Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/79—Acids; Esters
• • 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
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
  • C07D213/46—Oxygen atoms
  • C07D213/48—Aldehydo radicals

Definitions

• the present invention relates to pyridine compounds of the formula (I) defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation.
• the present invention provides the pyridine compounds of formula (I)
• R 1 is d-Ce-alkyl, d-Ce-haloalkyl, hydroxy-d-Ce-alkyl, C2-Ce-alkenyl, C2-Ce-haloalkenyl, C2- C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy-CrC 6 -alkyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-haloalkoxy, C3-C6- cycloalkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, Ci-C6-alkylthio, Ci-C6-haloalky
• R 2 is H, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl-Ci-C6-alkyl, Ci-C6-alkoxy- carbonyl-Ci-C6-alkyl, Ci-C6-haloalkylcarbonyl-Ci-C6-alkyl, Ci-C6-haloalkoxycarbonyl-Ci- C6-alkyl, Ci-C6-alkylcarbonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-
• heterocyclylcarbonylamino (heterocyclylcarbonyl)(Ci-C6-alkyl)amino,
• heteroarylcarbonylamino (heteroarylcarbonyl)(Ci-C6-alkyl)amino, [(C1-C6- alkyl)carbonyl](Ci-C6-alkoxy)amino, [(Ci-C6- aloalkyl)carbonyl](Ci-C6-alkoxy)amino, [(C3- C6-cycloalkyl)carbonyl](Ci-C6-alkyloxy)amino, (phenylcarbonyl)(Ci-C6-alkoxy)amino, (heterocyclylcarbonyl)(Ci-C6-alkoxy)amino, (heteroarylcarbonyl)(Ci-C6-alkoxy)amino, [(Ci C6-alkyl)carbonyl](C2-C6-alkenyl)amino, [(Ci-C6-haloalkyl)carbonyl](
• R 3 is halogen, CN, N0 2 , Ci-C 6 -alkyl, C C 6 -haloalkyl, C C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 - C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6- alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy- Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio,
• R 4 ' R 5 , R 6 , and R 7 independently of one another are
• R a is selected from halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci- C6-haloalkoxy;
• the present invention also provides the use of pyridine compounds of formula (I) as described herein including agriculturally acceptable salts or derivatives of the pyridine compounds of formula (I) having an acidic functionality, as herbicide.
• the present invention also provides agrochemical compositions comprising at least one pyridine compounds of formula (I) and auxiliaries customary for formulating crop protection agents.
• the present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one pyridine compounds of formula (I) is allowed to act on plants, their seeds and/or their habitat.
• Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
• the present invention also provides pyridine compounds of formula (I) as described herein.
• the pyridine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, for example by the following processes:
• the pyridine compounds of formula (I) can be obtained by reacting pyridines of formula (II) with boronic acids/esters of formula (III):
• the reaction of the pyridine (II) with boronic acids/esters (II I) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly preferably from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
• the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (II) with the boronic acids/esters (III) in an organic solvent with or without water as co-solvent.
• Suitable in principle are all solvents which are capable of dissolving the pyridines (II) and the boronic acids (III) at least partly and preferably fully under the reaction conditions.
• suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert.
• aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
• ethers such as diethyl ether, diisopropyl ether, tert.
• TBME -butyl methylether
• dioxane dioxane
• anisole and tetrahydrofuran as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, ⁇ , ⁇ -dimethylformamide (DMF), N,N-dimethyl- acetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), ⁇ , ⁇ '-dimethylpropylene urea
• DMPU dimethyl sulfoxide
• NMP 1-methyl-2 pyrrolidinone
• suitable metal-containing bases are inorganic compounds including metal- containing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as U2O, Na20, K2O, MgO, and CaO, Fe2C>3, Ag2 ⁇ D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC , as well as alkali metal bicarbonates such as LiHCC>3, NaHCC , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
• metal-containing bases such as al
• base as used herein also includes mixtures of two or more, preferably two of the above bases. Particular preference is given to the use of one base.
• the bases are used preferably from 1 to 10 equivalents based on the pyridine (II), more preferably from 1 .0 to 5.0 equivalents based on the pyridine (II), most preferably from 1.2 to 2.5 equivalents based on the pyridine (II).
• the reaction of the pyridines (II) with the boronic acids/esters (III) is carried out in the presence of a catalyst.
• suitable catalysts include for example, palladium based catalysts like, for example, Palladium(ll)acetate, tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)palladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)ferrocene)- dichloropalladium(ll), and optionally suitable additives such as, for example, phosphines like, for example, P(o-tolyl)3, triphenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1 ,1 '-binaphthyl).
