see HRAC, Classification of Herbi cides According to Mode of Action, http://www.plantprotec tion.org/hrac/MOA.html). 0029. According to the present invention the PPO inhibi tor is preferably selected from the group consisting of 0030 b.1 phenyluracil and pyrazol type herbicides; 0031 b.2 triazolone and oxadiazolone herbicides; 0032 b.3 dicarboximide herbicides: 0050 where it indicates the point of attachment and 0033 b.4 nitrophenylether herbicides; and wherein 0034 b.5 triazindione herbicides; and 0051 R is selected from hydrogen amino, methyl or 0035 b.6 dicarboxamide herbicides. propargyl and wherein R is preferably methyl. US 2011/OO15068 A1 Jan. 20, 2011

0052 Pyrazole type herbicides (group b. 1) include com usually from 1 to 6 carbon atoms, preferably 1 to 4 carbon pounds of the formula I and the salts thereof, atoms. Examples of an alkoxy group are methoxy, ethoxy, n-propoxy, iso-propoxy, n-butyloxy, 2-butyloxy, iso-buty loxy, tert-butyloxy and the like. (I) 0058. The term “haloalkoxy” as used herein denotes in each case a straight-chain or branched alkoxy group having from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or R4 Het totally replaced with halogen atoms, in particular fluorine atoms. Preferred haloalkoxy moieties include C-C-ha loalkoxy, in particular C-C-fluoroalkoxy, such as fluo romethoxy, difluoro-methoxy, trifluoromethoxy, 1-fluoroet hoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2.2.2- wherein R', R, R and Rare as defined for formula I and trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2- wherein Het is a radical of the formula B difluoro-ethoxy, 2,2-dichloro-2-fluorethoxy, 2.2.2- trichloroethoxy, pentafluoroethoxy and the like. 0059. The term “cycloalkyl as used herein and in the R7 (B) cycloalkyl moieties of cycloalkyl-alkyl denotes in each case a R6 monocyclic Saturated carbocyclic radical having usually s from 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, it. cyclopenty1 and cyclohexyl. N e 0060. The term “alkenyl' as used herein denotes in each N1 NCH, case a singly unsaturated hydrocarbon radical having usually 3 to 6, or preferably 3 to 4 carbon atoms, such as vinyl, allyl where it indicates the point of attachment and wherein (2-propen-1-yl), 1-propen-1-yl, 2-propen-2-yl, methallyl R is selected from difluoromethoxy, trifluoromethyl and (2-methylprop-2-en-1-yl), 2-buten-1-yl, 3-buten-1-yl, methylsulfonyl: 2-penten-1-yl, 3-penten-1-yl 4-penten-1-yl, 1-methylbut-2- R’ is selected from halogen or methyl, in particular from en-1-yl, 2-ethylprop-2-en-1-yl and the like. chlorine or bromine. 0061. The term "haloalkenyl” as used herein denotes in 0053. The organic moieties mentioned in the above defi each case a straight-chain or branched alkenyl group, as nitions of the variables are—like the term halogen—collec defined above, having usually from 3 to 6 carbon atoms, tive terms for individual listings of the individual group mem preferably from 3 to 4 carbon atoms, wherein the hydrogen bers. The prefix C-C, indicates in each case the possible atoms of this group are partially or totally replaced with number of carbon atoms in the group. halogen atoms. 0054 The term halogen denotes in each case fluorine, 0062. The term “alkynyl as used herein denotes in each bromine, chlorine or iodine, in particular fluorine, chlorine or case a singly unsaturated hydrocarbon radical having usually bromine. from 3 to 6 carbon atoms, such as ethynyl, propargyl (2-pro 0055. The term “alkyl as used herein denotes in each case pyn-1-yl), 1-propyn-1-yl, 1-methylprop-2-yn-1-yl), 2-butyn a straight-chain or branched alkyl group having usually from 1-y1,3-butyn-1-yl, 1-pentyn-1-yl, 3-pentyn-1-yl 4-pentyn-1- 1 to 6 carbon atoms, preferably from 1 to 4 carbon atoms, yl, 1-methylbut-2-yn-1-yl, 1-ethylprop-2-yn-1-yl and the more preferably from 1 to 3 carbon atoms. Examples of an like. alkyl group are methyl, ethyl, n-propyl, iso-propyl. n-butyl, 0063. The term “haloalkynyl as used herein denotes in 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-me each case a straight-chain or branched alkynyl group, as thylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl. defined above, having usually from 3 to 6 carbon atoms, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methyl preferably from 3 to 4 carbon atoms, wherein the hydrogen pentyl, 2-methylpenty1.3-methylpentyl, 4-methylpentyl, 1.1- atoms of this group are partially or totally replaced with dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2.2- halogen atoms. dimethylbutyl, 2,3-dimethylbutyl, 3.3-dimethylbutyl, 0064. The term “alkyl substituted by analkoxy radical as 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1.2.2-trim used herein refers to linear or branched alkyl having usually 1 ethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methyl to 4 carbonatoms, wherein 1 of those carbonatoms carries an propyl. alkoxy radical usually having 1 to 4 carbon atoms. Examples 0056. The term “haloalkyl as used herein denotes in each are CHOCH, CH, OCHs, n-propoxymethyl, CH case a straight-chain or branched alkyl group having usually OCH(CH), n-butoxymethyl, (1-methylpropoxy)-methyl, from 1 to 6 carbon atoms, preferably from 1 to 4 carbon (2-methylpropoxy)methyl, CH2—OC(CH), 2-(methoxy) atoms, wherein the hydrogenatoms of this group are partially ethyl, 2-(ethoxy)ethyl 2-(n-propoxy)-ethyl, 2-(1-methyl or totally replaced with halogen atoms. Preferred haloalkyl ethoxy)-ethyl, 2-(n-butoxy)ethyl 2-(1-methylpropoxy)- moieties are selected from C-C-haloalkyl, more preferably ethyl, 2-(2-methylpropoxy)-ethyl, 2-(1,1-dimethylethoxy)- from C-C-haloalkyl, in particular from C-C-fluoroalkyl ethyl, 2-(methoxy)-propyl. 2-(ethoxy)-propyl, 2-(n- such as fluoromethyl, difluoromethyl, trifluoromethyl, propoxy)-propyl. 2-(1-methylethoxy)-propyl. 2-(n-butoxy)- 1-fluoroethyl 2-fluoroethyl, 2,2-difluoroethyl, 2.2.2-trifluo propyl. 2-(1-methylpropoxy)-propyl, 2-(2-methylpropoxy)- roethyl, pentafluoroethyl and the like. propyl. 2-(1,1-dimethylethoxy)-propyl, 3-(methoxy)-propyl. 0057 The term “alkoxy” as used herein denotes in each 3-(ethoxy)-propyl, 3-(n-propoxy)-propyl, 3-(1-methyl case a straight-chain or branched alkyl group which is bound ethoxy)-propyl, 3-(n-butoxy)-propyl, 3-(1-methylpropoxy)- via an oxygenatomat any position in the alkyl group and has propyl, 3-(2-methylpropoxy)-propyl, 3-(1,1-dimethyl US 2011/OO15068 A1 Jan. 20, 2011

ethoxy)-propyl. 2-(methoxy)-butyl, 2-(ethoxy)-butyl, 2-(n- 0077 saflufenacil propoxy)-butyl, 2-(1-methylethoxy)-butyl, 2-(n-butoxy)- (CH)), R°—F), butyl, 2-(1-methylpropoxy)-butyl, 2-(2-methyl-propoxy)- butyl, 2-(1,1-dimethylethoxy)-butyl, 3-(methoxy)-butyl, with a particular preference given to saflufenacil. 3-(ethoxy)-butyl, 3-(n-propoxy)-butyl, 3-(1-methylethoxy)- 0078. According to another preferred embodiment of the butyl, 3-(n-butoxy)-butyl, 3-(1-methylpropoxy)-butyl, 3-(2- invention the phenyluracil herbicides (group b. 1) are selected methylpropoxy)-butyl, 3-(1,1-dimethylethoxy)-butyl, from compounds of the formula Ib and the salts thereof, 4-(methoxy)-butyl, 4-(ethoxy)-butyl, 4-(n-propoxy)-butyl, 4-(1-methylethoxy)-butyl, 4-(n-butoxy)-butyl, 4-(1-methyl propoxy)-butyl, 4-(2-methylpropoxy)-butyl, 4-(1,1-dimeth ylethoxy)-butyl and the like. 0065. The term “alkyl substituted by cycloalkyl radical as (Ib) used herein refers to linear or branched alkyl having usually 1 to 2 carbon atoms, wherein 1 of those carbon atoms carries a cycloalkyl radical usually having 3 to 6 carbon atoms. Examples are CH-cylcopropyl (cyclopropylmethyl), CH cylcobutyl (-cyclobutylmethyl), CH-cylcopentyl (cyclo pentylmethyl), CH-cylcohexyl (cyclohexylmethyl), CHCH-cylcopropyl (2-cyclopropylethyl), CHCH-cyl cobutyl (=2-cyclobutylethyl), CHCH-cylcopentyl (=2-cy clopentylethyl), CHCH-cylcohexyl (=2-cyclohexylethyl), CH(CH)-cylcopropyl (=1-cyclopropylethyl), CH(CH)-cyl cobutyl (=1-cyclobutylethyl), CH(CH)-cylcopentyl (=1-cy clopentylethyl) or CH(CH)-cylcohexyl (=1-cyclohexyl wherein R. R. RandR areas defined herein, and wherein ethyl). R. R. R. and R, independently of each other, and more preferably in combination have one of the following mean 0066. According to a preferred embodiment of the inven ings tion, the phenyluracilherbicides (group b. 1) are selected from benzfendizone and compounds of the formula Ia and the salts R’ is preferably fluorine or chlorine, thereof, R" is preferably chlorine, R is preferably methyl and R" is preferably selected from C-C-alkyl, C-C-haloalkyl, (I) and C-C2-alkyl Substituted by a C-C-cycloalkyl radical with R" being more preferably selected from methyl, ethyl, n-propyl, isopropyl. n-butyl, 2-methylpropyl, trifluoromethyl and cyclopropylmethyl. 0079. Examples of particularly preferred compounds of formula Ib are selected from the group of compounds of the formula Ib, wherein 0080 R is fluorine, R is chlorine, R is methyland R' wherein is cyclopropylmethyl, I0067) R' is selected from the group consisting of the 0081) R' is chlorine, R is chlorine, R is methyland R' radicals propargyloxy, allyloxy, iso-propyloxy, C(=O) is cyclopropylmethyl, NHSONR'R'', C(=O)N NR'R'', C(=O)C CR'R' C(=O) OR, C(=O)C R', C(=O) I0082 R is fluorine, R is chlorine, R is methyland R' O CHR' C(=O)NHSONR'R'', is methyl, NHSONR'R'', SONHC(=O)NR'R'', CH, CH 0.083 R’ is chlorine, R is chlorine, R is methyland R' (CI)CO. R'' and the radical of the formula OC(CH) is methyl, C(=O) OR'; where 0084 R is fluorine, R is chlorine, R is methyland R' I0068 R'' is hydrogen or C-C-alkyl: is ethyl, 0069) R' is C-C-alkyl: I0085 R is chlorine, R is chlorine, R is methyland R' I0070) R' is hydrogen or C-C-alkyl; is ethyl, (0071) R' is hydrogen or C-C-alkyl or a agricultur I0086) R is fluorine, R is chlorine, R is methyland R' ally acceptable cation; and is trifluoromethyl or I0072 R is C-C-alkyl, propargyl or allyl; and 0087 R’ is chlorine, R is chlorine, R is methyland R' 0073 R’ is hydrogen, fluorine or chlorine. is trifluoromethyl. 0074 Examples of particularly preferred compounds of I0088 An especially preferred compound of this embodi formula Ia include ment is a compound of the formula Ib, wherein R is fluorine, 0075 (R'=C(=O)C C(CH) C R" is chlorine, R is methyl and R is cyclopropylmethyl. (=O) OCH-CH=CH, R—H), I0089. According to another preferred embodiment of the (0076 flupropacil (R-C(=O)C) CH(CH), R—H), invention the phenyluracil herbicides (group b. 1) are selected and from compounds of the formula Id and the salts thereof, US 2011/OO15068 A1 Jan. 20, 2011

(Id) (Ic)

