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WO2018019767A1 - Herbicidal pyridine compounds - Google Patents

Herbicidal pyridine compounds Download PDF

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Publication number
WO2018019767A1
WO2018019767A1 PCT/EP2017/068640 EP2017068640W WO2018019767A1 WO 2018019767 A1 WO2018019767 A1 WO 2018019767A1 EP 2017068640 W EP2017068640 W EP 2017068640W WO 2018019767 A1 WO2018019767 A1 WO 2018019767A1
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Prior art keywords
alkyl
haloalkyl
cycloalkyl
alkoxy
methyl
Prior art date
Application number
PCT/EP2017/068640
Other languages
French (fr)
Inventor
Florian Vogt
Matthias Witschel
Tobias SEISER
Veronica LOPEZ CARRILLO
Thomas Seitz
Kraemer GERD
Trevor William Newton
Stefan Tresch
Doreen Schachtschabel
Klaus Kreuz
Original Assignee
Basf Se
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Publication of WO2018019767A1 publication Critical patent/WO2018019767A1/en

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    • 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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • 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
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • C—CHEMISTRY; METALLURGY
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Definitions

  • the present invention relates to pyridine compounds of the general formula (I) defined below and to their use as herbicides. Moreover, the invention relates to compositions for crop protection and to a method for controlling unwanted vegetation.
  • the present invention provides the pyridine compounds of formula (I)
  • the dotted line ( ) is a single bond or a double bond
  • R 1 is Ci-C6-alkyl, Ci-C6-haloalkyl, hydroxy-Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-haloalkoxy, C3-C6- cycloalkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, Ci-C6-alkylthio, Ci-C6-haloalkyl
  • R 2 is d-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-C2-C6-haloalkenyl, Ci-C6-haloalkoxy-C2-C6-alkenyl, Ci-C6-haloal- koxy-C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, CrC 6 -alkoxy-C2-C6-alkynyl, Ci- C6-alkoxy-C3-C6-haloalkynyl, CrC6-haloalkoxy-C2-C6-alkynyl, Ci-C6-haloalkoxy-C3-C6-haloalkyny
  • cyclic groups of R 2 are unsubstituted or substituted by R c ;
  • acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R b is d-Ce-alkyl, Ci-C 6 -haloalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C 3 -C 6 -alkynyl, C 3 -C 6 - haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-halocy- cloalkenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-alkyl, Ci C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-haloalkyl, C1-C6- alkylcarbonyl, Ci-C6-
  • R c is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci-Ce- 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; wherein the substituent R d is unsubstituted or substituted by R e ;
  • R e is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci-Ce- haloalkoxy, Ci-C6-alkylsulfonyl;
  • Z is a 9 or 10 membered bicyclic ring comprising A;
  • A is C * , CR 3 , NR 3A , N, O, or S;
  • C * is a bridge carbon of the bicyclic ring Z
  • R 3 is halogen, CN, CHO, N0 2 , Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 - alkenyl, C 2 -C6-haloalkenyl, C 2 -C6-alkenyl, C 2 -C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloal- koxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, C1-C6- haloalkylthio, NH2, (Ci-C6-alkyl
  • R 3A is H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3- C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-CrC6-alkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH 2 , (Ci-C6-alkyl)amino, di(Ci- C6-alkyl)amino, (Ci
  • R 4 is halogen, CN, CHO, N0 2 , Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C 6 -alkylcarbonyl, C 2 -C 6 - alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloal- koxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, C1-C6- haloalkylthio, NH2, (Ci-C6-alkyl)amino, di
  • R a is halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, d-Ce-alkoxy, or d-Ce-haloalkoxy; m is 0, 1 , 2, or 3;
  • the present invention also provides use of the pyridine compounds of formula (I) as described herein including agriculturally acceptable salts or derivatives of compounds of formula (I) having an acidic functionality, as herbicide.
  • pyridine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, e.g. by the following processes:
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether (TBME), dioxane, anisole and tet- rahydrofuran (THF), and also dimethyl sulfoxide (DMSO), dimethylformamide (DMF) and dime- thylacetamide (DMAC), particularly preferably diethyl ether, dioxane and THF.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mix- tures of Cs-Cs-alkanes
  • aromatic hydrocarbons such as toluene,
  • 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 diisopropylamide (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, based on the pyridine compounds (I).
  • 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, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably toluene and o-xylene.
  • aromatic hydrocarbons such as toluene, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably toluene and o-xylene.
  • Suitable acids are inorganic acids, such as HCI, HBr, sulfuric acid; organic acids p-toluenesul- fonic acid, benzene sulfonic acid, pyridinium p-toluol sulfonic acid, methanesulfonic acid, acetic acid; preferably p-toluenesulfonic acid and HCI.
  • the acids are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the oxidation of the olefin (IV) to the diol (V) is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from 0 °C to 120 °C, particularly preferably from 20 °C to 100 °C, in an inert solvent.
  • the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (IV) with the oxidant in an organic solvent.
  • Suitable in principle are all solvents which are capable of dissolving the pyridines (IV) and the oxidant at least partly and preferably fully under the reaction conditions.
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably TBME, THF It is also possible to use mixtures of the solvents mentioned.
  • Suitable oxidants are e.g. potassium permanganate, potassium perruthenate, osmium tetrox- ide and other osmium salts, like potassium osmate.
  • the oxidant can be used in equimolar amounts or in catalytic amounts together with a reoxidant like N-methylmorpholine-N-oxide or potassium hexacyanoferrate in stochiometric amounts or in excess.
  • the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (VI) with the boronic acid or ester in an organic solvent with or without water as co-solvent. Suitable in principle are all solvents which are capable of dissolving the pyridines (VI) and the boronic acid or ester at least partly and preferably fully under the reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, tert.
  • TBME -butyl methylether
  • anisole and THF nitriles such as acetonitrile and propionitrile
  • dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2-imidaz- olidinone (DMI), ⁇ , ⁇ '-dimethylpropylene urea (DMPU), DMSO and NMP.
  • suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as U2O, Na20, K2O, MgO, and CaO, Fe2C>3, Ag2 ⁇ D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC , as well as alkali metal bicarbonates such as IJHCO3, NaHCC , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
  • base as used herein also includes mixtures of two or more, preferably two of the above 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 (VI), more pref- erably from 1.0 to 5.0 equivalents based on the pyridine (VI), most preferably from 1.2 to 2.5 equivalents based on the pyridine (VI).
  • the reaction of the pyridines (VI) with the phenyl boronic acid or ester is carried out in the presence of a catalyst.
  • suitable catalysts include e.g., palladium based catalysts like, e.g., Palladium(ll)acetate, tetrakis(triphenylphosphine)palladium(0), bis(tri- phenylphosphine)palladium(ll)chloride, or (1 ,1 ,-bis(diphenylphosphino)ferrocene)-dichloropalla- dium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, tri- phenylphosphine, or BINAP (2,2'-Bis(diphenylphospino)-1 ,1 '-binaphthyl).
  • the amount of catalyst is usually 0.01 to 10 mol % (0.0001 to 0.1 equivalents) based on the pyridine (VI).
  • Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Ce-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably diethyl ether, dioxane and THF.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mixtures of Cs-Ce-alkanes
  • aromatic hydrocarbons such as toluene, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF
  • 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 lithium diiso- propylamide, lithium hexamethyidisilazide, lithium 2,2,6,6-tetramethylpiperidide, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi , 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 (TEA), triethylamine (TMA), diiso- propylethylamine (DIPEA) and N-methylpiperidine, pyridine, substituted pyridines, such as col- lidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
  • TEA trimethylamine
  • TMA triethylamine
  • DIPEA diiso- propylethylamine
  • N-methylpiperidine pyridine
  • substituted pyridines such as col- lidine, lutidine and 4-dimethylaminpyridine
  • bicyclic amines Particular preference is given to sodium hydride, lithium 2,2,6,6-tetramethylpiperidide and lithium diisopropylamide (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.
  • Pyridine compounds (VIII), with R equals alkyl, haloalkyl, alkoxy or haloalkoxy, can be ob- tained by reacting respective pyridine compounds of formula (IX) with base and an electrophile (X).
  • Electrophile (X) 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 (IX) with the electrophile is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 80 °C, particularly preferably from -80 °C to 30 °C, in an inert organic solvent in the presence of a base.
  • Suitable in principle are all solvents which are capable of dissolving the pyridine (IX) and the electrophile (X) at least partly and preferably fully under the reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2-imidazolidinone (DMI), ⁇ , ⁇ '- dimethylpropylene urea (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,
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2Hs, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth
  • tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
  • Particular preference is given to NaH, lithium hexamethyldisilazide and LDA.
  • the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile (X), based on the pyridine
  • the reaction of the pyridine (I) with the electrophile (XII) is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 80 °C, par- ticularly 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 (XII) 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, DMSO, DMF, DMAC, DMI, DMPU, DMSO and 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 sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2Hs, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth
  • tertiary amines such as TMA, TEA, DIPEA and N-methylpiperidine
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines.
  • Particular preference is given to NaH, lithium hexamethyldisilazide and LDA.
  • the bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile (XII), based on the pyridine
  • the pyridines of formula (XIV) can be obtained by reacting respective pyridines of formula (XIII) with a reducing agent such as LAH or DIBAIH.
  • the reduction of pyridines (XIII) 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, 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 diethyl ether, dioxane and THF.
  • aliphatic hydrocarbons such as pentane, hexane, cyclohexane and mix- tures 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
  • Examples of reducing agents for pyridines (XIII) include LAH, DIBALH, LiBH 4 or Lithium tri- ethylborohydride.
  • Preferred agents include LAH and DIBALH.
  • the hydride-source is used preferably from 1 to 10 equivalents based on the pyridine (XIII), more preferably from 1.0 to 5.0 equivalents based on the pyridine (XIII), most preferably from 1.2 to 2.5 equivalents based on the pyridine (XIII).
  • 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.
  • the pyridines of formula (XIII) can be obtained by reacting respective pyridines of formula (XV) with boronic acids/esters of formula (XVI):
  • the reaction of pyridines (XV) with boronic acids/esters (XVI) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly preferably from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
  • the reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (XV) with the boronic acids/esters (XVI) in an organic solvent with or without water as co-solvent.
  • Suitable in principle are all solvents which are capable of dissolving the pyridines (XV) and the boronic acids (XVI) at least partly and preferably fully under the reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP
  • suitable metal-containing bases are inorganic compounds including metal-containing bases such as alkali metal and alkaline earth metal hydroxides, and other metal 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, Cs 2 C0 3 , MgC0 3 , and CaC0 3 , as well as alkali metal bicarbonates such as LiHC0 3 , NaHC0 3 , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
  • base as used herein also includes mixtures of two or more, preferably two of the above 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 (XV), more preferably from 1.0 to 5.0 equivalents based on the pyridine (XV), most preferably from 1.2 to 2.5 equivalents based on the pyridine (XV).
  • the reaction of the pyridines (XV) with the boronic acids/esters (XVI) is carried out in the pres- ence 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 (XV).
  • halopyridines XV are known from the literature (e.g. WO 201 1 154327), are commercially available or can be prepared by known procedures.
  • the boronic acids/esters XVI required for the preparation of pyridines of formula (XIII) 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 reaction of pyridines (XIII) 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 (XIII), more preferably from 2.0 to 5.0 equivalents based on the pyridine (XIII), most preferably from 2.0 to 3.0 equivalents based on the pyridine (XIII).
  • the reaction of pyridines (XVIII) 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 (XVIII), more preferably from 2.0 to 5.0 equivalents based on the pyridine (XVIII), most preferably from 2.0 to 3.0 equivalents based on the pyridine (XVIII).
  • the pyridines of formula (XVIII) can be obtained by oxidizing respective pyridines of formula (XI
  • the oxidation of pyridines (XIV) 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 (XIV) in an organic solvent.
  • Suitable in principle are all solvents which are capable of dissolving the pyridines (XIV) 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, CCH 2 CICH 2 CI or CCI 4 , ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and tetrahydrofuran (THF), as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • halogenated hydrocarbons such as CH 2 CI 2 , CHCI3, CCH 2 CICH 2 CI or CCI 4
  • ethers such as diethyl ether
  • oxidizing agents for the synthesis of pyridines are metal oxides such as Mn0 2 , KMn0 4 , CrC or PCC, and non-metal oxides such as NaCIO, Nal0 4 or pyridine/SO-3 - complex.
  • metal oxides such as Mn0 2 , KMn0 4 , CrC or PCC
  • non-metal oxides such as NaCIO, Nal0 4 or pyridine/SO-3 - complex.
  • Swern oxidation or the TEMPO oxidation known to a person skilled in the art can be used to obtain pyridines of formula (XVIII).
  • Preferred agents include Mn0 2 , KMn0 4 and PCC, more preferred Mn0 2 .
  • the oxidizing agent is used preferably from 1 to 50 equivalents based on the pyridine (XIV), more preferably from 1.0 to 20.0 equivalents based on the pyridine (XIV), most preferably from 1.0 to 10.0 equivalents based on the pyridine (XIV).
  • 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 (XX) with the electrophile is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -20 °C to 100 °C, particularly preferably from 0 °C to 30 °C, in an inert organic solvent in the presence of a base.
  • Suitable in principle are all solvents which are capable of dissolving the pyridine (XX) and the electrophile at least partly and preferably fully under the reaction conditions.
  • suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, and NMP.
  • aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene
  • ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF
  • nitriles such as acetonitrile and propionitrile
  • Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LDA, LHMDS, lithium 2,2,6,6-tetramethylpiperidide (LTMP), organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkox- ides, such as NaOCH 3 , NaOC2H 5 , KOC2H5, tBuOK, potassium tert-pentoxide and dimethox- ymagnesium, moreover organic bases, e.g.
  • inorganic compounds such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LDA, LHMDS, lithium 2,2,6,6-tetramethylpiperidide (LTMP
  • tertiary amines such as TMA, TEA, DIPEA and N- methylpiperidine
  • pyridine substituted pyridines, such as collidine, lutidine and 4-dimethyla- minpyridine, and also bicyclic amines.
  • Particular preference is given to NaH, LTMP and LDA.
  • the bases are generally employed in equimolar amounts; however, they can also be em- ployed in catalytic amounts, in excess or, if appropriate, as solvents.
  • the pyridines of formula (I) can also be obtained by reacting respective pyridines of formula (XXII), obtained e.g. in analogy to Synlett, (5), 808-810, 2002, with boronic acids/esters of formula (XXIII):
  • reaction of pyridines (XXII) with boronic acids/esters (XXIII) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly preferably from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
  • reaction may in principle be carried out in substance. However, preference is given to re- acting the pyridines (XXII) with the boronic acids/esters (XXIII) in an organic solvent with or without water as co-solvent.
  • Suitable in principle are all solvents which are capable of dissolving the pyridines (XXII) and the boronic acids (XXIII) 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-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH) 2 , Ca(OH) 2 and AI(OH) 3 ; alkali metal and alkaline earth metal oxide, and other metal oxides, such as Li 2 0, Na20, K 2 0, MgO, and CaO, Fe2C>3, Ag2 ⁇ D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC , as well as alkali metal bicarbonates such as LiHCC>3, NaHCC , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P0 4 )2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
  • base as used herein also includes mixtures of two or more, preferably two of the above compounds. Particular preference is given to the use of one base.
  • the bases are used preferably from 1 to 10 equivalents based on the pyridine (XXII), more preferably from 1 .0 to 5.0 equivalents based on the pyridine (XXII), most preferably from 1 .2 to 2.5 equivalents based on the pyridine (XXII).
  • a catalyst examples include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(tri- phenylphosphine)palladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)- ferrocene)-dichloropalla- dium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, tri- phenylphosphine or BINAP (2,2'-Bis(diphenylphospino)-1 ,1 '-binaphthyl).
  • palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(
  • the amount of catalyst is usually 0.01 to 20 mol % (0.0001 to 0.2 equivalents) based on the pyridine (XXII).
  • 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.
  • the boronic acids/esters (XXIII) required for the preparation of pyridines of formula (I) are commercially available, known from literature or can easily prepared analogously to published procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247).
  • the present invention also provides agrochemical compositions comprising at least one pyridine compounds of formula (I) and auxiliaries customary for formulating crop protection agents.
  • the present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one pyridine compounds of formula (I) is allowed to act on plants, their seeds and/or their habitat.
  • Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
  • pyridine compounds of formula (I) as described herein are capable of forming geomet- rical 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.
  • - CrC 4 -alkyl e.g. CH 3 , C 2 H 5 , n-propyl, CH(CH 3 ) 2 , n-butyl, CH(CH 3 )-C 2 H 5 , CH 2 -CH(CH 3 ) 2 , and C(CH 3 ) 3 ;
  • Ci-C6-alkyl Ci-C4-alkyl as mentioned above, and also, e.g., n-pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2- dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethyl- butyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl- butyl, 1-ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-tri methyl propyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1
  • Ci-C4-haloalkyl Ci-C4-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, flu- oromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluo- romethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl
  • Ci-C6-haloalkyl Ci-C4-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;
  • C3-C6-cycloalkyl monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
  • C3-C6-alkenyl e.g. 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-bu- tenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1- pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-
  • C3-C6-haloalkenyl a C3-C6-alkenyl substituent as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1-yl, 3-chlo- roprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1 -yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2- en-1-yl, 3,3-dibromoprop-2-en-1 -yl, 2,3,3-tribromo-2-en-1-yl, or 2,3-dibromobut-2-en-1 -yl;
  • C3-C6-alkynyl e.g. 1-propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1-methyl-2- propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,
  • C2-C6-alkynyl C3-C6-alkynyl as mentioned above and also ethynyl;
  • C3-C6-haloalkynyl a C3-C6-alkynyl 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-chloropropoxy
  • Ci-C6-haloalkoxy a Ci-C4-haloalkoxy as mentioned above, and also, e.g., 5-fluoro- pentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluoro- hexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
  • Ci-C4-alkylthio e.g. methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1- methylpropylthio, 2-methylpropylthio, and 1 ,1-dimethylethylthio;
  • Ci-C6-alkylthio Ci-C4-alkylthio as mentioned above, and also, e.g., pentylthio, 1 -methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hex- ylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1 ,1-dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethyl- butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthi
  • (Ci-C4-alkyl)amino e.g. methylamino, ethylamino, propylamino, 1 -methylethylamino, bu- tylamino, 1-methylpropylamino, 2-methylpropylamino, or 1 ,1-dimethylethylamino;
  • (Ci-C6-alkyl)amino (Ci-C4-alkylamino) as mentioned above, and also, e.g., 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 -eth
  • 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- ethylpropylsulfon
  • 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;
  • bicyclic ring a 9- to 10-membered bicyclic ring: a partially or fully unsaturated 9- to 10- membered carbocyclic system wherein two partially or fully unsaturated carbocyclic rings are fused with each other through 2 ring members, and which in addition to carbon atoms and independent of their position in the ring can comprise as ring members 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 oxygen atoms and 1 to 2 nitrogen atoms, or 1 or 3 sulfur atoms, or 1 to 4 nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, examples of such bicyclic ring are, 2,3-dihydrobenzothio- phene, benzothiophene, 2,3-dihydrobenzofuran, benzofuran, 1 ,3-benzodioxole, 1 ,3-benzodithi- ole, 1 ,3
  • heterocyclyl a 3- to 6-membered heterocyclyl: a saturated or partial unsaturated cycle having three to six ring members which comprises apart from carbon atoms one to four nitrogen atoms, or one or two oxygen atoms, or one or two sulfur atoms, or one to three nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, e.g.
  • 6-membered partial unsaturated heterocycles like 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 2H-thiopyran-4-yl, 2H-thiopy- ran-5-yl, 2H-thiopyran-6-yl, or 5,6-dihydro-4H-1 ,3-oxazin-2-yl.
  • heteroaryl a 5- or 6-membered heteroaryl: monocyclic aromatic heteroaryl having 5 to 6 ring members which, in addition to carbon atoms and independent of their position in the ring, contains 1 to 4 nitrogen atoms, or 1 to 3 nitrogen atoms and an oxygen or sulfur atom, or an oxygen or a sulfur atom, e.g. 5-membered aromatic rings like furyl (e.g. 2-furyl, 3-furyl), thienyl (e.g. 2-thienyl, 3-thienyl), pyrrolyl (e.g. pyrrol-2-yl, pyrrol-3-yl), pyrazolyl (e.g.
  • pyrazol-3-yl, pyra- zol-4-yl isoxazolyl (e.g. isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl), isothiazolyl (e.g. isothiazol-3- yl, isothiazol-4-yl, isothiazol-5-yl), imidazolyl (e.g. imidazole-2-yl, imidazole-4-yl), oxazolyl (e.g. oxazol-2-yl, oxazol-4-yl, oxazol-5-yl), thiazolyl (e.g.
  • substituted if not specified otherwise refers to substituted by 1 , 2 or maximum pos- sible 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.
  • the substituent R 4 if present, can be present in any ring of "Z".
  • acidic functionality if not specified otherwise refers to a functionality capable of do- nating a hydrogen (proton or hydrogen ion H + ), such as a carboxylic group or a sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
  • 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, OCH 3 , C-C3H5, or C-C4H9;
  • R 1 is C2H5, OCH 3 , or C-C3H5;
  • R 1 is C-C3H5.
  • R 2 is C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-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, hydroxycycloalkenyl-Ci-C6-alkyl, Ci-C6-hydroxyalkyl, C3-C6-cycloalkyl-C2-C6-hydrox- yalkylidenyl, hydroxy
  • cyclic groups of R 2 are unsubstituted or substituted by R c , and
  • R 2 acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R 2 is C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkenyl, C3-C6-cycloalkyl- Ci-C6-alkylidenyl, C3-C6- alocycloalkyl-Ci-C6-alkylidenyl, C3-C6- ydroxycycloalkyl-Ci-C6-alkyl, C3-C6- ydroxycycloalkyl-Ci-C6- ydroxyalkyl, 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 , and
  • 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 , and
  • acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R 2 is C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, or 5- or 6-membered heteroaryl;
  • R 2 is Ci-C6-hydroxyalkyl, C2-C6-dihydroxyalkyl, C3-C6-cycloalkyl-Ci-C6-al- kylidenyl, or 5- or 6-membered heteroaryl;
  • cyclic groups of R 2 are unsubstituted or substituted by R c , and
  • 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 , and
  • acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d .
  • R 2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, 3-methyl-2-furyl, or 4-methyloxazol- 5-yl;
  • R 2 is selected from R 2 -1 to R 2 -16 as shown below,
  • # denotes attachment to the pyridine 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 1 is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, Ci-C6-haloal- koxy, or Ci-C6-alkylthio;
  • X 1 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;
  • X 1 is H, halogen, CN, Ci-C4-alkyl, OH, Ci-C4-alkoxy, or Ci-C4-alkylthio; more preferred X 1 is H, CH3, C2H5, n-propyl, iso-propyl, iso-butyl, n-butyl, OH, OCH3, SCH3, F, CI, Br, or I;
  • X 1 is H, CH 3 , C 2 H 5 , OH, or OCH 3 ;
  • X 1 is H, CH 3 , C 2 H 5 , or SCH 3 ;
  • X 1 is H, CH 3 , C2H5, F, CI, Br, or I.
  • Y 1 is H, halogen, CN, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, Ci-C 6 -haloal- koxy, or Ci-C6-alkylthio;
  • Y 1 is H, halogen, CN, Ci-C6-alkyl, OH, Ci-C6-alkoxy, or Ci-C6-alkylthio; also particularrly preferred Y 1 is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy;
  • Y 1 is H, halogen, CN, Ci-C4-alkyl, Ci-C2-fluoroalkyl, OH, Ci-C4-alkoxy, or CrC 4 -alkylthio;
  • Y 1 is H, CH 3 , C2H5, n- propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, t-butyl, OH, OCH 3 , SCH 3 , F, CI, Br, or I;
  • Y 1 is H, CH 3 , C2H5, n- propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, OH, or OCH 3 ;
  • Y 1 is H, CH 3 , C2H5, n-propyl, iso-propyl, OH, OCH 3 , or SCH 3 ; also most preferred Y 1 is H, CH 3 , C2H5, n-propyl, iso-propyl, F, CI, Br, or I .
  • R 2 is 4-methyl-5-oxazolyl, 4-ethyl-5-oxazolyl, 2,4-dimethyl-5-oxazolyl, 2- ethyl-4-methyl-5-oxazolyl, 2-methyl-4-ethyl-5-oxazolyl, or 2,4-diethyl-5-oxazolyl.
  • R 2 examples of more 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 combinations of variables X 1 and Y 1 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 1 and Y 1 are as defined in row 1 of table R2;
  • Table 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 combinations of variables X 1 and Y 1 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 1 and Y 1 are as defined in row 1 of table 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 combinations of variables X 1 and Y 1 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 1 and Y 1 are as defined in row 1 of table R2.
  • Preferred A is CR 3 , C*.
  • NR 3A N, S or O;
  • A is CR 3 , C*, NR 3A , or N;
  • A is S or O
  • especially preferred A is C*, CR 3 or N;
  • A is CR 3 ;
  • Preferred Z is 9 or l Omembered bicyclic ring
  • particularly preferred Z is 9 membered bicyclic ring; particularly preferred Z is 10 membered bicyclic ring; more preferred Z is selected from below groups A to O,
  • Y is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 heteroatoms selected from O, N, and S;
  • R 3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • n 0, 1 or 2;
  • R 4 is halogen, CN, CrC 6 -alkyl, Ci-C 6 -haloalkyl, or Ci-C 6 -alkoxy;
  • X is O, S, or NR 3A ;
  • R 3A is H, d-Ce-alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
  • # denotes the point of attachment to the pyridine ring.
  • Preferred Y is phenyl
  • Y is 5- or 6-membered partially or fully unsaturated carbocycle comprising 1 , 2, or 3 heteroatoms selected from O, N, and S;
  • Y is phenyl
  • Y is 5-membered partially or fully unsaturated carbocycle comprising 1 , or 2 heteroatoms selected from O, N, and S;
  • Y is 5-membered partially unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms selected from O, N, and S, e.g. 1 ,3-dithiolane, 1 ,3-oxathiolane, 1 ,3-dioxolane, 2,3- dihydrofuran, 2,3-dihydrothiophene, or 2,3-dihydro-1 H-pyrrole; more preferably heteroatoms are selected from O and S, e.g.
  • heteroatom in Y is O, e.g. 1 ,3-dioxolane, or 2,3-dihydrofuran; also most preferred heteroatom in Y is S, e.g.
  • Y is 5-membered fully unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms selected from O, N, and S (furan, thiophene, 1 H-pyrrole, 1 ,2-oxazole, 1 ,3-oxazole, 1 ,2-thiazole, 1 ,3-thiazole, imidazole, 1 H-pyrazole); more preferably heteroatoms are selected from O and S; most preferred heteroatom is O; also most preferred heteroatom is S;
  • Y is 5-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms
  • Y is 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms selected from O, N, and S;
  • more preferred Y is 6-membered partially unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S; more preferably heteroatoms are selected from O and S; also more preferably heteroatoms are selected from O and N; most preferred heteroatom is O; also more preferred Y is 6-membered fully unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms N;
  • R 3 is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or C3-C6-cycloal- kyl;
  • R 3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy,
  • R 3 is halogen, CN, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • R 3 is halogen
  • R 3 is CI, Br, or I
  • R 3 is CI or Br.
  • R 3A is H, Ci-C 6 -alkyl, Ci-C 6 -haloalkyl, Ci-C 6 -alkylcarbonyl, C 3 -C 6 -alkenyl, C 3 -C 6 - haloalkenyl, C3-C6-alkenyl, C 3 -C6-haloalkenyl, or C 3 -C6-cycloalkyl;
  • R 3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkylcarbonyl;
  • R 3A is H, Ci-C6-alkyl, or Ci-C6-alkylcarbonyl
  • R 3A is H, or Ci-C6-alkyl
  • R 3A is H, or CH3.
  • R 4 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • R 4 is halogen, Ci-C6-haloalkyl, or Ci-C6-alkyl;
  • R 4 is halogen
  • R 4 is Ci-C6-haloalkyl, or Ci-C6-alkyl
  • R 4 is F, CI, CHF 2 , CF3, CH 3 , or C 2 H 5 ;
  • R 4 is F
  • R 4 is CH3
  • R 4 is CI.
  • R 4 is CF3.
  • Preferred m is 0, 1 , or 2;
  • m is 0 or 1 ;
  • Preferred Z is A, B, C, D, E, F, G, H, I, J, or K;
  • Z is A, E, or F
  • Z is L, M, N, or O
  • R 1 is preferably Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
  • R 1 is C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
  • R 2 is preferably C2-C6-alkenyl, C3-C6-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 C3-C6-cycloalkyl-CrC 6 -alkylidenyl, C2-C6-dihydroxyalkyl or 5- or 6-membered heteroaryl;
  • R 2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, 3-methyl-2-furyl, 4-methyloxazol-5- yl, CHOH-CHOH-C 6 H 5 , or CHOH-CHOH-2-furyl;
  • A is preferably CR 3 , C * , N, O, S or NR 3A ;
  • A is CR 3 , C * , or N;
  • A is CR 3 , C * , O or S;
  • Preferred Z is 9 or 10 membered bicyclic ring
  • Z is 9 membered bicyclic ring
  • Z is 10 membered bicyclic ring
  • Z is selected from group A to O, as defined herein;
  • R 3 is preferably halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • R 3 is halogen or CH 3 ;
  • R 3A is preferably H or Ci-C 6 -alkyl
  • R 3A is H or CH3;
  • m is preferably 0 or 1 ;
  • R 4 is preferably halogen.
  • R 2 is Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C 3 -C6-cycloalkyl-Ci-C6-alkyl, C 3 -C6-cycloal- kenyl-Ci-C6-alkyl, C 3 -C6-cycloalkyl-CrC 6 -alkylidenyl, Ci-C6-hydroxyalkyl, hydroxycarbonyl-Cr C6-alkyl, hydroxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkoxycar- bonyl-Ci-C6-haloalkyl, or 5- membered heteroaryl;
  • cyclic groups of R 2 are unsubstituted or substituted by R c , and
  • acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d ;
  • R b is d-Ce-alkyl
  • R c is d-Ce-alkyl or OH
  • R d is phenyl or 5- or 6- membered heteroaryl
  • R d is unsubstituted or substituted by R e ;
  • R e is halogen, CN, N0 2 , Ci-Ce-alkyl, Ci-C 6 -haloalkyl, OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, Ci-C6-alkylsulfonyl;
  • Z is A, E or F; Y is 5- or 6-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms; R 3 is R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy; prefer- rably Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-haloalkoxy; more preferrably CI, Br, F, I, CH3, or OCF3; most preferably CI;
  • n 0 or 1 ;
  • R 4 is halogen, preferably Br.
  • R 1 is c-C 3 H 5 ;
  • R 2 is Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkyl, d-Ce-cycloal- kenyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, Ci-C6-hydroxyalkyl, Ci-d-alkoxycarbonyl- Ci-C6-alkyl, or 5- membered heteroaryl;
  • cyclic groups of R 2 are unsubstituted or substituted by R c , and
  • acyclic aliphatic groups of R 2 are unsubstituted or substituted by R d ;
  • R b is Ci-Ce-alkyl
  • R c is Ci-Ce-alkyl or OH
  • R d is 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-Ce-alkyl, Ci-Ce-haloalkyl, OH, Ci-C 6 -alkoxy, Ci-C 6 -haloalkoxy, d-Ce-alkylsulfonyl;
  • Y is 5- or 6-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms;
  • R 3 is R 3 is halogen, Ci-d-alkyl, Ci-d-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy; preferably Ci-d-alkyl, Ci-C6-haloalkyl, or d-d-haloalkoxy; more preferably CI, Br, F, I, CH 3 , or OCF 3 ; most preferably CI;
  • n is 0 or 1 ; preferably 0;
  • R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C2H5.