• the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyridine (II).
• pyridine compounds (I), wherein R 2 has any one of the above mentioned meanings except OH can also be obtained by modifying pyridine compounds (I) wherein R 2 is
• boronic acids or esters (III) required for the preparation of pyridine compounds of formula (I) are commercially available, known from literature or can easily prepared analogously to published procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
• the pyridines (II) can easily prepared by the corresponding pyridines (IV) by modification of known methods.
• R 1 alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy-alkyl, cycloalkenyl, halocycloalkenyl, cycloalkyl-alkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6- membered heterocyclyl cross-coupling reactions can be used (methods analog to WO
• R 1 alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, cycloalkoxy, halocycloalkoxy, cycloalkenyloxy, halocycloalkenyloxy, alkylthio or (alkyl)amino SNAr substitution reactions
• Methods analog to Chem. Eur. J. 2012, 18, 2498- 2502, J. Med. Chem. 2012, 55, 10584-10600, WO2009099080 or to WO 201 1 100769 methods analog to Chem. Eur. J. 2012, 18, 2498- 2502, J. Med. Chem. 2012, 55, 10584-10600, WO2009099080 or to WO 201 1 100769.
• the pyridines (IV) wherein R 2 is OH can easily be modified by known methods (e.g. "oxy-substituents” except “OH” analogous to Arnab, P. et. al. Angew. Chem. Int. Ed. 2010, 49, 1492-1495; "thio-substituents” analogous to Silvestri, M. A. et. al. J. Med. Chem. 2004, 47, 3149-3162; "amino-substituents” analogous to Kuhn, B. et. al. J. Med. Chem. 2010, 53, 2601- 261 1 ).
• the pyridine compounds of formula (I) can in addition be obtained by reacting respective pyridine boronic acid esters of formula (V) with halides of formula (VI) in which X equals CI, Br or I:
• the reaction of the pyridine (V) with halides (VI) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly preferably from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
• the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (V) with the halides (VI) in an organic solvent with or without water as co- solvent.
• Suitable in principle are all solvents which are capable of dissolving the pyridines (V) and the halides (VI) at least partly and preferably fully under the reaction conditions.
• suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert. -butyl methylether (TBME), dioxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2- imidazolidinone (DMI), ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and NMP.
• aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
• ethers such as diethyl ether, diisopropyl
• suitable metal-containing bases are inorganic compounds including metal- containing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as U2O, Na20, K2O, MgO, and CaO, Fe2C>3, Ag2 ⁇ D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC , as well as alkali metal bicarbonates such as LiHCC>3, NaHCC , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2.
• metal-containing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH
• base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
• the bases are used preferably from 1 to 10 equivalents based on the pyridine (V), more preferably from 1 .0 to 5.0 equivalents based on the pyridine (V), most preferably from 1.2 to 2.5 equivalents based on the pyridine (V).
• the reaction of the pyridines (V) with the halides (VI) is carried out in the presence of a catalyst.
• a catalyst include for example, palladium based catalysts like, for example, Palladium(ll)acetate, tetrakis(triphenylphosphine)palladium(0),
• the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyridine (V).
• halides (VI) required for the preparation of pyridine compounds of formula (I) are known from the literature or are commercially available.
• the pyridines of formula (V) can be obtained by reacting the respective pyridines (II) with Bis(pinacolato)diboron VII.
• the reaction of the pyridine (II) with Bis(pinacolato)diboron VII is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly preferably from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
• the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (II) with Bis(pinacolato)diboron VII in an organic solvent with or without water as co-solvent.
• Suitable in principle are all solvents which are capable of dissolving the pyridines (II) and the Bis(pinacolato)diboron VII at least partly and preferably fully under the reaction conditions.
• suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert. -butyl methylether (TBME), dioxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2- imidazolidinone (DMI), ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and NMP.
• aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
• ethers such as diethyl ether, diisopropyl ether,
• suitable metal-containing bases are inorganic compounds including metal- containing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as U2O, Na20, K2O, MgO, and CaO, Fe2C>3, Ag2 ⁇ D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC , as well as alkali metal bicarbonates such as LiHCC>3, NaHCC , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
• metal-containing bases such as al
• base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
• the bases are used preferably from 1 to 10 equivalents based on the pyridine (II), more preferably from 1 .0 to 5.0 equivalents based on the pyridine (II), most preferably from 1.2 to 2.5 equivalents based on the pyridine (II).
• the reaction of the pyridines (II) with Bis(pinacolato)diboron VI is carried out in the presence of a catalyst.
