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WO2023030934A1 - Herbicidal composition comprising phenyluracils - Google Patents

Herbicidal composition comprising phenyluracils Download PDF

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Publication number
WO2023030934A1
WO2023030934A1 PCT/EP2022/073269 EP2022073269W WO2023030934A1 WO 2023030934 A1 WO2023030934 A1 WO 2023030934A1 EP 2022073269 W EP2022073269 W EP 2022073269W WO 2023030934 A1 WO2023030934 A1 WO 2023030934A1
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WIPO (PCT)
Prior art keywords
methyl
compositions
cas
formula
inhibitors
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PCT/EP2022/073269
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French (fr)
Inventor
Liliana Parra Rapado
Tobias SEISER
Ricardo Hugo PAVON ROMERO
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Basf Se
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Publication of WO2023030934A1 publication Critical patent/WO2023030934A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • Herbicidal composition comprising phenyluracils
  • the present invention relates to herbicidal compositions comprising at least one phenyluracil of formula (I) and at least one further compound selected from herbicidally active compounds and safeners.
  • crop protection compositions it is desirable in principle to increase the specific activity of an active compound and the reliability of the effect. It is particularly desirable for the crop protection composition to control the harmful plants effectively, but at the same time to be compatible with the useful plants in question. Also desirable is a broad spectrum of activity allowing the simultaneous control of harmful plants. Frequently, this cannot be achieved using a single herbicidally active compound.
  • compositions which are highly active against unwanted harmful plants.
  • compositions should have good compatibility with useful plants.
  • compositions according to the invention should have a broad spectrum of activity.
  • the present invention relates to herbicidal compositions comprising: A) at least one phenyuracil of formula (I) wherein the substituents have the following meanings:
  • R 1 NH 2 , Ci-C 6 -alkyl
  • R 3 hydrogen or Ci-Ce-alkyl
  • R 5 halogen, CN, Ci-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylthio, (Ci- C3-alkyl)amino, di(Ci-C3-alkyl)amino, Ci-Cs-alkoxy-Ci-Cs-alkyl, C1-C3- alkoxycarbonyl;
  • R 6 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, C3-C6- haloalkenyl, Cs-Ce-haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce- alkoxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, di(Ci-C6-alkoxy)Ci-Ce-alkyl, Ci-Ce-haloalkoxy-Ci- Ce-alkyl, Cs-Ce-alkenyloxy-Ci-Ce-alkyl, Cs-Ce-haloalkenyloxy-Ci-Ce-alkyl, C3-C6- alkenyloxy-Ci-Ce-alkoxy-Ci-Ce-alkyl
  • Z phenyl or pyridyl each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy; including their agriculturally acceptable salts, amides, esters or thioesters, provided the phenyluracils of formula (I) have a carboxyl group; and at least one further active compound selected from
  • the invention relates in particular to compositions in the form of herbicidal active agrochemical compositions comprising a herbicidally effective amount of an active compound combination comprising at least one phenyluracil of formula (I) and at least one further compound selected from the herbicides B and the safeners C, as defined above, and also at least one liquid and/or solid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for agrochemical compositions.
  • the invention also relates to compositions in the form of a agrochemical composition formulated as a 1-component composition comprising an active compound combination comprising at least one phenyluracil of formula (I) and at least one further active compound selected from the herbicides B and the safeners C, and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for agrochemical compositions.
  • the invention also relates to compositions in the form of a agrochemical composition formulated as a 2-component composition comprising a first component comprising at least one phenyluracil of formula (I), a solid or liquid carrier and/or one or more surfactants, and a second component comprising at least one further active compound selected from the herbicides B and safeners C, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for agrochemical compositions.
  • a agrochemical composition formulated as a 2-component composition comprising a first component comprising at least one phenyluracil of formula (I), a solid or liquid carrier and/or one or more surfactants, and a second component comprising at least one further active compound selected from the herbicides B and safeners C, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for agrochemical compositions.
  • compositions according to the invention comprising at least one phenyluracil of formula (I) and at least one herbicide B have better herbicidal activity, i.e. better activity against harmful plants, than would have been expected based on the herbicidal activity observed for the individual compounds, or a broader activity spectrum.
  • the herbicidal activity to be expected for mixtures based on the individual compound can be calculated using Colby’s formula (see below). If the activity observed exceeds the expected additive activity of the individual compounds, synergism is said to be present.
  • the time frame within which the desired herbicidal action can be achieved, may be expanded by the compositions according to the invention comprising at least one phenyluracil of formula (I) and at least one herbicide B and optionally a safener C. This allows a more flexibly timed application of the compositons according to the present invention in comparison with the single compounds.
  • compositions according to the invention comprising both at least one phenyluracil of formula (I) and at least one of the compounds mentioned under C also have good herbicidal activity against harmful plants and better compatibility with useful plants.
  • compositions according to the invention comprising at least one phenyluracil of formula (I), at least one herbicide B and at least one of the compounds mentioned under C have better herbicidal activity, i.e. better activity against harmful plants, than would have been expected based on the herbicidal activity observed for the individual compounds, or a broader activity spectrum, and show better compatibility with useful plants than compositions comprising only one compound I and one herbicide B.
  • the invention furthermore relates to a method for controlling unwanted vegetation, in particular where crop plants are cultivated.
  • the invention also relates to a method for the desiccation or defoliation of plants.
  • the herbicidal compounds B and/or the safeners C as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
  • the herbicidal compounds B and/or the safeners C as described herein have one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions according to the invention.
  • the herbicidal compounds B and/or the safeners C as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetrade
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • Phenyluracils of formula (I), herbicidal compounds B and/or safeners C as described herein having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-Ce-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-C -alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Cio-al kylthio esters.
  • amides such as mono- and di-Ci-Ce-alkylamides or arylamides
  • esters for example as allyl esters, propargyl esters, Ci-C -alkyl esters, al
  • Preferred mono- and di-Ci-Ce-alkylamides are the methyl and the dimethylamides.
  • Preferred arylamides are, for example, the anilides and the 2-chloroanilides.
  • Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1 -methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
  • Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3- butoxypropyl ester.
  • An example of a straight-chain or branched Ci-Cw-alkylthio ester is the ethylthio ester.
  • the organic moieties mentioned in the definition of the variables R 1 to R 6 and R a to R e are - like the term halogen - collective terms for individual enumerations of the individual group members.
  • the term halogen denotes in each case fluorine, chlorine, bromine or iodine. All hydrocarbon chains can be straight-chain or branched, the prefix C n -C m denoting in each case the possible number of carbon atoms in the group.
  • Ci-C4-alkyl for example CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2Hs, CH2- CH(CH 3 ) 2 and C(CH 3 ) 3 ;
  • Ci-Cs-haloalkyl Ci-Cs-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2- chloroethyl, 2-bromoethyl, 2-iodoethyl, 1 ,1 -difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pent
  • Ci-C4-haloalkyl Ci-C4-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2- chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropy
  • Ci-Ce-haloalkyl Ci-C4-haloalkyl as mentioned above, and also, for example,
  • Cs-Ce-haloalkenyl and also the Cs-Ce-haloalkenyl moieties of Cs-Ce-haloalkenyloxy-Ci-Ce- alkyl a Cs-Ce-alkenyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-
  • Cs-Ce-alkynyl and also the Cs-Ce-alkynyl moieties of Cs-Ce-alkynyloxycarbonyl-Ci-Ce-alkyl for example 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1- pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3- butynyl, 3-methyl-1-butynyl, 1 ,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl,
  • Cs-Ce-haloalkynyl a Cs-Ce-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 1 ,1 -difl uoroprop-2-yn-1-yl,
  • Ci-C4-alkoxy for example methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy,
  • Ci-Cs-haloalkoxy a Ci-Cs-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
  • 2,2,2-trichloroethoxy pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3- chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3- dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1 -(fluoromethyl)-2-fluoroethoxy, 1 -(chloromethyl)-2-chloroethoxy, 1 -(bromo- methyl)-2-bromoethoxy;
  • Ci-C4-haloalkoxy a Ci-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
  • Ci-Cs-alkylthio for example methylthio, ethylthio, propylthio, 1 -methylethylthio;
  • Ci-C4-alkylthio for example methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1 , 1-dimethylethylthio;
  • Ci-Ce-alkylsulfonyl (Ci-Ce-alkyl-S(O)2-) and also the Ci-Ce-alkylsulfonyl moieties of Ci-Ce- alkylsulfonyl-Ci-Ce-alkyl: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1- methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1,1- dimethylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3- methylbutylsulfonyl, 1 ,1-dimethylpropylsulfonyl, 1 ,2-dimethylpropyls
  • (Ci-C3-alkyl)amino for example methylamino, ethylamino, propylamino, 1 -methylethylamino.
  • R 1 is NH 2 or Ci-Ce-alkyl; particularly preferred is CH3; also particularly preferred is NH 2 .
  • R 2 is Ci-C4-haloalkyl; particularly preferred is Ci-Cs-haloalkyl; more preferred is Ci-C 2 -haloalkyl; especially preferred is CF3.
  • R 3 is H or Ci-C4-alkyl; particularly preferred is H or CH3; more preferred is H; also more preferred is CH3.
  • R 4 is H, F or Cl; particularly preferred is H or F; especially preferred is F.
  • R 5 is halogen, Ci-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylthio or C1-C3- alkoxycarbonyl; preferably is Ci-Cs-alkoxy, Ci-Cs-haloalkoxy or Ci-Cs-alkylthio; particularly preferred is Ci-Cs-alkoxy or Ci-Cs-alkylthio; especially preferred is Ci-Cs-alkoxy; more preferred is OCH3.
  • R 6 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, Cs-Ce-haloalkenyl, Cs-Ce-haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxy-Ci-Ce- alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl; preferably is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, Ci-Ce- cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-al
  • R 6 is hydrogen or Ci-Ce-alkyl.
  • n is 1 or 2; particularly preferred is 2; also particularly preferred is 1 .
  • Q is O, also preferably is S.
  • W is O, also preferably is S.
  • X is O, also preferably is S.
  • Y is O, also preferably is S.
  • Z is phenyl or pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is phenyl or pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3 or OCH3; especially preferred is phenyl or pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH3; more preferred is phenyl or pyridyl, each of which is unsubstituted.
  • Z is phenyl or 2-pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is phenyl or 2-pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3 or OCH3; especially preferred is phenyl or 2-pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH 3 ; more preferred is phenyl or 2-pyridyl, each of which is unsubstituted.
  • Z is phenyl, which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is phenyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH 3 or OCH 3 ; especially preferred is phenyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH 3 ; also especially preferred is unsubstituted phenyl.
  • Z is pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH 3 or OCH 3 ; especially preferred is pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH 3 ; also especially preferred is unsubstituted pyridyl.
  • Z is 2-pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is 2-pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH 3 or OCH 3 ; especially preferred is 2-pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH 3 ; also especially preferred is unsubstituted 2-pyridyl.
  • Z is selected from the group consisting of Z 1 to Z 13 wherein
  • H halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H.
  • Z is selected from the group consisting of Z 1 , Z 2 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 and Z 11 as defined above; particularly preferred is selected from the group consisting of Z 1 , Z 4 , Z 5 , Z 6 and Z 7 as defined above; more particularly preferred is selected from the group consisting of Z 1 , Z 4 , Z 5 , Z 6 and Z 7 as defined above; especially preferred is selected from the group consisting of Z 1 and Z 7 as defined above; more preferred is selected from Z 1 as defined above; also more preferred is selected from Z 7 as defined above.
  • Z is selected from the group consisting of Z 1 , Z 2 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 and Z 11 as defined above, wherein
  • R a , R b , R c , R d and R e independently of one another are
  • H halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H; particularly preferred is selected from the group consisting of Z 1 , Z 4 , Z 5 , Z 6 and Z 7 , as defined above, wherein
  • R a , R b , R c , R d and R e independently of one another are
  • H halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH 3 ; more preferred H; especially preferred is selected from the group consisting of Z 1 and Z 7 as defined above, wherein
  • R a , R b , R c , R d and R e independently of one another are
  • H halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH 3 or OCH 3 ; especially preferred H, F, Cl or CH3; more preferred H; more preferred is Z 1 as defined above, wherein R a , R b , R c , R d and R e independently of one another are
  • H halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H; also more preferred is Z 7 as defined above, wherein
  • R a , R b , R c , R d and R e independently of one another are
  • H halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H.
  • R 1 is CH 3 ;
  • R 2 is Ci-Cs-haloalkyl
  • R 3 is hydrogen or CH 3 ;
  • R 4 is H or halogen
  • R 5 is Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylthio;
  • R 6 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, C3-C6- haloalkenyl, Cs-Ce-haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce- alkoxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, n is 1;
  • X is O or S
  • Z is phenyl or 2-pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3, OCH3.
  • R 1 is CH 3 ;
  • R 2 is Ci-Cs-haloalkyl
  • R 3 is hydrogen
  • R 4 is F
  • R 5 is Ci-Cs-alkoxy
  • R 6 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, n is 1;
  • Z is phenyl, optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH 3 , OCH 3 .
  • phenyluracils of formula (I. a) corresponds to formula (I) wherein R 1 is CH3, R 2 is CF3, R 3 is H, n is 1 , Q, W, X and Y are O, and Z is Z-1 as defined, wherein R a , R b , R c and R d are H: wherein the variables R 4 , R 5 , and R 6 have the meanings, in particular the preferred meanings, as defined above; special preference is given to phenyuracils of formulae (I .a.1) to (I. a.36) of Table A, where the definitions of the variables R 4 , R 5 , and R 6 are of particular importance for the phenyluracils according to the invention not only in combination with one another but in each case also on their own:
  • phenyuracils of formula (l.b) preferably phenyuracils of formulae (l.b.1) to (l.b.36), which differ from the corresponding phenyuracils of formulae (l.a.1) to (I. a.36) only in that Q is S:
  • phenyuracils of formula (l.e) preferably the phenyuracils of formulae (l.c.1) to (l.c.36), which differ from the corresponding phenyuracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-2, wherein R a , R b , R c and R e are H:
  • phenyuracils of formula (l.d) preferably the phenyuracils of formulae (l.d.1) to (l.d.36), which differ from the corresponding phenyuracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-3, wherein R a , R b , R d and R e are H:
  • phenyluracils of formula (l.f) preferably the phenyluracils of formulae (l.f.1) to (l.f.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-5, wherein R a , R c and R d are H:
  • phenyluracils of formula (l.g) preferably the phenyluracils of formulae (l.g.1) to (l.g.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-6, wherein R a , R b and R d are H:
  • phenyluracils of formula (l.h) preferably the phenyluracils of formulae (l.h.1) to (l.h.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-7, wherein R a , R b and R c are H:
  • phenyluracils of formula (l.i) preferably the phenyluracils of formulae (l.i.1) to (l.i.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-7, wherein R a , R b and R c are H, and Q is S:
  • phenyluracils of formula (l.k) preferably the phenyluracils of formulae (l.k.1) to (l.k.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-8, wherein R b , R c and R e are H:
  • phenyluracils of formula (I. I) preferably the phenyluracils of formulae (1.1.1) to (1.1.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-9, wherein R a , R c and R e are H:
  • phenyluracils of formula (l.m) preferably the phenyluracils of formulae (l.m.1) to (l.m.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-10, wherein R a , R b and R e are H:
  • phenyluracils of formula (l.n) preferably the phenyluracils of formulae (l.n.1) to (l.n.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-11 , wherein R a , R b and R c are H:
  • phenyluracils of formula (l.p) preferably the phenyluracils of formulae (l.p.1) to (l.p.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-13, wherein R a , R d and R e are H:
  • phenyluracils of formula (l.q) preferably the phenyluracils of formulae (l.q.1) to (l.q.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only that R 5 is SCH 3 :
  • phenyluracils of formula (l.r) preferably the phenyluracils of formulae (l.r.1) to (l.r.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that R 3 is CH 3 :
  • the composition contains as component A at least one phenyluracil selected from formulae (I. a), (l.h), (l.q), and (l.r).
  • the composition contains as component A at least one phenyluracil of formula (I. a).
  • the composition contains as component A at least one phenyluracil of formula (l.h).
  • the composition contains as component A at least one phenyluracil selected from formulae (l.a.1) to (1.a.36), (l.h.1) to (l.h.36), (l.q.1) to (l.q.36) and (l.r.1) to (l.r.36); particularly preferred at least one phenyluracil selected from formulae (l.a.1) to (1.a.36).
  • the composition contains as component A at least one phenyluracil selected from formulae (I. a.19), (I. a.20), (I. a.21), (I. a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20); particularly preferred at least one phenyluracil selected from formulae (I. a.19), (I. a.20), (I. a.21), (l.a.25), (l.a.26), (l.a.27) and (l.a.31); also particularly preferred at least one phenyluracil selected from formulae (I. a.20), (l.h.20), (l.q.20) and (l.r.20).
  • the composition contains as component A the phenyluracil of formula (l.a.19).
  • the composition contains as component A the phenyluracil of formula (I. a.20).
  • the composition contains as component A the phenyluracil of formula (I. a.21).
  • the composition contains as component A the phenyluracil of formula (l.a.25).
  • the composition contains as component A the phenyluracil of formula (l.a.26). According to a particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (I. a.27).
  • the composition contains as component A the phenyluracil of formula (I. a.31).
  • composition contains as component A the phenyluracil of formula (l.h.20).
  • composition contains as component A the phenyluracil of formula (l.q.20).
  • composition contains as component A the phenyluracil of formula (l.r.20).
  • especially preferred phenyluracils of formula (I) are methyl rac-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; methyl (2S)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; methyl (2R)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; rac-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl
  • the phenyluracils of formula (I) can be prepared by reaction of compounds of formula (II) with alkylating agents of formula (III) in the presence of a base in analogy to known processes (e.g.
  • L 1 is a leaving group such as halogen.
  • alkylating agents of formula (III) are commercially available or can be prepared by known methods (e.g. WO 11/137088).
  • PG is a protecting group selected from the group consisting of Ci-Ce-alkyl or (tri-Ci-C6-alkyl)silyl-Ci-C4-alkyl.
  • the compounds of formula (II) can be prepared by treating the compounds of formula (VI), wherein “PG” is methyl, with boron tribromide in a solvent such as dichloromethane at temperatures ranging from 0 °C to 150 °C.
  • the reaction may in principle be carried out in substance. However, preference is given to reacting the amines of formula (VII) with the oxazinones of formula (VIII) in an organic solvent. Suitable in principle are all solvents which can dissolve the amines of formula (VII) and the oxazinones of formula (VIII) at least partly, and preferably fully under reaction conditions.
  • Suitable solvents are halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone, tert-butyl methyl ketone, cyclohexanone; organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluor
  • acids inorganic acids like hydrochloric acid, hydrobromic acid or sulfuric acid
  • organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid
  • acids inorganic acids like hydrochloric acid, hydrobromic acid or sulfuric acid
  • organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid
  • the acids are generally employed in equimolar amounts, in excess or, if appropriate, be used as solvent, however they can also be employed in catalytic amounts.
  • Those compounds of formula (VI), wherein R 1 is NH 2 , Ci-Ce-alkyl or Cs-Ce-alkynyl can be prepared by amination or alkylation of those compounds of formula (VI), wherein R 1 is H.
  • Such amination or alkylation can be conducted in analogy to known processes (e.g. WO 05/054208; WO 06/125746).
  • Ci-Ce-alkylhalides and alkinylhalides can be used as alkylation reagents.
  • Suitable amination reagents are known from literature (e.g. US 6333296 or DE 10005284)
  • the reaction may in principle be carried out in substance. However, preference is given to reacting the amines of formula (VII) with the oxazinones of formula (VIII) in an organic solvent. Suitable in principle are all solvents which are capable of dissolving the amines of formula (VII) and the oxazinones of formula (VIII) at least partly, and preferably fully under reaction conditions.
  • Suitable solvents are halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF); nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone, tert-butyl methyl ketone, cyclohexanone; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert.-butanol, organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid,
  • acids inorganic acids like hydrochloric acid, hydrobromic acid or sulfuric acid
  • organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid
  • acids inorganic acids like hydrochloric acid, hydrobromic acid or sulfuric acid
  • organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid
  • the acids are generally employed in equimolar amounts, in excess or, if appropriate, be used as solvent, however they can also be employed in catalytic amounts.
  • the compound of formula (IX) can be prepared by reduction followed by a Sandmeyer reaction from a compound of formula (X).
  • Reduction of the nitro group of compounds of formula (X) can be carried out by catalytic hydrogenation in hydrogen gas at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature.
  • a metal catalyst such as palladium supported on an inert carrier such as activated carbon
  • Bromination of the resulting amine is facilitated by diazotization with an alkyl nitrite (e.g. isoamyl nitrite) followed by treatment with a copper (I) bromide and/or copper (II) bromide in a solvent such as acetonitrile at a temperature ranging from 0 °C to the reflux temperature of the solvent to give the corresponding compound of formula (IX).
  • an alkyl nitrite e.g. isoamyl nitrite
  • a solvent such as acetonitrile
  • the compounds of formula (X) required for the preparation of compounds of formula (IX) can be prepared by reaction of compounds of formula (XI) with compounds of formula (XII) in the presence of a base:
  • L 3 is a leaving group such as halogen.
  • the reaction is carried out in an organic solvent.
  • Suitable solvents are halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N '-dimethylpropylene urea (DMPLI), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP).
  • halogenated hydrocarbons such as
  • suitable bases include metal-containing bases and nitrogen-containing bases.
  • suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxide, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate, as well as alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and
  • the bases are generally employed in equimolar amounts or in excess; however they can also be employed as solvent, or, if appropriate, in catalytic amounts.
  • the reaction can be carried out by adding bis(1 , 1 -dimethylethyl) dicarbonate (CAS 24424-99-5) to compounds of formula (XIII) in an organic solvent.
  • bis(1 , 1 -dimethylethyl) dicarbonate CAS 24424-99-5
  • the addition of a base can be advantages.
  • suitable solvents are halogenated hydrocarbons such as dichloromethane, 1,2- dichloroethane, chloroform.
  • suitable bases are nitrogen-containing bases such as 4-(dimethylamino)pyridine (DMAP), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1 ,5-diazabicyclo[4.3.0]non-5-ene (DBN).
  • DMAP 4-(dimethylamino)pyridine
  • DBU 1,8-diazabicyclo[5.4.0]undec-7-ene
  • DBN 1,5-diazabicyclo[4.3.0]non-5-ene
  • compositions according to the present invention comprise at least one phenyluracil of formula (I) and at least one further active compound B (herbicide B).
  • the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1).
  • These are compounds that inhibit lipid biosynthesis. Inhibition of the lipid biosynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter termed ACC herbicides) or through a different mode of action (hereinafter termed non-ACC herbicides).
  • ACC herbicides belong to the group A of the HRAC classification system whereas the non-ACC herbicides belong to the group N of the HRAC classification.
  • compositions contain at least one ALS inhibitor (herbicide b2).
  • the herbicidal activity of these compounds is based on the inhibition of acetolactate synthase and thus on the inhibition of the branched chain amino acid biosynthesis.
  • These inhibitors belong to the group B of the HRAC classification system.
  • the compositions contain at least one inhibitor of photosynthesis (herbicide b3).
  • the herbicidal activity of these compounds is based either on the inhibition of the photosystem II in plants (so-called PSII inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis.
  • PSII inhibitors are preferred.
  • compositions contain at least one inhibitor of protoporphyrinogen-IX-oxidase (herbicide b4).
  • the herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase.
  • These inhibitors belong to the group E of the HRAC classification system.
  • the compositions contain at least one bleacher-herbicide (herbicide b5).
  • the herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis.
  • These include compounds which inhibit carotenoid biosynthesis by inhibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).
  • PDS inhibitors group F1 of HRAC classification
  • HPPD inhibitors 4-hydroxyphenylpyruvate-dioxygenase
  • DOXsynthase group F4 of HRAC class
  • compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher -
  • compositions contain at least one EPSP synthase inhibitor (herbicide b6).
  • the herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid biosynthesis in plants.
  • These inhibitors belong to the group G of the HRAC classification system.
  • compositions contain at least one glutamine synthetase inhibitor (herbicide b7).
  • the herbicidal activity of these compounds is based on the inhibition of glutamine synthetase, and thus on the inhibition of the aminoacid biosynthesis in plants.
  • These inhibitors belong to the group H of the HRAC classification system.
  • compositions contain at least one DHP synthase inhibitor (herbicide b8).
  • DHP synthase inhibitor herebicide b8
  • the herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase.
  • These inhibitors belong to the group I of the HRAC classification system.