  • R 2 is R 2 -9, R 2 -10 or R 2 -15, preferably R 2 -9;
  • Y is 5- or 6-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms;
  • R 3 is R 3 is halogen, Ci-d-alkyl, Ci-d-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy; preferably Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-d-haloalkoxy; more preferably CI, Br, F, I, CH3, or OCF3; most preferably CI;
  • n is 0 or 1 ; preferably 0;
  • R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C2H5.
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 , C * , NR 3A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • R 3A is H or Ci-Ce-alkyl
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF2, CF 3 , CH 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.2) corresponds to pyridine compounds of form and their use as herbicide
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 , C * , NR 3A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF 2 , CH3, CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.3) corresponds to pyridine compounds of form H2)4, and their use as herbicide,
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 , C * , NR 3A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF 2 , CH 3 , CF 3 , or C2H5.
  • pyridine compounds of formula (1.4) corresponds to pyridine compounds of formula (I) wherein R 2 is 2-furyl
  • their use as herbicide
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 , C * , NR 3A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.5) corresponds to pyridine com- pounds of formula (I) wherein R 2 is 3-furyl
  • their use as herbicide
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 , C * , NR 3A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.6) corresponds to pyridine com- pounds of formula (I) wherein R 2 is 3-methyl-2-furyl
  • their use as herbicide
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 , C * , NR 3A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.7) corresponds to pyridine com- pounds of formula (I) wherein R 2 is 2-methyl-3-furyl
  • their use as herbicide
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 , C * , NR 3A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.8) corresponds to pyridine com- pounds of formul HOH-C6H5
  • their use as herbicide are also preferred.
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 , C * , NR A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF 2 , CH 3 , CF 3 , or C2H5.
  • pyridine compounds of formula (1.9) corresponds to pyridine pounds of formul HOH-2-furyl), and their use as herbicide,
  • dotted line ( ) is a single bond or a double bond
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
  • A is CR 3 , C * , NR A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF 2 , CH 3 , CF 3 , or C2H5. Also preferred are the pyridine compounds of formula (1.10) (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;
  • A is CR 3 , C * , NR 3A , N, O or S;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, CHF 2 , CH 3 , CF 3 , or C 2 H 5 .
  • pyridine compounds of formula (1.1 1 ) corresponds to pyridin
  • dotted line ( ) is a single bond or a double bond
  • X 1 and Y 1 independently are selected from H, CH3, C2H5, n-propyl, iso-propyl, iso-butyl, n-bu- tyl, 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; preferably c-C 3 H5;
  • A is CR 3 ;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • Z is radical selected from A to O
  • n 0 or 1 ;
  • R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 ; preferably F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 ; more preferably CI.
  • pyridine compounds of formula (1.1 1) corresponds to pyridine compounds of formula (I), wherein R 2 is R 2 -9) and their use as herbicide,
  • X 1 and Y 1 independently are selected from H, CH 3 , C2H5, n-propyl, iso-propyl, iso-butyl, n-bu- tyl, 2-butyl, t-butyl, OH, OCH 3 , SCH 3 , S(0)CH 3 , S(0) 2 CH 3 , CN, F, CI, Br, I, CH2CF3, CF2CF3, CF2CH3, CF 3 , CF2H, OCF2H, and OCF 3 ;
  • X, V and W independently are CH 2 , CF 2 , O, NR 3A , N or S; wherein R 3A is H or CH 3 ;
  • R 1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy; preferably C-C3H5;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • n 0 or 1 ;
  • R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5; preferably F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 ; more preferably CI.
  • pyridine compounds of formula (1.1 1.C) corresponds to pyridine compounds of formula (I), wherein wherein R 2 is R 2 -9) and their use as herbicide,
  • X 1 and Y 1 independently are selected from H, CH 3 , C2H5, n-propyl, iso-propyl, iso-butyl, n-bu- tyl, 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 ;
  • X, V and W independently are CH 2 , CF 2 , O, NR 3A , N or S; wherein R 3A is H or CH 3 ;
  • R 1 is C 3 -C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy; preferably c-C 3 Hs;
  • R 3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
  • n 0 or 1 ;
  • R 4 is F, Br, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5; preferably F, CI, CHF 2 , CH 3 , CF 3 , or C 2 H 5 ; more preferably CI.
  • pyridine compounds of formula I which corresponds to compounds of formulae I. a to I.I, and their use as herbicide, wherein X, V and W independently are CH 2 , CF 2 , O, NR A , N or S.
  • pyridine compounds of formula I which corresponds to compounds of formulae l.m and l.n, and their use as herbicide, wherein X, and V independently are CH 2 , CF 2 , O, NR 3A , N or S, W independently is CH or N.
  • R 1 is C2H5, C-C3H5, C-C4H7, or OCH3;
  • R 3 is CH 3 , OCH3, CI, Br, CHF 2 , CF 3 , F, or I;
  • V is CH 2 or CF 2 ;
  • W is CH 2 , O, N, or S
  • n 0 or 1 ;
  • R 4 is F, CI or CF 3 .
  • R 1 is C2H5, C-C3H5, C-C4H7, or OCH3;
  • V is CH 2 or CF 2 ;
  • W is CH or N
  • n 0 or 1 ;
  • R 4 is F, CI or CF 3 .
  • Particularly preferred compounds of formula I, and their use as herbicide, compounds of the invention are the compounds of the formulae that are compiled in the following Tables 1 to 52.
  • Compound 1.1 .1-3 e.g. comprises the compound of formula 1.1 from Table 1 and line I-3 from Table A;
  • the pyridine compounds of formula (I) may be mixed with a large number of representatives of other herbicidal or growth- regulating active ingredient groups and then applied concomitantly.
  • Suitable components for mixtures are, e.g., herbicides from the classes of the acetamides, amides,
  • aryloxyphenoxypropionat.es benzamides, benzofuran, benzoic acids, benzothiadiazinones, bipyridylium, carbamates, chloroacetamides, chlorocarboxylic acids, cyclohexanediones, dinitroanilines, dinitrophenol, diphenyl ether, glycines, imidazolinones, isoxazoles,
  • phenylpyrazolines phenylpyridazines, phosphinic acids, phosphoroamidates,
  • phosphorodithioates phthalamates, pyrazoles, pyridazinones, pyridines, pyridinecarboxylic acids, pyridinecarboxamides, pyrimidinediones, pyrimidinyl(thio)benzoates, quinolinecarboxylic acids, semicarbazones, sulfonylaminocarbonyltriazolinones, sulfonylureas, tetrazolinones, thiadiazoles, thiocarbamates, triazines, triazinones, triazoles, triazolinones,
  • triazolocarboxamides triazolopyrimidines, triketones, uracils, or ureas.
  • pyridine compounds of formula (I) alone or in combination with other herbicides, or else in the form of a mixture with other crop protection agents, e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria.
  • other crop protection agents e.g. together with agents for controlling pests or phytopathogenic fungi or bacteria.
  • miscibility with mineral salt solutions which are employed for treating nutritional and trace element deficiencies.
  • Other additives such as non-phytotoxic oils and oil concentrates may also be added.
  • compositions according to the present invention comprise at least one pyridine compound of formula (I) (compound A) and at least one further active compound selected from herbicides B, preferably herbicides B of class b1 ) to b15), and safeners C (compound C).
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.1 ) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (I.2) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.3) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.4) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (1.5) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of for- mula (1.6) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.7) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (1.8) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.9) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.10) (corresponds to pyridine compound of formula (I)), as defined herein;
  • Preferred compounds of the formula (I) which, as component A, are constituent of the composition according to the invention are the compounds 1.1 to 1.10, as defined above;
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.1 1 ) (corresponds to pyridine compound of formula (I)), as defined herein;
  • the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of for- mula (1.1 1.
  • 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 (1.1 1.C) (corresponds to pyridine compound of formula (I)), as defined herein;
  • compositions according to the present invention comprise at least one pyridine compound of formula (I) and at least one further active compound B (herbicide B).
  • the further herbicidal compound B (component B) is preferably selected from the herbicides of class b1 ) to b15):
  • compositions can be selected from below herbicides B as defined below:
  • ALS inhibitors acetolactate synthase inhibitors
  • PPO inhibitors protoporphyrinogen-IX oxidase inhibitors
  • EBP inhibitors enolpyruvyl shikimate 3-phosphate synthase inhibitors
  • DHP inhibitors 7,8-dihydropteroate synthase inhibitors
  • VLCFA inhibitors inhibitors of the synthesis of very long chain fatty acids
  • herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indaziflam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dym- ron, methyl iodide,
  • the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1 ). These compounds inhibit lipid biosynthesis. Inhibition of the lipid bi- osynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter- termed ACCase herbicides) or through a different mode of action (hereinafter termed non-AC- Case herbicides).
  • ACCase herbicides belong to the group A of the HRAC classification system whereas the non-ACCase herbicides belong to the group N of the HRAC classification.
  • the compositions contain at least one ALS inhibitor (herbicide b2). The herbicidal activity of these compounds is based on the inhibition of acetolac- tate synthase and thus on the inhibition of the branched chain amino acid biosynthesis. These inhibitors belong to the group B of the HRAC classification system.
  • the compositions contain at least one inhibitor of photosynthesis (herbicide b3).
  • the herbicidal activity of these compounds is based either on the in- hibition of the photosystem II in plants (so-called PSIl inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis.
  • PSIl inhibitors are preferred.
  • compositions contain at least one inhibitor of pro- toporphyrinogen-IX-oxidase (herbicide b4).
  • the herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase.
  • These inhibitors belong to the group E of the HRAC classification system.
  • the compositions contain at least one bleacher-herbicide (herbicide b5).
  • the herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis.
  • These include compounds which inhibit carotenoid biosynthesis by inhibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).
  • PDS inhibitors group F1 of HRAC classification
  • HPPD inhibitors 4-hydroxyphenylpyruvate-dioxygenase
  • DOXsynthase group F4 of HRAC class
  • compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher -
  • compositions contain at least one EPSP synthase inhibitor (herbicide b6).
  • EPSP synthase inhibitor herebicide b6
  • the herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid biosynthesis in plants.
  • These inhibitors belong to the group G of the HRAC classification system.
  • compositions contain at least one glutamine synthetase inhibitor (herbicide b7).
  • the herbicidal activity of these compounds is based on the inhi- bition 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, com- pounds 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.
  • compositions contain at least one decoupler herbi- cide (herbicide b12).
  • the herbicidal activity of these compounds is based on the disruption of the cell membrane.
  • These inhibitors belong to the group M of the HRAC classification system.
  • the compositions contain at least one auxinic herbicide (herbicide b13).
  • auxinic herbicide include compounds that mimic auxins, i.e. plant hormones, and affect the growth of the plants. These compounds belong to the group O of the HRAC classifica- tion system.
  • compositions contain at least one auxin transport inhibitor (herbicide b14).
  • auxin transport inhibitor hereinicide b14
  • the herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants.
  • These compounds belong to the group P of the HRAC classification system.
  • compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b4, b5, b6, b9, b10, b13, and b14.
  • compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, b13, and b14.
  • compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, and b13
  • herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
  • ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pi- noxaden, profoxydim, propaquizafop, quizalofop, quizalofop-
  • sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, met-
  • imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsu- lam, pyrimisulfan and pyroxsulam,
  • pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methylethyl ester (CAS 420138-41 -6), 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,
  • 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-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl
  • a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide;
  • acifluorfen acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyradonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulf
  • 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, pyrazol- ynate, 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-dime- thyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-d
  • bilanaphos biases
  • bilanaphos biases
  • bilanaphos- sodium bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium
  • compounds of group K1 dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, compounds of group K1 , in particular dinitroanilines are preferred;
  • chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, ac- etanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfen- carbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8
  • 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, aminocyclopy- rachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammo- nium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl
  • auxin transport inhibitors diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium;
  • Preferred herbicides B that can be used in combination with the pyridine compounds of the formula (I) according to the present invention are:
  • ALS inhibitors amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlor- sulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysul- furon, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfu- ron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl- sodium, iofensulfuron, iofens
  • acifluorfen-sodium bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon- ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen-ethyl, saflufenacil, sul- fentrazone, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl- 2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyr
  • glyphosate glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
  • glufosinate glufosinate-P, glufosinate-ammonium
  • VLCFA inhibitors from the group of the VLCFA inhibitors: acetochlor, alachlor, amidochlor, anilofos, buta- chlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, meta- zachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor and isoxazoline-compounds of the formulae 11.1 , II.2, 11.3 , II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
  • b1 1 from the group of the cellulose biosynthesis inhibitors: dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorphenyloxy-1 4 -[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );
  • 2,4-D and its salts and esters aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammoni- um and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlor- prop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-
  • auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
  • herbicides B that can be used in combination with the pyridine compounds of the formula (I) according to the present invention are: b1 ) from the group of the lipid biosynthesis inhibitors: clodinafop-propargyl, cycloxydim, cyha- lofop-butyl, fenoxaprop-P-ethyl, pinoxaden, profoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-
  • ALS inhibitors from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamu- ron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imaza- pic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodi- um, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsu- lam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon
  • b3 from the group of the photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn, terbuthylazine, 1 -(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2- one (CAS 1844836-64-1 );
  • glufosinate from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;
  • VLCFA inhibitors from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentra- zamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfen- carbazone and pyroxasulfone; likewise, preference is given to isoxazoline compounds of the formulae 11.1 , II.2, 11.3 , II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
  • auxinic herbicides 2,4-D and its salts and esters such as clacyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluroxypyr- meptyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-ben- zyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
  • auxin transport inhibitors diflufenzopyr and diflufenzopyr-sodium
  • herbicides B are the herbicides B as defined above; in particular, the herbicides B.1 - B.202 listed below in table B:

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Abstract

The present invention relates to the pyridine compounds of formula (I), or their agriculturally acceptable salts or derivatives as herbicides, wherein the variables are defined according to the description, use of the pyridine compounds of formula (I) as herbicide, compositions comprising them and their use as herbicides, i.e. for controlling harmful plants, and also a method for controlling unwanted vegetation which comprises allowing a herbicidal effective amount of at least one pyridine compounds of the formula (I) to act on plants, their seed and/or their habitat.

Description

Herbicidal pyridine compounds
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.
In agriculture, there is a constant demand to develop novel active ingredients, which complement or outperform present methods of treatment regarding activity, selectivity and environmental safety.
These and further objects are achieved by pyridine compounds of formula (I), defined below, and by their agriculturally suitable salts.
Accordingly, the present invention provides the pyridine compounds of formula (I)
Figure imgf000002_0001
wherein
the dotted line ( ) is a single bond or a double bond;
R1 is Ci-C6-alkyl, Ci-C6-haloalkyl, hydroxy-Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2- C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, Ci-C6-haloalkoxy, C3-C6- cycloalkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6-halocycloalkenyloxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, Ci-C6-alkyl- sulfinyl, Ci-C6-alkylsulfonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloalkyl, C3- Ce-halocycloalkenyl, [1-(Ci-C6-alkyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkenyl)]-C3-C6-cycloalkyl, [1-(C2-C6-alkynyl)]-C3-C6-cycloalkyl, [1-(Ci-C6-haloalkyl)]-C3-C6-cycloalkyl, [1-(C2-C6- haloalkenyl)]-C3-C6-cycloalkyl, [1 -(C3-C6-haloalkynyl)]-C3-C6-cycloalkyl, C3-C6-cycloalkyl- Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy, C3-C6-cycloal- kyl-Ci-C6-haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered hetero- cyclyl;
wherein the cyclic groups of R1 are unsubstituted or substituted by Ra;
R2 is d-Ce-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy-C2-C6- alkenyl, Ci-C6-alkoxy-C2-C6-haloalkenyl, Ci-C6-haloalkoxy-C2-C6-alkenyl, Ci-C6-haloal- koxy-C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, CrC6-alkoxy-C2-C6-alkynyl, Ci- C6-alkoxy-C3-C6-haloalkynyl, CrC6-haloalkoxy-C2-C6-alkynyl, Ci-C6-haloalkoxy-C3-C6- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkenyl, C3-C6-halocycloal- kenyl, C3-C6-cycloalkyl- Ci-C6-alkyl, C3-C6-cycloalkyl- Ci-C6-haloalkyl, C3-C6-halocycloal- kyl- Ci-C6-alkyl, C3-C6-halocycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkenyl- Ci-C6-alkyl, C3- C6-cycloalkenyl-Ci-C6-haloalkyl, C3-C6-halocycloalkenyl- Ci-C6-alkyl, C3-C6-halocycloal- kenyl- Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2-C6-alkenyl, C3-C6-cycloalkyl- C2-C6-haloal- kenyl, C3-C6-halocycloalkyl- C2-C6-alkenyl, C3-C6-halocycloalkyl- C2-C6-haloalkenyl, C3-C6- cycloalkenyl- C2-C6-alkenyl, C3-C6-cycloalkenyl- C2-C6-haloalkenyl, C3-C6-halocycloal- kenyl- C2-C6-alkenyl, C3-C6-halocycloalkenyl- C2-C6-haloalkenyl, C3-C6-cycloalkyl- C2-C6- alkynyl, C3-C6-cycloalkyl-C3-C6-haloalkynyl, C3-C6- alocycloalkyl-C2-C6-alkynyl, C3-C6- al- ocycloalkyl-C3-C6- aloalkynyl, C3-C6-cycloalkenyl-C2-C6-alkynyl, C3-C6-cycloalkenyl-C3-C6 haloalkynyl, C3-C6-halocycloalkenyl-C2-C6-alkynyl, C3-C6- alocycloalkenyl-C3-C6- aloal- kynyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, C3-C6-cycloalkyl-C2-C6-haloalkylidenyl, C3-C6- halocycloalkyl-Ci-C6-alkylidenyl, C3-C6-halocycloalkyl-C2-C6- aloalkylidenyl, C3-C6-cycloal kenyl-Ci-C6-alkylidenyl, C3-C6-cycloalkenyl-C2-C6- aloalkylidenyl, C3-C6- alocycloalkenyl- Ci-C6-alkylidenyl, C3-C6-halocycloalkenyl-C2-C6- aloalkylidenyl, heterocyclyl-Ci-C6-alkyli- denyl, heterocyclyl-C2-C6- aloalkylidenyl, C3-C6-hydroxycycloalkyl-Ci-C6-alkyl, C3-C6- y- droxycycloalkyl-CrC6- aloalkyl, C3-C6- ydroxycycloalkenyl-Ci-C6-alkyl, C3-C6-hydroxycy- cloalkenyl-Ci-C6- aloalkyl, Ci-C6- ydroxyalkyl, C2-C6-hydroxyhaloalkyl, C3-C6-hydroxy- alkenyl, C3-C6- ydroxyhaloalkenyl, C3-C6- ydroxyalkynyl, C4-C6- ydroxyhaloalkynyl, C3- C6- ydroxycycloalkyl, C3-C6- ydroxyhalocycloalkyl, C3-C6- ydroxycycloalkenyl, C3-C6-hy- droxyhalocycloalkenyl, C3-C6-cycloalkyl-Ci-C6- ydroxyalkyl, C3-C6-cycloalkyl-C2-C6-hy- droxyhaloalkyl, C3-C6-halocycloalkyl-Ci-C6-hydroxyalkyl, C3-C6- alocycloalkyl-C2-C6- y- droxyhaloalkyl, C3-C6-cycloalkenyl-Ci-C6- ydroxyalkyl, C3-C6-cycloalkenyl-C2-C6-hydroxy- haloalkyl, C3-C6- alocycloalkenyl-Ci-C6- ydroxyalkylC3-C6- alocycloalkenyl-C2-C6- ydrox yhaloalkyl, C3-C6-cycloalkyl-C3-C6- ydroxyalkenyl, C3-C6-cycloalkyl-C3-C6-hydroxyhaloal- kenyl, C3-C6- alocycloalkyl-C3-C6- ydroxyalkenyl, C3-C6-halocycloalkyl-C3-C6-hydroxy- haloalkenyl, C3-C6-cycloalkenyl-C3-C6- ydroxyalkenyl, C3-C6-cycloalkenyl-C3-C6-hydroxy- haloalkenyl, C3-C6- alocycloalkenyl-C3-C6- ydroxyalkenyl, C3-C6- alocycloalkenyl-C3-C6- hydroxyhaloalkenyl, C3-C6-cycloalkyl-C3-C6- ydroxyalkynyl, C3-C6-halocycloalkyl-C3-C6- hydroxyalkynyl, C3-C6-cycloalkenyl-C3-C6- ydroxyalkynyl, C3-C6- alocycloalkenyl-C3-C6- hydroxyalkynyl, C3-C6-cycloalkyl-C2-C6- ydroxyalkylidenyl, C3-C6-halocycloalkyl-C2-C6- y- droxyalkylidenyl, C3-C6-cycloalkenyl-C2-C6- ydroxyalkylidenyl, C3-C6-halocycloalkyl-C2-C6 hydroxyalkylidenyl, heterocyclyl-C2-C6- ydroxyalkylidenyl, hydroxycarbonyl-Ci-C6- ydrox- yalkyl, hydroxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl-Ci-C6- aloalkyl, Ci-C6-alkoxycar- bonyl-Ci-C6- ydroxyalkyl, Ci-C6- aloalkoxycarbonyl-Ci-C6- ydroxyalkyl, Ci-C6-alkoxycar- bonyl-Ci-C6- aloalkyl, Ci-C6- aloalkoxycarbonyl-Ci-C6- aloalkyl, Ci-C6-alkoxycarbonyl- Ci-C6-alkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-alkyl, C3-C6- ydroxycycloalkyl-Ci-C6- ydrox yalkyl, C3-C6- ydroxycycloalkenyl-Ci-C6- ydroxyalkyl, C3-C6- ydroxycycloalkyl-C3-C6- y- droxyalkenyl, C3-C6-hydroxycycloalkenyl-C3-C6-hydroxyalkenyl, C3-C6- ydroxycycloalkyl- C3-C6- ydroxyalkynyl, C3-C6-hydroxycycloalkenyl-C3-C6- ydroxyalkenyl, C2-C6-dihydroxy- alkyl, C3-C6-dihydroxyhaloalkyl, C4-C6-dihydroxyalkenyl, C4-C6-dihydroxyhaloalkenyl, C4- C6-dihydroxyalkynyl, Cs-Ce-dihydroxyhaloalkynyl, C4-C6-dihydroxycycloalkyl, C4-C6-dihy- droxyhalocycloalkyl, C4-C6-dihydroxycycloalkenyl, C4-C6-dihydroxyhalocycloalkenyl, C3- C6-cycloalkyl-C2-C6-dihydroxyalkyl, C3-C6- alocycloalkyl-C2-C6-dihydroxyalkyl, C3-C6-cy- cloalkenyl-C2-C6-dihydroxyalkyl, C3-C6- alocycloalkenyl-C2-C6-dihydroxyalkyl, C3-C6-cyclo alkyl-C3-C6-dihydroxyalkenyl, C3-C6- alocycloalkyl-C3-C6-dihydroxyalkenyl, C3-C6-cycloal- kenyl-C3-C6-dihydroxyalkenyl, C3-C6- alocycloalkenyl-C3-C6-dihydroxyalkenyl, C3-C6-cy- cloalkyl-C4-C6-dihydroxyalkynyl, C3-C6- alocycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-cyclo alkenyl-C4-C6-dihydroxyalkynyl, C3-C6- alocycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-cyclo- alkyl-C3-C6-dihydroxyalkylidenyl, C3-C6-halocycloalkyl-C3-C6-dihydroxyalkylidenyl, hetero- cyclyl-C3-C6-dihydroxyalkylidenyl, hydroxycarbonyl-C2-C6-dihydroxyalkyl, hydroxycarbonyl C3-C6-dihydroxyhaloalkyl, CrC6-alkoxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-haloal- koxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-haloalkoxycarbonyl-C3-C6-dihydroxyhaloalkyl, C3-C6-dihydroxycycloalkyl- Ci-C6-alkyl, C3-C6-dihydroxycycloalkyl- Ci-C6-haloalkylC3-C6- dihydroxycycloalkyl- C2-C6-alkenyl, C3-C6-dihydroxycycloalkyl- C2-C6- aloalkenyl, C3-C6- dihydroxycycloalkyl- C2-C6-alkynyl, C3-C6-dihydroxycycloalkyl- C3-C6- aloalkynyl, C1-C6- alkylcarbonyl-Ci-C6-alkyl, Ci-C6- aloalkylcarbonyl-Ci-C6-alkyl, Ci-C6-alkylcarbonyl-Ci-C6- haloalkyl, Ci-C6- aloalkylcarbonyl-Ci-C6- aloalkyl, hydroxycarbonyl-C2-C6-alkenyl, hy- droxycarbonyl-C2-C6- aloalkenyl, CrC6-alkoxycarbonyl-C2-C6-alkenyl, Ci-C6-haloalkoxy- carbonyl-C2-C6-alkenyl, CrC6-alkoxycarbonyl-C2-C6- aloalkenyl, Ci-C6-haloalkoxycar- bonyl-C2-C6- aloalkenyl, hydroxycarbonyl-C2-C6-alkynyl, hydroxycarbonyl-C3-C6-haloal- kynyl, Ci-C6-alkoxycarbonyl-C2-C6-alkynyl, Ci-C6-haloalkoxycarbonyl-C2-C6-alkynyl, Ci-Ce alkoxycarbonyl-C3-C6- aloalkynyl, Ci-C6- aloalkoxycarbonyl-C3-C6- aloalkynyl, Ci-C6-cy- anoalkyl, C2-C6-cyanohaloalkyl, Ci-C6-dicyanoalkyl, C2-C6-dicyanohaloalkyl, di(hy- droxycarbonyl)-Ci-C6-alkyl, di(hydroxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-alkoxycarbonyl) Ci-C6-alkyl, di(Ci-C6-haloalkoxycarbonyl)-Ci-C6-alkyl, di(Ci-C6-alkoxycarbonyl)-Ci-C6- haloalkyl, di(Ci-C6- aloalkoxycarbonyl)-CrC6-haloalkyl, di(Ci-C6-alkoxyl)phosphoryl-Cr C6-alkyl, di(CrC6- aloalkoxyl)phosphoryl-Ci-C6-alkyl, di(Ci-C6-alkoxyl)phosphoryl-Ci-C6- haloalkyl, di(Ci-C6- aloalkoxyl)phosphoryl-Ci-C6- aloalkyl, phosphoryl-Ci-C6-alkyl , phos- phoryl-Ci-C6-haloalkyl , di[di(Ci-C6-alkoxyl)phosphoryl-)]Ci-C6-alkyl, di[di(Ci-C6-haloal- koxyl)phosphoryl-)]Ci-C6-alkyl, di[di(Ci-C6-alkoxyl)phosphoryl-)]Ci-C6- aloalkyl, di[di(Ci- C6- aloalkoxyl)phosphoryl-)]Ci-C6-haloalkyl, diphosphoryl-Ci-C6-alkyl , diphosphoryl-Ci- Ce-haloalkyl, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6- aloalkylthio-Ci-C6-alkyl, Ci-C6-alkylthio- d-Ce-haloalkyl, Ci-C6-haloalkylthio-Ci-C6- aloalkyl, Ci-C6-alkylsulfinly-Ci-C6-alkyl, C C6- haloalkylsulfinly-CrC6-alkyl, Ci-C6-alkylsulfinly-CrC6-haloalkyl, Ci-C6-haloalkylsulfinly-Cr C6- aloalkyl, Ci-C6-alkylsulfonyl-Ci-C6-alkyl, Ci-C6- aloalkylsulfonyl-Ci-C6-alkyl, C1-C6- haloalkylsulfonyl-Ci-C6-haloalkyl, phenyl, 5- or 6-membered heteroaryl or 3- to 6-mem- bered heterocyclyl;
wherein hydroxy groups of R2 are unsubstituted or substituted by Rb;
cyclic groups of R2 are unsubstituted or substituted by Rc; and
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd.
Rb is d-Ce-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6- haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3-C6-halocy- cloalkenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-alkyl, Ci C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci-C6-haloalkyl, C1-C6- alkylcarbonyl, Ci-C6-haloalkylcarbonyl, hydroxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl- Ci-C6-haloalkyl, Ci-C6-alkyloxycarbonyl, Ci-C6-haloalkyloxycarbonyl, Ci-C6-alkylthio- carbonyl, Ci-C6-haloalkylthiocarbonyl, Ci-C6-alkylaminocarbonyl, Ci-C6-haloalkyla- minocarbonyl, Ci-C6-dialkylaminocarbonyl, Ci-C6-dihaloalkylaminocarbonyl, Ci-C6-al- kylsulfonyl, CrC6-haloalkylsulfonyl, Ci-C6-alkoxy-CrC6-alkyl, Ci-C6-haloalkoxy-Ci-C6- alkyl, Ci-C6-alkoxy-CrC6-haloalkyl, CrC6-haloalkoxy-Ci-C6-haloalkyl, phenyl-Ci-C6- alkyl, or phenyl-Ci-C6-haloalkyl;
Rc is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci-Ce- haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, or Ci-C6-alkylsulfonyl;
Rd is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent Rd is unsubstituted or substituted by Re;
Re is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci-Ce- haloalkoxy, Ci-C6-alkylsulfonyl;
Z is a 9 or 10 membered bicyclic ring comprising A;
A is C*, CR3, NR3A, N, O, or S;
C* is a bridge carbon of the bicyclic ring Z;
R3 is halogen, CN, CHO, N02, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloal- koxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, C1-C6- haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (C1-C6- alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted by substituents Ra;
R3A is H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C3- C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-CrC6-alkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci- C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloal- kyl)oxy, or phenyl;
wherein the cyclic groups of R3A are unsubstituted or substituted by Ra;
R4 is halogen, CN, CHO, N02, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloal- koxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, C1-C6- haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (C1-C6- alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R4 are unsubstituted or substituted by Ra;
Ra is halogen, CN, NO2, Ci-Ce-alkyl, Ci-Ce-haloalkyl, d-Ce-alkoxy, or d-Ce-haloalkoxy; m is 0, 1 , 2, or 3;
including agriculturally acceptable salts or derivatives of 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 compounds of formula (I) having an acidic functionality, as herbicide.
The pyridine compounds of formula (I) according to the invention can be prepared by standard processes of organic chemistry, e.g. by the following processes:
Process A:
The pyridine of formula (II) can be obtained by reacting respective pyridines of formula (I) , with R2 = CH3, with base and an electrophile, e.g. a carbonyl compound (III):
Figure imgf000006_0001
The reaction of the pyridine (I) with the electrophile (III), with R independent of each other equals hydrogen, alkyl, cycloalkyl, halocycloalkyl, haloalkyl, cycloalkenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl or both R form together a carbocy- cle or a heterocycle, is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 20 °C, particularly preferably from -80 °C to -20 °C , in an inert organic solvent in the presence of a base.