• a catalyst include for example, palladium based catalysts like, for example, Palladium(ll)acetate, tetrakis(triphenylphosphine)palladium(0),
• phosphines like, for example, P(o-tolyl)3, triphenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1 ,1 '-binaphthyl).
• the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyridine (II).
• the end of the reaction can easily be determined by the skilled worker by means of routine methods.
• reaction mixtures are worked up in a customary manner, for example by mixing with water, separation of the phases and, if appropriate, chromatographic purification of the crude product.
• Some of the intermediates and end products are obtained in the form of viscous oils, which can be purified or freed from volatile components under reduced pressure and at moderately elevated temperature.
• purification can also be carried out by recrystallization or digestion.
• 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.
• pyridine compounds of formula (I) as described herein have one or more centres 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.
• pyridine compounds of formula (I) as described herein have ionisable functional groups, preferably an acidic functionality, 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, diisopropylammonium,
• 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.
• Pyridine compounds of formula (I) as described herein having a carboxyl group can be employed, if applicable, in the form of the acid, in the form of an agriculturally suitable salt, whereby the cations are defined as mentioned above, or else in the form of an agriculturally acceptable derivative, for example as amides, such as mono- and di-Ci-C6-alkylamides or arylamides, as esters, for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, for example as Ci-Cio-alkylthio esters.
• amides such as mono- and di-Ci-C6-alkylamides or arylamides
• esters for example as allyl esters, propargyl esters, Ci-Cio-alkyl esters, al
• Preferred mono- and di-Ci-C6-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-Cio-alkylthio ester is the ethylthio ester.
• the organic moieties mentioned in the definition of the variables R 1 to R 7 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, for example all alkyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix Cn-Cm denoting in each case the possible number of carbon atoms in the group.
• Ci-C 4 -alkyl for example CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, CH(CH 3 )-C2H 5 , CH 2 - CH(CH 3 ) 2 , and C(CH 3 ) 3 ;
• Ci-C6-alkyl Ci-C4-alkyl as mentioned above, and also, for example, n-pentyl, 1- methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethyl propyl, 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
• 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,
• 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,
• Ci-C6-haloalkyl Ci-C4-haloalkyl as mentioned above, and also, for example,
• C3-C6-cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
• C2-C6-alkenyl for example ethenyl, 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 - 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-
• C2-C6-haloalkenyl a C2-C6-alkenyl substituent 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-
• - C3-C6-alkynyl 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-
• C2-C6-alkynyl C3-C6-alkynyl as mentioned above and also ethynyl;
• C3-C6-haloalkynyl a C3-C6-alkynyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, for example 1 ,1 -difluoroprop-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,
• Ci-C4-alkoxy for example methoxy, ethoxy, propoxy, 1-methylethoxy butoxy, 1-methylpropoxy, 2-methylpropoxy, and 1 ,1 -dimethylethoxy;
• Ci-C6-alkoxy 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-methylpentoxy, 3- methylpentoxy, 4-methylpentoxy, 1 ,1-dimethylbutoxy, 1 ,2-dimethylbutoxy, 1 ,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1 -ethylbutoxy, 2-ethylbutoxy, 1 ,1 ,2- trimethylpropoxy, 1 ,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2- methylpropoxy.
• 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-bromo
• Ci-C6-haloalkoxy a Ci-C4-haloalkoxy as mentioned above, and also, for example, 5- fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluoro- hexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy, and dodecafluorohexoxy;
• Ci-C4-alkylthio for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, and 1 ,1-dimethylethylthio;
• Ci-C6-alkylthio Ci-C4-alkylthio as mentioned above, and also, for example, pentylthio, 1- methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1 -ethylpropylthio, hexylthio, 1 ,1-dimethylpropylthio, 1 ,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1 ,1 -dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3- dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 - ethylbutylthio, 2-ethylbuty
• (Ci-C4-alkyl)amino for example methylamino, ethylamino, propylamino, 1-methylethyl- amino, butylamino, 1-methylpropylamino, 2-methylpropylamino, or 1 ,1 -dimethylethylamino;