R3 wherein R. R. R. R. and R7 are as defined herein, and wherein R. R. RandR areas defined herein, and wherein wherein R. R. R. Rand R", independently of each other, R. R. R. and R, independently of each other, and more and more preferably in combination have one of the following preferably in combination have one of the following mean meanings ings R’ is preferably fluorine or chlorine, R’ is preferably fluorine or chlorine, R" is preferably chlorine, R" is preferably chlorine, R is preferably difluoromethoxy, R’ is preferably chlorine or bromine and R is preferably methyl and R is preferably selected from C-C-alkyl, C-C-haloalkyl, R is preferably selected from C-C-alkyl, C-C-haloalkyl, and C-C2-alkyl Substituted by a C-C-cycloalkyl radical and C-C-alkyl substituted by a C-C-cycloalkyl radical with R being more preferably selected from methyl, ethyl, with R" being more preferably selected from methyl, ethyl, n-propyl, isopropyl. n-butyl, 2-methylpropyl, trifluoromethyl n-propyl, isopropyl. n-butyl, 2-methylpropyl, trifluoromethyl and cyclopropylmethyl. and cyclopropylmethyl. 0102) Examples of particularly preferred compounds of 0090. Examples of particularly preferred compounds of formula Ic are selected from the group of compounds of the formula Ic, wherein formula Id are selected from the group of compounds of the (0103 R’ is fluorine, R is chlorine, R is difluo formula Id, wherein romethoxy, R is chlorine and R is ethyl, (0091 R is fluorine, R is chlorine, R is methylandR 0104 R is chlorine, R is chlorine, R is difluo is cyclopropylmethyl, romethoxy, R is chlorine and R is ethyl, 0092 R is chlorine, R is chlorine, R is methylandR 0105 R is fluorine, R is chlorine, R is difluo is cyclopropylmethyl, romethoxy, R is bromine and R is ethyl, or (0093 R’ is fluorine, R is chlorine, R is methylandR 0106 R is chlorine, R is chlorine, R is difluo is methyl, romethoxy, R is bromine and R is ethyl. (0094) R is chlorine, R is chlorine, R is methylandR 0107 According to a further preferred embodiment of the is methyl, invention, the pyrazole type herbicides (group b. 1) are selected from compounds of the formula Ie and the salts 0095 R is fluorine, R is chlorine, R is methylandR thereof, is ethyl, (0096 R is chlorine, R is chlorine, R is methylandR

is ethyl, (Ie) 0097 R’ is fluorine, R is chlorine, R is methylandR is trifluoromethyl or (0098 R is chlorine, R is chlorine, R is methylandR is trifluoromethyl. 0099. An especially preferred compound is a compound of the formula Id, wherein R is fluo-rine, R is chlorine, R is methyl and R is trifluoromethyl. 0100 Phenyluracil herbicides and pyrazole type herbi wherein cides (group b.1) are known from e.g. G. Theodoridis “Pro I0108) R' is selected from the group consisting of the radi toporphyrinogen-IX-oxidase Inhibitors' in “Modern Crop cals propargyloxy, allyloxy, isopropyloxy, C(=O) Protection Compounds' Vol. 1, Wiley-VHC 2007, pp 153 NHSONR'R'', C(O)N NR'R'', O CR'R's C 186: C. D. S. Tomlin, “The Pesticide Manual, 13th Edition, BCPC (2003), and also from The Compendium of Pesticide Common Names http://www.alanwood.net/pesticides/. NR'R'', CH, CH(CDCO, R'' and the radical of the 0101. According to another preferred embodiment of the formula OC(CH), C(=O) OR'; where invention the pyrazole type herbicides (group b. 1) are 0109) R' is hydrogen or C-C-alkyl: selected from compounds of the formula Ic and the salts 0110) R' is C-C-alkyl: thereof, I0111) R' is hydrogen or C-C-alkyl; US 2011/OO15068 A1 Jan. 20, 2011

I0112) R' is hydrogen or C-C-alkylora agriculturally I0129. Dicarboximide herbicides (b.3) include compounds acceptable cation; and of the formula III, 0113 R" is C-C-alkyl, propargyl or allyl; 0114 R’ is hydrogen, fluorine or chlorine; (III) 0115 R is selected from difluoromethoxy, trifluorom ethyl and methylsulfonyl; and 0116 R7 is selected from halogen or methyl, in particular from chlorine or bromine. 0117 Examples of particularly preferred compounds of R 14 O formula Ie include 0118 fluazolate (R'=C(=O)C)-CH(CH), R=F, wherein R'-trifluoromethyl, R'-bromine), and I0130) R' is hydrogen, fluorine or chlorine; 0119 pyraflufen-ethyl (R'=O CH C(=O)C)— I0131) R' is selected from the group consisting of propar CHCH, R=F, R=difluoromethoxy, R7-chlorine). gyloxy, allyloxy, 1-methyl-2-propinyloxy, O—CH2CO R", CHC(Cl)CO R'' and isopropyloxy: 0120 Triazolone and oxadiazolone herbicides (b.2) (0132) R' is fluorine or chlorine; or include in particular compounds of the formula II and their 0.133 R'' and R' together form a moiety O CH-C salts, (=O) NR'', where R'' is a propargyl radical and where the oxygenatom is meta with regard to the position of R: 10134) R' is hydrogen, C-C-alkyl or an agriculturally (II) acceptable cation. 0.135 Examples of compounds of formula III include cini don, flumioxazin, flumiclorac, and flumipropyn. Also included are the salts ofcinidon and flumiclorac, in particular C N their sodium salts, potassium salts, ammonium salts or Sub N-lN stituted ammonium salts as defined above, in particular R10 mono-, diand tri-C-C-alkylammonium salts such as isopro R8 pylammonium salts, and the esters of cinidon and flumiclo 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. 0121 X is O or NR'', 0.136 Dicarboximide herbicides (group b.3) are known I0122 R is selected from the group consisting of propar from e.g. G. Theodoridis “Protoporphyrinogen-IX-oxidase Inhibitors' in “Modern Crop Protection Compounds' Vol. 1, gyloxy, allyloxy, isopropyloxy, the radical of the formula Wiley-VHC 2007, pp 153-186: C. D. S. Tomlin, “The Pesti CH-CH(CI)CO R'' and the radical of the formula cide Manual, 13th Edition, BCPC (2003), and also from The NH SO CH: Compendium of Pesticide Common Names http://www.alan (0123 R is fluorine or chlorine; wood.net/pesticides/. I0137 Nitrophenylether herbicides (b.4) include furylox 0124) R' is CH, tert-butyl: yphen and compounds of the formula IV. 0125 R'' is CHF2, or together with R' may for 1,4- butandiyl: IV I0126) R' is hydrogen, C-C-alkyl or a agriculturally C R19 (IV) acceptable cation. 0127 Examples of the compounds of formula I include aZafenidin, carfentraZone, , oxadiazon and oxa diargyl. Also included are the salts of carfentraZone, in par ticular its sodium salt, potassium salt, ammonium salt or R20 Substituted ammonium salts as defined above, in particular mono-, diand tri-C-C-alkylammonium salts such as isopro wherein pylammonium salts and the esters of carfentraZone, in par 0.138) R' is chlorine or trifluoromethyl: ticular its C-C-alkyl esters, such as methylesters, ethylest I0139) R' is selected from the group consisting of hydro ers, isopropyl esters. A Suitable example of Such an ester is gen, C-C-alkoxy, CO. R', C(=O)C CH-CO, carfentraZone-ethyl. R',C(=O)C CH(CH)CO R', C(=O)NH SO, R: 0128 Triazolone and oxadiazolone herbicides (group b.2) I0140) R' is hydrogen, fluorine or chlorine; are known from e.g. G. Theodoridis “Protoporphyrinogen I014.1) R' is hydrogen, C-C-alkyl or a agriculturally IX-oxidase Inhibitors' in “Modern Crop Protection Com acceptable cation; and pounds' Vol. 1, Wiley-VHC 2007, pp 153-186: C. D. S. 0.142 R’ is C-C-alkyl. Tomlin, “The Pesticide Manual”, 13th Edition, BCPC (2003), 0143. Examples of compounds of formula IV include and also from The Compendium of Pesticide Common , , oxyfluorfen, , fluoroglycofen, Names http://www.alanwood.net/pesticides/. fluorodifen, , , halosafen, chlornitrofen, US 2011/OO15068 A1 Jan. 20, 2011

fluornitrofen, chlomethoxyfen and nitrofluorfen and their 0154 Dicarboxamide type herbicides (group b.6) include salts and esters. In particular included are the salts of acifluo e.g. compounds of the formula VI and the salts thereof, 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 esters of acifluorfen and fluoroglycofen, in particular their (VI) C-Cs-alkyl esters, such as methylesters, ethylesters, isopro 21 pyl esters. A Suitable example of Such a salt is acifluorfen - H(R), sodium. Suitable examples of such esters are acifluorfen methyl and fluoro-glycofen-ethyl. 1S 0144. Nitrophenylether herbicides (group d.) are known -N O from e.g. G. Theodoridis “Protoporphyrinogen-IX-oxidase (R8), H Inhibitors' in “Modern Crop Protection Compounds' Vol. 1, N.4Neo Wiley-VHC 2007, pp 153-186: C. D. S. Tomlin, “The Pesti N cide Manual, 13th Edition, BCPC (2003), and also from The Compendium of Pesticide Common Names http://www.alan HNN R27 wood.net/pesticides/. 0145 Triazinedione type herbicides (group b.5) include wherein e.g. compounds of the formula V and the salts thereof, 0155 m is 0, 1, 2, or 3, in particular 1 or 2: 0156 n is 0, 1, 2, 3 or 4, in particular 1 or 2: (O157 R’ is selected from C-C-alkyl, C-Ca-haloalkyl, (V) C-C-alkenyl, C-C-haloalkenyl, C-C-alkylnyl, R23 O R25 C-C-haloalkylnyl, C-C-cycloalkyl, C-C-alkyl Sub N stituted by a C-C-alkoxy radical, and C-C-alkyl Sub X-X stituted by a C-C-cycloalkyl radical; O N )=y I0158 R is selected from halogen, C-C-alkyl, C-C- y-NM haloalkyl, C-C-alkoxy, and C-C-alkyl substituted by a N O R26 C-C-alkoxy radical, it being possible for m=2 or 3 that O Ye the radicals R are identical or different from each other, 10159 R’ is selected from halogen, cyano, nitro, C-C- wherein alkyl, C-Ca-haloalkyl, C-C-alkylsulfonyl, C-C- alkoxy, C-C-alkyl substituted by a C-C-alkoxy radical, 0146) R' is hydrogen, fluorine or chlorine; C-C2-alkyl Substituted by a C-C-cycloalkyl radical and 0147 R’ is selected from hydrogen, C-C-alkyl, C-C- a radical CO.R.", it being possible for n=2, 3 or 4 that the haloalkyl, C-C-alkenyl, C-C-haloalkenyl, C-C-alky radicals R are identical or different from each other; nyl, C-C-haloalkynyl, C-C-alkoxy, C-C-cycloalkyl (0160) R' is selected from C-C-alkyl, C-Ca-haloalkyl, and C-C-alkyl substituted by a C-C-cycloalkyl radical; C-C-alkenyl, C-C-haloalkenyl, C-C-alkylnyl, 0148 R is selected from hydrogen, amino, methyl and C-C-haloalkylnyl, C-C-cycloalkyl, C-C-alkyl Sub propargyl; stituted by a C-C-alkoxy radical and C-C2-alkyl Substi 0149 R is selected from hydrogen and methyl: tuted by a C-C-cycloalkyl radical. O150 and Y is O or S. 0.161 Preference is given to compounds of the formula VI, 0151. Preference is given to compounds of the formula V. wherein m, n, R7, R7, Rand R', independently of each wherein Y. R. R. R and R, independently of each other, and more preferably in combination have one of the other, and more preferably in combination have one of the following meanings: following meanings: (0162 m is 1: (0163 n is 1, 2 or 3: Y is S, (0164) R' is selected from C-C-alkyl, Ca-Ca-cycloalkyl, 0152 R is preferably fluorine or chlorine, and C-C2-alkyl Substituted by a C-C-cycloalkyl radical, R" is preferably Cs-Co-alkyl, Cs-Co-alkenyl, or Cs-Co-alky in particular cyclopropylmethyl; nyl, in particular C-C-alkynyl, and especially propargyl. (0165 R is selected from halogen and C-C-alkyl, in R’ is preferably methyl, and particular methyl; R’ is preferably methyl. (0166 R’ is selected from halogen, C-C-alkyl and a 0153. In a particular preferred compound of the formula V radical CO.R.", it being possible for n=2 or 3 that the the variable Y is S, R’ is fluorine, R is propargyl, R is radicals R are identical or different from each other; methyl and R is methyl. (0167 R is C-C-alkyl. US 2011/OO15068 A1 Jan. 20, 2011