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, tert-butyl methyl ether (TBME), dioxane, anisole and tet- rahydrofuran (THF), and also dimethyl sulfoxide (DMSO), dimethylformamide (DMF) and dime- thylacetamide (DMAC), particularly preferably diethyl ether, dioxane and THF.
It is also possible to use mixtures of the solvents mentioned.
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 bases, e.g. 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 diisopropylamide (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, based on the pyridine compounds (I).
Figure imgf000006_0002
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, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably toluene and o-xylene.
It is also possible to use mixtures of the solvents mentioned.
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.
Figure imgf000007_0001
The oxidation of the olefin (IV) to the diol (V) is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from 0 °C to 120 °C, particularly preferably from 20 °C to 100 °C, in an inert solvent.
The reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (IV) with the oxidant in an organic solvent.
Suitable in principle are all solvents which are capable of dissolving the pyridines (IV) and the oxidant at least partly and preferably fully under the reaction conditions.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Cs-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably TBME, THF It is also possible to use mixtures of the solvents mentioned.
Suitable oxidants are e.g. potassium permanganate, potassium perruthenate, osmium tetrox- ide and other osmium salts, like potassium osmate. The oxidant can be used in equimolar amounts or in catalytic amounts together with a reoxidant like N-methylmorpholine-N-oxide or potassium hexacyanoferrate in stochiometric amounts or in excess.
Figure imgf000007_0002
The pyridine compounds of formula (I), with R2 = hydrogen or alkyl, can be obtained by reacting boronic acids or esters with halides of formula (VI) in which X equals CI, Br, or I in presence of a base and a catalyst in analogy to WO 2014202493.
The reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (VI) with the boronic acid or ester in an organic solvent with or without water as co-solvent. Suitable in principle are all solvents which are capable of dissolving the pyridines (VI) and the boronic acid or ester at least partly and preferably fully under the reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, 0-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, tert. -butyl methylether (TBME), dioxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2-imidaz- olidinone (DMI), Ν,Ν'-dimethylpropylene urea (DMPU), DMSO and NMP.
It is also possible to use mixtures of the solvents mentioned.
Examples of suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3; alkali metal and alkaline earth metal oxide, and other metal oxides, such as U2O, Na20, K2O, MgO, and CaO, Fe2C>3, Ag2<D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC , as well as alkali metal bicarbonates such as IJHCO3, NaHCC , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P04)2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
The term 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 (VI), more pref- erably from 1.0 to 5.0 equivalents based on the pyridine (VI), most preferably from 1.2 to 2.5 equivalents based on the pyridine (VI).
It may be advantageous to add the base offset over a period of time.
The reaction of the pyridines (VI) with the phenyl boronic acid or ester is carried out in the presence of a catalyst. Examples of suitable catalysts include e.g., palladium based catalysts like, e.g., Palladium(ll)acetate, tetrakis(triphenylphosphine)palladium(0), bis(tri- phenylphosphine)palladium(ll)chloride, or (1 ,1 ,-bis(diphenylphosphino)ferrocene)-dichloropalla- dium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, tri- phenylphosphine, or BINAP (2,2'-Bis(diphenylphospino)-1 ,1 '-binaphthyl).
The amount of catalyst is usually 0.01 to 10 mol % (0.0001 to 0.1 equivalents) based on the pyridine (VI).
The halopyridines VI, with R2 = hydrogen or alkyl, are known or can be prepared by known procedures (X=CI, Br, I).
The boronic acids or esters required for the preparation of pyridine compounds of formula (I), with R2 = hydrogen, alkyl or alkoxycarbonyl, 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 pyridine compounds of formula (VII) can be obtained by reacting respective pyridines of formula (I), with R2 = H, with base and an electrophile, e.g. a carbonyl compound (III):
Figure imgf000008_0001
The reaction of the pyridine (I) with the electrophile (III), with R independent of each other equals hydrogen, alkyl, cycloalkyl, halocycloalkyl, haloalkyl, cycloalkenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl, heteroaryl or both R form together a carbocy- cle or a heterocycle, is usually carried out at temperatures from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 20 °C, particularly preferably from -80 °C to -20 °C, in an inert organic solvent in the presence of a base.
Suitable solvents are aliphatic hydrocarbons, such as pentane, hexane, cyclohexane and mixtures of Cs-Ce-alkanes, aromatic hydrocarbons, such as toluene, o-, m- and p-xylene, ethers, such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and THF, and also DMSO, DMF and DMAC, particularly preferably diethyl ether, dioxane and THF.
It is also possible to use mixtures of the solvents mentioned.
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 lithium diiso- propylamide, lithium hexamethyidisilazide, lithium 2,2,6,6-tetramethylpiperidide, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi , 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. tertiary amines, such as trimethylamine (TEA), triethylamine (TMA), diiso- propylethylamine (DIPEA) and N-methylpiperidine, pyridine, substituted pyridines, such as col- lidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to sodium hydride, lithium 2,2,6,6-tetramethylpiperidide and lithium diisopropylamide (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, based on the pyridine (I). Process B:
Figure imgf000009_0001
Pyridine compounds (VIII), with R equals alkyl, haloalkyl, alkoxy or haloalkoxy, can be ob- tained by reacting respective pyridine compounds of formula (IX) with base and an electrophile (X).
Electrophile (X) can be an alkyl-, alkenyl- or alkynyl-halide, e.g. methyl iodide, allyl bromide or propargyl bromide, or a halogenating agent, e.g. CI2, Br2, I2, NCS (/V-Chlorosuccinimide), NBS (/V-Bromosuccinimide), NIS (/V-lodosuccinimide), NFSI (N-Fluorobenzenesulfonimide), Select- fluor (1-Chloromethyl-4-fluoro-1 ,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)).
The reaction of the pyridine (IX) with the electrophile is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 80 °C, particularly preferably from -80 °C to 30 °C, in an inert organic solvent in the presence of a base. Suitable in principle are all solvents which are capable of dissolving the pyridine (IX) and the electrophile (X) at least partly and preferably fully under the reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, 1 ,3-dimethyl-2-imidazolidinone (DMI), Ν,Ν'- dimethylpropylene urea (DMPU), and NMP.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2Hs, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g. tertiary amines, such as TMA, TEA, DIPEA and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to NaH, lithium hexamethyldisilazide and LDA.
The bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile (X), based on the pyridine
(IX).
The pyridine compounds of formula (XI), with R equals alkyl, haloalkyl, alkenyl, alkynyl, cyclo- alkyl, phenyl, heterocyclyl, heteroaryl or dialkylamino, can be obtained by reacting respective pyridines of formula (I), with R2 = CH3, with base and an electrophile (XII), e.g. a dialkylcar- bonate (X = R = alkoxy), an alkyl chloroformiate (X = halogene, R = alkoxy) or an acid halide (X = halogene, R = alkyl or haloalkyl) :
Figure imgf000010_0001
The reaction of the pyridine (I) with the electrophile (XII) is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -80 °C to 80 °C, par- ticularly 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 (XII) at least partly and preferably fully under the reaction conditions.
Examples of 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, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
It is also possible to use mixtures of the solvents mentioned.
Suitable bases are, in general, inorganic compounds, such as alkali metal and alkaline earth metal anhydrides, such as LiH, NaH, KH and CaH, alkali metal amides, such as LHMDS and LDA, organometallic compounds, in particular alkali metal alkyls, such as MeLi, BuLi and PhLi, and also alkali metal and alkaline earth metal alkoxides, such as NaOCH3, NaOC2Hs, KOC2H5, tBuOK, potassium tert-pentoxide and dimethoxymagnesium, moreover organic bases, e.g. tertiary amines, such as TMA, TEA, DIPEA and N-methylpiperidine, pyridine, substituted pyridines, such as collidine, lutidine and 4-dimethylaminpyridine, and also bicyclic amines. Particular preference is given to NaH, lithium hexamethyldisilazide and LDA.
The bases are generally employed in equimolar amounts; however, they can also be employed in catalytic amounts, in excess or, if appropriate, as solvents.
The starting materials are generally reacted with one another in equimolar amounts. It may be advantageous to employ an excess of base and/or the electrophile (XII), based on the pyridine
(I)-
Process C:
The pyridines of formula (XIV) can be obtained by reacting respective pyridines of formula (XIII) with a reducing agent such as LAH or DIBAIH.
Figure imgf000011_0001
The reduction of pyridines (XIII) 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, 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 diethyl ether, dioxane and THF.
It is also possible to use mixtures of the solvents mentioned.
Examples of reducing agents for pyridines (XIII) include LAH, DIBALH, LiBH4 or Lithium tri- ethylborohydride.
Preferred agents include LAH and DIBALH.
The hydride-source is used preferably from 1 to 10 equivalents based on the pyridine (XIII), more preferably from 1.0 to 5.0 equivalents based on the pyridine (XIII), most preferably from 1.2 to 2.5 equivalents based on the pyridine (XIII).
The end of the reaction can easily be determined by the skilled worker by means of routine methods.
The 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.
If the intermediates and the end products are obtained as solid, purification can also be carried out by recrystallization or digestion.
The pyridines of formula (XIII) can be obtained by reacting respective pyridines of formula (XV) with boronic acids/esters of formula (XVI):
Figure imgf000012_0001
The reaction of pyridines (XV) with boronic acids/esters (XVI) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly preferably from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst. The reaction may in principle be carried out in substance. However, preference is given to reacting the pyridines (XV) with the boronic acids/esters (XVI) in an organic solvent with or without water as co-solvent.
Suitable in principle are all solvents which are capable of dissolving the pyridines (XV) and the boronic acids (XVI) at least partly and preferably fully under the reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, DMSO and NMP.
It is also possible to use mixtures of the solvents mentioned.
Examples of 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, Ag20; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, Cs2C03, MgC03, and CaC03, as well as alkali metal bicarbonates such as LiHC03, NaHC03, KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P04)2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
The term 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 (XV), more preferably from 1.0 to 5.0 equivalents based on the pyridine (XV), most preferably from 1.2 to 2.5 equivalents based on the pyridine (XV).
It may be advantageous to add the base offset over a period of time.
The reaction of the pyridines (XV) with the boronic acids/esters (XVI) is carried out in the pres- ence of a catalyst. Examples of 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 (XV).
The halopyridines XV are known from the literature (e.g. WO 201 1 154327), are commercially available or can be prepared by known procedures. The boronic acids/esters XVI required for the preparation of pyridines of formula (XIII) 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).
Process D:
The pyridines of formula (XVII) can be obtained by reacting respective pyridines of formula (XIII) with a metal organic species like a Grignard reagent (R'MgX, X = CI, Br, I; R' = alkyl, cy- cloalkyl, halocycloalkyl, haloalkyl, cycloalkenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl or heteroaryl).
Figure imgf000013_0001
The reaction of pyridines (XIII) 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.
It is also possible to use mixtures of the solvents mentioned.
Examples of metal organic species for the synthesis of pyridines (XVII) are Grignard reagents like R'MgCI, R'MgBr or R'Mgl, lithium organic species, aluminum organic species like R'sAI, R'2AIX and R'AIX2, titanium organic species like R'4Ti, R'3TiX, R'2TiX2 and RTiX3,
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 (XIII), more preferably from 2.0 to 5.0 equivalents based on the pyridine (XIII), most preferably from 2.0 to 3.0 equivalents based on the pyridine (XIII).
Process E:
The pyridines of formula (XIX) can be obtained by reacting respective pyridines of formula (XVIII) with a metal organic species like a Grignard reagent (R'MgX, X = CI, Br, I; R' = alkyl, cy- cloalkyl, halocycloalkyl, haloalkyl, cycloalkenyl, halocycloalkenyl, alkenyl, haloalkenyl, alkynyl, phenyl, heterocyclyl or heteroaryl).
Figure imgf000013_0002
The reaction of pyridines (XVIII) 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.
It is also possible to use mixtures of the solvents mentioned.
Examples of metal organic species for the synthesis of pyridines (XIX) are Grignard reagents like R'MgCI, R'MgBr or R'Mgl, lithium organic species, aluminum organic species like R'sAI, R'2AIX and R'AIX2, titanium organic species like R'4Ti, R'3TiX, R'2TiX2 and RTiX3,
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 (XVIII), more preferably from 2.0 to 5.0 equivalents based on the pyridine (XVIII), most preferably from 2.0 to 3.0 equivalents based on the pyridine (XVIII).
The pyridines of formula (XVIII) can be obtained by oxidizing respective pyridines of formula (XI
Figure imgf000014_0001
The oxidation of pyridines (XIV) 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 (XIV) in an organic solvent.
Suitable in principle are all solvents which are capable of dissolving the pyridines (XIV) at least partly and preferably fully under the reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, halogenated hydrocarbons such as CH2CI2, CHCI3, CCH2CICH2CI or CCI4, ethers such as diethyl ether, diisopropyl ether, TBME, dioxane, anisole and tetrahydrofuran (THF), as well as dipolar aprotic solvents such as sulfolane, DMF, DMAC, DMI, DMPU, DMSO and NMP.
It is also possible to use mixtures of the solvents mentioned.
Examples of oxidizing agents for the synthesis of pyridines (XIV) are metal oxides such as Mn02, KMn04, CrC or PCC, and non-metal oxides such as NaCIO, Nal04 or pyridine/SO-3 - complex. In addition methods like the Swern oxidation or the TEMPO oxidation known to a person skilled in the art can be used to obtain pyridines of formula (XVIII).
Preferred agents include Mn02, KMn04 and PCC, more preferred Mn02.
The oxidizing agent is used preferably from 1 to 50 equivalents based on the pyridine (XIV), more preferably from 1.0 to 20.0 equivalents based on the pyridine (XIV), most preferably from 1.0 to 10.0 equivalents based on the pyridine (XIV).
Process F:
The pyridines of formula (XXI; Q = cycloalkyl, halocycloalkyl, alkyl, haloalkyl, alkenyl, alkynyl, phenyl, heteroaryl, heterocyclyl, alkylidenyl or halo alkylidenyl and R' = alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl, heterocyclyl, alkoxycarbonylalkyl) can be obtained reacting respective pyridines of formula (XX) with base and an electrophile.
Figure imgf000015_0001
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 (XX) with the electrophile is usually carried out at temperatures of from -100 °C to the boiling point of the reaction mixture, preferably from -20 °C to 100 °C, particularly preferably from 0 °C to 30 °C, in an inert organic solvent in the presence of a base. Suitable in principle are all solvents which are capable of dissolving the pyridine (XX) and the electrophile at least partly and preferably fully under the reaction conditions.
Examples of suitable solvents are aromatic hydrocarbons such as benzene, chlorobenzene, toluene, cresols, o-, m- and p-xylene, ethers such as diethyl ether, diisopropyl ether, TBME, di- oxane, anisole and THF, nitriles such as acetonitrile and propionitrile, as well as dipolar aprotic solvents such as sulfolane, DMSO, DMF, DMAC, DMI, DMPU, and NMP.
It is also possible to use mixtures of the solvents mentioned.
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. 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 em- ployed 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 (XX). Process G:
The pyridines of formula (I) can also be obtained by reacting respective pyridines of formula (XXII), obtained e.g. in analogy to Synlett, (5), 808-810, 2002, with boronic acids/esters of formula (XXIII):
Figure imgf000015_0002
The reaction of pyridines (XXII) with boronic acids/esters (XXIII) is usually carried out from 0 °C to the boiling point of the reaction mixture, preferably from 15 °C to 1 10 °C, particularly preferably from 40 °C to 100 °C, in an inert organic solvent in the presence of a base and a catalyst.
The reaction may in principle be carried out in substance. However, preference is given to re- acting the pyridines (XXII) with the boronic acids/esters (XXIII) in an organic solvent with or without water as co-solvent.
Suitable in principle are all solvents which are capable of dissolving the pyridines (XXII) and the boronic acids (XXIII) at least partly and preferably fully under the reaction conditions.
Examples of 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.
It is also possible to use mixtures of the solvents mentioned.
Examples of suitable metal-containing bases are inorganic compounds including metal-con- taining bases such as alkali metal and alkaline earth metal hydroxides, and other metal hydroxides, such as LiOH, NaOH, KOH, Mg(OH)2, Ca(OH)2 and AI(OH)3; alkali metal and alkaline earth metal oxide, and other metal oxides, such as Li20, Na20, K20, MgO, and CaO, Fe2C>3, Ag2<D; alkali metal and alkaline earth metal carbonates such as U2CO3, Na2CC>3, K2CO3, CS2CO3, MgCC>3, and CaCC , as well as alkali metal bicarbonates such as LiHCC>3, NaHCC , KHCO3; alkali metal and alkaline earth metal phosphates such as K3PO4, Ca3(P04)2; alkali metal and alkaline earth metal acetates such as sodium acetate or potassium acetate.
The term 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 (XXII), more preferably from 1 .0 to 5.0 equivalents based on the pyridine (XXII), most preferably from 1 .2 to 2.5 equivalents based on the pyridine (XXII).
It may be advantageous to add the base offset over a period of time.
The reaction of the pyridines (XXII) with the boronic acids/esters (XXIII) is carried out in the presence of a catalyst. Examples of suitable catalysts include e.g., palladium based catalysts like, e.g., palladium(ll)acetate, tetrakis(triphenylphosphine)- palladium(O), bis(tri- phenylphosphine)palladium(ll)chloride or (1 ,1 ,-bis(diphenylphosphino)- ferrocene)-dichloropalla- dium(ll), and optionally suitable additives such as, e.g., phosphines like, e.g., P(o-tolyl)3, tri- phenylphosphine 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 (XXII).
The end of the reaction can easily be determined by the skilled worker by means of routine methods.
The 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.
If the intermediates and the end products are obtained as solid, purification can also be carried out by recrystallization or digestion. The boronic acids/esters (XXIII) required for the preparation of pyridines of formula (I) are commercially available, known from literature or can easily prepared analogously to published procedures (e.g. Kamei et al. Tetrahedron Lett. 2014, 55, 4245 - 4247). The present invention also provides agrochemical compositions comprising at least one pyridine compounds of formula (I) and auxiliaries customary for formulating crop protection agents.
The present invention furthermore provides a method for controlling unwanted vegetation where a herbicidal effective amount of at least one pyridine compounds of formula (I) is allowed to act on plants, their seeds and/or their habitat. Application can be done before, during and/or after, preferably during and/or after, the emergence of the undesirable plants.
Further embodiments of the present invention are evident from the claims, the description and the examples. It is to be understood that the features mentioned above and still to be illustrated below of the subject matter of the invention can be applied not only in the combination given in each particular case but also in other combinations, without leaving the scope of the invention. As used herein, the terms "controlling" and "combating" are synonyms.
As used herein, the terms "undesirable vegetation" and "harmful plants" are synonyms.
If the pyridine compounds of formula (I) as described herein are capable of forming geomet- rical 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.
If the 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.
If the 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, tetrabutylammonium, 2-hydroxyethylammonium (olamine salt), 2-(2-hydroxy- eth-1 -oxy)eth-1-ylammonium (diglycolamine salt), di(2-hydroxyeth-1-yl)ammonium (diolamine salt), tris(2-hydroxy-ethyl)ammonium (trolamine salt), tris(2-hydroxypropyl)ammonium, benzyltri- methylammonium, benzyltriethylammonium, Ν,Ν,Ν-trimethylethanolammonium (choline salt), furthermore phosphon-ium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, such as tri- methylsulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium, and finally the salts of polybasic amines such as N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, iodide, 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. as 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. Preferred 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 R1, R2, A, Z, R3, R3A, and R4 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 Cn-Cm denoting in each case the possible number of carbon atoms in the group.
Examples of such meanings are:
- CrC4-alkyl: e.g. CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2H5, CH2-CH(CH3)2, and C(CH3)3;
Ci-C6-alkyl: Ci-C4-alkyl as mentioned above, and also, e.g., n-pentyl, 1-methylbutyl, 2- methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1 -ethylpropyl, n-hexyl, 1 ,1 -dimethylpropyl, 1 ,2- dimethylpropyl, 1 -methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1-dimethyl- butyl, 1 ,2-dimethylbutyl, 1 ,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethyl- butyl, 1-ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-tri methyl propyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpro- pyl or 1 -ethyl-2-methylpropyl, preferably methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1 ,1-di- methylethyl, n-pentyl, or n-hexyl;
Ci-C4-haloalkyl: Ci-C4-alkyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g., chloromethyl, dichloromethyl, trichloromethyl, flu- oromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluo- romethyl, bromomethyl, iodomethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2- difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoro- propyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3- bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, hep- tafluoro-propyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, l-(bromomethyl)- 2-bromo-ethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, nonafluorobutyl, 1 ,1 ,2,2,-tetrafluoro- ethyl, and 1 -trifluoromethyl-1 ,2,2,2-tetrafluoroethyl;
Ci-C6-haloalkyl: Ci-C4-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;
C3-C6-cycloalkyl: monocyclic saturated hydrocarbons having 3 to 6 ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl;
C3-C6-alkenyl: e.g. 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-bu- tenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl, 1- pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1 -butenyl, 2-methyl-1 -butenyl, 3-methyl-
1- butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl,
2- methyl-3-butenyl, 3-methyl-3-butenyl, 1 ,1-dimethyl-2-propenyl, 1 ,2-dimethyl-1-propenyl, 1 ,2- dimethyl-2-propenyl, 1-ethyl-1 -propenyl, 1 -ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4- hexenyl, 5-hexenyl, 1-methyl-1 -pentenyl, 2-methyl-1 -pentenyl, 3-methyl-1-pentenyl, 4-methyl-1- pentenyl, 1 -methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,
1- methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1 -methyl- 4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1 ,1-dimethyl-2-bu- tenyl, 1 ,1-dimethyl-3-butenyl, 1 ,2-dimethyl-1 -butenyl, 1 ,2-dimethyl-2-butenyl, 1 ,2-dimethyl-3-bu- tenyl, 1 ,3-dimethyl-1-butenyl, 1 ,3-dimethyl-2-butenyl, 1 ,3-dimethyl-3-butenyl, 2,2-dimethyl-3-bu- tenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-bu- tenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1 -ethyl-3-butenyl, 2-ethyl-1- butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1 ,1 ,2-trimethyl-2-propenyl, 1 -ethyl-1-methyl-2-pro- penyl, 1-ethyl-2-methyl-1-propenyl, and 1 -ethyl-2-methyl-2-propenyl;
C3-C6-haloalkenyl: a C3-C6-alkenyl substituent as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, e.g. 2-chloroprop-2-en-1-yl, 3-chlo- roprop-2-en-1 -yl, 2,3-dichloroprop-2-en-1 -yl, 3,3-dichloroprop-2-en-1-yl, 2,3,3-trichloro-2-en-1-yl, 2,3-dichlorobut-2-en-1-yl, 2-bromoprop-2-en-1-yl, 3-bromoprop-2-en-1-yl, 2,3-dibromoprop-2- en-1-yl, 3,3-dibromoprop-2-en-1 -yl, 2,3,3-tribromo-2-en-1-yl, or 2,3-dibromobut-2-en-1 -yl;
C3-C6-alkynyl: e.g. 1-propynyl, 2-propynyl, 1 -butynyl, 2-butynyl, 3-butynyl, 1-methyl-2- propynyl, 1 -pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl,
2- methyl-3-butynyl, 3-methyl-1-butynyl, 1 ,1 -dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1 -methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl- 4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1 ,1-dimethyl-2-butynyl, 1 ,1 -dimethyl-3-butynyl, 1 ,2- dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3- butynyl, 2-ethyl-3-butynyl, and 1-ethyl-1 -methyl-2-propynyl;
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-methylpropoxy.