  • the compositions contain at least one mitosis inhibitor (herbicide b9).
  • the herbicidal activity of these compounds is based on the disturbance or inhibition of microtubule formation or organization, and thus on the inhibition of mitosis.
  • These inhibitors belong to the groups K1 and K2 of the HRAC classification system. Among these, compounds of the group K1 , in particular dinitroanilines, are preferred.
  • the compositions contain at least one VLCFA inhibitor (herbicide b10).
  • the herbicidal activity of these compounds is based on the inhibition of the synthesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants.
  • These inhibitors belong to the group K3 of the HRAC classification system.
  • compositions contain at least one cellulose biosynthesis inhibitor (herbicide b11).
  • the herbicidal activity of these compounds is based on the inhibition of the biosynthesis of cellulose and thus on the inhibition of the synthesis of cell walls in plants.
  • These inhibitors belong to the group L of the HRAC classification system.
  • compositions contain at least one decoupler herbicide (herbicide b12).
  • the herbicidal activity of these compounds is based on the disruption of the cell membrane.
  • These inhibitors belong to the group M of the HRAC classification system.
  • the compositions contain at least one auxinic herbicide (herbicide b13).
  • auxinic herbicide include compounds that mimic auxins, i.e. plant hormones, and affect the growth of the plants. These compounds belong to the group O of the HRAC classification system.
  • compositions contain at least one auxin transport inhibitor (herbicide b14).
  • the herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants.
  • These compounds belong to the group P of the HRAC classification system.
  • compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b4, b5, b6, b7, b9, b10 and b13.
  • compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b2, b4, b6, b7, b10 and b13.
  • compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b4, b6, b7and b10.
  • herbicides B which can be used in combination with the phenyluracils of formula (I) according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors:
  • ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethy
  • a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide.
  • a preferred embodiment of the invention relates to those compositions comprising at least one triazine herbicide.
  • a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide; b4) from the group of the protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumi
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33- 7) and rimisoxafen
  • HPPD inhibitors benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, bipyrazone, fenpyrazone, cypyrafluone, tripyrasulfone, benquitrione, dioxopyr
  • the isoxazoline compounds of the formula (II) are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576; among the VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b11) from the group of the cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5- pentafluorphenyloxy-1 4 -[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1); b12) from the group of the decoupler herbicides: dinoseb, dinoterb and DNOC and its salts; b13) from the group of the auxinic herbicides:
  • 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts
  • Preferred herbicides B that can be used in combination with the phenyluracils of the formula (I) according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors: clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P- ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-4- cyclopropyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,
  • 3-methyl-imidazolidin-2-one (CAS 1844836-64-1); b4) from the group of the protoporphyrinogen-IX oxidase inhibitors: acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon- ethyl, cyclopyranil, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen- ethyl, saflufenacil, sulfentrazone, tiafenacil, trifludimoxazin, epyrifenacil, N-ethy
  • 2,4-D and its salts and esters aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2- hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluor
  • herbicides B that can be used in combination with the phenyluracils of the formula (I) according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'- Chloro-4-cyclopropyl-2'-fluoro[1 , 1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran- 3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1'-biphenyl]-3-yl)-5-hydroxy- 2.2.6.6-tetramethyl-2H-pyran-3(6H)
  • esprocarb, prosulfocarb, thiobencarb and triallate from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsulam, propoxycarbazon-so
  • herbicides B are the herbicides B as defined above; in particular the herbicides B.1 - B.215 listed below in table B:
  • compositions according to the present invention comprise at least one phenyluracil of formula (I) and at least one safener C.
  • Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the present compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or postemergence application of the useful plant.
  • the safeners and the phenyluracils of formula (I) and/or the herbicides B can be applied simultaneously or in succession.
  • Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro- 5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salt
  • Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3- oxazolidine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).
  • Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526- 07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
  • Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphtalic anhydride, 4- (dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
  • safeners C which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1 - C.17 listed below in table C:
  • the active compounds B of groups b1) to b15) and the active compounds C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998.
  • the assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this substance was only assigned to one mechanism of action.
  • Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative in the compositions according to the invention.
  • suitable salts include those, where the counterion is an agriculturally acceptable cation.
  • suitable salts of dicamba are dicamba-sodium, dicamba- potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba- isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba- trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine.
  • a suitable ester are dicamba-methyl and dicamba-butotyl.
  • Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D- diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D- dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2- hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4- D-sodium and 2,4-D-N,N,N-trimethylethanolammonium (2,4-D choline).
  • esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4- D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D- methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
  • Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB- dimethylammonium.
  • Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl.
  • Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop- butotyl and dichlorprop-isoctyl.
  • Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethyl- ammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA- isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA- olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
  • a suitable salt of MCPB is MCPB sodium.
  • a suitable ester of MCPB is MCPB-ethyl.
  • Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyral id-tris-(2- hydroxypropyl)ammonium.
  • Example of suitable esters of clopyralid is clopyralid-methyl.
  • Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.
  • Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine.
  • a suitable ester of picloram is picloram-isoctyl.
  • a suitable salt of triclopyr is triclopyr-triethylammonium.
  • Suitable esters of triclopyr are for example triclopyr-ethyl and triclopyr-butotyl.
  • Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium.
  • Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA- potassium and 2,3,6-TBA-sodium.
  • Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid- dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
  • Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate- trimesium (sulfosate).
  • a suitable salt of glufosinate is for example glufosinate-ammonium.
  • a suitable salt of glufosinate-P is for example glufosinate-P-ammonium.
  • Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil- heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
  • Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.
  • Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
  • Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P- dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.
  • a suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.
  • a suitable salt of naptalam is for example naptalam-sodium.
  • Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor- dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor- triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.
  • a suitable salt of quinclorac is for example quinclorac-dimethylammonium.
  • a suitable salt of quinmerac is for example quinmerac-dimethylammonium.
  • a suitable salt of imazamox is for example imazamox-ammonium.
  • Suitable salts of imazapic are for example imazapic-ammonium and imazapic- isopropylammonium.
  • Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr- isopropylammonium.
  • a suitable salt of imazaquin is for example imazaquin-ammonium.
  • Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr- isopropylammonium.
  • a suitable salt of topramezone is for example topramezone-sodium.
  • the composition comprises as herbicidal active compound B or component B at least one, preferably exactly one herbicide B.
  • the composition comprises as herbicidal active compounds B or component B at least two, preferably exactly two herbicides B different from each other.
  • the composition comprises as herbicidal active compounds B or component B at least three, preferably exactly three herbicides B different from each other.
  • the composition comprises as safening component C or component C at least one, preferably exactly one safener C.
  • the composition comprises as component B at least one, preferably exactly one herbicide B, and as component C at least one, preferably exactly one, safener C.
  • the composition comprises at least two, preferably exactly two, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
  • the composition comprises at least three, preferably exactly three, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
  • the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), and as component B at least one, preferably exactly one, herbicide B.
  • the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), and at least two, preferably exactly two, herbicides B different from each other.
  • the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), and at least three, preferably exactly three, herbicides B different from each other.
  • the composition comprises as component A at least one, preferably exactly one one phenyluracil of formula (I), preferably of formula (I. a), and as component C at least one, preferably exactly one, safener C.
  • the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.
  • the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), at least two, preferably exactly two herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
  • the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), at least three, preferably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b1), in particular selected from the group consisting of clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, metamifop, pinoxaden, profoxydim, sethoxydim, tepraloxydim, tralkoxydim, esprocarb, ethofume
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b2), in particular selected from the group consisting of bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorsulfuron, clorimuron, cyclosulfamuron, diclosulam, florasulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazamox-ammonium, imazapic, imazapic-ammoni
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting (l.a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, bentazon, bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, bromoxynil-potassium, diuron, fluometuron, hexazinone, isoproturon, linuron, metamitron, metribuzin, paraquat-dichloride, propanil, simazin, terbutryn and terbuth
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b4), in particular selected from the group consisting of acifluorfen, butafencil, carfenetrazone-ethyl, flumioxazin, fomesafen, oxadiargyl, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, epyrifenacil, 3-[2-chloro-5
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b5), in particular selected from the group consisting of amitrole, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquintrone, fluometuron, flurochloridone, isoxaflutole, mesotrione, norflurazone, oxotrione (CAS 1486617-21-3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b6), in particular selected from the group consisting of glyphosate, glyphosate-ammonium, glyphosate- dimethylammonium , glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate) and glyphosate-potassium.
  • a phenyluracil of formula (I) especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b7), in particular selected from the group consisting of glufosinate, glufosinate-ammonium, glufosinate- P and glufosinate-P-ammonium.
  • a phenyluracil of formula (I) especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20),
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b9), in particular selected from the group consisting of pendimethalin and trifluralin.
  • a phenyluracil of formula (I) especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of acetochlor, butachlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone.
  • a phenyluracil of formula (I) especially an active compound from the group consisting of (I .a.19), (
  • compositions comprising in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I. a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as defined above.
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b11 ), in particular indaziflam, isoxaben and triaziflam.
  • a phenyluracil of formula (I) especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b13), in particular selected from the group consisting of 2,4-D, 2,4-D-isobutyl, 2,4-D-dimethylammonium, 2,4-D-N,N,N-trimethylethanolammonium, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-methyl, aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium,
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b14), in particular selected from the group consisting of diflufenzopyr, diflufenzopyr-sodium, dymron, indanofan and diflufenzopyr-sodium.
  • a phenyluracil of formula (I) especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20
  • a phenyluracil of formula (I) especially an active compound from the group consisting of (I .a.19
  • the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one safener C, in particular selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-o
  • binary compositions includes compositions comprising one or more, for example 1, 2 or 3, active compounds of the formula (I) and either one or more, for example 1, 2 or 3, herbicides B or one or more safeners C.
  • ternary compositions includes compositions comprising one or more, for example 1, 2 or 3, active compounds of the formula (I), one or more, for example 1, 2 or 3, herbicides B and one or more, for example 1, 2 or 3, safeners C.
  • the weight ratio of the active compounds A:B is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.
  • the weight ratio of the active compounds A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.
  • the relative proportions by weight of the components A:B are generally in the range of from 1 :1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1 :75 to 75: 1
  • the weight ratio of the components A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1
  • the weight ratio of the components B:C is generally in the range of from 1 : 1000 to 1000: 1 , preferably in the range of from 1 :500 to 500: 1 , in particular in the range of from 1 :250 to 250: 1 and particularly preferably in the range of from 1 :75
  • Further preferable mixing ratios by weight of the present phenyluracils of formula (I) as component A to one or more compounds selected from the group consisting of the herbicides B according to the present invention are about 1 :0.1 , 1 :0.2, 1 :0.3, 1 :0.5, 1 :0.6, 1 :0.7, 1 :0.8, 1 :1 , 1 :1.2, 1 :1.4, 1 :1.6, 1 :1.8, 1 :2, 1 :2.2, 1 :2.4, 1 :2.6, 1 :2.8, 1 :3, 1 :5, 1 :7, 1 :10, 1 :15, 1 :20, 1 :30, 1 :40 and 1 :50.
  • about 1 :2 includes a range of 1 : 1.8 to 1 :2.2.
  • weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.
  • compositions mentioned below comprising the phenyluracils of formula (I) as defined and the substance(s) as defined in the respective row of table 1 ; especially preferred comprising as only herbicidal active compounds the phenyluracil of formula (I) as defined and the substance(s) as defined in the respective row of table 1 ; most preferably comprising as only active compounds the phenyluracils of formula (I) as defined and the substance(s) as defined in the respective row of table 1 .
  • compositions 1.1 to 1.3887 comprising the phenyluracil of formula (I. a.20) and the substance(s) as defined in the respective row of table 1 :
  • Composition 1.200 for example comprises the phenyluracil (I. a.20) and cinmethylin (B.200) (see table 1 , entry 1.200; as well as table B, entry B.200).
  • Composition 2.200 for example comprises the phenyluracil (I. a.19) (see the definition for compositions 2.1 to 2.3887 below) and cinmethylin (B.200) (see table 1 , entry 1.200; as well as table B, entry B.200).
  • Composition 7.200 for example comprises imazapyr (B.35) (see the definition for compositions 7.1 to 7.3887 below), the phenyluracil (I. a.20) and cinmethylin (B.200) (see table 1 , entry 1.200; as well as table B, entry B.200).
  • compositions 2.1. to 2.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.19).
  • compositions 3.1. to 3.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.2 as further herbicide B.
  • compositions 4.1. to 4.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.8 as further herbicide B.
  • compositions 5.1. to 5.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.30 as further herbicide B.
  • compositions 6.1. to 6.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.32 as further herbicide B.
  • compositions 7.1. to 7.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.35 as further herbicide B.
  • compositions 8.1. to 8.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.38 as further herbicide B.
  • compositions 9.1. to 9.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.40 as further herbicide B.
  • compositions 10.1. to 10.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.51 as further herbicide B.
  • compositions 11.1. to 11.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.55 as further herbicide B.
  • compositions 12.1. to 12.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.56 as further herbicide B.
  • compositions 13.1. to 13.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.64 as further herbicide B.
  • compositions 14.1. to 14.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.66 as further herbicide B.
  • compositions 15.1. to 15.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.67 as further herbicide B.
  • compositions 16.1. to 16.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.68 as further herbicide B.
  • compositions 17.1. to 17.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.69 as further herbicide B.
  • compositions 18.1. to 18.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.73 as further herbicide B.
  • compositions 19.1. to 19.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.76 as further herbicide B.
  • compositions 20.1. to 20.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.81 as further herbicide B.
  • compositions 21.1. to 21.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.82 as further herbicide B.
  • compositions 22.1. to 22.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.85 as further herbicide B.
  • compositions 23.1. to 23.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.88 as further herbicide B.
  • compositions 24.1. to 24.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.89 as further herbicide B.
  • compositions 25.1. to 25.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.94 as further herbicide B.
  • compositions 26.1. to 26.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.95 as further herbicide B.
  • compositions 27.1. to 27.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.98 as further herbicide B.
  • compositions 28.1. to 28.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.100 as further herbicide B.
  • compositions 29.1. to 29.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.103 as further herbicide B.
  • compositions 30.1. to 30.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.103 and B.67 as further herbicides B.
  • compositions 31.1. to 31.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.103 and B.76 as further herbicides B.
  • compositions 32.1. to 32.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.103 and B.82 as further herbicides B.
  • compositions 33.1. to 33.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.104 as further herbicide B.
  • compositions 34.1. to 34.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.104 and B.67 as further herbicides B.
  • compositions 35.1. to 35.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.104 and B.76 as further herbicides B.
  • compositions 36.1. to 36.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.104 and B.82 as further herbicides B.
  • compositions 37.1. to 37.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.106 as further herbicide B.
  • compositions 38.1. to 38.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.107 as further herbicide B.
  • compositions 39.1. to 39.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B. 107 and B.67 as further herbicides B.
  • compositions 40.1. to 40.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B. 107 and B.76 as further herbicides B.
  • compositions 41.1. to 41.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B. 107 and B.82 as further herbicides B.
  • compositions 42.1. to 42.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.109 as further herbicide B.
  • compositions 43.1. to 43.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.111 as further herbicide B.
  • compositions 44.1. to 44.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.111 and B.67 as further herbicides B.
  • compositions 45.1. to 45.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.111 and B.76 as further herbicides B.
  • compositions 46.1. to 46.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.111 and B.82 as further herbicides B.
  • compositions 47.1. to 47.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B. 116 as further herbicide B.
  • compositions 48.1. to 48.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.67 as further herbicides B.
  • compositions 49.1. to 49.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.94 as further herbicides B.
  • compositions 50.1. to 50.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.103 as further herbicides B.
  • compositions 51.1. to 51.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.128 as further herbicides B.
  • compositions 52.1. to 52.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.104 as further herbicides B.
  • compositions 53.1. to 53.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.107 as further herbicides B.
  • compositions 54.1. to 54.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.111 as further herbicides B.
  • compositions 55.1. to 55.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.122 as further herbicide B.
  • compositions 56.1. to 56.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.126 as further herbicide B.
  • compositions 57.1. to 57.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.128 as further herbicide B.
  • compositions 58.1. to 58.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.131 as further herbicide B.
  • compositions 59.1. to 59.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.132 as further herbicide B.
  • compositions 60.1. to 60.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.133 as further herbicide B.
  • compositions 61.1. to 61.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.135 as further herbicide B.
  • compositions 62.1. to 62.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.137 as further herbicide B. Also especially preferred are compositions 63.1. to 63.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.138 as further herbicide B.
  • compositions 64.1. to 64.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.140 as further herbicide B.
  • compositions 65.1. to 65.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.145 as further herbicide B.
  • compositions 66.1. to 66.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.153 as further herbicide B.
  • compositions 67.1. to 67.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.156 as further herbicide B.
  • compositions 68.1. to 68.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.171 as further herbicide B.
  • compositions 69.1. to 69.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.174 as further herbicide B.
  • compositions 70.1. to 70.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.202 as further herbicide B.
  • compositions 71.1. to 71.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.a.20-stereoisomer 1).
  • compositions 72.1. to 72.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.a.20-stereoisomer 2).
  • compositions 73.1. to 73.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.21).
  • compositions 74.1. to 74.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.25).
  • compositions 75.1. to 75.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.26).
  • compositions 76.1. to 76.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.27).
  • compositions 77.1. to 77.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.31).
  • compositions 78.1. to 78.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.h.20).
  • compositions 79.1. to 79.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.q.20).
  • compositions 80.1. to 80.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.r.20).
  • compositions 81.1. to 81.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.2 as further herbicide B.
  • compositions 82.1. to 82.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.8 as further herbicide B.
  • compositions 83.1. to 83.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.30 as further herbicide B.
  • compositions 84.1. to 84.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.32 as further herbicide B.
  • compositions 85.1. to 85.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.35 as further herbicide B.
  • compositions 86.1. to 86.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.38 as further herbicide B.
  • compositions 87.1. to 87.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.40 as further herbicide B.
  • compositions 88.1. to 88.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.51 as further herbicide B.
  • compositions 89.1. to 89.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.55 as further herbicide B.
  • compositions 90.1. to 90.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.56 as further herbicide B.
  • compositions 91.1. to 91.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.64 as further herbicide B.
  • compositions 92.1. to 92.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.66 as further herbicide B.
  • compositions 93.1. to 93.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.67 as further herbicide B.
  • compositions 94.1. to 94.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.68 as further herbicide B.
  • compositions 95.1. to 95.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.69 as further herbicide B.
  • compositions 96.1. to 96.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.73 as further herbicide B.
  • compositions 97.1. to 97.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.76 as further herbicide B.
  • compositions 98.1. to 98.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.81 as further herbicide B.
  • compositions 99.1. to 99.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.82 as further herbicide B.
  • compositions 100.1. to 100.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.85 as further herbicide B.
  • compositions 101.1. to 101.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.88 as further herbicide B.
  • compositions 102.1. to 102.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.89 as further herbicide B.
  • compositions 103.1. to 103.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.94 as further herbicide B.
  • compositions 104.1. to 104.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.95 as further herbicide B.
  • compositions 105.1. to 105.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.98 as further herbicide B.
  • compositions 106.1. to 106.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.100 as further herbicide B.
  • compositions 107.1. to 107.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.103 as further herbicide B.
  • compositions 108.1. to 108.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.103 and B.67 as further herbicides B.
  • compositions 109.1. to 109.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.103 and B.76 as further herbicides B.
  • compositions 110.1. to 110.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.103 and B.82 as further herbicides B.
  • compositions 111.1. to 111.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.104 as further herbicide B.
  • compositions 112.1. to 112.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.104 and B.67 as further herbicides B.
  • compositions 113.1. to 113.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.104 and B.76 as further herbicides B.
  • compositions 114.1. to 114.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.104 and B.82 as further herbicides B.
  • compositions 115.1. to 115.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.106 as further herbicide B.
  • compositions 116.1. to 116.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.107 as further herbicide B.
  • compositions 117.1. to 117.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B. 107 and B.67 as further herbicides B.
  • compositions 118.1. to 118.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B. 107 and B.76 as further herbicides B.
  • compositions 119.1. to 119.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B. 107 and B.82 as further herbicides B.
  • compositions 120.1. to 120.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.109 as further herbicide B.
  • compositions 121.1. to 121.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.111 as further herbicide B.
  • compositions 122.1. to 122.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.111 and B.67 as further herbicides B.
  • compositions 123.1. to 123.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.111 and B.76 as further herbicides B.
  • compositions 124.1. to 124.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.111 and B.82 as further herbicides B.
  • compositions 125.1. to 125.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B. 116 as further herbicide B.
  • compositions 126.1. to 126.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.67 as further herbicides B.
  • compositions 127.1. to 127.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.94 as further herbicides B.
  • compositions 128.1. to 128.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.103 as further herbicides B.
  • compositions 129.1. to 129.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.128 as further herbicides B.
  • compositions 130.1. to 130.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.104 as further herbicides B.
  • compositions 131.1. to 131.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.107 as further herbicides B.
  • compositions 132.1. to 132.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.111 as further herbicides B.
  • compositions 133.1. to 133.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.122 as further herbicide B.
  • compositions 134.1. to 134.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.126 as further herbicide B.
  • compositions 135.1. to 135.3887 which differ from the corresponding compositions 173.1 to 73.3887 only in that they additionally comprise B.128 as further herbicide B.
  • compositions 136.1. to 136.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.131 as further herbicide B.
  • compositions 137.1. to 137.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.132 as further herbicide B.
  • compositions 138.1. to 138.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.133 as further herbicide B.
  • compositions 139.1. to 139.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.135 as further herbicide B. Also especially preferred are compositions 140.1. to 140.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.137 as further herbicide B.
  • compositions 141.1. to 141.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.138 as further herbicide B.
  • compositions 142.1. to 142.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.140 as further herbicide B.
  • compositions 143.1. to 143.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.145 as further herbicide B.
  • compositions 144.1. to 144.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.153 as further herbicide B.
  • compositions 145.1. to 145.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.156 as further herbicide B.
  • compositions 146.1. to 146.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.171 as further herbicide B.
  • compositions 147.1. to 147.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.174 as further herbicide B.
  • compositions 148.1. to 148.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.202 as further herbicide B.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one composition according to the invention.
  • An agrochemical composition comprises a pesticidally effective amount of at least one composition according to the invention.
  • effective amount denotes an amount of the active ingredients, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in crops (i.e. cultivated plants) and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated crop or material, the climatic conditions and the specific composition according to the invention used.
  • the compounds A and ottionally B and/or C, their N-oxides, salts or derivatives can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • agrochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g.
  • WP WP
  • SP WS
  • DP DS
  • pressings e.g. BR, TB, DT
  • granules e.g. WG, SG, GR, FG, GG, MG
  • insecticidal articles e.g. LN
  • gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF).
  • agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalene, alkylated
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharides e.g. cellulose, starch
  • fertilizers
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
  • Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides.
  • polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable colorants are pigments of low water solubility and water- soluble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
  • Examples for agrochemical composition types and their preparation are: i) Water-soluble concentrates (SL, LS)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a composition according to the invention In an agitated ball mill, 20-60 wt% of a composition according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
  • WG, SG Water-dispersible granules and water-soluble granules
  • a composition according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • wt% of a composition according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
  • wt% dispersants e.g. sodium lignosulfonate
  • wetting agents e.g. alcohol ethoxylate
  • solid carrier e.g. silica gel
  • a acomposition according to the invention In an agitated ball mill, 5-25 wt% of a acomposition according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1-5 wt% thickener e.g. carboxymethylcellulose
  • a composition according to the invention 5-20 wt% of a composition according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alcohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a composition according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g.
  • diphenylmethene-4,4’-diisocyanate are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol).
  • a protective colloid e.g. polyvinyl alcohol.
  • the addition of a polyamine results in the formation of polyurea microcapsules.
  • the monomers amount to 1-10 wt%.
  • the wt% relate to the total CS composition.
  • a composition according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%.
  • solid carrier e.g. finely divided kaolin
  • a composition according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%.
  • solid carrier e.g. silicate
  • Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • compositions according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
  • organic solvent e.g. aromatic hydrocarbon
  • the agrochemical compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1-1 wt% colorants.
  • auxiliaries such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1-1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds.
  • the compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
  • Methods for applying phenyluracils of formula (I) and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material.
  • compound I or the compositions thereof, respectively are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1, preferably 1:10 to 10:1.
  • the user applies the agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • either individual components of the agrochemical composition according to the invention or partially premixed components e. g. agrochemical components comprising phenyluracils of formula (I) and/or active substances from the groups B and/or C may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the agrochemical composition according to the invention or partially premixed components, e. g. components comprising phenyluracils of formula (I) and active substances from the groups B and/or C, can be applied jointly (e.g. after tank mix) or consecutively.
