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WO2018019755A1 - Composés herbicides de pyridine - Google Patents

Composés herbicides de pyridine Download PDF

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Publication number
WO2018019755A1
WO2018019755A1 PCT/EP2017/068599 EP2017068599W WO2018019755A1 WO 2018019755 A1 WO2018019755 A1 WO 2018019755A1 EP 2017068599 W EP2017068599 W EP 2017068599W WO 2018019755 A1 WO2018019755 A1 WO 2018019755A1
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Prior art keywords
alkyl
haloalkyl
cycloalkyl
alkoxy
methyl
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PCT/EP2017/068599
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English (en)
Inventor
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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Publication of WO2018019755A1 publication Critical patent/WO2018019755A1/fr

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    • 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
    • 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
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    • 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
    • C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D213/61—Halogen atoms or nitro radicals
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    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/65—One oxygen atom attached in position 3 or 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4
    • C—CHEMISTRY; METALLURGY
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    • 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
    • C07D401/14—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 three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
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    • 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
    • C07D405/14—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 three or more hetero rings
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    • 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
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    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

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 present invention provides the pyridine compounds of formula (I)
  • 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 d-Ce-alkyl, C C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, Ci-C 6 -alkoxy-C 2 -C 6 - alkenyl, Ci-C6-alkoxy-C2-C6-haloalkenyl, Ci-C6-haloalkoxy-C2-C6-alkenyl, Ci-C6-haloal- koxy-C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy-C2-C6-alkynyl, Ci- C6-alkoxy-C2-C6-alkynyl, Ci- C6-alkoxy-C3-C6-haloalkynyl, Ci-C6-haloalkoxy-C2-C6-alkynyl, Ci-C
  • cyclic groups of R 2 are unsubstituted or substituted by R c ;
  • acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R b is d-Ce-alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 - haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-halocy- cloalkenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-alkyl, Ci C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-haloalkyl, C1-C6- alkylcarbonyl, Ci-C6-
  • R c is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or d-Ce- haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, or d-Gralkylsulfonyl;
  • R d is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; ⁇
  • R d is unsubstituted or substituted by R e ;
  • R e is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci-Ce- haloalkoxy, Ci-C6-alkylsulfonyl;
  • A is CR 3 or NR 3A ;
  • Z is a 5 or 6 membered heteroaryl ring comprising A
  • R 3 is halogen, CN, N0 2 , CHO, Ci-C 6 -alkyl, Ci-Ce-haloalkyl, d-Ce-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, d-dr haloalkylthio, NH 2 , (Ci-C 6 -al
  • R 3A is H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-d-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, d-d- haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, Ci-
  • Ci-C6-alkylthio Ci-C6-haloalkylthio, NH 2 , (Ci-C6-alkyl)amino, di(d-d- alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C 3 -C6-cycloalkyl, (d-d-cycloal- kyl)oxy, or phenyl;
  • R 4 is halogen, CN, N0 2 , CHO, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkylcarbonyl, d-d- alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, Ci-C6-alkoxy, Ci-d-haloal- koxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-d- haloalkylthio, NH 2 , (Ci-C6-alkyl)amino, di(C
  • R a is halogen, CN, NO2, Ci-d-alkyl, Ci-d-haloalkyl, Ci-d-alkoxy, or d-Ce-haloalkoxy; m is 0, 1 , 2, or 3;
  • the present invention also provides use of the pyridine compounds of formula (I) as described herein including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, as herbicide.
  • pyridine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, e.g. by the following processes:
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tet- rahydrofuran (THF), and also dimethyl sulfoxide (DMSO), dimethylformamide (DMF) and dime- thylacetamide (DMAC), particularly preferably diethyl ether, dioxane and THF.
  • ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tet- rahydrofuran (THF
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as lithium hydride (LiH), sodium hydride (NaH), potassium hydride (KH) and calcium hydride (CaH), alkali metal amides, such as lithium hexamethyidisilazide (LHMDS) and lithium diisopropylamide (LDA), organometallic compounds, in particular alkali metal alkyls, such as methyllithium (MeLi), butyllithium (BuLi) and phenyllithium (PhLi), and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide (NaOCHs), sodium ethoxide (NaOC2H5), potassium ethoxide (KOC2H5), potassium tert-butoxide ( BuOK), potassium tert- pentoxide and dimethoxymagnesium, moreover organic
  • tertiary amines such as tri- methylamine (TMA), triethylamine (TEA), diisopropylethylamine (DI PEA) and N-methylpiperi- dine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to NaH, LHMDS and lithium diisopropyla- mide (LDA).
  • TMA tri- methylamine
  • TEA triethylamine
  • DI PEA diisopropylethylamine
  • LDA lithium diisopropyla- mide
  • the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile, based on the pyridine com- pounds (I).
  • the olefin IV can be obtained by elimination of the alcohol (analogous procedures e.g. Synlett, (5), 561-562; 1997; Journal of Organic Chemistry, 48(15), 2622-5; 1983):
  • the elimination of the alcohol of the pyridine (II) is usually carried out at temperatures from -100 °C to the boiling point of the reaction mixture, preferably from 0 °C to 120 °C, particularly preferably from 20 °C to 100 °C, in an inert solvent optionally in the presence of an acid.