Ci-C4-haloalkoxy: a Ci-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., 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-chloropropoxy, 2-bromo- propoxy, 3-bromopropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3- trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1- (fluoromethyl)-2-fluoroethoxy, 1 -(chloromethyl)-2-chloroethoxy, 1 -(bromomethyl)-2-bromoeth- oxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, and nonafluorobutoxy;
Ci-C6-haloalkoxy: a Ci-C4-haloalkoxy as mentioned above, and also, e.g., 5-fluoro- pentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluoro- hexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy and dodecafluorohexoxy;
Ci-C4-alkylthio: e.g. methylthio, ethylthio, propylthio, 1 -methylethylthio, butylthio, 1- methylpropylthio, 2-methylpropylthio, and 1 ,1-dimethylethylthio;
Ci-C6-alkylthio: Ci-C4-alkylthio as mentioned above, and also, e.g., pentylthio, 1 -methyl- butylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hex- ylthio, 1 ,1 -dimethylpropylthio, 1 ,2-dimethylpropylthio, 1 -methylpentylthio, 2-methylpentylthio, 3- methylpentylthio, 4-methylpentylthio, 1 ,1-dimethylbutylthio, 1 ,2-dimethylbutylthio, 1 ,3-dimethyl- butylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1 -ethylbutylthio, 2- ethylbutylthio, 1 , 1 ,2-trimethylpropylthio, 1 ,2,2-trimethylpropylthio, 1 -ethyl-1 -methylpropylthio, and 1- ethyl-2-methylpropylthio;
(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 -ethylbutylamino, 2-ethylbutylamino, 1 ,1 ,2-trimethyl- propylamino, 1 ,2,2-trimethyl-propylamino, 1 -ethyl-1 -methylpropylamino, or 1-ethyl-2-methylprop ylamino;
di(Ci-C4-alkyl)amino: e.g. N,N-dimethylamino, Ν,Ν-diethylamino, N,N-di(1-methyl- ethyl)amino, N,N-dipropylamino, Ν,Ν-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-dimethylethyl)-N-methylamino, N-ethyl-N- propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(l-methylpropyl) amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1 ,1 -dimethylethyl)amino, N-(l-methylethyl) N-propylamino, N-butyl-N-propylamino, N-(1 -methylpropyl)-N-propylamino, N-(2-methylpropyl)- N-propylamino, N-(1 ,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1 -me- thyl-ethyl)-N-(1-methyl-propyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(1 ,1-di- methylethyl)-N-(1 -methylethyl)amino, N-butyl-N-(1 -methylpropyl)amino, N-butyl-N-(2-methylpro- pyl)amino, N-butyl-N-(1 ,1-dimethylethyl)amino, N-(1 -methylpropyl)-N-(2-methylpropyl)amino, N- (1 ,1-dimethyl-ethyl)-N-(1-methylpropyl)amino, or N-(1 ,1-dimethylethyl)-N-(2-methylpropyl)amino; di(Ci-C6-alkyl)amino: di(Ci-C4-alkyl)amino as mentioned above, and also, e.g., N-me- thyl-N-pentylamino, N-methyl-N-(1-methylbutyl)amino, N-methyl-N-(2-methylbutyl)amino, N-me- thyl-N-(3-methylbutyl)amino, N-methyl-N-(2,2-dimethylpropyl)amino, N-methyl-N-(1 -ethylpro- pyl)amino, N-methyl-N-hexylamino, N-methyl-N-(1 ,1-dimethylpropyl)amino, N-methyl-N-(1 ,2-di- methylpropyl)amino, N-methyl-N-(1-methylpentyl)amino, N-methyl-N-(2-methylpentyl)amino, N- methyl-N-(3-methylpentyl)amino, N-methyl-N-(4-methylpentyl)amino, N-methyl-N-(1 ,1-dimethyl- butyl)amino, N-methyl-N-(1 ,2-dimethylbutyl)amino, N-methyl-N-(1 ,3-dimethylbutyl)amino, N-me- thyl-N-(2,2-dimethylbutyl)amino, N-methyl-N-(2,3-dimethylbutyl)amino, N-methyl-N-(3,3-dime- thylbutyl)amino, N-methyl-N- (l-ethylbutyl)amino, N-methyl-N-(2-ethylbutyl)amino, N-methyl-N- (1 ,1 ,2-trimethylpropyl)amino, N-methyl-N- (1 ,2,2-trimethylpropyl)amino, N-methyl-N-(1-ethyl-1- methylpropyl)amino, N-methyl-N- (1-ethyl-2-methylpropyl)amino, N-ethyl-N-pentylamino, N- ethyl-N-(1 -methylbutyl)amino, N-ethyl-N-(2-methylbutyl)amino, N-ethyl-N-(3-methylbutyl)amino, N-ethyl-N-(2,2-dimethylpropyl)amino, N-ethyl-N-(1-ethylpropyl)amino, N-ethyl-N-hexylamino, N- ethyl-N-(1 ,1 -dimethylpropyl)amino, N-ethyl-N-(1 ,2-dimethylpropyl)amino, N-ethyl-N-(1- methylpentyl)amino, N-ethyl-N-(2-methylpentyl)amino, N-ethyl-N-(3-methylpentyl)amino, N- ethyl-N-(4-methylpentyl)amino, N-ethyl-N-(1 ,1-dimethylbutyl)amino, N-ethyl-N-(1 ,2-dimethyl- butyl)amino, N-ethyl-N-(1 ,3-dimethylbutyl)amino, N-ethyl-N-(2,2-dimethylbutyl)amino, N-ethyl-N- (2,3-dimethylbutyl)amino, N-ethyl-N-(3,3-dimethylbutyl)amino, N-ethyl-N-(1-ethylbutyl)amino, N- ethyl-N-(2-ethylbutyl)amino, N-ethyl-N-(1 ,1 ,2-trimethylpropyl)amino, N-ethyl-N-(1 ,2,2-trime- thylpropyl)amino, N-ethyl-N-(1 -ethyl-1-methylpropyl)amino, N-ethyl-N-(1 -ethyl-2-methylpro- pyl)amino, N-propyl-N-pentylamino, N-butyl-N-pentylamino, Ν,Ν-dipentylamino, N-propyl-N-hex- ylamino, N-butyl-N-hexylamino, N-pentyl-N-hexylamino, or N,N-dihexylamino;
Ci-C6-alkylsulfinyl (Ci-C6-Alkyl-S(=0)-): e.g. methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1- methylethylsulfinyl, butylsulfinyl, 1 -methylpropylsulfinyl, 2-methylpropylsulfinyl, 1 ,1-di- methylethylsulfinyl, pentylsulfinyl, 1 -methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfi- nyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1 ,1-dimethylpropylsulfinyl, 1 ,2-dimethylpro- pyl-sulfinyl, hexylsulfinyl, 1 -methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4- methylpentyl-sulfinyl, 1 ,1-dimethylbutylsulfinyl, 1 ,2-dimethylbutylsulfinyl, 1 ,3-dimethylbutyl-sulfi- nyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutyl-sulfinyl, 1-ethylbutyl- sulfinyl, 2-ethylbutylsulfinyl, 1 ,1 ,2-trimethylpropylsulfinyl, 1 ,2,2-trimethylpropylsulfinyl, 1 -ethyl-1 - methylpropyl-sulfinyl, and 1 -ethyl-2-methylpropylsulfinyl;
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- ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpen- tylsulfonyl, 4-methylpentylsulfonyl, 1 ,1 -dimethylbutylsulfonyl, 1 ,2-dimethylbutylsulfonyl, 1 ,3-di- methylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutyl-sul- fonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1 ,1 ,2-trimethyl-propylsulfonyl, 1 ,2,2-trimethyl- propylsulfonyl, 1 -ethyl-1 -methylpropylsulfonyl, and 1 -ethyl-2-methylpropylsulfonyl;
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;
bicyclic ring: a 9- to 10-membered bicyclic ring: a partially or fully unsaturated 9- to 10- membered carbocyclic system wherein two partially or fully unsaturated carbocyclic rings are fused with each other through 2 ring members, and which in addition to carbon atoms and independent of their position in the ring can comprise as ring members 1 to 4 nitrogen atoms, or 1 or 2 oxygen atoms, or 1 or 2 oxygen atoms and 1 to 2 nitrogen atoms, or 1 or 3 sulfur atoms, or 1 to 4 nitrogen atoms and an oxygen atom, or one to three nitrogen atoms and a sulfur atom, or one sulfur and one oxygen atom, examples of such bicyclic ring are, 2,3-dihydrobenzothio- phene, benzothiophene, 2,3-dihydrobenzofuran, benzofuran, 1 ,3-benzodioxole, 1 ,3-benzodithi- ole, 1 ,3-benzoxathiole, indole, indane, [1 ,3]dioxolo[4,5-c]pyridine, [1 ,3]dioxolo[4,5-b]pyridine, 2,3-dihydrofuro[2,3-c]pyridine, furo[2,3-c]pyridine, 2,3-dihydrofuro[2,3-b]pyridine, furo[2,3-b]pyri- dine, 2,3-dihydrofuro[3,2-c]pyridine, furo[3,2-c]pyridine, 2,3-dihydrofuro[3,2-b]pyridine, furo[3,2- b]pyridine, furo[3,2-d]pyrimidine, furo[2,3-d]pyrimidine, 6,7-dihydrofuro[3,2-d]pyrimidine, 5,6-di- hydrofuro[2,3-d]pyrimidine, thieno[3,2-d]pyrimidine, thieno[2,3-d]pyrimidine, 6,7-dihy- drothieno[3,2-d]pyrimidine, 5,6-dihydrothieno[2,3-d]pyrimidine, 2,3-dihydrothieno[2,3-c]pyridine, thieno[2,3-c]pyridine, 2,3-dihydrothieno[2,3-b]pyridine, thieno[2,3-b]pyridine, 2,3-dihy- drothieno[3,2-c]pyridine, thieno[3,2-c]pyridine, 2,3-dihydrothieno[3,2-b]pyridine, thieno[3,2-b]pyr- idine, 1 H-pyrrolo[2,3-c]pyridine, 1 H-pyrrolo[2,3-b]pyridine, 1 H-pyrrolo[3,2-c]pyridine, 1 H-pyr- rolo[3,2-b]pyridine, 1 H-imidazo[4,5-c]pyridine, 1 H-imidazo[4,5-b]pyridine, 3H-imidazo[4,5-c]pyri- dine, 3H-imidazo[4,5-b]pyridine, 1 H-pyrazolo[3,4-b]pyridine, 1 H-pyrazolo[3,4-c]pyridine, 1 H-py- razolo[4,3-b]pyridine, 1 H-pyrazolo[4,3-c]pyridine, 1 H-indazole, benzimidazole, 1 ,2-benzoxazole, 1 ,3-benzoxazole, 1 ,3-benzothiazole, 1 ,2-benzothiazole, naphthalene, quinolone, isoquinoline, quinazoline, 1 ,3-benzoxathiole, [1 ,3]oxathiolo[4,5-b]pyridine, [1 ,3]oxathiolo[4,5-c]pyridine,
[1 ,3]oxathiolo[5,4-c]pyridine, [1 ,3]oxathiolo[5,4-b]pyridine, 2,3-dihydro-1 ,4-benzodioxine, 2,3-di- hydro-[1 ,4]dioxino[2,3-b]pyridine, 2,3-dihydro-[1 ,4]dioxino[2,3-c]pyridine;
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-isothiazoli- dinyl, 1 -pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazoli- dinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 1 -imidazolidinyl, 2-imidazoli- dinyl, 4-imidazolidinyl, 3-oxazolidinyl, 1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 3-thiazol- idinyl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5-yl, 1 ,2,4-triazolidin-3-yl, 1 ,2,4-oxadiazolidin- 2-yl, 1 ,2,4-oxadiazolidin-4-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,2,4-thiadiazolidin-2-yl, 1 ,2,4-thiadiazoli- din-4-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,2,4-triazolidin-1-yl, or 1 ,3,4-triazolidin-2-yl;
5- membered partial unsaturated heterocycles like 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4- dihydrofur-2-yl, 2,4-dihydrofur-3-yl, dioxolan-2-yl, 1 ,3-dioxol-2-yl, 2,3-dihydrothien-2-yl, 2,3-dihy- drothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 4,5-dihydropyrrol-1 -yl, 4,5-dihydro- pyrrol-2-yl, 4,5-dihydropyrrol-3-yl, 2,5-dihydropyrrol-1 -yl, 2,5-dihydropyrrol-2-yl, 2,5-dihydro- pyrrol-3-yl, 2,3-dihydroisoxazol-1-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihy- droisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 4,5-dihydroisoxazol-2-yl, 4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol- 5-yl, 2,3-dihydroisothiazol-1 -yl, 2,3-dihydroisothiazol-3-yl, 2,3-dihydroisothiazol-4-yl, 2,3-dihy- droisothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol-5- yl, 4,5-dihydroisothiazol-1 -yl, 4,5-dihydroisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydroi- sothiazol-5-yl, 2,3-dihydropyrazol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihy- dropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4- dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydroimidazol-1-yl, 2,3-dihydroimidazol-2- yl, 2,3-dihydroimidazol-3-yl ,2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimid- azol-1-yl, 4,5-dihydroimidazol-2-yl, 4,5-dihydroimidazol-4-yl, 4,5-dihydroimidazol-5-yl, 2,5-dihy- droimidazol-1-yl, 2,5-dihydroimidazol-2-yl, 2,5-dihydroimidazol-4-yl, 2,5-dihydroimidazol-5-yl,
2.3- dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl,
3.4- dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl,
2.3- dihydrothiazol-2-yl, 2,3-dihydrothiazol-3-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl,
3.4- dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl, 3,4-dihydrothiazol-4-yl, 3,4-dihydrothiazol-5-yl, 3,4-dihydrothiazol-2-yl, 3,4-dihydrothiazol-3-yl, or 3,4-dihydrothiazol-4-yl;
6- membered saturated heterocycles like 1 -piperidinyl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 1 ,4-dioxanyl, 1 , 3-d ith ia n-5-y 1 , 1 ,3-dithianyl, 1 ,3-oxathian-5-yl, 1 ,4-oxathianyl, 2-tetrahydropyranyl, 3-tetrahydopyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiopyranyl, 3-tetra- hydrothiopyranyl,4-tetrahydrothiopyranyl, 1 -hexahydropyridazinyl, 3-hexahydropyridazinyl, 4- hexahydropyridazinyl, 1 -hexahydropyrimidinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 1-piperazinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-1-yl, 1 ,3,5-hexahy- drotriazin-2-yl, 1 ,2,4-hexahydrotriazin-1 -yl, 1 ,2,4-hexahydrotriazin-3-yl, tetrahydro-1 ,3-oxazin-1- yl, tetrahydro-1 ,3-oxazin-2-yl, tetrahydro-1 ,3-oxazin-6-yl, 1 -morpholinyl, or 2-morpholinyl, 3-mor- pholinyl;
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. thiazol-2-yl, thiazol-4-yl, thiazol-5-yl), oxadia- zolyl (e.g. 1 ,2,3-oxadiazol-4-yl, 1 ,2,3-oxadiazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl, 1 ,3,4-oxadiazol-2-yl), thiadiazolyl (e.g. 1 ,2,3-thiadiazol-4-yl, 1 ,2,3-thiadiazol-5-yl, 1 ,2,4-thiadia- zol-3-yl, 1 ,2,4-thiadiazol-5-yl, 1 ,3,4-thiadiazolyl-2-yl), triazolyl (e.g. 1 ,2,3-triazol-4-yl, 1 ,2,4-tria- zol-3-yl); 1 -tetrazolyl; 6-membered aromatic rings like pyridyl (e.g. pyridine-2-yl, pyridine-3-yl, pyridine-4-yl), pyrazinyl (e.g. pyridazin-3-yl, pyridazin-4-yl), pyrimidinyl (e.g. pyrimidin-2-yl, py- rimidin-4-yl, pyrimidin-5-yl), pyrazin-2-yl, triazinyl (e.g. 1 ,3,5-triazin-2-yl, or 1 ,2,4— triazin-3-yl, 1 ,2,4-triazin-5-yl, 1 ,2,4-triazin-6-yl);
The term "substituted" if not specified otherwise refers to substituted by 1 , 2 or maximum pos- sible 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.
The substituent R4 if present, can be present in any ring of "Z".
The term "acidic functionality" if not specified otherwise refers to a functionality capable of do- nating a hydrogen (proton or hydrogen ion H+), such as a carboxylic group or a sulphonic group, or, alternatively, capable of forming a covalent bond with an electron pair.
The terms "compounds of formula (I)", "Pyridine compounds of formula (I)", "Compounds I" and "compounds of invention" are synonyms.
The preferred embodiments of the invention mentioned herein below have to be understood as being preferred either independently from each other or in combination with one another.
In general, pyridine compounds of formula (I) are suitable as herbicides.
According to a preferred embodiment of the invention preference is given 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:
Preferred R1 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;
particularly preferred R1 is Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted;
especially preferred R1 is C3-C6-cycloalkyl, wherein the cycloalkyl substituent is unsubstituted; also especially preferred R1 is C2H5, 1-C3H7, 1-C4H9, OCH3, C-C3H5, or C-C4H9;
more preferred R1 is C2H5, OCH3, or C-C3H5;
most preferred R1 is C-C3H5.
Preferred R2 is C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-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, hydroxycycloalkenyl-Ci-C6-alkyl, Ci-C6-hydroxyalkyl, C3-C6-cycloalkyl-C2-C6-hydrox- yalkylidenyl, hydroxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycar- bonyl-Ci-C6-alkyl, C3-C6-hydroxycycloalkyl-Ci-C6-hydroxyalkyl, C2-C6-dihydroxyalkyl, C3-C6-cy- cloalkyl-C3-C6-dihydroxyalkylidenyl, hydroxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-alkoxycar- bonyl-C2-C6-dihydroxyalkyl, Ci-C6-dicyanoalkyl, or 5- or 6-membered heteroaryl;
wherein hydroxy groups of R2 are unsubstituted or substituted by Rb,
cyclic groups of R2 are unsubstituted or substituted by Rc, and
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd. particularly preferred R2 is C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkenyl, C3-C6-cycloalkyl- Ci-C6-alkylidenyl, C3-C6- alocycloalkyl-Ci-C6-alkylidenyl, C3-C6- ydroxycycloalkyl-Ci-C6-alkyl, C3-C6- ydroxycycloalkyl-Ci-C6- ydroxyalkyl, C2-C6-dihydroxyalkyl, or 5- or 6-membered het- eroaryl;
also particularly preferred R2 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;
wherein hydroxy groups of R2 are unsubstituted or substituted by Rb,
cyclic groups of R2 are unsubstituted or substituted by Rc, and
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd.
especially preferred R2 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;
also especially preferred R2 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;
also especially preferred R2 is C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, Ci-C6-hydrox- yalkyl, C2-C6-dihydroxyalkyl, or 5- or 6-membered heteroaryl;
wherein hydroxy groups of R2 are unsubstituted or substituted by Rb,
cyclic groups of R2 are unsubstituted or substituted by Rc, and
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd.
more preferred R2 is C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, or 5- or 6-membered heteroaryl;
also more preferred R2 is Ci-C6-hydroxyalkyl, C2-C6-dihydroxyalkyl, C3-C6-cycloalkyl-Ci-C6-al- kylidenyl, or 5- or 6-membered heteroaryl;
wherein hydroxy groups of R2 are unsubstituted or substituted by Rb,
cyclic groups of R2 are unsubstituted or substituted by Rc, and
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd.
most preferred R2 is C2-C6-alkenyl;
also most preferred R2 is C3-C6-cycloalkyl-Ci-C6-alkylidenyl;
also most preferred R2 is 5- or 6-membered heteroaryl;
also most preferred R2 is Ci-C6-hydroxyalkyl
also most preferred R2 is C2-C6-dihydroxyalkyl;
wherein hydroxy groups of R2 are unsubstituted or substituted by Rb,
cyclic groups of R2 are unsubstituted or substituted by Rc, and
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd.
also more preferred R2 is CH=CH-CH3, CH=C(CH2)3, or CH=C(CH2)4;
also more preferred R2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, 3-methyl-2-furyl, or 4-methyloxazol- 5-yl;
also most preferred R2 is CH=CH-CH3, CH=C(CH2)3, 2-furyl, 3-furyl, or 4-methyloxazol-5-yl; also most preferred R2 is CHOH-CHOH-C6H5, CHOH-CHOH-2-furyl, CHOH-CHOH-CH3, or 4- methyloxazol-5-yl.
also most preferred R2 is selected from R2-1 to R2-16 as shown below,
Figure imgf000026_0001
wherein # denotes attachment to the pyridine ring, X and Y denotes Rc which independently of each other are identical or different;
preferred R2 is R2-1 , R2-2, R2-3, R2-4, R2-5, R2-6, R2-7, or R2-8;
also preferred R2 is R2-9, R2-10, R2-1 1 , R2-13, R2-14, or R2-15;
more preferred R2 is R2-9, R2-10, or R2-15;
most preferred R2 is R2-9;
preferred X1 is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, Ci-C6-haloal- koxy, or Ci-C6-alkylthio;
particularrly preferred X1 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 X1 is H, halogen, CN, Ci-C4-alkyl, OH, Ci-C4-alkoxy, or Ci-C4-alkylthio; more preferred X1 is H, CH3, C2H5, n-propyl, iso-propyl, iso-butyl, n-butyl, OH, OCH3, SCH3, F, CI, Br, or I;
most preferred X1 is H, CH3, C2H5, OH, or OCH3;
also most preferred X1 is H, CH3, C2H5, or SCH3;
also most preferred X1 is H, CH3, C2H5, F, CI, Br, or I.
preferred Y1 is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, Ci-C6-haloal- koxy, or Ci-C6-alkylthio;
particularrly preferred Y1 is H, halogen, CN, Ci-C6-alkyl, OH, Ci-C6-alkoxy, or Ci-C6-alkylthio; also particularrly preferred Y1 is H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy;
especially preferred Y1 is H, halogen, CN, Ci-C4-alkyl, Ci-C2-fluoroalkyl, OH, Ci-C4-alkoxy, or CrC4-alkylthio;
more preferred Y1 is H, CH3, C2H5, n- propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, t-butyl, OH, OCH3, SCH3, F, CI, Br, or I;
most preferred Y1 is H, CH3, C2H5, n- propyl, iso-propyl, iso-butyl, n-butyl, 2-butyl, OH, or OCH3;
also most preferred Y1 is H, CH3, C2H5, n-propyl, iso-propyl, OH, OCH3, or SCH3; also most preferred Y1 is H, CH3, C2H5, n-propyl, iso-propyl, F, CI, Br, or I .
Particularly preferred R2 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.
Examples of more particularly preferred R2 are provided in Table R2-9, Table R2-10, and Table R2-15.
Table R2-9: examples of particularly preferred R2 are R2-9.1 to R2-9.676 wherein R2 is R2-9 and combinations of variables X1 and Y1 are as defined in each row of table R2, numbering of each compound e.g. R2-9.1 means R2 is R2-9 wherein X1 and Y1 are as defined in row 1 of table R2;
Table R2-10: examples of particularly preferred R2 are R2-10.1 to R2-10.676 wherein R2 is R2- 10 and combinations of variables X1 and Y1 are as defined in each row of table R2, numbering of each compound e.g. R2-10.1 means R2 is R2-10 wherein X1 and Y1 are as defined in row 1 of table R2;
Table R2-15: examples of particularly preferred R2 are R2-15.1 to R2-15.676 wherein R2 is R2- 15 and combinations of variables X1 and Y1 are as defined in each row of table R2, numbering of each compound e.g. R2-15.1 means R2 is R2-15 wherein X1 and Y1 are as defined in row 1 of table R2.
Table R2:
Figure imgf000027_0001
Figure imgf000028_0001
row X1 Y1 row X1 Y1 row X1 Y1
172 n-butyl F 208 2-butyl OCF3 244 OH OH
173 n-butyl CI 209 C(CH3)3 H 245 OH OCH3
174 n-butyl Br 210 C(CH3)3 CH3 246 OH SCH3
175 n-butyl I 21 1 C(CH3)3 C2H5 247 OH S(0)CH3
176 n-butyl CH2CF3 212 C(CH3)3 n-propyl 248 OH S(0)2CH3
177 n-butyl CF2CF3 213 C(CH3)3 CH(CH3)2 249 OH CN
178 n-butyl CF2CH3 214 C(CH3)3 iso-butyl 250 OH F
179 n-butyl CFs 215 C(CH3)3 n-butyl 251 OH CI
180 n-butyl CF2H 216 C(CH3)3 2-butyl 252 OH Br
181 n-butyl OCF2H 217 C(CH3)3 C(CH3)3 253 OH I
182 n-butyl OCF3 218 C(CH3)3 OH 254 OH CH2CF3
183 2-butyl H 219 C(CH3)3 OCH3 255 OH CF2CF3
184 2-butyl CHs 220 C(CH3)3 SCH3 256 OH CF2CH3
185 2-butyl C2H5 221 C(CH3)3 S(0)CH3 257 OH CF3
186 2-butyl n-propyl 222 C(CH3)3 S(0)2CH3 258 OH CF2H
187 2-butyl CH(CHs)2 223 C(CH3)3 CN 259 OH OCF2H
188 2-butyl iso-butyl 224 C(CH3)3 F 260 OH OCF3
189 2-butyl n-butyl 225 C(CH3)3 CI 261 OCH3 H
190 2-butyl 2-butyl 226 C(CH3)3 Br 262 OCH3 CH3
191 2-butyl C(CHs)s 227 C(CH3)3 I 263 OCH3 C2H5
192 2-butyl OH 228 C(CH3)3 CH2CF3 264 OCH3 n-propyl
193 2-butyl OCHs 229 C(CH3)3 CF2CF3 265 OCH3 CH(CH3)2
194 2-butyl SCHs 230 C(CH3)3 CF2CH3 266 OCH3 iso-butyl
195 2-butyl S(0)CH3 231 C(CH3)3 CF3 267 OCH3 n-butyl
196 2-butyl S(0)2CH3 232 C(CH3)3 CF2H 268 OCH3 2-butyl
197 2-butyl CN 233 C(CH3)3 OCF2H 269 OCH3 C(CH3)3
198 2-butyl F 234 C(CH3)3 OCF3 270 OCH3 OH
199 2-butyl CI 235 OH H 271 OCH3 OCH3
200 2-butyl Br 236 OH CH3 272 OCH3 SCH3
201 2-butyl I 237 OH C2H5 273 OCH3 S(0)CH3
202 2-butyl CH2CF3 238 OH n-propyl 274 OCH3 S(0)2CH3
203 2-butyl CF2CF3 239 OH CH(CH3)2 275 OCH3 CN
204 2-butyl CF2CH3 240 OH iso-butyl 276 OCH3 F
205 2-butyl CF3 241 OH n-butyl 277 OCH3 CI
206 2-butyl CF2H 242 OH 2-butyl 278 OCH3 Br
207 2-butyl OCF2H 243 OH C(CH3)3 279 OCH3 I row X1 Y1 row X1 Y1 row X1 Y1
280 OCHs CH2CFs 316 S(0)CHs n-propyl 352 S(0)2CHs S(0)2CHs
281 OCHs CF2CF3 317 S(0)CHs CH(CHs)2 353 S(0)2CHs CN
282 OCHs CF2CH3 318 S(0)CHs iso-butyl 354 S(0)2CHs F
283 OCHs CFs 319 S(0)CHs n-butyl 355 S(0)2CHs CI
284 OCHs CF2H 320 S(0)CHs 2-butyl 356 S(0)2CHs Br
285 OCHs OCF2H 321 S(0)CHs C(CHs)s 357 S(0)2CHs I
286 OCHs OCFs 322 S(0)CHs OH 358 S(0)2CHs CH2CF3
287 SCHs H 323 S(0)CHs OCHs 359 S(0)2CHs CF2CF3
288 SCHs CHs 324 S(0)CHs SCHs 360 S(0)2CHs CF2CH3
289 SCHs C2H5 325 S(0)CHs S(0)CHs 361 S(0)2CHs CFs
290 SCHs n-propyl 326 S(0)CHs S(0)2CHs 362 S(0)2CHs CF2H
291 SCHs CH(CHs)2 327 S(0)CHs CN 363 S(0)2CHs OCF2H
292 SCHs iso-butyl 328 S(0)CHs F 364 S(0)2CHs OCFs
293 SCHs n-butyl 329 S(0)CHs CI 365 CN H
294 SCHs 2-butyl 330 S(0)CHs Br 366 CN CHs
295 SCHs C(CHs)s 331 S(0)CHs I 367 CN C2H5
296 SCHs OH 332 S(0)CHs CH2CF3 368 CN n-propyl
297 SCHs OCHs 333 S(0)CHs CF2CF3 369 CN CH(CHs)2
298 SCHs SCHs 334 S(0)CHs CF2CH3 370 CN iso-butyl
299 SCHs S(0)CHs 335 S(0)CHs CFs 371 CN n-butyl
300 SCHs S(0)2CHs 336 S(0)CHs CF2H 372 CN 2-butyl
301 SCHs CN 337 S(0)CHs OCF2H 373 CN C(CHs)s
302 SCHs F 338 S(0)CHs OCFs 374 CN OH
303 SCHs CI 339 S(0)2CHs H 375 CN OCHs
304 SCHs Br 340 S(0)2CHs CHs 376 CN SCHs
305 SCHs I 341 S(0)2CHs C2H5 377 CN S(0)CHs
306 SCHs CH2CF3 342 S(0)2CHs n-propyl 378 CN S(0)2CHs
307 SCHs CF2CF3 343 S(0)2CHs CH(CHs)2 379 CN CN
308 SCHs CF2CH3 344 S(0)2CHs iso-butyl 380 CN F
309 SCHs CF3 345 S(0)2CHs n-butyl 381 CN CI
310 SCHs CF2H 346 S(0)2CHs 2-butyl 382 CN Br
31 1 SCHs OCF2H 347 S(0)2CHs C(CHs)s 383 CN I
312 SCHs OCFs 348 S(0)2CHs OH 384 CN CH2CF3
313 S(0)CHs H 349 S(0)2CHs OCHs 385 CN CF2CF3
314 S(0)CHs CHs 350 S(0)2CHs SCHs 386 CN CF2CH3
315 S(0)CHs C2H5 351 S(0)2CHs S(0)CHs 387 CN CFs
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0001
Preferred A is CR3, C*. NR3A, N, S or O;
particularly preferred A is CR3, C*, NR3A, or N;
also particularly preferred A is S or O;
especially preferred A is C*, CR3 or N;
most preferred A is CR3;
also most preferred A is C*;
also most preferred A is N.
Preferred Z is 9 or l Omembered bicyclic ring;
particularly preferred Z is 9 membered bicyclic ring; particularly preferred Z is 10 membered bicyclic ring; more preferred Z is selected from below groups A to O,
Figure imgf000034_0001
wherein
Y is 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 heteroatoms selected from O, N, and S;
R3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
m is 0, 1 or 2;
R4 is halogen, CN, CrC6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
X is O, S, or NR3A;
R3A is H, d-Ce-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyridine ring.
Preferred Y is phenyl;
Also preferred Y is 5- or 6-membered partially or fully unsaturated carbocycle comprising 1 , 2, or 3 heteroatoms selected from O, N, and S;
particularly preferred Y is phenyl;
also particularly preferred Y is 5-membered partially or fully unsaturated carbocycle comprising 1 , or 2 heteroatoms selected from O, N, and S;
more preferred Y is 5-membered partially unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms selected from O, N, and S, e.g. 1 ,3-dithiolane, 1 ,3-oxathiolane, 1 ,3-dioxolane, 2,3- dihydrofuran, 2,3-dihydrothiophene, or 2,3-dihydro-1 H-pyrrole; more preferably heteroatoms are selected from O and S, e.g. 1 ,3-oxathiolane, 1 ,3-dioxolane, 2,3-dihydrofuran, or 2,3-dihydrothio- phene; most preferred heteroatom in Y is O, e.g. 1 ,3-dioxolane, or 2,3-dihydrofuran; also most preferred heteroatom in Y is S, e.g. 2,3-dihydrothiophene; also more preferred Y is 5-membered fully unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms selected from O, N, and S (furan, thiophene, 1 H-pyrrole, 1 ,2-oxazole, 1 ,3-oxazole, 1 ,2-thiazole, 1 ,3-thiazole, imidazole, 1 H-pyrazole); more preferably heteroatoms are selected from O and S; most preferred heteroatom is O; also most preferred heteroatom is S;
most preferred Y is 5-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms;
also particularly preferred Y is 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms selected from O, N, and S;
more preferred Y is 6-membered partially unsaturated carbocycle comprising 0, 1 , or 2 het- eroatoms selected from O, N, and S; more preferably heteroatoms are selected from O and S; also more preferably heteroatoms are selected from O and N; most preferred heteroatom is O; also more preferred Y is 6-membered fully unsaturated carbocycle comprising 0, 1 , or 2 heteroatoms N;
Preferred R3 is halogen, CN, NO2, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or C3-C6-cycloal- kyl;
also preferred R3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy,
particularly preferred R3 is halogen, CN, Ci-C6-alkyl, or Ci-C6-alkoxy;
especially preferred halogen, or CH3;
also especially preferred R3 is halogen;
more preferred R3 is CI, Br, or I;
most preferred R3 is CI or Br.
Preferred R3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C3-C6-alkenyl, C3-C6- haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl;
also preferred R3A is H, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkylcarbonyl;
particularly preferred R3A is H, Ci-C6-alkyl, or Ci-C6-alkylcarbonyl;
especially preferred R3A is H, or Ci-C6-alkyl;
most preferred R3A is H, or CH3.
Preferred R4 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
particularly preferred R4 is halogen, Ci-C6-haloalkyl, or Ci-C6-alkyl;
especially preferred R4 is halogen;
also especially preferred R4 is Ci-C6-haloalkyl, or Ci-C6-alkyl;
more preferred R4 is F, CI, CHF2, CF3, CH3, or C2H5;
most preferred R4 is F;
also most preferred R4 is CH3;
also most preferred R4 is CI.
also most preferred R4 is CF3.
Preferred m is 0, 1 , or 2;
more preferred m is 0 or 1 ;
most preferred m is 0.
also most preferred m is 1.
Preferred Z is A, B, C, D, E, F, G, H, I, J, or K;
more preferred Z is A, E, or F;
most preferred Z is A;
Also preferred Z is L, M, N, or O Also preferred are the pyridine compounds of formula (I), and their use as herbicide, wherein R1 is preferably Ci-C6-alkyl, Ci-C6-alkoxy, or C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted;
particularly preferred R1 is C3-C6-cycloalkyl, wherein the cycloalkyi substituent is unsubstituted; R2 is preferably C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, 5- or 6-membered het- eroaryl, Ci-C6-hydroxyalkyl, or C2-C6-dihydroxyalkyl;
particularly preferred R2 is C2-C6-alkenyl, 5- or 6-membered heteroaryl, or Ci-C6-hydroxyalkyl; also particularly preferred R2 is C3-C6-cycloalkyl-CrC6-alkylidenyl, C2-C6-dihydroxyalkyl or 5- or 6-membered heteroaryl;
more preferred R2 is CH=CH-CH3, CH=C(CH2)3, or CH=C(CH2)4;
also more preferred R2 is 2-furyl, 3-furyl, 2-methyl-3-furyl, 3-methyl-2-furyl, 4-methyloxazol-5- yl, CHOH-CHOH-C6H5, or CHOH-CHOH-2-furyl;
most preferred R2 is CH=CH-CH3, CH=C(CH2)3, 2-furyl, 3-furyl, 4-methyloxazol-5-yl, CHOH- CHOH-C6H5, or CHOH-CHOH-2-furyl.
wherein acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd.
A is preferably CR3, C*, N, O, S or NR3A;
particularly preferred A is CR3, C*, or N;
also particularly preferred A is CR3, C*, O or S;
Preferred Z is 9 or 10 membered bicyclic ring;
particularly preferred Z is 9 membered bicyclic ring;
particularly preferred Z is 10 membered bicyclic ring;
more preferred Z is selected from group A to O, as defined herein;
R3 is preferably halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
particularly preferred R3 is halogen or CH3;
R3A is preferably H or Ci-C6-alkyl;
particularly preferred R3A is H or CH3;
m is preferably 0 or 1 ;
R4 is preferably halogen.
Also preferred are the pyridine compounds of formula (I), wherein
Figure imgf000036_0001
R2 is Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloal- kenyl-Ci-C6-alkyl, C3-C6-cycloalkyl-CrC6-alkylidenyl, Ci-C6-hydroxyalkyl, hydroxycarbonyl-Cr C6-alkyl, hydroxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkoxycar- bonyl-Ci-C6-haloalkyl, or 5- membered heteroaryl;
wherein OH groups of R2 are unsubstituted or substituted by Rb,
cyclic groups of R2 are unsubstituted or substituted by Rc, and
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd;
Rb is d-Ce-alkyl;
Rc is d-Ce-alkyl or OH;
Rd is phenyl or 5- or 6- membered heteroaryl;
wherein the substituent Rd is unsubstituted or substituted by Re;
Re is halogen, CN, N02, Ci-Ce-alkyl, Ci-C6-haloalkyl, OH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, Ci-C6-alkylsulfonyl;
Z is A, E or F; Y is 5- or 6-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms; R3 is R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy; prefer- rably Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-haloalkoxy; more preferrably CI, Br, F, I, CH3, or OCF3; most preferably CI;
m is 0 or 1 ;
R4 is halogen, preferably Br.
Also preferred are the pyridine compounds of formula (I), wherein
R1 is c-C3H5;
R2 is Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6-alkenyl, C3-C6-cycloalkyl-Ci-C6-alkyl, d-Ce-cycloal- kenyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6-alkylidenyl, Ci-C6-hydroxyalkyl, Ci-d-alkoxycarbonyl- Ci-C6-alkyl, or 5- membered heteroaryl;
wherein OH groups of R2 are unsubstituted or substituted by Rb,
cyclic groups of R2 are unsubstituted or substituted by Rc, and
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd;
Rb is Ci-Ce-alkyl;
Rc is Ci-Ce-alkyl or OH;
Rd is 5- or 6- membered heteroaryl or 3- to 6-membered heterocyclyl;
wherein the substituent Rd is unsubstituted or substituted by Re;
Re is halogen, CN, N02, Ci-Ce-alkyl, Ci-Ce-haloalkyl, OH, Ci-C6-alkoxy, Ci-C6-haloalkoxy, d-Ce-alkylsulfonyl;
Z is A;
Y is 5- or 6-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms; R3 is R3 is halogen, Ci-d-alkyl, Ci-d-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy; preferably Ci-d-alkyl, Ci-C6-haloalkyl, or d-d-haloalkoxy; more preferably CI, Br, F, I, CH3, or OCF3; most preferably CI;
m is 0 or 1 ; preferably 0;
R4 is F, Br, CI, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (I), wherein
Figure imgf000037_0001
R2 is R2-9, R2-10 or R2-15, preferably R2-9;
Z is A;
Y is 5- or 6-membered partially unsaturated carbocycle comprising 1 or 2 oxygen atoms; R3 is R3 is halogen, Ci-d-alkyl, Ci-d-haloalkyl, Ci-C6-alkoxy, or Ci-C6-haloalkoxy; preferably Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-d-haloalkoxy; more preferably CI, Br, F, I, CH3, or OCF3; most preferably CI;
m is 0 or 1 ; preferably 0;
R4 is F, Br, CI, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (1.1 ) (corresponds to pyridine compounds of formula (I) wherein R2 is CH=CH-CH3), and their use as herbicide,
Figure imgf000038_0001
wherein the dotted line ( ) is a single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR3A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
R3A is H or Ci-Ce-alkyl;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CF3, CH3, or C2H5.
