WO2018019770A1 - Composés de pyridine herbicides - Google Patents

Composés de pyridine herbicides Download PDF

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WO2018019770A1
WO2018019770A1 PCT/EP2017/068651 EP2017068651W WO2018019770A1 WO 2018019770 A1 WO2018019770 A1 WO 2018019770A1 EP 2017068651 W EP2017068651 W EP 2017068651W WO 2018019770 A1 WO2018019770 A1 WO 2018019770A1
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alkyl
alkoxy
amino
carbonyl
haloalkoxy
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PCT/EP2017/068651
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English (en)
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Florian Vogt
Matthias Witschel
Tobias SEISER
Veronica LOPEZ CARRILLO
Thomas Seitz
Gerd Kraemer
Trevor William Newton
Stefan Tresch
Doreen Schachtschabel
Klaus Kreuz
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Basf Se
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    • 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
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to pyridine compounds of the general 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 dotted line ( ) is a single bond or a double bond
  • R 1 is Ci-C6-alkyl, Ci-C6-haloalkyl, hydroxy-Ci-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C2- C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy-Ci-C6-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-haloal
  • 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-haloalkylcarbonyl-Ci-C6-haloalkyl, Ci- C6-haloalkylcarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-haloalkyl, OH, Ci- C
  • R 2 wherein the cyclic groups of R 2 are unsubstituted or substituted by R a ;
  • A is CR 3 or NR 3A ;
  • Z is a 5 or 6 membered heteroaryl ring comprising A, except imidazolyl and triazolyl;
  • R 3 is halogen, CN, N0 2 , CHO, d-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 3 -C 6 - alkenyl, C3-C6-haloalkenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy, Ci-drhaloal- koxy, 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, C1-C6- haloalkylthio, NH2, (Ci-C6-al
  • R 3A is H, Ci-Ce-alkyl, Ci-C 6 -haloalkyl, d-Ce-alkylcarbonyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C2-C6-alkynyl, C3-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, Ci- C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6- alkyl)a
  • pyridine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, e.g. 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 (III) 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.
  • TBME -butyl methylether
  • dioxane anisole and tetrahydrofuran
  • dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, ⁇ , ⁇ -dimethylformamide (DMF), N,N-dimethyla- cetamide (DMAC), 1 ,3-dimethyl-2-imidazolidinone (DMI), ⁇ , ⁇ '-dimethylpropylene urea (DMPU), dimethyl sulfoxide (DMSO) and 1 -methyl-2 pyrrolidinone (NMP).
  • 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, Fe203, Ag20; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2C03, K2CO3, CS2CO3, MgC03, and CaC03, as well as alkali metal hydrogen carbonates (bicarbonates) such as LiHC03, NaHC03, KHCO3; alkali metal and alkaline earth metal phosphates such as potassium phosphate (K3PO4), calcium phosphate (Ca3(P0 4 )2); alkali metal and alkaline earth metal acetates such as sodium a
  • 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 e.g., palladium based catalysts like, e.g., Palladium(ll)acetate, tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)pal- ladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., 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 pyridines (II) can easily prepared from 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
  • 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.
  • 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.
  • suitable catalysts include e.g., palladium based catalysts like, e.g., Palla- dium(ll)acetate, tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)palla- dium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, triphenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1 ,1 '-binaphthyl).
  • phosphines like, e.g., P(o-tolyl)3, trip
  • the 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, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfox- ide, DMF, DMAC, DMI, ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and 1 -methyl-2 pyrroli- dinone (NMP).
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such
  • 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.
  • catalysts include e.g., palladium based catalysts like, e.g., Pal- ladium(ll)acetate, tetrakis(triphenylphosphine)palladium(0), bis(triphenylphosphine)palla- dium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)ferrocene)-dichloropalladium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., 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
  • the halogenation 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.
  • Suitable in principle are all solvents which are capable of dissolving the pyridines (I) and the reactant NXS at least partly and preferably fully under the reaction conditions.
  • Suitable solvents are ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, DMF, DM AC, DMI, ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and 1 -methyl-2 pyrrolidinone (NMP).
  • ethers such as diethyl ether, diisopropyl ether, TBME, diox- ane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, dimethylsulfoxide, DMF, DM AC, DMI, ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and 1 -methyl-2 pyrrolidinone (NMP).
  • NXS is used preferably from 1 to 10 equivalents based on the pyridine (I), more preferably from 1 .0 to 5.0 equivalents based on the pyridine (I), most preferably from 1 .0 to 2.0 equivalents based on the pyridine (I).
  • 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, e.g. by mixing with water, sepa- ration 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.