  • a first embodiment of the invention relates to compositions in the form of a agrochemical composition formulated as a 1 -component composition comprising the at least one active phenyluracil of formula (I) or the at least one active phenyluracil of formula (I) (active compound A) and at least one further active compound selected from the herbicides B and the safeners C and also a solid or liquid carrier and, if appropriate, one or more surfactants.
  • a second embodiment of the invention relates to compositions in the form of a agrochemical composition formulated as a 2-component composition
  • a first formulation comprising the at least one active compound A, a solid or liquid carrier and, if appropriate, one or more surfactants
  • a second component comprising at least one further active compound selected from the herbicides B and safeners C, a solid or liquid carrier and, if appropriate, one or more surfactants.
  • the active compound A and the at least one further active compound B and/or C can be formulated and applied jointly or separately, simultaneously or in succession, before, during or after the emergence of the plants. In case of separate application, the order of the application of the active compounds A, B and/or C is of minor importance. The only thing that is important is that the at least one active compound A and the at least one further active compound B and/or C are present simultaneously at the site of action, i.e. are at the same time in contact with or taken up by the plant to be controlled / safened.
  • the compositions according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).
  • compositions according to the invention control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
  • compositions according to the invention have an outstanding herbicidal activity against undesired vegetation, i.e. against a broad spectrum of economically important harmful monocotyledonous and dicotyledonous weeds.
  • compositions according to the invention are used to control monocotyledonous weeds.
  • Examples of monocotyledonous weeds on which the compositions according to the invention act efficiently are selected from the genera Hordeum spp., Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Brachiaria spp., Leptochloa spp., Avena spp., Cyperus spp., Axonopris spp., Sorghum spp., and Melinus spp..
  • Preferred examples of monocotyledonous weeds on which the compositions according to the invention act efficiently are selected from the species Hordeum murinum, Echinochloa crus- galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis, Digitaria insularis, Eriochloa gracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea, Panicum miliaceum, Lolium multiflorum, Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, and Melinus repens.
  • Especially preferred examples of monocotyledonous weeds on which the compositions according to the invention act efficiently are selected from the species Echinochloa spp., Digitaria spp., Setaria spp., Eleusine spp. and Brachiarium spp.
  • compositions according to the invention are used to control dicotyledonous weeds.
  • dicotyledonous weeds on which the compositions according to the invention act efficiently are selected from the genera Amaranthus spp., Erigeron spp., Conyza spp., Polygonum spp., Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp., Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp., Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., llrtica spp., Sida spp, Portulaca spp., Richardia spp.
  • Preferred examples of dicotyledonous weeds on which the compositions according to the invention act efficiently are selected from the species Amaranthus spinosus, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum offi cinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis (Conyza bonariensis), Senecio vulgaris, Lamium amplexicaule, Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra, Sinapis arvensis, ll
  • dicotyledonous weeds on which the compositions according to the invention act efficiently are selected from the species Amaranthus spp., Erigeron spp., Conyza spp., Kochia spp. and Abutilon spp.
  • compositions according to the invention are applied to the plants mainly by spraying the leaves.
  • the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha).
  • the herbicidal compositions may also be applied by the low- volume or the ultra-low-volume method, or in the form of microgranules.
  • herbicidal compositions according to the present invention can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
  • the herbicidal compositions according to the present invention can be applied pre- or postemergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition of the invention, of a crop plant. If the active compounds A and B and, if appropriate C, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post- directed, lay-by).
  • the composition according to the invention can be applied by treating seed.
  • the treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula (I) according to the invention or the compositions prepared therefrom.
  • the herbicidal compositions can be applied diluted or undiluted.
  • seed comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms.
  • seed describes corns and seeds.
  • the seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
  • compositions of the present invention on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth.
  • other crop protection agents for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth.
  • miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies.
  • Non-phytotoxic oils and oil concentrates can also be added.
  • the amounts of active substances applied are, depending on the kind of effect desired, from 0.001 to 3 kg per ha, preferably from 0.005 to 2.5 kg per ha, more preferably from 0.01 to 2 kg per ha and in particular from 0.025 to 1.5 kg per ha.
  • the rates of application of the phenyluracil of formula (I) according to the present invention are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.
  • the application rates of the phenyluracil of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.
  • the application rate of the phenyluracil of formula (I) is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha.
  • the required application rates of herbicidal compounds B are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
  • the required application rates of safeners C are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
  • amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
  • the amounts of active substances applied i.e. A and B and, if appropriate, C are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
  • the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
  • the herbicide phenyluracil and the herbicide compound B and/or the herbicide safener compound C are applied in a time frame that allows simultaneous action of the active ingredients on the plants, preferably within a time-frame of at most 35 days, in particular at most 14 days.
  • compositions according to the invention can additionally be employed in a further number of crop plants for eliminating undesirable plants.
  • all the crop plants (cultivated plants) mentioned herein are understood to comprise all species, subspecies, variants and/or hybrids which belong to the respective cultivated plants, including but not limited to winter and spring varieties, in particular in cereals such as wheat and barley, as well as oilseed rape, e.g. winter wheat, spring wheat, winter barley etc..
  • corn is also known as Indian corn or maize (Zea mays) which comprises all kinds of corn such as field corn and sweet corn.
  • all maize or corn subspecies and/or varieties are comprised, in particular flour corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy corn (Zea mays var. ceratina), amylomaize (high amylose Zea mays varieties), pod corn or wild maize (Zea mays var. tunicata) and striped maize (Zea mays var. japonica).
  • soybean cultivars are classifiable into indeterminate and determinate growth habit, whereas Glycine soja, the wild progenitor of soybean, is indeterminate (PNAS 2010, 107 (19) 8563-856).
  • the indeterminate growth habit (Maturity Group, MG 00 to MG 4.9) is characterized by a continuation of vegetative growth after flowering begins whereas determinate soybean varieties (Maturity Group, (MG) 5 to MG 8) characteristically have finished most of their vegetative growth when flowering begins.
  • all soybean cultivars or varieties are comprised, in particular indeterminate and determinate cultivars or varieties.
  • suitable crops are the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.
  • Preferred crops are Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum s
  • Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, peas, lentils, peanuts or permanent crops.
  • compositions according to the invention can also be used in crops which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • crops as used herein includes also (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
  • Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome.
  • Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
  • Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination.
  • one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants.
  • the process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or hae been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
  • Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®. However, most of the herbicide tolerance traits have been created via the use of transgenes.
  • ALS acetolactate synthase
  • Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
  • HPPD 4- hydroxyphenylpyruvate dioxygenase
  • Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.
  • Transgenic corn events comprising herbicide tolerance genes are for example, but not excluding others, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO- 01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.
  • Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
  • Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
  • Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.
  • Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants.
  • Transgenes which have most frequently been used are toxin genes of Bacillus spec, and synthetic variants thereof, like cry1A, crylAb, cry1 Ab-Ac, crylAc, cry1A.1O5, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20.
  • genes of plant origin have been transferred to other plants.
  • genes coding for protease inhibitors like CpTI and pinll.
  • a further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes.
  • An example for such a transgene is dvsnf7.
  • Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411 , MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.
  • Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701, MON87751 and DAS-81419.
  • Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531 , MON757, MON 1076, MON 15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.
  • Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
  • Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
  • Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-00410-5.
  • Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process.
  • Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.
  • Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art.
  • detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations “International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the “Center for Environmental Risk Assessment (CERA)” (http://cera-amc.org/GMCropDatabase), as well as in patent applications, like EP3028573 and WG2017/011288.
  • ISAAA International Service for the Acquisition of Agri-biotech Applications
  • CERA Center for Environmental Risk Assessment
  • compositions according to the invention on crops may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
  • plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • a modified amount of ingredients or new ingredients specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
  • compositions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable.
  • crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton
  • compositions have been found for the desiccation and/or defoliation of plants, processes for preparing these compositions, and methods for desiccating and/or defoliating plants using the compositions according to the invention.
  • compositions according to the invention are suitable in particular for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
  • Example 1 - stepl terf-Butyl N-(2,5-difluoro-4-nitro-phenyl)carbamate WO 2023/030934 l uo PCT/EP2022/073269
  • Example 1 - step 6 3-[4-bromo-2-fluoro-5-(2-methoxyphenoxy)phenyl]-6-(trifluoromethyl)-1 H- pyrimidine-2, 4-dione
  • Example 1 - step 7 3-[4-bromo-2-fluoro-5-(2-methoxyphenoxy)phenyl]-1-methyl-6-(trifluoro- methyl)-pyrimidine-2, 4-dione
  • Example 1 step 8 3-[4-bromo-2-fluoro-5-(2-hydroxyphenoxy)phenyl]-1-methyl-6-(trifluoro- methyl)-pyrimidine-2, 4-dione
  • the culture containers used were plastic pots containing loamy sand with approximately 3.0% of humus as substrate.
  • the seeds of the test plants were sown separately for each species.
  • the active compounds suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles.
  • the containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants unless this was adversely affected by the active compounds.
  • test plants were grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. To this end, the test plants were either sown directly, and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
  • the plants were kept at 10 - 25°C and 20 - 35°C, respectively.
  • test period extended over 2 to 4 weeks. During this time, the plants were tended and their response to the individual treatments was evaluated.
  • Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage or normal course of growth. A good herbicidal activity is given at values of at least 70, and very good herbicidal activity is given at values of at least 85.
  • the respective components A and B, and if appropriate, C were formulated as a 5% by weight strength emulsion concentrate and, with addition of the amount of solvent system, introduced into the spray liquor used for applying the active compound.
  • X percent activity using active compound A at an application rate a
  • the phenyuracils of formula (I) were used as an EC formulation having an active ingredient concentration of 5% (5w/w%).
  • Herbicides B group b.1 : herbicide B.1 : clethodim (240 g/L EC) group b.2 : herbicide B.32 imazapic (240 g/L SL) herbicide B.35 imazapyr (240 g/L SL) herbicide B.40 imazethapyr (240 g/L SL) group b.4 : herbicide B.94 saflufenacil (342 g/L SC) herbicide B.95 sulfentrazone (480 g/L SC) herbicide B.96 trifludimoxazin (500 g/L, SC) methyl (1S,4R)-4-[[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-1 ,2-oxazol-5- yl]carbonyl]amino]-cyclopent-2-en-1-carboxylat (CAS 2365468-20-6) group b.5
  • a.i. means active ingredient, based on 100 % active ingredient.
  • POST post emergent
  • GS growth stage of the weed
  • PRE pre-emergent
  • Example 1 Synergistic herbicidal action of the composition 1.1 (POST, GS 12-16)
  • Example 2 Synergistic herbicidal action of the composition1.32 (POST, GS 12-16)
  • Example 3 Synergistic herbicidal action of the composition 1.40 (POST, GS 12-16)
  • Example 4 Synergistic herbicidal action of the composition 1.94 (POST, GS 12-16)
  • Example 5 Synergistic herbicidal action of the composition 1.95 (POST, GS 12-16)
  • Example 6 Synergistic herbicidal action of the composition 1.96 (POST, GS 12-16)
  • Example 7 Synergistic herbicidal action of the composition 1.111 (POST, GS 12-16)
  • Example 8 Synergistic herbicidal action of the composition 1.116 (POST, GS 12-16)
  • Example 9 Synergistic herbicidal action of the composition 1.122 (POST, GS 12-16)
  • Example 10 Synergistic herbicidal action of the composition 1.124 (POST, GS 12-16)
  • Example 11 Synergistic herbicidal action of the composition 1.126 (POST, GS 12-16)
  • Example 12 Synergistic herbicidal action of the composition 1.131 (POST, GS 12-16)
  • Example 13 Synergistic herbicidal action of the composition 1.135 (POST, GS 12-16)
  • Example 14 Synergistic herbicidal action of the composition 1.144 (POST, GS 12-16)
  • Example 15 Synergistic herbicidal action of the composition 1.145 (POST, GS 12-16)
  • Example 16 Synergistic herbicidal action of the composition 1.156 (POST, GS 12-16)
  • Example 18 Synergistic herbicidal action of the composition 1.35 (PRE)
  • Example 19 Synergistic herbicidal action of the composition 1.40 (PRE)
  • Example 20 Synergistic herbicidal action of the composition 1.94 (PRE)
  • Example 21 Synergistic herbicidal action of the composition 1.95 (PRE)
  • Example 22 Synergistic herbicidal action of the composition 1 .96 (PRE)
  • Example 23 Synergistic herbicidal action of the composition 1.111 (PRE)
  • Example 24 Synergistic herbicidal action of the composition 1.126 (PRE)
  • Example 25 Synergistic herbicidal action of the composition 1.131 (PRE)
  • Example 26 Synergistic herbicidal action of the composition 1.135 (PRE)
  • Example 28 Synergistic herbicidal action of the composition 71.40 (POST; GS 16-18)
  • Example 29 Synergistic herbicidal action of the composition 71.96 (POST; GS 16-18)
  • Example 30 Synergistic herbicidal action of the composition 71.116 (POST; GS 16-18)
  • Example 31 Synergistic herbicidal action of the composition 71.122 (POST; GS 16-18)
  • Example 32 Synergistic herbicidal action of the composition 71.144 (POST; GS 16-18)
  • Example 33 Synergistic herbicidal action of the composition 71.40 (PRE)
  • Example 34 Synergistic herbicidal action of the composition 71.96 (PRE)
  • Example 35 Synergistic herbicidal action of the composition 71.131 (PRE)
  • Example 36 Synergistic herbicidal action of the composition 71.144 (PRE)
  • Example 37 Synergistic herbicidal action of the composition 72.40 (POST; GS 16-18/31)
  • Example 38 Synergistic herbicidal action of the composition 72.96 (POST; GS 16-18/31)
  • Example 39 Synergistic herbicidal action of the composition 72.116 (POST; GS 16-18/31)
  • Example 40 Synergistic herbicidal action of the composition 72.122 (POST; GS 16-18/31)
  • Example 41 Synergistic herbicidal action of the composition 72.144 (POST; GS 16-18/31)
  • Example 42 Synergistic herbicidal action of the composition 72.40 (PRE)
  • Example 43 Synergistic herbicidal action of the composition 72.96 (PRE)
  • Example 44 Synergistic herbicidal action of the composition 72.131 (PRE)
  • Example 45 Synergistic herbicidal action of the composition 72.144 (PRE)
  • Example 46 Synergistic herbicidal action of the composition 73.1 (POST, GS 16-31)
  • Example 47 Synergistic herbicidal action of the composition 73.32 (POST, GS 16-31)
  • Example 48 Synergistic herbicidal action of the composition 73.40 (POST, GS 16-31)
  • Example 49 Synergistic herbicidal action of the composition 73.94 (POST, GS 16-31)
  • Example 50 Synergistic herbicidal action of the composition 73.95 (POST, GS 16-31)
  • Example 51 Synergistic herbicidal action of the composition 73.96 (POST, GS 16-31)
  • Example 52 Synergistic herbicidal action of the composition 73.116 (POST, GS 16-31)
  • Example 53 Synergistic herbicidal action of the composition 73.122 (POST, GS 16-31)
  • Example 54 Synergistic herbicidal action of the composition 73.124 (POST, GS 16-31)
  • Example 55 Synergistic herbicidal action of the composition 73.131 (POST, GS 16-31)
  • Example 56 Synergistic herbicidal action of the composition 73.144 (POST, GS 16-31)
  • Example 57 Synergistic herbicidal action of the composition 73.145 (POST, GS 16-31)
  • Example 58 Synergistic herbicidal action of the composition 73.156 (POST, GS 16-31)
  • Example 59 Synergistic herbicidal action of the composition 73.40 (PRE)
  • Example 60 Synergistic herbicidal action of the composition 73.96 (PRE)
  • Example 61 Synergistic herbicidal action of the composition 73.131 (PRE)
  • Example 62 Synergistic herbicidal action of the composition 73.144 (PRE)
  • Example 63 Synergistic herbicidal action of the composition comprising phenyluracil (I. a.20) and methyl (1S,4R)-4-[[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-1,2-oxazol-5-yl]carbonyl]amino]- cyclopent-2-en-1-carboxylat (CAS 2365468-20-6;) (POST, GS 12-16; assessment 7 DAT)

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Abstract

The present invention relates to herbicidal compositions comprising at least one phenyluracil of formula (I), wherein the variables are defined as given in the specification, and at least one further active compound selected from herbicides of classes b1) to b15) and safeners C.

Description

Herbicidal composition comprising phenyluracils
Description
The present invention relates to herbicidal compositions comprising at least one phenyluracil of formula (I) and at least one further compound selected from herbicidally active compounds and safeners.
In the case of crop protection compositions, it is desirable in principle to increase the specific activity of an active compound and the reliability of the effect. It is particularly desirable for the crop protection composition to control the harmful plants effectively, but at the same time to be compatible with the useful plants in question. Also desirable is a broad spectrum of activity allowing the simultaneous control of harmful plants. Frequently, this cannot be achieved using a single herbicidally active compound.
With many highly effective herbicides, there is the problem that their compatibility with useful plants, in particular dicotyledonous crop plants, such as cotton, oilseed rape and graminaceous plants, such as barley, millet, corn, rice, wheat and sugar cane, is not always satisfactory, i.e. in addition to the harmful plants, the crop plants, too, are damaged on a scale which cannot be tolerated. By reducing the application rates, the useful plants are spared; however, naturally, the extent of the control of harmful plants decreases, too.
Frequently, it is a problem that herbicides can only be applied within a narrow time frame in order to achieve the desired herbicidal action, which time frame may be unpredictably influenced by weather conditions.
It is known that special combinations of different specifically active herbicides result in enhanced activity of an herbicide component in the sense of a synergistic effect. In this manner, it is possible to reduce the application rates of herbicidally active compounds required for controlling the harmful plants.
Furthermore, it is known that in some cases joint application of specifically acting herbicides with organic active compounds, some of which may also have herbicidal activity, allows better crop plant compatibility to be achieved. In these cases, the active compounds act as antidotes or antagonists and are also referred to as safeners, since they reduce or even prevent damage to the crop plants.
It is an object of the present invention to provide herbicidal compositions which are highly active against unwanted harmful plants. At the same time, the compositions should have good compatibility with useful plants. In addition, the compositions according to the invention should have a broad spectrum of activity.
This and further objects are achieved by the herbicidal compositions below.
This application incorporates by reference EP application no. 21194011.9.
Accordingly, the present invention relates to herbicidal compositions comprising: A) at least one phenyuracil of formula (I)
Figure imgf000003_0001
wherein the substituents have the following meanings:
R1 NH2, Ci-C6-alkyl;
R2 Ci-Ce-haloalkyl;
R3 hydrogen or Ci-Ce-alkyl;
R4 H or halogen;
R5 halogen, CN, Ci-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylthio, (Ci- C3-alkyl)amino, di(Ci-C3-alkyl)amino, Ci-Cs-alkoxy-Ci-Cs-alkyl, C1-C3- alkoxycarbonyl;
R6 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, C3-C6- haloalkenyl, Cs-Ce-haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce- alkoxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, di(Ci-C6-alkoxy)Ci-Ce-alkyl, Ci-Ce-haloalkoxy-Ci- Ce-alkyl, Cs-Ce-alkenyloxy-Ci-Ce-alkyl, Cs-Ce-haloalkenyloxy-Ci-Ce-alkyl, C3-C6- alkenyloxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkylthio-Ci-Ce-alkyl, Ci-Ce-alkylsulfinyl- Ci-Ce-alkyl, Ci-Ce-alkylsulfonyl-Ci-Ce-alkyl, Ci-Ce-alkylcarbonyl-Ci-Ce-alkyl, Ci-Ce- alkoxycarbonyl-Ci-Ce-alkyl, Ci-Ce-haloalkoxycarbonyl-Ci-Ce-alkyl, C3-C6- alkenyloxycarbonyl-Ci-Ce-alkyl, Cs-Ce-alkynyloxycarbonyl-Ci-Ce-alkyl n 1 to 3;
Q O or S;
W O or S;
X O or S;
Y O or S;
Z phenyl or pyridyl, each of which is optionally substituted by 1 to 4 substituents selected from the group consisting of halogen, CN, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy, Ci-Ce-haloalkoxy; including their agriculturally acceptable salts, amides, esters or thioesters, provided the phenyluracils of formula (I) have a carboxyl group; and at least one further active compound selected from
B) herbicides of class b1) to b15): b1) lipid biosynthesis inhibitors; b2) acetolactate synthase inhibitors (ALS inhibitors); b3) photosynthesis inhibitors; b4) protoporphyrinogen-IX oxidase inhibitors, b5) bleacher herbicides; b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors); b7) glutamine synthetase inhibitors; b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); b9) mitosis inhibitors; b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors); b11) cellulose biosynthesis inhibitors; b12) decoupler herbicides; b13) auxinic herbicides; b14) auxin transport inhibitors; and b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M- isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tetflupyrolimet, triaziflam, tridiphane, 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)- 4-pyridazinol (CAS 499223-49-3) and its salts and esters, 6-chloro-4-(2,7- dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5); including their agriculturally acceptable salts or derivatives; and
C) safeners.
The invention relates in particular to compositions in the form of herbicidal active agrochemical compositions comprising a herbicidally effective amount of an active compound combination comprising at least one phenyluracil of formula (I) and at least one further compound selected from the herbicides B and the safeners C, as defined above, and also at least one liquid and/or solid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for agrochemical compositions.
The invention also relates to compositions in the form of a agrochemical composition formulated as a 1-component composition comprising an active compound combination comprising at least one phenyluracil of formula (I) and at least one further active compound selected from the herbicides B and the safeners C, and at least one solid or liquid carrier and/or one or more surfactants and, if desired, one or more further auxiliaries customary for agrochemical compositions.
The invention also relates to compositions in the form of a agrochemical composition formulated as a 2-component composition comprising a first component comprising at least one phenyluracil of formula (I), a solid or liquid carrier and/or one or more surfactants, and a second component comprising at least one further active compound selected from the herbicides B and safeners C, a solid or liquid carrier and/or one or more surfactants, where additionally both components may also comprise further auxiliaries customary for agrochemical compositions.
Surprisingly, the compositions according to the invention comprising at least one phenyluracil of formula (I) and at least one herbicide B have better herbicidal activity, i.e. better activity against harmful plants, than would have been expected based on the herbicidal activity observed for the individual compounds, or a broader activity spectrum. The herbicidal activity to be expected for mixtures based on the individual compound can be calculated using Colby’s formula (see below). If the activity observed exceeds the expected additive activity of the individual compounds, synergism is said to be present.
Moreover, the time frame, within which the desired herbicidal action can be achieved, may be expanded by the compositions according to the invention comprising at least one phenyluracil of formula (I) and at least one herbicide B and optionally a safener C. This allows a more flexibly timed application of the compositons according to the present invention in comparison with the single compounds.
The compositions according to the invention comprising both at least one phenyluracil of formula (I) and at least one of the compounds mentioned under C also have good herbicidal activity against harmful plants and better compatibility with useful plants.
Surprisingly, the compositions according to the invention comprising at least one phenyluracil of formula (I), at least one herbicide B and at least one of the compounds mentioned under C have better herbicidal activity, i.e. better activity against harmful plants, than would have been expected based on the herbicidal activity observed for the individual compounds, or a broader activity spectrum, and show better compatibility with useful plants than compositions comprising only one compound I and one herbicide B.
The invention furthermore relates to a method for controlling unwanted vegetation, in particular where crop plants are cultivated.
The invention also relates to a method for the desiccation or defoliation of plants.
As used herein, the terms "controlling" and "combating" are synonyms.
As used herein, the terms "undesirable vegetation" and "harmful plants" are synonyms.
If the phenyluracils of formula (I), the herbicidal compounds B and/or the safeners C as described herein are capable of forming geometrical isomers, for example E/Z isomers, it is possible to use both, the pure isomers and mixtures thereof, in the compositions according to the invention.
If the phenyluracils of formula (I), the herbicidal compounds B and/or the safeners C as described herein have one or more centers of chirality and, as a consequence, are present as enantiomers or diastereomers, it is possible to use both, the pure enantiomers and diastereomers and their mixtures, in the compositions according to the invention.
Within the substituents of the phenyuracils of formula (I), instead of hydrogen also the corresponding isotope deuterium can be used.
If the phenyluracils of formula (I), the herbicidal compounds B and/or the safeners C as described herein have ionizable functional groups, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four hydrogen atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, C1-C4- alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tris(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2- hydroxyeth-1-oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hydroxyethyl)ammonium (trolamine salt), tris(2- hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N- trimethylethanolammonium (choline salt), furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis- (3-aminopropyl)methylamine and diethylenetriamine.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogensulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.
