WO2018019721A1 - Composés herbicides de pyridine - Google Patents

Composés herbicides de pyridine Download PDF

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WO2018019721A1
WO2018019721A1 PCT/EP2017/068491 EP2017068491W WO2018019721A1 WO 2018019721 A1 WO2018019721 A1 WO 2018019721A1 EP 2017068491 W EP2017068491 W EP 2017068491W WO 2018019721 A1 WO2018019721 A1 WO 2018019721A1
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alkyl
haloalkyl
cycloalkyl
formula
alkoxy
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PCT/EP2017/068491
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Florian Vogt
Matthias Witschel
Tobias SEISER
Veronica LOPEZ CARRILLO
Thomas Seitz
Gerd Kraemer
Trevor William Newton
Stefan Tresch
Doreen Schachtschabel
Klaus Kreuz
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Basf Se
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/26—Radicals substituted by halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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

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.
  • R 1 d-Ce-alkyl, d-Ce-haloalkyl, hydroxy-d-Ce-alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C 2 -C 6 - 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-cyclo- alkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, C1-C6- alkylthio,
  • R 2 is Ci-Ce-alkyl, Ci-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-C 2 -C6-haloalkenyl, Ci-C6-haloalkoxy-C 2 -C6-alkenyl, Ci-C6-haloal- koxy-C 2 -C6-haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, CrC 6 -alkoxy-C 2 -C6-alkynyl, Ci- C6-alkoxy-C3-C6-haloalkynyl, Ci-C6-haloalkoxy-C 2 -C6-alkynyl, Ci-C6-haloalk
  • 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, CrC 6 -alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloalkoxycarbonyl-CrC 6 -alkyl, Ci C6-alkoxycarbonyl-CrC 6 -haloalkyl, Ci-C6-haloalkoxycarbonyl-CrC 6 -haloalkyl, Ci-C6-haloalkoxycarbonyl-CrC 6
  • R c is halogen, CN, N0 2 , Ci-Ce-alkyl, CrC 6 -haloalkyl, hydroxy, CrC 6 -alkoxy or CrC 6 - haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, or Ci-C6-alkylsulfonyl;
  • 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, N0 2 , Ci-C 6 -alkyl, CrC 6 -haloalkyl, hydroxy, CrC 6 -alkoxy or CrC 6 - haloalkoxy, Ci-C6-alkylsulfonyl;
  • R 3 halogen, CN, N0 2 , Ci-C 6 -alkyl, d-Ce-haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 - haloalkenyl, C 2 -C6-alkynyl, C 2 -C6-haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6- alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy-
  • R 4 ' R 5 , R 6 and R 7 independently of one another are H, halogen, CN, N0 2 , Ci-C 6 -alkyl, Ci-C 6 - haloalkyl, Ci-C6-alkylcarbonyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, C-C6-alkynyl, C 2 -C6- haloalkynyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3- C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, C1-C6- alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthi
  • R a is halogen, CN, N0 2 , Ci-Ce-alkyl, Ci-Ce-haloalkyl, d-Ce-alkoxy, or d-Ce-haloalkoxy; including agriculturally acceptable salts or derivatives of the pyridine compounds of formula (I) having an acidic functionality.
  • the present invention also provides use of the pyridine compounds of formula (I) as described herein including agriculturally acceptable salts or derivatives of the pyridine compounds of formula (I) having an acidic functionality, as herbicide.
  • 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, 0-, 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 N,N- dimethylacetamide (DMAC), particularly diethyl ether, dioxane and THF.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes
  • aromatic hydrocarbons such as toluene, 0-, m- and
  • 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 (DIPEA) 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
  • DIPEA 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. Syn- let 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 mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, 0-, 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, 0-, 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. 201 1 ):
  • the oxidation of the olefin (IV) to the diol (V) 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.
  • 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.
  • 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,
  • 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 stoichiometric 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 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, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfox- ide, DMF, DMAC, DMI, ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and 1-methyl-2 pyrrolidine (NMP).
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such as sulf
  • 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 NaOCH3, NaOC2H5, 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), organometall
  • 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 pyridine compounds of formula (VII) can be obtained by reacting respective pyridines of formula (I) (prepared analogous to known procedures like e.g. in Angewandte Chemie, International Edition, 49(1 1 ), 2014-2017, S2014/1 -S2014/76; 2010; WO 2014142273; WO
  • the reaction of the pyridine (I) with the electrophile (IX) is usually carried out at temperatures 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.