0168 A particular preferred compound of the formula VI fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic is the compound of the following formula VIa: anhydride, 2.2.5-trimethyl-3-(dichloroacetyl)-1,3-oxazoli dine, and 4-(dichloroacetyl)-1-Oxa-4-azaspiro4.5 decane and oxabetrinil; and the agriculturally acceptable salt thereof (VIa) and, in the case of compounds having a COOH group, an HC agriculturally acceptable derivative as defined below. 0176 A preferred embodiment of the invention relates to compositions which contain no safener or virtually no safener HN C (i.e. less than 1% by weight, based on the total amount of herbicide A and the at least one herbicide B is applied). N O CO2-CH 0177. The compositions of the invention may also com prise, as a componentd), one or more herbicides D) which are 2 O different from the herbicides A and B. Such further herbicides H3C N D may broaden the activity spectrum of the inventive com positions. However, further herbicides D are generally not ruA required. Therefore, a preferred embodiment of the invention relates to compositions which contain no further herbicide D 0169. In the compositions of the present invention the or virtually no further herbicide D (i.e. less than 1% by relative weight ratio of pyroxasulfone to herbicide B is pref weight, based on the total amount of herbicide A and herbi erably in the range from 1:500 to 500:1, in particular in the cide B). range from 1:250 to 250:1 and more preferably from 100:1 to 0178. In particular, the compositions of the present inven 1:100. Accordingly, in the methods and uses of the invention, pyroxasulfone and the at least one herbicide B are applied tion consist of the herbicide A and the at least one herbicide B, within these weight ratios. i.e. they neither contain a safener nor a further herbicide D. 0170 The compositions of the invention may also com 0179 If the compounds of herbicide compounds men prise, as a component c), one or more Safeners. Safeners, also tioned as herbicides B, herbicides D and safeners (see below) termed as herbicide Safeners, are organic compounds which have functional groups, which can be ionized, they can also be in Some cases lead to better crop plant compatibility when used in the form of their agriculturally acceptable salts. In applied jointly with specifically acting herbicides. Some general, the salts of those cations are Suitable whose cations safeners are themselves herbicidally active. In these cases, the have no adverse effect on the action of the active compounds safeners act as antidote or antagonist in the crop plants and ("agricultural acceptable'). thus reduce or even prevent damage to the crop plants. How 0180. In general, the salts of those cations are suitable ever, in the compositions of the present invention, Safeners are whose cations have no adverse effect on the action of the generally not required. Therefore, a preferred embodiment of active compounds (“agricultural acceptable'). Preferred cat the invention relates to compositions which contain no ions are the ions of the alkali metals, preferably of lithium, safener or virtually no safener (i.e. less than 1% by weight, Sodium and potassium, of the alkaline earth metals, prefer based on the total amount of herbicide A and herbicide B). ably of calcium and magnesium, and of the transition metals, 0171 Suitable safeners, which can be used in the compo sitions according to the present invention, are known in the preferably of manganese, copper, Zinc and iron, furthermore art, e.g. from ammonium and Substituted ammonium (hereinafter also 0172. The Compendium of Pesticide Common Names termed as organoammonium) in which one to four hydrogen (http://www.alanwood.net/pesticides/); Farm Chemicals atoms are replaced by C-C-alkyl, hydroxy-C-C-alkyl, Handbook 2000 Vol. 86, Meister Publishing Company, C-C-alkoxy-C-C-alkyl, hydroxy-C-C-alkoxy-C-C- 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide, Georg alkyl, phenyl or benzyl, preferably ammonium, methylam Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide monium, isopropylammonium, dimethylammonium, diiso Handbook, 7th Edition, Weed Science Society of America, propylammonium, trimethylammonium, 1994; and tetramethylammonium, tetraethylammonium, tetrabutylam 0173 K. K. Hatzios, Herbicide Handbook, Supplement to monium, 2-hydroxyethylammonium (olamine salts), 2-(2- 7th Edition, Weed Science Society of America, 1998. hydroxyethoxy)eth-1-ylammonium (diglycolamine salts), 0174 Safeners include e.g. benoxacor, cloquintocet, cyo di (2-hydroxyeth-1-yl)ammonium (diolamine salts), tris(2- metrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, hydroxyeth-1-yl)ammonium (trolamine salts), tris(3-pro fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, panolammonium, benzyltrimethylammonium, benzyltri isoxadifen, mefenpyr, mephenate, naphthalic anhydride, 2.2, ethylammonium, furthermore phosphonium ions, Sulfonium 5-trimethyl-3-(dichloracetyl)-1,3-oxazolidine, 4-(dichloro ions, preferably tri(C-C-alkyl)sulfonium Such as trimethyl acetyl)-1-Oxa-4-azaspiro4.5 decane and oxabetrinil, as well Sulfonium, and Sulfoxonium ions, preferably tri(C-C-alkyl) as thereof agriculturally acceptable salts and, provided they Sulfoxonium. have a carboxyl group, their agriculturally acceptable deriva 0181. In the compositions according to the invention, the tives. 2.2.5-Trimethyl-3-(dichloroacetyl)-1,3-oxazolidine compounds that carry a carboxyl group can also be employed CAS No. 52836-31-4 is also known under the name in the form of agriculturally acceptable derivatives, for R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro4.5 decane example as such as mono- or di-C-C-alkylamides or CAS No. 71526-07-03 is also known under the names arylamides, as esters, for example as allyl esters, propargyl AD-67 and MON 4660. esters, C-Co-alkyl esters or alkoxyalkyl esters, and also as 0.175. As a safener, the compositions according to the thioesters, for example as C-Co-alkylthioesters. Preferred invention particularly preferably comprise at least one of the mono- and di-C-C-alkylamides are the methyl- and the compounds selected from the group of benoxacor, cloquin dimethylamides. Preferred arylamides are, for example, the tocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, anilidines and the 2-chloroanilides. Preferred alkyl esters are, US 2011/OO15068 A1 Jan. 20, 2011 for example, the methyl, ethyl, propyl, isopropyl, butyl, (T. dicoccon) and spelt (T. spelta), rye (Secale cere isobutyl, pentyl, mexyl (1-methylhexyl) or isooctyl (2-ethyl ale), triticale (Tritiosecale), barley (Hordeum vul hexyl) esters. Preferred C-C-alkoxy-C-C-alkyl esters are gare); the straight-chain or branched C-C-alkoxyethyl esters, for 0188 maize (corn: Zea mays); example the methoxyethyl, ethoxyethyl or butoxyethyl 0189 sorghum (e.g. Sorghum bicolour); esters. An example of the straight-chain or branched C-Co 0.190 rice (Oryza spp. such as Oryza sativa and alkylthioesters is the ethylthioester. Preferred derivatives are Oryza glaberrima); and the esters. 0191 sugar cane; 0182. The compositions of the present invention are suit 0.192 Legumes (Fabaceae), including e.g. able for controlling a large number of harmful plants, includ (Glycine max.), peanuts (Arachis hypogaea and pulse ing monocotyledonous weeds, in particular annual weeds crops such as peas including Pisum sativum, pigeon pea Such as gramineous weeds (grasses) including Echinochloa and cowpea, beans including broad beans (Vicia faba), species Such as barnyardgrass (Echinochloa crusgalli var. Vigna spp., and Phaseolus spp. and lentils (lens culinaris crus-galli), Digitaria species such as crabgrass (Digitaria var.); sanguinalis), Setaria species such as green foxtail (Setaria 0193 brassicaceae, including e.g. canola (Brassica viridis) and giant foxtail (Setaria faberii), Sorghum species napus), oilseed rape (Brassica napus), cabbage (B. Such as johnsongrass (Sorghum halepense Pers.), Avena spe oleracea var.), mustard Such as B. juncea, B. campestris, cies such as wild oats (Avena fatua), Cenchrus species such as B. marinosa, B. nigra and B. tournefortif, and turnip Cenchrus echinatus, Bromus species, Lolium species, (Brassica rapa var.); Phalaris species, Eriochloa species, Panicum species, Bra 0194 other broadleaf crops including e.g. sunflower, chiaria species, annual bluegrass (Poa annua), blackgrass cotton, flax, linseed, Sugarbeet, potato and tomato; (Alopecurus myosuroides), Aegilops cylindrica, Agropyron (0195 TNV-crops (TNV: trees, nuts and vine) including repens, Apera spica-venti, Eleusine indica, Cynodon dacty e.g. grapes, citrus, pomefruit, e.g. apple and pear, coffee, lon and the like. pistachio and oilpalm, Stonefruit, e.g. peach, almond, 0183 The compositions of the present invention are also walnut, olive, cherry, plum and apricot; Suitable for controlling a large number of dicotyledonous 0.196 turf, pasture and rangeland; weeds, in particular broad leaf weeds including Polygonum 0.197 onion and garlic; species such as wild buckwheat (Polygonum convolvOlus), 0198 bulb ornamentals such as tulips and narcissus: Amaranthus species such as pigweed (Amaranthus retrof. 0199 conifers and deciduous trees such as pinus, fir, lexus), Chenopodium species Such as common lambsquarters oak, maple, dogwood, hawthorne, crabapple, and rham (Chenopodium album L.), Sida species Such as prickly sida nus (buckthorn); and (Sida spinosa L.), Ambrosia species such as common rag 0200 garden ornamentals such as petunia, marigold, weed (Ambrosia artemisiifolia), Acanthospermum species, roses and Snapdragon. Anthemis species, Atriplex species, Cirsium species, Convol 0201 The compositions of the present invention are in vulus species, Conyza species, Cassia species, Commelina particular Suitable for combating/controlling undesired veg species, Datura species, Euphorbia species, Geranium spe etation in wheat, barley, rye, triticale, durum, rice, corn, Sug cies, Galinsoga Species, morning glory (Ipomoea species), arcane, Sorghum, soybean, pulse crops such as pea, bean and Lamium species, Malva species, Matricaria species, Sysim lentils, peanut, Sunflower, Sugarbeet, potato, cotton, brassica brium species, Solanum species, Xanthium species, Veronica crops, such as oilseed rape, canola, mustard, cabbage and species, Viola species, common chickweed (Stellaria media), turnip, turf, grapes, pomefruit, Such as apple and pear, Stone velvetleaf (Abutilon theophrasti), Hempsesbania (Sesbania fruit, Such as peach, almond, walnut, olive, cherry, plum and exaltata Cory). Anoda Cristata, Bidens pilosa, Brassica apricot, citrus, coffee, pistachio, garden ornamentals, such as kaber; Capsella bursa-pastoris, Centaurea cyanus, Galeopsis roses, petunia, marigold, Snap dragon, bulb ornamentals such tetrahit, Galium aparine, Helianthus annuus, Desmodium as tulips and narcissus, onion, garlic, conifers and deciduous tortuosum, Kochia scoparia, Mercurialis annua, Myosotis trees such as pinus, fir, oak, maple, dogwood, hawthorne, arvensis, Papaver rhoeas, Raphanus raphanistrum, Salsola crabapple and rhamnus. kali, Sinapis arvensis, Sonchus arvensis, Thlaspi arvense, 0202 The compositions of the present invention are most Tagetes minuta, Richardia brasiliensis, and the like. Suitable for combating/controlling undesired vegetation in 0184 The compositions of the present invention are also wheat, barley, rye, triticale, durum, rice, corn, Sugarcane, Suitable for controlling a large number of annual and peren Sorghum, soybean, pulse crops such as pea, bean and lentils, nial sedge weeds including Cyperus species such as purple peanut, Sunflower, Sugarbeet, potato, cotton, brassica crops, nutsedge (Cyperus rotundus L.), yellow nutsedge (Cyperus Such as oilseed rape, canola, mustard, cabbage and turnip, esculentus L.), hime-kugu (Cyperus brevifolius H.), sedge turf grapes, stonefruit, such as peach, almond, walnut, olive, weed (Cyperus microiria Steud), rice flatsedge (Cyperus iris cherry, plum and apricot, citrus, pistachio, onion, garlic and L.), and the like. deciduous trees. 0185. The compositions according to the present inven 0203 The compositions of the invention are particularly tion are suitable for combating/controlling common harmful Suitable for application in wheat, barley, rye, rice, corn, Sug plants in useful plants (i.e. in crops). The compositions of the arcane, Sorghum, soybean, pulse crops, Sunflower, potato, present invention are generally Suitable for combating/con cotton, turf grapes, stonefruit, citrus and pistachio. trolling undesired vegetation in 0204 If not stated otherwise, the compositions of the 0186 Grain crops, including e.g. invention are Suitable for application in any variety of the 0187 cereals (small grain cereals) such as wheat aforementioned crop plants. (Triticum aestivum) and wheat like crops such as 0205 The compositions according to the invention can durum (T. durum), einkorn (T. monococcum), emmer also be used in crop plants which are resistant or tolerant to US 2011/OO15068 A1 Jan. 20, 2011 one or more herbicides owing to genetic engineering or 0212. In the case of a post-emergence treatment of the breeding, which are resistant or tolerant to one or more patho plants, the herbicidal mixtures or compositions according to gens Such as plant pathogenous fungi owing to genetic engi the invention are preferably applied by foliar application. neering or breeding, or which are resistant or tolerant to attack Application may be effected, for example, by usual spraying by insects owing to genetic engineering or breeding. Suitable techniques with water as the carrier, using amounts of spray are for example crop plants, preferably corn, wheat, Sun mixture of approx. 50 to 1000 I/ha. flower, Sugarcane, cotton, rice, canola, oilseed rape or Soy 0213. The required application rate of the composition of beans, which crops are resistant or tolerant to herbicidal PPO the pure active compounds, i.e. of pyroxasulfone, herbicide B inhibitors, such as, for example, butafenacil, saflufenacil, and optionally safener or herbicide D depends on the density aZafenidin, carfentraZone, SulfentraZone, oxadiazon, oxadi of the undesired vegetation, on the development stage of the argyl, cinidon, flumioxazin, flumiclorac, flumipropyn, acif plants, on the climatic conditions of the location where the luorfen, bifenox, chlomethoxyfen, chlornitrofen, fluoronitro composition is used and on the application method. In gen fen, fomesafen, halosafen, lactofen, nitrofen, nitrofluorfen, or eral, the application rate of the composition (total amount of oxyfluorfen, or crop plants which, owing to introduction of pyroxasulfone, herbicide B and optional further actives) is the gene for Bt toxin by genetic modification, are resistant to from 15 to 5000 g/ha, preferably from 20 to 2500 g/ha of attack by certain insects. active Substance. 0206. The compositions of the present invention can be 0214. The required application rates of pyroxasulfone are applied in conventional manner by using techniques a skilled generally in the range from 1 g/ha to 500 g/ha and preferably person is familiar with. Suitable techniques include spraying, in the range from 5 g/ha to 400 g/ha or from 10 g/ha to 300 atomizing, dusting, spreading or watering. The type of appli g/ha of active Substance. cation depends on the intended purpose in a well known 0215. The required application rates of the herbicide B manner, in any case, the techniques should ensure the finest (total amount of herbicide B) are generally in the range from possible distribution of the active ingredients according to the 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha invention. to 2500 g/ha or from 5 g/ha to 2000 g/ha of active substance. 0207. The compositions can be applied pre- or post-emer 0216. The required application rates of the safener, if gence, i.e. before, during and/or after emergence of the unde applied, are generally in the range from 1 g/ha to 5000 g/ha sirable plants. When the compositions are used in crops, they and preferably in the range from 2 g/ha to 5000 g/ha or from can be applied after seeding and before the emergence of the 5 g/ha to 5000 g/ha of active substance. Preferably no safener crop plants. The compositions invention can, however, also be or virtually no safener is applied and thus the application rates applied prior to seeding of the crop plants. are below 5 g/ha, in particular below 2 g/ha or below 1 g/ha. 0208. It is a particular benefit of the compositions accord 0217. According to a first embodiment of the invention, ing to the invention that they have a very good post-emer the component b) comprises at least one phenyluracil herbi gence herbicide activity, i.e. they show a good herbicidal cide or a pyrazole herbicide. More specifically the component activity against emerged undesirable plants. Thus, in a pre b) according to this embodiment comprises at least one com ferred embodiment of invention, the compositions are applied pound of the formula I as defined above or a salt thereof, or at post-emergence, i.e. during and/or after, the emergence of the least one compound of the formula I as defined above or a salt undesirable plants. It is particularly advantageous to apply the thereof. mixtures according to the invention post-emergent when the 0218. Preferred compounds of formula I are the com undesirable plant starts with leaf development up to flower pounds of the formula Ia and more preferably the compounds ing. Since the composition show good crop tolerance, even of the formula Ia which are selected from butafenacil and when the crop has already emerged, they can be applied after saflufenacil. seeding of the crop plants and in particular during or after the 0219 Likewise preferred compounds of the formula I, are emergence of the crop plants. The compositions can also be the compounds of the formula Ib, in particular the compounds applied in a situation, where no crop is present yet at the time of the formula Ib, wherein of application, e.g. prior to planting of the crop. 0220 R is fluorine, R is chlorine, R is methyland R' 0209. In any case herbicide A and the at least one herbicide is cyclopropylmethyl, Band the optional further actives (safener Cand/or herbicide 0221) R' is chlorine, R is chlorine, R is methyland R' D) can be applied simultaneously or in Succession. is cyclopropylmethyl, 0210. The compositions are applied to the plants mainly 0222 R is fluorine, R is chlorine, R is methyland R' by spraying, in particular foliar spraying. Application can be is methyl, carried out by customary spraying techniques using, for 0223 R is chlorine, R is chlorine, R is methyland R' example, water as carrier and spray liquor rates of from about is methyl, 10 to 2000 I/ha or 50 to 1000 I/ha (for example from 100 to 0224 R is fluorine, R is chlorine, R is methyland R' 500 I/ha). Application of the herbicidal compositions by the is ethyl, low-volume and the ultra-low-volume method is possible, as 0225 R is chlorine, R is chlorine, R is methyland R' is their application in the form of microgranules. is ethyl, 0211. If the active ingredients are less well tolerated by 0226 R is fluorine, R is chlorine, R is methyland R' certain crop plants, application techniques may be used in is trifluoromethyl or which the herbicidal compositions are sprayed, with the aid of 0227 R’ is chlorine, R is chlorine, R is methyland R' the spray apparatus, in Such a way that they come into as little is trifluoromethyl. contact, if any, with the leaves of the sensitive crop plants 0228. Likewise preferred compounds of the formula I, are while reaching the leaves of undesirable plants which grow the compounds of the formula Id, in particular the compounds underneath, or the bare soil (post-directed, lay-by). of the formula Id, wherein US 2011/OO15068 A1 Jan. 20, 2011 11