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably toluene and o-xylene.
  • aromatic hydrocarbons such as toluene, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably toluene and o-xylene.
  • Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid; organic acids p-toluenesul- fonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methanesulfonic acid, acetic acid; preferably p-toluenesulfonic acid and HCI.
  • the acids are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the diol (V) can be obtained e.g. by dihydroxylation of the olefin (IV) (analogous procedures e.g. Journal of Inorganic Biochemistry, 105(4), 509-517; 201 1 ):
  • the oxidation of the olefin (IV) to the diol (V) is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from 0 °C to 120 °C, particularly preferably from 20 °C to 100 °C, in an inert solvent.
  • the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (IV) with the oxidant in an organic solvent.
  • Suitable in principle are all solvents which are capable of dissolving the pyridines (IV) and the oxidant at least partly and preferably fully under the reaction conditions.
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably TBME, THF It is also possible to use mixtures of the solvents mentioned.
  • Suitable oxidants are e.g. potassium permanganate, potassium perruthenate, osmium tetrox- ide and other osmium salts, like potassium osmate.
  • the oxidant can be used in equimolar amounts or in catalytic amounts together with a reoxidant like N-methylmorpholine-N-oxide or potassium hexacyanoferrate in stochiometric amounts or in excess.
  • Pyridine compounds (VI), with R equals alkyl, haloalkyl, alkoxy, haloalkoxy, can be obtained by reacting respective pyridine compounds of formula (VII) with base and an electrophile (VIII) (analogous procedures e.g. Journal of the American Chemical Society, 132(31 ), 10706-10716; 2010).
  • Electrophile (VIII) can be an alkyl-, alkenyl- or alkynyl-halide, e.g. methyl iodide, allyl bromide or propargyl bromide, or a halogenating agent, e.g.
  • the reaction of the pyridine (VII) with the electrophile is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 80 °C, particularly preferably from -80 °C to 30 °C, in an inert organic solvent in the presence of a base.
  • Suitable in principle are all solvents which are capable of dissolving the pyridine (VII) and the electrophile (VIII) 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
  • anisole and THF nitriles such as acetonitrile and propionitrile
  • dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2-imidaz- olidinone (DMI), ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and NMP.
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LDA, LHMDS, lithium 2,2,6,6-tetramethylpiperidide (LTMP), organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkox- ides, such as NaOCH 3 , NaOC2H 5 , KOC2H5, tBuOK, potassium tert-pentoxide and dimethox- ymagnesium, moreover organic bases, e.g.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LDA, LHMDS, lithium 2,2,6,6-tetramethylpiperidide (LTMP
  • tertiary amines such as TMA, TEA, DIPEA and N- methylpiperidine
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethyla- minpyridine, and also bicyclic amines.
  • Particular preference is given to NaH, LTMP and LDA.
  • the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile (VIII), based on the pyridine (VII).
  • the reaction of the pyridine (I) with the electrophile is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 80 °C, particularly preferably from -80 °C to 30 °C, in an inert organic solvent in the presence of a base.
  • Suitable in principle are all solvents which are capable of dissolving the pyridine (I) and the electrophile (IX) 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, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2Hs, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth
  • tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
  • Particular preference is given to NaH, lithium hexamethyldisilazide and LDA.
  • the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile (IX), based on the pyridine
  • the pyridines of formula (X) can be obtained by reacting respective pyridines of formula (XI) with boronic acids/esters of formula (XII):
  • reaction of pyridines (XI) with boronic acids/esters (XII) 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 (XI) with the boronic acids/esters (XII) in an organic solvent with or without water as co-solvent. Suitable in principle are all solvents which are capable of dissolving the pyridines (XI) and the boronic acids (XII) 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, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP
  • suitable metal-containing bases are inorganic compounds including metal-containing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydrox- ides, 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
  • 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 (XI), more preferably from 1.0 to 5.0 equivalents based on the pyridine (XI), most preferably from 1.2 to 2.5 equivalents based on the pyridine (XI).
  • the reaction of the pyridines (XI) with the boronic acids/esters (XII) 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(O), 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 (XI).
  • halopyridines are known from the literature (e.g. WO2015181747; WO2014055548) are commercially available or can be prepared by known procedures.
  • boronic acids/esters (XII) required for the preparation of pyridines of formula (X) 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 of formula (XIII) can be obtained by reacting respective pyridines of formula (X) with a reducing agent such as LAH or DIBAIH.
  • the reduction of pyridines (X) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably from -20 °C to 60 °C, particularly preferably from 0 °C to 25 °C, in an inert organic solvent.
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably diethyl ether, dioxane and THF.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes
  • aromatic hydrocarbons such as toluene, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, ani
  • Examples of reducing agents for pyridines (X) include LAH, DIBALH, LiBH 4 or Lithium triethyl- borohydride.
  • Preferred agents include LAH and DIBALH.
  • the hydride-source is used preferably from 1 to 10 equivalents based on the pyridine (X), more preferably from 1.0 to 5.0 equivalents based on the pyridine (X), most preferably from 1 .2 to 2.5 equivalents based on the pyridine (X).