Also preferred are the pyridine compounds of formula (1.2) (corresponds to pyridine compounds of form and their use as herbicide,
Figure imgf000038_0002
wherein the dotted line ( ) is a single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR3A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (1.3) (corresponds to pyridine compounds of form H2)4), and their use as herbicide,
Figure imgf000038_0003
wherein the dotted line ( ) is a single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR3A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (1.4) (corresponds to pyridine compounds of formula (I) wherein R2 is 2-furyl), and their use as herbicide,
Figure imgf000039_0001
wherein the dotted line ( ) is a single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR3A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (1.5) (corresponds to pyridine com- pounds of formula (I) wherein R2 is 3-furyl), and their use as herbicide,
Figure imgf000039_0002
wherein the dotted line ( ) is a single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR3A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (1.6) (corresponds to pyridine com- pounds of formula (I) wherein R2 is 3-methyl-2-furyl), and their use as herbicide,
Figure imgf000039_0003
wherein the dotted line ( ) is a single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR3A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (1.7) (corresponds to pyridine com- pounds of formula (I) wherein R2 is 2-methyl-3-furyl), and their use as herbicide,
Figure imgf000040_0001
wherein the dotted line ( ) is a single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR3A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (1.8) (corresponds to pyridine com- pounds of formul HOH-C6H5), and their use as herbicide,
Figure imgf000040_0002
wherein the dotted line ( ) is a single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (1.9) (corresponds to pyridine pounds of formul HOH-2-furyl), and their use as herbicide,
Figure imgf000040_0003
wherein the dotted line ( ) is a single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CH3, CF3, or C2H5. Also preferred are the pyridine compounds of formula (1.10) (corresponds to pyridine compounds of formula (I) wherein R2 is 4-methyloxazol-5-yl, R4 is H), and their use as herbicide,
Figure imgf000041_0001
wherein the dotted line (■ single bond or a double bond;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy;
A is CR3, C*, NR3A, N, O or S;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, CHF2, CH3, CF3, or C2H5.
Also preferred are the pyridine compounds of formula (1.1 1 ) (corresponds to pyridin
pounds of formula (I) wherein R2 is R2-9), and their use as herbicide,
Figure imgf000041_0002
wherein the dotted line ( ) is a single bond or a double bond;
X1 and Y1 independently are selected from H, CH3, C2H5, n-propyl, iso-propyl, iso-butyl, n-bu- tyl, 2-butyl, t-butyl, OH, OCH3, SCH3, S(0)CH3, S(0)2CH3, CN, F, CI, Br, I, CH2CF3, CF2CF3, CF2CH3, CF3, CF2H, OCF2H, and OCF3;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy; preferably c-C3H5;
A is CR3;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
Z is radical selected from A to O;
m is 0 or 1 ;
R4 is F, Br, CI, CHF2, CH3, CF3, or C2H5; preferably F, CI, CHF2, CH3, CF3, or C2H5; more preferably CI.
Also preferred are the pyridine compounds of formula (1.1 1. A) (corresponds to pyridine compounds of formula (I), wherein R2 is R2-9) and their use as herbicide,
Figure imgf000041_0003
wherein X1 and Y1 independently are selected from H, CH3, C2H5, n-propyl, iso-propyl, iso-butyl, n-bu- tyl, 2-butyl, t-butyl, OH, OCH3, SCH3, S(0)CH3, S(0)2CH3, CN, F, CI, Br, I, CH2CF3, CF2CF3, CF2CH3, CF3, CF2H, OCF2H, and OCF3;
X, V and W independently are CH2, CF2, O, NR3A, N or S; wherein R3A is H or CH3;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy; preferably C-C3H5;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
m is 0 or 1 ;
R4 is F, Br, CI, CHF2, CH3, CF3, or C2H5; preferably F, CI, CHF2, CH3, CF3, or C2H5; more preferably CI.
Also preferred are the pyridine compounds of formula (1.1 1.C) (corresponds to pyridine compounds of formula (I), wherein wherein R2 is R2-9) and their use as herbicide,
Figure imgf000042_0001
wherein
X1 and Y1 independently are selected from H, CH3, C2H5, n-propyl, iso-propyl, iso-butyl, n-bu- tyl, 2-butyl, t-butyl, OH, OCH3, SCH3, S(0)CH3, S(0)2CH3, CN, F, CI, Br, I, CH2CF3, CF2CF3, CF2CH3, CF3, CF2H, OCF2H, and OCF3;
X, V and W independently are CH2, CF2, O, NR3A, N or S; wherein R3A is H or CH3;
R1 is C3-C6-cycloalkyl, Ci-C6-alkyl, or Ci-C6-alkoxy; preferably c-C3Hs;
R3 is halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
m is 0 or 1 ;
R4 is F, Br, CI, CHF2, CH3, CF3, or C2H5; preferably F, CI, CHF2, CH3, CF3, or C2H5; more preferably CI.
Particular preference is given to the pyridine compounds of formula I which corresponds to compounds of formulae I. a to I.I, and their use as herbicide, wherein X, V and W independently are CH2, CF2, O, NR A, N or S.
Also particular preference is given to the pyridine compounds of formula I which corresponds to compounds of formulae l.m and l.n, and their use as herbicide, wherein X, and V independently are CH2, CF2, O, NR3A, N or S, W independently is CH or N.
Figure imgf000043_0001
Most preferred compounds of formula I, and their use as herbicide, are the compounds of the formulae I. a to I.I wherein
R1 is C2H5, C-C3H5, C-C4H7, or OCH3;
R2 is CH=CH-CH3, CH=C(CH2)3, CH=C(CH2)4, 2-furyl, 3-furyl, 3-methyl-2-furyl, 2-methyl-3- furyl, 4-methyloxazol-5-yl, CHOH-CHOH-C6H5, or CHOH-CHOH-2-furyl;
R3 is CH3, OCH3, CI, Br, CHF2, CF3, F, or I;
Figure imgf000043_0002
V is CH2 or CF2;
W is CH2, O, N, or S;
m is 0 or 1 ;
R4 is F, CI or CF3.
Also most preferred compounds of formula I, and their use as herbicide, are the compounds of the formulae l.m and l.n wherein
R1 is C2H5, C-C3H5, C-C4H7, or OCH3;
R2 is CH=CH-CH3, CH=C(CH2)3, CH=C(CH2)4, 2-furyl, 3-furyl, 3-methyl-2-furyl, 2-methyl-3- furyl, 4-methyloxazol-5-yl, CHOH-CHOH-C6H5, CHOH-CHOH-2-furyl, R2-9.1 to R2-9.676 from Table R2-9, R2-10.1 to R2-10.676 from Table R2-10, or R2-15.1 to R2-15.676 from Table R2-15; R3 is CH3, OCH3, CI, Br, CHF2, CF3, F, or I;
Figure imgf000044_0001
V is CH2 or CF2;
W is CH or N;
m is 0 or 1 ;
R4 is F, CI or CF3.
Each of the groups mentioned for a substituent in the tables is furthermore per se, independently of the combination in which it is mentioned, a particularly preferred aspect of the substituent in question.
Particularly preferred compounds of formula I, and their use as herbicide, compounds of the invention are the compounds of the formulae that are compiled in the following Tables 1 to 52.
Table 1 . Compounds of formula I. a, wherein m is 0, V is CH2, X and W are O, ^compounds of formula 1.1 ), and the meaning for the combination of R1 , R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 2. Compounds of formula l.a, wherein m is 1 , R4 is 2"- CI, V is CH2, X and W are O, (=compounds of formula 1.2), and the meaning for the combination of R1, R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 3. Compounds of formula l.b, wherein m is 0, V is CH2, X and W are O, ^compounds of formula 1.3), and the meaning for the combination of R1 , R2, and R3 for each individ- ual compound corresponds in each case to one line of Table A.
Table 4. Compounds of formula l.b, wherein m is 1 , R4 is 9"- CI, V is CH2, X and W are O, (=compounds of formula 1.4), and the meaning for the combination of R1, R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 5. Compounds of formula l.c, wherein m is 0, V is CH2, X and W are O, (=com- pounds of formula 1.5), and the meaning for the combination of R1 , R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 6. Compounds of formula l.c, wherein m is 1 , R4 is 9"- CI, V is CH2, X and W are O, (=compounds of formula 1.6), and the meaning for the combination of R1, R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 7. Compounds of formula l.d, wherein m is 0, V is CH2, X and W are O, ^compounds of formula 1.7), and the meaning for the combination of R1 , R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 8. Compounds of formula l.d, wherein m is 1 , R4 is 3"- CI, V is CH2, X and W are O, (=compounds of formula 1.8), and the meaning for the combination of R1, R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 9. Compounds of formula l.e, wherein m is 0, V is CH2, X and W are O, ^compounds of formula 1.9), and the meaning for the combination of R1 , R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 10. Compounds of formula l.e, wherein m is 1 , R4 is 3"- CI, V is CH2, X and W are O, (=compounds of formula 1.10), and the meaning for the combination of R1 , R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 1 1. Compounds of formula l.f, wherein m is 0, V is Ch , X and W are O, ^compounds of formula 1.1 1 ), and the meaning for the combination of R1, R2, and R3 for each individ- ual compound corresponds in each case to one line of Table A.
Table 12. Compounds of formula l.f, wherein m is 1 , R4 is 2"- CI, V is Chb, X and W are O, (=compounds of formula 1.12), and the meaning for the combination of R1 , R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 13. Compounds of formula l.g, wherein m is 0, V is CF2, V is CH2, X and W are O, (=compounds of formula 1.13), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 14. Compounds of formula l.g, wherein m is 1 , R4 is 2"- CI, V is CF2, X and W are O, (=compounds of formula 1.14), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 15. Compounds of formula l.g, wherein m is 0, V is CH2, X and W are O ^compounds of formula 1.15), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 16. Compounds of formula l.g, wherein m is 1 , R4 is 2"- CI, V is CH2, X and W are O, (=compounds of formula 1.16), and the meaning for the combination of R1 and R2 for each indi- vidual compound corresponds in each case to one line of Table A.
Table 17. Compounds of formula l.g, wherein m is 0, V is CH2, X is CH2 and W is O, (=compounds of formula 1.17), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 18. Compounds of formula l.g, wherein m is 1 , R4 is 2"- CI, V is CH2, X is CH2 (=com- pounds of formula 1.18 and W is O, and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 19. Compounds of formula l.g, wherein m is 0, V, X, and W are CH2, (=compounds of formula 1.19), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 20. Compounds of formula l.g, wherein m is 1 , R4 is 2"- CI, V, X, and W are CH2,
(=compounds of formula 1 .20), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 21. Compounds of formula l.h, wherein m is 0, V is CF2, X and W are O, ^compounds of formula 1.21 ), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 22. Compounds of formula l.h, wherein m is 1 , R4 is 2"- CI, V is CF2, X and W are O, (=compounds of formula 1.22), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 23. Compounds of formula l.h, wherein m is 0, V is CH2, X and W are O (=com- pounds of formula 1.23), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 24. Compounds of formula l.h, wherein m is 1 , R4 is 2"- CI, V is CH2, X and W are O, (=compounds of formula 1.24), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A. Table 25. Compounds of formula l.h, wherein m is 0, V is CH2, X is CH2 and W is O, (=compounds of formula 1.25), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 26. Compounds of formula l.h, wherein m is 1 , R4 is 2"- CI, V is CH2, X is CH2 (=com- pounds of formula 1 .26), and W is O, and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 27. Compounds of formula l.h, wherein m is 0, V, X, and W are CH2, (=compounds of formula 1.27), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 28. Compounds of formula l.h, wherein m is 1 , R4 is 2"- CI, V, X, and W are CH2,
(=compounds of formula 1 .28), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 29. Compounds of formula l.i, wherein m is 0, X and W are O (=compounds of formula 1.29), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 30. Compounds of formula l.i, wherein m is 1 , R4 is 2"- CI, X and W are O ^compounds of formula 1.30), and the meaning for the combination of R1, R2, and R3 for each individual compound corresponds in each case to one line of Table A.
Table 31. Compounds of formula l.j, wherein m is 0, X and W are O (=compounds of for- mula 1.31 ), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 32. Compounds of formula l.j, wherein m is 1 , R4 is 3"- CI, X and W are O ^compounds of formula 1.32), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 33. Compounds of formula l.k, wherein m is 0, X is O (=compounds of formula 1.33), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 34. Compounds of formula l.k, wherein m is 1 , X is O, R4 is 2"- CI (=compounds of formula 1.34), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 35. Compounds of formula I.I, wherein m is 0, X is O (=compounds of formula 1.35), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 36. Compounds of formula I.I, wherein m is 1 , X is O, R4 is 9"-CI (=compounds of for- mula 1.36), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 37. Compounds of formula I.I, wherein m is 0, X is S (=compounds of formula 1.37), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 38. Compounds of formula I.I, wherein m is 1 , X is S, R4 is 9"-CI (=compounds of formula 1.38), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 39. Compounds of formula I.I, wherein m is 0, X is NCH3 (=compounds of formula 1.39), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 40. Compounds of formula I.I, wherein m is 1 , X is NCH3, R4 is 9"-CI (=compounds of formula 1.40), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 41. Compounds of formula l.m, wherein m is 0, X is O, W is N (=compounds of formula 1.41 ), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 42. Compounds of formula l.m, wherein m is 1 , X is O, W is N, R4 is 8"-CI (=com- pounds of formula 1.42), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 43. Compounds of formula l.m, wherein m is 0, X is S, W is N (=compounds of formula 1.43), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 44. Compounds of formula l.m, wherein m is 1 , X is S, W is N, R4 is 8"-CI ^compounds of formula 1.44), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 45. Compounds of formula l.m, wherein m is 0, X is NCH3, W is N (=compounds of formula 1.45), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 46. Compounds of formula l.m, wherein m is 1 , X is NCH3, W is N, R4 is 8"-CI ^compounds of formula 1.46), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 47. Compounds of formula l.n, wherein m is 0, X is O, W is N (=compounds of for- mula 1.47), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 48. Compounds of formula l.n, wherein m is 1 , X is O, W is N, R4 is 7"-CI ^compounds of formula 1.48), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 49. Compounds of formula l.n, wherein m is 0, X is S, W is N (=compounds of formula 1.49), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 50. Compounds of formula l.n, wherein m is 1 , X is S, W is N, R4 is 7"-CI ^compounds of formula 1.50), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 51. Compounds of formula l.n, wherein m is 0, X is NCH3, W is N (=compounds of formula 1.51 ), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table 52. Compounds of formula l.n, wherein m is 1 , X is NCH3, W is N, R4 is 7"-CI (=com- pounds of formula 1.52), and the meaning for the combination of R1 and R2 for each individual compound corresponds in each case to one line of Table A.
Table A: Line R1 R2 R3 Line R1 R2 R3
1-1 c-CsHs CH=CH-CH3 CH3 -36 C-CsHs 3-methyl-2-furyl CH3
I-2 C-C3H5 CH=CH-CH3 OCH3 -37 C-C3H5 3-methyl-2-furyl OCH3
I-3 C-C3H5 CH=CH-CH3 CI -38 C-C3H5 3-methyl-2-furyl CI
I-4 C-C3H5 CH=CH-CH3 Br -39 C-C3H5 3-methyl-2-furyl Br
I-5 C-C3H5 CH=CH-CH3 CHF2 -40 C-CsHs 3-methyl-2-furyl CHF2
I-6 C-C3H5 CH=CH-CH3 F -41 C-C3H5 3-methyl-2-furyl F
I -7 C-C3H5 CH=CH-CH3 I -42 C-C3H5 3-methyl-2-furyl I
I-8 C-C3H5 CH=C(CH2)3 CH3 -43 C-CsHs 2-methyl-3-furyl CH3
I-9 C-C3H5 CH=C(CH2)3 OCH3 -44 C-C3H5 2-methyl-3-furyl OCH3
1-10 C-C3H5 CH=C(CH2)3 CI -45 C-C3H5 2-methyl-3-furyl CI
1-1 1 C-C3H5 CH=C(CH2)3 Br -46 C-C3H5 2-methyl-3-furyl Br
1-12 C-C3H5 CH=C(CH2)3 CHF2 -47 C-C3H5 2-methyl-3-furyl CHF2
1-13 C-C3H5 CH=C(CH2)3 F -48 C-C3H5 2-methyl-3-furyl F
1-14 C-C3H5 CH=C(CH2)3 I -49 C-C3H5 2-methyl-3-furyl I
1-15 C-C3H5 CH=C(CH2)4 CH3 -50 C-C3H5 CHOH-CHOH-CeHs CH3
1-16 C-C3H5 CH=C(CH2)4 OCH3 -51 C-C3H5 CHOH-CHOH-C6H5 OCH3
1-17 C-C3H5 CH=C(CH2)4 CI -52 C-CsHs CHOH-CHOH-CeHs CI
1-18 C-C3H5 CH=C(CH2)4 Br -53 C-C3H5 CHOH-CHOH-CeHs Br
1-19 C-C3H5 CH=C(CH2)4 CHF2 -54 C-C3H5 CHOH-CHOH-CeHs CHF2
I-20 C-C3H5 CH=C(CH2)4 F -55 C-C3H5 CHOH-CHOH-CeHs F
1-21 C-C3H5 CH=C(CH2)4 I -56 C-CsHs CHOH-CHOH-CeHs I
I-22 C-C3H5 2-furyl CH3 -57 C-C3H5 CHOH-CHOH-2-furyl CH3
I-23 C-C3H5 2-furyl OCH3 -58 C-C3H5 CHOH-CHOH-2-furyl OCH3
I-24 C-C3H5 2-furyl CI -59 C-CsHs CHOH-CHOH-2-furyl CI
I-25 C-C3H5 2-furyl Br -60 C-C3H5 CHOH-CHOH-2-furyl Br
I-26 C-C3H5 2-furyl CHF2 -61 C-C3H5 CHOH-CHOH-2-furyl CHF2
I-27 C-C3H5 2-furyl F -62 C-C3H5 CHOH-CHOH-2-furyl F
I-28 C-C3H5 2-furyl I -63 C-C3H5 CHOH-CHOH-2-furyl I
I-29 C-C3H5 3-furyl CH3 -64 C-C3H5 4-methyl-5-oxazolyl CH3
I-30 C-C3H5 3-furyl OCH3 -65 C-C3H5 4-methyl-5-oxazolyl OCH3
1-31 C-C3H5 3-furyl CI -66 C-CsHs 4-methyl-5-oxazolyl CI
I-32 C-C3H5 3-furyl Br -67 C-C3H5 4-methyl-5-oxazolyl Br
I-33 C-C3H5 3-furyl CHF2 -68 C-C3H5 4-methyl-5-oxazolyl CHF2
I-34 C-C3H5 3-furyl F -69 C-CsHs 4-methyl-5-oxazolyl F
I-35 C-C3H5 3-furyl I -70 C-C3H5 4-methyl-5-oxazolyl I Line R1 R2 R3 Line R1 R2 R3
1-71 C-C4H7 CH=CH-CH3 CH3 1-106 C-C4H7 3-methyl-2-furyl CH3
I-72 C-C4H7 CH=CH-CH3 OCH3 1-107 C-C4H7 3-methyl-2-furyl OCH3
I-73 C-C4H7 CH=CH-CH3 CI 1-108 C-C4H7 3-methyl-2-furyl CI
I-74 C-C4H7 CH=CH-CH3 Br 1-109 C-C4H7 3-methyl-2-furyl Br
I-75 C-C4H7 CH=CH-CH3 CHF2 1-1 10 C-C4H7 3-methyl-2-furyl CHF2
I-76 C-C4H7 CH=CH-CH3 F 1-1 1 1 C-C4H7 3-methyl-2-furyl F
I-77 C-C4H7 CH=CH-CH3 I 1-1 12 C-C4H7 3-methyl-2-furyl I
I-78 C-C4H7 CH=C(CH2)3 CH3 1-1 13 C-C4H7 2-methyl-3-furyl CH3
I-79 C-C4H7 CH=C(CH2)3 OCH3 1-1 14 C-C4H7 2-methyl-3-furyl OCH3
I-80 C-C4H7 CH=C(CH2)3 CI 1-1 15 C-C4H7 2-methyl-3-furyl CI
1-81 C-C4H7 CH=C(CH2)3 Br 1-1 16 C-C4H7 2-methyl-3-furyl Br
I-82 C-C4H7 CH=C(CH2)3 CHF2 1-1 17 C-C4H7 2-methyl-3-furyl CHF2
I-83 C-C4H7 CH=C(CH2)3 F 1-1 18 C-C4H7 2-methyl-3-furyl F
I-84 C-C4H7 CH=C(CH2)3 I 1-1 19 C-C4H7 2-methyl-3-furyl I
I-85 C-C4H7 CH=C(CH2)4 CH3 1-120 C-C4H7 CHOH-CHOH-CeHs CH3
I-86 C-C4H7 CH=C(CH2)4 OCH3 1-121 C-C4H7 CHOH-CHOH-C6H5 OCH3
I-87 C-C4H7 CH=C(CH2)4 CI 1-122 C-C4H7 CHOH-CHOH-CeHs CI
I-88 C-C4H7 CH=C(CH2)4 Br 1-123 C-C4H7 CHOH-CHOH-CeHs Br
I-89 C-C4H7 CH=C(CH2)4 CHF2 1-124 C-C4H7 CHOH-CHOH-CeHs CHF2
I-90 C-C4H7 CH=C(CH2)4 F 1-125 C-C4H7 CHOH-CHOH-CeHs F
1-91 C-C4H7 CH=C(CH2)4 I 1-126 C-C4H7 CHOH-CHOH-CeHs I
I-92 C-C4H7 2-furyl CH3 1-127 C-C4H7 CHOH-CHOH-2-furyl CH3
I-93 C-C4H7 2-furyl OCH3 1-128 C-C4H7 CHOH-CHOH-2-furyl OCH3
I-94 C-C4H7 2-furyl CI 1-129 C-C4H7 CHOH-CHOH-2-furyl CI
I-95 C-C4H7 2-furyl Br 1-130 C-C4H7 CHOH-CHOH-2-furyl Br
I-96 C-C4H7 2-furyl CHF2 1-131 C-C4H7 CHOH-CHOH-2-furyl CHF2
I-97 C-C4H7 2-furyl F 1-132 C-C4H7 CHOH-CHOH-2-furyl F
I-98 C-C4H7 2-furyl I 1-133 C-C4H7 CHOH-CHOH-2-furyl I
I-99 C-C4H7 3-furyl CH3 1-134 C-C4H7 4-methyl-5-oxazolyl CH3
1-100 C-C4H7 3-furyl OCH3 1-135 C-C4H7 4-methyl-5-oxazolyl OCH3
1-101 C-C4H7 3-furyl CI 1-136 C-C4H7 4-methyl-5-oxazolyl CI
1-102 C-C4H7 3-furyl Br 1-137 C-C4H7 4-methyl-5-oxazolyl Br
1-103 C-C4H7 3-furyl CHF2 1-138 C-C4H7 4-methyl-5-oxazolyl CHF2
1-104 C-C4H7 3-furyl F 1-139 C-C4H7 4-methyl-5-oxazolyl F
1-105 C-C4H7 3-furyl I 1-140 C-C4H7 4-methyl-5-oxazolyl I Line R1 R2 R3 Line R1 R2 R3
1-141 C2H5 CH=CH-CH3 CH3 1-176 C2H5 3-methyl-2-furyl CH3
1-142 C2H5 CH=CH-CH3 OCH3 1-177 C2H5 3-methyl-2-furyl OCH3
1-143 C2H5 CH=CH-CH3 CI 1-178 C2H5 3-methyl-2-furyl CI
1-144 C2H5 CH=CH-CH3 Br 1-179 C2H5 3-methyl-2-furyl Br
1-145 C2H5 CH=CH-CH3 CHF2 1-180 C2H5 3-methyl-2-furyl CHF2
1-146 C2H5 CH=CH-CH3 F 1-181 C2H5 3-methyl-2-furyl F
1-147 C2H5 CH=CH-CH3 I 1-182 C2H5 3-methyl-2-furyl I
1-148 C2H5 CH=C(CH2)3 CH3 1-183 C2H5 2-methyl-3-furyl CH3
1-149 C2H5 CH=C(CH2)3 OCH3 1-184 C2H5 2-methyl-3-furyl OCH3
1-150 C2H5 CH=C(CH2)3 CI 1-185 C2H5 2-methyl-3-furyl CI
1-151 C2H5 CH=C(CH2)3 Br 1-186 C2H5 2-methyl-3-furyl Br
1-152 C2H5 CH=C(CH2)3 CHF2 1-187 C2H5 2-methyl-3-furyl CHF2
1-153 C2H5 CH=C(CH2)3 F 1-188 C2H5 2-methyl-3-furyl F
1-154 C2H5 CH=C(CH2)3 I 1-189 C2H5 2-methyl-3-furyl I
1-155 C2H5 CH=C(CH2)4 CH3 1-190 C2H5 CHOH-CHOH-CeHs CH3
1-156 C2H5 CH=C(CH2)4 OCH3 1-191 C2H5 CHOH-CHOH-C6H5 OCH3
1-157 C2H5 CH=C(CH2)4 CI 1-192 C2H5 CHOH-CHOH-CeHs CI
1-158 C2H5 CH=C(CH2)4 Br 1-193 C2H5 CHOH-CHOH-CeHs Br
1-159 C2H5 CH=C(CH2)4 CHF2 1-194 C2H5 CHOH-CHOH-CeHs CHF2
1-160 C2H5 CH=C(CH2)4 F 1-195 C2H5 CHOH-CHOH-CeHs F
1-161 C2H5 CH=C(CH2)4 I 1-196 C2H5 CHOH-CHOH-CeHs I
1-162 C2H5 2-furyl CH3 1-197 C2H5 CHOH-CHOH-2-furyl CH3
1-163 C2H5 2-furyl OCH3 1-198 C2H5 CHOH-CHOH-2-furyl OCH3
1-164 C2H5 2-furyl CI 1-199 C2H5 CHOH-CHOH-2-furyl CI
1-165 C2H5 2-furyl Br I-200 C2H5 CHOH-CHOH-2-furyl Br
1-166 C2H5 2-furyl CHF2 1-201 C2H5 CHOH-CHOH-2-furyl CHF2
1-167 C2H5 2-furyl F I-202 C2H5 CHOH-CHOH-2-furyl F
1-168 C2H5 2-furyl I I-203 C2H5 CHOH-CHOH-2-furyl I
1-169 C2H5 3-furyl CH3 I-204 C2H5 4-methyl-5-oxazolyl CH3
1-170 C2H5 3-furyl OCH3 I-205 C2H5 4-methyl-5-oxazolyl OCH3
1-171 C2H5 3-furyl CI I-206 C2H5 4-methyl-5-oxazolyl CI
1-172 C2H5 3-furyl Br I-207 C2H5 4-methyl-5-oxazolyl Br
1-173 C2H5 3-furyl CHF2 I-208 C2H5 4-methyl-5-oxazolyl CHF2
1-174 C2H5 3-furyl F I-209 C2H5 4-methyl-5-oxazolyl F
1-175 C2H5 3-furyl I 1-210 C2H5 4-methyl-5-oxazolyl I Line R1 R2 R3 Line R1 R2 R3
1-21 1 OCHs CH=CH-CHs CHs I-246 OCHs 3-methyl-2-furyl CHs
1-212 OCHs CH=CH-CHs OCHs I-247 OCHs 3-methyl-2-furyl OCHs
1-213 OCHs CH=CH-CHs CI I-248 OCHs 3-methyl-2-furyl CI
1-214 OCHs CH=CH-CHs Br I-249 OCHs 3-methyl-2-furyl Br
1-215 OCHs CH=CH-CHs CHF2 I-250 OCHs 3-methyl-2-furyl CHF2
1-216 OCHs CH=CH-CHs F 1-251 OCHs 3-methyl-2-furyl F
1-217 OCHs CH=CH-CHs I I-252 OCHs 3-methyl-2-furyl I
1-218 OCHs CH=C(CH2)s CHs I-253 OCHs 2-methyl-3-furyl CHs
1-219 OCHs CH=C(CH2)s OCHs I-254 OCHs 2-methyl-3-furyl OCHs
I-220 OCHs CH=C(CH2)s CI I-255 OCHs 2-methyl-3-furyl CI
1-221 OCHs CH=C(CH2)s Br I-256 OCHs 2-methyl-3-furyl Br
I-222 OCHs CH=C(CH2)s CHF2 I-257 OCHs 2-methyl-3-furyl CHF2
I-223 OCHs CH=C(CH2)s F I-258 OCHs 2-methyl-3-furyl F
I-224 OCHs CH=C(CH2)s I I-259 OCHs 2-methyl-3-furyl I
I-225 OCHs CH=C(CH2)4 CHs I-260 OCHs CHOH-CHOH-C6H5 CHs
I-226 OCHs CH=C(CH2)4 OCHs 1-261 OCHs CHOH-CHOH-C6H5 OCHs
I-227 OCHs CH=C(CH2)4 CI I-262 OCHs CHOH-CHOH-C6H5 CI
I-228 OCHs CH=C(CH2)4 Br I-263 OCHs CHOH-CHOH-C6H5 Br
I-229 OCHs CH=C(CH2)4 CHF2 I-264 OCHs CHOH-CHOH-C6H5 CHF2
I-230 OCHs CH=C(CH2)4 F I-265 OCHs CHOH-CHOH-C6H5 F
1-231 OCHs CH=C(CH2)4 I I-266 OCHs CHOH-CHOH-C6H5 I
I-232 OCHs 2-furyl CHs I-267 OCHs CHOH-CHOH-2-furyl CHs
I-233 OCHs 2-furyl OCHs I-268 OCHs CHOH-CHOH-2-furyl OCHs
I-234 OCHs 2-furyl CI I-269 OCHs CHOH-CHOH-2-furyl CI
I-235 OCHs 2-furyl Br I-270 OCHs CHOH-CHOH-2-furyl Br
I-236 OCHs 2-furyl CHF2 1-271 OCHs CHOH-CHOH-2-furyl CHF2
I-237 OCHs 2-furyl F I-272 OCHs CHOH-CHOH-2-furyl F
I-238 OCHs 2-furyl I I-273 OCHs CHOH-CHOH-2-furyl I
I-239 OCHs 3-furyl CHs I-274 OCHs 4-methyl-5-oxazolyl CHs
I-240 OCHs 3-furyl OCHs I-275 OCHs 4-methyl-5-oxazolyl OCHs
1-241 OCHs 3-furyl CI I-276 OCHs 4-methyl-5-oxazolyl CI
I-242 OCHs 3-furyl Br I-277 OCHs 4-methyl-5-oxazolyl Br
I-243 OCHs 3-furyl CHF2 I-278 OCHs 4-methyl-5-oxazolyl CHF2
I-244 OCHs 3-furyl F I-279 OCHs 4-methyl-5-oxazolyl F
I-245 OCHs 3-furyl I I-280 OCHs 4-methyl-5-oxazolyl I The specific number for each single compound is deductible as follows:
Compound 1.1 .1-3 e.g. comprises the compound of formula 1.1 from Table 1 and line I-3 from Table A; To widen the spectrum of action and to achieve synergistic effects, 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,
isoxazolidinones, nitriles, N-phenylphthalimides, oxadiazoles, oxazolidinediones,
oxyacetamides, phenoxycarboxylic acids, phenylcarbamates, phenylpyrazoles,
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.