  • solvents examples include aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, dimethylsulfox- ide, DMF, DMAC, DMI, ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and 1-methyl-2 pyrroli- dinone (NMP). It is also possible to use mixtures of the solvents mentioned.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and T
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal azides, such as lithium hexamethyidisilazide, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, and also alkali metal and alkaline earth metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g.
  • organic bases e.g.
  • tertiary amines such as trimethylamine, triethylamine, diisopro- pylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
  • Particular preference is given to sodium hydride, lithium hexamethyidisilazide and lithium diisopropylamide.
  • 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.
  • 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, dimethylsulfox- ide, DMF, DMAC, DMI, DMPU, DMSO and 1-methyl-2 pyrrolidinone (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, dimethylsulfox- ide
  • suitable metal-containing bases are inorganic compounds including metal-containing bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as U2O , Na20 , K2O, MgO , and CaO, Fe2C>3, Ag2 ⁇ D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC>3, as well as alkali metal hydrogen carbonates (bicarbonates) such as UHCO3, NaHCC>3, KHCO3; alkali metal and alkaline earth metal phosphates such as potassium phosphate (K3PO4), calcium phosphate (Ca3(PC>4)2); alkali metal and alkaline earth metal acetates such as sodium
  • Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide and alkali metal or alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, magnesium carbonate, and calcium carbonate and alkaline earth metal phosphates such as potassium phosphate; ; alkali metal and alkaline earth metal acetates such as sodium acetate.
  • metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide and alkali metal or alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, magnesium carbonate, and calcium carbonate and alkaline earth metal phosphates such as potassium phosphate; ; alkali metal and alkaline earth metal acetates such as
  • Especially preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide and alka- line earth metal phosphates such as potassium phosphate.
  • inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide and alka- line earth metal phosphates such as potassium phosphate.
  • 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 (XIV) 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 DI BALH.
  • 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 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
  • 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 re- acting 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.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as CH 2 CI 2 , CHCI3, CCH2CICH2CI or CCU, ethers such as diethyl ether, diisopropyl ether, tert.-butyl methylether (TBME), dioxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2-imidazolidinone (DMI), DMPU, and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • halogenated hydrocarbons such as CH 2 CI 2 , CHCI3, CCH2CICH2CI or
  • oxidizing agents for the synthesis of pyridines are metal oxides such as ⁇ 2, ⁇ 4, OO3 or PCC, and non-metal oxides such as NaCIO, Nal0 4 or pyridine/SC>3 - complex.
  • metal oxides such as ⁇ 2, ⁇ 4, OO3 or PCC
  • non-metal oxides such as NaCIO, Nal0 4 or pyridine/SC>3 - complex.
  • Swern oxidation or the TEMPO oxidation known to a person skilled in the art can be used to obtain pyridines of formula (XVI).
  • Preferred agents include MnC>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 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, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
  • nitriles such as acetonitrile and propionitrile
  • dipolar aprotic solvents such as
  • 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 azides, such as lithium hex- amethyidisilazide (LHMDS), organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi , and also alkali metal and alkaline earth metal alkoxides, such as
  • organic bases e.g. tertiary amines, such as trimethylamine, triethylamine, diisopro- pylethylamine and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to sodium hydride, lithium hexamethyldisilazide and lithium diisopropylamide.
  • 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 (XVIII).
  • the pyridines of formula (XIX) can be obtained by reacting respective pyridines of formula (XX), obtained e.g. in analogy to Synlett, (5), 808-810, 2002, with boronic acids/esters of formula (X).
  • reaction of pyridines (XX) with boronic acids/esters (XXI) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly prefera- bly 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 reacting the pyridines (XX) with the boronic acids/esters (XXI) in an organic solvent with or without water as co-solvent.
  • Suitable in principle are all solvents which are capable of dissolving the pyridines (XX) and the boronic acids (XXI) 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, 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, 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 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, Ag 2 0; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3,
  • alkali metal hydrogen carbonates such as LiHCC>3, NaHCC>3, KHCO3
  • alkali metal and alkaline earth metal phosphates such as potassium phosphate (K3PO4), calcium phosphate (Ca3(P0 4 )2)
  • alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
  • Preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide and alkali metal or alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, magnesium carbonate, and calcium carbonate and alkaline earth metal phosphates such as potassium phosphate; ; alkali metal and alkaline earth metal acetates such as sodium acetate.
  • metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide and alkali metal or alkaline earth metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, magnesium carbonate, and calcium carbonate and alkaline earth metal phosphates such as potassium phosphate; ; alkali metal and alkaline earth metal acetates such as
  • Especially preferred bases are inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, po- tassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide and alkaline earth metal phosphates such as potassium phosphate.
  • inorganic compounds such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as lithium hydroxide, sodium hydroxide, po- tassium hydroxide, magnesium hydroxide, calcium hydroxide and aluminum hydroxide and alkaline earth metal phosphates such as potassium phosphate.
  • base as used herein also includes mixtures of two or more, preferably two of the above bases. Particular preference is given to the use of one base.
  • the bases are used preferably from 1 to 10 equivalents based on the pyridine (XX), more preferably from 1 .0 to 5.0 equivalents based on the pyridine (XX), most preferably from 1.2 to 2.5 equivalents based on the pyridine (XX).
  • 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 (XX).
  • the end of the reaction can easily be determined by the skilled worker by means of routine methods.
  • reaction mixtures are worked up in a customary manner, e.g. by mixing with water, 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 (XXI) required for the preparation of pyridines of formula (XIX) 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 have ionisable functional groups, preferably an acidic functionality, they can also be employed in the form of their agriculturally acceptable salts. Suitable are, in general, the salts of those cations and the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the activity of the active compounds.
  • Preferred cations are the ions of the alkali metals, preferably of lithium, sodium and potassium, of the alkaline earth metals, preferably of calcium and magnesium, and of the transition metals, preferably of manganese, copper, zinc and iron, further ammonium and substituted ammonium in which one to four 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
  • 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 an acidic functionality can be employed, if applicable, in the form of the acid, in the form of an agriculturally suitable salt, whereby the cations are defined as mentioned above, or else in the form of an agriculturally acceptable derivative, 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 ((tet- rahydrofuran-2-yl)methyl) esters and also as thioesters, 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, alk
  • 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.
  • Preferred alkyl esters are, e.g., the methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, mexyl (1 -methylhexyl), meptyl (1-methylheptyl), heptyl, octyl or isooctyl (2-ethylhexyl) esters.
  • Ci-C4-alkoxy-Ci-C4-alkyl esters are the straight-chain or branched Ci-C4-alkoxy ethyl esters, e.g. the 2-methoxyethyl, 2-ethoxyethyl, 2- butoxyethyl (butotyl), 2-butoxypropyl or 3-butoxypropyl ester.
  • An example of a straight-chain or branched Ci-Cio-alkylthio ester is the ethylthio ester.
  • the organic moieties mentioned in the definition of the variables R 1 , 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.
  • Ci-C 4 -alkyl e.g. CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, CH(CH 3 )-C 2 H 5 , CH 2 -CH(CH 3 ) 2 , and C(CH 3 ) 3 ;
  • Ci-C6-alkyl Ci-C 4 -alkyl as mentioned above, and also, e.g., n-pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -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
  • Ci-C 4 -haloalkyl Ci-C 4 -alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, flu- oromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluo- romethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroeth
  • Ci-C6-haloalkyl Ci-C 4 -haloalkyl as mentioned above, and also, e.g., 5-fluoropentyl, 5- chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl, and dodecafluorohexyl;
  • C 3 -C6-cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • - C 3 -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-
  • C 3 -C6- aloalkenyl a C 3 -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 radical 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- 2-yn-1-yl, 4-iodobut-3-yn-1-yl, 5-fluoropent-3-yn-1 -yl, 5-iodopent-4-yn-1 -yl, 6-fluorohex-4-yn-1 -yl, or 6-iodohex-5-yn-1-yl;
  • Ci-C4-alkoxy e.g. methoxy, ethoxy, propoxy, 1 -methylethoxy butoxy, 1 -methylpropoxy, 2-methylpropoxy, and 1 ,1 -dimethylethoxy;
  • Ci-C6-alkoxy Ci-C4-alkoxy as mentioned above, and also, e.g., pentoxy, 1-methylbut- oxy, 2-methylbutoxy, 3-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-methylprop
  • Ci-C4-haloalkoxy a Ci-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., 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-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., pentyl- amino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2,2-dimethylpropylamino, 1 -ethylpropylamino, hexylamino, 1 ,1-dimethylpropylamino, 1 ,2-dimethylpropylamino, 1-methyl- pentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1 ,1-dimethyl- butylamino, 1 ,2-dimethylbutylamino, 1 ,3-dimethylbutylamino, 2,2-dimethylbutylamino, 2,3-dime- thylbutyl-amino 3,3-dimethylbutylamino, 1 -
  • di(Ci-C4-alkyl)amino e.g. N,N-dimethylamino, ⁇ , ⁇ -diethylamino, N,N-di(1-methyl- ethyl)amino, N,N-dipropylamino, ⁇ , ⁇ -dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-me- thyl-propyl)amino, N,N-di(1 ,1-dimethylethyl)amino, N-ethyl-N-methylamino, N-methyl-N-propyl- amino, N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1 -methylpropylamino, N-methyl-N-(2-methylpropyl)amino, N-(1 ,1-
  • 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- ethylpropylsulfony
  • 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.