  • pyridine compounds of formula (I) as described herein are capable of forming geometrical isomers, e.g. 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 chi- rality 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, more preferably a carboxylic group or sulphonic group, 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 H atoms are replaced by Ci-C4-alkyl, hydroxy-Ci-C4-alkyl, Ci-C4-alkoxy-Ci- C4-alkyl, hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, phenyl or benzyl, preferably ammonium, methyl-ammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, tetrae- thylamm-onium
  • Pyridine compounds of formula (I) as described herein having an acidic functionality preferably a carboxyl group or a sulphonic group
  • an acidic functionality preferably a carboxyl group or a sulphonic group
  • Pyridine compounds of formula (I) as described herein having an acidic functionality can be employed, if applicable, in the form of the acid, in the form of an agriculturally suitable salt with cations as defined above or else in the form of an agriculturally acceptable derivative, e.g. as amides, such as mono- and di-Ci-C6-al- kylamides or arylamides, as esters, e.g.
  • allyl esters propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((tetrahydrofuran-2-yl)methyl) esters and also as thioesters, e.g. as Ci-Cio-alkylthio esters.
  • Preferred mono- and di-Ci-C6-alkylamides are the CH3 and the dimethyl- amides.
  • Preferred arylamides are, e.g., the anilides and the 2-chloroanilides.
  • Preferred alkyl es ters are, e.g., the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), meptyl (1 -methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
  • Preferred Ci-C 4 -alkoxy- Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, e.g.
  • Ci-C 4 -alkyl e.g. CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, CH(CH 3 )-C 2 H 5 , CH 2 -CH(CH 3 ) 2 , and C(CH 3 ) 3 ;
  • Ci-C6-alkyl Ci-C 4 -alkyl as mentioned above, and also, e.g., 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 -dimethyl- butyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl- butyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-trimethylpropyl, 1 ,2,2-trimethylpropyl, 1 -
  • Ci-C 4 -haloalkyl Ci-C 4 -alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, flu- oromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluo romethyl, 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, pentafluoroethy
  • Ci-C6-haloalkyl Ci-C 4 -haloalkyl as mentioned above, and also, e.g., 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, and dodecafluorohexyl;
  • C 3 -C6-cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • C3-C6-haloalkenyl a C3-C6-alkenyl substituent as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g.2-chloroprop-2-en-1-yl, 3-chlo- roprop-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;
  • C3-C6-alkynyl e.g.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,
  • C2-C6-alkynyl C3-C6-alkynyl as mentioned above and also ethynyl;
  • C3-C6-haloalkynyl a C3-C6-alkynyl group as mentioned above which is partially or fully substituted by F, CI, Brand/or I, e.g.1,1-difluoroprop-2-yn-1-yl, 3-chloroprop-2-yn-1-yl, 3-bromo- prop-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-C4-alkoxy e.g. 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, e.g., pentoxy, 1-methylbut- oxy, 2-methylbutoxy, 3-methoxylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dime- thylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbut- oxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trime- thylpropoxy, 1 ,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy, and 1-ethyl-2-methylpropoxy.
  • Ci-C6-haloalkoxy a Ci-C4-haloalkoxy as mentioned above, and also, e.g., 5-fluoro- pentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluoro- hexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
  • Ci-C4-alkylthio e.g. methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1 - methylpropylthio, 2-methylpropylthio, and 1 ,1 -dimethylethylthio;
  • (Ci-C4-alkyl)amino e.g. methylamino, ethylamino, propylamino, 1 -methylethylamino, bu- tylamino, 1 -methylpropylamino, 2-methylpropylamino, or 1 ,1 -dimethylethylamino;
  • (Ci-C6-alkyl)amino (Ci-C4-alkylamino) as mentioned above, and also, e.g., pentylamino, 1 -methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1 -ethyl- propylamino, hexylamino, 1 ,1 -dimethylpropylamino, 1 ,2-dimethylpropylamino, 1 -methylpentyla- mino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1 ,1 -dimethylbutyla- mino, 1 ,2-dimethylbutylamino, 1 ,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dimethyl- butyl-amino 3,3-dimethylbutylamino, 1
  • di(Ci-C4-alkyl)amino e.g. N,N-dimethylamino, ⁇ , ⁇ -diethylamino, N,N-di(1 -meth- ylethyl)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-prop- ylamino, N-methyl-N-(1 -methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1 -methylpropylamino, N-methyl-N-(2-methylpropyl)amino, N-(1
  • di(Ci-C6-alkyl)amino di(Ci-C4-alkyl)amino as mentioned above, and also, e.g., N-me- thyl-N-pentylamino, N-methyl-N-(1 -methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-me- thyl-N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1 -ethylpro- pyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1 ,1 -dimethylpropyl)amino, N-methyl-N-(1 ,2-di- methylpropyl)amino, N-methyl-N-(1 -methylpentyl)amino, N-methyl-N-(2-
  • Ci-C6-alkylsulfonyl (Ci-C6-alkyl-S(0)2-) : e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1 -methylethylsulfonyl, butylsulfonyl, 1 -methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1 ,1 -di- methylethylsulfonyl, pentylsulfonyl, 1 -methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutyl- sulfonyl, 1 ,1 -dimethylpropylsulfonyl, 1 ,2-dimethylpropylsulfonyl, 2,2-dimethylpropyl-sulfonyl, 1 - ethylpropy
  • 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, e.g.