It may furthermore be beneficial to apply the 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. Also of interest is the 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.
In one embodiment of the present invention the 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).
In a preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.1 ) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (I.2) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.3) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (I.4) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (1.5) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of for- mula (1.6) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.7) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active com- pound A or component A at least one, preferably exactly one, pyridine compound of formula (1.8) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.9) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.10) (corresponds to pyridine compound of formula (I)), as defined herein;
Preferred compounds of the formula (I) which, as component A, are constituent of the composition according to the invention are the compounds 1.1 to 1.10, as defined above;
In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.1 1 ) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of for- mula (1.1 1. A) (corresponds to pyridine compound of formula (I)), as defined herein;
In another preferred embodiment of the invention, the composition comprises as active compound A or component A at least one, preferably exactly one, pyridine compound of formula (1.1 1.C) (corresponds to pyridine compound of formula (I)), as defined herein;
In another embodiment of the present invention the 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):
b1 ) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors);
b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors (PPO inhibitors);
b5) bleacher herbicides;
b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors);
b7) glutamine synthetase inhibitors; b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);
b9) mitosis inhibitors;
b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);
b1 1 ) cellulose biosynthesis inhibitors;
b12) decoupler herbicides;
b13) auxinic herbicides;
b14) auxin transport inhibitors; and
b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat- metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flam- prop-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-dym- ron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinocla- mine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters;
including their agriculturally acceptable salts or derivatives;
In one embodiment of the invention, the compositions contain at least one inhibitor of the lipid biosynthesis (herbicide b1 ). These compounds inhibit lipid biosynthesis. Inhibition of the lipid bi- osynthesis can be affected either through inhibition of acetylCoA carboxylase (hereinafter- termed ACCase herbicides) or through a different mode of action (hereinafter termed non-AC- Case herbicides). The ACCase herbicides belong to the group A of the HRAC classification system whereas the non-ACCase herbicides belong to the group N of the HRAC classification. In another embodiment of the invention, the compositions contain at least one ALS inhibitor (herbicide b2). The herbicidal activity of these compounds is based on the inhibition of acetolac- tate synthase and thus on the inhibition of the branched chain amino acid biosynthesis. These inhibitors belong to the group B of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one inhibitor of photosynthesis (herbicide b3). The herbicidal activity of these compounds is based either on the in- hibition of the photosystem II in plants (so-called PSIl inhibitors, groups C1 , C2 and C3 of HRAC classification) or on diverting the electron transfer in photosystem I in plants (so-called PSI inhibitors, group D of HRAC classification) and thus on an inhibition of photosynthesis. Amongst these, PSIl inhibitors are preferred.
In another embodiment of the invention, the compositions contain at least one inhibitor of pro- toporphyrinogen-IX-oxidase (herbicide b4). The herbicidal activity of these compounds is based on the inhibition of the protoporphyrinogen-IX-oxidase. These inhibitors belong to the group E of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one bleacher-herbicide (herbicide b5). The herbicidal activity of these compounds is based on the inhibition of the carotenoid biosynthesis. These include compounds which inhibit carotenoid biosynthesis by inhibition of phytoene desaturase (so-called PDS inhibitors, group F1 of HRAC classification), compounds that inhibit the 4-hydroxyphenylpyruvate-dioxygenase (HPPD inhibitors, group F2 of HRAC classification), compounds that inhibit DOXsynthase (group F4 of HRAC class) and compounds which inhibit carotenoid biosynthesis by an unknown mode of action (bleacher - unknown target, group F3 of HRAC classification).
In another embodiment of the invention, the compositions contain at least one EPSP synthase inhibitor (herbicide b6). The herbicidal activity of these compounds is based on the inhibition of enolpyruvyl shikimate 3-phosphate synthase, and thus on the inhibition of the amino acid biosynthesis in plants. These inhibitors belong to the group G of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one glutamine synthetase inhibitor (herbicide b7). The herbicidal activity of these compounds is based on the inhi- bition 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.
In another embodiment of the invention, the compositions contain at least one DHP synthase inhibitor (herbicide b8). The herbicidal activity of these compounds is based on the inhibition of 7,8-dihydropteroate synthase. These inhibitors belong to the group I of the HRAC classification system.
In another embodiment of the invention, the compositions contain at least one mitosis inhibitor (herbicide b9). The herbicidal activity of these compounds is based on the disturbance or inhibition of microtubule formation or organization, and thus on the inhibition of mitosis. These inhibitors belong to the groups K1 and K2 of the HRAC classification system. Among these, com- pounds of the group K1 , in particular dinitroanilines, are preferred.
In another embodiment of the invention, the compositions contain at least one VLCFA inhibitor (herbicide b10). The herbicidal activity of these compounds is based on the inhibition of the synthesis of very long chain fatty acids and thus on the disturbance or inhibition of cell division in plants. These inhibitors belong to the group K3 of the HRAC classification system.
In another embodiment of the invention, 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.
In another embodiment of the invention, the compositions contain at least one decoupler herbi- cide (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.
In another embodiment of the invention, the compositions contain at least one auxinic herbicide (herbicide b13). These include compounds that mimic auxins, i.e. plant hormones, and affect the growth of the plants. These compounds belong to the group O of the HRAC classifica- tion system.
In another embodiment of the invention, the compositions contain at least one auxin transport inhibitor (herbicide b14). The herbicidal activity of these compounds is based on the inhibition of the auxin transport in plants. These compounds belong to the group P of the HRAC classification system.
As to the given mechanisms of action and classification of the active substances, see e.g. "HRAC, Classification of Herbicides According to Mode of Action", http://www.plantprot.ec- tion.org/hrac/MOA.html). Preference is given to those compositions according to the present invention comprising at least one herbicide B selected from herbicides of class b1 , b2, b3, b4, b5, b6, b9, b10, b13, and b14.
Specific preference is given to those compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, b13, and b14.
Particular preference is given to those compositions according to the present invention which comprise at least one herbicide B selected from the herbicides of class b1 , b2, b4, b5, b9, b10, and b13
Examples of herbicides B which can be used in combination with the compound of formula (I) according to the present invention are:
b1 ) from the group of the lipid biosynthesis inhibitors:
ACC-herbicides such as alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxa- prop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pi- noxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop- P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim,
4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-py- ran-3(6H)-one (CAS 1312337-72-6); 4-(2,,4,-Dichloro-4-cyclopropyl[1 ,1 ,-biphenyl]-3-yl)-5-hy- droxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-flu- oro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4,-chloro-4-cyclopropyl-2,-fluoro[1 ,1 ,-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'-di- chloro-4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5- (Acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H- pyran-3-one (CAS 1312340-82-1 ); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6- dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'- fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51 -1 ); 4-(2',4'-Dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro- 2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-flu- oro[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2,,4,-Dichloro-4-ethyl[1 ,1 ,-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); and non ACC herbicides such as benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tio- carbazil, triallate and vernolate;
b2) from the group of the ALS inhibitors:
sulfonylureas such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlo- rimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsul- furon-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosul- furon, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primi- sulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron- ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfu- ron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfu- ron-methyl and tritosulfuron,
imidazolinones such as imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, ima- zapyr, imazaquin and imazethapyr, triazolopyrimidine herbicides and sulfonanilides such as cloransulam, cloransulam-methyl, diclosulam, flumetsulam, florasulam, metosulam, penoxsu- lam, pyrimisulfan and pyroxsulam,
pyrimidinylbenzoates such as bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyrimino- bac, pyriminobac-methyl, pyrithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methylethyl ester (CAS 420138-41 -6), 4-[[[2-[(4,6- dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40- 5), N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS
420138-01 -8),
sulfonylaminocarbonyl-triazolinone herbicides such as flucarbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thiencarbazone and thiencarbazone-methyl; and triafamone;
among these, a preferred embodiment of the invention relates to those compositions comprising at least one imidazolinone herbicide;
b3) from the group of the photosynthesis inhibitors:
amicarbazone, inhibitors of the photosystem II, e.g. 1 -(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1 -(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butyl-1 -methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1 -methyl-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1-me- thoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4-hy- droxy-1 ,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5- ethoxy-4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69- 4), 4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1 ,5-dimethyl-3-[1 -methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1 ), triazine herbicides, including of chlorotriazine, triazinones, triazindiones, methylthiotriazines and pyridazinones such as ametryn, atrazine, chloridazone, cyanazine, des- metryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, propazine, simazine, sim- etryn, terbumeton, terbuthylazin, terbutryn and trietazin, aryl urea such as chlorobromuron, chlo- rotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metam- itron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, siduron, tebuthi- uron and thiadiazuron, phenyl carbamates such as desmedipham, karbutilat, phenmedipham, phenmedipham-ethyl, nitrile herbicides such as bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, uraciles such as bromacil, lenacil and terbacil, and benta- zon and bentazon-sodium, pyridate, pyridafol, pentanochlor and propanil and inhibitors of the photosystem I such as diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat- dimetilsulfate. Among these, a preferred embodiment of the invention relates to those compositions comprising at least one aryl urea herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one triazine herbicide. Among these, likewise a preferred embodiment of the invention relates to those compositions comprising at least one nitrile herbicide;
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
acifluorfen, acifluorfen-sodium, azafenidin, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, chlorphthalim, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluorogly- cofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyradonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfen- trazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoro- methyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292- 31-6; S-3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 A -pyrazole-1 -car- boxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5- methyl-1 pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoro- methylphenoxy)-5-methyl-1 A/-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl- 3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 A/-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dime- thyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2- ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS
13001 18-96-0), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H- benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), methyl (£)-4-[2-chloro-5- [4-chloro-5-(difluoromethoxy)-1 A -methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-eno- ate (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazol-4-yl]-1-me- thyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS 212754-02-4);
b5) from the group of the bleacher herbicides:
PDS inhibitors: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone, norflurazon, picolinafen, and 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS
180608-33-7), HPPD inhibitors: benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquinotrione, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21 -3), pyrasulfotole, pyrazol- ynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone , bleacher, unknown target: aclonifen, amitrole flumeturon,2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5- yl)-4-(trifluoromethyl)benzamide (CAS 1361 139-71 -0), 2-(2,4-dichlorophenyl)methyl-4,4-dime- thyl-3-isoxazolidone (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxa- zolidinone (CAS 81778-66-7);
b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammo- nium, glyposate-potassium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos- sodium, glufosinate, glufosinate-P and glufosinate-ammonium;
b8) from the group of the DHP synthase inhibitors: asulam;
b9) from the group of the mitosis inhibitors: compounds of group K1 : dinitroanilines such as benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphoramidates such as ami- prophos, amiprophos-methyl, and butamiphos, benzoic acid herbicides such as chlorthal, chlor- thal-dimethyl, pyridines such as dithiopyr and thiazopyr, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl and propham ; among these, compounds of group K1 , in particular dinitroanilines are preferred;
b10) from the group of the VLCFA inhibitors:
chloroacetamides such as acetochlor, alachlor, amidochlor, butachlor, dimethachlor, dimethe- namid, dimethenamid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, propisochlor and thenylchlor, oxyacetanilides such as flufenacet and mefenacet, ac- etanilides such as diphenamid, naproanilide, napropamide and napropamide-M, tetrazolinones such fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfen- carbazone, piperophos, pyroxasulfone and isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
Figure imgf000059_0001
the isoxazoline compounds are known in the art, e.g. from WO 2006/024820, WO
2006/037945, WO 2007/071900 and WO 2007/096576;
among the VLCFA inhibitors, preference is given to chloroacetamides and oxyacetamides; b1 1 ) from the group of the cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1 -cyclohexyl-5-pentafluorphenyloxy-14- [1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );
b12) from the group of the decoupler herbicides: dinoseb, dinoterb and DNOC and its salts; b13) from the group of the auxinic herbicides:
2,4-D and its salts and esters such as clacyfos, 2,4-DB and its salts and esters, aminocyclopy- rachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammo- nium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, flopyrauxifen, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9) and 4-amino- 3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
b14) from the group of the auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, nap- talam and naptalam-sodium;
b15) from the group of the other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3 and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, inda- nofan, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine and tridiphane.
Preferred herbicides B that can be used in combination with the pyridine compounds of the formula (I) according to the present invention are:
b1 ) from the group of the lipid biosynthesis inhibitors:
clethodim, clodinafop-propargyl, cycloxydim, cyhalofop-butyl, diclofop-methyl, fenoxaprop-P- ethyl, fluazifop-P-butyl, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepraloxydim, tralkoxydim, 4-(4'-Chloro-4- cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-Dichloro-4-cyclopropyl[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetra- methyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3- yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4- ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetra- methyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 ,1 '- biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4'-chloro-4- ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS
1312340-82-1 ); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6- tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-bi- phenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1 ); 4-(2',4'-Dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1 '- biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetrame- thyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, dimepiperate, EPTC, esprocarb, ethofumesate, molinate, orbencarb, prosulfocarb, thiobencarb and triallate;
b2) from the group of the ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron-methyl, bispyribac-sodium, chlorimuron-ethyl, chlor- sulfuron, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron-methyl, ethoxysul- furon, flazasulfuron, florasulam, flucarbazone-sodium, flucetosulfuron, flumetsulam, flupyrsulfu- ron-methyl-sodium, foramsulfuron, halosulfuron-methyl, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl- sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, metosulam, met- sulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron-methyl, propoxycarbazon-sodium, propyrisulfuron, prosulfuron, pyrazosulfuron-ethyl, pyribenzoxim, py- rimisulfan, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium, pyroxsulam, rimsulfuron, sulfome- turon-methyl, sulfosulfuron, thiencarbazone-methyl, thifensulfuron-methyl, triasulfuron, tribenu- ron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron and triafamone;
b3) from the group of the photosynthesis inhibitors:
ametryn, amicarbazone, atrazine, bentazone, bentazone-sodium, bromoxynil and its salts and esters, chloridazone, chlorotoluron, cyanazine, desmedipham, diquat-dibromide, diuron, fluome- turon, hexazinone, ioxynil and its salts and esters, isoproturon, lenacil, linuron, metamitron, methabenzthiazuron, metribuzin, paraquat, paraquat-dichloride, phenmedipham, propanil, pyri- date, simazine, terbutryn, terbuthylazine, thidiazuron, 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4- methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy- 4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1 -(5-tert-butylisoxazol-3-yl)-4-chloro- 2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butyl-1 -methyl-pyrazol-3-yl)- 4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1654057-29-0), 1-(5-tert-butyl-1 -methyl-py- razol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS 1654747-80-4), 4-hydroxy-1 - methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one; (CAS 2023785-78-4), 4- hydroxy-1 ,5-dimethyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 2023785-79-5), 5- ethoxy-4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1701416-69- 4), 4-hydroxy-1 -methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS 1708087-22-2), 4-hydroxy-1 ,5-dimethyl-3-[1 -methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS 2023785-80-8) and 1 -(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1 );
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors:
acifluorfen-sodium, bencarbazone, benzfendizone, butafenacil, carfentrazone-ethyl, cinidon- ethyl, flufenpyr-ethyl, flumiclorac-pentyl, flumioxazin, fluoroglycofen-ethyl, fomesafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, pyraflufen, pyraflufen-ethyl, saflufenacil, sul- fentrazone, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl- 2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6; S- 3100), N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 A/-pyrazole-1 -carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H- pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphe- noxy)-5-methyl-1 A/-pyrazole-1 -carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chlo- ro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1 A -pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo- [1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihy- dro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 13001 18-96-0); 1 - methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin- 6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)- 1 H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS 212754-02-4); b5) from the group of the bleacher herbicides:
aclonifen, amitrole, beflubutamid, benzobicyclon, bicyclopyrone, clomazone, diflufenican, fenquinotrione, flumeturon, flurochloridone, flurtamone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), norflurazon, picolinafen, pyrasulfotole, pyrazolynate, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)- pyrimidine (CAS 180608-33-7), 2-chloro-3-methylsulfanyl-N-(1 -methyltetrazol-5-yl)-4-(trifluoro- methyl)benzamide (CAS 1361 139-71-0, 2-(2,4-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazoli- done (CAS 81777-95-9) and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7);
b6) from the group of the EPSP synthase inhibitors:
glyphosate, glyphosate-isopropylammonium, glyphosate-potassium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors:
glufosinate, glufosinate-P, glufosinate-ammonium;
b8) from the group of the DHP synthase inhibitors: asulam;
b9) from the group of the mitosis inhibitors:
benfluralin, dithiopyr, ethalfluralin, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M- isopropyl, flamprop-M-methyl, oryzalin, pendimethalin, thiazopyr and trifluralin;
b10) from the group of the VLCFA inhibitors: acetochlor, alachlor, amidochlor, anilofos, buta- chlor, cafenstrole, dimethenamid, dimethenamid-P, fentrazamide, flufenacet, mefenacet, meta- zachlor, metolachlor, S-metolachlor, naproanilide, napropamide, napropamide-M, pretilachlor, fenoxasulfone, ipfencarbazone, pyroxasulfone thenylchlor and isoxazoline-compounds of the formulae 11.1 , II.2, 11.3 , II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
b1 1 ) from the group of the cellulose biosynthesis inhibitors: dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS 175899-01 -1 );
b13) from the group of the auxinic herbicides:
2,4-D and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammoni- um and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, dichlor- prop-P and its salts and esters, flopyrauxifen, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8), MCPA and its salts and esters, MCPB and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quinmerac, triclopyr and its salts and esters, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
b14) from the group of the auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium; b15) from the group of the other herbicides: bromobutide, cinmethylin, cumyluron, cyclopy- rimorate (CAS 499223-49-3) and its salts and esters, dalapon, difenzoquat, difenzoquat- metilsulfate, DSMA, dymron (= daimuron), indanofan, metam, methylbromide, MSMA, oxazi- clomefone, pyributicarb and tridiphane.
Particularly preferred herbicides B that can be used in combination with the pyridine compounds of the formula (I) according to the present invention are: b1 ) 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-tetra- methyl-2H-pyran-3(6H)-one (CAS 1312337-45-3); 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3- yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4- ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3);
5- (Acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetra- methyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(Acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 ,1 '- biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(Acetyloxy)-4-(4'-chloro-4- ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS
1312340-82-1 ); 5-(Acetyloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6- tetramethyl-2H-pyran-3-one (CAS 1033760-55-2); 4-(4'-Chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-bi- phenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51-1 ); 4-(2',4'-Dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6- tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-Chloro-4-ethyl-2'-fluoro[1 ,1 '- biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetrame- thyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); esprocarb, prosul- focarb, thiobencarb and triallate;
b2) from the group of the ALS inhibitors: bensulfuron-methyl, bispyribac-sodium, cyclosulfamu- ron, diclosulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imaza- pic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodi- um, iofensulfuron, iofensulfuron-sodium, mesosulfuron, metazosulfuron, nicosulfuron, penoxsu- lam, propoxycarbazon-sodium, propyrisulfuron, pyrazosulfuron-ethyl, pyroxsulam, rimsulfuron, sulfosulfuron, thiencarbazon-methyl, tritosulfuron and triafamone;
b3) from the group of the photosynthesis inhibitors: ametryn, atrazine, diuron, fluometuron, hexazinone, isoproturon, linuron, metribuzin, paraquat, paraquat-dichloride, propanil, terbutryn, terbuthylazine, 1 -(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1 ), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2- one (CAS 1844836-64-1 );
b4) from the group of the protoporphyrinogen-IX oxidase inhibitors: flumioxazin, oxyfluorfen, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, trifludimoxazin, ethyl [3-[2-chloro-4-flu- oro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyl- oxy]acetate (CAS 353292-31 -6; S-3100, 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-ben- zo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo-[1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7- trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole- 1 ,3-dione (CAS 13001 18-96-0), and 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2- ynyl-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0);
b5) from the group of the bleacher herbicides: amitrole, bicyclopyrone, clomazone, diflufeni- can, fenquinotrione, flumeturon, flurochloridone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, 2- chloro-3-methylsulfanyl-N-(1 -methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 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-dimethyl-3-isoxazolidinone (CAS 81778-66-7);
b6) from the group of the EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammo- nium and glyphosate-trimesium (sulfosate);
b7) from the group of the glutamine synthase inhibitors: glufosinate, glufosinate-P and glufosinate-ammonium;
b9) from the group of the mitosis inhibitors: pendimethalin and trifluralin;
b10) from the group of the VLCFA inhibitors: acetochlor, cafenstrole, dimethenamid-P, fentra- zamide, flufenacet, mefenacet, metazachlor, metolachlor, S-metolachlor, fenoxasulfone, ipfen- carbazone and pyroxasulfone; likewise, preference is given to isoxazoline compounds of the formulae 11.1 , II.2, 11.3 , II.4, II.5, II.6, II.7, II.8 and II.9 as mentioned above;
b1 1 ) from the group of the cellulose biosynthesis inhibitors: indaziflam, isoxaben and tria- ziflam;
b13) from the group of the auxinic herbicides: 2,4-D and its salts and esters such as clacyfos, and aminocyclopyrachlor and its salts and esters, aminopyralid and its salts and its esters, clopyralid and its salts and esters, dicamba and its salts and esters, flopyrauxifen, fluroxypyr- meptyl, halauxifen, halauxifen-methyl, quinclorac, quinmerac, florpyrauxifen, florpyrauxifen-ben- zyl (CAS 1390661 -72-9) and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6);
b14) from the group of the auxin transport inhibitors: diflufenzopyr and diflufenzopyr-sodium, b15) from the group of the other herbicides: cinmethylin, dymon (= daimuron), indanofan, oxa- ziclomefone.
Particularly preferred herbicides B are the herbicides B as defined above; in particular, the herbicides B.1 - B.202 listed below in table B:
Table B
B Herbicide B B Herbicide B
B.1 clethodim B.19 bensulfuron-methyl
B.2 clodinafop-propargyl B.20 bispyribac-sodium
B.3 cycloxydim B.21 cloransulam-methyl
B.4 cyhalofop-butyl B.22 chlorsulfuron
B.5 fenoxaprop-ethyl B.23 clorimuron
B.6 fenoxaprop-P-ethyl B.24 cyclosulfamuron
B.7 metamifop B.25 diclosulam
B.8 pinoxaden B.26 florasulam
B.9 profoxydim B.27 flumetsulam
B.10 sethoxydim B.28 flupyrsulfuron-methyl-sodium
B.1 1 tepraloxydim B.29 foramsulfuron
B.12 tralkoxydim B.30 imazamox
B.13 esprocarb B.31 imazamox-ammonium
B.14 ethofumesate B.32 imazapic
B.15 molinate B.33 imazapic-ammonium
B.16 prosulfocarb B.34 imazapic-isopropylammonium
B.17 thiobencarb B.35 imazapyr
B.18 triallate B.36 imazapyr-ammonium B Herbicide B B Herbicide B
B.37 imazapyr-isopropylammonium B.79 metribuzin
B.38 imazaquin B.80 propanil
B.39 imazaquin-ammonium B.81 simazin
B.40 imazethapyr B.82 terbuthylazine
B.41 imazethapyr-ammonium B.83 terbutryn
B.42 imazethapyr-isopropylammonium B.84 paraquat-dichloride
B.43 imazosulfuron B.85 acifluorfen
B.44 iodosulfuron-methyl-sodium B.86 butafenacil
B.45 iofensulfuron B.87 carfentrazone-ethyl
B.46 iofensulfuron-sodium B.88 flumioxazin
B.47 mesosulfuron-methyl B.89 fomesafen
B.48 metazosulfuron B.90 oxadiargyl
B.49 metsulfuron-methyl B.91 oxyfluorfen
B.50 metosulam B.92 pyraflufen
B.51 nicosulfuron B.93 pyraflufen-ethyl
B.52 penoxsulam B.94 saflufenacil
B.53 propoxycarbazon-sodium B.95 sulfentrazone
B.54 pyrazosulfuron-ethyl B.96 trifludimoxazin
B.55 pyribenzoxim B.97 ethyl [3-[2-chloro-4-fluoro-5-(1-
B.56 pyriftalid methyl-6-trifluoromethyl-2,4-di-
B.57 pyroxsulam oxo-1 ,2,3,4-tetrahydropyrimidin-
B.58 propyrisulfuron 3-yl)phenoxy]-2-pyridyloxy]ace-
B.59 rimsulfuron tate (CAS 353292-31-6)
B.60 sulfosulfuron B.98 benzobicyclon
B.61 thiencarbazone-methyl B.99 bicyclopyrone
B.62 thifensulfuron-methyl B.100 clomazone
B.63 tribenuron-methyl B.101 diflufenican
B.64 tritosulfuron B.102 flurochloridone
B.65 triafamone B.103 isoxaflutole
B.66 ametryne B.104 mesotrione
B.67 atrazine B.105 norflurazone
B.68 bentazon B.106 picolinafen
B.69 bromoxynil B.107 sulcotrione
B.70 bromoxynil-octanoate B.108 tefuryltrione
B.71 bromoxynil-heptanoate B.109 tembotrione
B.72 bromoxynil-potassium B.1 10 tolpyralate
B.73 diuron B.1 1 1 topramezone
B.74 fluometuron B.1 12 topramezone-sodium
B.75 hexazinone B.1 13 amitrole
B.76 isoproturon B.1 14 fluometuron
B.77 linuron B.1 15 fenquinotrione
B.78 metamitron B.1 16 glyphosate B Herbicide B B Herbicide B
B.1 17 glyphosate-ammonium B.157 dicamba-butotyl
B.1 18 glyphosate-dimethylammonium B.158 dicamba-diglycolamine
B.1 19 glyphosate-isopropylammonium B.159 dicamba-dimethylammonium
B.120 glyphosate-trimesium (sulfosate) B.160 dicamba-diolamine
B.121 glyphosate-potassium B.161 dicamba-isopropylammonium
B.122 glufosinate B.162 dicamba-potassium
B.123 glufosinate-ammonium B.163 dicamba-sodium
B.124 glufosinate-P B.164 dicamba-trolamine
B.125 glufosinate-P-ammonium B.165 dicamba-N,N-bis-(3-
B.126 pendimethalin aminopropyl)methylamine
B.127 trifluralin B.166 dicamba-diethylenetriamine
B.128 acetochlor B.167 fluroxypyr
B.129 butachlor B.168 fluroxypyr-meptyl
B.130 cafenstrole B.169 halauxifen
B.131 dimethenamid-P B.170 halauxifen-methyl
B.132 fentrazamide B.171 MCPA
B.133 flufenacet B.172 MCPA-2-ethylhexyl
B.134 mefenacet B.173 MCPA-dimethylammonium
B.135 metazachlor B.174 quinclorac
B.136 metolachlor B.175 quinclorac-dimethylammonium
B.137 S-metolachlor B.176 quinmerac
B.138 pretilachlor B.177 quinmerac-dimethylammonium
B.139 fenoxasulfone B.178 florpyrauxifen
B.140 indaziflam B.179 florpyrauxifen-benzyl (CAS
B.141 isoxaben 1390661 -72-9)
B.142 triaziflam B.180 aminocyclopyrachlor
B.143 ipfencarbazone B.181 aminocyclopyrachlor-potassium
B.144 pyroxasulfone B.182 aminocyclopyrachlor-methyl
B.145 2,4-D B.183 diflufenzopyr
B.146 2,4-D-isobutyl B.184 diflufenzopyr-sodium
B.147 2,4-D-dimethylammonium B.185 dymron
B.148 2,4-D-N,N,N- B.186 indanofan
trimethylethanolammonium B.187 oxaziclomefone
B.149 aminopyralid B.188 11.1
B.150 aminopyralid-methyl B.189 W .2
B.151 aminopyralid-dimethylammonium B.190 11.3
B.152 aminopyralid-tris(2-hydroxypro- B.191 I I.4
pyl)ammonium B.192 I I.5
B.153 clopyralid B.193 I I.6
B.154 clopyralid-methyl B.194 I I.7
B.155 clopyralid-olamine B.195 11.8
B.156 dicamba B.196 i i.g B Herbicide B B Herbicide B
B.197 4-amino-3-chloro-5-fluoro-6-(7- B.201 2-chloro-3-methylsulfanyl-N-(1 - fluoro-1 H-indol-6-yl)picolinic acid methyltetrazol-5-yl)-4-(trifluoro- (CAS 1629965-65-6) methyl)benzamide (CAS
B.198 flopyrauxifen 1361 139-71-0)
B.199 oxotrione (CAS 1486617-21-3) B.202 2-(2,4-dichlorophenyl)methyl-4,4-
B.200 cinmethylin dimethyl-3-isoxazolidone (CAS
81777-95-9)
In another embodiment of the present invention the compositions according to the present invention comprise at least one pyridine 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 pyridine 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 agriculturally acceptable salts and their agriculturally acceptable derivatives such amides, esters, and thioesters, provided they have an acid group.
Examples of preferred safeners C are benoxacor, cloquintocet, cyometrinil, cyprosulfamide, dichlormid, dicyclonon, dietholate, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalic anhydride, oxabetrinil, 4-(dichloroacetyl)-1 -oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxa- zolidine (R-29148, CAS 52836-31-4), metcamifen and BPCMS (CAS 54091 -06-4).
Especially preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, naphthalic anhy- dride, oxabetrinil, 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4) and metcamifen.
Particularly preferred safeners C are benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, naphtalic anhydride, 4-(dichloroace- tyl)-1-oxa-4-azaspiro[4.5]decane (MON4660, CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroace- tyl)-1 ,3-oxazolidine (R-29148, CAS 52836-31 -4) and metcamifen.
Particularly preferred safeners C, which, as component C, are constituent of the composition according to the invention are the safeners C as defined above; in particular the safeners C.1 - C.17 listed below in table C:
Table C:
c Safener C
C.1 benoxacor C.2 cloquintocet
C.3 cloquintocet-mexyl
C.4 cyprosulfamide
C.5 dichlormid
C.6 fenchlorazole
C.7 fenchlorazole-ethyl
C.8 fenclorim
C.9 furilazole
C.10 isoxadifen
C.1 1 isoxadifen-ethyl
C.12 mefenpyr
C.13 mefenpyr-diethyl
C.14 naphtalic acid anhydride
C.15 4-(dichloroacetyl)-1 -oxa-4- azaspiro[4.5]decane
(MON4660, CAS 71526-07-3)
C.16 2,2,5-trimethyl-3-(dichloroace- tyl)-1 ,3-oxazolidine (R-29148,
CAS 52836-31 -4)
C.17 metcamifen
The active compounds B of groups b1 ) to b15) and the active compounds C are known herbicides and safeners, see, e.g., The Compendium of Pesticide Common Names (http://www.alan- wood.net/pesticides/); Farm Chemicals Handbook 2000 volume 86, Meister Publishing Company, 2000; B. Hock, C. Fedtke, R. R. Schmidt, Herbizide [Herbicides], Georg Thieme Verlag, Stuttgart 1995; W. H. Ahrens, Herbicide Handbook, 7th edition, Weed Science Society of America, 1994; and K. K. Hatzios, Herbicide Handbook, Supplement for the 7th edition, Weed Science Society of America, 1998. 2,2,5-Trimethyl-3-(dichloroacetyl)-1 ,3-oxazolidine [CAS No. 52836-31-4] is also referred to as R-29148. 4-(Dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane [CAS No. 71526-07-3] is also referred to as AD-67 and MON 4660.