• (Ci-C6-alkyl)amino (Ci-C4-alkylamino) as mentioned above, and also, for example, pentylamino, 1 -methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2- dimethylpropylamino, 1 -ethylpropylamino, hexylamino, 1 ,1 -dimethylpropylamino, 1 ,2- dimethylpropylamino, 1 -methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4- methylpentylamino, 1 ,1 -dimethylbutylamino, 1 ,2-dimethylbutylamino, 1 ,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethylbutyl-amino 3,3-dimethylbutylamino, 1 -ethylbuty
• di(Ci-C4-alkyl)amino for example N,N-dimethylamino, ⁇ , ⁇ -diethylamino, N,N-di(1 - methylethyl)amino, N,N-dipropylamino, ⁇ , ⁇ -dibutylamino, N,N-di(1-methylpropyl)amino, N,N- di(2-methylpropyl)amino, N,N-di(1 ,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N- propylamino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1- methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1 ,1-dimethylethyl)
• di(Ci-C6-alkyl)amino di(Ci-C4-alkyl)amino as mentioned above, and also, for example, N-methyl-N-pentylamino, N-methyl-N-(1 -methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-methyl-N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1 - ethylpropyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1 ,1 -dimethylpropyl)amino, N-methyl-N- (1 ,2-dimethylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2- methylpentyl)amino, N-methyl-N-(3
• Ci-C6-alkylsulfonyl (Ci-C6-alkyl-S(0)2-) : 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-di- methylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexyls
• C3-C6-cycloalkyl a monocyclic saturated hydrocarbon having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
• C3-C6-cycloalkenyl 1-cyclopropenyl, 2-cyclopropenyl, 1 -cyclobutenyl, 2-cyclobutenyl, 1 - cyclopentenyl, 2-cyclopentenyl, 1 ,3-cyclopentadienyl, 1 ,4-cyclopentadienyl, 2,4- cyclopentadienyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1 ,3-cyclohexadienyl, 1 ,4- cyclohexadienyl, and 2,5-cyclohexadienyl;
• heterocyclyl a 3- to 6-membered heterocyclyl: a saturated or partial unsaturated cycle having three to six ring members which comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, for example
• heteroaryl a 5- or 6-membered heteroaryl: monocyclic aromatic heteroaryl having 5 to 6 ring members which, in addition to carbon atoms, contains 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an oxygen or a sulfur atom, , for example 5- membered aromatic rings like furyl (for example 2-furyl, 3-furyl), thienyl (for example 2-thienyl, 3-thienyl), pyrrolyl (for example pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (for example pyrazol-3-yl, pyrazol-4-yl), isoxazolyl (for example isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (for example isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (
• substituted if not specified otherwise refers to substituted by 1 , 2 or maximum possible number of substituents. If substituents as defined in compounds of formula I are more than one then they are independently from each other are same or different if not mentioned otherwise.
• acidic functionality if not specified otherwise refers to a functionality capable of donating a hydrogen (proton or hydrogen ion H + ), such as a carboxylic group or a sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
• a hydrogen proton or hydrogen ion H +
• the terms “compounds of formula (I)”, “Pyridine compounds of formula (I)”, “Compounds I” and “compounds of invention” are synonyms.
• pyridine compounds of formula (I) are suitable as herbicides.
• pyridine compounds of formula (I) and their use as herbicides, wherein the variables, either independently of one another or in combination with one another, have the following meanings:
• R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6- haloalkenyloxy C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkylthio, C3-C6-cycloalkyl, or phenyl,
• R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl,
• R 1 is C3-C6-cycloalkyl
• R 1 is C2H5, 1-C3H7, 1-C4H9, OCH3, C-C3H5, or C-C4H9;
• R 1 is C2H5, OCH3, or C-C3H5;
• R 1 is C-C3H5.
• R 2 is OH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, (Ci-C6-alkoxy)carbonyl-Ci-C6-alkoxy, Ci-C6-alkylthio, (Ci-C6-alkoxy)carbonyl-CrC6-alkylthio, NH 2 , Ci-C6-alkylcarbonylamino, C1-C6- haloalkylcarbonylamino, C3-C6-cycloalkylcarbonylamino, phenylcarbonylamino,
• R 2 is OH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkynyloxy, C1-C6- alkylthio, phenyloxy, Ci-C6-alkylcarbonylamino, Ci-C6-haloalkylcarbonylamino,
• phenylcarbonylamino heterocyclylcarbonylamino, heteroarylcarbonylamino, (C1-C6- alkoxy)amino, (Ci-C6-alkoxy)(Ci-C6-alkyl)amino, hydroxy(Ci-C6-alkyl)amino, hydroxyamino, or phenyl-Ci-C6-alkoxy, wherein the phenyl substituent is unsubstituted;
• R 2 is OH, Ci-C6-alkoxy, C3-C6-alkynyloxy or Ci-C6-haloalkoxy;
• Ci-C6-alkoxy especially preferred Ci-C6-alkoxy, C3-C6-alkynyloxy, Ci-C6-haloalkoxy, (Ci-C6-alkoxy)amino, or Ci-C6-alkylcarbonylamino;
• R 2 is OH, Ci-C6-alkoxy, or Ci-C6-haloalkoxy;
• R 2 is H, OH, or Ci-C6-alkoxy
• R 2 is OH, C3-C6-alkynyloxy, or Ci-C6-alkoxy
• R 2 is OH
• R 2 is C3-C6-alkynyloxy
• R 2 is Ci-C6-alkoxy.