Phenyluracils of formula (I), herbicidal compounds B and/or safeners C as described herein having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-Ce-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-C -alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Cio-al kylthio esters. Preferred mono- and di-Ci-Ce-alkylamides are the methyl and the dimethylamides. Preferred arylamides are, for example, the anilides and the 2-chloroanilides. Preferred alkyl esters are, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1-methylhexyl), meptyl (1 -methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters. Preferred Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, for example the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3- butoxypropyl ester. An example of a straight-chain or branched Ci-Cw-alkylthio ester is the ethylthio ester.
Further embodiments of the present invention are evident from the claims, the description and the examples. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention.
The organic moieties mentioned in the definition of the variables R1 to R6 and Ra to Re are - like the term halogen - collective terms for individual enumerations of the individual group members. The term halogen denotes in each case fluorine, chlorine, bromine or iodine. All hydrocarbon chains can be straight-chain or branched, the prefix Cn-Cm denoting in each case the possible number of carbon atoms in the group.
Examples of such meanings are:
Ci-Cs-alkyl and also the Ci-Cs-alkyl moieties of di(Ci-C3-alkyl)amino, Ci-Cs-alkoxy-Ci-Cs- alkyl: for example CH3, C2H5, n-propyl and CH(CH3)2;
Ci-C4-alkyl: for example CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2Hs, CH2- CH(CH3)2 and C(CH3)3;
Ci-Ce-alkyl and also the Ci-Ce-alkyl moieties of Ci-Ce-cyanoalkyl, Ci-Ce-alkyoxy-Ci-Ce- alkyl, Ci-Ce-alkoxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, di(Ci-C6-alkoxy)Ci-Ce-alkyl, Ci-Ce-haloalkoxy-Ci- Ce-alkyl, Cs-Ce-alkenyloxy-Ci-Ce-alkyl, Cs-Ce-haloalkenyloxy-Ci-Ce-alkyl, Cs-Ce-alkenyloxy-Ci- Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkylthio-Ci-Ce-alkyl, Ci-Ce-alkylsulfinyl-Ci-Ce-alkyl, Ci-Ce- alkylsulfonyl-Ci-Ce-alkyl, Ci-Ce-alkylcarbonyl-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, C1- Ce-haloalkoxycarbonyl-Ci-Ce-alkyl, Cs-Ce-alkenyloxycarbonyl-Ci-Ce-alkyl, C3-C6- alkynyloxycarbonyl-Ci-Ce-alkyl: Ci-C4-alkyl as mentioned above, and also, for example, n- pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1 , 1-dimethylpropyl, 1 ,2-dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4- methylpentyl, 1 , 1-dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1 , 1 ,2-trimethylpropyl, 1 ,2,2- trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, preferably methyl, ethyl, n- propyl, 1 -methylethyl, n-butyl, 1 , 1— dimethylethyl, n-pentyl or n-hexyl;
Ci-Cs-haloalkyl: Ci-Cs-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2- chloroethyl, 2-bromoethyl, 2-iodoethyl, 1 ,1 -difluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2- chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2- chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3- trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl;
Ci-C4-haloalkyl: Ci-C4-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2- chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2- fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2- chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3- trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4- fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1 ,1 , 2, 2, -tetrafluoroethyl and 1- trifluoromethyl-1 ,2,2,2-tetrafluoroethyl;
Ci-Ce-haloalkyl: Ci-C4-haloalkyl as mentioned above, and also, for example,
5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl,
6-chlorohexyl, 6-bromohexyl, 6-iodohexyl and dodecafluorohexyl;
Cs-Ce-alkenyl and also the Cs-Ce-alkenyl moieties of Cs-Ce-alkenyloxy-Ci-Ce-alkyl, C3-C6- alkenyloxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, Cs-Ce-alkenyloxycarbonyl-Ci-Ce-alkyl: for example 1- propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1 -propenyl, 2- methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2- butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3- methyl-3-butenyl, 1 ,1-dimethyl-2-propenyl, 1 ,2-dimethyl-1 -propenyl, 1 ,2-dimethyl-2-propenyl, 1- ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1- methyl-1-pentenyl, 2-methyl-1 -pentenyl, 3-methyl-1 -pentenyl, 4-methyl-1-pentenyl, 1-methyl- 2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3- pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,
2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1-dimethyl-2-butenyl, 1 ,1- dimethyl-3-butenyl, 1 ,2-dimethyl-1-butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3-butenyl, 1 ,3- dimethyl-1-butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3- dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3- dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2- ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1- ethyl-2-methyl-1 -propenyl and 1-ethyl-2-methyl-2-propenyl;
Cs-Ce-haloalkenyl and also the Cs-Ce-haloalkenyl moieties of Cs-Ce-haloalkenyloxy-Ci-Ce- alkyl: a Cs-Ce-alkenyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 2-chloroprop-2-en-1-yl, 3-chloroprop-2-en-
1-yl, 2,3-dichloroprop-2-en-1-yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3- dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2-en-1- yl, 3,3-dibromoprop-2-en-1-yl, 2,3,3-tribromo-2-en-1-yl or 2,3-dibromobut-2-en-1-yl;
Cs-Ce-alkynyl and also the Cs-Ce-alkynyl moieties of Cs-Ce-alkynyloxycarbonyl-Ci-Ce-alkyl: for example 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1- pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3- butynyl, 3-methyl-1-butynyl, 1 ,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl,
3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,
2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1- pentynyl, 4-methyl-2-pentynyl, 1 ,1-dimethyl-2-butynyl, 1 ,1-dimethyl-3-butynyl, 1 ,2-dimethyl-3- butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2- ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl;
Cs-Ce-haloalkynyl: a Cs-Ce-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 1 ,1 -difl uoroprop-2-yn-1-yl,
3-chloroprop-2-yn-1-yl, 3-bromoprop-2-yn-1-yl, 3-iodoprop-2-yn-1-yl, 4-fluorobut-2-yn-1-yl, 4- chlorobut-2-yn-1-yl, 1 ,1-difluorobut-2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1-yl, 5-iodopent-4-yn-1-yl, 6-fluorohex-4-yn-1-yl or 6-iodohex-5-yn-1-yl;
Ci-Cs-alkoxy and also the Ci-Cs-alkoxy moieties of Ci-Cs-alkoxy-Ci-Cs-alkyl, C1-C3- alkoxycarbonyl: for example methoxy, ethoxy, propoxy;
Ci-C4-alkoxy: for example methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy,
1 -methylpropoxy, 2-methylpropoxy and 1 ,1 -dimethylethoxy;
Ci-Ce-alkoxy and also the Ci-Ce-alkoxy moieties of Ci-Ce-alkyoxy-Ci-Ce-alkyl, Ci-Ce- alkoxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, di(Ci-C6-alkoxy)Ci-Ce-alkyl, Cs-Ce-alkenyloxy-Ci-Ce-alkoxy-Ci- Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl: Ci-C4-alkoxy as mentioned above, and also, for example, pentoxy, 1 -methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1 ,1 -dimethylpropoxy, 1 ,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1 -ethylpropoxy, hexoxy, 1 -methylpentoxy, 2- methyl pentoxy, 3-methylpentoxy, 4-methylpentoxy, 1 ,1 -dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3- dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethyl butoxy,
2-ethylbutoxy, 1 ,1 ,2-trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1 -ethyl- 1 -methylpropoxy and 1- ethyl-2-methylpropoxy. Ci-Cs-haloalkoxy: a Ci-Cs-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3- chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3- dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1 -(fluoromethyl)-2-fluoroethoxy, 1 -(chloromethyl)-2-chloroethoxy, 1 -(bromo- methyl)-2-bromoethoxy;
Ci-C4-haloalkoxy: a Ci-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2- fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2- trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,
2.2.2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3- chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3- dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1 -(fluoromethyl)-2-fluoroethoxy, 1 -(chloromethyl)-2-chloroethoxy, 1 -(bromo- methyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy and nonafluorobutoxy;
Ci-Ce-haloalkoxy and also the Ci-Ce-haloalkoxy moieties of Ci-Ce-haloalkoxy-Ci-Ce-alkyl, Ci-Ce-haloalkoxycarbonyl-Ci-Ce-alkyl: a Ci-C4-haloalkoxy as mentioned above, and also, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
Ci-Cs-alkylthio: for example methylthio, ethylthio, propylthio, 1 -methylethylthio;
Ci-C4-alkylthio: for example methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1 , 1-dimethylethylthio;
Ci-Ce-alkylthio and also the Ci-Ce-alkylthio moieties of Ci-Ce-alkylthio-Ci-Ce-alkyl: C1-C4- alkylthio as mentioned above, and also, for example, pentylthio, 1-methylbutylthio, 2-methyl- butylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 ,1-di- methylpropylthio, 1 ,2-dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3-methyl- pentylthio, 4-methylpentylthio, 1 , 1-dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethylbutylthio,
2.2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthio, 2- ethylbutylthio, 1 , 1 ,2-trimethylpropylthio, 1 ,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1- ethyl-2-methylpropylthio;
Ci-Ce-alkylsulfinyl (Ci-Ce-alkyl-S(=O)-) and also the Ci-Ce-alkylsulfinyl moieties of Ci-Ce- alkylsulfinyl-Ci-Ce-alkyl: for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-me- thylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1 ,1-di- methylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3- methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1 , 1-dimethylpropylsulfinyl,
1.2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3- methylpentylsulfinyl, 4-methylpentyl-sulfinyl, 1 , 1-dimethylbutylsulfinyl, 1 ,2-dimethylbutylsulfinyl,
1.3-dimethylbutyl-sulfi nyl , 2,2-dimethylbutylsulfi nyl , 2, 3-dimethylbutylsulfinyl , 3,3-dimethylbutyl- sulfinyl, 1 -ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1 , 1 ,2-trimethylpropylsulfinyl, 1 ,2,2- trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl;
Ci-Ce-alkylsulfonyl (Ci-Ce-alkyl-S(O)2-) and also the Ci-Ce-alkylsulfonyl moieties of Ci-Ce- alkylsulfonyl-Ci-Ce-alkyl: for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1- methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1,1- dimethylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3- methylbutylsulfonyl, 1 ,1-dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2- dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2- methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1 ,1 -dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethyl- butylsulfonyl, 3,3-dimethylbutylsulfonyl, 1 -ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1 , 1 ,2-trimethyl- propylsulfonyl, 1 ,2,2-trimethylpropylsulfonyl, 1 -ethyl- 1-methylpropylsulfonyl and 1-ethyl-2- methylpropylsulfonyl;
(Ci-C3-alkyl)amino: for example methylamino, ethylamino, propylamino, 1 -methylethylamino.
The preferred embodiments of the invention mentioned herein below shall be understood as being preferred either independently from each other or in combination with one another.
According to a preferred embodiment of the invention preference is also given to those phenyluracils of formula (I), wherein the variables, either independently of one another or in combination with one another, have the following meanings:
Preferred are the phenyuracils of formula (I) wherein
R1 is NH2 or Ci-Ce-alkyl; particularly preferred is CH3; also particularly preferred is NH2.
Also preferred are the phenyuracils of formula (I) wherein
R2 is Ci-C4-haloalkyl; particularly preferred is Ci-Cs-haloalkyl; more preferred is Ci-C2-haloalkyl; especially preferred is CF3.
Also preferred are the phenyuracils of formula (I) wherein
R3 is H or Ci-C4-alkyl; particularly preferred is H or CH3; more preferred is H; also more preferred is CH3.
Also preferred are the phenyuracils of formula (I) wherein
R4 is H, F or Cl; particularly preferred is H or F; especially preferred is F.
Also preferred are the phenyuracils of formula (I) wherein
R5 is halogen, Ci-Cs-haloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylthio or C1-C3- alkoxycarbonyl; preferably is Ci-Cs-alkoxy, Ci-Cs-haloalkoxy or Ci-Cs-alkylthio; particularly preferred is Ci-Cs-alkoxy or Ci-Cs-alkylthio; especially preferred is Ci-Cs-alkoxy; more preferred is OCH3.
Also preferred are the phenyuracils of formula (I) wherein
R6 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, Cs-Ce-haloalkenyl, Cs-Ce-haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxy-Ci-Ce- alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl; preferably is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, Ci-Ce- cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl; particularly preferred is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce- cyanoalkyl or Ci-Ce-alkoxy-Ci-Ce-alkyl; especially preferred is hydrogen, Ci-Ce-alkyl, or Cs-Ce-alkenyl; more preferred is hydrogen, CH3, C2H5 or CH2CH=CH2; most preferred is hydrogen, CH3 or C2H5.
Also preferred are the phenyuracils of formula (I) wherein
R6 is hydrogen or Ci-Ce-alkyl.
Also preferred are the phenyuracils of formula (I) wherein n is 1 or 2; particularly preferred is 2; also particularly preferred is 1 .
Also preferred are the phenyuracils of formula (I) wherein
Q is O, also preferably is S.
Also preferred are the phenyuracils of formula (I) wherein
W is O, also preferably is S.
Also preferred are the phenyuracils of formula (I) wherein
X is O, also preferably is S.
Also preferred are the phenyuracils of formula (I) wherein
Y is O, also preferably is S.
Also preferred are the phenyuracils of formula (I) wherein
Z is phenyl or pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is phenyl or pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3 or OCH3; especially preferred is phenyl or pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH3; more preferred is phenyl or pyridyl, each of which is unsubstituted.
Also preferred are the phenyuracils of formula (I) wherein
Z is phenyl or 2-pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is phenyl or 2-pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3 or OCH3; especially preferred is phenyl or 2-pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH3; more preferred is phenyl or 2-pyridyl, each of which is unsubstituted.
Also preferred are the phenyuracils of formula (I) wherein
Z is phenyl, which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is phenyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3 or OCH3; especially preferred is phenyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH3; also especially preferred is unsubstituted phenyl.
Also preferred are the phenyuracils of formula (I) wherein
Z is pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3 or OCH3; especially preferred is pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH3; also especially preferred is unsubstituted pyridyl.
Also preferred are the phenyuracils of formula (I) wherein
Z is 2-pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred is 2-pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3 or OCH3; especially preferred is 2-pyridyl, which is optionally substituted by 1 substituent selected from the group consisting of F, Cl or CH3; also especially preferred is unsubstituted 2-pyridyl.
Also preferred are phenyuracils of formula (I) wherein
Z is selected from the group consisting of Z1 to Z13
Figure imgf000013_0001
wherein
* denotes the point of attachment of Z to X;
** denotes the point of attachment of Z to Q; and Ra, Rb, Rc, Rd and Re independently of one another are
H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H.
Also preferred are phenyuracils of formula (I) wherein
Z is selected from the group consisting of Z1, Z2, Z4, Z5, Z6, Z7, Z8, Z9, Z10 and Z11 as defined above; particularly preferred is selected from the group consisting of Z1, Z4, Z5, Z6 and Z7 as defined above; more particularly preferred is selected from the group consisting of Z1, Z4, Z5, Z6 and Z7 as defined above; especially preferred is selected from the group consisting of Z1 and Z7 as defined above; more preferred is selected from Z1 as defined above; also more preferred is selected from Z7 as defined above.
Also preferred are phenyuracils of formula (I) wherein
Z is selected from the group consisting of Z1, Z2, Z4, Z5, Z6, Z7, Z8, Z9, Z10 and Z11 as defined above, wherein
Ra, Rb, Rc, Rd and Re independently of one another are
H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H; particularly preferred is selected from the group consisting of Z1, Z4, Z5, Z6 and Z7, as defined above, wherein
Ra, Rb, Rc, Rd and Re independently of one another are
H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H; especially preferred is selected from the group consisting of Z1 and Z7 as defined above, wherein
Ra, Rb, Rc, Rd and Re independently of one another are
H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H; more preferred is Z1 as defined above, wherein Ra, Rb, Rc, Rd and Re independently of one another are
H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H; also more preferred is Z7 as defined above, wherein
Ra, Rb, Rc, Rd and Re independently of one another are
H, halogen, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkoxy or Ci-Ce-haloalkoxy; preferably H, halogen, Ci-Ce-alkyl or Ci-Ce-alkoxy; particularly preferred H, F, Cl, Br, CH3 or OCH3; especially preferred H, F, Cl or CH3; more preferred H.
Also preferred are phenyluracils of formula (I) wherein
R1 is CH3;
R2 is Ci-Cs-haloalkyl;
R3 is hydrogen or CH3;
R4 is H or halogen;
R5 is Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylthio;
R6 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, C3-C6- haloalkenyl, Cs-Ce-haloalkynyl, Ci-Ce-cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce- alkoxy-Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, n is 1;
Q, W and Y are O;
X is O or S;
Z is phenyl or 2-pyridyl, each of which is optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3, OCH3.
Also preferred are phenyluracils of formula (I) wherein
R1 is CH3;
R2 is Ci-Cs-haloalkyl;
R3 is hydrogen;
R4 is F;
R5 is Ci-Cs-alkoxy;
R6 is hydrogen, Ci-Ce-alkyl, Cs-Ce-alkenyl, Cs-Ce-alkynyl, Ci-Ce-haloalkyl, Ci-Ce- cyanoalkyl, Ci-Ce-alkoxy-Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl-Ci-Ce-alkyl, n is 1;
Q, W, X and Y are O;
Z is phenyl, optionally substituted by 1 substituent selected from the group consisting of F, Cl, Br, CH3, OCH3. Particular preference is given to phenyluracils of formula (I. a) (corresponds to formula (I) wherein R1 is CH3, R2 is CF3, R3 is H, n is 1 , Q, W, X and Y are O, and Z is Z-1 as defined, wherein Ra, Rb, Rc and Rd are H:
Figure imgf000016_0001
wherein the variables R4, R5, and R6 have the meanings, in particular the preferred meanings, as defined above; special preference is given to phenyuracils of formulae (I .a.1) to (I. a.36) of Table A, where the definitions of the variables R4, R5, and R6 are of particular importance for the phenyluracils according to the invention not only in combination with one another but in each case also on their own:
Table A
Figure imgf000016_0002
Figure imgf000017_0004
Also preferred are phenyuracils of formula (l.b), preferably phenyuracils of formulae (l.b.1) to (l.b.36), which differ from the corresponding phenyuracils of formulae (l.a.1) to (I. a.36) only in that Q is S:
Figure imgf000017_0001
Also preferred are the phenyuracils of formula (l.e), preferably the phenyuracils of formulae (l.c.1) to (l.c.36), which differ from the corresponding phenyuracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-2, wherein Ra, Rb, Rc and Re are H:
Figure imgf000017_0002
Also preferred are the phenyuracils of formula (l.d), preferably the phenyuracils of formulae (l.d.1) to (l.d.36), which differ from the corresponding phenyuracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-3, wherein Ra, Rb, Rd and Re are H:
Figure imgf000017_0003
Also preferred are the phenyluracils of formula (l.e), preferably the phenyluracils of formulae (l.e.1) to (l.e.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.56) only in that Z is Z-4, wherein Rb, Rc and Rd are H:
Figure imgf000018_0001
Also preferred are the phenyluracils of formula (l.f), preferably the phenyluracils of formulae (l.f.1) to (l.f.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-5, wherein Ra, Rc and Rd are H:
Figure imgf000018_0002
Also preferred are the phenyluracils of formula (l.g), preferably the phenyluracils of formulae (l.g.1) to (l.g.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-6, wherein Ra, Rb and Rd are H:
Figure imgf000018_0003
Also preferred are the phenyluracils of formula (l.h), preferably the phenyluracils of formulae (l.h.1) to (l.h.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-7, wherein Ra, Rb and Rc are H:
Figure imgf000018_0004
Also preferred are the phenyluracils of formula (l.i), preferably the phenyluracils of formulae (l.i.1) to (l.i.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-7, wherein Ra, Rb and Rc are H, and Q is S:
Figure imgf000019_0001
Also preferred are the phenyluracils of formula (l.k), preferably the phenyluracils of formulae (l.k.1) to (l.k.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-8, wherein Rb, Rc and Re are H:
Figure imgf000019_0002
Also preferred are the phenyluracils of formula (I. I), preferably the phenyluracils of formulae (1.1.1) to (1.1.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-9, wherein Ra, Rc and Re are H:
Figure imgf000019_0003
Also preferred are the phenyluracils of formula (l.m), preferably the phenyluracils of formulae (l.m.1) to (l.m.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-10, wherein Ra, Rb and Re are H:
Figure imgf000019_0004
Also preferred are the phenyluracils of formula (l.n), preferably the phenyluracils of formulae (l.n.1) to (l.n.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-11 , wherein Ra, Rb and Rc are H:
Figure imgf000020_0001
Also preferred are the phenyluracils of formula (l.o), preferably the phenyluracils of formulae (l.o.1) to (I. o.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-12, wherein Rb, Rd and Re are H:
Figure imgf000020_0002
Also preferred are the phenyluracils of formula (l.p), preferably the phenyluracils of formulae (l.p.1) to (l.p.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that Z is Z-13, wherein Ra, Rd and Re are H:
Figure imgf000020_0003
Also preferred are the phenyluracils of formula (l.q) preferably the phenyluracils of formulae (l.q.1) to (l.q.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only that R5 is SCH3:
Figure imgf000020_0004
Also preferred are the phenyluracils of formula (l.r), preferably the phenyluracils of formulae (l.r.1) to (l.r.36), which differ from the corresponding phenyluracils of formulae (l.a.1) to (I. a.36) only in that R3 is CH3:
Figure imgf000021_0001
According to another preferred embodiment of the invention the composition contains as component A at least one phenyluracil selected from formulae (I. a), (l.h), (l.q), and (l.r).
According to another preferred embodiment of the invention the composition contains as component A at least one phenyluracil of formula (I. a).
According to another preferred embodiment of the invention the composition contains as component A at least one phenyluracil of formula (l.h).
According to another preferred embodiment of the invention the composition contains as component A at least one phenyluracil selected from formulae (l.a.1) to (1.a.36), (l.h.1) to (l.h.36), (l.q.1) to (l.q.36) and (l.r.1) to (l.r.36); particularly preferred at least one phenyluracil selected from formulae (l.a.1) to (1.a.36).
According to another preferred embodiment of the invention the composition contains as component A at least one phenyluracil selected from formulae (I. a.19), (I. a.20), (I. a.21), (I. a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20); particularly preferred at least one phenyluracil selected from formulae (I. a.19), (I. a.20), (I. a.21), (l.a.25), (l.a.26), (l.a.27) and (l.a.31); also particularly preferred at least one phenyluracil selected from formulae (I. a.20), (l.h.20), (l.q.20) and (l.r.20).
According to a particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (l.a.19).
According to a particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (I. a.20).
According to a particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (I. a.21).
According to a particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (l.a.25).
According to a particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (l.a.26). According to a particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (I. a.27).
According to a particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (I. a.31).
According to a further particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (l.h.20).
According to a further particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (l.q.20).
According to a further particular preferred embodiment of the invention the composition contains as component A the phenyluracil of formula (l.r.20).
As component A, especially preferred phenyluracils of formula (I) are methyl rac-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; methyl (2S)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; methyl (2R)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; rac-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetic acid;
(2S)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetic acid;
(2R)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetic acid; ethyl rac-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; ethyl (2S)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; ethyl (2R)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; allyl rac-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; allyl (2S)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; allyl (2R)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; prop-2-ynyl rac-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; prop-2-ynyl (2S)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; prop-2-ynyl (2R)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; cyanomethyl rac-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; cyanomethyl (2S)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; cyanomethyl (2R)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate;
2-methoxyethyl rac-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate;
2-methoxyethyl (2S)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate;
2-methoxyethyl (2R)-2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate; methyl rac-2-[2-[2-bromo-5-[3,5-dimethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-4-fluoro- phenoxy]phenoxy]-2-methoxy-acetate; methyl (2S)-2-[2-[2-bromo-5-[3,5-dimethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-4-fluoro- phenoxy]phenoxy]-2-methoxy-acetate; methyl (2R)-2-[2-[2-bromo-5-[3,5-dimethyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-4-fluoro- phenoxy]phenoxy]-2-methoxy-acetate; methyl rac-2-[[3-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]-2-pyridyl]oxy]-2-methoxy-acetate; methyl (2S)-2-[[3-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]-2-pyridyl]oxy]-2-methoxy-acetate; methyl (2R)-2-[[3-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]-2-pyridyl]oxy]-2-methoxy-acetate.