The assignment of the active compounds to the respective mechanisms of action is based on current knowledge. If several mechanisms of action apply to one active compound, this substance was only assigned to one mechanism of action.
Active compounds B and C having a carboxyl group can be employed in the form of the acid, in the form of an agriculturally suitable salt as mentioned above or else in the form of an agricul- turally acceptable derivative in the compositions according to the invention.
In the case of dicamba, suitable salts include those, where the counterion is an agriculturally acceptable cation. E.g., suitable salts of dicamba are dicamba-sodium, dicamba-potassium, dicamba-methylammonium, dicamba-dimethylammonium, dicamba-isopropylammonium, dicamba-diglycolamine, dicamba-olamine, dicamba-diolamine, dicamba-trolamine, dicamba- N,N-bis-(3-aminopropyl)methylamine and dicamba-diethylenetriamine. Examples of a suitable ester are dicamba-methyl and dicamba-butotyl.
Suitable salts of 2,4-D are 2,4-D-ammonium, 2,4-D-dimethylammonium, 2,4-D-diethylammoni- um, 2,4-D-diethanolammonium (2,4-D-diolamine), 2,4-D-triethanolammonium, 2,4-D-isoprop- ylammonium, 2,4-D-triisopropanolammonium, 2,4-D-heptylammonium, 2,4-D-dodecylammo- nium, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammo- nium, 2,4-D-tris(isopropyl)ammonium, 2,4-D-trolamine, 2,4-D-lithium, 2,4-D-sodium. Examples of suitable esters of 2,4-D are 2,4-D-butotyl, 2,4-D-2-butoxypropyl, 2,4-D-3-butoxypropyl, 2,4-D- butyl, 2,4-D-ethyl, 2,4-D-ethylhexyl, 2,4-D-isobutyl, 2,4-D-isooctyl, 2,4-D-isopropyl, 2,4-D-mep- tyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-propyl, 2,4-D-tefuryl and clacyfos.
Suitable salts of 2,4-DB are e.g. 2,4-DB-sodium, 2,4-DB-potassium and 2,4-DB-dimethyl- ammonium. Suitable esters of 2,4-DB are e.g. 2,4-DB-butyl and 2,4-DB-isoctyl.
Suitable salts of dichlorprop are e.g. dichlorprop-sodium, dichlorprop-potassium and dichlor- prop-dimethylammonium. Examples of suitable esters of dichlorprop are dichlorprop-butotyl and dichlorprop-isoctyl.
Suitable salts and esters of MCPA include MCPA-butotyl, MCPA-butyl, MCPA-dimethylammo- nium, MCPA-diolamine, MCPA-ethyl, MCPA-thioethyl, MCPA-2-ethylhexyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-isopropylammonium, MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium and MCPA-trolamine.
A suitable salt of MCPB is MCPB sodium. A suitable ester of MCPB is MCPB-ethyl.
Suitable salts of clopyralid are clopyralid-potassium, clopyralid-olamine and clopyralid-tris-(2- hydroxypropyl)ammonium. Example of suitable esters of clopyralid is clopyralid-methyl.
Examples of a suitable ester of fluroxypyr are fluroxypyr-meptyl and fluroxypyr-2-butoxy-1- methylethyl, wherein fluroxypyr-meptyl is preferred.
Suitable salts of picloram are picloram-dimethylammonium, picloram-potassium, picloram- triisopropanolammonium, picloram-triisopropylammonium and picloram-trolamine. A suitable ester of picloram is picloram-isoctyl.
A suitable salt of triclopyr is triclopyr-triethylammonium. Suitable esters of triclopyr are e.g. triclopyr-ethyl and triclopyr-butotyl.
Suitable salts and esters of chloramben include chloramben-ammonium, chloramben-diola- mine, chloramben-methyl, chloramben-methylammonium and chloramben-sodium. Suitable salts and esters of 2,3,6-TBA include 2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6- TBA-potassium and 2,3,6-TBA-sodium.
Suitable salts and esters of aminopyralid include aminopyralid-potassium, aminopyralid-dime- thylammonium, and aminopyralid-tris(2-hydroxypropyl)ammonium.
Suitable salts of glyphosate are e.g. glyphosate-ammonium, glyphosate-diammonium, glyphoste-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glypho- sate-sodium, glyphosate-trimesium as well as the ethanolamine and diethanolamine salts, pref- erably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimesium (sul- fosate).
A suitable salt of glufosinate is e.g. glufosinate-ammonium.
A suitable salt of glufosinate-P is e.g. glufosinate-P-ammonium.
Suitable salts and esters of bromoxynil are e.g. bromoxynil-butyrate, bromoxynil-heptanoate, bromoxynil-octanoate, bromoxynil-potassium and bromoxynil-sodium.
Suitable salts and esters of ioxonil are e.g. ioxonil-octanoate, ioxonil-potassium and ioxonil- sodium. Suitable salts and esters of mecoprop include mecoprop-butotyl, mecoprop-dimethylammo- nium, mecoprop-diolamine, mecoprop-ethadyl, mecoprop-2-ethylhexyl, mecoprop-isoctyl, mecoprop-methyl, mecoprop-potassium, mecoprop-sodium and mecoprop-trolamine.
Suitable salts of mecoprop-P are e.g. mecoprop-P-butotyl, mecoprop-P-dimethylammonium, mecoprop-P-2-ethylhexyl, mecoprop-P-isobutyl, mecoprop-P-potassium and mecoprop-P-so- dium.
A suitable salt of diflufenzopyr is e.g. diflufenzopyr-sodium.
A suitable salt of naptalam is e.g. naptalam-sodium.
Suitable salts and esters of aminocyclopyrachlor are e.g. aminocyclopyrachlor-dimethylammo- nium, aminocyclopyrachlor-methyl, aminocyclopyrachlor-triisopropanolammonium, aminocyclo- pyrachlor-sodium and aminocyclopyrachlor-potassium.
A suitable salt of quinclorac is e.g. quinclorac-dimethylammonium.
A suitable salt of quinmerac is e.g. quinmerac-dimethylammonium.
A suitable salt of imazamox is e.g. imazamox-ammonium.
Suitable salts of imazapic are e.g. imazapic-ammonium and imazapic-isopropylammonium.
Suitable salts of imazapyr are e.g. imazapyr-ammonium and imazapyr-isopropylammonium.
A suitable salt of imazaquin is e.g. imazaquin-ammonium.
Suitable salts of imazethapyr are e.g. imazethapyr-ammonium and imazethapyr-isoprop- ylammonium.
A suitable salt of topramezone is e.g. topramezone-sodium.
According to a preferred embodiment of the invention, the composition comprises as herbicidal active compound B or component B at least one, preferably exactly one herbicide B.
According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least two, preferably exactly two herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as herbicidal active compounds B or component B at least three, preferably exactly three herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as safening component C or component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component B at least one, preferably exactly one herbicide B, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises at least two, preferably exactly two, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises at least three, preferably exactly three, herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .3), especially preferred the compound (1.3.1-3), (1.3.1-4), (1 .3.1-10), (1.3.1-1 1 ), (1.3.1- 17), (1.3.1-18), (1.3.1-24), (1 .3.1-25), (1.3.1-31 ), (1 .3.1-32), (1 .3.1-38), (1.3.1-39), (1.3.1-45), (1 .3.1- 46), (1.3.1-52), (1.3.1-53), (1 .3.1-59), (1.3.1-60), (1 .3.1-66), or (1.3.1-67), and as component B at least one, preferably exactly one, herbicide B.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .3), especially preferred the compound (1.3.1-3), (1.3.1-4), (1 .3.1-10), (1.3.1-1 1 ), (1.3.1- 17), (1.3.1-18), (1.3.1-24), (1 .3.1-25), (1.3.1-31 ), (1 .3.1-32), (1 .3.1-38), (1.3.1-39), (1.3.1-45), (1 .3.1- 46), (1.3.1-52), (1.3.1-53), (1 .3.1-59), (1.3.1-60), (1 .3.1-66), or (1.3.1-67), and at least two, preferably exactly two, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .3), especially preferred the compound (1.3.1-3), (1.3.1-4), (1 .3.1-10), (1.3.1-1 1 ), (1.3.1- 17), (1.3.1-18), (1.3.1-24), (1 .3.1-25), (1.3.1-31 ), (1 .3.1-32), (1 .3.1-38), (1.3.1-39), (1.3.1-45), (1 .3.1- 46), (1.3.1-52), (1.3.1-53), (1 .3.1-59), (1.3.1-60), (1 .3.1-66), or (1.3.1-67), and at least three, preferably exactly three, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .3), especially preferred the compound (1.3.1-3), (1.3.1-4), (1 .3.1-10), (1.3.1-1 1 ), (1.3.1- 17), (1.3.1-18), (1.3.1-24), (1 .3.1-25), (1.3.1-31 ), (1 .3.1-32), (1 .3.1-38), (1.3.1-39), (1.3.1-45), (1 .3.1- 46), (1.3.1-52), (1.3.1-53), (1 .3.1-59), (1.3.1-60), (1 .3.1-66), or (1.3.1-67), and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .3), especially preferred the compound (1.3.1-3), (1.3.1-4), (1 .3.1-10), (1.3.1-1 1 ), (1.3.1- 17), (1.3.1-18), (1.3.1-24), (1 .3.1-25), (1.3.1-31 ), (1 .3.1-32), (1 .3.1-38), (1.3.1-39), (1.3.1-45), (1 .3.1- 46), (1.3.1-52), (1.3.1-53), (1 .3.1-59), (1.3.1-60), (1 .3.1-66), or (1.3.1-67), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly pyridine compound of formula (I), preferably of for- mula (1.3), especially preferred the compound (1 .3.1-3), (1 .3.1-4), (1.3.1-10), (1.3.1-1 1 ), (1 .3.1-17), (1.3.1-18), (1 .3.1-24), (1.3.1-25), (1 .3.1-31 ), (1.3.1-32), (1 .3.1-38), (1.3.1-39), (1 .3.1-45), (1.3.1-46), (1.3.1-52), (1 .3.1-53), (1.3.1-59), (1 .3.1-60), (1.3.1-66), or (1.3.1-67), at least two, preferably exactly two herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .3), especially preferred the compound (1.3.1-3), (1.3.1-4), (1 .3.1-10), (1.3.1-1 1 ), (1.3.1- 17), (1.3.1-18), (1.3.1-24), (1 .3.1-25), (1.3.1-31 ), (1 .3.1-32), (1 .3.1-38), (1.3.1-39), (1.3.1-45), (1 .3.1- 46), (1.3.1-52), (1.3.1-53), (1 .3.1-59), (1.3.1-60), (1 .3.1-66), or (1.3.1-67), at least three, preferably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .15), especially preferred the compound (1.15.1-3), (1.15.1-4), (1 .15.1-10), (1 .15.1-1 1 ), (1.15.1-17), (1.15.1-18), (1.15.1-24), (1.15.1-25), (1.15.1-31 ), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1-46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), or (1 .15.1-67), and as component B at least one, preferably exactly one, herbicide B.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .15), especially preferred the compound (1.15.1-3), (1.15.1-4), (1 .15.1-10), (1 .15.1-1 1 ), (1.15.1-17), (1.15.1-18), (1.15.1-24), (1.15.1-25), (1.15.1-31 ), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1-46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), or (1 .15.1-67), and at least two, preferably exactly two, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .15), especially preferred the compound (1.15.1-3), (1.15.1-4), (1 .15.1-10), (1 .15.1-1 1 ), (1.15.1-17), (1.15.1-18), (1.15.1-24), (1.15.1-25), (1.15.1-31 ), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1-46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), or (1 .15.1-67), and at least three, preferably exactly three, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .15), especially preferred the compound (1.15.1-3), (1.15.1-4), (1 .15.1-10), (1 .15.1-1 1 ), (1.15.1-17), (1.15.1-18), (1.15.1-24), (1.15.1-25), (1.15.1-31 ), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1-46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), or (1 .15.1-67), and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .15), especially preferred the compound (1.15.1-3), (1.15.1-4), (1 .15.1-10), (1 .15.1-1 1 ), (1.15.1-17), (1.15.1-18), (1.15.1-24), (1.15.1-25), (1.15.1-31 ), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1-46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), or (1 .15.1-67), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly pyridine compound of formula (I), preferably of formula (1.15), especially preferred the compound (1.15.1-3), (1.15.1-4), (1 .15.1-10), (1.15.1-1 1 ), (1.15.1-17), (1.15.1-18), (1.15.1-24), (1.15.1-25), (1.15.1-31 ), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1-46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), or (1 .15.1-67), at least two, preferably exactly two herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .15), especially preferred the compound (1.15.1-3), (1.15.1-4), (1 .15.1-10), (1 .15.1-1 1 ), (1.15.1-17), (1.15.1-18), (1.15.1-24), (1.15.1-25), (1.15.1-31 ), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1-46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), or (1 .15.1-67), at least three, preferably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .16), especially preferred the compound (1.16.1-3), (1.16.1-4), (1 .16.1-10), (1 .16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), or (1 .16.1-67), and as component B at least one, preferably exactly one, herbicide B.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .16), especially preferred the compound (1.16.1-3), (1.16.1-4), (1 .16.1-10), (1 .16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), or (1 .16.1-67), and at least two, preferably exactly two, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .16), especially preferred the compound (1.16.1-3), (1.16.1-4), (1 .16.1-10), (1 .16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), or (1 .16.1-67), and at least three, preferably exactly three, herbicides B different from each other.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .16), especially preferred the compound (1.16.1-3), (1.16.1-4), (1 .16.1-10), (1 .16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), or (1 .16.1-67), and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .16), especially preferred the compound (1.16.1-3), (1.16.1-4), (1 .16.1-10), (1 .16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), or (1 .16.1-67), as component B at least one, preferably exactly one, herbicide B, and as component C at least one, preferably exactly one safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly pyridine compound of formula (I), preferably of formula (1.16), especially preferred the compound (1.16.1-3), (1.16.1-4), (1 .16.1-10), (1.16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), or (1 .16.1-67), at least two, preferably exactly two herbicides B different from each other, and as component C at least one, preferably exactly one, safener C.
According to another preferred embodiment of the invention, the composition comprises as component A at least one, preferably exactly one pyridine compound of formula (I), preferably of formula (1 .16), especially preferred the compound (1.16.1-3), (1.16.1-4), (1 .16.1-10), (1 .16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), or (1 .16.1-67), at least three, preferably exactly three herbicides B different from each other, and as component C at least one, preferably exactly one, safener C. According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b1), in particular selected from the group consisting of clethodim, clodinafop- propargyl, cycloxydim, cyhalofop-butyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, metamifop, pi- noxaden, profoxydim, sethoxydim, tepraloxydim, tralkoxydim, esprocarb, ethofumesate, moli- nate, prosulfocarb, thiobencarb and triallate.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active com- pound from group b2), in particular selected from the group consisting of bensulfuron-methyl, bispyribac-sodium, cloransulam-methyl, chlorsulfuron, clorimuron, cyclosulfamuron, diclosulam, florasulam, flumetsulam, flupyrsulfuron-methyl-sodium, foramsulfuron, imazamox, imazamox- ammonium, imazapic, imazapic-ammonium, imazapic-isopropylammonium, imazapyr, ima- zapyr-ammonium, imazethapyr-isopropylammonium, imazaquin, imazaquin-ammonium, ima- zethapyr, imazethapyr-ammonium, imazethapyr-isopropylammonium, imazosulfuron, iodosulfu- ron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron-methyl, metazosulfuron, metsulfuron-methyl, metosulam, nicosulfuron, penoxsulam, propoxycarbazon-sodium, py- razosulfuron-ethyl, pyribenzoxim, pyriftalid, pyroxsulam, propyrisulfuron, rimsulfuron, sulfosulfu- ron, thiencarbazon-methyl, thifensulfuron-methyl, tribenuron-methyl, tritosulfuron and triafa- mone.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b3), in particular selected from the group consisting of ametryn, atrazine, bentazon, bromoxynil, bromoxynil-octanoate, bromoxynil-heptanoate, bromoxynil-potassium, diuron, fluometuron, hexazinone, isoproturon, linuron, metamitron, metribuzin, paraquat-dichlo- ride, propanil, simazin, terbutryn and terbuthylazine.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b4), in particular selected from the group consisting of acifluorfen, butafencil, carfenetrazone-ethyl, flumioxazin, fomesafen, oxadiargyl, oxyfluorfen, pyraflufen, pyraflufen- ethyl, saflufenacil, sulfentrazone, trifludimoxazin , ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-tri- fluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6; S-3100).
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b5), in particular selected from the group consisting of amitrole, benzobicy- clon, bicyclopyrone, clomazone, diflufenican, fenquintrone, fluometuron, flurochloridone, isoxaflutole, mesotrione, norflurazone, oxotrione (CAS 1486617-21-3), picolinafen, sulcotrione, tefuryltrione, tembotrione, tolpyralate, topramezone, topramezone-sodium and 2-chloro-3-me- thylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0) .
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b6), in particular selected from the group consisting of glyphosate, glypho- sate-ammonium, glyphosate-dimethylammonium , glyphosate-isopropylammonium and glypho- sate-trimesium (sulfosate) and glyphosate-potassium.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b7), in particular selected from the group consisting of glufosinate, glufosinate-ammonium, glufosinate-P and glufosinate-P-ammonium.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b9), in particular selected from the group consisting of pendimethalin and tri- fluralin.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of acetochlor, butachlor, cafenstrole, dimethenamid-P, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, S- metolachlor, fenoxasulfone, ipfencarbazone and pyroxasulfone. Likewise, preference is given to compositions comprising in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11 ), (1.3.1-17), (1.3.1- 18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1- 52), (1.3.1-53), (1.3.1-59), (1 .3.1-60), (1.3.1-66), (1 .3.1-67), (1 .15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-1 1 ), (1.15.1-17), (1.15.1-18), (1.15.1-24), (1.15.1-25), (1.15.1-31 ), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1-46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1 .16.1-4), (1.16.1-10), (1.16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b10), in particular selected from the group consisting of isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9, as defined above.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1 .3.1-1 1 ), (1.3.1-17), (1.3.1-18), (1 .3.1-24), (1.3.1-25), (1.3.1-31 ), (1 .3.1-32), (1.3.1-38), (1 .3.1-39), (1.3.1-45), (1 .3.1-46), (1.3.1-52), (1 .3.1-53), (1.3.1-59), (1.3.1-60), (1 .3.1-66), (1.3.1-67), (1 .15.1-3), (1.15.1-4), (1 .15.1-10), (1 .15.1-1 1 ), (1 .15.1-17), (1 .15.1- 18), (1.15.1-24), (1 .15.1-25), (1 .15.1-31 ), (1 .15.1-32), (1 .15.1-38), (1.15.1-39), (1 .15.1-45), (1 .15.1- 46), (1.15.1-52), (1 .15.1-53), (1 .15.1-59), (1 .15.1-60), (1 .15.1-66), (1.15.1-67), (1 .16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active com- pound from group b1 1 ), in particular indaziflam, isoxaben and triaziflam.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1 .3.1-1 1 ), (1.3.1-17), (1.3.1-18), (1 .3.1-24), (1.3.1-25), (1.3.1-31 ), (1 .3.1-32), (1.3.1-38), (1 .3.1-39), (1.3.1-45), (1 .3.1-46), (1.3.1-52), (1 .3.1-53), (1.3.1-59), (1.3.1-60), (1 .3.1-66), (1.3.1-67), (1 .15.1-3), (1.15.1-4), (1 .15.1-10), (1 .15.1-1 1 ), (1 .15.1-17), (1 .15.1- 18), (1.15.1-24), (1 .15.1-25), (1 .15.1-31 ), (1 .15.1-32), (1 .15.1-38), (1.15.1-39), (1 .15.1-45), (1 .15.1- 46), (1.15.1-52), (1 .15.1-53), (1 .15.1-59), (1 .15.1-60), (1 .15.1-66), (1.15.1-67), (1 .16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-1 1 ), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31 ), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b13), in particular selected from the group consisting of 2,4-D, 2,4-D-isobutyl, 2,4-D-dimethylammonium, 2,4-D-N,N,N-trimethylethanolammonium, aminocyclopyrachlor, ami- nocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, aminopyralid-methyl, aminopyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium, clopyralid, clopyralid-methyl, clopyralid-olamine, dicamba, dicamba-butotyl, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium, dicamba-po- tassium, dicamba-sodium, dicamba-trolamine, dicamba-N,N-bis-(3-aminopropyl)methylamine, dicamba-diethylenetriamine, flopyrauxifen, fluroxypyr, fluroxypyr-meptyl, halauxifen, halauxifen- methyl, MCPA, MCPA-2-ethylhexyl, MCPA-dimethylammonium, quinclorac, quinclorac-dime- thylammonium, quinmerac, quinmerac-dimethylammonium, florpyrauxifen , florpyrauxifen-ben- zyl (CAS 1390661 -72-9), and 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1 H-indol-6-yl)picolinic acid (CAS 1629965-65-6) .
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b14), in particular selected from the group consisting of diflufenzopyr, diflufenzopyr-sodium, dymron, indanofan and diflufenzopyr-sodium.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one herbicidally active compound from group b15), in particular selected from the group consisting of cinmethylin, dymron (= daimuron), indanofan and oxaziclomefone.
According to another preferred embodiment of the invention, the composition comprises, in addition to a pyridine compounds of formula (I), especially an active compound from the group consisting of (1.3.1-3), (1.3.1-4), (1.3.1-10), (1.3.1-11), (1.3.1-17), (1.3.1-18), (1.3.1-24), (1.3.1-25), (1.3.1-31), (1.3.1-32), (1.3.1-38), (1.3.1-39), (1.3.1-45), (1.3.1-46), (1.3.1-52), (1.3.1-53), (1.3.1-59), (1.3.1-60), (1.3.1-66), (1.3.1-67), (1.15.1-3), (1.15.1-4), (1.15.1-10), (1.15.1-11), (1.15.1-17), (1.15.1- 18), (1.15.1-24), (1.15.1-25), (1.15.1-31), (1.15.1-32), (1.15.1-38), (1.15.1-39), (1.15.1-45), (1.15.1- 46), (1.15.1-52), (1.15.1-53), (1.15.1-59), (1.15.1-60), (1.15.1-66), (1.15.1-67), (1.16.1-3), (1.16.1-4), (1.16.1-10), (1.16.1-11), (1.16.1-17), (1.16.1-18), (1.16.1-24), (1.16.1-25), (1.16.1-31), (1.16.1-32), (1.16.1-38), (1.16.1-39), (1.16.1-45), (1.16.1-46), (1.16.1-52), (1.16.1-53), (1.16.1-59), (1.16.1-60), (1.16.1-66), and (1.16.1-67), at least one and especially exactly one safener C, in particular selected from the group consisting of benoxacor, cloquintocet, cyprosulfamide, dichlormid, fenchlorazole, fenclorim, furilazole, isoxadifen, mefenpyr, 4-(dichloroacetyl)-1-oxa-4- azaspiro[4.5]decane (MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3-(dichloroacetyl)-1,3- oxazolidine (R-29148, CAS 52836-31-4).
Here and below, the term "binary compositions" includes compositions comprising one or more, e.g.1 , 2 or 3, active compounds of the formula (I) and either one or more, e.g.1 , 2 or 3, herbicides B or one or more safeners C.
Correspondingly, the term "ternary compositions" includes compositions comprising one or more, e.g.1 , 2 or 3, active compounds of the formula (I), one or more, e.g.1 , 2 or 3, herbicides B and one or more, e.g.1 , 2 or 3, safeners C.
In binary compositions comprising at least one pyridine compound of formula (I) as component A and at least one herbicide B, the weight ratio of the active compounds A:B is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 .
In binary compositions comprising at least one pyridine compound of formula (I) as component A and at least one safener C, the weight ratio of the active compounds A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 .
In ternary compositions comprising at least one pyridine compound of formula (I) as component A, at least one herbicide B and at least one safener C, the relative proportions by weight of the components A:B are generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , the weight ratio of the components A:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 , and the weight ratio of the components B:C is generally in the range of from 1 :1000 to 1000:1 , preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 . The weight ratio of components A + B to component C is preferably in the range of from 1 :500 to 500:1 , in particular in the range of from 1 :250 to 250:1 and particularly preferably in the range of from 1 :75 to 75:1 .
The weight ratios of the individual components in the preferred mixtures mentioned below are within the limits given above, in particular within the preferred limits.
Particularly preferred are the compositions mentioned below comprising the pyridine compounds of formula I as defined and the substance(s) as defined in the respective row of table T; especially preferred comprising as only herbicidal active compounds the pyridine compounds of formula I as defined and the substance(s) as defined in the respective row of table T;
most preferably comprising as only active compounds the pyridine compounds of formula I as defined and the substance(s) as defined in the respective row of table T.