  • the reaction of pyridines (X) with a metal organic species is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably from -20 °C to 60 °C, particularly preferably from -20 °C to 25 °C, in an inert organic solvent.
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably diethyl ether, dioxane and THF.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes
  • aromatic hydrocarbons such as toluene, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
  • metal organic species for the synthesis of pyridines are Grignard reagents like R'MgCI, R'MgBr or R'Mgl, lithium organic species, aluminum organic species like R'sAI, R' 2 AIX and R'AIX 2 , titanium organic species like R' 4 Ti, R' 3 TiX, R' 2 TiX 2 and RTiX 3 ,
  • Preferred agents include Grignard reagents and lithium organic species.
  • the metal organic species is used preferably from 2 to 10 equivalents based on the pyridine (X), more preferably from 2.0 to 5.0 equivalents based on the pyridine (X), most preferably from 2.0 to 3.0 equivalents based on the pyridine (X).
  • the reaction of pyridines (XVI) with a metal organic species is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably from -20 °C to 60 °C, particularly preferably from -20 °C to 25 °C, in an inert organic solvent.
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Ce-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably diethyl ether, dioxane and THF.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Ce-alkanes
  • aromatic hydrocarbons such as toluene, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
  • metal organic species for the synthesis of pyridines are Grignard reagents like R'MgCI, R'MgBr or R'Mgl, lithium organic species, aluminum organic species like R'sAI, R' 2 AIX and R'AIX 2 , titanium organic species like R' 4 Ti, R' 3 TiX, R' 2 TiX 2 and RTiX 3 ,
  • Preferred agents include Grignard reagents and lithium organic species.
  • the metal organic species is used preferably from 2 to 10 equivalents based on the pyridine (XVI), more preferably from 2.0 to 5.0 equivalents based on the pyridine (XVI), most preferably from 2.0 to 3.0 equivalents based on the pyridine (XVI).
  • the pyridines of formula (XVI) can be obtained by oxidizing respective pyridines of formula (XIII).
  • the oxidation of pyridines (XIII) is usually carried out from - 80 °C to the boiling point of the reaction mixture, preferably from -20 °C to 100 °C, particularly preferably from 0 °C to 75 °C, in an inert organic solvent.
  • the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (XIII) in an organic solvent.
  • Suitable in principle are all solvents which are capable of dissolving the pyridines (XIII) at least partly and preferably fully under the reaction conditions.
  • solvents examples include aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as CH 2 CI 2 , CHC , CCH 2 CICH 2 CI or CCI 4 , ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP. It is also possible to use mixtures of the solvents mentioned.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • halogenated hydrocarbons such as CH 2 CI 2 , CHC , CCH 2 CICH 2 CI or CCI 4
  • oxidizing agents for the synthesis of pyridines are metal oxides such as ⁇ 2, ⁇ 4, CrC or PCC, and non-metal oxides such as NaCIO, Nal0 4 or pyridine/SC>3 - complex.
  • metal oxides such as ⁇ 2, ⁇ 4, CrC or PCC
  • non-metal oxides such as NaCIO, Nal0 4 or pyridine/SC>3 - complex.
  • Swern oxidation or the TEMPO oxidation known to a per- son skilled in the art can be used to obtain pyridines of formula (XVI).
  • Preferred agents include ⁇ 2, KMn0 4 and PCC, more preferred MnC>2.
  • the oxidizing agent is used preferably from 1 to 50 equivalents based on the pyridine (XIII), more preferably from 1.0 to 20.0 equivalents based on the pyridine (XIII), most preferably from 1.0 to 10.0 equivalents based on the pyridine (XIII).
  • Electrophiles can be an alkyl-, alkenyl- or alkynyl-halide, e.g. methyl iodide, allyl bromide pro- pargyl bromide, ethyl iodide, propyl bromide, or ethyl 2-bromoacetate.
  • the reaction of the pyridine (XVIII) with the electrophile is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -20 °C to 100 °C, particularly preferably from -0 °C to 30 °C, in an inert organic solvent in the presence of a base.
  • Suitable in principle are all solvents which are capable of dissolving the pyridine (XVIII) and the electrophile 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, TBME, di- oxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • nitriles such as acetonitrile and propionitrile
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2Hs, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth
  • tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
  • Particular pref- erence is given to NaH, lithium hexamethyldisilazide and LDA.
  • the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the pyridines of formula (I) can be obtained by reacting respective pyridines of formula (XIX), obtained e.g. in analogy to Synlett, (5), 808-810, 2002, with boronic acids/esters of formula (X).
  • reaction of pyridines (XIX) with boronic acids/esters (XX) 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.
  • reaction may in principle be carried out in substance. However, preference is given to re- acting the pyridines (XIX) with the boronic acids/esters (XX) in an organic solvent with or without water as co-solvent.
  • Suitable in principle are all solvents which are capable of dissolving the pyridines (XIX) and the boronic acids (XX) 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, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP
  • suitable metal-containing bases are inorganic compounds including metal-con- taining 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.
  • 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 (XIX), more preferably from 1 .0 to 5.0 equivalents based on the pyridine (XIX), most preferably from 1.2 to 2.5 equivalents based on the pyridine (XIX).