(0229 R is fluorine, R is chlorine, R is methylandR 0252. The rate of application of pyroxasulfone is usually is cyclopropylmethyl, from 1 g/ha to 500 g/ha and preferably in the range from 5 0230 R is chlorine, R is chlorine, R is methylandR g/ha to 400 g/ha or from 10 g/ha to 300 g/ha of active sub is cyclopropylmethyl, stance (a.s.). 0231 R is fluorine, R is chlorine, R is methylandR 0253) The rate of application of the herbicides of formula is methyl, I or I", respectively, is usually 0.1 to 500 g/ha, as a rule 1 to 400 0232 R is chlorine, R is chlorine, R is methylandR g/ha, preferably 5 to 300 g/ha, of active substance (a.s.). is methyl, 0254 The compositions of this embodiment are particu 0233 R’ is fluorine, R is chlorine, R is methylandR larly suitable for controlling mono- and dicotyledonous is ethyl, weeds and sedge weeds, in particular Alopecurus myosuroi 0234 R is chlorine, R is chlorine, R is methylandR des, Apera spica-venti, Avena fatua, Brachiaria spec. Bro is ethyl, mus spec. Digitaria spec. Echinochloa spec., Eleusine 0235 R is fluorine, R is chlorine, R is methylandR indica, Lolium spec., Phalaris spec., Poa annua, Setaria is trifluoromethyl or spec. Abuthillon theoprasti, Amaranthus spec. Ambrosia 0236 R is chlorine, R is chlorine, R is methylandR spec., Brassica kaber, Capsella bursa-pastoris, Cassia spec. is trifluoromethyl. Chenopodium spec. ConvolvOlus spec. Conyza spec. 0237 Preferred compounds of formula I are the com Euphorbia spec. Galium aparine, Geranium spec., Ipomoea pounds of the formula Ic and more preferably the compounds spec., Kochia scoparia, Malva spec. Matricaria spec., Mer of the formula Ic, wherein curialis annua, Polygonum spec. Raphanus raphanistrum, 0238 R is fluorine, R is chlorine, R is methyl, R is Sida spec. Sinapis arvensis, Solanum spec. Sysimbrium difluoromethoxy, R is chlorine and R is ethyl, spec., Thlaspi arvense, Xanthium spec. and Commelina spec. 0239 R is chlorine, R is chlorine, R is methyl, R is 0255. The compositions of this embodimentare in particu difluoromethoxy, R is chlorine and R is ethyl, lar Suitable for combating undesired vegetation in wheat, 0240 R is fluorine, R is chlorine, R is methyl, R is barley, rye, triticale, durum, rice, corn, Sugarcane, Sorghum, difluoromethoxy, R is bromine and R is ethyl, or Soybean, pulse crops such as pea, bean and lentils, peanut, 0241 R is chlorine, R is chlorine, R is methyl, R is Sunflower, Sugarbeet, potato, cotton, brassica crops, such as difluoromethoxy, R is bromine and R is ethyl. oilseed rape, canola, mustard, cabbage and turnip, turf. 0242 Preferred compounds of formula I are also the com grapes, pomefruit Such as apple and pear, Stonefruit, such as pounds of the formula Ie and more preferably the compounds peach, almond, walnut, olive, cherry, plum and apricot, citrus of the formula Ie which are selected from fluazolate and and pistachio. pyraflufen-ethyl. 0256 The compositions of this embodiment are most suit 0243 In particular preferred compositions of this embodi able for application in wheat, barley, rye, rice, corn, Sugar ment, the herbicide B comprises or in particular is cane, Sorghum, pulse crops, Sunflower, turf grapes, stone butafenacil. fruit, citrus and pistachio. 0244. In other particular preferred compositions of this 0257 The compositions of this embodiment can prefer embodiment, the herbicide B comprises or in particular is ably be used in crops which tolerate and/or are resistant to the saflufenacil. action of PPO herbicides, preferably in crops which tolerate 0245. In other particular preferred compositions of this and/or are resistant to the action of formula I herbicides. The embodiment, the herbicide B comprises or in particular is a resistance and or tolerance to said herbicides may beachieved compound of the formula Ib, wherein R is fluorine, R is by conventional breeding and/or by genetic engineering chlorine, R is methyl and R is cyclopropylmethyl. methods. 0246. In other particular preferred compositions of this 0258 If not stated otherwise, the compositions of this embodiment, the herbicide B comprises or in particular is a embodiment are suitable for application in any variety of the compound of the formula Id, wherein R is fluorine, R is aforementioned crop plants. chlorine, R is methyl and R is trifluoromethyl. 0259. According to a second embodiment of the invention, 0247. In other particular preferred compositions of this the component b) comprises at least one triazolone or Oxa embodiment, the herbicide B comprises or in particular is a diazolone herbicide. More specifically the component b) compound of the formula Ic, wherein R is chlorine, R is according to this embodiment comprises at least one com chlorine, R is methyl, R is difluoromethoxy, R is bromine pound of the formula II as defined above. and R is ethyl. 0260 Preferred compounds of formula II include azafeni 0248. In other particular preferred compositions of this din, carfentraZone, SulfentraZone, oxadiazon and oxadiargyl. embodiment, the herbicide B comprises or in particular is a Also included are the salts of carfentraZone, in particular its compound of the formula Ic, wherein R is fluorine, R is Sodium salt, potassium salt, ammonium salt or Substituted chlorine, R is methyl, R is difluoromethoxy, R is chlorine ammonium salts as defined above, in particular mono-, diand and R'' is ethyl. tri-C-C-alkylammonium salts such as isopropylammonium 0249. In particular preferred compositions of this embodi salts and the esters of carfentraZone, in particular its C-Cs ment, the herbicide B comprises or in particular is fluazolate. alkyl esters, such as methylesters, ethylesters, isopropyl 0250 In other particular preferred compositions of this esters. A Suitable example of Such an ester is carfentraZone embodiment, the herbicide B comprises or in particular is ethyl. pyraflufen-ethyl. 0261. In particular preferred compositions of this embodi 0251. In this embodiment the relative weight ratio of ment, the herbicide B comprises or in particularis azafenidin. pyroxasulfone and an herbicide of formula I or I", respec 0262. In other particular preferred compositions of this tively, is preferably from 1:100 to 100:1 and more preferably embodiment, the herbicide B comprises or in particular is from 50:1 to 1:50. carfentraZone or a salt or ester thereof. US 2011/OO15068 A1 Jan. 20, 2011