The phenyluracils of formula (I) can be prepared by reaction of compounds of formula (II) with alkylating agents of formula (III) in the presence of a base in analogy to known processes (e.g.
Figure imgf000023_0001
Within the alkylating agents of formula (III), L1 is a leaving group such as halogen.
The alkylating agents of formula (III) are commercially available or can be prepared by known methods (e.g. WO 11/137088).
Compounds of formula (II) can be prepared by deprotection of the respective compounds of formula (VI):
Figure imgf000024_0001
Within the compounds of formula (VI) “PG” is a protecting group selected from the group consisting of Ci-Ce-alkyl or (tri-Ci-C6-alkyl)silyl-Ci-C4-alkyl.
For example, the compounds of formula (II) can be prepared by treating the compounds of formula (VI), wherein “PG” is methyl, with boron tribromide in a solvent such as dichloromethane at temperatures ranging from 0 °C to 150 °C.
Compounds of formula (VI), wherein R1 is H, can be prepared by reaction of amines of formula
(VII) with oxazinones of formula
Figure imgf000024_0002
Figure imgf000024_0003
Figure imgf000024_0004
The reaction may in principle be carried out in substance. However, preference is given to reacting the amines of formula (VII) with the oxazinones of formula (VIII) in an organic solvent. Suitable in principle are all solvents which can dissolve the amines of formula (VII) and the oxazinones of formula (VIII) at least partly, and preferably fully under reaction conditions.
Examples of suitable solvents are halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone, tert-butyl methyl ketone, cyclohexanone; organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N- dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), N,N'-dimethylpropylene urea (DMPLI), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP). It is also possible to use mixtures of the solvents mentioned.
As acids inorganic acids like hydrochloric acid, hydrobromic acid or sulfuric acid, as well as organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid, can be used.
The acids are generally employed in equimolar amounts, in excess or, if appropriate, be used as solvent, however they can also be employed in catalytic amounts.
Those compounds of formula (VI), wherein R1 is NH2, Ci-Ce-alkyl or Cs-Ce-alkynyl, can be prepared by amination or alkylation of those compounds of formula (VI), wherein R1 is H. Such amination or alkylation can be conducted in analogy to known processes (e.g. WO 05/054208; WO 06/125746).
As alkylation reagents commercially available Ci-Ce-alkylhalides and alkinylhalides can be used.
Suitable amination reagents are known from literature (e.g. US 6333296 or DE 10005284)
The compounds of formula (VIII) required for the preparation of compounds of formula (VI) are commercially available or can be prepared by known methods.
The amines of formula (VII) required for the preparation of compounds of formula (VI) can be prepared from the corresponding compound of formula (IX):
Figure imgf000025_0001
Within the compound of formula (IX) the group “PG” is a protecting group as defined above for the compounds of formula (VI).
The reaction may in principle be carried out in substance. However, preference is given to reacting the amines of formula (VII) with the oxazinones of formula (VIII) in an organic solvent. Suitable in principle are all solvents which are capable of dissolving the amines of formula (VII) and the oxazinones of formula (VIII) at least partly, and preferably fully under reaction conditions.
Examples of suitable solvents are halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF); nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone, tert-butyl methyl ketone, cyclohexanone; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert.-butanol, organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), N,N '-dimethylpropylene urea (DMPLI), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP).
As acids inorganic acids like hydrochloric acid, hydrobromic acid or sulfuric acid, as well as organic acids like formic acid, acetic acid, propionic acid, oxalic acid, methylbenzenesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, citric acid, trifluoroacetic acid, can be used.
The acids are generally employed in equimolar amounts, in excess or, if appropriate, be used as solvent, however they can also be employed in catalytic amounts.
The compounds of formula (IX) required for the preparation of compounds of formula (VII) can be prepared from the corresponding nitro compounds of formula (X):
Figure imgf000026_0001
The compound of formula (IX) can be prepared by reduction followed by a Sandmeyer reaction from a compound of formula (X).
Reduction of the nitro group of compounds of formula (X) can be carried out by catalytic hydrogenation in hydrogen gas at a pressure of 70 to 700 kPa, preferably 270 to 350 kPa, in the presence of a metal catalyst such as palladium supported on an inert carrier such as activated carbon, in a weight ratio of 5 to 20% of metal to carrier, suspended in a solvent such as ethanol at ambient temperature.
Bromination of the resulting amine is facilitated by diazotization with an alkyl nitrite ( e.g. isoamyl nitrite) followed by treatment with a copper (I) bromide and/or copper (II) bromide in a solvent such as acetonitrile at a temperature ranging from 0 °C to the reflux temperature of the solvent to give the corresponding compound of formula (IX).
The compounds of formula (X) required for the preparation of compounds of formula (IX) can be prepared by reaction of compounds of formula (XI) with compounds of formula (XII) in the presence of a base:
Figure imgf000026_0002
Within the compounds of formula (XI) L3 is a leaving group such as halogen.
The reaction is carried out in an organic solvent.
Examples of suitable solvents are halogenated hydrocarbons such as dichloromethane, 1 ,2- dichloroethane, chloroform, carbon tetrachloride and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and tetrahydrofuran (THF), nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, N,N-dimethylformamide (DMF), N,N-dimethylacetamide (DMAC), 1,3-dimethyl-2-imidazolidinone (DMI), N,N '-dimethylpropylene urea (DMPLI), dimethyl sulfoxide (DMSO) and 1-methyl-2 pyrrolidinone (NMP).
It is also possible to use mixtures of the solvents mentioned.
Examples of suitable bases include metal-containing bases and nitrogen-containing bases. Examples of suitable metal-containing bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide; alkali metal and alkaline earth metal oxide, and other metal oxides, such as lithium oxide, sodium oxide, potassium oxide, magnesium oxide, calcium oxide and magnesium oxide, iron oxide, silver oxide; alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, magnesium carbonate, and calcium carbonate, as well as alkali metal hydrogen carbonates (bicarbonates) such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate; alkali metal and alkaline earth metal phosphates such as potassium phosphate, calcium phosphate; metal organic compounds, preferably alkali metal alkyls such as methyl lithium, butyl lithium and phenyl lithium, alkyl magnesium halides such as methyl magnesium chloride as well as alkali metal and alkaline earth metal alkoxides such as potassium tert-butoxide, potassium tertpentoxide; and furthermore organic bases, such as tertiary amines such as trimethylamine, triethylamine, diisopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidinge, lutidine, N-methylmorpholine and 4-dimethylaminopyridine and also bicyclic amines.
The bases are generally employed in equimolar amounts or in excess; however they can also be employed as solvent, or, if appropriate, in catalytic amounts.
The compounds of formula (XII) required for the preparation of compounds of formula (X) are commercially available or can be prepared by known methods.
The compounds of formula (XI) required for the preparation of compounds of formula (X) can be prepared from compounds of formula (XIII):
Figure imgf000027_0001
The reaction can be carried out by adding bis(1 , 1 -dimethylethyl) dicarbonate (CAS 24424-99-5) to compounds of formula (XIII) in an organic solvent. The addition of a base can be advantages.
Examples of suitable solvents are halogenated hydrocarbons such as dichloromethane, 1,2- dichloroethane, chloroform. Examples of suitable bases are nitrogen-containing bases such as 4-(dimethylamino)pyridine (DMAP), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or 1 ,5-diazabicyclo[4.3.0]non-5-ene (DBN).
The compounds of formula (XIII) required for the preparation of compounds of formula (XI) are commercially available or can be prepared by known methods.
In one embodiment of the present invention the compositions according to the present invention comprise at least one phenyluracil of formula (I) and at least one further active compound B (herbicide B).
According to a first embodiment of the invention the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1). These are compounds that inhibit lipid biosynthesis. Inhibition of the lipid biosynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter termed ACC herbicides) or through a different mode of action (hereinafter termed non-ACC herbicides). The ACC herbicides belong to the group A of the HRAC classification system whereas the non-ACC herbicides belong to the group N of the HRAC classification.
According to a second embodiment of the invention the compositions contain at least one ALS inhibitor (herbicide b2). The herbicidal activity of these compounds is based on the inhibition of acetolactate synthase and thus on the inhibition of the branched chain amino acid biosynthesis. These inhibitors belong to the group B of the HRAC classification system.
According to a third embodiment of the invention the compositions contain at least one inhibitor of photosynthesis (herbicide b3). The herbicidal activity of these compounds is based either on the inhibition of the photosystem II in plants (so-called PSII inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis. Amongst these, PSII inhibitors are preferred.
According to a fourth embodiment of the invention the compositions contain at least one inhibitor of protoporphyrinogen-IX-oxidase (herbicide b4). The herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase. These inhibitors belong to the group E of the HRAC classification system.
According to a fifth embodiment of the invention the compositions contain at least one bleacher-herbicide (herbicide b5). The herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis. These include compounds which inhibit carotenoid biosynthesis by inhibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).
According to a sixth embodiment of the invention the compositions contain at least one EPSP synthase inhibitor (herbicide b6). The herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid biosynthesis in plants. These inhibitors belong to the group G of the HRAC classification system.
According to a seventh embodiment of the invention the compositions contain at least one glutamine synthetase inhibitor (herbicide b7). The herbicidal activity of these compounds is based on the inhibition of glutamine synthetase, and thus on the inhibition of the aminoacid biosynthesis in plants. These inhibitors belong to the group H of the HRAC classification system.
According to an eighth embodiment of the invention the compositions contain at least one DHP synthase inhibitor (herbicide b8). The herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase. These inhibitors belong to the group I of the HRAC classification system.
According to a ninth embodiment of the invention the compositions contain at least one mitosis inhibitor (herbicide b9). The herbicidal activity of these compounds is based on the disturbance or inhibition of microtubule formation or organization, and thus on the inhibition of mitosis. These inhibitors belong to the groups K1 and K2 of the HRAC classification system. Among these, compounds of the group K1 , in particular dinitroanilines, are preferred.
According to a tenth embodiment of the invention the compositions contain at least one VLCFA inhibitor (herbicide b10). The herbicidal activity of these compounds is based on the inhibition of the synthesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants. These inhibitors belong to the group K3 of the HRAC classification system.
According to an eleventh embodiment of the invention the compositions contain at least one cellulose biosynthesis inhibitor (herbicide b11). The herbicidal activity of these compounds is based on the inhibition of the biosynthesis of cellulose and thus on the inhibition of the synthesis of cell walls in plants. These inhibitors belong to the group L of the HRAC classification system.
According to a twelfth embodiment of the invention the compositions contain at least one decoupler herbicide (herbicide b12). The herbicidal activity of these compounds is based on the disruption of the cell membrane. These inhibitors belong to the group M of the HRAC classification system.
According to a thirtheenth embodiment of the invention the compositions contain at least one auxinic herbicide (herbicide b13). These include compounds that mimic auxins, i.e. plant hormones, and affect the growth of the plants. These compounds belong to the group O of the HRAC classification system.
According to a fourteenth embodiment of the invention the compositions contain at least one auxin transport inhibitor (herbicide b14). The herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants. These compounds belong to the group P of the HRAC classification system.
As to the given mechanisms of action and classification of the active substances, see e.g. "HRAC, Classification of Herbicides According to Mode of Action", http://www.plantprotection.org/hrac/MOA.html).
Preference is given to those compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b4, b5, b6, b7, b9, b10 and b13.
Specific preference is given to those compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b2, b4, b6, b7, b10 and b13.
Particular preference is given to those compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b4, b6, b7and b10. Examples of herbicides B which can be used in combination with the phenyluracils of formula (I) according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors:
ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop- tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2, 2,6,6- tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1,1'- biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'- Chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran- 3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1'- biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5- (Acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 ,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl- 2H-pyran-3-one; 5-(Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro- 2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4- ethyl[1 ,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1 ,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo- 2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1,1'- biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate; b2) from the group of the ALS inhibitors: sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron, imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam, pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methylethyl ester (CAS 420138-41-6), 4- [[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01-8), sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone; among these, a preferred embodiment of the invention relates to those compositions comprising at least one imidazolinone herbicide; b3) from the group of the photosynthesis inhibitors: amicarbazone, inhibitors of the photosystem II, e.g. 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1-methyl- pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1- methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4- hydroxy-1 ,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5- ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69- 4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1), triazine herbicides, including of chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn.hexazinone, metribuzin, prometon, prometryn, propazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea such as chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthiuron and thiadiazuron, phenyl carbamates such as desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles such as bromacil, lenacil and terbacil, and bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and inhibitors of the photosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate. Among these, a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide; b4) from the group of the protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, cyclopyranil, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, epyrifenacil, N-ethyl-3-(2,6- dichloro-4-trifluoromethylphenoxy)-5-methyl-1/7-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1/7-pyrazole-1- carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5- methyl-1/7-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6- fluoro-4-trifluoromethylphenoxy)-5-methyl-1/7-pyrazole-1-carboxamide (CAS 452100-03-7), 3- [7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo- [1, 3, 5]triazinan-2, 4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4- dihydro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 1300118-96-0),
1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H- benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2, 4-dione (CAS 1304113-05-0), methyl (E)-4-[2-chloro-5- [4-chloro-5-(difluoromethoxy)-1/7-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2- enoate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-
1-methyl-6-(trifluoromethyl)-1 H-pyrimidine-2, 4-dione (CAS 212754-02-4), 2-[2-chloro-5-[3- chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS 1970221-16-9), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- 1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274- 96-3), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5- fluoro-2-pyridinyl]oxy]phenoxy] acetic acid ethyl ester (CAS 158274-50-9), methyl 2-[[3-[2- chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2- pyridyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5- oxo-1 ,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), 2-[[3-[[3- chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2- pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9), 2-[[3-[[3-chloro-6- [3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-
2-pyridinyl]oxy] acetic acid ethyl ester (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3- methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N- (methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6- dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N- (methylsulfonyl)-acetamide (CAS 2158276-22-1), 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6- dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5- isoxazolecarboxylic acid ethyl ester (CAS 1949837-17-5), methyl (1S,4R)-4-[[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-1 ,2-oxazol-5-yl]carbonyl]amino]- cyclopent-2-en-1-carboxylat (CAS 2365468-20-6), ethyl (1S,4R)-4-[[[3-(3,5-difluorphenyl)-5- methoxy-4H-1 ,2-oxazol-5-yl]carbonyl]amino]-cyclopent-2-en-1-carboxylat (CAS 2365468-27- 3), methyl (4S)-4-[[[3-(3,5-difluorphenyl)-5-methyl-4H-1 ,2-oxazol-5-yl]carbonyl]amino]- cyclopenten-1-carboxylat (CAS 2365470-33-1), methyl (3S)-3-[[[(5R)-3-(3,5-difluorphenyl)-5- methyl-4H-1 ,2-oxazol-5-yl]carbonyl]amino]-cyclopenten-1-carboxylat (CAS 2365470-65-9), (1S,4R)-4-[[[(5R)-3-(3,5-difluorphenyl)-5-methyl-4H-1 ,2-isoxazole-5-carbonyl]amino]- cyclopent-2-ene-1 -carboxylic acid (CAS 2574325-00-9), methyl rel-(2R,4R)-4-[[3-(3,5- dichlorophenyl)-5-methoxy-4H-isoxazole-5-carbonyl]amino]tetra-hydrofuran-2-carboxylate (CAS 2254813-45-9), methyl rel-(2R,4R)-4-[[3-(3,5-dichlorophenyl)-5-vinyl-4H-isoxazole-5- carbonyl]amino]tetrahydro-furan-2-carboxylate (CAS 2254813-46-0), methyl rel-(2R,4R)-4- [[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]-tetrahydrofuran-2- carboxylate (CAS 2254752-21-9), isopropyl rel-(2R,4R)-4-[[3-(3-fluorophenyl)-5-methyl-4H- isoxazole-5-carbonyl]amino]tetra-hydrofuran-2-carboxylate (CAS 2254813-65-3), methyl (3R)-
3-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]-2,3-dihydrofuran-5- carboxylate (CAS 2439157-64-7), methyl (3R)-3-[[(5R)-3-(3,5-difluorophenyl)-5-methyl-4H- isoxazole-5-carbonyl]amino]-2,3-dihydrofuran-5-carboxylate (CAS 2439157-65-8), (5S)-3-(3,5- difluorophenyl)-N-[rel-(3R,5R)-5-(trifluoromethylsulfonyl-carbamoyl)tetrahydrofuran-3-yl]-5- vinyl-4H-isoxazole-5-carboxamid, (5R)-3-(3,5-difluoro-phenyl)-5-methyl-N-[rel-(3R,5R)-5- (methylsulfonylcarbamoyl)tetrahydrofuran-3-yl]-4H-isoxazole-5-carboxamid, (5S)-3-(3-fluoro-5- methyl-phenyl)-N-[rel-(3R,5R)-5-(methoxy-carbamoyl)tetrahydrofuran-3-yl]-5-vinyl-4H- isoxazole-5-carboxamid, (5S)-3-(3,5-difluoro-phenyl)-N-[(3R)-5-(methylsulfonylcarbamoyl)-2,3- dihydrofuran-3-yl]-5-vinyl-4H-isoxazole-5-carboxamid, (5R)-3-(3,5-difluorophenyl)-N-[(3R)-5- (methoxycarbamoyl)-2,3-dihydrofuran-3-yl]-5-methyl-4H-isoxazole-5-carboxamid; b5) from the group of the bleacher herbicides:
PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33- 7) and rimisoxafen, HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, bipyrazone, fenpyrazone, cypyrafluone, tripyrasulfone, benquitrione, dioxopyritrione; bleacher, unknown target: aclonifen, amitrole flumeturon 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5- yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone and 2-(2,5- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7); b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate-potassium and glyphosate-trimesium (sulfosate); b7) from the group of the glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P and glufosinate- ammonium; b8) from the group of the DHP synthase inhibitors: asulam; b9) from the group of the mitosis inhibitors: compounds of group K1: dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as amiprophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop- isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, compounds of group K1 , in particular dinitroanilines are preferred; b10) from the group of the VLCFA inhibitors: chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, dimesulfazet and isoxazoline compounds of the formulae 11.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
Figure imgf000034_0001
the isoxazoline compounds of the formula (II) are known in the art, e.g. from WO 2006/024820, WO 2006/037945, WO 2007/071900 and WO 2007/096576; among the VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b11) from the group of the cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5- pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1); b12) from the group of the decoupler herbicides: dinoseb, dinoterb and DNOC and its salts; b13) from the group of the auxinic herbicides:
2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72- 9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6); b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium; b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl- dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine tetflupyrolimet, tridiphane, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2- methyl-pyridazin-3-one (CAS 2414510-21-5).
Preferred herbicides B that can be used in combination with the phenyluracils of the formula (I) according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors: clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P- ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-4- cyclopropyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1'-biphenyl]-3-yl)-5-hydroxy-2, 2,6,6- tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1'- biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'- Dichloro-4-ethyl[1 ,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'- dichloro-4-cyclopropyl- [1 , 1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5- (Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H- pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1'-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'- fluoro[1 , 1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1 , 1 '-biphenyl]-3-yl)-5,6- dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4- ethyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1'-biphenyl]-3-yl)-5,6-dihydro- 2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, dimepiperate, EPTC, esprocarb, ethofumesate, molinate, orbencarb, prosulfocarb, thiobencarb and triallate; b2) from the group of the ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlorsulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metosulam, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazon-sodium, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, pyrimisulfan, pyriftalid, pyriminobac-methyl, pyrithiobac- sodium, pyroxsulam, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron and triafamone; b3) from the group of the photosynthesis inhibitors: ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromoxynil and its salts and esters, chloridazone, chlorotoluron, cyanazine, desmedipham, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, lenacil, linuron, metamitron, methabenzthiazuron, metribuzin, paraquat, paraquat-dichloride, phenmedipham, propanil, pyridate, simazine, terbutryn, terbuthylazine, thidiazuron, 1-(6-tert-butylpyrimidin-4-yl)-
2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3- yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-
3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1- methyl-pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5- tert-butyl-1-methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747- 80-4), 4-hydroxy-1 -methoxy- 5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hydroxy-1 ,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1 ,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3- yl]imidazolidin-2-one (CAS 2023785-80-8) and 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-
3-methyl-imidazolidin-2-one (CAS 1844836-64-1); b4) from the group of the protoporphyrinogen-IX oxidase inhibitors: acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon- ethyl, cyclopyranil, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen- ethyl, saflufenacil, sulfentrazone, tiafenacil, trifludimoxazin, epyrifenacil, N-ethyl-3-(2,6-dichloro-
4-trifluoromethylphenoxy)-5-methyl-1/7-pyrazole-1-carboxamide (CAS 452098-92-9), N- tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1/7-pyrazole-1- carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5- methyl-1/7-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6- fluoro-4-trifluoromethylphenoxy)-5-methyl-1/7-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7- fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-
[1 , 3, 5]triazinan-2, 4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro- 2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 1300118-96-0); 1- methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin- 6-yl)-1 H-pyrimidine-2, 4-dione (CAS 1304113-05-0), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)- 1 H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimidine-2, 4-dione (CAS 212754-02-4); 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS 1970221-16-9), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-l (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)- pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy] acetic acid ethyl ester (CAS 158274-50-9), methyl
2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1 ,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2- pyridyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5- oxo-1 ,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), 2-[[3-[[3- chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2- pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS 2158275-73-9), 2-[[3-[[3-chloro-6- [3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2- pyridinyl]oxy] acetic acid ethyl ester (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3- methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N- (methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6- dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N- (methylsulfonyl)-acetamide (CAS 2158276-22-1), 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo- 4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylic acid ethyl ester (CAS 1949837-17-5), methyl (1S,4R)-4-[[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-1 ,2-oxazol-5-yl]carbonyl]amino]- cyclopent-2-en-1-carboxylat (CAS 2365468-20-6), ethyl (1S,4R)-4-[[[3-(3,5-difluorphenyl)-5- methoxy-4H-1 ,2-oxazol-5-yl]carbonyl]amino]-cyclopent-2-en-1-carboxylat (CAS 2365468-27-3), methyl (4S)-4-[[[3-(3,5-difluorphenyl)-5-methyl-4H-1 ,2-oxazol-5-yl]carbonyl]amino]-cyclopenten- 1-carboxylat (CAS 2365470-33-1), methyl (3S)-3-[[[(5R)-3-(3,5-difluorphenyl)-5-methyl-4H-1 ,2- oxazol-5-yl]carbonyl]amino]-cyclopenten-1-carboxylat (CAS 2365470-65-9), (1S,4R)-4-[[[(5R)-3- (3, 5-difluorphenyl)-5-methyl-4H-1 ,2-isoxazole-5-carbonyl]amino]-cyclopent-2-ene-1 -carboxylic acid (CAS 2574325-00-9), methyl rel-(2R,4R)-4-[[3-(3,5-dichlorophenyl)-5-methoxy-4H- isoxazole-5-carbonyl]amino]tetra-hydrofuran-2-carboxylate (CAS 2254813-45-9), methyl rel- (2R,4R)-4-[[3-(3,5-dichlorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetra-hydrofuran-2- carboxylate (CAS 2254813-46-0), methyl rel-(2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H- isoxazole-5-carbonyl]amino]tetra-hydrofuran-2-carboxylate (CAS 2254752-21-9), isopropyl rel- (2R,4R)-4-[[3-(3 -fluorophenyl)-5-methyl-4H-isoxazole-5-carbonyl]amino]tetra-hydrofuran-2- carboxylate (CAS 2254813-65-3), methyl (3R)-3-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H- isoxazole-5-carbonyl]amino]-2,3-dihydro-furan-5-carboxylate (CAS 2439157-64-7), methyl (3R)-
3-[[(5R)-3-(3,5-difluorophenyl)-5-methyl-4H-isoxazole-5-carbonyl]amino]-2,3-dihydrofuran-5- carboxylate (CAS 2439157-65-8); b5) from the group of the bleacher herbicides: aclonifen, amitrole, beflubutamid, benzobicyclon, bicyclopyrone, clomazone, cypyrafluone, diflufenican, fenquinotrione, flumeturon, flurochloridone, flurtamone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), norflurazon, picolinafen, pyrasulfotole, pyrazolynate, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, 4-(3-trifluoromethylphenoxy)-2- (4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), 2-chloro-3-methylsulfanyl-N-(1- methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone, 2-(2,5- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7), rimisoxafen, and dioxopyritrione; b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate); b7) from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P, glufosinate-ammonium; b8) from the group of the DHP synthase inhibitors: asulam; b9) from the group of the mitosis inhibitors: benfluralin, dithiopyr, ethalfluralin, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M- isopropyl, flamprop-M-methyl, oryzalin, pendimethalin, thiazopyr and trifluralin; b10) from the group of the VLCFA inhibitors: acetochlor, alachlor, amidochlor, anilofos, butachlor, cafenstrole, dimethenamid, dimethenamid- P, dimesulfazet, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor and isoxazoline-compounds of the formulae 11.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above; b11) from the group of the cellulose biosynthesis inhibitors: dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01-1); b13) from the group of the auxinic herbicides:
2,4-D and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2- hydroxypropyl)ammonium and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6); b14) from the group of the auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium; b15) from the group of the other herbicides: bromobutide, cinmethylin, cumyluron, cyclopyrimorate and its salts and esters, dalapon, difenzoquat, difenzoquat-metilsulfate, DSMA, dymron (= daimuron), indanofan, metam, methylbromide, MSMA, oxaziclomefone, pyributicarb, tetflupyrolimet, tridiphane, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3- one (CAS 2414510-21-5).