  • heteroaryl a 5- or 6-membered heteroaryl: monocyclic aromatic heteroaryl having 5 to 6 ring members which, in addition to carbon atoms and independent of their position in the ring, 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, e.g. 5-membered aromatic rings like furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g. 2-thienyl, 3-thienyl), pyrrolyl (e.g. pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (e.g.
  • 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.
  • cyclic groups comprises aliphatic cyclic groups such as cycloalkyl, cycloalkenyl and heterocyclyl and aromatic cyclic groups such as heteroaryl and phenyl.
  • pyridine compounds of formula (I) are suitable as herbicides.
  • R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloal- kenyloxy C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkylthio, C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
  • R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
  • R 1 is C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted; also especially preferred 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.
  • Preferred 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-Ci-C6-alkylthio, NH2, Ci-C6-alkylcarbonylamino, Ci-C6-haloalkylcarbonyl- amino, C3-C6-cycloalkylcarbonylamino, phenylcarbonylamino, heterocyclylcarbonylamino, het- eroarylcarbonylamino, (Ci-C6-alkyl)amin
  • R 2 is OH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkynyloxy, Ci-C6-al- kylthio, phenyloxy, Ci-C6-alkylcarbonylamino, Ci-C6-haloalkylcarbonylamino, phenylcarbonylamino, heterocyclylcarbonylamino, heteroarylcarbonylamino, (Ci-C6-alkoxy)amino, (C1-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 OH, C3-C6-alkynyloxy, or Ci-C6-alkoxy
  • R 2 is C3-C6-alkynyloxy
  • R 2 is Ci-C6-alkoxy.
  • Preferred A is CR 3 or NR 3A ;
  • A is CR 3
  • A is NR 3A .
  • Preferred Z is 6-membered heteroaryl ring, preferably triazine, pyrimidine, or pyridine;
  • Z is pyrimidine or pyridine
  • especially preferred Z is pyridine.
  • Z is 5-membered heteroaryl ring, preferably thiadiazole, oxadiazole, triazole, thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thiophene, furan, or pyrrole;
  • Z is thiazole, isothiazole, oxazole, isoxazole, pyrazole, imidazole, thiophene, furan, or pyrrole;
  • especially preferred Z is thiophene, furan, or pyrrole.
  • R 3 is halogen, CHO, CN , d-C 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-Ce-alkoxy; m is 0 or 1 ;
  • X is O, S, or NR 3A ;
  • R 3A is H, Ci-Ce-alkyI, Ci-Ce-haloalkyl, Ci-Ce-alkylcarbonyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloal- kenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl;
  • # denotes the point of attachment to the pyridine ring.
  • pyridine compounds of formula (I), and their use as herbicide wherein R 1 C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
  • R 2 is OH, Ci-Ce-alkoxy
  • R 3 is halogen
  • n 0 or 1 ;
  • R 4 is halogen
  • R 3 is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or C3-C6-cycloal- kyl;
  • R 3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy,
  • R 3 is halogen, CN, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • R 3 is CI, Br, or I
  • R 3 is CI or Br.
  • R 3A is H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkylcarbonyl, C 3 -C 6 -alkenyl, C 3 -C 6 - haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl;
  • R 3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkylcarbonyl;
  • R 3A is H, Ci-C6-alkyl, or Ci-C6-alkylcarbonyl
  • R 3A is H, or Ci-C6-alkyl
  • R 3A is H, or CH3.
  • R 4 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • R 4 is halogen, Ci-C6-haloalkyl, or Ci-C6-alkyl;
  • R 2 is OH or OCH 3 ;
  • Z is pyridine
  • R 3 is halogen
  • pyridine compounds of formula (1.1 ) corresponds to pyridine compounds of formula (I) wherein R 2 is OH
  • their use as herbicide
  • A is CR 3 or NR 3A ; preferably CR 3 ;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy; preferably halogen;
  • pyridine compounds of formula (1.2) corresponds to pyridi pounds of form , and their use as herbicide,
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy; preferably C3-C6-cycloalkyl;
  • A is CR 3 ;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy; preferably halogen;
  • n 0 or 1 ;
  • pyridine compounds of formula (1.3) corresponds to pyridi pounds of form and their use as herbicide
  • dotted line ( ) is a single bond or a double bond
  • A is CR 3 ;
  • pyridine compounds of formula (1.4) corresponds to pyridine compounds of formula (I) wherein R 2 is OCH2C ⁇ CH
  • their use as herbicide are also preferred.