• R 3 is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, Ci-Ce-alkoxy, or C3-C6- cycloalkyl;
• R 3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy, particularly preferred R 3 is halogen, CN, Ci-Ce-alkyI, or Ci-Ce-alkoxy;
• R 3 is halogen or CH3
• R 3 is halogen
• R 3 is CI, Br, or I
• R 3 is Br or I
• R 3 is CI or Br.
• R 4 is H, halogen, CN, Ci-C 6 -alkyl, CrC 6 -haloalkyl, or Ci-C 6 -alkoxy;
• R 4 is H, halogen, or Ci-Ce-alkyI
• R 4 is H or halogen
• R 4 is H or F
• R 4 is H
• R 4 is F.
• R 5 is H, halogen, CN, Ci-Ce-alkyl, Ci-C 6 -haloalkyl, or Ci-Ce-alkoxy;
• R 5 is H, halogen, CrC 6 -alkyl CrC 6 -haloalkyl, or Ci-C 6 -alkoxy;
• R 5 is H, halogen, CrC 6 -alkyl, or Ci-C 6 -haloalkyl
• R 5 is H, F, CI, CH3, or CF3;
• R 5 is H, halogen or CF3;
• R 5 is H, F or CF3;
• R 5 is H
• R 5 is F
• R 5 is CF3.
• R 6 is H, halogen, CrC 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
• R 6 is H, halogen, CrC 6 -alkyl, or C C 6 -haloalkyl
• R 6 is H, halogen, or Ci-Ce-alkyl
• R 6 is H, halogen, or d-Ce-haloalkyl
• R 6 is H, halogen or CF 3 ; most preferred R 6 is H, F, or CF 3 ;
• R 6 is H
• R 6 is F
• R 6 is CF3.
• R 7 is H, halogen, CN, Ci-C 6 -alkyl, or Ci-C 6 -alkoxy;
• R 7 is H, halogen, CrC 6 -alkyl, or C C 6 -alkoxy;
• R 7 is H, halogen, or Ci-Ce-alkyl
• R 7 is H, F, CI, or CH3;
• R 7 is H, F, or CI
• R 7 is CH3
• R 7 is H.
• R 1 is preferably CrC 6 -alkyl, Ci-C 6 -alkoxy, or C 3 -C 6 -cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
• R 1 is Cs-Ce-cycloalkyI, wherein the cycloalkyi substituent is unsubstituted;
• R 2 is preferably OH, Ci-Ce-alkoxy, C 3 -C 6 -alkynyloxy, or Ci-C 6 -haloalkoxy;
• R 2 is Ci-Ce-alkoxy, C 3 -C 6 -alkynyloxy, or Ci-C 6 -haloalkoxy
• R 2 is OH, Ci-Ce-alkoxy
• R 2 is OH; also more preferred R 2 is Ci-C6-alkoxy;
• R 3 is preferably R 3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 3 is halogen or CH3
• R 4 is preferably H
• R 5 is preferably H, halogen or CF3;
• R 6 is preferably H, halogen or CF 3 ;
• R 7 is preferably H, halogen, Ci-C6-alkyl, or Ci-C6-alkoxy.
• pyridine compounds of formula (I), and their use as herbicide wherein R 1 Ci-C6-alkoxy or C3-C6-cycloalkyl wherein the cycloalkyl substituent is unsubstituted; R 2 H, OH, or d-Ce-alkoxy;
• R 3 halogen, Ci-C6-alkyl, or Ci-C6-haloalkyl
• R 4 , R 6 , and R 7 are H
• R 5 H or halogen
• pyridine compounds of formula (I), and their use as herbicide wherein R c-C 3 H 5 or OCH 3 ;
• R 4 , R 6 , and R 7 are H
• pyridine compounds of formula (I), and their use as herbicide wherein R 1 C-C3H5, C-C4H7, C2H5, or OCH 3 ;
• R 3 CH 3 , OCH3, Br, I, CI, F, CF 3 , or CF 2 H;
• R 5 and R 6 are H or F.