Particularly preferred herbicides B that can be used in combination with the phenyluracils of the formula (I) according to the present invention are: b1) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'- Chloro-4-cyclopropyl-2'-fluoro[1 , 1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran- 3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1'-biphenyl]-3-yl)-5-hydroxy- 2.2.6.6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1'- biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'- Dichloro-4-ethyl[1 ,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'- dichloro-4-cyclopropyl- [1 , 1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5- (Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H- pyran-3-one (CAS 1312340-82-1); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1'-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'- fluoro[1 , 1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1); 4-(2',4'-Dichloro -4-cyclopropyl- [1 , 1 '-biphenyl]-3-yl)-5,6- dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4- ethyl-2'-fluoro[1 ,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1'-biphenyl]-3-yl)-5,6-dihydro-
2.2.6.6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); esprocarb, prosulfocarb, thiobencarb and triallate; b2) from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamuron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsulam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon-methyl, tritosulfuron and triafamone; b3) from the group of the photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn, terbuthylazine, 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2- one (CAS 1844836-64-1); b4) from the group of the protoporphyrinogen-IX oxidase inhibitors: cyclopyranil, flumioxazin, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, epyrifenacil, 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo- [1 , 3, 5]triazinan-2, 4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro- 2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 1300118-96-0), and 1- methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin- 6-yl)-1 H-pyrimidine-2, 4-dione (CAS 1304113-05-0); 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2- pyridinyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS 1970221-16-9), 2-[2-[[3- chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1 (2H)-pyrimidinyl]-5-fluoro-2- pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3), 2-[2-[[3-chloro-6-[3,6- dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2- pyridinyl]oxy]phenoxy] acetic acid ethyl ester (CAS 158274-50-9), methyl 2-[[3-[2-chloro-5-[4- (difluoromethyl)-3-methyl-5-oxo-1 ,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2271389-22-9), ethyl 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1 ,2,4-triazol-1-yl]-4- fluoro-phenoxy]-2-pyridyl]oxy]acetate (CAS 2230679-62-4), 2-[[3-[[3-chloro-6-[3,6-dihydro-3- methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]- acetic acid methyl ester (CAS 2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-
4-(trifluoromethyl)-1 (2 H)-py ri m idi ny l]-5-f I uoro-2-py ridi ny l]oxy]-2- py ri di ny l]oxy] acetic acid ethyl ester (CAS 2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)- 1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS 2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS 2158276-22-1), 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)- pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylic acid ethyl ester (CAS 1949837-17-5), methyl (1S,4R)-4-[[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-1 ,2-oxazol-5-yl]carbonyl]amino]- cyclopent-2-en-1-carboxylat (CAS 2365468-20-6), methyl rel-(2R,4R)-4-[[3-(3,5-dichlorophenyl)-
5-methoxy-4Hisoxazole-5-carbonyl]amino]tetra-hydrofuran-2-carboxylate (CAS 2254813-45-9), methyl rel-(2R,4R)-4-[[3-(3,5-dichlorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetra- hydrofuran-2-carboxylate (CAS 2254813-46-0), methyl rel-(2R,4R)-4-[[(5S)-3-(3,5- difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetra-hydrofuran-2-carboxylate (CAS 2254752-21-9); b5) from the group of the bleacher herbicides: amitrole, bicyclopyrone, clomazone, diflufenican, fenquinotrione, flumeturon, flurochloridone, isoxaflutole, mesotrione, oxotrione (CAS 1486617- 21-3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, 2-chloro-3- methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone, 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7), and rimisoxafen; b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate- isopropylammonium and glyphosate-trimesium (sulfosate); b7) from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium; b9) from the group of the mitosis inhibitors: pendimethalin and trifluralin; b10) from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone; likewise, preference is given to isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above; b11) from the group of the cellulose biosynthesis inhibitors: indaziflam, isoxaben and triaziflam; b13) from the group of the auxinic herbicides: 2,4-D and its salts and esters such as clacyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluroxypyr- meptyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen- benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6); b14) from the group of the auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium, b15) from the group of the other herbicides: cinmethylin, dymon (= daimuron), indanofan, oxaziclomefone, tetflupyrolimet, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl- pyridazin-3-one (CAS 2414510-21-5).
Particularly preferred herbicides B are the herbicides B as defined above; in particular the herbicides B.1 - B.215 listed below in table B:
Table B:
Figure imgf000041_0001
Figure imgf000041_0002
Figure imgf000042_0001
Figure imgf000042_0002
Figure imgf000043_0001
Figure imgf000043_0002
Figure imgf000044_0001
Figure imgf000044_0002
In another embodiment of the present invention the compositions according to the present invention comprise at least one phenyluracil of formula (I) and at least one safener C.
Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the present compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or postemergence application of the useful plant. The safeners and the phenyluracils of formula (I) and/or the herbicides B can be applied simultaneously or in succession.
Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1-phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro- 5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.
Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3- oxazolidine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).
Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526- 07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphtalic anhydride, 4- (dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3- (dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31-4) and metcamifen.
Particularly preferred safeners C, which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1 - C.17 listed below in table C:
Table C
Figure imgf000045_0001
Figure imgf000046_0001
The active compounds B of groups b1) to b15) and the active compounds C are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1 ,3- oxazolidine [CAS No. 52836-31-4] is also referred to as R-29148. 4-(Dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane [CAS No. 71526-07-3] is also referred to as AD-67 and MON 4660.
The assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this substance was only assigned to one mechanism of action.
Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative in the compositions according to the invention.
In the case of dicamba, suitable salts include those, where the counterion is an agriculturally acceptable cation. For example, suitable salts of dicamba are dicamba-sodium, dicamba- potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba- isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba- trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of a suitable ester are dicamba-methyl and dicamba-butotyl.
Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D- diethylammonium, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isopropylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D- dodecylammonium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2- hydroxypropyl)ammonium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4- D-sodium and 2,4-D-N,N,N-trimethylethanolammonium (2,4-D choline). Examples of suitable esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D-butyl, 2,4- D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-meptyl, 2,4-D- methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos. Suitable salts of 2,4-DB are for example 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB- dimethylammonium. Suitable esters of 2,4-DB are for example 2,4-DB-butyl and 2,4-DB-isoctyl. Suitable salts of dichlorprop are for example dichlorprop-sodium, dichlorprop-potassium and dichlorprop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop- butotyl and dichlorprop-isoctyl.
Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethyl- ammonium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA- isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA- olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB is MCPB-ethyl.
Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyral id-tris-(2- hydroxypropyl)ammonium. Example of suitable esters of clopyralid is clopyralid-methyl. Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.
Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isoctyl.
A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are for example triclopyr-ethyl and triclopyr-butotyl.
Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA- potassium and 2,3,6-TBA-sodium.
Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid- dimethylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
Suitable salts of glyphosate are for example glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate- trimesium (sulfosate).
A suitable salt of glufosinate is for example glufosinate-ammonium.
A suitable salt of glufosinate-P is for example glufosinate-P-ammonium.
Suitable salts and esters of bromoxynil are for example bromoxynil-butyrate, bromoxynil- heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
Suitable salts and esters of ioxonil are for example ioxonil-octanoate, ioxonil-potassium and ioxonil-sodium.
Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop- methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
Suitable salts of mecoprop-P are for example mecoprop-P-butotyl, mecoprop-P- dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-sodium.
A suitable salt of diflufenzopyr is for example diflufenzopyr-sodium.
A suitable salt of naptalam is for example naptalam-sodium.
Suitable salts and esters of aminocyclopyrachlor are for example aminocyclopyrachlor- dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor- triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium. A suitable salt of quinclorac is for example quinclorac-dimethylammonium.
A suitable salt of quinmerac is for example quinmerac-dimethylammonium.
A suitable salt of imazamox is for example imazamox-ammonium.
Suitable salts of imazapic are for example imazapic-ammonium and imazapic- isopropylammonium.
Suitable salts of imazapyr are for example imazapyr-ammonium and imazapyr- isopropylammonium.
A suitable salt of imazaquin is for example imazaquin-ammonium.
Suitable salts of imazethapyr are for example imazethapyr-ammonium and imazethapyr- isopropylammonium.
A suitable salt of topramezone is for example topramezone-sodium.
According to a preferred embodiment of the invention, the composition comprises as herbicidal active compound B or component B at least one, preferably exactly one herbicide B.
According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least two, preferably exactly two herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least three, preferably exactly three herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as safening component C or component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component B at least one, preferably exactly one herbicide B, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises at least two, preferably exactly two, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises at least three, preferably exactly three, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), and as component B at least one, preferably exactly one, herbicide B.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), and at least two, preferably exactly two, herbicides B different from each other. According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), and at least three, preferably exactly three, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one one phenyluracil of formula (I), preferably of formula (I. a), and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), at least two, preferably exactly two herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one phenyluracil of formula (I), preferably of formula (I. a), at least three, preferably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b1), in particular selected from the group consisting of clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, metamifop, pinoxaden, profoxydim, sethoxydim, tepraloxydim, tralkoxydim, esprocarb, ethofumesate, molinate, prosulfocarb, thiobencarb and triallate.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b2), in particular selected from the group consisting of bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorsulfuron, clorimuron, cyclosulfamuron, diclosulam, florasulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapic-isopropylammonium, imazapyr, imazapyr-ammonium, imazethapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazethapyr-isopropylammonium, imazosulfuron, iodosulfuron-methyl- sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, metosulam, nicosulfuron, penoxsulam, propoxycarbazon-sodium, pyrazosulfuron-ethyl, pyribenzoxim, pyriftalid, pyroxsulam, propyrisulfuron, rimsulfuron, sulfosulfuron, thiencarbazon-methyl, thifensulfuron-methyl, tribenuron-methyl, tritosulfuron and triafamone.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting (l.a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, bentazon, bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, bromoxynil-potassium, diuron, fluometuron, hexazinone, isoproturon, linuron, metamitron, metribuzin, paraquat-dichloride, propanil, simazin, terbutryn and terbuthylazine.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b4), in particular selected from the group consisting of acifluorfen, butafencil, carfenetrazone-ethyl, flumioxazin, fomesafen, oxadiargyl, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, epyrifenacil, 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl)-1 (2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylic acid ethyl ester (CAS 1949837-17-5).
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b5), in particular selected from the group consisting of amitrole, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquintrone, fluometuron, flurochloridone, isoxaflutole, mesotrione, norflurazone, oxotrione (CAS 1486617-21-3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, topramezone-sodium, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol- 5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone, 2-(2,5-dichlorophenyl)- methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7), and rimisoxafen.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b6), in particular selected from the group consisting of glyphosate, glyphosate-ammonium, glyphosate- dimethylammonium , glyphosate-isopropylammonium and glyphosate-trimesium (sulfosate) and glyphosate-potassium.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b7), in particular selected from the group consisting of glufosinate, glufosinate-ammonium, glufosinate- P and glufosinate-P-ammonium. According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b9), in particular selected from the group consisting of pendimethalin and trifluralin.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of acetochlor, butachlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone. Likewise, preference is given to compositions comprising in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I. a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as defined above.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b11 ), in particular indaziflam, isoxaben and triaziflam.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b13), in particular selected from the group consisting of 2,4-D, 2,4-D-isobutyl, 2,4-D-dimethylammonium, 2,4-D-N,N,N-trimethylethanolammonium, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-methyl, aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium, clopyralid, clopyralid-methyl, clopyralid-olamine, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba- dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-potassium, dicamba-sodium, dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine, dicamba- diethylenetriamine, flopyrauxifen, fluroxypyr, fluroxypyr-meptyl, halauxifen, halauxifen-methyl, MCPA, MCPA-2-ethylhexyl, MCPA-dimethylammonium, quinclorac, quinclorac- dimethylammonium, quinmerac, quinmerac-dimethylammonium, florpyrauxifen, florpyrauxifen- benzyl (CAS 1390661-72-9), and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6).
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b14), in particular selected from the group consisting of diflufenzopyr, diflufenzopyr-sodium, dymron, indanofan and diflufenzopyr-sodium.
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one herbicidally active compound from group b15), in particular selected from the group consisting of cinmethylin, dymron (= daimuron), indanofan, oxaziclomefone, tetflupyrolimet, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl- pyridazin-3-one (CAS 2414510-21-5).
According to another preferred embodiment of the invention, the composition comprises, in addition to a phenyluracil of formula (I), especially an active compound from the group consisting of (I .a.19), (l.a.20), (l.a.21), (l.a.25), (l.a.26), (l.a.27), (l.a.31), (l.h.20), (l.q.20) and (l.r.20), at least one and especially exactly one safener C, in particular selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836- 31-4).
Here and below, the term “binary compositions” includes compositions comprising one or more, for example 1, 2 or 3, active compounds of the formula (I) and either one or more, for example 1, 2 or 3, herbicides B or one or more safeners C.
Correspondingly, the term “ternary compositions” includes compositions comprising one or more, for example 1, 2 or 3, active compounds of the formula (I), one or more, for example 1, 2 or 3, herbicides B and one or more, for example 1, 2 or 3, safeners C.
In binary compositions comprising at least one compound of the formula (I) as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.
In binary compositions comprising at least one compound of the formula (I) as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1.
In ternary compositions comprising at least one phenyluracil of formula (I) as component A, at least one herbicide B and at least one safener C, the relative proportions by weight of the components A:B are generally in the range of from 1 :1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1:250 to 250:1 and particularly preferably in the range of from 1 :75 to 75: 1 , the weight ratio of the components A:C is generally in the range of from 1:1000 to 1000:1, preferably in the range of from 1:500 to 500:1, in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1:75 to 75:1 , and the weight ratio of the components B:C is generally in the range of from 1 : 1000 to 1000: 1 , preferably in the range of from 1 :500 to 500: 1 , in particular in the range of from 1 :250 to 250: 1 and particularly preferably in the range of from 1 :75 to 75:1. The weight ratio of components A + B to component C is preferably in the range of from 1 :500 to 500: 1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1.
Further preferable mixing ratios by weight of the present phenyluracils of formula (I) as component A to one or more compounds selected from the group consisting of the herbicides B according to the present invention are about 1 :0.1 , 1 :0.2, 1 :0.3, 1 :0.5, 1 :0.6, 1 :0.7, 1 :0.8, 1 :1 , 1 :1.2, 1 :1.4, 1 :1.6, 1 :1.8, 1 :2, 1 :2.2, 1 :2.4, 1 :2.6, 1 :2.8, 1 :3, 1 :5, 1 :7, 1 :10, 1 :15, 1 :20, 1 :30, 1 :40 and 1 :50.
"About" as used herein in this context includes a range of a ratio increased or decreased by 10% by weight compared with a specified ratio.
For example, about 1 :2 includes a range of 1 : 1.8 to 1 :2.2.
The weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.
Particularly preferred are the compositions mentioned below comprising the phenyluracils of formula (I) as defined and the substance(s) as defined in the respective row of table 1 ; especially preferred comprising as only herbicidal active compounds the phenyluracil of formula (I) as defined and the substance(s) as defined in the respective row of table 1 ; most preferably comprising as only active compounds the phenyluracils of formula (I) as defined and the substance(s) as defined in the respective row of table 1 .
Particularly preferred are compositions 1.1 to 1.3887, comprising the phenyluracil of formula (I. a.20) and the substance(s) as defined in the respective row of table 1 :
Table 1 (compositions 1.1 to 1.3887):
Figure imgf000053_0001
Figure imgf000053_0002
Figure imgf000053_0003
Figure imgf000054_0001
Figure imgf000054_0002
Figure imgf000054_0003
Figure imgf000055_0001
Figure imgf000055_0002
Figure imgf000055_0003
Figure imgf000056_0001
Figure imgf000056_0002
Figure imgf000056_0003
Figure imgf000057_0001
Figure imgf000057_0002
Figure imgf000057_0003
Figure imgf000058_0001
Figure imgf000058_0002
Figure imgf000058_0003
Figure imgf000059_0001
Figure imgf000059_0002
Figure imgf000059_0003
Figure imgf000060_0001
Figure imgf000060_0002
Figure imgf000060_0003
Figure imgf000061_0001
Figure imgf000061_0002
Figure imgf000061_0003
Figure imgf000062_0001
Figure imgf000062_0002
Figure imgf000062_0003
Figure imgf000063_0001
Figure imgf000063_0002
Figure imgf000063_0003
Figure imgf000064_0001
Figure imgf000064_0002
Figure imgf000064_0003
Figure imgf000065_0001
Figure imgf000065_0002
Figure imgf000065_0003
Figure imgf000066_0001
Figure imgf000066_0002
Figure imgf000066_0003
Figure imgf000067_0001
Figure imgf000067_0002
Figure imgf000067_0003
Figure imgf000068_0001
Figure imgf000068_0002
Figure imgf000068_0003
Figure imgf000069_0001
Figure imgf000069_0002
Figure imgf000069_0003
Figure imgf000070_0001
Figure imgf000070_0002
Figure imgf000070_0003
Figure imgf000071_0001
Figure imgf000071_0002
Figure imgf000071_0003
Figure imgf000072_0001
Figure imgf000072_0002
Figure imgf000072_0003
Figure imgf000073_0001
Figure imgf000073_0002
Figure imgf000073_0003
Figure imgf000074_0001
Figure imgf000074_0002
Figure imgf000074_0003
Figure imgf000075_0001
Figure imgf000075_0002
Figure imgf000075_0003
Figure imgf000076_0001
Figure imgf000076_0002
Figure imgf000076_0003
Figure imgf000077_0001
Figure imgf000077_0002
Figure imgf000077_0003
Figure imgf000078_0001
Figure imgf000078_0002
Figure imgf000078_0003
Figure imgf000079_0001
Figure imgf000079_0002
Figure imgf000079_0003
Figure imgf000080_0001
Figure imgf000080_0002
Figure imgf000080_0003
Figure imgf000081_0001
Figure imgf000081_0002
Figure imgf000081_0003
Figure imgf000082_0001
Figure imgf000082_0002
Figure imgf000082_0003
Figure imgf000083_0003
Figure imgf000083_0001
Figure imgf000083_0002
The specific number for each single composition is deductible as follows: Composition 1.200 for example comprises the phenyluracil (I. a.20) and cinmethylin (B.200) (see table 1 , entry 1.200; as well as table B, entry B.200).
Composition 2.200 for example comprises the phenyluracil (I. a.19) (see the definition for compositions 2.1 to 2.3887 below) and cinmethylin (B.200) (see table 1 , entry 1.200; as well as table B, entry B.200).
Composition 7.200 for example comprises imazapyr (B.35) (see the definition for compositions 7.1 to 7.3887 below), the phenyluracil (I. a.20) and cinmethylin (B.200) (see table 1 , entry 1.200; as well as table B, entry B.200).
Also especially preferred are compositions 2.1. to 2.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.19).
Also especially preferred are compositions 3.1. to 3.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.2 as further herbicide B.
Also especially preferred are compositions 4.1. to 4.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.8 as further herbicide B.
Also especially preferred are compositions 5.1. to 5.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.30 as further herbicide B.
Also especially preferred are compositions 6.1. to 6.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.32 as further herbicide B.
Also especially preferred are compositions 7.1. to 7.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.35 as further herbicide B.
Also especially preferred are compositions 8.1. to 8.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.38 as further herbicide B.
Also especially preferred are compositions 9.1. to 9.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.40 as further herbicide B.
Also especially preferred are compositions 10.1. to 10.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.51 as further herbicide B.
Also especially preferred are compositions 11.1. to 11.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.55 as further herbicide B.
Also especially preferred are compositions 12.1. to 12.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.56 as further herbicide B.
Also especially preferred are compositions 13.1. to 13.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.64 as further herbicide B.
Also especially preferred are compositions 14.1. to 14.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.66 as further herbicide B.
Also especially preferred are compositions 15.1. to 15.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.67 as further herbicide B.
Also especially preferred are compositions 16.1. to 16.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.68 as further herbicide B.
Also especially preferred are compositions 17.1. to 17.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.69 as further herbicide B.
Also especially preferred are compositions 18.1. to 18.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.73 as further herbicide B.
Also especially preferred are compositions 19.1. to 19.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.76 as further herbicide B.
Also especially preferred are compositions 20.1. to 20.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.81 as further herbicide B.
Also especially preferred are compositions 21.1. to 21.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.82 as further herbicide B.
Also especially preferred are compositions 22.1. to 22.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.85 as further herbicide B.
Also especially preferred are compositions 23.1. to 23.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.88 as further herbicide B.
Also especially preferred are compositions 24.1. to 24.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.89 as further herbicide B.
Also especially preferred are compositions 25.1. to 25.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.94 as further herbicide B.
Also especially preferred are compositions 26.1. to 26.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.95 as further herbicide B.
Also especially preferred are compositions 27.1. to 27.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.98 as further herbicide B.
Also especially preferred are compositions 28.1. to 28.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.100 as further herbicide B.
Also especially preferred are compositions 29.1. to 29.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.103 as further herbicide B.
Also especially preferred are compositions 30.1. to 30.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.103 and B.67 as further herbicides B.
Also especially preferred are compositions 31.1. to 31.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.103 and B.76 as further herbicides B.
Also especially preferred are compositions 32.1. to 32.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.103 and B.82 as further herbicides B.
Also especially preferred are compositions 33.1. to 33.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.104 as further herbicide B.
Also especially preferred are compositions 34.1. to 34.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.104 and B.67 as further herbicides B.
Also especially preferred are compositions 35.1. to 35.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.104 and B.76 as further herbicides B.
Also especially preferred are compositions 36.1. to 36.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.104 and B.82 as further herbicides B.
Also especially preferred are compositions 37.1. to 37.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.106 as further herbicide B.
Also especially preferred are compositions 38.1. to 38.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.107 as further herbicide B.
Also especially preferred are compositions 39.1. to 39.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B. 107 and B.67 as further herbicides B.
Also especially preferred are compositions 40.1. to 40.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B. 107 and B.76 as further herbicides B.
Also especially preferred are compositions 41.1. to 41.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B. 107 and B.82 as further herbicides B.
Also especially preferred are compositions 42.1. to 42.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.109 as further herbicide B.
Also especially preferred are compositions 43.1. to 43.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.111 as further herbicide B.
Also especially preferred are compositions 44.1. to 44.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.111 and B.67 as further herbicides B.
Also especially preferred are compositions 45.1. to 45.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.111 and B.76 as further herbicides B.
Also especially preferred are compositions 46.1. to 46.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.111 and B.82 as further herbicides B. Also especially preferred are compositions 47.1. to 47.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B. 116 as further herbicide B.
Also especially preferred are compositions 48.1. to 48.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.67 as further herbicides B.
Also especially preferred are compositions 49.1. to 49.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.94 as further herbicides B.
Also especially preferred are compositions 50.1. to 50.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.103 as further herbicides B.
Also especially preferred are compositions 51.1. to 51.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.128 as further herbicides B.
Also especially preferred are compositions 52.1. to 52.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.104 as further herbicides B.
Also especially preferred are compositions 53.1. to 53.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.107 as further herbicides B.
Also especially preferred are compositions 54.1. to 54.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.116 and B.111 as further herbicides B.
Also especially preferred are compositions 55.1. to 55.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.122 as further herbicide B.
Also especially preferred are compositions 56.1. to 56.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.126 as further herbicide B.
Also especially preferred are compositions 57.1. to 57.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.128 as further herbicide B.
Also especially preferred are compositions 58.1. to 58.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.131 as further herbicide B.
Also especially preferred are compositions 59.1. to 59.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.132 as further herbicide B.
Also especially preferred are compositions 60.1. to 60.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.133 as further herbicide B.
Also especially preferred are compositions 61.1. to 61.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.135 as further herbicide B.