  • A is CR 3 ;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • n 0 or 1 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.4) corresponds to pyridine com- pounds of form 2), and their use as herbicide,
  • dotted line ( ) is a single bond or a double bond
  • n 0 or 1 ;
  • pyridine compounds of formula (1.4) corresponds to pyridine com- pounds of formul , and their use as herbicide,
  • A is CR 3 ;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is pyridine, thiophene, furan, or pyrrol
  • n 0 or 1 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.4) corresponds to pyridine com- pounds of formula (I) wherein R 2 is NHCOCH3), and their use as herbicide,
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 ;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is pyridine, thiophene, furan, or pyrrol
  • n 0 or 1 ;
  • pyridine compounds of formula I.A to I.G corresponds to pyridine compounds of formula (I)
  • X is O, NR 3A , or S.
  • Preferred compounds of formula I, and their use as herbicide are the compounds of the formulae I.A to I.G wherein
  • R 3 is CH 3 , OCH3, CI, Br, CHF 2 , F, or I;
  • R 4 is F or CF 3 .
  • Compound 1 .1.1-3 e.g. comprises the compound of formula 1.1 from Table 1 and line I-3 from Table A.
  • 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, e.g., herbicides from the classes of the acetamides, amides, aryloxyphenoxy- propionates, benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles, isoxazolidinones, nitriles, N- phenylphthalimides, oxadiazoles, oxazolidinediones, oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles, phenylpyrazolines, phenylpyridazines, phosphinic acids, phosphoroamidates, phospho
  • 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, e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria.
  • other crop protection agents e.g. 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 (1.1 ) (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 (1.2) (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 for- mula (1.4) (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 (1.5) (corresponds to pyridine compound of formula (I)), as defined herein; In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.6) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (1.7) (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 1.1 to 1.7, as defined above;
  • compositions according to the present in- vention 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):
  • Mixing partners for the composition can be selected from below herbicides B as defined below: B) herbicides of class b1 ) to b15):
  • 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
  • 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.
  • bilanaphos biases
  • bilanaphos biases
  • bilanaphos- sodium bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium
  • 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, fentra- zamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfen- carbazone 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;
  • 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-oxa- zolidine (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 anhy- dride, 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-(dichloroace- tyl)-1 -oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroace- tyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4) and metcamifen.
  • 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 (http://www.alan- wood.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 Sci- ence 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 sub- stance 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-isoprop- ylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammo- nium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammo- nium, 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-mep- tyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
  • the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1.1 ), especially preferred the compound (1 .1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-1 1 ), (1 .1.1- 17), (1 .1.1-18), (1 .1.1-24), (1 .1.1-25), (1.1.1-31 ), (1.1.1-32), (1 .1.1-38), (1.1.1-39), (1 .1.1-45), or (1 .1.1-46), 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 (1.1 ), especially preferred the compound (1 .1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-1 1 ), (1 .1.1- 17), (1 .1.1-18), (1 .1.1-24), (1 .1.1-25), (1.1.1-31 ), (1.1.1-32), (1
  • the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1.2), especially preferred the compound (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-1 1 ), (1 .2.1- 17), (1 .2.1-18), (1 .2.1-24), (1.2.1-25), (1.2.1-31 ), (1.2.1-32), (1 .2.1-38), (1.2.1-39), (1 .2.1-45), or (1 .2.1-46), 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 (1.2), especially preferred the compound (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-1 1 ), (1 .2.1- 17), (1 .2.1-18), (1 .2.1-24), (1 .2.1-25), (1.2.1-31 ), (1.2.1-32), (1 .2.1-38), (1.2.1-39), (1 .2.1-45), or (1 .2.1-46), 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 (1.2), especially preferred the compound (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-1 1 ), (1 .2.1- 17), (1 .2.1-18), (1 .2.1-24), (1 .2.1-25), (1.2.1-31 ), (1.2.1-32), (1 .2.1-38), (1.2.1-39), (1 .2.1-45), or (1 .2.1-46), 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 (1.2), especially preferred the compound (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-1 1 ), (1 .2.1- 17), (1 .2.1-18), (1 .2.1-24), (1 .2.1-25), (1.2.1-31 ), (1.2.1-32), (1 .2.1-38), (1.2.1-39), (1 .2.1-45), or (1 .2.1-46), 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 (1.2), especially preferred the compound (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-1 1 ), (1 .2.1- 17), (1 .2.1-18), (1 .2.1-24), (1 .2.1-25), (1.2.1-31 ), (1.2.1-32), (1 .2.1-38), (1.2.1-39), (1 .2.1-45), or (1 .2.1-46), 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 (1.2), especially preferred the compound (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-1 1 ), (1 .2.1- 17), (1 .2.1-18), (1 .2.1-24), (1 .2.1-25), (1.2.1-31 ), (1.2.1-32), (1 .2.1-38
  • the composition comprises as component A at least one, preferably exactly pyridine compound of formula (I), preferably of formula (1 .2), especially preferred the compound (1.2.1-3), (1.2.1-4), (1.2.1-10), (1 .2.1-1 1 ), (1 .2.1-17), (1 .2.1-18), (1 .2.1-24), (1.2.1-25), (1 .2.1-31 ), (1 .2.1-32), (1.2.1-38), (1 .2.1-39), (1 .2.1-45), or (1.2.1-46), 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 .2), especially preferred the compound (1.2.1-3), (1.2.1-4), (1.2.1-10), (1 .2.1-1 1 ), (1 .2.1-17), (1 .2.1-18), (1 .2.1-24), (1.2.1-25), (1 .2.1-31 ), (1 .2.1-32), (1.2.