• R 7 is H, CI, F, Br; CH 3 , or OCH 3 ;
• pyridine compounds of formula (I. a) corresponds to pyridine compounds of formula (I) wherein R 2 is OH, and R 4 is H , and their use as herbicide,
• pyridine compounds of formulae (l.a.1 ) to (I. a.672) of Table (I) corresponds to pyridine compounds of formula (I. a), and their use as herbicide, wherein the definitions of the variables R 1 , R 2 , R 3 , R 5 , R 6 and R 7 are of particular importance for the compounds according to the invention not only in combination with one another but in each case also on their own:
• R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
• R 2 is OH, Ci-C6-alkoxy, C3-C6-alkynyloxy, or Ci-C6-haloalkoxy;
• R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 5 is H, halogen, or CF 3 ;
• R 6 is H, halogen, or CF3
• R 7 is H, halogen, d-Ce-alkyl, or d-Ce-alkoxy.
• pyridine compounds of formula (I. A) correspond to pyridine compounds of formula (I), wherein R 2 is OH, R 4 is H and R 1 , R 3 R 5 , R 6 and R 7 are as defined below, and their use as herbicide;
• R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
• R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 5 is H, halogen or, CF3;
• R 6 is H, halogen or, CF3;
• R 7 is H, halogen, Ci-C6-alkyl, or Ci-C6-alkoxy.
• pyridine compounds of formula (I.B) correspond to pyridine compounds of formula (I), wherein R 4 is H, and R 1 , R 2 , R 3 , R 5 , R 6 and R 7 are as defined below, and their use as herbici
• R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
• R 2 is Ci-C6-alkoxy, C3-C6-alkynyloxy, or Ci-C6-haloalkoxy;
• R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 5 is H, halogen, or CF3;
• R 6 is H, halogen, or CF3
• R 7 is H, halogen, Ci-C6-alkyl, or Ci-C6-alkoxy.
• pyridine compounds of formula (I.B.1 ) correspond to pyridine compounds of formula (I), wherein R 2 is OCH3, R 4 is H, and R 1 , R 3 , R 5 , R 6 and R 7 are as defined below, and their use as herbicide;
• R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
• R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 5 is H, halogen, or CF 3 ;
• R 6 is H, halogen, or CF 3 ;
• R 7 is H, halogen, Ci-C6-alkyl, or Ci-C6-alkoxy;
• pyridine compounds of formulae (I.B.1 .1 ) to (I.B.1 .672) which corresponds to pyridine compounds of formula (I.B.1 ), wherein the variables R 1 , R 3 , R 5 , R 6 and R 7 are as defined for compounds of formula (l.a.1 ) to (I. a.672) in Table (I), and their use as herbicide.
• pyridine compounds of formula (I.B.2) correspond to pyridine compounds of formula (I), wherein R 2 is OC2H5, R 4 is H, and R 1 , R 3 , R 5 , R 6 and R 7 are as defined below, and their use as herbicide;
• R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
• R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 5 is H, halogen, or CF 3 ;
• R 6 is H, halogen, or CF3
• R 7 is H, halogen, Ci-C6-alkyl, or Ci-C6-alkoxy;
• pyridine compounds of formula (I.B.3) correspond to pyridine compounds of formula (I), wherein R 2 is OCH 2 C ⁇ CH, R 4 is H, and R 1 , R 3 , R 5 , R 6 and R 7 are as defined below, and their use as herbicide;
• R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
• R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 5 is H, halogen, or CF3;
• R 6 is H, halogen, or CF3
• R 7 is H, halogen, Ci-C6-alkyl, or Ci-C6-alkoxy;
• pyridine compounds of formula (I.B.4) correspond to pyridine compounds of formula (I), wherein R 2 is OCH2CHF2, R 4 is H, and R 1 , R 3 , R 5 , R 6 and R 7 are as defined below, and their use as herbicide;
• R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
• R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 5 is H, halogen, or CF 3 ;
• R 6 is H, halogen, or CF3
• R 7 is H, halogen, Ci-C6-alkyl, or Ci-C6-alkoxy;
• pyridine compounds of formula (I.B.5) correspond to pyridine compounds of formula (I), wherein R 2 is NHC(0)CH 3 , R 4 is H, and R 1 , R 3 , R 5 , R 6 and R 7 are as defined below, and their use as herbicide;
• R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
• R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 5 is H, halogen, or CF 3 ;
• R 6 is H, halogen, or CF 3 ;
• R 7 is H, halogen, Ci-C6-alkyl, or Ci-C6-alkoxy;
• pyridine compounds of formula (I.B.6) correspond to pyridine compounds of formula (I), wherein R 2 is NHOCH3, R 4 is H, and R 1 , R 3 , R 5 , R 6 and R 7 are as defined below, and their use as herbicide;
• R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
• R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
• R 5 is H, halogen, or CF 3 ;
• R 6 is H, halogen, or CF 3 ;
• R 7 is H, halogen, Ci-C6-alkyl, or Ci-C6-alkoxy;
• the pyridine compounds of formula (I) may be mixed with a large number of representatives of other herbicidal or growth- regulating active ingredient groups and then applied concomitantly.