  • a catalyst examples include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), 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).
  • palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(triphenylpho
  • the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyridine (XIX). ⁇ ⁇
  • reaction mixtures are worked up in a customary manner, e.g. 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.
  • boronic acids/esters (XX) required for the preparation of pyridines 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 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.
  • 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 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, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxy- eth-1 -oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hydroxy-ethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltri- methylammonium, benzyltriethylammonium, ⁇ , ⁇ , ⁇ -trimethylethanolammonium (choline salt), furthermore phosphon-ium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as tri- methylsulfonium,
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, hydrogen- sulfate, methylsulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and also the anions of Ci-C4-al- kanoic 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 as men- tioned above or else in the form of an agriculturally acceptable derivative, e.g. as amides, such as mono- and di-Ci-C6-alkylamides or arylamides, as esters, e.g. as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, tefuryl ((THF-2-yl)methyl) esters and also as thioe- sters, e.g.
  • amides such as mono- and di-Ci-C6-alkylamides or arylamides
  • esters e.g. as allyl esters, propargyl esters, Ci-Cio-alkyl esters, alkoxyalkyl esters, t
  • Ci-Cio-alkylthio esters Preferred mono- and di-Ci-C6-alkylamides are the CH3 and the dimethylamides.
  • Preferred arylamides are, e.g., the anilides and the 2-chloroanilides.
  • Pre- ferred alkyl esters are, e.g., the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl
  • Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, e.g. the 2-methoxyethyl, 2-ethoxyethyl, 2-butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
  • Ci-Cio-alkylthio ester is the ethylthio ester.
  • the organic moieties mentioned in the definition of the variables R 1 , R 2 , A, Z, R 3 , R 3A , and R 4 are - like the term halogen - collective terms for individual enumerations of the individual group members.
  • the term halogen denotes in each case F, CI, Br, or I.
  • All hydrocarbon chains, e.g. all alkyl, alkenyl, alkynyl, alkoxy chains can be straight-chain or branched, the prefix C n -C m denoting in each case the possible number of carbon atoms in the group.
  • - CrC 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-C4-alkyl as mentioned above, and also, e.g., n-pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2- dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-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-tri methyl propyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1
  • Ci-C4-haloalkyl Ci-C4-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, pentafluoroeth,
  • Ci-C6- aloalkyl Ci-C4- aloalkyl 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;
  • C3-C6-cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • C3-C6-alkenyl e.g. 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-bu- tenyl, 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,
  • 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, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1 ,1 -dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl- 4-pentynyl, 2-methyl-3-pentynyl, 2-
  • 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, Br and/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-rac_
  • 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-methoxyl butoxy, 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-tri methyl propoxy, 1-ethyl-1-methylpropoxy, and 1 -ethyl-2-
  • Ci-C4-haloalkoxy a Ci-C4-alkoxy group as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., e.g., fluoromethoxy, difluorometh- oxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2-fluoroethoxy, 2-chloro- ethoxy, 2-bromomethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluo- roethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pen- tafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloroprop
  • 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-C6-alkylthio Ci-C4-alkylthio as mentioned above, and also, e.g., pentylthio, 1 -methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hex- ylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1 ,1-dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethyl- butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthi
  • (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-ethyl
  • 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- ⁇ ...
  • 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-methylpent
  • 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- ethylpropylsulf
  • 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-cyclopentadi- enyl, 1 -cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1 ,3-cyclohexadienyl, 1 ,4-cyclohexadienyl, or 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, e.g.
  • 6-membered partial unsaturated heterocycles like 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopy- ran-5-yl, 2H-thiopyran-6-yl, or 5,6-dihydro-4H-1 ,3-oxazin-2-yl.
  • 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.
  • pyrazol-3-yl, pyra- zol-4-yl isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3- yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (e.g. imidazole-2-yl, imidazole-4-yl), oxazolyl (e.g. oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (e.g.
  • 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 sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
  • 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-haloal- kenyloxy C3-C6-alkynyloxy, C4-C6-haloalkynyloxy, Ci-C6-alkylthio, C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
  • R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
  • R 1 is C3-C6-cycloalkyl, wherein the cycloalkyi 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.