  • the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1.2), especially preferred the compound (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-1 1 ), (1 .2.1- 17), (1 .2.1-18), (1 .2.1-24), (1 .2.1-25), (1.2.1-31 ), (1.2.1-32), (1 .2.1-38), (1.2.1-39), (1 .2.1-45), or (1 .2.1-46), 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 (1.2), especially preferred the compound (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-1 1 ), (1 .2.1- 17), (1 .2.1-18), (1 .2.1-24), (1 .2.1-25), (1.2.1-31 ), (1.2.1-32), (1 .2.1
  • the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1.5), especially preferred the compound (1 .5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-1 1 ), (1 .5.1- 17), (1 .5.1-18), (1 .5.1-24), (1 .5.1-25), (1.5.1-31 ), (1.5.1-32), (1 .5.1-38), (1.5.1-39), (1 .5.1-45), or (1 .5.1-46), 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 (1.5), especially preferred the compound (1 .5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-1 1 ), (1 .5.1- 17), (1 .5.1-18), (1 .5.1-24), (1 .5.1-25), (1.5.1-31 ), (1.5.1-32), (1 .5.1-38), (1.5.1-39), (1 .5.1-45), or (1 .5.1-46), 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 (1.5), especially preferred the compound (1 .5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-1 1 ), (1 .5.1- 17), (1 .5.1-18), (1 .5.1-24), (1 .5.1-25), (1.5.1-31 ), (1.5.1-32), (1 .5.1-38), (1.5.1-39), (1 .5.1-45), or (1 .5.1-46), and at least three, preferably exactly three, herbicides B different from each other.
  • 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, cyhalo- fop-butyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, metamifop, pinoxaden, profoxydim, sethox- ydim, tepraloxydim, tralkoxydim, esprocarb, ethofumesate, molinate, prosulfocarb, thiobencarb and triallate.
  • 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, flupyr- sulfuron-methyl-sodium, foramsulfuron, imazamox, imazamox-ammonium, imazapic, imazapic- ammonium, imazapic-isopropylammonium, imazapyr, imazapyr-ammonium, imazethapyr-iso- propylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-ammonium, imazethapyr-isopropylammonium, imazosulfuron, iodosulfuron-methyl-s
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting (1.1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-11), (1.1.1-17), (1.1.1-18), (1.1.1-24), (1.1.1-25), (1.1.1-31), (1.1.1-32), (1.1.1-38), (1.1.1-39), (1.1.1-45), (1.1.1-46), (1.2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-11), (1.2.1-17), (1.2.1-18), (1.2.1-24), (1.2.1-25), (1.2.1-31), (1.2.1-32), (1.2.1-38), (1.2.1-39), (1.2.1-45), (1.2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-11), (1.5.1-17), (1.5.1-18), (1.5.1-24), (1.5.1-25), (1.5.1-31 ), (1.5.1-32), (1.5.1-38), (1.5.1-39), (1.5.1-39), (1.5.1-4
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-11), (1.1.1-17), (1.1.1-18), (1.1.1-24), (1.1.1-25), (1.1.1-31), (1.1.1-32), (1.1.1-38), (1.1.1-39), (1.1.1-45), (1.1.1-46), (1.2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-11), (1.2.1-17), (1.2.1-18), (1.2.1-24), (1.2.1-25), (1.2.1-31), (1.2.1-32), (1.2.1-38), (1.2.1-39), (1.2.1-45), (1.2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-11), (1.5.1-17), (1.5.1-18), (1.5.1-24), (1.5.1-25), (1.5.1-31 ), (1.5.1-32), (1.5.1-38), (1.5.1-39), (I), (I), (1.5.
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-11), (1.1.1-17), (1.1.1-18), (1.1.1-24), (1.1.1-25), (1.1.1-31), (1.1.1-32), (1.1.1-38), (1.1.1-39), (1.1.1-45), (1.1.1-46), (1.2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-11), (1.2.1-17), (1.2.1-18), (1.2.1-24), (1.2.1-25), (1.2.1-31), (1.2.1-32), (1.2.1-38), (1.2.1-39), (1.2.1-45), (1.2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-11), (1.5.1-17), (1.5.1-18), (1.5.1-24), (1.5.1-25), (1.5.1-31 ), (1.5.1-32), (1.5.1-38), (1.5.1-39), (I), (I), (1.5.