0263. In further particular preferred compositions of this stituted ammonium salts as defined above, in particular embodiment, the herbicide B comprises or in particular is mono-, diand tri-C-C-alkylammonium salts such as isopro SulfentraZone. pylammonium salts, and the esters of cinidon and flumiclo 0264. In further particular preferred compositions of this rac, in particular their C-C-alkyl esters, such as methylest embodiment, the herbicide B comprises or in particular is ers, ethylesters, isopropyl esters. Suitable examples of Such oxadiazon. esters are cinidon-ethyl and flumiclorac-pentyl. 0265. In further particular preferred compositions of this 0276. In preferred compositions of this embodiment, the embodiment, the herbicide B comprises or in particular is herbicide B comprises or in particular is cinidon, flumioX oxadiargyl. azin, flumiclorac, or flumipropyn, or a salt or an ester of 0266. In this embodiment the relative weight ratio of cinidon or flumiclorac. pyroxasulfone and an herbicide of formula II is preferably 0277. In a particular preferred composition of this from 100:1 to 1:100, in particular from 50:1 to 1:50. embodiment, the herbicide B comprises or in particular is 0267. The rate of application of pyroxasulfone is usually flumioxazin. from 1 g/ha to 500 g/ha and preferably in the range from 5 0278. In another particular preferred composition of this g/ha to 400 g/ha or from 10 g/ha to 300 g/ha of active sub embodiment, the herbicide B comprises or in particular is stance (a.s.). flumiclorac. 0268. The rate of application of the formula II herbicide is 0279. In a further particular preferred composition of this usually 0.1 to 5000 g/ha, as a rule 1 to 2500 g/ha, preferably embodiment, the herbicide B comprises or in particular is 5 to 2000 g/ha, of active substance (a.s.). flumipropyn. 0269. The compositions of this embodiment are particu 0280. In this embodiment the relative weight ratio of larly Suitable for controlling mono- and dicotyledonous pyroxasulfone and an herbicide of the group b.3 is preferably weeds and sedge weeds, in particular Alopecurus myosuroi from 100:1 to 1:100, in particular from 50:1 to 1:50. des, Apera spica-venti, Avena fatua, Brachiaria spec. Bro 0281. The rate of application of pyroxasulfone is usually mus spec., Cenchrus spec. Digitaria spec. Echinochloa from 1 g/ha to 500 g/ha and preferably in the range from 5 spec., Eleusine indica, Lolium spec., Panicum spec., Phalaris g/ha to 400 g/ha or from 10 g/ha to 300 g/ha of active sub spec., Poa annua, red rice, Setaria spec. Amaranthus spec. stance (a.s.). Cassia spec., Chenopodium spec. ConvolvOlus spec. 0282. The rate of application of the formula III herbicide is Euphorbia spec. Galium aparine, Ipomoea spec. Kochia usually 0.1 to 1000 g/ha, as a rule 1 to 750 g/ha, preferably 5 Scoparia, Malva spec., Polygonum spec. Raphanus to 500 g/ha, of active substance (a.s.). raphanistrum, Sida spec. Solanum spec. Sonchus arvensis, 0283. The compositions of this embodiment are particu Veronica spec. Viola spec. Commelina spec. and Cyperus larly suitable for controlling mono- and dicotyledonous Spec. weeds and sedge weeds, in particular Alopecurus myosuroi 0270. The compositions of this embodimentare in particu des, Apera spica-venti, Avena fatua, Brachiaria spec. Bro lar Suitable for combating undesired vegetation in wheat, mus spec. Digitaria spec. Echinochloa spec., Eleusine barley, rye, triticale, durum, rice, corn, Sugarcane, Sorghum, indica, Lolium spec., Phalaris spec., Poa annus, Setaria Soybean, pulse crops such as pea, bean and lentils, peanut, spec. Amaranthus spec., Cassia spec., Chenopodium spec. Sunflower, Sugarbeet, potato, cotton, brassica crops, such as Conyza spec., Euphorbia spec. Galium aparine, Geranium oilseed rape, canola, mustard, cabbage and turnip, turf. spec., Ipomoea spec. Lamium spec. Malva spec. Matricaria grapes, stonefruit, such as peach, almond, walnut, olive, spec., Papaver thoeas, Sida spec. Solanum spec. Stellaria cherry, plum and apricot, citrus, pistachio, onion, garlic and media, Veronica spec. Viola spec. and Commelina spec. deciduous trees. 0284. The compositions of this embodimentare in particu 0271 The compositions of this embodiment are most suit lar Suitable for combating undesired vegetation in wheat, able for application in wheat, barley, rye, durum, rice, Sugar barley, rye, triticale, durum, rice, corn, Sugarcane, Sorghum, cane, soybeans, cotton, Sunflower, potato, grapes, stonefruit, Soybean, pulse crops such as pea, bean and lentils, peanut, citrus and pistachio. Sunflower, Sugarbeet, potato, cotton, brassica crops, such as 0272. If not stated otherwise, the compositions of this oilseed rape, canola, mustard, cabbage and turnip, turf. embodiment are suitable for application in any variety of the grapes, stonefruit, such as peach, almond, walnut, olive, aforementioned crop plants. cherry, plum and apricot, citrus and pistachio. 0273. The compositions of this embodiment can prefer 0285. The compositions of this embodiment are most suit ably be used in crops which tolerate and/or are resistant to the able for application in wheat, barley, rye, triticale, durum, action of PPO herbicides, preferably in crops which tolerate rice, Sugarcane, soybeans, peanuts, potato, turfgrapes, Stone and/or are resistant to the action of formula II herbicides. The fruit, citrus and pistachio. resistance and or tolerance to said herbicides may beachieved 0286. If not stated otherwise, the compositions of this by conventional breeding and/or by genetic engineering embodiment are suitable for application in any variety of the methods. aforementioned crop plants. 0274. According to a third embodiment of the invention, 0287. The compositions of this embodiment can prefer the component b) comprises at least one dicarboximide her ably be used in crops which tolerate and/or are resistant to the bicide. More specifically the component b) according to this action of PPO herbicides, preferably in crops which tolerate embodiment comprises at least one compound of the formula and/or are resistant to the action of formula III herbicides. The III as defined above. resistance and or tolerance to said herbicides may beachieved 0275 Preferred compounds of formula III include cini by conventional breeding and/or by genetic engineering don, flumioxazin, flumiclorac, and flumipropyn. Also methods. included are the salts ofcinidon and flumiclorac, in particular 0288 According to a fourth embodiment of the invention, their sodium salts, potassium salts, ammonium salts or Sub the component b) comprises at least one nitrophenylether US 2011/OO15068 A1 Jan. 20, 2011

herbicide. More specifically the component b) according to action of PPO herbicides, preferably in crops which tolerate this embodiment comprises at least one compound of the and/or are resistant to the action of formula IV herbicides. The formula IV as defined above. resistance and or tolerance to said herbicides may beachieved 0289 Preferred compounds of formula IV include nitro by conventional breeding and/or by genetic engineering fen, bifenox, oxyfluorfen, acifluorfen, fluoroglycofen, fome methods. safen, lactofen, halosafen, chlornitrofen, fluornitrofen, chlo 0300. According to a fifth embodiment of the invention, methoxyfen and nitrofluorfen. Also included are the salts of the component b) comprises at least one triazindione herbi acifluorfen and fluoroglycofen, in particular the Sodium salts, cide. More specifically the component b) according to this potassium salts, ammonium salts or Substituted ammonium embodiment comprises at least one compound of the formula salts as defined above, in particular mono-, di and tri-C-C- V as defined above. alkylammonium salts such as isopropylammonium salts and 0301 In a preferred compound of formula V the variable Y the esters of acifluorfen and fluoroglycofen, in particular their is S, Rf is fluorine, R is propargyl, R is methyl and R is C-Cs-alkyl esters, such as methylesters, ethylesters, isopro methyl. pyl esters. A Suitable example of Such a salt is acifluorfen 0302) In this embodiment the relative weight ratio of sodium. Suitable examples of such esters are acifluorfen pyroxasulfone and an herbicide of formula V is preferably methyl and fluoroglycofen-ethyl. from 100:1 to 1:100, in particular from 50:1 to 1:50. 0290. In preferred compositions of this embodiment, the 0303. The rate of application of pyroxasulfone is usually herbicide B comprises or in particular is include nitrofen, from 1 g/ha to 500 g/ha and preferably in the range from 5 bifenox, oxyfluorfen, acifluorfen, fluoroglycofen, fomesafen, g/ha to 400 g/ha or from 10 g/ha to 300 g/ha of active sub lactofen, halosafen, chlornitrofen, fluornitrofen, chlom stance (a.s.). ethoxyfen and nitrofluorfen, acifluorfen-sodium, or a salt or 0304. The rate of application of the formula V herbicide is an ester of acifluorfen or fluoroglycofen. usually 0.1 to 5000 g/ha, as a rule 1 to 2500 g/ha, preferably 0291. In a particular preferred composition of this 5 to 2000 g/ha, of active substance (a.s.). embodiment, the herbicide B comprises or in particular is 0305 The compositions of this embodiment are particu oxyfluorfen. larly suitable for controlling mono- and dicotyledonous 0292. In this embodiment the relative weight ratio of weeds and sedge weeds, in particular Alopecurus myosuroi pyroxasulfone and an herbicide of formula IV is preferably des, Apera spica-venti, Avena fatua, Brachiaria spec. Bro from 100:1 to 1:300, in particular from 50:1 to 1:200. mus spec., Cenchrus spec. Digitaria spec. Echinochloa 0293. The rate of application of pyroxasulfone is usually Spec., Eleusine indica, Lolium spec., Panicum spec., Phalaris from 1 g/ha to 500 g/ha and preferably in the range from 5 spec., Poa annua, red rice, Setaria spec. Amaranthus spec. g/ha to 400 g/ha or from 10 g/ha to 300 g/ha of active sub Cassia spec., Chenopodium spec. ConvolvOlus spec. stance (a.s.). Euphorbia spec. Galium aparine, Ipomoea spec. Kochia 0294 The rate of application of the formula IV herbicide scoparia, Malva spec. Polygonum spec. Raphanus is usually 1 to 5000 g/ha, as a rule 5 to 4000 g/ha, preferably raphanistrum, Sida spec. Solanum spec. Sonchus arvensis, 10 to 2000 g/ha, of active substance (a.s.). Veronica spec. Viola spec. Commelina spec. and Cyperus 0295 The compositions of this embodiment are particu Spec. larly Suitable for controlling mono- and dicotyledonous 0306 The compositions of this embodimentare in particu weeds and sedge weeds, in particular Alopecurus myosuroi lar Suitable for combating undesired vegetation in wheat, des, Apera spica-venti, Avena fatua, Brachiaria spec. Bro barley, rye, triticale, durum, rice, corn, Sugarcane, Sorghum, mus spec. Digitaria spec. Echinochloa spec., Eleusine Soybean, pulse crops such as pea, bean and lentils, peanut, indica, Lolium spec., Phalaris spec., Poa annus, Setaria Sunflower, Sugarbeet, potato, cotton, brassica crops, such as spec. Abuthillon theoprasti, Amaranthus spec., Atriplex spec. oilseed rape, canola, mustard, cabbage and turnip, turf. Chenopodium spec. Datura spec., Euphorbia spec. Galium grapes, stonefruit, such as peach, almond, walnut, olive, aparine, Ipomoea spec. Lamium spec., Polygonum spec. cherry, plum and apricot, citrus, pistachio, onion, garlic and Veronica spec. Viola spec. Xanthium spec. and Commelina deciduous trees. Spec. 0307 The compositions of this embodiment are most suit 0296. The compositions of this embodimentare in particu able for application in wheat, barley, rye, durum, rice, Sugar lar Suitable for combating undesired vegetation in wheat, cane, soybeans, cotton, Sunflower, potato, grapes, Stonefruit, barley, rye, triticale, durum, rice, corn, Sugarcane, Sorghum, citrus and pistachio. Soybean, pulse crops such as pea, bean and lentils, peanut, 0308 If not stated otherwise, the compositions of this Sunflower, Sugarbeet, potato, cotton, brassica crops, such as embodiment are suitable for application in any variety of the oilseed rape, canola, mustard, cabbage and turnip, turf. aforementioned crop plants. grapes, stonefruit, such as peach, almond, walnut, olive, 0309 The compositions of this embodiment can prefer cherry, plum and apricot, citrus, pistachio, onion, garlic and ably be used in crops which tolerate and/or are resistant to the deciduous trees. action of PPO herbicides, preferably in crops which tolerate 0297. The compositions of this embodiment are most suit and/or are resistant to the action of formula V herbicides. The able for application in wheat, barley, rice, Sugarcane, Soy resistance and or tolerance to said herbicides may beachieved bean, pulse crops, peanuts, brassica crops, grapes, stonefruit, by conventional breeding and/or by genetic engineering citrus and pistachio. methods. 0298 If not stated otherwise, the compositions of this 0310. According to a sixth embodiment of the invention, embodiment are suitable for application in any variety of the the component b) comprises at least one dicarboxamide her aforementioned crop plants. bicide. More specifically the component b) according to this 0299 The compositions of this embodiment can prefer embodiment comprises at least one compound of the formula ably be used in crops which tolerate and/or are resistant to the VI as defined above. US 2011/OO15068 A1 Jan. 20, 2011