  • R 2 is C2-C6-alkenyl, C2-C6-haloalkenyl, CrC 6 -alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkenyl, C3-C6-cycloalkenyl-Ci-C6-alkyl, C3-C6-cycloalkyl-CrC 6 -alkylidenyl, C3-C6- halocycloalkyl-Ci-C6-alkylidenyl, C3-C6-cycloalkenyl-Ci-C6-alkylidenyl, C3-C6-hydroxycycloalkyl- Ci-C6-alkyl, C3-C6-hydroxycycloalkenyl-Ci-C6-alkyl, Ci-C6-hydroxyalkyl, C3-C6-cycloalkyl-C2-C6- hydroxyalkylidenyl,
  • cyclic groups of R 2 are unsubstituted or substituted by R c , and
  • R 2 acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R 2 is C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkenyl, C3-C6-cycloalkyl- Ci-C6-alkylidenyl, C3-C6-halocycloalkyl-Ci-C6-alkylidenyl, C3-C6-hydroxycycloalkyl-Ci-C6-alkyl, C3-C6-hydroxycycloalkyl-Ci-C6-hydroxyalkyl, C2-C6-dihydroxyalkyl, or 5- or 6-membered het- eroaryl;
  • R 2 is C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkenyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, Ci-C6-hydroxyalkyl, Ci-C6-alkoxycarbonyl-CrC 6 -alkyl, C2-C6- dihydroxyalkyl, Ci-C6-dicyanoalkyl, or 5- or 6-membered heteroaryl;
  • cyclic groups of R 2 are unsubstituted or substituted by R c , and
  • R 2 acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R 2 is R 2 is C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, C3-C6-hydroxycycloalkyl-Ci-C6-alkyl, and 5- or 6-membered heteroaryl;
  • R 2 is C2-C6-alkenyl, Ci-C6-hydroxyalkyl, C3-C6-cycloalkyl-Ci-C6-alkyli- denyl, C2-C6-dihydroxyalkyl, Ci-C6-dicyanoalkyl and 5- or 6-membered heteroaryl;
  • R 2 is C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, Ci-C6-hydrox- yalkyl, C2-C6-dihydroxyalkyl, or 5- or 6-membered heteroaryl;
  • cyclic groups of R 2 are unsubstituted or substituted by R c , and _
  • R 2 acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R 2 is C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, or 5- or 6-membered heteroaryl;
  • R 2 is Ci-C6-hydroxyalkyl, C2-C6-dihydroxyalkyl, C3-C6-cycloalkyl-Ci-C6-al- kylidenyl, or 5- or 6-membered heteroaryl;
  • cyclic groups of R 2 are unsubstituted or substituted by R c , and
  • R 2 acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R 2 is C2-C6-alkenyl
  • R 2 is C3-C6-cycloalkyl-Ci-C6-alkylidenyl
  • R 2 is 5- or 6-membered heteroaryl
  • R 2 is 5-membered heteroaryl
  • R 2 is Ci-C6-hydroxyalkyl
  • R 2 is C2-C6-dihydroxyalkyl
  • cyclic groups of R 2 are unsubstituted or substituted by R c , and
  • R 2 acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R 2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, 3-methyl-2-furyl or 4-methyloxazol-5- yl.
  • R 2 is selected from R 2 -1 to R 2 -16 as shown below,
  • # denotes attachment to the pyrimidine ring
  • X and Y denotes R c which independently of each other are identical or different
  • R 2 is R 2 -1 , R 2 -2, R 2 -3, R 2 -4, R 2 -5, R 2 -6, R 2 -7, or R 2 -8;
  • R 2 is R 2 -9, R 2 -10, R 2 -1 1 , R 2 -13, R 2 -14, or R 2 -15;
  • R 2 is R 2 -9, R 2 -10, or R 2 -15;
  • R 2 is R 2 -9;
  • preferred X is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, Ci-C6-haloal- koxy, or Ci-C6-alkylthio;
  • X is H, halogen, CN, Ci-C6-alkyl, OH, Ci-C6-alkoxy, or Ci-C6-alkylthio; also particularrly preferred X is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy;
  • especially preferred X is H, halogen, CN, Ci-C4-alkyl, OH, Ci-C4-alkoxy, or Ci-C4-alkylthio; more preferred X is H, CH3, C2H5, n-propyl, iso-propyl, iso-butyl, n-butyl, OH , OCH3, SCH3, F, CI, Br, or I ;
  • X is H, CH 3 , C 2 H 5 , OH, or OCH 3 ;
  • X is H, CH 3 , C2H5, or SCH 3 ;
  • X is H, CH 3 , C2H5, F, CI, Br, or I .
  • Preferred Y is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, Ci-C 6 -haloal- koxy, or Ci-C6-alkylthio;
  • Y is H, halogen, CN, Ci-C6-alkyl, OH, Ci-C6-alkoxy, or Ci-C6-alkylthio; also particularrly preferred Y is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy;
  • Y is H, halogen, CN, Ci-C4-alkyl, Ci-C2-fluoroalkyl, OH, Ci-C4-alkoxy, or Ci-C 4 -alkylthio;
  • Y is H, CH 3 , C2H5, n- propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, t-butyl, OH, OCH 3 , SCH 3 , F, CI, Br, or I;
  • Y is H, CH 3 , C2H5, n- propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, OH, or OCH 3 ; also most preferred Y is H, CH 3 , C2H5, n-propyl, iso-propyl, OH, OCH 3 , or SCH 3 ;
  • Y is H, CH 3 , C2H5, n-propyl, iso-propyl, F, CI, Br, or I .
  • R 2 is 4-methyl-5-oxazolyl, 4-ethyl-5-oxazolyl, 2,4-dimethyl-5-oxazolyl, 2- ethyl-4-methyl-5-oxazolyl, 2-methyl-4-ethyl-5-oxazolyl, or 2,4-diethyl-5-oxazolyl.
  • R 2 examples of particularly preferred R 2 are provided in Table R 2 -9, Table R 2 -10, and Table R 2 - 15.