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-11), (1.1.1-17), (1.1.1-18), (1.1.1-24), (1.1.1-25), (1.1.1-31), (1.1.1-32), (1.1.1-38), (1.1.1-39), (1.1.1-45), (1.1.1-46), (1.2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-11), (1.2.1-17), (1.2.1-18), (1.2.1-24), (1.2.1-25), (1.2.1-31), (1.2.1-32), (1.2.1-38), (1.2.1-39), (1.2.1-45), (1.2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-11), (1.5.1-17), (1.5.1-18), (1.5.1-24), (1.5.1-25), (1.5.1-31 ), (1.5.1-32), (1.5.1-38), (1.5.1-39), (I), (I), (1.5.
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-11), (1.1.1-17), (1.1.1-18), (1.1.1-24), (1.1.1-25), (1.1.1-31), (1.1.1-32), (1.1.1-38), (1.1.1-39), (1.1.1-45), (1.1.1-46), (1.2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-11), (1.2.1-17), (1.2.1-18), (1.2.1-24), (1.2.1-25), (1.2.1-31), (1.2.1-32), (1.2.1-38), (1.2.1-39), (1.2.1-45), (1.2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-11), (1.5.1-17), (1.5.1-18), (1.5.1-24), (1.5.1-25), (1.5.1-31 ), (1.5.1-32), (1.5.1-38), (1.5.1-39), (I), (I), (1.5.
  • compositions comprising in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-11), (1.1.1-17), (1.1.1-18), (1.1.1-24), (1.1.1-25), (1.1.1-31), (1.1.1-32), (1.1.1-38), (1.1.1-39), (1.1.1-45), (1.1.1-46), (1.2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-11), (1.2.1-17), (1.2.1-18), (1.2.1-24), (1.2.1-25), (1.2.1-31), (1.2.1-32), (1.2.1-38), (1.2.1-39), (1.2.1-45), (1.2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-11), (1.5.1-17), (1.5.1-18), (1.5.1-24), (1.5.1-25), (1.5.1-31), (1.5.1-32), (1.5.1-38), (1.5.1-39), (1.5.1-4), (1.5.1-10),
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-11), (1.1.1-17), (1.1.1-18), (1.1.1-24), (1.1.1-25), (1.1.1-31), (1.1.1-32), (1.1.1-38), (1.1.1-39), (1.1.1-45), (1.1.1-46), (1.2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-11), (1.2.1-17), (1.2.1-18), (1.2.1-24), (1.2.1-25), (1.2.1-31), (1.2.1-32), (1.2.1-38), (1.2.1-39), (1.2.1-45), (1.2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-11), (1.5.1-17), (1.5.1-18), (1.5.1-24), (1.5.1-25), (1.5.1-31 ), (1.5.1-32), (1.5.1-38), (1.5.1-39), (I), (I), (1.5.
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.1.1-3), (1.1.1-4), (1.1.1-10), (1.1.1-11), (1.1.1-17), (1.1.1-18), (1.1.1-24), (1.1.1-25), (1.1.1-31), (1.1.1-32), (1.1.1-38), (1.1.1-39), (1.1.1-45), (1.1.1-46), (1.2.1-3), (1.2.1-4), (1.2.1-10), (1.2.1-11), (1.2.1-17), (1.2.1-18), (1.2.1-24), (1.2.1-25), (1.2.1-31), (1.2.1-32), (1.2.1-38), (1.2.1-39), (1.2.1-45), (1.2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-11), (1.5.1-17), (1.5.1-18), (1.5.1-24), (1.5.1-25), (1.5.1-31 ), (1.5.1-32), (1.5.1-38), (1.5.1-39), (I), (I), (1.5.
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1 .1.1-3), (1.1.1-4), (1.1.1-10), (1 .1.1-1 1 ), (1.1.1-17), (1 .1.1-18), (1 .1.1-24), (1.1.1-25), (1 .1.1-31 ), (1 .1.1-32), (1.1.1-38), (1 .1.1-39), (1 .1.1-45), (1.1.1-46), (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1 .2.1-1 1 ), (1 .2.1-17), (1.2.1-18), (1 .2.1-24), (1 .2.1-25), (1.2.1-31 ), (1 .2.1-32), (1 .2.1-38), (1.2.1-39), (1 .2.1-45), (1 .2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-1 1 ), (1 .5.1-17), (1 .5.1-18), (1.5.1-24), (1 .5.1
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1 .1.1-3), (1.1.1-4), (1.1.1-10), (1 .1.1-1 1 ), (1.1.1-17), (1 .1.1-18), (1 .1.1-24), (1.1.1-25), (1 .1.1-31 ), (1 .1.1-32), (1.1.1-38), (1 .1.1-39), (1 .1.1-45), (1.1.1-46), (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1 .2.1-1 1 ), (1 .2.1-17), (1.2.1-18), (1 .2.1-24), (1 .2.1-25), (1 .2.1-31 ), (1 .2.1-32), (1 .2.1-38), (1.2.1-39), (1 .2.1-45), (1 .2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-1 1 ), (1 .5.1-17), (1 .5.1-18), (1.5.1-24), (1 .