  • 3- or 4-membered heterocycles like 2-oxiranyl, 2-aziridinyl, 2-thiiranyl, 2-ox- etanyl, 3-oxetanyl, 2-thietanyl, 3-thietanyl, 1 -azetidinyl, 2-azetidinyl, 1 -azetinyl, or 2-azetinyl; 5- membered saturated heterocycles like2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahy- drothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isox- azolidinyl, 5-isoxazolidinyl, 2-isothiazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl,
  • 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 cycloalkyl substituent is unsubstituted;
  • R 1 is Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
  • R 1 is C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted; also especially preferred R 1 is C2H5, 1-C3H7, 1-C4H9, OCH3, C-C3H5, or C-C4H7;
  • 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-Ci-C6-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 ;
  • 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- CrC 6 -alkylidenyl, C3-C6-halocycloalkyl-CrC 6 -alkylidenyl, C3-C6-hydroxycycloalkyl-CrC 6 -alkyl, C3-C6-hydroxycycloalkyl-CrC 6 -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-Ci-C6-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 ;
  • acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • 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 ;
  • 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 ;
  • 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 Ci-C6-hydroxyalkyl
  • R 2 is C2-C6-dihydroxyalkyl
  • 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 2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, 4-methyl-2-furyl or 4-methyloxazol-5- yi;
  • # 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;
  • 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, CH 3 , C2H5, n-propyl, iso-propyl, iso-butyl, n-butyl, OH, OCH 3 , SCH 3 , F, CI, Br, or I;
  • X is H, CH 3 , C2H5, OH, or OCH 3 ;
  • X is H, CH3, C2H5, or SCH3;
  • X is H, CH3, C2H5, F, CI, Br, or I.
  • Preferred Y is H, halogen, CN, Ci-C 6 -alkyl, Ci-Ce-haloalkyI, OH, Ci-Ce-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, CH3, C2H5, n- propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, t-butyl, OH, OCH3, SCH 3 , F, CI, Br, or I; most preferred 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, CH3, C2H5, n-propyl, iso-propyl, OH, OCH3, or SCH3;
  • Y is H, CH3, 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.
  • 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,
  • halogen particularly preferred halogen, CN , Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen or CH3
  • R 3 is halogen
  • R 3 is CI, Br or I ;
  • R 3 is Br or I .
  • R 3 is Br or CI.
  • R 4 ' R 5 , R 6 and R 7 independently of one another are H, halogen, CN , NO2, Ci-C6-alkyl, C1-C6- haloalkyl, Ci-C6-alkylcarbonyl, C2-C6-alkenyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkoxy-Ci- C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, N H2,
  • R 4 is H, halogen, CN , Ci-Ce-alkyl, d-Ce-haloalkyl or Ci-Ce-alkoxy;
  • R 4 is H, halogen or Ci-C6-alkyl
  • R 4 is H or halogen
  • R 4 is H or F
  • R 4 is H
  • R 4 is F.
  • R 5 is H, halogen, CN , Ci-C 6 -alkyl, Ci-C 6 -haloalkyl or Ci-Ce-alkoxy;
  • R 5 is H, halogen, Ci-C6-alkyl Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, halogen, Ci-C6-alkyl or Ci-C6-haloalkoyl;
  • R 5 is H, F, CI, CH3 or CF3;
  • R 5 is H or halogen
  • R 5 is H or F
  • R 5 is H
  • R 5 is F
  • R 5 is CF3.