  • R 2 -9 examples of particularly preferred R 2 are R 2 -9.1 to R 2 -9.676 wherein R 2 is R 2 -9 and combinitions of variables X and Y are as defined in each row of table R2, numbering of each compound e.g. R 2 -9.1 means R 2 is R 2 -9 wherein X and Y are as defined in row 1 of table R2;
  • R 2 -10 examples of particularly preferred R 2 are R 2 -10.1 to R 2 -10.676 wherein R 2 is R 2 - 10 and combinitions of variables X and Y are as defined in each row of table R2, numbering of each compound e.g. R 2 -10.1 means R 2 is R 2 -10 wherein X and Y are as defined in row 1 of ta- ble R2;
  • Table R 2 -15 examples of particularly preferred R 2 are R 2 -15.1 to R 2 -15.676 wherein R 2 is R 2 - 15 and combinitions of variables X and Y are as defined in each row of table R2, numbering of each compound e.g. R 2 -15.1 means R 2 is R 2 -15 wherein X and Y are as defined in row 1 of table R2.
  • 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.
  • Particularly preferred Z is selected from below groups A to G,
  • R 3 is halogen, CHO, CN, Ci-C 6 -alkyl, d-Ce-haloalkyl, or Ci-C 6 -alkoxy;
  • n 0 or 1 ;
  • R 4 is halogen, CHO, CN, Ci-C 6 -alkyl, C C 6 -haloalkyl, or C C 6 -alkoxy;
  • X is O, S, or NR 3A ;
  • # denotes the point of attachment to the pyridine ring.
  • 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 halogen
  • R 3 is CI, Br, or I ;
  • R 3 is CI or Br.
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -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 CH 3 .
  • 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; especially preferred R 4 is halogen;
  • R 4 is Ci-C6-haloalkyl, or Ci-C6-alkyl
  • R 4 is F, CI, CHF 2 , CF 3 , CH 3 , or C 2 H 5 ;
  • R 4 is F
  • R 4 is CH3
  • R 4 is CI.
  • R 4 is CF3.
  • Preferred m is 0, 1 , or 2;
  • m is 0 or 1 ;
  • R 1 is preferably Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
  • R 1 is C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
  • R 2 is preferably C2-C6-alkenyl, C3-C6-cycloalkylCrC 6 -alkylidenyl, 5- or 6-membered heteroaryl, Ci-C6-hydroxyalkyl, or C2-C6-dihydroxyalkyl;
  • R 2 is C2-C6-alkenyl, 5- or 6-membered heteroaryl, or Ci-C6-hydroxyalkyl; also particularly preferred R 2 is C3-C6-cycloalkylCi-C6-alkylidenyl, 5- or 6-membered het- eroaryl, or C2-C6-dihydroxyalkyl,
  • R 2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, 3-methyl-2-furyl ;
  • A is preferably CR 3 or NR 3A ;
  • particularly preferred A is CR 3 ;
  • A is NR 3A ;
  • Z is preferably pyridine, pyrrole, furan, or thiophene
  • Z is pyridine
  • Z is pyrrole, furan, or thiophene
  • Z is pyridine, furan, or thiophene
  • Z is selected from groups A to G, as defined above;
  • R 3 is preferably halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • R 3 is halogen or CH3
  • R 3 is Br or CI
  • R 3A is preferably H or Ci-C 6 -alkyl
  • R 3A is H or CH3;
  • m is preferably 0 or 1 ;
  • R 4 is preferably halogen or CF 3 .
  • 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 or NR 3A ;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • R 3A is H or Ci-Ce-alkyl
  • Z is pyridine, thiophene, furan, or pyrrol
  • n 0 or 1 ;
  • R 4 is F, CI, CHF 2 , CF 3 , CH 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.2) corresponds to pyridine compounds of formula (I) wh 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 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.3) corresponds to pyridine compounds of formula (I) wh nd 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 ;
  • 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 compounds of formula (I) wherein R 2 is 2-furyl
  • 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 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.5) corresponds to pyridine compounds of formula (I) w their use as herbicide,
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C 3 -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 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.6) corresponds to pyridine compounds of formula (I) wherein R 2 is 3-methyl-2-furyl
  • 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 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.7) corresponds to pyridine compounds of formula (I) wherein R 2 is 2-methyl-3-furyl
  • their use as herbicide,tician .
  • 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 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.8) corresponds to pyridine compounds of formula (I) wh H5), 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 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C2H5.
  • pyridine compounds of formula (1.9) corresponds to pyridine compounds of formula (I) wh uryl
  • 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 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C2H5. Also preferred is the pyridine compounds of formula (1.10) (corresponds to pyridine compounds of formula (I) wherein R 2 is oxazolyl), and their use as herbicide,
  • dotted line ( ) is a single bond or a double bond
  • X and Y independently are selected from H, CH 3 , C2H5, n-propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, t-butyl, OH, OCH 3 , SCH 3 , S(0)CH 3 , S(0) 2 CH 3 , CN, F, CI, Br, I, CH 2 CF 3 , CF 2 CF 3 , CF 2 CH 3 , CF 3 , CF 2 H, OCF 2 H, and OCF 3 ;
  • R 1 is C 3 -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 ;
  • R 4 is F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • Particular preference is given to the pyridine compounds of formula I.A to I.G (corresponds to pyridine compounds of formula (I)), and their use as herbicide, wherein 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 1 is C 2 H 5 , c-C 3 H 5 , C-C4H7, or OCH 3 ;
  • R 3 is CH 3 , OCH 3 , CI, Br, CHF 2 , F, or I;
  • X is O, S, or NR 3A ;
  • n 0 or 1 ;
  • R 4 is F or CF 3 .