Also especially preferred are compositions 62.1. to 62.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.137 as further herbicide B. Also especially preferred are compositions 63.1. to 63.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.138 as further herbicide B.
Also especially preferred are compositions 64.1. to 64.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.140 as further herbicide B.
Also especially preferred are compositions 65.1. to 65.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.145 as further herbicide B.
Also especially preferred are compositions 66.1. to 66.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.153 as further herbicide B.
Also especially preferred are compositions 67.1. to 67.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.156 as further herbicide B.
Also especially preferred are compositions 68.1. to 68.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.171 as further herbicide B.
Also especially preferred are compositions 69.1. to 69.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.174 as further herbicide B.
Also especially preferred are compositions 70.1. to 70.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they additionally comprise B.202 as further herbicide B.
Also especially preferred are compositions 71.1. to 71.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.a.20-stereoisomer 1).
Also especially preferred are compositions 72.1. to 72.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.a.20-stereoisomer 2).
Also especially preferred are compositions 73.1. to 73.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.21).
Also especially preferred are compositions 74.1. to 74.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.25).
Also especially preferred are compositions 75.1. to 75.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.26).
Also especially preferred are compositions 76.1. to 76.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.27).
Also especially preferred are compositions 77.1. to 77.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (I. a.31).
Also especially preferred are compositions 78.1. to 78.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.h.20).
Also especially preferred are compositions 79.1. to 79.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.q.20).
Also especially preferred are compositions 80.1. to 80.3887 which differ from the corresponding compositions 1.1 to 1.3887 only in that they comprise as the active compound A the phenyuluracil of formula (l.r.20).
Also especially preferred are compositions 81.1. to 81.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.2 as further herbicide B.
Also especially preferred are compositions 82.1. to 82.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.8 as further herbicide B.
Also especially preferred are compositions 83.1. to 83.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.30 as further herbicide B.
Also especially preferred are compositions 84.1. to 84.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.32 as further herbicide B.
Also especially preferred are compositions 85.1. to 85.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.35 as further herbicide B.
Also especially preferred are compositions 86.1. to 86.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.38 as further herbicide B.
Also especially preferred are compositions 87.1. to 87.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.40 as further herbicide B.
Also especially preferred are compositions 88.1. to 88.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.51 as further herbicide B.
Also especially preferred are compositions 89.1. to 89.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.55 as further herbicide B.
Also especially preferred are compositions 90.1. to 90.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.56 as further herbicide B.
Also especially preferred are compositions 91.1. to 91.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.64 as further herbicide B.
Also especially preferred are compositions 92.1. to 92.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.66 as further herbicide B. Also especially preferred are compositions 93.1. to 93.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.67 as further herbicide B.
Also especially preferred are compositions 94.1. to 94.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.68 as further herbicide B.
Also especially preferred are compositions 95.1. to 95.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.69 as further herbicide B.
Also especially preferred are compositions 96.1. to 96.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.73 as further herbicide B.
Also especially preferred are compositions 97.1. to 97.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.76 as further herbicide B.
Also especially preferred are compositions 98.1. to 98.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.81 as further herbicide B.
Also especially preferred are compositions 99.1. to 99.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.82 as further herbicide B.
Also especially preferred are compositions 100.1. to 100.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.85 as further herbicide B.
Also especially preferred are compositions 101.1. to 101.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.88 as further herbicide B.
Also especially preferred are compositions 102.1. to 102.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.89 as further herbicide B.
Also especially preferred are compositions 103.1. to 103.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.94 as further herbicide B.
Also especially preferred are compositions 104.1. to 104.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.95 as further herbicide B.
Also especially preferred are compositions 105.1. to 105.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.98 as further herbicide B.
Also especially preferred are compositions 106.1. to 106.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.100 as further herbicide B.
Also especially preferred are compositions 107.1. to 107.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.103 as further herbicide B.
Also especially preferred are compositions 108.1. to 108.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.103 and B.67 as further herbicides B.
Also especially preferred are compositions 109.1. to 109.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.103 and B.76 as further herbicides B.
Also especially preferred are compositions 110.1. to 110.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.103 and B.82 as further herbicides B.
Also especially preferred are compositions 111.1. to 111.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.104 as further herbicide B.
Also especially preferred are compositions 112.1. to 112.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.104 and B.67 as further herbicides B.
Also especially preferred are compositions 113.1. to 113.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.104 and B.76 as further herbicides B.
Also especially preferred are compositions 114.1. to 114.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.104 and B.82 as further herbicides B.
Also especially preferred are compositions 115.1. to 115.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.106 as further herbicide B.
Also especially preferred are compositions 116.1. to 116.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.107 as further herbicide B.
Also especially preferred are compositions 117.1. to 117.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B. 107 and B.67 as further herbicides B.
Also especially preferred are compositions 118.1. to 118.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B. 107 and B.76 as further herbicides B.
Also especially preferred are compositions 119.1. to 119.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B. 107 and B.82 as further herbicides B.
Also especially preferred are compositions 120.1. to 120.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.109 as further herbicide B.
Also especially preferred are compositions 121.1. to 121.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.111 as further herbicide B.
Also especially preferred are compositions 122.1. to 122.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.111 and B.67 as further herbicides B.
Also especially preferred are compositions 123.1. to 123.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.111 and B.76 as further herbicides B. Also especially preferred are compositions 124.1. to 124.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.111 and B.82 as further herbicides B.
Also especially preferred are compositions 125.1. to 125.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B. 116 as further herbicide B.
Also especially preferred are compositions 126.1. to 126.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.67 as further herbicides B.
Also especially preferred are compositions 127.1. to 127.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.94 as further herbicides B.
Also especially preferred are compositions 128.1. to 128.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.103 as further herbicides B.
Also especially preferred are compositions 129.1. to 129.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.128 as further herbicides B.
Also especially preferred are compositions 130.1. to 130.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.104 as further herbicides B.
Also especially preferred are compositions 131.1. to 131.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.107 as further herbicides B.
Also especially preferred are compositions 132.1. to 132.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.116 and B.111 as further herbicides B.
Also especially preferred are compositions 133.1. to 133.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.122 as further herbicide B.
Also especially preferred are compositions 134.1. to 134.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.126 as further herbicide B.
Also especially preferred are compositions 135.1. to 135.3887 which differ from the corresponding compositions 173.1 to 73.3887 only in that they additionally comprise B.128 as further herbicide B.
Also especially preferred are compositions 136.1. to 136.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.131 as further herbicide B.
Also especially preferred are compositions 137.1. to 137.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.132 as further herbicide B.
Also especially preferred are compositions 138.1. to 138.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.133 as further herbicide B.
Also especially preferred are compositions 139.1. to 139.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.135 as further herbicide B. Also especially preferred are compositions 140.1. to 140.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.137 as further herbicide B.
Also especially preferred are compositions 141.1. to 141.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.138 as further herbicide B.
Also especially preferred are compositions 142.1. to 142.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.140 as further herbicide B.
Also especially preferred are compositions 143.1. to 143.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.145 as further herbicide B.
Also especially preferred are compositions 144.1. to 144.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.153 as further herbicide B.
Also especially preferred are compositions 145.1. to 145.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.156 as further herbicide B.
Also especially preferred are compositions 146.1. to 146.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.171 as further herbicide B.
Also especially preferred are compositions 147.1. to 147.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.174 as further herbicide B.
Also especially preferred are compositions 148.1. to 148.3887 which differ from the corresponding compositions 73.1 to 73.3887 only in that they additionally comprise B.202 as further herbicide B.
The invention also relates to agrochemical compositions comprising an auxiliary and at least one composition according to the invention.
An agrochemical composition comprises a pesticidally effective amount of at least one composition according to the invention. The term "effective amount" denotes an amount of the active ingredients, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in crops (i.e. cultivated plants) and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated crop or material, the climatic conditions and the specific composition according to the invention used.
The compounds A and ottionally B and/or C, their N-oxides, salts or derivatives can be converted into customary types of agrochemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for agrochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further agrochemical compositions types are defined in the “Catalogue of pesticide formulation types and international coding system”, Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol.1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers. Examples for agrochemical composition types and their preparation are: i) Water-soluble concentrates (SL, LS)
10-60 wt% of a compostion according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water. ii) Dispersible concentrates (DC)
5-25 wt% of a composition according to the invention and 1-10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion. iii) Emulsifiable concentrates (EC)
15-70 wt% of a composition according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion. iv) Emulsions (EW, EO, ES)
5-40 wt% of a composition according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a composition according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added. vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a composition according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance. vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a composition according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance. viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a acomposition according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance. iv) Microemulsion (ME)
5-20 wt% of a composition according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion. iv) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a composition according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4’-diisocyanate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1-10 wt%. The wt% relate to the total CS composition. ix) Dustable powders (DP, DS)
1-10 wt% of a composition according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%. x) Granules (GR, FG)
0.5-30 wt% of a composition according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or the fluidized bed. xi) Ultra-low volume liquids (UL)
1-50 wt% of a composition according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
The agrochemical compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1-1 wt% anti-foaming agents, and 0,1-1 wt% colorants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
Methods for applying phenyluracils of formula (I) and compositions thereof, respectively, on to plant propagation material, especially seeds include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, compound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1, preferably 1:10 to 10:1.
The user applies the agrochemical composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g. agrochemical components comprising phenyluracils of formula (I) and/or active substances from the groups B and/or C may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
In a further embodiment, individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
In a further embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g. components comprising phenyluracils of formula (I) and active substances from the groups B and/or C, can be applied jointly (e.g. after tank mix) or consecutively.
Accordingly, a first embodiment of the invention relates to compositions in the form of a agrochemical composition formulated as a 1 -component composition comprising the at least one active phenyluracil of formula (I) or the at least one active phenyluracil of formula (I) (active compound A) and at least one further active compound selected from the herbicides B and the safeners C and also a solid or liquid carrier and, if appropriate, one or more surfactants.
Accordingly, a second embodiment of the invention relates to compositions in the form of a agrochemical composition formulated as a 2-component composition comprising a first formulation (component) comprising the at least one active compound A, a solid or liquid carrier and, if appropriate, one or more surfactants, and a second component comprising at least one further active compound selected from the herbicides B and safeners C, a solid or liquid carrier and, if appropriate, one or more surfactants.
The active compound A and the at least one further active compound B and/or C can be formulated and applied jointly or separately, simultaneously or in succession, before, during or after the emergence of the plants. In case of separate application, the order of the application of the active compounds A, B and/or C is of minor importance. The only thing that is important is that the at least one active compound A and the at least one further active compound B and/or C are present simultaneously at the site of action, i.e. are at the same time in contact with or taken up by the plant to be controlled / safened. The compositions according to the invention are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).
The compositions according to the invention control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leafed weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
The compositions according to the invention have an outstanding herbicidal activity against undesired vegetation, i.e. against a broad spectrum of economically important harmful monocotyledonous and dicotyledonous weeds.
Mentioned below are some representatives of monocotyledonous and dicotyledonous weeds, which can be controlled by the compositions according to the invention without the enumeration being a restriction to certain species.
Preferably the compositions according to the invention are used to control monocotyledonous weeds.
Examples of monocotyledonous weeds on which the compositions according to the invention act efficiently are selected from the genera Hordeum spp., Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Brachiaria spp., Leptochloa spp., Avena spp., Cyperus spp., Axonopris spp., Sorghum spp., and Melinus spp..
Preferred examples of monocotyledonous weeds on which the compositions according to the invention act efficiently are selected from the species Hordeum murinum, Echinochloa crus- galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis, Digitaria insularis, Eriochloa gracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea, Panicum miliaceum, Lolium multiflorum, Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, and Melinus repens.
Especially preferred examples of monocotyledonous weeds on which the compositions according to the invention act efficiently are selected from the species Echinochloa spp., Digitaria spp., Setaria spp., Eleusine spp. and Brachiarium spp.
Also preferably the compositions according to the invention are used to control dicotyledonous weeds.
Examples of dicotyledonous weeds on which the compositions according to the invention act efficiently are selected from the genera Amaranthus spp., Erigeron spp., Conyza spp., Polygonum spp., Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp., Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp., Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., llrtica spp., Sida spp, Portulaca spp., Richardia spp., Ambrosia spp., Calandrinia spp., Sisymbrium spp., Sesbania spp., Capsella spp., Sonchus spp., Euphorbia spp., Helianthus spp., Coronopus spp., Salsola spp., Abutilon spp., Vicia spp., Epilobium spp., Cardamine spp., Pieris spp., Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solarium spp., Oxalis spp., Metricaria spp., Plantago spp., Tribulus spp., Cenchrus spp. Bidens spp., Veronica spp., and Hypochaeris spp..
Preferred examples of dicotyledonous weeds on which the compositions according to the invention act efficiently are selected from the species Amaranthus spinosus, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum offi cinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis (Conyza bonariensis), Senecio vulgaris, Lamium amplexicaule, Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra, Sinapis arvensis, llrtica dioica, Amaranthus blitoides, Amaranthus retroflexus, Amaranthus hybridus, Amaranthus lividus, Sida spinosa, Portulaca oleracea, Richardia scabra, Ambrosia artemisiifolia, Calandrinia caulescens, Sisymbrium irio, Sesbania exaltata, Capsella bursa-pastoris, Sonchus oleraceus, Euphorbia maculate, Helianthus annuus, Coronopus didymus, Salsola tragus, Abutilon theophrasti, Vicia benghalensis L., Epilobium paniculatum, Cardamine spp, Pieris echioides, Trifolium spp., Galinsoga spp., Epimedium spp., Marchantia spp., Solanum spp., Oxalis spp., Metricaria matriccarioides, Plantago spp., Tribulus terrestris, Salsola kali, Cenchrus spp., Bidens bipinnata, Veronica spp., and Hypochaeris radicata.
Especially preferred examples of dicotyledonous weeds on which the compositions according to the invention act efficiently are selected from the species Amaranthus spp., Erigeron spp., Conyza spp., Kochia spp. and Abutilon spp.
The compositions according to the invention are applied to the plants mainly by spraying the leaves. Here, the application can be carried out using, for example, water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (for example from 300 to 400 l/ha). The herbicidal compositions may also be applied by the low- volume or the ultra-low-volume method, or in the form of microgranules.
Application of the herbicidal compositions according to the present invention can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
The herbicidal compositions according to the present invention can be applied pre- or postemergence or together with the seed of a crop plant. It is also possible to apply the compounds and compositions by applying seed, pretreated with a composition of the invention, of a crop plant. If the active compounds A and B and, if appropriate C, are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or the bare soil surface (post- directed, lay-by).
In a further embodiment, the composition according to the invention can be applied by treating seed. The treatment of seed comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula (I) according to the invention or the compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.
The term “seed” comprises seed of all types, such as, for example, corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
Moreover, it may be advantageous to apply the compositions of the present invention on their own or jointly in combination with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria or with groups of active compounds which regulate growth. Also of interest is the miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
When employed in plant protection, the amounts of active substances applied, i.e. A and B and, if appropriate, C without formulation auxiliaries, are, depending on the kind of effect desired, from 0.001 to 3 kg per ha, preferably from 0.005 to 2.5 kg per ha, more preferably from 0.01 to 2 kg per ha and in particular from 0.025 to 1.5 kg per ha.
In another preferred embodiment of the invention, the rates of application of the phenyluracil of formula (I) according to the present invention (total amount of phenyluracil of formula (I)) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.
In another preferred embodiment of the invention, the application rates of the phenyluracil of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha.
In another preferred embodiment of the invention, the application rate of the phenyluracil of formula (I) is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha.
The required application rates of herbicidal compounds B are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
The required application rates of safeners C are generally in the range of from 0.0005 kg/ha to 2.5 kg/ha and preferably in the range of from 0.005 kg/ha to 2 kg/ha or 0.01 kg/ha to 1.5 kg/h of a.s.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
In another embodiment of the invention, to treat the seed, the amounts of active substances applied, i.e. A and B and, if appropriate, C are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
In the methods of the present invention it is immaterial whether the herbicide phenyluracil of formula (I), and the further herbicide component B and/or the herbicide safener compound C are formulated and applied jointly or separately.
In the case of separate application it is of minor importance, in which order the application takes place. It is only necessary, that the herbicide phenyluracil and the herbicide compound B and/or the herbicide safener compound C are applied in a time frame that allows simultaneous action of the active ingredients on the plants, preferably within a time-frame of at most 35 days, in particular at most 14 days.
Depending on the application method in question, the compositions according to the invention can additionally be employed in a further number of crop plants for eliminating undesirable plants.
According to the invention all the crop plants (cultivated plants) mentioned herein are understood to comprise all species, subspecies, variants and/or hybrids which belong to the respective cultivated plants, including but not limited to winter and spring varieties, in particular in cereals such as wheat and barley, as well as oilseed rape, e.g. winter wheat, spring wheat, winter barley etc..
For example, corn is also known as Indian corn or maize (Zea mays) which comprises all kinds of corn such as field corn and sweet corn. According to the invention all maize or corn subspecies and/or varieties are comprised, in particular flour corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy corn (Zea mays var. ceratina), amylomaize (high amylose Zea mays varieties), pod corn or wild maize (Zea mays var. tunicata) and striped maize (Zea mays var. japonica).
Further, most soybean cultivars are classifiable into indeterminate and determinate growth habit, whereas Glycine soja, the wild progenitor of soybean, is indeterminate (PNAS 2010, 107 (19) 8563-856). The indeterminate growth habit (Maturity Group, MG 00 to MG 4.9) is characterized by a continuation of vegetative growth after flowering begins whereas determinate soybean varieties (Maturity Group, (MG) 5 to MG 8) characteristically have finished most of their vegetative growth when flowering begins. According to the invention all soybean cultivars or varieties are comprised, in particular indeterminate and determinate cultivars or varieties.
Examples of suitable crops are the following: Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. Silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec., Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
Preferred crops are Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays
Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, peas, lentils, peanuts or permanent crops.
The compositions according to the invention can also be used in crops which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
The term "crops" as used herein includes also (crop) plants which have been modified by mutagenesis or genetic engineering in order to provide a new trait to a plant or to modify an already present trait.
Mutagenesis includes techniques of random mutagenesis using X-rays or mutagenic chemicals, but also techniques of targeted mutagenesis, in order to create mutations at a specific locus of a plant genome. Targeted mutagenesis techniques frequently use oligonucleotides or proteins like CRISPR/Cas, zinc-finger nucleases, TALENs or meganucleases to achieve the targeting effect.
Genetic engineering usually uses recombinant DNA techniques to create modifications in a plant genome which under natural circumstances cannot readily be obtained by cross breeding, mutagenesis or natural recombination. Typically, one or more genes are integrated into the genome of a plant in order to add a trait or improve a trait. These integrated genes are also referred to as transgenes in the art, while plant comprising such transgenes are referred to as transgenic plants. The process of plant transformation usually produces several transformation events, wich differ in the genomic locus in which a transgene has been integrated. Plants comprising a specific transgene on a specific genomic locus are usually described as comprising a specific “event”, which is referred to by a specific event name. Traits which have been introduced in plants or hae been modified include in particular herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions, like drought.
Herbicide tolerance has been created by using mutagenesis as well as using genetic engineering. Plants which have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional methods of mutagenesis and breeding comprise plant varieties commercially available under the name Clearfield®. However, most of the herbicide tolerance traits have been created via the use of transgenes.
Herbicide tolerance has been created to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides, like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides and 4- hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, like isoxaflutole and mesotrione.
Transgenes wich have been used to provide herbicide tolerance traits comprise: for tolerance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for tolerance to glufosinate: pat and bar, for tolerance to 2,4-D: aad-1 and aad-12, for tolerance to dicamba: dmo, for tolerance to oxynil herbicies: bxn, for tolerance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA, for tolerance to ALS inhibitor herbicides: csr1-2, for tolerance to HPPD inhibitor herbicides: hppdPF, W336 and avhppd-03.
Transgenic corn events comprising herbicide tolerance genes are for example, but not excluding others, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411 , MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO- 01981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.
Transgenic soybean events comprising herbicide tolerance genes are for example, but not excluding others, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS- 81419-2, GU262, SYHT0H2, W62, W98, FG72 and CV127.
Transgenic cotton events comprising herbicide tolerance genes are for example, but not excluding others, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701 , MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40.
Transgenic canola events comprising herbicide tolerance genes are for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.
Insect resistance has mainly been created by transferring bacterial genes for insecticidal proteins to plants. Transgenes which have most frequently been used are toxin genes of Bacillus spec, and synthetic variants thereof, like cry1A, crylAb, cry1 Ab-Ac, crylAc, cry1A.1O5, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1 , cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. However, also genes of plant origin have been transferred to other plants. In particular genes coding for protease inhibitors, like CpTI and pinll. A further approach uses transgenes in order to produce double stranded RNA in plants to target and downregulate insect genes. An example for such a transgene is dvsnf7. Transgenic corn events comprising genes for insecticidal proteins or double stranded RNA are for example, but not excluding others, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411 , MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.
Transgenic soybean events comprising genes for insecticidal proteins are for example, but not excluding others, MON87701, MON87751 and DAS-81419.
Transgenic cotton events comprising genes for insecticidal proteins are for example, but not excluding others, SGK321 , MON531 , MON757, MON 1076, MON 15985, 31707, 31803, 31807, 31808, 42317, BNLA-601 , Eventl , COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.
Increased yield has been created by increasing ear biomass using the transgene athb17, being present in corn event MON87403, or by enhancing photosynthesis using the transgene bbx32, being present in the soybean event MON87712.
Crops comprising a modified oil content have been created by using the transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A. Soybean events comprising at least one of these genes are: 260-05, MON87705 and MON87769.
Tolerance to abiotic conditions, in particular to tolerance to drought, has been created by using the transgene cspB, comprised by the corn event MON87460 and by using the transgene Hahb-4, comprised by soybean event IND-00410-5.
Traits are frequently combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combination of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different kind of insects, in particular tolerance to lepidopteran and coleopteran insects, herbicide tolerance with one or several types of insect resistance, herbicide tolerance with increased yield as well as a combination of herbicide tolerance and tolerance to abiotic conditions.
Plants comprising singular or stacked traits as well as the genes and events providing these traits are well known in the art. For example, detailed information as to the mutagenized or integrated genes and the respective events are available from websites of the organizations “International Service for the Acquisition of Agri-biotech Applications (ISAAA)” (http://www.isaaa.org/gmapprovaldatabase) and the “Center for Environmental Risk Assessment (CERA)” (http://cera-amc.org/GMCropDatabase), as well as in patent applications, like EP3028573 and WG2017/011288.
The use of compositions according to the invention on crops may result in effects which are specific to a crop comprising a certain gene or event. These effects might involve changes in growth behavior or changed resistance to biotic or abiotic stress factors. Such effects may in particular comprise enhanced yield, enhanced resistance or tolerance to insects, nematodes, fungal, bacterial, mycoplasma, viral or viroid pathogens as well as early vigour, early or delayed ripening, cold or heat tolerance as well as changed amino acid or fatty acid spectrum or content.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).
Furthermore, it has been found that the the compositions according to the invention are also suitable for the defoliation and/or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, are suitable. In this regard compositions have been found for the desiccation and/or defoliation of plants, processes for preparing these compositions, and methods for desiccating and/or defoliating plants using the compositions according to the invention.
As desiccants, the compositions according to the invention are suitable in particular for desiccating the above-ground parts of crop plants such as potato, oilseed rape, sunflower and soybean, but also cereals. This makes possible the fully mechanical harvesting of these important crop plants.
Also of economic interest is the facilitation of harvesting, which is made possible by concentrating within a certain period of time the dehiscence, or reduction of adhesion to the tree, in citrus fruit, olives and other species and varieties of pomaceous fruit, stone fruit and nuts. The same mechanism, i.e. the promotion of the development of abscission tissue between fruit part or leaf part and shoot part of the plants is also essential for the controlled defoliation of useful plants, in particular cotton.
Moreover, a shortening of the time interval in which the individual cotton plants mature leads to an increased fiber quality after harvesting.
The following examples serve to illustrate the invention.
A Preparation examples
Methyl 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate
Figure imgf000106_0001
Example 1 - stepl : terf-Butyl N-(2,5-difluoro-4-nitro-phenyl)carbamate
Figure imgf000106_0002
WO 2023/030934 l uo PCT/EP2022/073269
4-Dimethylaminopyridine (12.2 g, 100 mmol) was added to a solution of 2,5-difluoro-4-nitro- aniline (CAS 1542-36-5; 172 g, 1 mol), bis-(1 , 1 -dimethylethyl) dicarbonate (327 g, 1.5 mol) in dichloromethane (2 L) at 25 °C. The mixture was stirred at 25 °C for 18 h. The resulting mixture was concentrated and purified with silica gel column (ethylacetate : petrolether 1 :9) to give tert- butyl N-(2,5-difluoro-4-nitro-phenyl)carbamate (250 g, 91.2%) as yellow solid.