  • the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1 .1.1-3), (1.1.1-4), (1.1.1-10), (1 .1.1-1 1 ), (1.1.1-17), (1 .1.1-18), (1 .1.1-24), (1.1.1-25), (1 .1.1-31 ), (1 .1.1-32), (1.1.1-38), (1 .1.1-39), (1 .1.1-45), (1.1.1-46), (1 .2.1-3), (1.2.1-4), (1.2.1-10), (1 .2.1-1 1 ), (1 .2.1-17), (1.2.1-18), (1 .2.1-24), (1 .2.1-25), (1.2.1-31 ), (1 .2.1-32), (1 .2.1-38), (1.2.1-39), (1 .2.1-45), (1 .2.1-46), (1.5.1-3), (1.5.1-4), (1.5.1-10), (1.5.1-1 1 ), (1 .5.1-17), (1 .5.1-18), (1.5.1-24), (1 .5.1
  • binary compositions includes compositions comprising one or more, e.g. 1 , 2 or 3, active compounds of the formula (I) and either one or more, e.g. 1 , 2 or 3, herbicides B or one or more safeners C.
  • ternary compositions includes compositions comprising one or more, e.g. 1 , 2 or 3, active compounds of the formula (I), one or more, e.g. 1 , 2 or 3, herbicides B and one or more, e.g. 1 , 2 or 3, safeners 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 .
  • 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; especially preferred comprising as only herbicidal active compounds 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 (1.1.1-3) and the substance(s) as defined in the respective row of table T:

Abstract

La présente invention concerne des composés de pyridines de formule (I), ou leurs sels ou dérivés acceptables sur le plan agricole, les variables étant définies selon la description, l'utilisation des composés de pyridine de formule (I) comme herbicide, des compositions les contenant et leur utilisation en tant qu'herbicides, c'est-à-dire pour lutter contre les plantes nuisibles, et également un procédé pour lutter contre la végétation indésirable qui consiste à laisser agir une quantité d'herbicide efficace d'au moins un composé de pyridine de formule (I) sur les plantes, leurs graines et/ou leur habitat.
PCT/EP2017/068651 2016-07-28 2017-07-24 Composés de pyridine herbicides WO2018019770A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10863743B2 (en) 2016-07-29 2020-12-15 Basf Se Method for controlling PPO resistant weeds
WO2021180919A1 (fr) 2020-03-13 2021-09-16 Softhale Nv Méthode de traitement d'une maladie, d'un trouble ou d'un état respiratoire provenant d'une infection virale
US11185075B2 (en) 2016-12-16 2021-11-30 Basf Se Herbicidal phenyltriazolinones
US11292784B2 (en) 2017-11-27 2022-04-05 Basf Se Crystalline forms of ethyl 2-[[3-[[3- chloro-5-fluoro-6-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]-2-pyridyl]oxy] acetate

Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4936905A (en) * 1986-05-09 1990-06-26 Monsanto Company Substituted 2,6-substituted pyridine compounds having herbicidal activity
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
WO2006024820A1 (fr) 2004-09-03 2006-03-09 Syngenta Limited Dérivés d'isoxazoline et leur utilisation comme herbicides
WO2006037945A1 (fr) 2004-10-05 2006-04-13 Syngenta Limited Derives d’isoxazoline et leur utilisation comme herbicides
WO2006099972A1 (fr) 2005-03-23 2006-09-28 F. Hoffmann-La Roche Ag Derives d'acetylenyl-pyrazolo-pyrimidine comme antagonistes mglur2
WO2007071900A1 (fr) 2005-12-21 2007-06-28 Syngenta Limited Nouveaux herbicides
WO2007096576A1 (fr) 2006-02-27 2007-08-30 Syngenta Limited Isoxazolines herbicides
WO2009099080A1 (fr) 2008-02-06 2009-08-13 Daiichi Sankyo Company, Limited Nouveau dérivé de phénylpyrrole
WO2011100769A2 (fr) 2010-02-15 2011-08-18 Synovo Gmbh Modulateurs de kinase pour le traitement du cancer
WO2013104561A1 (fr) * 2012-01-12 2013-07-18 Basf Se Isoxazolo[5,4-b]pyridines

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0451878A1 (fr) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modification de plantes par techniques de génie génétique pour combattre ou contrôler les insectes
US4936905A (en) * 1986-05-09 1990-06-26 Monsanto Company Substituted 2,6-substituted pyridine compounds having herbicidal activity
EP0374753A2 (fr) 1988-12-19 1990-06-27 American Cyanamid Company Toxines insecticides, gènes les codant, anticorps les liant, ainsi que cellules végétales et plantes transgéniques exprimant ces toxines
EP0392225A2 (fr) 1989-03-24 1990-10-17 Ciba-Geigy Ag Plantes transgéniques résistantes aux maladies
EP0427529A1 (fr) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Lectines larvicides, et résistance induite des plantes aux insectes
WO1993007278A1 (fr) 1991-10-04 1993-04-15 Ciba-Geigy Ag Sequence d'adn synthetique ayant une action insecticide accrue dans le mais
WO1995034656A1 (fr) 1994-06-10 1995-12-21 Ciba-Geigy Ag Nouveaux genes du bacillus thuringiensis codant pour des toxines actives contre les lepidopteres
WO2002015701A2 (fr) 2000-08-25 2002-02-28 Syngenta Participations Ag Nouvelles toxines insecticides derivees de proteines cristallines insecticides de $i(bacillus thuringiensis)
WO2003018810A2 (fr) 2001-08-31 2003-03-06 Syngenta Participations Ag Toxines cry3a modifiees et sequences d'acides nucleiques les codant
WO2003052073A2 (fr) 2001-12-17 2003-06-26 Syngenta Participations Ag Nouvel evenement du mais
WO2006024820A1 (fr) 2004-09-03 2006-03-09 Syngenta Limited Dérivés d'isoxazoline et leur utilisation comme herbicides
WO2006037945A1 (fr) 2004-10-05 2006-04-13 Syngenta Limited Derives d’isoxazoline et leur utilisation comme herbicides