  • compounds of the invention are the compounds of the formulae l-A to l-G that are compiled in the Tables 1 to 26.
  • 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,
  • 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, or 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, 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 com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (I.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 (1.3) (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.4) (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 (1.5) (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 for- mula (1.6) (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 (1.7) (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 (1.8) (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 (1.9) (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 (1.10) (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 1.10, 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
  • 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, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- ⁇ ⁇
  • 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-AC- Case herbicides).
  • 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).
  • the herbicidal activity of these compounds is based on the inhibition of acetolac- tate 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 PSIl 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.
  • PSIl inhibitors are preferred.
  • compositions contain at least one inhibitor of pro- toporphyrinogen-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 in- hibition 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 (ble
  • the compositions contain at least one EPSP synthase inhibitor (herbicide b6).
  • the herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid biosynthesis in plants. These inhibitors belong to the group G of the HRAC classification system.
  • the compositions contain at least one glutamine syn- thetase 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 ⁇ _.
  • the compositions contain at least one mitosis inhibitor (herbicide b9).
  • the herbicidal activity of these compounds is based on the disturbance or inhibi- tion 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).
  • VLCFA inhibitor herebicide b10
  • the herbicidal activity of these compounds is based on the inhibition of the syn- thesis 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.
  • 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 herbi- cide (herbicide b13).
  • auxinic herbi- cide 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.
  • These compounds belong to the group P of the HRAC classification system.
  • compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, 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, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, ⁇ ⁇
  • fluazifop-P-butyl haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pi- noxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop- P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,
  • sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, met-
  • imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsu- lam, pyrimisulfan and pyroxsulam,
  • pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)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 420138-40- 5), N-(4-bromophenyl)-2-[(
  • sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
  • compositions compris- ing 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-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl
  • 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, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sul
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21 -3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol
  • 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 ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-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, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, ac- etanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfen- carbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8
  • 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, aminocyclopy- rachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammo- nium, 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
  • auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium;
  • 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, sul- fentrazone, 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-pyr
  • glyphosate glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
  • glufosinate from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P, glufosinate-ammonium;
  • VLCFA inhibitors from the group of the VLCFA inhibitors: acetochlor, alachlor, amidochlor, anilofos, buta- chlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, meta- zachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor 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 as mentioned above;
  • b1 1 from the group of the cellulose biosynthesis inhibitors: 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 aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammoni- um and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlor- prop-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
  • 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-
  • ALS inhibitors from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamu- ron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imaza- pic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodi- um, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsu- lam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon
  • 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 );
  • 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, 11.3 , 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-ben- zyl (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 pre- sent 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 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-(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.
  • 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 (http://www.alan- wood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Com- pany, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998.
  • the assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this substance was only assigned to one mechanism of action.
  • Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agriculturally acceptable derivative in the compositions according to the invention.
  • suitable salts include those, where the counterion is an agriculturally acceptable cation.
  • suitable salts of dicamba are dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba- N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine.
  • 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.
  • 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 dichlor- prop-dimethylammonium.
  • suitable esters of dichlorprop are dichlorprop-butotyl and dichlorprop-isoctyl.
  • Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammo- nium, 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 es- ter 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-diola- mine, 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-dime- thylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
  • Suitable salts of glyphosate are e.g. glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glypho- sate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sul- fosate).
  • 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-dimethylammo- nium, 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-so- dium.
  • 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-dimethylammo- nium, aminocyclopyrachlor-methyl, aminocyclopyrachlor-triisopropanolammonium, aminocyclo- pyrachlor-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-isoprop- ylammonium.
  • 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 .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), (1 .1.1- 46), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), or (1.1.1-67), and as component B at least one, preferably exactly one, herbicide B.
  • component A 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 (1.1), especially preferred the compound (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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), or (1.1.1-67), and at least two, preferably exactly two, herbicides B different from each other.
  • at least two, preferably exactly two, herbicides B different from each other 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 (1.1), especially preferred the compound (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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), or (1.1.1-67), and at least three, preferably exactly three, herbicides B different from each other.
  • at least three, preferably exactly three, herbicides B different from each other 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 (1.1), especially preferred the compound (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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), or (1.1.1-67), and as component C at least one, preferably exactly one, safener C.
  • 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 (1.1), especially preferred the compound (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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), or (1.1.1-67), 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 (1.1), especially preferred the compound (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
  • the composition comprises as component A at least one, preferably exactly pyridine compound of formula (I), preferably of for- mula (1.1), especially preferred the compound (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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), or (1.1.1-67), 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 for- mula (1.1), especially preferred the compound (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
  • 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), (1.1.1-11), (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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), or (1.1.1-67), 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), (1.1.1-11), (1.1.1- 17), (1.1.1-18), (1.1.1-24), (1.1.1-25),
  • 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), (1.2.1-11), (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), (1.2.1-52), (1.2.1-53), (1 .2.1-59), (1.2.1-60), (1 .2.1-66), or (1.2.1-67), and as component B at least one, preferably exactly one, herbicide B.