• Suitable components for mixtures are, for example, herbicides from the classes of the acetamides, amides,
• aryloxyphenoxypropionat.es benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles,
• phenylpyrazolines phenylpyridazines, phosphinic acids, phosphoroamidates,
• phosphorodithioates phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones,
• triazolocarboxamides triazolopyrimidines, triketones, uracils, ureas.
• pyridine compounds of formula (I) alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria.
• miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies.
• Other additives such as non-phytotoxic oils and oil concentrates may also be added.
• compositions according to the present invention comprise at least one pyridine compound of formula (I) (compound A) and at least one further active compound selected from herbicides B, preferably herbicides B of class b1 ) to b15), and safeners C (compound C).
• the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.
• A) corresponds to pyridine compound of formula (I)), as defined herein;
• the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.B.1 ) (corresponds to pyridine compound of formula (I)), as defined herein;
• the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.B.2) (corresponds to pyridine compound of formula (I)), as defined herein;
• the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.B.3) (corresponds to pyridine compound of formula (I)), as defined herein;
• the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.B.4) (corresponds to pyridine compound of formula (I)), as defined herein;
• the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.B.5) (corresponds to pyridine compound of formula (I)), as defined herein;
• the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.B.6) (corresponds to pyridine compound of formula (I)), as defined herein;
• Preferred compounds of the formula (I) which, as component A, are constituent of the composition according to the invention are the compounds of formula I.A to I.B.6, as defined above;
• compositions according to the present invention comprise at least one pyridine compound of formula (I) and at least one further active compound B (herbicide B).
• the further herbicidal compound B (component B) is preferably selected from the herbicides of class b1 ) to b15):
• compositions can be selected from below herbicides B as defined below:
• ALS inhibitors acetolactate synthase inhibitors
• PPO inhibitors protoporphyrinogen-IX oxidase inhibitors
• EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
• DHP inhibitors 7,8-dihydropteroate synthase inhibitors
• mitosis inhibitors b8-dihydropteroate synthase inhibitors
• VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
• 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 (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA,
• the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1 ). These compounds inhibit lipid biosynthesis. Inhibition of the lipid biosynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter- termed ACCase herbicides) or through a different mode of action (hereinafter termed non-
• the ACCase herbicides belong to the group A of the HRAC classification system whereas the non-ACCase herbicides belong to the group N of the HRAC classification.
• compositions contain at least one ALS inhibitor (herbicide b2).
• ALS inhibitor hereinafter 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 - unknown
• compositions contain at least one EPSP synthase inhibitor (herbicide b6).
• EPSP synthase inhibitor herebicide 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.
• the compositions contain at least one cellulose biosynthesis inhibitor (herbicide b1 1 ).
• 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.
• 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.
• 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.
• compositions contain at least one auxin transport inhibitor (herbicide b14).
• auxin transport inhibitor hereinicide b14
• the herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants.
• compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b4, b5, b6, b9, b10, b13, and b14.
• compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, b13, and b14.
• compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, and b13
• herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
• 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
• 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, nicos
• 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;
• compositions comprising at least one imidazolinone herbicide
• 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-methyl-2H-pyr
• 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.
• 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;
• acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,
• PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS NOS NOS NOS NOS NOS NOS
• HPPD inhibitors benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21 -3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1 - methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361 139-71-0), 2-(2,4- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5- dichlorophenyl)methyl-4,4
• bilanaphos biases
• bilanaphos biases
• bilanaphos- sodium bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium
• 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;
• 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 and isoxazoline compounds of the formulae 11.1 , II.2, 11.3 , II.4, II.5, II.6, II.7, II .8 and II.9
• isoxazoline compounds are known in the art, e.g. from WO 2006/024820, WO
• chloroacetamides and oxyacetamides preference is given to chloroacetamides and oxyacetamides; b1 1 ) 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 );
• 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 salt
• Preferred herbicides B that can be used in combination with the pyrimidine compounds of the formula (I) according to the present invention are:
• acifluorfen-sodium bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon- ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl- 2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridy
• glyphosate glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
• glufosinate glufosinate-P, glufosinate-ammonium
• 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)ammoni- urn 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
• auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
• b15 from the group of the other herbicides: bromobutide, cinmethylin, cumyluron,
• herbicides B that can be used in combination with the pyrimidine compounds of the formula (I) according to the present invention are:
• lipid biosynthesis inhibitors from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyha- lofop-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
• cyclosulfamuron diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron,
• 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 );
• diflufenican fenquinotrione, flumeturon, flurochloridone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21 -3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate,
• glufosinate from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;
• VLCFA inhibitors 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;
• 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);
• auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
• herbicides B are the herbicides B as defined above; in particular, the herbicides B.1 - B.202 listed below in table B:
• compositions according to the present invention comprise at least one pyrimidine compound 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 post- emergence application of the useful plant.