1H NMR (CDCI3 400MHz): 5 ppm = 8.27 (dd, J=13.1 , 6.6 Hz, 1 H), 7.91 (dd, J=10.6, 6.6 Hz, 1 H), 7.05 (br s, 1 H), 1.57 (s, 9H).
Example 1 - step 2: tert-butyl N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitro-phenyl]carbamate
Figure imgf000107_0001
To a solution of tert-butyl N-(2,5-difluoro-4-nitro-phenyl)carbamate (250 g, 911 mmol) and K2CO3 (377 g, 2733 mmol) in acetonitrile (2.5 L) was added 2-methoxyphenol (136 g, 1094 mmol) at 15 °C. Then the mixture was stirred at 80 °C for 18 h. The mixture was filtered and the filtrate was concentrated. The residue was diluted with ethylacetate, washed with H2O, brine, dried over Na2SC>4 and concentrated. The residue was triturated with ethylacetate : petrolether 1 :3 (1 L) to give tert-butyl N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitro-phenyl]carbamate (220 g, 64%) as yellow solid.
1H NMR (400 MHz, DMSO-d6) 5 ppm = 9.63 (s, 1 H) 8.04 (d, J=10.6 Hz, 1 H), 7.45 (d, J=6.7 Hz, 1 H), 7.19 - 7.29 (m, 2 H), 7.13 (d, J=7.7 Hz, 1 H), 6.98 - 7.03 (m, 1 H), 3.74 (s, 3 H), 1.37 (s, 9 H).
Example 1 - step 3: tert-butyl N-[4-amino-2-fluoro-5-(2-methoxyphenoxy)phenyl]carbamate
Figure imgf000107_0002
To the solution of tert-butyl N-[2-fluoro-5-(2-methoxyphenoxy)-4-nitro-phenyl]carbamate (210 g, 555 mmol) in ethanol (3.6 L) was added Pd/C (21 g) under N2 and stirred at 25 °C under H2 (50 Psi) for 24 h. The mixture was filtered and concentrated to give tert-butyl N-[4-amino-2-fluoro-5- (2-methoxyphenoxy)phenyl]carbamate (170 g, 80.6%) as a brown solid.
1H NMR (400 MHz, DMSO-d6) 5 ppm = 8.34 (br s, 1 H), 7.06 - 7.15 (m, 2 H), 6.86 - 6.93 (m, 1 H), 6.78 - 6.84 (m, 1 H), 6.61 (br s, 1 H), 6.55 (d, J=12.1 Hz, 1 H), 5.02 (s, 2 H), 3.79 (s, 3 H), 1.36 (s, 9 H). Example 1 - step 4: terf-butyl N-[4-bromo-2-fluoro-5-(2-methoxyphenoxy)phenyl]carbamate
Figure imgf000108_0001
To the mixture of CuBr2 (26.6 g, 120 mmol) in acetonitrile (200 mL) was added isoamyl nitrite (10.5 g, 90 mmol) at 25 °C. Then, the mixture was warmed to 60 °C. terf-butyl N-[4-amino-2- fluoro-5-(2-methoxyphenoxy)phenyl]-carbamate (31g, 60mmol) was added in portions at 60 °C and stirred for 1 h at 60 °C. Then the mixture was diluted with H2O, extracted with ethylacetate twice. The organic layer was washed with brine, dried over Na2SC>4 and concentrated. The crude was purified by column (ethylacetate : petrolether 1 : 4) to give terf-butyl N-[4-bromo-2- fluoro-5-(2-methoxyphenoxy)phenyl]carbamate (13 g, 52.5%) as a brown solid.
1H NMR (400 MHz, CDCh) 6 ppm = 7.72 (br s, 1 H), 7.33 (d, J=10.2 Hz, 1H), 7.13 - 7.07 (m, 1 H), 7.02 - 6.99 (m, 1 H), 6.92 - 6.86 (m, 1 H), 6.83 - 6.79 (m, 1 H), 6.61 (br s, 1 H), 3.88 (s, 3H), 1.45 (s, 9H).
Example 1 - step 5: 4-bromo-2-fluoro-5-(2-methoxyphenoxy)aniline
Figure imgf000108_0002
To terf-butyl N-[4-bromo-2-fluoro-5-(2-methoxyphenoxy)phenyl]carbamate (3 g, 7.3 mmol) was added 4N HCI in ethylacetate (30 mL) in portions at 0 °C and stirred for 16 h at 20 °C. The mixture was poured into H2O, extracted with ethylacetate, and the organic layer was washed with brine, dried over Na2SC>4 and concentrated to give 4-bromo-2-fluoro-5-(2- methoxyphenoxy)aniline (2.3 g, crude) as a brown solid.
1H NMR (400MHz, CDCI3) 6 ppm = 7.23 (d, J=10.2 Hz, 1 H), 7.15 - 7.09 (m, 1H), 7.01 (dd,
J=1.2, 8.1 Hz, 1 H), 6.93 - 6.88 (m, 1 H), 6.87 - 6.83 (m, 1H), 6.27 (d, J=8.2 Hz, 1H), 3.87 (s, 3H), 3.69 (br s, 2H).
Example 1 - step 6: 3-[4-bromo-2-fluoro-5-(2-methoxyphenoxy)phenyl]-6-(trifluoromethyl)-1 H- pyrimidine-2, 4-dione
Figure imgf000108_0003
To a solution of 4-bromo-2-fluoro-5-(2-methoxyphenoxy)aniline (1.8 g, 5.8 mol) in acetic acid (5 mL) was added 2-(dimethylamino)-4-(trifluoromethyl)-1 ,3-oxazin-6-one (CAS 141860-79-9, 1.8 g, 8.7 mmol) at 20 °C. The mixture was stirred at 75 °C for 16 h. The mixture was poured into water and extracted with ethylacetate. The organic layer was washed with brine, dried over Na2SC>4 and concentrated to give 3-[4-bromo-2-fluoro-5-(2-methoxyphenoxy)phenyl]-6- (trifluoromethyl)-1 H-pyrimidine-2, 4-dione (3.2 g, crude) as a black solid.
Example 1 - step 7: 3-[4-bromo-2-fluoro-5-(2-methoxyphenoxy)phenyl]-1-methyl-6-(trifluoro- methyl)-pyrimidine-2, 4-dione
Figure imgf000109_0001
To a mixture of 3-[4-bromo-2-fluoro-5-(2-methoxyphenoxy)phenyl]-6-(trifluoromethyl)-1 H- pyrimidine-2, 4-dione (4.1 g, 8.6 mmol) in acetonitrile (40 mL) was added K2CO3 (4.7 g, 34.2 mmol) and methyliodide (2.5 g, 17.3 mmol) dropwise with stirring at 25 °C. Then, it was stirred for 16 h at 60 °C. The mixture was filtered, and the filtrate was concentrated. The crude was triturated, with ethylacetate : petrolether 1 : 10 (30 mL) to give 3-[4-bromo-2-fluoro-5-(2- methoxyphenoxy)phenyl]-1-methyl-6-(trifluoromethyl)pyrimidine-2, 4-dione (3.4 g, crude) as a yellow solid.
1H NMR (400 MHz, CDCh) 6 ppm = 7.54 (d, J=8.7 Hz, 1 H), 7.20 - 7.14 (m, 1 H), 7.05 (dd, J=1.5, 7.9 Hz, 1 H), 7.00 (dd, J=1 .2, 8.2 Hz, 1 H), 6.97 - 6.92 (m, 1 H), 6.57 (d, J=6.4 Hz, 1 H), 6.30 (s, 1 H), 3.81 (s, 3H), 3.51 (s, 3H).
Example 1 step 8: 3-[4-bromo-2-fluoro-5-(2-hydroxyphenoxy)phenyl]-1-methyl-6-(trifluoro- methyl)-pyrimidine-2, 4-dione
Figure imgf000109_0002
To a solution of 3-[4-bromo-2-fluoro-5-(2-methoxyphenoxy)phenyl]-1-methyl-6-(trifluoro- methyl)pyrimidine-2, 4-dione (3.4 g, 6.9 mmol) in CH2CI2 (50 mL) was added BBrs (3.5 g, 13.9 mmol) dropwise with stirring at 0 °C. The mixture was stirred at 25 °C for 2 h. The mixture was poured into ice water and extracted with ethylacetate. The organic layer was washed with brine (100 mL), dried over Na2SC>4, filtered and concentrated to give 3-[4-bromo-2-fluoro-5-(2- hydroxyphenoxy)phenyl]-1-methyl-6-(trifluoromethyl)pyrimidine-2, 4-dione (2.3 g, 66% over steps 6, 7 and 8) as a yellow solid.
1H NMR (400 MHz, CDCh-d) 5 ppm = 7.56 (d, J = 8.8 Hz, 1 H), 7.08 - 7.01 (m, 2H), 6.90 - 6.81 (m, 3H), 6.31 (s, 1 H), 5.66 (br s, 1 H), 3.53 - 3.50 (s, 3H). Example 1 - step 9: methyl 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)- pyrimidin-1-yl]phenoxy]phenoxy]-2-methoxy-acetate
Figure imgf000110_0001
To a solution of 3-[4-bromo-2-fluoro-5-(2-hydroxyphenoxy)phenyl]-1-methyl-6-(trifluoromethyl)- pyrimidine-2, 4-dione (1 g, 2.1 mmol) in DMF (10 mL) was added CS2CO3 (2.1 g, 6.3 mmol), methyl 2-bromo-2-methoxyacetate (CAS 5193-96-4, 772 mg, 4.2 mol) at 10 °C. Then the reaction was stirred at 10 °C for 16 h. The mixture was poured into water and extracted with ethylacetate. The organic layer was washed with brine (30 ml), dried over anhydrous Na2SO4, concentrated. The crude was purified by column (ethylacetate : petrolether 1 : 5) and by prep-HPLC (acetonitrile - H2O) to give methyl 2-[2-[2-bromo-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-pyrimidin-1- yl]phenoxy]phenoxy]-2-methoxy-acetate (0.285 g, 23%) as white solid.
1H NMR (400 MHz, DMSO-d6) 5 ppm = 7.94 (d, J=8.8 Hz, 1 H), 7.23 (d, J=1 .8 Hz, 1 H), 7.23 - 7.18 (m, 1 H), 7.15 - 7.10 (m, 1 H), 7.08 - 7.04 (m, 1 H), 6.96 (d, J=6.6 Hz, 1 H), 6.50 (d, J=1.8 Hz, 1 H), 5.67 (d, J=1.8 Hz, 1 H), 3.68 (d, J=1.8 Hz, 3H), 3.35 (s, 3H), 3.29 (d, J=6.6 Hz, 3H).
The phenyluracils listed below in tables 2 and 3 can be prepared similarly to the example mentioned above.
Figure imgf000110_0002
Table 2
Figure imgf000110_0003
*[M+NH4]; **[M+Na]
Figure imgf000111_0001
B Use examples
The herbicidal action of the compounds and compositions according to the invention was demonstrated by the following greenhouse experiments:
The culture containers used were plastic pots containing loamy sand with approximately 3.0% of humus as substrate. The seeds of the test plants were sown separately for each species. For the pre-emergence treatment, the active compounds, suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants unless this was adversely affected by the active compounds.
For the post-emergence treatment, the test plants were grown to a plant height of from 3 to 15 cm, depending on the plant habit, and only then treated with the active compounds which had been suspended or emulsified in water. To this end, the test plants were either sown directly, and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment.
Depending on the species, the plants were kept at 10 - 25°C and 20 - 35°C, respectively.
The test period extended over 2 to 4 weeks. During this time, the plants were tended and their response to the individual treatments was evaluated.
Evaluation was carried out using a scale from 0 to 100. 100 means no emergence of the plants, or complete destruction of at least the above-ground parts, and 0 means no damage or normal course of growth. A good herbicidal activity is given at values of at least 70, and very good herbicidal activity is given at values of at least 85.
If not stated differently, the respective components A and B, and if appropriate, C were formulated as a 5% by weight strength emulsion concentrate and, with addition of the amount of solvent system, introduced into the spray liquor used for applying the active compound.
In the examples below, using the method of S. R. Colby (1967) “Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds 15, p. 22ff. , the value E, which is expected if the activity of the individual active compounds is only additive, was calculated. E = X + Y - (XY/100) where
X = percent activity using active compound A at an application rate a;
Y = percent activity using active compound B at an application rate b; E = expected activity (in %) by A + B at application rates a + b.
If the value found experimentally is higher than the value E calculated according to Colby, a synergistic effect is present.
The following active compounds have been tested:
Phenyluracils of formula (I) phenyluracil (I. a.20) phenyluracil (l.a.20-stereoisomer 1) phenyluracil (l.a.20-stereoisomer 2) phenyluracil (I. a.21)
The phenyuracils of formula (I) were used as an EC formulation having an active ingredient concentration of 5% (5w/w%).
Herbicides B : group b.1 : herbicide B.1 : clethodim (240 g/L EC) group b.2 : herbicide B.32 imazapic (240 g/L SL) herbicide B.35 imazapyr (240 g/L SL) herbicide B.40 imazethapyr (240 g/L SL) group b.4 : herbicide B.94 saflufenacil (342 g/L SC) herbicide B.95 sulfentrazone (480 g/L SC) herbicide B.96 trifludimoxazin (500 g/L, SC) methyl (1S,4R)-4-[[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-1 ,2-oxazol-5- yl]carbonyl]amino]-cyclopent-2-en-1-carboxylat (CAS 2365468-20-6) group b.5 : herbicide B.111 : topramezone (336 g/l SC) group b.6 : herbicide B.116: glyphosate (540 g/L SL) group b.7 : herbicide B.124 : L-glufosinate (5 w/w% EC) herbicide B.122 glufosinate (280 g/L SL) group b9 : herbicide B.126 pendimethalin (400 g/L SC) group b.10 : herbicide B.131 dimethenamid-p (720 g/L EC) herbicide B.135 metazachlor (500 g/L SC) herbicide B.144 pyroxasulfone (850 g/kg WG) group b.13: herbicide B.145 2,4 D (660 g/L EC) herbicide B.156/1 : dicamba (200 g/L SL) herbicide B.156/2: dicamba (600 g/L SL) The plants used in the greenhouse experiments were of the following species:
Figure imgf000113_0002
Figure imgf000113_0001
The results of these tests are given below in the use examples and demonstrate the synergistic effect of the mixtures comprising at least one phenyluracil of the formula (I) and at least one herbicide B. In this context, a.i. means active ingredient, based on 100 % active ingredient.
As indicated application was either post emergent (POST) at the respective growth stage (GS) of the weed (BBCH code), or pre-emergent (PRE).
Assessment was 20 days after treatment (DAT).
Example 1: Synergistic herbicidal action of the composition 1.1 (POST, GS 12-16)
Figure imgf000113_0003
Example 2: Synergistic herbicidal action of the composition1.32 (POST, GS 12-16)
Figure imgf000114_0001
Example 3: Synergistic herbicidal action of the composition 1.40 (POST, GS 12-16)
Figure imgf000114_0002
Example 4: Synergistic herbicidal action of the composition 1.94 (POST, GS 12-16)
Figure imgf000114_0003
Example 5: Synergistic herbicidal action of the composition 1.95 (POST, GS 12-16)
Figure imgf000114_0004
Example 6: Synergistic herbicidal action of the composition 1.96 (POST, GS 12-16)
Figure imgf000115_0001
Example 7: Synergistic herbicidal action of the composition 1.111 (POST, GS 12-16)
Figure imgf000115_0002
Example 8: Synergistic herbicidal action of the composition 1.116 (POST, GS 12-16)
Figure imgf000116_0001
Example 9: Synergistic herbicidal action of the composition 1.122 (POST, GS 12-16)
Figure imgf000116_0002
Example 10: Synergistic herbicidal action of the composition 1.124 (POST, GS 12-16)
Figure imgf000117_0001
Example 11 : Synergistic herbicidal action of the composition 1.126 (POST, GS 12-16)
Figure imgf000117_0002
Example 12: Synergistic herbicidal action of the composition 1.131 (POST, GS 12-16)
Figure imgf000118_0001
Example 13: Synergistic herbicidal action of the composition 1.135 (POST, GS 12-16)
Figure imgf000118_0002
Example 14: Synergistic herbicidal action of the composition 1.144 (POST, GS 12-16)
Figure imgf000119_0001
Example 15: Synergistic herbicidal action of the composition 1.145 (POST, GS 12-16)
Figure imgf000119_0002
Example 16: Synergistic herbicidal action of the composition 1.156 (POST, GS 12-16)
Figure imgf000120_0001
Example 17: Synergistic herbicidal action of the composition 1.32 (PRE)
Figure imgf000120_0002
Example 18: Synergistic herbicidal action of the composition 1.35 (PRE)
Figure imgf000120_0003
Example 19: Synergistic herbicidal action of the composition 1.40 (PRE)
Figure imgf000121_0001
Example 20: Synergistic herbicidal action of the composition 1.94 (PRE)
Figure imgf000121_0002
Example 21 : Synergistic herbicidal action of the composition 1.95 (PRE)
Figure imgf000122_0001
Example 22: Synergistic herbicidal action of the composition 1 .96 (PRE)
Figure imgf000122_0002
Example 23: Synergistic herbicidal action of the composition 1.111 (PRE)
Figure imgf000122_0003
Example 24: Synergistic herbicidal action of the composition 1.126 (PRE)
Figure imgf000123_0001
Example 25: Synergistic herbicidal action of the composition 1.131 (PRE)
Figure imgf000123_0002
Example 26: Synergistic herbicidal action of the composition 1.135 (PRE)
Figure imgf000124_0001
Example 27: Synergistic herbicidal action of the composition 1.144 (PRE)
Figure imgf000124_0002
Figure imgf000125_0001
Example 28: Synergistic herbicidal action of the composition 71.40 (POST; GS 16-18)
Figure imgf000125_0002
Example 29: Synergistic herbicidal action of the composition 71.96 (POST; GS 16-18)
Figure imgf000125_0003
Example 30: Synergistic herbicidal action of the composition 71.116 (POST; GS 16-18)
Figure imgf000125_0004
Example 31 : Synergistic herbicidal action of the composition 71.122 (POST; GS 16-18)
Figure imgf000126_0001
Example 32: Synergistic herbicidal action of the composition 71.144 (POST; GS 16-18)
Figure imgf000126_0002
Example 33: Synergistic herbicidal action of the composition 71.40 (PRE)
Figure imgf000126_0003
Example 34: Synergistic herbicidal action of the composition 71.96 (PRE)
Figure imgf000127_0001
Example 35: Synergistic herbicidal action of the composition 71.131 (PRE)
Figure imgf000127_0002
Example 36: Synergistic herbicidal action of the composition 71.144 (PRE)
Figure imgf000128_0001
Example 37: Synergistic herbicidal action of the composition 72.40 (POST; GS 16-18/31)
Figure imgf000128_0002
Example 38: Synergistic herbicidal action of the composition 72.96 (POST; GS 16-18/31)
Figure imgf000128_0003
Figure imgf000129_0001
Example 39: Synergistic herbicidal action of the composition 72.116 (POST; GS 16-18/31)
Figure imgf000129_0002
Example 40: Synergistic herbicidal action of the composition 72.122 (POST; GS 16-18/31)
Figure imgf000129_0003
Figure imgf000130_0001
Example 41 : Synergistic herbicidal action of the composition 72.144 (POST; GS 16-18/31)
Figure imgf000130_0002
Example 42: Synergistic herbicidal action of the composition 72.40 (PRE)
Figure imgf000131_0001
Example 43: Synergistic herbicidal action of the composition 72.96 (PRE)
Figure imgf000131_0002
Example 44: Synergistic herbicidal action of the composition 72.131 (PRE)
Figure imgf000131_0003
Example 45: Synergistic herbicidal action of the composition 72.144 (PRE)
Figure imgf000132_0001
Example 46: Synergistic herbicidal action of the composition 73.1 (POST, GS 16-31)
Figure imgf000132_0002
Example 47: Synergistic herbicidal action of the composition 73.32 (POST, GS 16-31)
Figure imgf000133_0001
Example 48: Synergistic herbicidal action of the composition 73.40 (POST, GS 16-31)
Figure imgf000133_0002
Example 49: Synergistic herbicidal action of the composition 73.94 (POST, GS 16-31)
Figure imgf000134_0001
Example 50: Synergistic herbicidal action of the composition 73.95 (POST, GS 16-31)
Figure imgf000134_0002
Figure imgf000135_0001
Example 51 : Synergistic herbicidal action of the composition 73.96 (POST, GS 16-31)
Figure imgf000135_0002
Example 52: Synergistic herbicidal action of the composition 73.116 (POST, GS 16-31)
Figure imgf000136_0001
Example 53: Synergistic herbicidal action of the composition 73.122 (POST, GS 16-31)
Figure imgf000136_0002
Example 54: Synergistic herbicidal action of the composition 73.124 (POST, GS 16-31)
Figure imgf000137_0001
Example 55: Synergistic herbicidal action of the composition 73.131 (POST, GS 16-31)
Figure imgf000137_0002
Example 56: Synergistic herbicidal action of the composition 73.144 (POST, GS 16-31)
Figure imgf000138_0001
Example 57: Synergistic herbicidal action of the composition 73.145 (POST, GS 16-31)
Figure imgf000138_0002
Example 58: Synergistic herbicidal action of the composition 73.156 (POST, GS 16-31)
Figure imgf000139_0001
Example 59: Synergistic herbicidal action of the composition 73.40 (PRE)
Figure imgf000139_0002
Example 60: Synergistic herbicidal action of the composition 73.96 (PRE)
Figure imgf000139_0003
Example 61 : Synergistic herbicidal action of the composition 73.131 (PRE)
Figure imgf000140_0001
Example 62: Synergistic herbicidal action of the composition 73.144 (PRE)
Figure imgf000140_0002
Example 63: Synergistic herbicidal action of the composition comprising phenyluracil (I. a.20) and methyl (1S,4R)-4-[[[(5S)-3-(3,5-difluorphenyl)-5-vinyl-4H-1,2-oxazol-5-yl]carbonyl]amino]- cyclopent-2-en-1-carboxylat (CAS 2365468-20-6;) (POST, GS 12-16; assessment 7 DAT)
Figure imgf000141_0001

Claims

Claims
1. Herbicidal compositions comprising
A) at least one phenyluracil of formula (I. a)
Figure imgf000142_0001
wherein the substituents have the following meanings:
R4 F;
R5 Ci-Cs-alkoxy,;
R6 is hydrogen or Ci-Ce-alkyl; including their agriculturally acceptable salts, amides, esters or thioesters, provided the phenyluracils of formula (I) have a carboxyl group; and at least one further active compound selected from
B) herbicides of class b1) to b15): b1) lipid biosynthesis inhibitors; b2) acetolactate synthase inhibitors (ALS inhibitors); b3) photosynthesis inhibitors; b4) protoporphyrinogen-IX oxidase inhibitors, b5) bleacher herbicides; b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors); b7) glutamine synthetase inhibitors; b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); b9) mitosis inhibitors; b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors); b11) cellulose biosynthesis inhibitors; b12) decoupler herbicides; b13) auxinic herbicides; b14) auxin transport inhibitors; and b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin, methyl azide, methyl bromide, methyl- dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tetflupyrolimet, triaziflam, tridiphane, 6-chloro-3-(2- cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters, 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin- 3-one (CAS 2414510-21-5); including their agriculturally acceptable salts, amides, esters or thioesters; and
C) safeners.
2. A herbicidal composition a claimed in claim 1 comprising at least one phenyluracil of formula (I. a), wherein R4 is F;
R5 is Ci-Cs-alkoxy; and R6 is H, CH3 or C2H5.
3. A herbicidal composition as claimed in claim 1 or 2 comprising at least one herbicide B selected from herbicides of class b1 , b2, b4, b5, b6, b7, b9, b10 and b13.
4. An agrochemical composition comprising the herbicidal composition as defined in any of the preceding claims and a solid or liquid carrier.
5. A method for controlling undesirable vegetation, which method comprises applying the composition as defined in any of the preceding claims to a locus where undesirable vegetation is present or is expected to be present.
6. The method as claimed in claim 5, comprising the application of the composition as defined in any of the preceding claims post crop emergence.
7. The method as claimed in claim 5 or 6, wherein the components of the composition as defined in claims 1 or 2 are applied jointly or separately, simultaneously or in succession.
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