  • component A 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), (1 .2.1- 46), (1.2.1-52), (1.2.1-53), (1 .2.1-59), (1.2.1-60), (1 .2.1-66), or (1.2.1-67), 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), (1 .2.1- 46), (1.2.1-52), (1.2.1-53), (1 .2.1-59), (1.2.1-60), (1 .2.1-66), or (1.2.1-67), and at least three, prefer- ably 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), (1 .2.1- 46), (1.2.1-52), (1.2.1-53), (1 .2.1-59), (1.2.1-60), (1 .2.1-66), or (1.2.1-67), and as component C at least one, preferably exactly one, safener C.
  • 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), (1 .2.1- 46), (1.2.1-52), (1.2.1-53), (1 .2.1-59), (1.2.1-60), (1 .2.1-66), or (1.2.1-67), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.
  • component B at least one, preferably exactly one, herbicide B
  • 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 (1.2), 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), (1.2.1-46), (1.2.1-52), (1 .2.1-53), (1.2.1-59), (1 .2.1-60), (1.2.1-66), or (1.2.1-67), 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.
  • 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), (1 .2.1- 46), (1.2.1-52), (1.2.1-53), (1 .2.1-59), (1.2.1-60), (1 .2.1-66), or (1.2.1-67), 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-
  • 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), (1 .5.1- 46), (1.5.1-52), (1.5.1-53), (1 .5.1-59), (1.5.1-60), (1 .5.1-66), or (1.5.1-67), and as component B at least one, preferably exactly one, herbicide B.
  • component A 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), (1 .5.1- 46), (1.5.1-52), (1.5.1-53), (1 .5.1-59), (1.5.1-60), (1 .5.1-66), or (1.5.1-67), and at least two, prefera- bly 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), (1 .5.1- 46), (1.5.1-52), (1.5.1-53), (1 .5.1-59), (1.5.1-60), (1 .5.1-66), or (1.5.1-67), 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 .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), (1 .5.1- 46), (1.5.1-52), (1.5.1-53), (1 .5.1-59), (1.5.1-60), (1 .5.1-66), or (1.5.1-67), and as component C at least one, preferably exactly one, safener C.
  • component A 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 .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), (1 .5.1- 46), (1.5.1-52), (1.5.1-53), (1 .5.1-59), (1.5.1-60), (1 .5.1-66), or (1.5.1-67), 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 (1.5), 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), (1.5.1-46), (1.5.1-52), (1 .5.1-53), (1.5.1-59), (1 .5.1-60), (1.5.1-66), or (1.5.1-67), 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 (1.5), 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.
  • 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), (1 .5.1- 46), (1.5.1-52), (1.5.1-53), (1 .5.1-59), (1.5.1-60), (1 .5.1-66), or (1.5.1-67), 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 .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-
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • the composition comprises, in ad- dition 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-4.1-45), (1.2.
  • the composition comprises, in ad- dition 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-6
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • the composition comprises, in ad- dition 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-4.1-45), (1.2.
  • the composition comprises, in ad- dition 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-4.1-45), (1.2.
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-6
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • 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), (1.1.1-52), (1.1.1-53), (1.1.1-59), (1.1.1-60), (1.1.1-66), (1.1.1-67), (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), (1.2.1-52), (1.2.1-53), (1.2.1-59), (1.2.1-60), (1.2.1-66), (1.2.1-45), (1.2.1-4
  • 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: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 prefera- bly 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
  • 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 compound s 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 compound s 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 1.3.1-3 and the substance(s) as defined in the respective row of table T: Table T (compositions 1.1 to 1.3653):

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne des composés de pyridine de la formule (I), ou leurs sels ou dérivés acceptables en agriculture en tant qu'herbicides, où les variables étant définies selon la description, l'utilisation des composés de pyridine de la formule (I) comme herbicides, des compositions les contenant et leur utilisation en tant qu'herbicides, c'est-à-dire pour lutter contre les plantes nocives, et également une méthode de lutte contre une végétation indésirable consistant à laisser agir une quantité efficace d'herbicide d'au moins un composé de pyridine de la formule (I) pour agir sur les plantes, leurs graines et/ou leur habitat.
PCT/EP2017/068599 2016-07-26 2017-07-24 Composés herbicides de pyridine WO2018019755A1 (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
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
US12133529B2 (en) 2017-11-23 2024-11-05 Basf Se Herbicidal phenylethers

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Cited By (6)

* 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
US11419337B2 (en) 2016-07-29 2022-08-23 Basf Se Method for controlling PPO resistant weeds
US11766044B2 (en) 2016-07-29 2023-09-26 Basf Se Method for controlling PPO resistant weeds
US11185075B2 (en) 2016-12-16 2021-11-30 Basf Se Herbicidal phenyltriazolinones
US12133529B2 (en) 2017-11-23 2024-11-05 Basf Se Herbicidal phenylethers
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

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