• the safeners and the pyrimidine compounds 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
• 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-(dichloro- acetyl)-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, e.g., The Compendium of Pesticide Common Names
• 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.
• 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-diethylammoni- um, 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.
• 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 e.g. 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethyl- ammonium.
• Suitable esters of 2,4-DB are e.g. 2,4-DB-butyl and 2,4-DB-isoctyl.
• Suitable salts of dichlorprop are e.g. 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 clopyralid-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 e.g. 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 e.g. 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 e.g. glufosinate-ammonium.
• a suitable salt of glufosinate-P is e.g. glufosinate-P-ammonium.
• Suitable salts and esters of bromoxynil are e.g. bromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
• Suitable salts and esters of ioxonil are e.g. 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 e.g. 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 e.g. diflufenzopyr-sodium.
• a suitable salt of naptalam is e.g. naptalam-sodium.
• Suitable salts and esters of aminocyclopyrachlor are e.g. aminocyclopyrachlor- dimethylammonium, aminocyclopyrachlor-methyl, aminocyclopyrachlor- triisopropanolammonium, aminocyclopyrachlor-sodium and aminocyclopyrachlor-potassium.
• a suitable salt of quinclorac is e.g. quinclorac-dimethylammonium.
• a suitable salt of quinmerac is e.g. quinmerac-dimethylammonium.
• a suitable salt of imazamox is e.g. imazamox-ammonium.
• Suitable salts of imazapic are e.g. imazapic-ammonium and imazapic-isopropylammonium.
• Suitable salts of imazapyr are e.g. imazapyr-ammonium and imazapyr-isopropylammonium.
• a suitable salt of imazaquin is e.g. imazaquin-ammonium.
• Suitable salts of imazethapyr are e.g. imazethapyr-ammonium and imazethapyr- isopropylammonium.
• a suitable salt of topramezone is e.g. 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 pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), and as component B at least one, preferably exactly one, herbicide B.
• component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), and as component B at least one, preferably exactly one, herbicide B.
• the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), 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 pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), 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 pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), and as component C at least one, preferably exactly one, safener C.
• component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), and as component C at least one, preferably exactly one, safener C.
• the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.
• component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), 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 pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), at least two, preferably exactly two herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
• component A at least one, preferably exactly pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), 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 pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), at least three, preferably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
• component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .a), especially preferred the compound (l.a.25), (I. a.31 ), (I. a.37), (I. a.49), (I. a.55), (I. a.61 ), or (I. a.73), 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 pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), or (l.a.73), 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
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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,
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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.
• a pyridine compounds of formula (I) especially an active compound from the group consisting (l.
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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 , ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-di
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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 and 2-chloro-3-methyl
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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 pyridine compounds of formula (I) especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73),
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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 pyridine compounds of formula (I) especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), at least one and especially exactly one herbicidally active compound from group b7), in particular selected from the group consisting of gluf
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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 pyridine compounds of formula (I) especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), at least one and especially exactly one herbicidally active compound from group b9), in particular selected from the group consisting of pendimethalin and trifluralin.
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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 pyridine compounds of formula (I) especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55
• compositions comprising in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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 pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), at least one and especially exactly one herbicidally active compound from group b1 1 ), in particular indaziflam, isoxaben and triaziflam.
• a pyridine compounds of formula (I) especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), at least one and especially exactly one herbicidally active compound from group b1 1 ), in particular indaziflam, isoxaben and triaziflam.
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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,
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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
• a pyridine compounds of formula (I) especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), at least one and especially exactly one herbicidally active compound from group b15), in particular selected from the group consisting of cinmethylin, dy
• the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (l.a.25), (l.a.31 ), (l.a.37), (l.a.49), (l.a.55), (l.a.61 ), and (l.a.73), 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).
• 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
• 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 pyridine compounds of formula I as defined and the substance(s) as defined in the respective row of table T;
• compositions 1.1 to 1.3653, comprising the compound (I. a.25) and the substance(s) as defined in the respective row of table T:

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• 2017
  • 2017-07-24 WO PCT/EP2017/068604 patent/WO2018019758A1/fr active Application Filing

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