WO2006099972A1 (fr) 2005-03-23 2006-09-28 F. Hoffmann-La Roche Ag Derives d'acetylenyl-pyrazolo-pyrimidine comme antagonistes mglur2
WO2007071900A1 (fr) 2005-12-21 2007-06-28 Syngenta Limited Nouveaux herbicides
WO2007096576A1 (fr) 2006-02-27 2007-08-30 Syngenta Limited Isoxazolines herbicides
WO2009099080A1 (fr) 2008-02-06 2009-08-13 Daiichi Sankyo Company, Limited Nouveau dérivé de phénylpyrrole
WO2011100769A2 (fr) 2010-02-15 2011-08-18 Synovo Gmbh Modulateurs de kinase pour le traitement du cancer
WO2013104561A1 (fr) * 2012-01-12 2013-07-18 Basf Se Isoxazolo[5,4-b]pyridines

Non-Patent Citations (67)

* Cited by examiner, † Cited by third party
Title
"Farm Chemicals Handbook", vol. 86, 2000, MEISTER PUBLISHING COMPANY
"Technical Monograph", May 2008, CROPLIFE INTERNATIONAL
ARNAB, P., ANGEW. CHEM. INT. ED., vol. 49, 2010, pages 1492 - 1495
ARNAB, P.: "Angew. Chem. Int. Ed.", vol. 49, 2010, pages: 1492 - 1495
B. HOCK; C. FEDTKE; R. R. SCHMIDT: "Herbizide [Herbicides", 1995, GEORG THIEME VERLAG
CHEM. EUR. J., vol. 18, 2012, pages 2498 - 2502
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1033757-93-5
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1033760-55-2
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1033760-58-5
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1300118-96-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1304113-05-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1312337-45-3
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1312337-48-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1312337-51-1
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1312337-72-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1312340-82-1
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1312340-83-2
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1312340-84-3
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1361139-71-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1390661-72-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1486617-21-3
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1629965-65-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1637453-94-1
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1637455-12-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1654057-29-0
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1654744-66-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1654747-80-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1701416-69-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1708087-22-2
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 175899-01-1
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 180608-33-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 1844836-64-1
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 2023785-78-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 2023785-79-5
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 2023785-80-8
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 212754-02-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 353292-31-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 403640-27-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 420138-01-8
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 420138-40-5
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 420138-41-6
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 451484-50-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 452098-92-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 452099-05-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 452100-03-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 499223-49-3
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 52836-31-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 54091-06-4
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 71526-07-3
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 81777-95-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 81778-66-7
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 915396-43-9
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 943832-60-8
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 948893-00-3
J. MED. CHEM., vol. 43, 2000, pages 4288 - 4312
J. MED. CHEM., vol. 55, 2012, pages 10584 - 10600
K. K. HATZIOS: "Herbicide Handbook", 1998, WEED SCIENCE SOCIETY OF AMERICA
KAMEI ET AL., TETRAHEDRON LETT., vol. 55, 2014, pages 4245 - 4247
KNOWLES, ADJUVANTS: "Agrow Reports DS256", 2006, T&F INFORMA
KNOWLES: "Agrow Reports DS243", 2005, T&F INFORMA, article "New developments in crop protection product formulation"
KUHN, B., J. MED. CHEM., vol. 53, 2010, pages 2601 - 2611
MCCUTCHEON'S: "Emulsifiers & Detergents", vol. 1, 2008, MCCUTCHEON'S DIRECTORIES
MOLLET; GRUBEMANN: "Formulation technology", 2001, WILEY VCH
ORG. LETT., vol. 16, 2014, pages 5466 - 5469
SILVESTRI, M. A., J. MED. CHEM., vol. 47, 2004, pages 3149 - 3162
THE COMPENDIUM OF PESTICIDE COMMON NAMES, Retrieved from the Internet <URL:http://www.alan- wood.net/pesticides>
W. H. AHRENS: "Herbicide Handbook", 1994

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* Cited by examiner, † Cited by third party
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