0311 A particular preferred compound of the formula VI both formulations contain at least one carrier material, if is the compound of the formula VIa. desired, one or more Surfactants and, if desired, one or more 0312. In this embodiment the relative weight ratio of further auxiliaries customary for crop protection composi pyroxasulfone and an herbicide of formula V1 is preferably tions. In the case of two package formulations the formulation from 100:1 to 1:100, in particular from 50:1 to 1:50. containing pyroxasulfone and the formulation containing the 0313 The rate of application of pyroxasulfone is usually herbicide B are mixed prior to application. Preferably the from 1 g/ha to 500 g/ha and preferably in the range from 5 mixing is performed as a tank mix, i.e. the formulations are g/ha to 400 g/ha or from 10 g/ha to 300 g/ha of active sub mixed immediately prior or upon dilution with water. If the stance (a.s.). compositions of the invention comprise one or more further 0314. The rate of application of the formula VI herbicide is actives such as a safener and/or a herbicide D, the composi usually 0.1 to 5000 g/ha, as a rule 1 to 2500 g/ha, preferably tions may also be in the form of three or four package formu 5 to 2000 g/ha, of active substance (a.s.). lations. 0315. The compositions of this embodiment are particu 0322. In the formulation of the present invention the active larly Suitable for controlling mono- and dicotyledonous ingredients, i.e. pyroxasulfone, herbicide B and optional fur weeds and sedge weeds, in particular Alopecurus myosuroi ther actives are present in Suspended, emulsified or dissolved des, Apera spica-venti, Avena fatua, Brachiaria spec. Bro form. The formulation according to the invention can be in the mus spec., Cenchrus spec. Digitaria spec. Echinochloa form of aqueous solutions, powders, Suspensions, also spec., Eleusine indica, Lolium spec., Panicum spec., Phalaris highly-concentrated aqueous, oily or other Suspensions or spec., Poa annua, red rice, Setaria spec. Amaranthus spec. dispersions, aqueous emulsions, aqueous microemulsions, Cassia spec., Chenopodium spec. ConvolvOlus spec. aqueous Suspo-emulsions, oil dispersions, pastes, dusts, Euphorbia spec. Galium aparine, Ipomoea spec. Kochia materials for spreading or granules. scoparia, Malva spec. Polygonum spec. Raphanus 0323 Depending on the formulation type, they comprise raphanistrum, Sida spec. Solanum spec. Sonchus arvensis, one or more liquid or Solid carriers, if appropriate Surfactants Veronica spec. Viola spec. Commelina spec. and Cyperus (such as dispersants, protective colloids, emulsifiers, wetting Spec. agents and tackifiers), and if appropriate further auxiliaries 0316 The compositions of this embodimentare in particu which are customary for formulating crop protection prod lar Suitable for combating undesired vegetation in wheat, ucts. The person skilled in the art is sufficiently familiar with barley, rye, triticale, durum, rice, corn, Sugarcane, Sorghum, the recipes for such formulations. Further auxiliaries include Soybean, pulse crops such as pea, bean and lentils, peanut, e.g. organic and inorganic thickeners, bactericides, antifreeze Sunflower, Sugarbeet, potato, cotton, brassica crops, such as agents, antifoams, colorants and, for seed formulations, adhe oilseed rape, canola, mustard, cabbage and turnip, turf. SVS. grapes, stonefruit, such as peach, almond, walnut, olive, 0324 Suitable carriers include liquid and solid carriers. cherry, plum and apricot, citrus, pistachio, onion, garlic and Liquid carriers include e.g. non-aqueous solvents such as deciduous trees. cyclic and aromatic hydrocarbons, e.g. paraffins, tetrahy 0317. The compositions of this embodiment are most suit dronaphthalene, alkylated naphthalenes and their derivatives, able for application in wheat, barley, rye, durum, rice, Sugar alkylated benzenes and their derivatives, alcohols such as cane, soybeans, cotton, Sunflower, potato, grapes, stonefruit, methanol, ethanol, propanol, butanol and cyclohexanol, citrus and pistachio. ketones such as cyclohexanone, strongly polar solvents, e.g. 0318) If not stated otherwise, the compositions of this amines Such as N-methylpyrrolidone, and water as well as embodiment are suitable for application in any variety of the mixtures thereof. Solid carriers include e.g. mineral earths aforementioned crop plants. Such as silicas, silica gels, silicates, talc, kaolin, limestone, 0319. The compositions of this embodiment can prefer lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, ably be used in crops which tolerate and/or are resistant to the calcium sulfate, magnesium Sulfate, magnesium oxide, action of PPO herbicides, preferably in crops which tolerate ground synthetic materials, fertilizers such as ammonium and/or are resistant to the action of formula V herbicides. The Sulfate, ammonium phosphate, ammonium nitrate, , and resistance and or tolerance to said herbicides may beachieved products of vegetable origin Such as cereal meal, tree bark by conventional breeding and/or by genetic engineering meal, wood meal and nutshell meal, cellulose powders, or methods. other solid carriers. 0320. The present invention also relates to formulations of 0325 Suitable surfactants (adjuvants, wetting agents, the compositions according to the present invention. The tackifiers, dispersants and also emulsifiers) are the alkali formulations contain, besides the composition, at least one metal salts, alkaline earth metal salts and ammonium salts of organic or inorganic carrier material. The formulations may aromatic Sulfonic acids, for example lignoSulfonic acids (e.g. also contain, if desired, one or more surfactants and, if Borrespers-types, Borregaard), phenolsulfonic acids, naph desired, one or more further auxiliaries customary for crop thalenesulfonic acids (Morwet types, Akzo Nobel) and dibu protection compositions. tylnaphthalenesulfonic acid (Nekal types, BASF SE), and of 0321. The formulation may be in the form of a single fatty acids, alkyl- and alkylarylsulfonates, alkylsulfates, lau package formulation containing both the herbicide A and the ryl ether sulfates and fatty alcohol sulfates, and salts of sul at least one herbicide B together with liquid and/or solid fated hexa-hepta- and octadecanols, and also offatty alcohol carrier materials, and, if desired, one or more surfactants and, glycol ethers, condensates of Sulfonated naphthalene and its if desired, one or more further auxiliaries customary for crop derivatives with formaldehyde, condensates of naphthalene protection compositions. The formulation may be in the form or of the naphthalenesulfonic acids with phenol and formal of a two package formulation, wherein one package contains dehyde, polyoxyethylene octylphenol ether, ethoxylated a formulation of pyroxasulfone while the other package con isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphe tains a formulation of the at leastoneherbicide B and wherein nyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl US 2011/OO15068 A1 Jan. 20, 2011 alcohol, fatty alcohol/ethylene oxide condensates, ethoxy formulations comprise from 1 to 98% by weight, preferably lated castor oil, polyoxyethylene alkyl ethers or polyoxypro 10 to 60% by weight, of active ingredients (sum of pyroxas pylene alkyl ethers, lauryl alcohol polyglycol ether acetate, ulfone, herbicide Band optionally further actives). The active Sorbitol esters, lignoSulfite waste liquors and proteins, dena ingredients are employed in a purity of from 90% to 100%, turated proteins, polysaccharides (e.g. methylcellulose), preferably 95% to 100% (according to NMR spectrum). hydrophobically modified starches, polyvinyl alcohol 0336. The active compounds A and B and optionally fur (Mowiol types Clariant), polycarboxylates (BASF SE. ther actives as well as the compositions according to the Sokalan types), polyalkoxylates, polyvinylamine (BASF SE. invention can, for example, be formulated as follows: Lupamine types), polyethyleneimine (BASF SE. Lupasol 1. Products for dilution with water types), polyvinylpyrrolidone and copolymers thereof. A Water-soluble concentrates 0326 Examples of thickeners (i.e. compounds which 0337 10 parts by weight of active compound (or compo impart to the formulation modified flow properties, i.e. high sition) are dissolved in 90 parts by weight of water or a Viscosity in the State of rest and low viscosity in motion) are water-soluble solvent. As an alternative, wetters or other adju polysaccharides, such as Xanthan gum (Kelzan(R) from vants are added. The active compound dissolves upon dilu Kelco), RhodopolR 23 (Rhone Poulenc) or Veegum(R) (from tion with water. This gives a formulation with an active com R.T. Vanderbilt), and also organic and inorganic sheet miner pound content of 10% by weight. als, such as Attaclay R (from Engelhardt). B Dispersible concentrates 0327 Examples of antifoams are silicone emulsions (such 0338 20 parts by weight of active compound (or compo as, for example, Silikon RSRE, Wacker or Rhodorsil R) from sition) are dissolved in 70 parts by weight of cyclohexanone Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, with addition of 10 parts by weight of a dispersant, for organofluorine compounds and mixtures thereof. example polyvinylpyrrolidone. Dilution with water gives a 0328 Bactericides can be added for stabilizing the aque dispersion. The active compound content is 20% by weight. ous herbicidal formulations. Examples of bactericides are C Emulsifiable concentrates bactericides based on dichlorophen and benzyl alcohol hemi 0339 15 parts by weight of active compound (or compo formal (Proxel R. from ICI or Acticide(R) RS from Thor Che sition) are dissolved in 75 parts by weight of an organic mie and Kathon(R) MK from Rohm & Haas), and also isothia Solvent (e.g. alkylaromatics) with addition of calcium dode Zolinone derivates, such as alkylisothiazolinones and cylbenzenesulfonate and castor oil ethoxylate (in each case 5 benzisothiazolinones (Acticide MBS from Thor Chemie). parts by weight). Dilution with water gives an emulsion. The 0329. Examples of antifreeze agents are ethylene glycol, formulation has an active compound content of 15% by propylene glycol, or glycerol. weight. 0330. Examples of colorants are both sparingly water soluble pigments and water-soluble dyes. Examples which D Emulsions may be mentioned are the dyes known under the names 0340 25 parts by weight of active compound (or compo Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1. sition) are dissolved in 35 parts by weight of an organic and also pigment blue 15:4, pigment blue 15:3, pigment blue Solvent (e.g. alkylaromatics) with addition of calcium dode 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, cylbenzenesulfonate and castor oil ethoxylate (in each case 5 pigment yellow 13, pigment red 112, pigment red 48:2, pig parts by weight). This mixture is introduced into 30 parts by ment red 48:1, pigment red 57:1, pigment red 53:1, pigment weight of water by means of an emulsifier (Ultraturrax) and orange 43, pigment orange 34, pigment orange 5, pigment made into a homogeneous emulsion. Dilution with water green 36, pigment green 7, pigment white 6, pigment brown gives an emulsion. The formulation has an active compound 25, basic violet 10, basic violet 49, acid red 51, acid red 52, content of 25% by weight. acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108. E Suspensions 0331 Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose. 0341. In an agitated ball mill, 20 parts by weight of active 0332 To prepare emulsions, pastes or oil dispersions, the compound (or composition) are comminuted with addition of active the components, as such or dissolved in an oil or 10 parts by weight of dispersants and wetters and 70 parts by Solvent, can be homogenized in water by means of wetting weight of water or an organic solvent to give a fine active agent, tackifier, dispersant or emulsifier. Alternatively, it is compound Suspension. Dilution with water gives a stable possible to prepare concentrates consisting of active Sub Suspension of the active compound. The active compound stance, wetting agent, tackifier, dispersant or emulsifier and, content in the formulation is 20% by weight. if desired, solvent or oil, and these concentrates are suitable F Water-dispersible granules and water-soluble granules for dilution with water. 0342 50 parts by weight of active compound (or compo 0333 Powders, materials for spreading and dusts can be sition) are ground finely with addition of 50 parts by weight of prepared by mixing or concomitant grinding of the active the dispersants and wetters and made into water-dispersible or components a) and b) and optionally safener c) and/or herbi water-soluble granules by means oftechnical appliances (for cide D with a solid carrier. example extrusion, spray tower, fluidized bed). Dilution with 0334 Granules, e.g. coated granules, impregnated gran water gives a stable dispersion or solution of the active com ules and homogeneous granules, can be prepared by binding pound. The formulation has an active compound content of the active ingredients to Solid carriers. 50% by weight. 0335 The formulations of the invention comprise a herbi cidally effective amount of the composition of the present G Water-Dispersible Powders and Water-Soluble Powders invention. The concentrations of the active ingredients in the 0343 75 parts by weight of active compound (or compo formulations can be varied within wide ranges. In general, the sition) are ground in a rotor-stator mill with addition of 25 US 2011/OO15068 A1 Jan. 20, 2011 parts by weight of dispersants, wetters and silica gel. Dilution positions were suspended or emulsified in water as distribu with water gives a stable dispersion or solution of the active tion medium and sprayed using finely distributing nozzles. compound. The active compound content of the formulation 0353. The respective herbicides A and/or safener were is 75% by weight. formulated as 10% by weight strength suspension concen trate and introduced to the spray liquor with the amount of H Gel Formulations Solvent system used for applying the active compound. Her 0344 Inaball mill, 20 parts by weight of active compound bicide B and/or safener were used as commercially available (or composition), 10 parts by weight of dispersant, 1 part by formulations and introduced to the spray liquor with the weight of gelling agent and 70 parts by weight of water or of amount of solvent system used for applying the active com an organic solvent are mixed to give a fine Suspension. Dilu pound. In the examples, the solvent used was water. tion with water gives a stable Suspension with active com 0354 Pyroxasulfone was used either as an aqueous sus pound content of 20% by weight. pension concentrate having an active ingredient concentra tion of 100 g/l or as an emulsifiable concentrate having an 2. Products to be applied undiluted active ingredient concentration of 50 g/l. I Dusts 0355 Saflufenacil was used as a wettable granule formu lation having an active ingredient content of 70% by weight. 0345) 5 parts by weight of active compound (or composi 10356. The compound of the formula Ic, where R is chlo tion) are ground finely and mixed intimately with 95 parts by rine, R is chlorine, R'' is ethyl, R is difluoromethoxy and R' weight of finely divided kaolin. This gives a dusting powder is bromine, was used as an emulsifiable concentrate having an with an active compound content of 5% by weight. active ingredient concentration of 50 g/l. This compound is also termed as compound Ic-1. JGranules (GR, FG, GG, MG) 0357 The compound of the formula V, where R is fluo 0346 0.5 parts by weight of active compound (or compo rine, R is propargyl, R is methyl, R is methyl and Y is S, sition) are ground finely and associated with 99.5 parts by was used as an emulsifiable concentrate having an active weight of carriers. Current methods here are extrusion, spray ingredient concentration of 50 g/l. This compound is also drying or the fluidized bed. This gives granules to be applied termed as compound V-1. undiluted with an active compound content of 0.5% by 0358. The test period extended over 21 days. During this weight. time, the plants were tended, and their response to the treat KULV solutions (UL) ments with active compound was evaluated. 0347 10 parts by weight of active compound (or compo 0359 The evaluation for the damage caused by the chemi sition) are dissolved in 90 parts by weight of an organic cal compositions was carried out using a scale from 0 to Solvent, for example Xylene. This gives a product to be 100%, compared to the untreated control plants. Here, 0 applied undiluted with an active compound content of 10% by means no damage and 100 means complete destruction of the weight. plants. 0348 Aqueous use forms can be prepared from emulsion 0360. The plants used in the greenhouse experiments concentrates, Suspensions, pastes, wettable powders or water belonged to the following species: dispersible granules by adding water. 0349. It may furthermore be beneficial to apply the com positions of the invention alone or in combination with other herbicides, or else in the form of a mixture with other crop Scientific Name Code Common Name protection agents, for example together with agents for con Abution theophrasti ABUTH welvetleaf trolling pests or phytopathogenic fungi or bacteria. Also of Agropyron repens AGRRE quackgrass Alopectiris myosiiroides ALOMY blackgrass interest is the miscibility with mineral salt solutions, which Amaranthus retroflexus AMARE pig weed are employed for treating nutritional and trace element defi Ambrosia artemisifolia AMBEL common ragweed ciencies. Other additives such as non-phytotoxic oils and oil Apera spica-venti APESV windgrass Avena fattia AVEFA wild oat concentrates may also be added. Brachiaria plantaginea BRAPL alexandergrass Bronts inermis BROIN awnless brome USE EXAMPLES Bromus Sieriis BROST sterile brome Brassica naptis spp. naptis BRSNW winter oilseed-rape 0350. The effect of the herbicidal compositions according Capsella bursa-pastoris CAPBP sheperd's-purse to the invention of herbicides A and B and, if appropriate, Cenchrus echinaius CCHEC Sandbur safener on the growth of undesirable plants compared to the Chenopodium album CHEAL lambsquarter Commelina benghaiensis COMBE tropical spiderwort herbicidally active compounds alone was demonstrated by Digitaria Sangiinalis DIGSA large crabgrass the following greenhouse experiments: Echinochloa crus-galli ECHCG barnyardgrass 0351. For the pre-emergence treatment, directly after sow Eleusine indica ELE gOOSegraSS ing the active compounds, which had been Suspended or Galium aparine GALAP cleaver emulsified in water, were applied by means of finely distrib Glycine max GLXMA Soybean Gossypium hirsuttin GOSHI cottOn uted noZZles. The containers were irrigated gently to promote Helianthus annuit is HELAN Sunflower germination and growth and Subsequently covered with trans Hordeum vulgare HORVW winter barley parent plastic hoods until plant had rooted. This cover caused Kochia Scoparia KCHSC kochia uniform germination of the tests plants, unless this was Lamiin purpurelim LAMPU red deadnettle Lolium multiflorum LOLMU italian ryegrass adversely affected by active compounds. Matricaria inermis MATIN scentless mayweed 0352 For the post-emergence treatment, the test plants Mercuria is annua MERAN annual mercury were first grown to a height of 3 to 20 cm, depending on the Orysa Saiiva ORYSA rice plant habit, and only then treated. Here, the herbicidal com US 2011/OO15068 A1 Jan. 20, 2011 17