  • R 6 is H, halogen, Ci-C6-alkyl or Ci-C6-haloalkyl
  • R 6 is H, halogen or Ci-C6-haloalkyl
  • R 6 is H, halogen or CF3;
  • R 6 is H or halogen
  • R 6 is CF3
  • R 6 is H or F
  • R 6 is H
  • R 6 is F
  • R 6 is CF3.
  • R 7 is H, halogen, CN , Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy; especially preferred R 7 is H, halogen or Ci-C6-haloalkyl;
  • R 7 is H, F, CI or CF3
  • R 7 is H, F or CI
  • R 7 is CF3
  • R 7 is H.
  • R 1 is preferably Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyi substitu- ent is unsubstituted;
  • R 2 is preferably C2-C6-alkenyl, C 3 -C6-cycloalkyl-Ci-C6-alkylidenyl, 5- or 6-membered het- eroaryl, 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 C2-C6-alkenyl, 5- or 6-membered heteroaryl, or Ci-C6-hydroxy- alkyl;
  • R 2 is C3-C6-cycloalkyl-Ci-C6-alkylidenyl, C2-C6-dihydroxyalkyl or 5- or 6-membered heteroaryl;
  • R 2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, or 4-methyl-2-furyl;
  • R 3 is preferably halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 4 is preferably H
  • R 5 is preferably H, Ci-C6-haloalkyl or halogen
  • R 6 is preferably H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl, Ci-C6-alkoxy.
  • R 2 is Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkenyl- Ci-C6-alkyl, Ci-C6-hy- droxyalkyl, C3-C6-hydroxyalkenyl, C3-C6-hydroxycycloalkyl-Ci-C6-alkyl, C3-C6-hydroxycycloal- kenyl-Ci-C6-alkyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
  • 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
  • R c is Ci-Ce-alkyl
  • R d is phenyl, or 5- or 6-membered heteroaryl
  • R d is unsubstituted or substituted by R e ;
  • R 4 is H
  • R 5 is H
  • R 6 is H
  • R 7 is H.
  • pyridine compounds of formula (1.1 ) corresponds to pyridine compounds of formula (I) wherein R 4 is H
  • their use as herbicide
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy.
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, CF3 or halogen
  • R 6 is H, CF3 or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy.
  • pyridine compounds of formula (I.B) corresponds to pyridine compounds of formula (I) wherei R 4 is H
  • their use as herbicide
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy.
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy
  • pyridine compounds of formula (I.D) corresponds to pyridine compounds of formula (I) wherei and their use as herbicide
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy
  • pyridine compounds of formula (I.E) corresponds to pyridine compounds of formula (I) wherei and their use as herbicide
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, d-Ce-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy
  • pyridine compounds of formula (I.F) corresponds to pyridine compounds of formula (I) where is H
  • their use as herbicide
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy
  • pyridine compounds of formula (I.G) corresponds to pyridine compounds of formula (I) wherei is H), and their use as herbicide,
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy
  • pyridine compounds of formula (I.H) corresponds to pyridine compounds of formula (I) where R 4 is H
  • their use as herbicide
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy
  • pyridine compounds of formula (I.I) corresponds to pyridine compounds of formula (I) wherei , R 4 is H), and their use as herbicide,
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy
  • pyridine compounds of formula (I.J) corresponds to pyridine compounds of formula (I) wherein R 2 is 4-methyloxazol-5-yl, R 4 is H), and their use as herbicide,
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl or Ci-C6-alkoxy;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy
  • pyrimidine compounds of formula (I.K) corresponds to pyrimid pounds of formula (I) wherein R 2 is R 2 -9), 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;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl or Ci-C6-alkoxy;
  • R 5 is H, Ci-C6-haloalkyl or halogen
  • R 6 is H, Ci-C6-haloalkyl or halogen
  • R 7 is H, halogen, Ci-C6-alkyl or Ci-C6-alkoxy.
  • pyrimidine compounds of formula (I.K.A) corresponds to pyrimidine compounds of formula (I) wherein R 2 is R 2 -9 and R 4 is H), and their use as herbicide
  • X and Y independently are selected from H, CH 3 , C 2 H5, 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-C 3 H 5 ;
  • R 3 is CI, Br, I, CH 3 , CF 3 , or CF 2 H;
  • R 5 is H or F
  • R 6 is H, F, CF 3 , CI, or Br;
  • R 7 is H or F. Also preferred is the pyridine compounds of formula (1.1 ) (corresponds to pyridine compounds of formula (I) wherein R 4 is H), and their use as herbicide,
  • R 1 is C 2 H 5 , c-C 3 H 5 , c-C 4 H 7 , or OCH 3 ;
  • R 3 is CF 3 , OCH 3 , CH 3 , or halogen
  • R 5 is H or F
  • R 6 is H or F
  • R 7 is H, F, CI, Br, CH 3 or OCH 3 ;
  • compounds of the invention are the compounds of the formulae I that are compiled in the Tables 1 to 9.