R. Colby (1967) “Calculating synergistic and antagonistic -continued responses of herbicide combinations'. Weeds 15, p. 22 ff.

Scientific Name Code Common Name where Panicum dichotomiflorum PANDI fall panicum Panicum miliaceum PANMI proso millet 0362 X-effect in percent using herbicide A at an appli Phaiaris canariensis PHACA canary graSS cation rate a: Ipomoea purpurea PHBPU tall morningglory 0363 Y-effect in percent using herbicide Batan appli Poa annia POAAN annual bluegrass cation rate b: Polygontin convolvulus POLCO wild buckwheat 03.64 E=expected effect (in 96) of A+B at application Secale cereale SECCW winter rye rates a+b. Setaria faberii SETFA giant foxtail 0365. If the value observed in this manner is higher than Setaria itaica SETIT foxtail millet the value E calculated according to Colby, a synergistic effect Setaria litescens SETLU yellow foxtail is present. Setaria viridis SETVI green foxtail Soianum nigrum SOLNI black nightshade 0366 An accelerated activity is observed when the dam Sorghum halepense SOREHA johnsongrass age 7 or 8 days after treatment (7 DAT or 8 DAT) achieved by Steiaria media STEME chickweed the combination shows a synergistic effect. Thlaspi arvense THLAR field pennycress 0367 Table la relates to the herbicidal activity of the Trictim aestivum TRZAS spring wheat individual actives in pre-emergence application assessed 8 Trictim aestivum TRZAW winter wheat DAT and 20 DAT. Table 1b relates the herbicidal activity of Veronica persica VERPE field speedwell the combined actives in pre-emergence application assessed 8 Vioia arvensis VIOAR field pansy DAT and 20 DAT. Xanthium strumarium XANST cocklebur 0368 Table 2a relates to the herbicidal activity of the Zea mays ZEAMX COil individual actives in post-emergence application assessed 8 DAT and 20 DAT. Table 2b relates the herbicidal activity of the combined actives in post-emergence application assessed 0361 Colby's formula was applied to determine whether 8 DAT and 20 DAT. the composition showed synergistic action. The value E, 0369 Tables 3 and 4 relate to the herbicidal activity of the which is to be expected if the activity of the individual com individual actives and of the combinations in post-emergence pounds is just additive, was calculated using the method of S. application assessed 20 DAT.

TABLE 1 a

Application in Pre-Emergence of pyroxasulfone and saflufenacil (individual activities)

pyroxasulfone (A) saflufenacil (B)

use rate observed % activity use rate gai?ha observed % activity

weed gai/ha) 8 DAT 20 DAT gai?ha 8 DAT 20 DAT)

SETFA 50 90 98 12.5 2O 35 SETFA 25 85 98 6.25 O 35 SETIT 25 75 98 25 40 55 ALOMY 50 90 98 12.5 30 30 BROIN 25 60 75 3.13 O O SOREHA 25 75 95 3.13 O O CHEAL 50 70 98 3.13 75 60 CHEAL 25 65 95 3.13 75 60 PHBPU 25 40 50 6.25 8O 8O PHBPU 50 65 90 3.13 45 50 AMBEL 50 50 8O 12.5 70 8O AMBEL 25 40 65 12.5 70 8O MATIN 50 2O 85 6.25 95 98 MATIN 25 O 60 6.25 95 98 GALAP 50 70 90 3.13 40 40 GALAP 25 50 8O 3.13 40 40 KCHSC 25 40 98 12.5 75 8O US 2011/OO15068 A1 Jan. 20, 2011 18

TABLE 1b. Application in Pre-Emergence of pyroxasulfone and saflufenacil (combined activities pyroxasulfone + saflufenacil Synergism uSe rate Observed 90 activity expected 90 activity YN YN weed gai?ha 8 DAT 20 DAT) 8 DAT2) 20 DAT2) 8 DAT 20 DAT)

SETFA 50 - 12.5 95 OO 92 99 Y Y SETFA 25 - 6.25 90 OO 85 99 Y Y SETIT 25 - 25 95 OO 85 99 Y Y ALOMY SO - 12.5 95 OO 93 99 Y Y BRON 2S - 3.12S 70 85 60 75 Y Y SOREHA 25 - 3.12S 85 OO 75 95 Y Y CHEAL SO - 3.12S 95 OO 93 99 Y Y CHEAL 25 - 3.12S 95 OO 91 98 Y Y PHBPU 25 - 6.25 90 OO 88 90 Y Y PHBPU SO - 3.12S 90 OO 81 95 Y Y AMBEL SO - 12.5 95 OO 85 96 Y Y AMBEL 25 - 12.5 90 98 82 93 Y Y MATIN 50 - 6.25 98 OO 96 1OO Y Y MATIN 25 - 6.25 98 OO 95 99 Y Y GALAP SO - 3.125 95 95 82 94 Y Y GALAP 25 - 3.125 90 90 70 88 Y Y KCHSC 25 - 12.5 95 OO 85 1OO Y Y

observed activity in % destruction 8 or 20 days after treatment 'calculated from the individual activities by Colby's formula Synergism: Y = Yes; N = No

TABLE 2a Application in Post-Emergence of pyroxasulfone and saflufenacil (individual activities pyroxasulfone (A saflufenacil (B use rate observed 90 activity use rate gai?ha observed 90 activity weed gai?ha) 8 DAT 20 DAT gai?ha 8 DAT 20 DAT) ECHCG 13 25 8O 13 15 O ECHCG 13 25 8O 6.25 10 O ECHCG 13 25 8O 1.6 10 O SETLU 13 O 65 1.6 30 10 ALOMY 100 40 75 13 35 15 ALOMY 100 40 75 6.25 2O O ALOMY 13 O 15 1.6 O O SOREHA 50 65 90 1.6 2O 35 SETIT 100 45 8O 6.25 30 2O SETIT 50 25 75 3.1 30 15 CHEAL 50 60 65 13 45 35 CHEAL 50 60 65 6.25 35 35 CHEAL 13 35 25 6.25 35 35 POLCO OO 50 55 13 95 98 POLCO OO 50 55 1.6 35 30 POLCO 50 50 50 1.6 35 30 POLCO 25 30 50 1.6 35 30 SOLNI OO 75 90 13 85 85 SOLNI 13 75 75 13 85 85 XANST OO 25 55 6.25 70 8O XANST 25 2O 25 6.25 70 8O XANST 13 O O 3.1 70 75 XANST OO 25 55 1.6 35 45 GALAP OO 70 90 13 8O 70 GALAP 25 60 85 6.25 35 30 GALAP OO 70 90 3.1 25 2O GALAP 25 60 85 3.1 25 2O GALAP OO 70 90 1.6 15 2O GALAP 25 60 85 1.6 15 2O KCHSC OO 60 70 6.25 60 30 KCHSC 13 60 50 6.25 60 30 US 2011/OO15068 A1 Jan. 20, 2011 19

TABLE 2b Application in Post-Emergence of pyroxasulfone and saflufenacil (combined activities pyroxasulfone + saflufenacil Synergism uSe rate Observed 90 activity expected 90 activity YN YN weed gai?ha 8 DAT 20.DAT) 8 DAT2) 20 DAT2) 8 DAT 20 DAT)

ECHCG 13 - 13 60 90 36 8O Y Y ECHCG 13 - 6.25 50 85 33 8O Y Y ECHCG 13 - 1.6 50 85 33 8O Y Y SETLU 13 + 1.6 70 70 30 69 Y Y ALOMY 100 - 13 65 8O 61 79 Y Y ALOMY 100 - 6.25 55 8O 52 75 Y Y ALOMY 13 - 1.6 15 25 O 15 Y Y SORHA SO - 1.6 75 95 72 94 Y Y SETIT 100 - 6.25 70 85 62 84 Y Y SETIT SO - 3.1 65 8O 48 79 Y Y CHEAL SO - 13 8O 85 78 77 Y Y CHEAL SO - 6.25 8O 8O 74 77 Y Y CHEAL, 13 - 6.25 8O 70 58 51 Y Y POLCO 100 - 13 98 1OO 98 99 Y Y POLCO 100 - 1.6 8O 85 68 69 Y Y POLCO SO - 1.6 75 8O 68 65 Y Y POLCO 25 - 1.6 75 8O 55 65 Y Y SOLNI OO - 13 98 1OO 96 99 Y Y SOLNI 13 - 13 98 1OO 96 96 Y Y XANST 100 - 6.25 90 1OO 78 91 Y Y XANST 25 - 6.25 8O 1OO 76 85 Y Y XANST 13 - 3.1 75 8O 70 75 Y Y XANST 100 + 1.6 65 8O 51 75 Y Y GALAP 100 - 13 95 1OO 94 97 Y Y GALAP 25 - 6.25 8O 95 74 90 Y Y GALAP 100 - 31 8O 95 78 92 Y Y GALAP 25 - 31 8O 95 70 88 Y Y GALAP 100 + 1.6 85 95 75 92 Y Y GALAP 25 - 1.6 8O 90 66 88 Y Y KCHSC 100 - 6.25 90 90 84 79 Y Y KCHSC 13 - 6.25 90 8O 84 65 Y Y

observed activity in % destruction 8 or 20 days after treatment 'calculated from the individual activities by Colby's formula Synergism: Y = Yes; N = No