  • 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 (I.
  • A) corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.B) (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.C) (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.D) (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.E) (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.F) (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.G) (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.H) (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.I) (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.J) (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.K) (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 I. A to I.K, 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):
  • Mixing partners for the composition can be selected from below herbicides B as defined below: B) herbicides of class b1 ) to b15):
  • ALS inhibitors acetolactate synthase inhibitors
  • PPO inhibitors protoporphyrinogen-IX oxidase inhibitors
  • EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
  • DHP inhibitors 7,8-dihydropteroate synthase inhibitors
  • VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
  • auxin transport inhibitors b14) auxin transport inhibitors; and b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-
  • 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- ACCase 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).
  • ALS inhibitor hereinafter b2
  • the herbicidal activity of these compounds is based on the inhibition of acetolactate synthase and thus on the inhibition of the branched chain amino acid biosynthesis.
  • These inhibitors belong to the group B of the HRAC classification system.
  • the compositions contain at least one inhibitor of photosynthesis (herbicide b3).
  • the herbicidal activity of these compounds is based either on the inhibition of the photosystem II in plants (so-called PSII inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis.
  • PSII inhibitors are preferred.
  • compositions contain at least one inhibitor of protoporphyrinogen-IX-oxidase (herbicide b4).
  • the herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase.
  • These inhibitors belong to the group E of the HRAC classification system.
  • the compositions contain at least one bleacher- herbicide (herbicide b5).
  • the herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis.
  • These include compounds which inhibit carotenoid biosynthesis by inhibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).
  • PDS inhibitors group F1 of HRAC classification
  • HPPD inhibitors 4-hydroxyphenylpyruvate-dioxygenase
  • DOXsynthase group F4 of HRAC class
  • compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown
  • 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 synthetase inhibitor (herbicide b7). The herbicidal activity of these compounds is based on the inhibition of glutamine synthetase, and thus on the inhibition of the aminoacid biosynthesis in plants. These inhibitors belong to the group H of the HRAC classification system.
  • compositions contain at least one DHP synthase inhibitor (herbicide b8).
  • DHP synthase inhibitor herebicide b8
  • the herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase.
  • These inhibitors belong to the group I of the HRAC classification system.
  • the compositions contain at least one mitosis inhibitor (herbicide b9).
  • the herbicidal activity of these compounds is based on the disturbance or inhibition of microtubule formation or organization, and thus on the inhibition of mitosis.
  • These inhibitors belong to the groups K1 and K2 of the HRAC classification system. Among these, compounds of the group K1 , in particular dinitroanilines, are preferred.
  • the compositions contain at least one VLCFA inhibitor (herbicide b10).
  • the herbicidal activity of these compounds is based on the inhibition of the synthesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants.
  • These inhibitors belong to the group K3 of the HRAC classification system.
  • the compositions contain at least one cellulose biosynthesis inhibitor (herbicide b1 1 ).
  • the herbicidal activity of these compounds is based on the inhibition of the biosynthesis of cellulose and thus on the inhibition of the synthesis of cell walls in plants.
  • These inhibitors belong to the group L of the HRAC classification system.
  • the compositions contain at least one decoupler herbicide (herbicide b12).
  • the herbicidal activity of these compounds is based on the disruption of the cell membrane.
  • These inhibitors belong to the group M of the HRAC classification system.
  • the compositions contain at least one auxinic herbicide (herbicide b13). These include compounds that mimic auxins, i.e. plant hormones, and affect the growth of the plants. These compounds belong to the group O of the HRAC classification system.
  • compositions contain at least one auxin transport inhibitor (herbicide b14).
  • auxin transport inhibitor hereinicide b14
  • the herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants.
  • compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b4, b5, b6, b9, b10, b13, and b14.
  • compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, b13, and b14.
  • compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, and b13
  • herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
  • ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethy
  • sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metsulfuron, metsulfuron-methyl, nicos
  • thifensulfuron thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron,
  • imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam,
  • pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-m ethyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2- pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1 -methylethyl ester (CAS 420138-41 -6), 4- [[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01 -8),
  • sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
  • compositions comprising at least one imidazolinone herbicide
  • inhibitors of the photosystem II e.g. 1 -(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1 -(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butyl-1 -methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1 -methyl- pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-methyl-2H-pyr
  • phenmedipham phenmedipham-ethyl
  • nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles such as bromacil, lenacil and terbacil, and bentazon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and inhibitors of the photosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate.
  • a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide;
  • acifluorfen from the group of the protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen,
  • PDS inhibitors beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS NOS NOS NOS NOS NOS NOS
  • HPPD inhibitors benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21 -3), pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1 - methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361 139-71-0), 2-(2,4- dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5- dichlorophenyl)methyl-4,4
  • bilanaphos biases
  • bilanaphos biases
  • bilanaphos- sodium bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium
  • compounds of group K1 dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as amiprophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlorthal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop- isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, compounds of group K1 , in particular dinitroanilines are preferred; b10) from the group of the VLCFA inhibitors:
  • chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethenamid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, acetanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, 11.3 , II.4, II.5, II.6, II.7, II .8 and II.9
  • isoxazoline compounds are known in the art, e.g. from WO 2006/024820, WO
  • chloroacetamides and oxyacetamides preference is given to chloroacetamides and oxyacetamides; b1 1 ) from the group of the cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1 -cyclohexyl-5-pentafluorphenyloxy-1 4 - [1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );
  • 2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters,
  • aminocyclopyrachlor and its salts and esters aminopyralid and its salts such as aminopyralid- dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salt
  • Preferred herbicides B that can be used in combination with the pyrimidine compounds of the formula (I) according to the present invention are:
  • acifluorfen-sodium bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon- ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl- 2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridy
  • glyphosate glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
  • glufosinate glufosinate-P, glufosinate-ammonium
  • 2,4-D and its salts and esters aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammoni- um and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-flu
  • auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
  • b15 from the group of the other herbicides: bromobutide, cinmethylin, cumyluron,
  • herbicides B that can be used in combination with the pyrimidine compounds of the formula (I) according to the present invention are:
  • lipid biosynthesis inhibitors from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyha- lofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro- 4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6- tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2
  • cyclosulfamuron diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron,
  • b3 from the group of the photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn, terbuthylazine, 1 -(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one
  • diflufenican fenquinotrione, flumeturon, flurochloridone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21 -3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate,
  • VLCFA inhibitors from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone; likewise, preference is given to isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
  • auxinic herbicides 2,4-D and its salts and esters such as clacyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluroxypyr- meptyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen- benzyl (CAS 1390661-72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
  • auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
  • herbicides B are the herbicides B as defined above; in particular, the herbicides B.1 - B.202 listed below in table B:
  • compositions according to the present invention comprise at least one pyrimidine compound of formula (I) and at least one safener C.
  • Safeners are chemical compounds which prevent or reduce damage on useful plants without having a major impact on the herbicidal action of the herbicidal active components of the present compositions towards unwanted plants. They can be applied either before sowings (e.g. on seed treatments, shoots or seedlings) or in the pre-emergence application or post- emergence application of the useful plant.
  • the safeners and the pyrimidine compounds of formula (I) and/or the herbicides B can be applied simultaneously or in succession.
  • Suitable safeners are e.g. (quinolin-8-oxy)acetic acids, 1 -phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3- carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1 H-pyrazol-3,5-dicarboxylic acids, 4,5-dihydro- 5,5-diaryl-3-isoxazol carboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenonoximes, 4,6-dihalo-2-phenylpyrimidines, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2- benzoic amides, 1 ,8-naphthalic anhydride, 2-halo-4-(haloalkyl)-5-thiazol carboxylic acids, phosphorthiolates and N-alkyl-O-phenylcarbamates and their
  • Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1 -oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3- oxazolidine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091-06-4).

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 des 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/EP2017/068491 2016-07-26 2017-07-21 Composés herbicides de pyridine WO2018019721A1 (fr)

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CN112979621A (zh) * 2021-03-11 2021-06-18 西华大学 2,3,4,6-四取代吡啶类化合物及其在农药中的用途
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

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