TABLE 3 Application in Post-Emergence of Dyroxasulfone and compound Ic-1'. pyroxasulfone (A Compound B pyroxasulfone + Compound Ic-l

uSe rate use rate uSe rate Y/N3) weed gai/ha) 20 DAT (gai?ha 20 DAT (gai?ha) 20 DAT 20 DAT2 20 DAT ALOMY 100 8O 50 65 1OO -- SO 95 93 Y ALOMY 50 55 25 45 SO - 25 95 75 Y AVEFA 50 75 25 50 SO - 25 95 88 Y DIGSA 50 8O 25 75 SO - 25 100 95 Y ECHCG 50 8O 25 65 SO - 25 98 93 Y LOLMU 25 55 12.5 75 25 - 12.5 95 89 Y LOLMU 12.5 55 6.25 65 12.5 - 6.25 90 84 Y SETFA 50 85 25 70 SO - 25 98 96 Y SETVI 25 75 12.5 70 25 - 12.5 95 93 Y CHEAL 12.5 35 6.25 85 12.5 - 6.25 100 90 Y MATIN 25 O 12.5 95 25 - 12.5 98 95 Y MATIN 12.5 O 6.25 75 12.5 - 6.25 90 75 Y POLCO 12.5 35 6.25 90 12.5 - 6.25 98 94 Y 'observed activity in % destruction 20 days after treatment 'calculated from the individual activities by Colby's formula Synergism: Y = Yes; N = No 'compound Ic-1: compound of the formula Ic, where R’ is chlorine, Ris chlorine, R is ethyl, Ris difluoromethoxy and R is bromine US 2011/OO15068 A1 Jan. 20, 2011 20

TABLE 4 Application in Post-Emergence of pyroxasulfone and compound V-1 4). pyroxasulfone (A Compound B pyroxasulfone + Compound V-1

uSe rate use rate uSe rate Y/N3) weed gai/ha) 20 DAT (gai?ha 20 DAT (gai?ha) 20 DAT) 20 DAT2) 20 DAT DIGSA 12.5 50 3.13 35 12.5 - 3.125 8O 68 LOLMU 50 55 12.5 85 SO - 12.5 98 93 SETFA 50 85 12.5 70 SO - 12.5 98 96 CHEAL 25 45 6.25 60 25 - 6.25 95 78 GALAP 12.5 40 3.13 30 12.5 - 3.125 75 58 MATIN 25 O 6.25 90 25 - 6.25 95 90 observed activity in % destruction 20 days after treatment 'calculated from the individual activities by Colby's formula Synergism: Y = Yes; N = No 'compound V-1: compound of the formula V, where R’ is fluorine, R is propargyl, R2 is methyl, R26 is methyl and Y is S.

1. A herbicidal composition comprising: C-C-alkoxy, C-C-cycloalkyl and C-C2-alkyl a) a herbicide A which is 3-5-(difluoromethoxy)-1-me Substituted by a C-C-cycloalkyl radical; thyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl-4, R" is halogen or cyano; 5-dihydro-5,5-dimethyl-1,2-oxazole; and and Het is a heterocyclic radical of formula A or B: b) at least one herbicide B which is selected from proto porphyrinogen-IX-Oxidase inhibitors. (A) 2. The composition as claimed in claim 1, wherein the O herbicide B comprises at least one compound of the formula I Hi-N \ CF N (I) V O R5 (B) R7 Het R6 s it. N -N- N CH

wherein where R" is selected from the group consisting of the radicals R is selected from the group consisting of hydrogen propargyloxy, allyloxy, isopropyloxy, —C(=O) amino, methyl and propargyl; NHSONR'R'', C(=O)N NR'R'', R is selected from the group consisting of difluo O CR'R' C(=O) OR'e, - C(=O)C)– romethoxy, trifluoromethyl and methylsulfonyl: CR'R' C(=O) OR', R’ is selected from the group consisting of halogen and C(=O)C CHR-1b, C(=O)NHSONR'R'', methyl. NHSONR'R'', SONHC(=O)NR'R'', —CH-CH(Cl)CO. R'' and the radical of the for 3. The composition as claimed in claim 2, wherein the mula OC(CH), C(=O) OR'; wherein herbicide B comprises at least one compound of the formula R" is hydrogen or C-C-alkyl; Ia. R" is C-C-alkyl; R" is hydrogen or C-C-alkyl: (Ia) R" is hydrogen or C-C-alkyl or a agriculturally acceptable cation; and R" is C1-C4-alkyl, propargyl or allyl, C N CF R is hydrogen, fluorine or chlorine; R is hydrogen or together with R' forms amoiety—O C R1 Yeh (R)-N or N=C(R) NH 3 where R and Rare selected, independently of each other from the group consisting of hydrogen, C-C- 4. The composition as claimed in claim 3, where the com alkyl, C-C-haloalkyl, C-C-alkenyl, C-C-ha pound of the formula Ia is selected from the group consisting loalkenyl, C-C-alkylnyl, C-C-haloalkylnyl, of saflufenacil and butafenacil. US 2011/OO15068 A1 Jan. 20, 2011 21

5. The composition as claimed in claim 2, wherein the herbicide B comprises at least one compound of the formula Ib. (II) R2 OX (Ib) C N R2 O \ le. N R10 R4 N \ CF R8 N wherein N O O Ys N X is O or NR'', R is selected from the group consisting of propargyloxy, R3a allyloxy, isopropyloxy, the radical of the formula CH2— CH(Cl)CO R'' and the radical of the formula 6. The composition as claimed in claim 5, whereinformula NH SO CH: Ib R is fluorine, R is chlorine, R is methyl and R is R is fluorine or chlorine; cyclopropylmethyl. R' is CH or tertbutyl: 7. The composition as claimed in claim 2, wherein the R'' is CHF, or together with R' may form 1,4-butandiyl: herbicide B comprises at least one compound of the formula R" is hydrogen, C-C-alkyl or and agriculturally accept Ic. able cation. 12. The composition as claimed in claim 11, where the

(Ic) compound of the formula II is selected from the group con sisting of carfentraZone, or its salts and/or its esters, Sulfen traZone, azafenidine, oxadiargyl and oxadiazon. 13. The composition as claimed in claim 1, wherein the herbicide B comprises at least one compound of the formula III

(III) R13 O

8. The composition as claimed in claim 7, where informula R 15 N Ic R is fluorine or chlorine, R is chlorine, R is ethyl, R is difluoromethoxy and R7 is chlorine or bromine. 9. The composition as claimed in claim 2, wherein the R 14 O herbicide B comprises at least one compound of the formula Id. wherein R" is hydrogen, fluorine or chlorine; (Id) R'' is selected from the group consisting of propargyloxy, R2 O allyloxy, 1-methyl-2-propinyloxy, O CHCO. R. CH=C(Cl)CO. R'' and isopropyloxy; R" is fluorine or chlorine; or R4 N \ CF R'' and R' together form a moiety —O CH, C (=O) NR' , where R'' is a propargyl radical and X-NV 5 HN 2 N O R where the oxygen atom is meta with regard to the posi tion of R: R3 R" is hydrogen, C1-Co-alkyl or an agriculturally accept able cation. 14. The composition as claimed in claim 13, where the 10. The composition as claimed in claim 9, where in for compound of the formula III is selected from the group con mula Id R is fluorine, R is chlorine, R is methyl and R is sisting of cinidon, or its salts and/or its esters, flumiclorac, or trifluoromethyl. its salts and/or its esters, flumioxazin and flumipropyn. 11. The composition as claimed in claim 1, wherein the 15. The composition as claimed in claim 1, wherein the herbicide B comprises at least one compound of the formula herbicide compound B comprises at least one compound of II the formula IV US 2011/OO15068 A1 Jan. 20, 2011 22

IV C R19 (IV) (VI) 21 - H(R), 1S

Yn O (R)-HN.4N2O wherein N R" is chlorine or trifluoromethyl; HNN R27 R" is selected from the group consisting of hydrogen, C-C-alkoxy, —CO R', C(=O)C CH-CO. R’, C(=O)C CH(CH)CO R', and C(=O) wherein NH SO, R’’: m is 0, 1, 2, or 3: n is 0, 1, 2, 3 or 4: R" is hydrogen, fluorine or chlorine; R’ is selected from the group consisting of C-C-alkyl, R’ is hydrogen, C1-Co-alkyl or a agriculturally acceptable C-C-haloalkyl, C-C-alkenyl, C-C-haloalkenyl, cation; and C-C-alkylnyl, C-C-haloalkylnyl, C-C-cycloalkyl, R’ is C-C-alkyl. C-C-alkyl Substituted by a C-C-alkoxy radical, and C-C2-alkyl Substituted by a C-C-cycloalkyl radical; 16. The composition as claimed in claim 15, where the R’ is selected from the group consisting of halogen, compound of the formula IV is selected from the group con C-C-alkyl, C-C-haloalkyl, C-C-alkoxy, and sisting of nitrofen, bifenox, oxyfluorfen, acifluorfen, or its C-C-alkyl substituted by a C-C-alkoxy radical, it salts and/or its esters, fomesafen, lactofen, halosafen, chlor being possible for m=2 or 3 that the radicals R are nitrofen, fluornitrofen, chlomethoxyfen and nitrofluorfen. identical or different from each other; 17. The composition as claimed in claim 16, where the R’ is selected from the group consisting of halogen, compound of the formula IV is oxyfluorfen. cyano, nitro, C-C-alkyl, C-Ca-haloalkyl, C-C- 18. The composition as claimed in claim 1, wherein the alkylsulfonyl, C-C-alkoxy, C-C-alkyl Substituted by herbicide B comprises at least one compound of the formula a C-C-alkoxy radical, C-C2-alkyl Substituted by a V C-C-cycloalkyl radical, and a radical COR', it being possible for n=2,3 or 4 that the radicals Rare identical or different from each other; (V) R" is selected from the group consisting of C, -Co-alkyl, R23 O R25 C-C-haloalkyl, C-C-alkenyl, C-C-haloalkenyl, C-C-alkylnyl, C-C-haloalkylnyl, C-C-cycloalkyl, )- N/ C-C-alkyl Substituted by a C-C-alkoxy radical, and N Y C-C-alkyl substituted by a C-C-cycloalkyl radical. 21. The composition as claimed in claim 20, wherein the y-N herbicide B comprises at least one compound of the formula / \ VIa

wherein (VIa) R’ is hydrogen, fluorine or chlorine; R" is selected from the group consisting of hydrogen, C-C-alkyl, C-C-haloalkyl, C-C-alkenyl, C-C- haloalkenyl, C-C-alkynyl, C-C-haloalkynyl, C-C- alkoxy, C-C-cycloalkyl and C-C2-alkyl Substituted by a C-C-cycloalkyl radical; R is selected from the group consisting of hydrogen, amino, methyl and propargyl; R" is selected from the group consisting of hydrogen and methyl; and Y is O or S. 19. The composition as claimed in claim 18, where in 22. The composition as claimed in claim 1, containing no formula VR is fluorine, R is propargyl, R is methyl, R' safener. is methyl and Y is S. 23. The composition as claimed in claim 1, wherein the 20. The composition as claimed in claim 1, wherein the relative amount of herbicide A to the at least one herbicide B herbicide B comprises at least one compound of the formula is from 100:1 to 1:100. VI 24. (canceled) US 2011/OO15068 A1 Jan. 20, 2011

25. (canceled) 31. The method as claimed in claim 29, wherein undesir 26. (canceled) able vegetation in crop plants are controlled. 32. The method as claimed in claim 31, wherein the crop 27. (canceled) plants are crops of wheat, barley, rye, triticale, durum, rice, 28. A method for controlling undesirable vegetation, which corn, Sugarcane, Sorghum, soybean, pulse crops, peanut, Sun comprises allowing the composition as claimed in claim 1 to flower, Sugarbeet, potato, cotton, brassica crops, turf, grapes, act on plants to be controlled or their habitat. pomefruit, Stonefruit, citrus, coffee, pistachio, garden orna 29. The method for controlling undesired vegetation as mentals, bulb ornamentals, onion, garlic, conifers or decidu claimed in claim 28, which comprises applying the compo OuS trees. sition before, during and/or after the emergence of the unde 33. The method as claimed in claim 31, where the crop sirable vegitation; the herbicides A and B being applied plants are resistant to herbicides acting as protoporphyrino simultaneously or in Succession. gen-IX-Oxidase inhibitors. 30. An herbicide formulation comprising the composition as claimed in claim 1 and at least one solid or liquid carrier. c c c c c