Particularly preferred are compositions 1 .1 to 1.3653, comprising the compound (1.3.1-3) and the substance(s) as defined in the respective row of table T:
Table T (compositions 1.1 to 1.3653):
comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.1 B.1 — 1.12 B.12 — 1 .23 B.23 —
1.2 B.2 — 1.13 B.13 — 1 .24 B.24 —
1.3 B.3 — 1.14 B.14 — 1 .25 B.25 —
1.4 B.4 — 1.15 B.15 — 1 .26 B.26 —
1.5 B.5 — 1.16 B.16 — 1 .27 B.27 —
1.6 B.6 — 1.17 B.17 — 1 .28 B.28 —
1.7 B.7 — 1.18 B.18 — 1 .29 B.29 —
1.8 B.8 — 1.19 B.19 — 1 .30 B.30 —
1.9 B.9 — 1.20 B.20 — 1 .31 B.31 —
1.10 B.10 — 1.21 B.21 — 1 .32 B.32 —
1.1 1 B.1 1 — 1.22 B.22 — 1 .33 B.33 — comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.34 B.34 — 1.75 B.75 — 1.116 B.116 —
1.35 B.35 — 1.76 B.76 — 1.117 B.117 —
1.36 B.36 — 1.77 B.77 — 1.118 B.118 —
1.37 B.37 — 1.78 B.78 — 1.119 B.119 —
1.38 B.38 — 1.79 B.79 — 1.120 B.120 —
1.39 B.39 — 1.80 B.80 — 1.121 B.121 —
1.40 B.40 — 1.81 B.81 — 1.122 B.122 —
1.41 B.41 — 1.82 B.82 — 1.123 B.123 —
1.42 B.42 — 1.83 B.83 — 1.124 B.124 —
1.43 B.43 — 1.84 B.84 — 1.125 B.125 —
1.44 B.44 — 1.85 B.85 — 1.126 B.126 —
1.45 B.45 — 1.86 B.86 — 1.127 B.127 —
1.46 B.46 — 1.87 B.87 — 1.128 B.128 —
1.47 B.47 — 1.88 B.88 — 1.129 B.129 —
1.48 B.48 — 1.89 B.89 — 1.130 B.130 —
1.49 B.49 — 1.90 B.90 — 1.131 B.131 —
1.50 B.50 — 1.91 B.91 — 1.132 B.132 —
1.51 B.51 — 1.92 B.92 — 1.133 B.133 —
1.52 B.52 — 1.93 B.93 — 1.134 B.134 —
1.53 B.53 — 1.94 B.94 — 1.135 B.135 —
1.54 B.54 — 1.95 B.95 — 1.136 B.136 —
1.55 B.55 — 1.96 B.96 — 1.137 B.137 —
1.56 B.56 — 1.97 B.97 — 1.138 B.138 —
1.57 B.57 — 1.98 B.98 — 1.139 B.139 —
1.58 B.58 — 1.99 B.99 — 1.140 B.140 —
1.59 B.59 — 1.100 B.100 — 1.141 B.141 —
1.60 B.60 — 1.101 B.101 — 1.142 B.142 —
1.61 B.61 — 1.102 B.102 — 1.143 B.143 —
1.62 B.62 — 1.103 B.103 — 1.144 B.144 —
1.63 B.63 — 1.104 B.104 — 1.145 B.145 —
1.64 B.64 — 1.105 B.105 — 1.146 B.146 —
1.65 B.65 — 1.106 B.106 — 1.147 B.147 —
1.66 B.66 — 1.107 B.107 — 1.148 B.148 —
1.67 B.67 — 1.108 B.108 — 1.149 B.149 —
1.68 B.68 — 1.109 B.109 — 1.150 B.150 —
1.69 B.69 — 1.110 B.110 — 1.151 B.151 —
1.70 B.70 — 1.111 B.111 — 1.152 B.152 —
1.71 B.71 — 1.112 B.112 — 1.153 B.153 —
1.72 B.72 — 1.113 B.113 — 1.154 B.154 —
1.73 B.73 — 1.114 B.114 — 1.155 B.155 —
1.74 B.74 — 1.115 B.115 — 1.156 B.156 — comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.157 B.157 — 1.198 B.198 — 1.239 B.37 C.1
1.158 B.158 — 1.199 B.199 — 1.240 B.38 C.1
1.159 B.159 — 1.200 B.200 — 1.241 B.39 C.1
1.160 B.160 — 1.201 B.201 — 1.242 B.40 C.1
1.161 B.161 — 1.202 B.202 — 1.243 B.41 C.1
1.162 B.162 — 1.203 B.1 C.1 1.244 B.42 C.1
1.163 B.163 — 1.204 B.2 C.1 1.245 B.43 C.1
1.164 B.164 — 1.205 B.3 C.1 1.246 B.44 C.1
1.165 B.165 — 1.206 B.4 C.1 1.247 B.45 C.1
1.166 B.166 — 1.207 B.5 C.1 1.248 B.46 C.1
1.167 B.167 — 1.208 B.6 C.1 1.249 B.47 C.1
1.168 B.168 — 1.209 B.7 C.1 1.250 B.48 C.1
1.169 B.169 — 1.210 B.8 C.1 1.251 B.49 C.1
1.170 B.170 — 1.211 B.9 C.1 1.252 B.50 C.1
1.171 B.171 — 1.212 B.10 C.1 1.253 B.51 C.1
1.172 B.172 — 1.213 B.11 C.1 1.254 B.52 C.1
1.173 B.173 — 1.214 B.12 C.1 1.255 B.53 C.1
1.174 B.174 — 1.215 B.13 C.1 1.256 B.54 C.1
1.175 B.175 — 1.216 B.14 C.1 1.257 B.55 C.1
1.176 B.176 — 1.217 B.15 C.1 1.258 B.56 C.1
1.177 B.177 — 1.218 B.16 C.1 1.259 B.57 C.1
1.178 B.178 — 1.219 B.17 C.1 1.260 B.58 C.1
1.179 B.179 — 1.220 B.18 C.1 1.261 B.59 C.1
1.180 B.180 — 1.221 B.19 C.1 1.262 B.60 C.1
1.181 B.181 — 1.222 B.20 C.1 1.263 B.61 C.1
1.182 B.182 — 1.223 B.21 C.1 1.264 B.62 C.1
1.183 B.183 — 1.224 B.22 C.1 1.265 B.63 C.1
1.184 B.184 — 1.225 B.23 C.1 1.266 B.64 C.1
1.185 B.185 — 1.226 B.24 C.1 1.267 B.65 C.1
1.186 B.186 — 1.227 B.25 C.1 1.268 B.66 C.1
1.187 B.187 — 1.228 B.26 C.1 1.269 B.67 C.1
1.188 B.188 — 1.229 B.27 C.1 1.270 B.68 C.1
1.189 B.189 — 1.230 B.28 C.1 1.271 B.69 C.1
1.190 B.190 — 1.231 B.29 C.1 1.272 B.70 C.1
1.191 B.191 — 1.232 B.30 C.1 1.273 B.71 C.1
1.192 B.192 — 1.233 B.31 C.1 1.274 B.72 C.1
1.193 B.193 — 1.234 B.32 C.1 1.275 B.73 C.1
1.194 B.194 — 1.235 B.33 C.1 1.276 B.74 C.1
1.195 B.195 — 1.236 B.34 C.1 1.277 B.75 C.1
1.196 B.196 — 1.237 B.35 C.1 1.278 B.76 C.1
1.197 B.197 — 1.238 B.36 C.1 1.279 B.77 C.1 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.280 B.78 C.1 1.321 B.119 C.1 1.362 B.160 C.1
1.281 B.79 C.1 1.322 B.120 C.1 1.363 B.161 C.1
1.282 B.80 C.1 1.323 B.121 C.1 1.364 B.162 C.1
1.283 B.81 C.1 1.324 B.122 C.1 1.365 B.163 C.1
1.284 B.82 C.1 1.325 B.123 C.1 1.366 B.164 C.1
1.285 B.83 C.1 1.326 B.124 C.1 1.367 B.165 C.1
1.286 B.84 C.1 1.327 B.125 C.1 1.368 B.166 C.1
1.287 B.85 C.1 1.328 B.126 C.1 1.369 B.167 C.1
1.288 B.86 C.1 1.329 B.127 C.1 1.370 B.168 C.1
1.289 B.87 C.1 1.330 B.128 C.1 1.371 B.169 C.1
1.290 B.88 C.1 1.331 B.129 C.1 1.372 B.170 C.1
1.291 B.89 C.1 1.332 B.130 C.1 1.373 B.171 C.1
1.292 B.90 C.1 1.333 B.131 C.1 1.374 B.172 C.1
1.293 B.91 C.1 1.334 B.132 C.1 1.375 B.173 C.1
1.294 B.92 C.1 1.335 B.133 C.1 1.376 B.174 C.1
1.295 B.93 C.1 1.336 B.134 C.1 1.377 B.175 C.1
1.296 B.94 C.1 1.337 B.135 C.1 1.378 B.176 C.1
1.297 B.95 C.1 1.338 B.136 C.1 1.379 B.177 C.1
1.298 B.96 C.1 1.339 B.137 C.1 1.380 B.178 C.1
1.299 B.97 C.1 1.340 B.138 C.1 1.381 B.179 C.1
1.300 B.98 C.1 1.341 B.139 C.1 1.382 B.180 C.1
1.301 B.99 C.1 1.342 B.140 C.1 1.383 B.181 C.1
1.302 B.100 C.1 1.343 B.141 C.1 1.384 B.182 C.1
1.303 B.101 C.1 1.344 B.142 C.1 1.385 B.183 C.1
1.304 B.102 C.1 1.345 B.143 C.1 1.386 B.184 C.1
1.305 B.103 C.1 1.346 B.144 C.1 1.387 B.185 C.1
1.306 B.104 C.1 1.347 B.145 C.1 1.388 B.186 C.1
1.307 B.105 C.1 1.348 B.146 C.1 1.389 B.187 C.1
1.308 B.106 C.1 1.349 B.147 C.1 1.390 B.188 C.1
1.309 B.107 C.1 1.350 B.148 C.1 1.391 B.189 C.1
1.310 B.108 C.1 1.351 B.149 C.1 1.392 B.190 C.1
1.311 B.109 C.1 1.352 B.150 C.1 1.393 B.191 C.1
1.312 B.110 C.1 1.353 B.151 C.1 1.394 B.192 C.1
1.313 B.111 C.1 1.354 B.152 C.1 1.395 B.193 C.1
1.314 B.112 C.1 1.355 B.153 C.1 1.396 B.194 C.1
1.315 B.113 C.1 1.356 B.154 C.1 1.397 B.195 C.1
1.316 B.114 C.1 1.357 B.155 C.1 1.398 B.196 C.1
1.317 B.115 C.1 1.358 B.156 C.1 1.399 B.197 C.1
1.318 B.116 C.1 1.359 B.157 C.1 1.400 B.198 C.1
1.319 B.117 C.1 1.360 B.158 C.1 1.401 B.199 C.1
1.320 B.118 C.1 1.361 B.159 C.1 1.402 B.200 C.1 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.403 B.201 C.1 1.444 B.40 C.2 1.485 B.81 C.2
1.404 B.202 C.1 1.445 B.41 C.2 1.486 B.82 C.2
1.405 B.1 C.2 1.446 B.42 C.2 1.487 B.83 C.2
1.406 B.2 C.2 1.447 B.43 C.2 1.488 B.84 C.2
1.407 B.3 C.2 1.448 B.44 C.2 1.489 B.85 C.2
1.408 B.4 C.2 1.449 B.45 C.2 1.490 B.86 C.2
1.409 B.5 C.2 1.450 B.46 C.2 1.491 B.87 C.2
1.410 B.6 C.2 1.451 B.47 C.2 1.492 B.88 C.2
1.411 B.7 C.2 1.452 B.48 C.2 1.493 B.89 C.2
1.412 B.8 C.2 1.453 B.49 C.2 1.494 B.90 C.2
1.413 B.9 C.2 1.454 B.50 C.2 1.495 B.91 C.2
1.414 B.10 C.2 1.455 B.51 C.2 1.496 B.92 C.2
1.415 B.11 C.2 1.456 B.52 C.2 1.497 B.93 C.2
1.416 B.12 C.2 1.457 B.53 C.2 1.498 B.94 C.2
1.417 B.13 C.2 1.458 B.54 C.2 1.499 B.95 C.2
1.418 B.14 C.2 1.459 B.55 C.2 1.500 B.96 C.2
1.419 B.15 C.2 1.460 B.56 C.2 1.501 B.97 C.2
1.420 B.16 C.2 1.461 B.57 C.2 1.502 B.98 C.2
1.421 B.17 C.2 1.462 B.58 C.2 1.503 B.99 C.2
1.422 B.18 C.2 1.463 B.59 C.2 1.504 B.100 C.2
1.423 B.19 C.2 1.464 B.60 C.2 1.505 B.101 C.2
1.424 B.20 C.2 1.465 B.61 C.2 1.506 B.102 C.2
1.425 B.21 C.2 1.466 B.62 C.2 1.507 B.103 C.2
1.426 B.22 C.2 1.467 B.63 C.2 1.508 B.104 C.2
1.427 B.23 C.2 1.468 B.64 C.2 1.509 B.105 C.2
1.428 B.24 C.2 1.469 B.65 C.2 1.510 B.106 C.2
1.429 B.25 C.2 1.470 B.66 C.2 1.511 B.107 C.2
1.430 B.26 C.2 1.471 B.67 C.2 1.512 B.108 C.2
1.431 B.27 C.2 1.472 B.68 C.2 1.513 B.109 C.2
1.432 B.28 C.2 1.473 B.69 C.2 1.514 B.110 C.2
1.433 B.29 C.2 1.474 B.70 C.2 1.515 B.111 C.2
1.434 B.30 C.2 1.475 B.71 C.2 1.516 B.112 C.2
1.435 B.31 C.2 1.476 B.72 C.2 1.517 B.113 C.2
1.436 B.32 C.2 1.477 B.73 C.2 1.518 B.114 C.2
1.437 B.33 C.2 1.478 B.74 C.2 1.519 B.115 C.2
1.438 B.34 C.2 1.479 B.75 C.2 1.520 B.116 C.2
1.439 B.35 C.2 1.480 B.76 C.2 1.521 B.117 C.2
1.440 B.36 C.2 1.481 B.77 C.2 1.522 B.118 C.2
1.441 B.37 C.2 1.482 B.78 C.2 1.523 B.119 C.2
1.442 B.38 C.2 1.483 B.79 C.2 1.524 B.120 C.2
1.443 B.39 C.2 1.484 B.80 C.2 1.525 B.121 C.2 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.526 B.122 C.2 1.567 B.163 C.2 1.608 B.2 C.3
1.527 B.123 C.2 1.568 B.164 C.2 1.609 B.3 C.3
1.528 B.124 C.2 1.569 B.165 C.2 1.610 B.4 C.3
1.529 B.125 C.2 1.570 B.166 C.2 1.611 B.5 C.3
1.530 B.126 C.2 1.571 B.167 C.2 1.612 B.6 C.3
1.531 B.127 C.2 1.572 B.168 C.2 1.613 B.7 C.3
1.532 B.128 C.2 1.573 B.169 C.2 1.614 B.8 C.3
1.533 B.129 C.2 1.574 B.170 C.2 1.615 B.9 C.3
1.534 B.130 C.2 1.575 B.171 C.2 1.616 B.10 C.3
1.535 B.131 C.2 1.576 B.172 C.2 1.617 B.11 C.3
1.536 B.132 C.2 1.577 B.173 C.2 1.618 B.12 C.3
1.537 B.133 C.2 1.578 B.174 C.2 1.619 B.13 C.3
1.538 B.134 C.2 1.579 B.175 C.2 1.620 B.14 C.3
1.539 B.135 C.2 1.580 B.176 C.2 1.621 B.15 C.3
1.540 B.136 C.2 1.581 B.177 C.2 1.622 B.16 C.3
1.541 B.137 C.2 1.582 B.178 C.2 1.623 B.17 C.3
1.542 B.138 C.2 1.583 B.179 C.2 1.624 B.18 C.3
1.543 B.139 C.2 1.584 B.180 C.2 1.625 B.19 C.3
1.544 B.140 C.2 1.585 B.181 C.2 1.626 B.20 C.3
1.545 B.141 C.2 1.586 B.182 C.2 1.627 B.21 C.3
1.546 B.142 C.2 1.587 B.183 C.2 1.628 B.22 C.3
1.547 B.143 C.2 1.588 B.184 C.2 1.629 B.23 C.3
1.548 B.144 C.2 1.589 B.185 C.2 1.630 B.24 C.3
1.549 B.145 C.2 1.590 B.186 C.2 1.631 B.25 C.3
1.550 B.146 C.2 1.591 B.187 C.2 1.632 B.26 C.3
1.551 B.147 C.2 1.592 B.188 C.2 1.633 B.27 C.3
1.552 B.148 C.2 1.593 B.189 C.2 1.634 B.28 C.3
1.553 B.149 C.2 1.594 B.190 C.2 1.635 B.29 C.3
1.554 B.150 C.2 1.595 B.191 C.2 1.636 B.30 C.3
1.555 B.151 C.2 1.596 B.192 C.2 1.637 B.31 C.3
1.556 B.152 C.2 1.597 B.193 C.2 1.638 B.32 C.3
1.557 B.153 C.2 1.598 B.194 C.2 1.639 B.33 C.3
1.558 B.154 C.2 1.599 B.195 C.2 1.640 B.34 C.3
1.559 B.155 C.2 1.600 B.196 C.2 1.641 B.35 C.3
1.560 B.156 C.2 1.601 B.197 C.2 1.642 B.36 C.3
1.561 B.157 C.2 1.602 B.198 C.2 1.643 B.37 C.3
1.562 B.158 C.2 1.603 B.199 C.2 1.644 B.38 C.3
1.563 B.159 C.2 1.604 B.200 C.2 1.645 B.39 C.3
1.564 B.160 C.2 1.605 B.201 C.2 1.646 B.40 C.3
1.565 B.161 C.2 1.606 B.202 C.2 1.647 B.41 C.3
1.566 B.162 C.2 1.607 B.1 C.3 1.648 B.42 C.3 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.649 B.43 C.3 1.690 B.84 C.3 1.731 B.125 C.3
1.650 B.44 C.3 1.691 B.85 C.3 1.732 B.126 C.3
1.651 B.45 C.3 1.692 B.86 C.3 1.733 B.127 C.3
1.652 B.46 C.3 1.693 B.87 C.3 1.734 B.128 C.3
1.653 B.47 C.3 1.694 B.88 C.3 1.735 B.129 C.3
1.654 B.48 C.3 1.695 B.89 C.3 1.736 B.130 C.3
1.655 B.49 C.3 1.696 B.90 C.3 1.737 B.131 C.3
1.656 B.50 C.3 1.697 B.91 C.3 1.738 B.132 C.3
1.657 B.51 C.3 1.698 B.92 C.3 1.739 B.133 C.3
1.658 B.52 C.3 1.699 B.93 C.3 1.740 B.134 C.3
1.659 B.53 C.3 1.700 B.94 C.3 1.741 B.135 C.3
1.660 B.54 C.3 1.701 B.95 C.3 1.742 B.136 C.3
1.661 B.55 C.3 1.702 B.96 C.3 1.743 B.137 C.3
1.662 B.56 C.3 1.703 B.97 C.3 1.744 B.138 C.3
1.663 B.57 C.3 1.704 B.98 C.3 1.745 B.139 C.3
1.664 B.58 C.3 1.705 B.99 C.3 1.746 B.140 C.3
1.665 B.59 C.3 1.706 B.100 C.3 1.747 B.141 C.3
1.666 B.60 C.3 1.707 B.101 C.3 1.748 B.142 C.3
1.667 B.61 C.3 1.708 B.102 C.3 1.749 B.143 C.3
1.668 B.62 C.3 1.709 B.103 C.3 1.750 B.144 C.3
1.669 B.63 C.3 1.710 B.104 C.3 1.751 B.145 C.3
1.670 B.64 C.3 1.711 B.105 C.3 1.752 B.146 C.3
1.671 B.65 C.3 1.712 B.106 C.3 1.753 B.147 C.3
1.672 B.66 C.3 1.713 B.107 C.3 1.754 B.148 C.3
1.673 B.67 C.3 1.714 B.108 C.3 1.755 B.149 C.3
1.674 B.68 C.3 1.715 B.109 C.3 1.756 B.150 C.3
1.675 B.69 C.3 1.716 B.110 C.3 1.757 B.151 C.3
1.676 B.70 C.3 1.717 B.111 C.3 1.758 B.152 C.3
1.677 B.71 C.3 1.718 B.112 C.3 1.759 B.153 C.3
1.678 B.72 C.3 1.719 B.113 C.3 1.760 B.154 C.3
1.679 B.73 C.3 1.720 B.114 C.3 1.761 B.155 C.3
1.680 B.74 C.3 1.721 B.115 C.3 1.762 B.156 C.3
1.681 B.75 C.3 1.722 B.116 C.3 1.763 B.157 C.3
1.682 B.76 C.3 1.723 B.117 C.3 1.764 B.158 C.3
1.683 B.77 C.3 1.724 B.118 C.3 1.765 B.159 C.3
1.684 B.78 C.3 1.725 B.119 C.3 1.766 B.160 C.3
1.685 B.79 C.3 1.726 B.120 C.3 1.767 B.161 C.3
1.686 B.80 C.3 1.727 B.121 C.3 1.768 B.162 C.3
1.687 B.81 C.3 1.728 B.122 C.3 1.769 B.163 C.3
1.688 B.82 C.3 1.729 B.123 C.3 1.770 B.164 C.3
1.689 B.83 C.3 1.730 B.124 C.3 1.771 B.165 C.3 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.772 B.166 C.3 1.813 B.5 C.4 1.854 B.46 C.4
1.773 B.167 C.3 1.814 B.6 C.4 1.855 B.47 C.4
1.774 B.168 C.3 1.815 B.7 C.4 1.856 B.48 C.4
1.775 B.169 C.3 1.816 B.8 C.4 1.857 B.49 C.4
1.776 B.170 C.3 1.817 B.9 C.4 1.858 B.50 C.4
1.777 B.171 C.3 1.818 B.10 C.4 1.859 B.51 C.4
1.778 B.172 C.3 1.819 B.11 C.4 1.860 B.52 C.4
1.779 B.173 C.3 1.820 B.12 C.4 1.861 B.53 C.4
1.780 B.174 C.3 1.821 B.13 C.4 1.862 B.54 C.4
1.781 B.175 C.3 1.822 B.14 C.4 1.863 B.55 C.4
1.782 B.176 C.3 1.823 B.15 C.4 1.864 B.56 C.4
1.783 B.177 C.3 1.824 B.16 C.4 1.865 B.57 C.4
1.784 B.178 C.3 1.825 B.17 C.4 1.866 B.58 C.4
1.785 B.179 C.3 1.826 B.18 C.4 1.867 B.59 C.4
1.786 B.180 C.3 1.827 B.19 C.4 1.868 B.60 C.4
1.787 B.181 C.3 1.828 B.20 C.4 1.869 B.61 C.4
1.788 B.182 C.3 1.829 B.21 C.4 1.870 B.62 C.4
1.789 B.183 C.3 1.830 B.22 C.4 1.871 B.63 C.4
1.790 B.184 C.3 1.831 B.23 C.4 1.872 B.64 C.4
1.791 B.185 C.3 1.832 B.24 C.4 1.873 B.65 C.4
1.792 B.186 C.3 1.833 B.25 C.4 1.874 B.66 C.4
1.793 B.187 C.3 1.834 B.26 C.4 1.875 B.67 C.4
1.794 B.188 C.3 1.835 B.27 C.4 1.876 B.68 C.4
1.795 B.189 C.3 1.836 B.28 C.4 1.877 B.69 C.4
1.796 B.190 C.3 1.837 B.29 C.4 1.878 B.70 C.4
1.797 B.191 C.3 1.838 B.30 C.4 1.879 B.71 C.4
1.798 B.192 C.3 1.839 B.31 C.4 1.880 B.72 C.4
1.799 B.193 C.3 1.840 B.32 C.4 1.881 B.73 C.4
1.800 B.194 C.3 1.841 B.33 C.4 1.882 B.74 C.4
1.801 B.195 C.3 1.842 B.34 C.4 1.883 B.75 C.4
1.802 B.196 C.3 1.843 B.35 C.4 1.884 B.76 C.4
1.803 B.197 C.3 1.844 B.36 C.4 1.885 B.77 C.4
1.804 B.198 C.3 1.845 B.37 C.4 1.886 B.78 C.4
1.805 B.199 C.3 1.846 B.38 C.4 1.887 B.79 C.4
1.806 B.200 C.3 1.847 B.39 C.4 1.888 B.80 C.4
1.807 B.201 C.3 1.848 B.40 C.4 1.889 B.81 C.4
1.808 B.202 C.3 1.849 B.41 C.4 1.890 B.82 C.4
1.809 B.1 C.4 1.850 B.42 C.4 1.891 B.83 C.4
1.810 B.2 C.4 1.851 B.43 C.4 1.892 B.84 C.4
1.811 B.3 C.4 1.852 B.44 C.4 1.893 B.85 C.4
1.812 B.4 C.4 1.853 B.45 C.4 1.894 B.86 C.4 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.895 B.87 C.4 1.936 B.128 C.4 1.977 B.169 C.4
1.896 B.88 C.4 1.937 B.129 C.4 1.978 B.170 C.4
1.897 B.89 C.4 1.938 B.130 C.4 1.979 B.171 C.4
1.898 B.90 C.4 1.939 B.131 C.4 1.980 B.172 C.4
1.899 B.91 C.4 1.940 B.132 C.4 1.981 B.173 C.4
1.900 B.92 C.4 1.941 B.133 C.4 1.982 B.174 C.4
1.901 B.93 C.4 1.942 B.134 C.4 1.983 B.175 C.4
1.902 B.94 C.4 1.943 B.135 C.4 1.984 B.176 C.4
1.903 B.95 C.4 1.944 B.136 C.4 1.985 B.177 C.4
1.904 B.96 C.4 1.945 B.137 C.4 1.986 B.178 C.4
1.905 B.97 C.4 1.946 B.138 C.4 1.987 B.179 C.4
1.906 B.98 C.4 1.947 B.139 C.4 1.988 B.180 C.4
1.907 B.99 C.4 1.948 B.140 C.4 1.989 B.181 C.4
1.908 B.100 C.4 1.949 B.141 C.4 1.990 B.182 C.4
1.909 B.101 C.4 1.950 B.142 C.4 1.991 B.183 C.4
1.910 B.102 C.4 1.951 B.143 C.4 1.992 B.184 C.4
1.911 B.103 C.4 1.952 B.144 C.4 1.993 B.185 C.4
1.912 B.104 C.4 1.953 B.145 C.4 1.994 B.186 C.4
1.913 B.105 C.4 1.954 B.146 C.4 1.995 B.187 C.4
1.914 B.106 C.4 1.955 B.147 C.4 1.996 B.188 C.4
1.915 B.107 C.4 1.956 B.148 C.4 1.997 B.189 C.4
1.916 B.108 C.4 1.957 B.149 C.4 1.998 B.190 C.4
1.917 B.109 C.4 1.958 B.150 C.4 1.999 B.191 C.4
1.918 B.110 C.4 1.959 B.151 C.4 1.1000 B.192 C.4
1.919 B.111 C.4 1.960 B.152 C.4 1.1001 B.193 C.4
1.920 B.112 C.4 1.961 B.153 C.4 1.1002 B.194 C.4
1.921 B.113 C.4 1.962 B.154 C.4 1.1003 B.195 C.4
1.922 B.114 C.4 1.963 B.155 C.4 1.1004 B.196 C.4
1.923 B.115 C.4 1.964 B.156 C.4 1.1005 B.197 C.4
1.924 B.116 C.4 1.965 B.157 C.4 1.1006 B.198 C.4
1.925 B.117 C.4 1.966 B.158 C.4 1.1007 B.199 C.4
1.926 B.118 C.4 1.967 B.159 C.4 1.1008 B.200 C.4
1.927 B.119 C.4 1.968 B.160 C.4 1.1009 B.201 C.4
1.928 B.120 C.4 1.969 B.161 C.4 1.1010 B.202 C.4
1.929 B.121 C.4 1.970 B.162 C.4 1.1011 B.1 C.5
1.930 B.122 C.4 1.971 B.163 C.4 1.1012 B.2 C.5
1.931 B.123 C.4 1.972 B.164 C.4 1.1013 B.3 C.5
1.932 B.124 C.4 1.973 B.165 C.4 1.1014 B.4 C.5
1.933 B.125 C.4 1.974 B.166 C.4 1.1015 B.5 C.5
1.934 B.126 C.4 1.975 B.167 C.4 1.1016 B.6 C.5
1.935 B.127 C.4 1.976 B.168 C.4 1.1017 B.7 C.5 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.1018 B.8 C.5 1.1059 B.49 C.5 1.1100 B.90 C.5
1.1019 B.9 C.5 1.1060 B.50 C.5 1.1101 B.91 C.5
1.1020 B.10 C.5 1.1061 B.51 C.5 1.1102 B.92 C.5
1.1021 B.11 C.5 1.1062 B.52 C.5 1.1103 B.93 C.5
1.1022 B.12 C.5 1.1063 B.53 C.5 1.1104 B.94 C.5
1.1023 B.13 C.5 1.1064 B.54 C.5 1.1105 B.95 C.5
1.1024 B.14 C.5 1.1065 B.55 C.5 1.1106 B.96 C.5
1.1025 B.15 C.5 1.1066 B.56 C.5 1.1107 B.97 C.5
1.1026 B.16 C.5 1.1067 B.57 C.5 1.1108 B.98 C.5
1.1027 B.17 C.5 1.1068 B.58 C.5 1.1109 B.99 C.5
1.1028 B.18 C.5 1.1069 B.59 C.5 1.1110 B.100 C.5
1.1029 B.19 C.5 1.1070 B.60 C.5 1.1111 B.101 C.5
1.1030 B.20 C.5 1.1071 B.61 C.5 1.1112 B.102 C.5
1.1031 B.21 C.5 1.1072 B.62 C.5 1.1113 B.103 C.5
1.1032 B.22 C.5 1.1073 B.63 C.5 1.1114 B.104 C.5
1.1033 B.23 C.5 1.1074 B.64 C.5 1.1115 B.105 C.5
1.1034 B.24 C.5 1.1075 B.65 C.5 1.1116 B.106 C.5
1.1035 B.25 C.5 1.1076 B.66 C.5 1.1117 B.107 C.5
1.1036 B.26 C.5 1.1077 B.67 C.5 1.1118 B.108 C.5
1.1037 B.27 C.5 1.1078 B.68 C.5 1.1119 B.109 C.5
1.1038 B.28 C.5 1.1079 B.69 C.5 1.1120 B.110 C.5
1.1039 B.29 C.5 1.1080 B.70 C.5 1.1121 B.111 C.5
1.1040 B.30 C.5 1.1081 B.71 C.5 1.1122 B.112 C.5
1.1041 B.31 C.5 1.1082 B.72 C.5 1.1123 B.113 C.5
1.1042 B.32 C.5 1.1083 B.73 C.5 1.1124 B.114 C.5
1.1043 B.33 C.5 1.1084 B.74 C.5 1.1125 B.115 C.5
1.1044 B.34 C.5 1.1085 B.75 C.5 1.1126 B.116 C.5
1.1045 B.35 C.5 1.1086 B.76 C.5 1.1127 B.117 C.5
1.1046 B.36 C.5 1.1087 B.77 C.5 1.1128 B.118 C.5
1.1047 B.37 C.5 1.1088 B.78 C.5 1.1129 B.119 C.5
1.1048 B.38 C.5 1.1089 B.79 C.5 1.1130 B.120 C.5
1.1049 B.39 C.5 1.1090 B.80 C.5 1.1131 B.121 C.5
1.1050 B.40 C.5 1.1091 B.81 C.5 1.1132 B.122 C.5
1.1051 B.41 C.5 1.1092 B.82 C.5 1.1133 B.123 C.5
1.1052 B.42 C.5 1.1093 B.83 C.5 1.1134 B.124 C.5
1.1053 B.43 C.5 1.1094 B.84 C.5 1.1135 B.125 C.5
1.1054 B.44 C.5 1.1095 B.85 C.5 1.1136 B.126 C.5
1.1055 B.45 C.5 1.1096 B.86 C.5 1.1137 B.127 C.5
1.1056 B.46 C.5 1.1097 B.87 C.5 1.1138 B.128 C.5
1.1057 B.47 C.5 1.1098 B.88 C.5 1.1139 B.129 C.5
1.1058 B.48 C.5 1.1099 B.89 C.5 1.1140 B.130 C.5 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.1141 B.131 C.5 1.1182 B.172 C.5 1.1223 B.11 C.6
1.1142 B.132 C.5 1.1183 B.173 C.5 1.1224 B.12 C.6
1.1143 B.133 C.5 1.1184 B.174 C.5 1.1225 B.13 C.6
1.1144 B.134 C.5 1.1185 B.175 C.5 1.1226 B.14 C.6
1.1145 B.135 C.5 1.1186 B.176 C.5 1.1227 B.15 C.6
1.1146 B.136 C.5 1.1187 B.177 C.5 1.1228 B.16 C.6
1.1147 B.137 C.5 1.1188 B.178 C.5 1.1229 B.17 C.6
1.1148 B.138 C.5 1.1189 B.179 C.5 1.1230 B.18 C.6
1.1149 B.139 C.5 1.1190 B.180 C.5 1.1231 B.19 C.6
1.1150 B.140 C.5 1.1191 B.181 C.5 1.1232 B.20 C.6
1.1151 B.141 C.5 1.1192 B.182 C.5 1.1233 B.21 C.6
1.1152 B.142 C.5 1.1193 B.183 C.5 1.1234 B.22 C.6
1.1153 B.143 C.5 1.1194 B.184 C.5 1.1235 B.23 C.6
1.1154 B.144 C.5 1.1195 B.185 C.5 1.1236 B.24 C.6
1.1155 B.145 C.5 1.1196 B.186 C.5 1.1237 B.25 C.6
1.1156 B.146 C.5 1.1197 B.187 C.5 1.1238 B.26 C.6
1.1157 B.147 C.5 1.1198 B.188 C.5 1.1239 B.27 C.6
1.1158 B.148 C.5 1.1199 B.189 C.5 1.1240 B.28 C.6
1.1159 B.149 C.5 1.1200 B.190 C.5 1.1241 B.29 C.6
1.1160 B.150 C.5 1.1201 B.191 C.5 1.1242 B.30 C.6
1.1161 B.151 C.5 1.1202 B.192 C.5 1.1243 B.31 C.6
1.1162 B.152 C.5 1.1203 B.193 C.5 1.1244 B.32 C.6
1.1163 B.153 C.5 1.1204 B.194 C.5 1.1245 B.33 C.6
1.1164 B.154 C.5 1.1205 B.195 C.5 1.1246 B.34 C.6
1.1165 B.155 C.5 1.1206 B.196 C.5 1.1247 B.35 C.6
1.1166 B.156 C.5 1.1207 B.197 C.5 1.1248 B.36 C.6
1.1167 B.157 C.5 1.1208 B.198 C.5 1.1249 B.37 C.6
1.1168 B.158 C.5 1.1209 B.199 C.5 1.1250 B.38 C.6
1.1169 B.159 C.5 1.1210 B.200 C.5 1.1251 B.39 C.6
1.1170 B.160 C.5 1.1211 B.201 C.5 1.1252 B.40 C.6
1.1171 B.161 C.5 1.1212 B.202 C.5 1.1253 B.41 C.6
1.1172 B.162 C.5 1.1213 B.1 C.6 1.1254 B.42 C.6
1.1173 B.163 C.5 1.1214 B.2 C.6 1.1255 B.43 C.6
1.1174 B.164 C.5 1.1215 B.3 C.6 1.1256 B.44 C.6
1.1175 B.165 C.5 1.1216 B.4 C.6 1.1257 B.45 C.6
1.1176 B.166 C.5 1.1217 B.5 C.6 1.1258 B.46 C.6
1.1177 B.167 C.5 1.1218 B.6 C.6 1.1259 B.47 C.6
1.1178 B.168 C.5 1.1219 B.7 C.6 1.1260 B.48 C.6
1.1179 B.169 C.5 1.1220 B.8 C.6 1.1261 B.49 C.6
1.1180 B.170 C.5 1.1221 B.9 C.6 1.1262 B.50 C.6
1.1181 B.171 C.5 1.1222 B.10 C.6 1.1263 B.51 C.6 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.1264 B.52 C.6 1.1305 B.93 C.6 1.1346 B.134 C.6
1.1265 B.53 C.6 1.1306 B.94 C.6 1.1347 B.135 C.6
1.1266 B.54 C.6 1.1307 B.95 C.6 1.1348 B.136 C.6
1.1267 B.55 C.6 1.1308 B.96 C.6 1.1349 B.137 C.6
1.1268 B.56 C.6 1.1309 B.97 C.6 1.1350 B.138 C.6
1.1269 B.57 C.6 1.1310 B.98 C.6 1.1351 B.139 C.6
1.1270 B.58 C.6 1.1311 B.99 C.6 1.1352 B.140 C.6
1.1271 B.59 C.6 1.1312 B.100 C.6 1.1353 B.141 C.6
1.1272 B.60 C.6 1.1313 B.101 C.6 1.1354 B.142 C.6
1.1273 B.61 C.6 1.1314 B.102 C.6 1.1355 B.143 C.6
1.1274 B.62 C.6 1.1315 B.103 C.6 1.1356 B.144 C.6
1.1275 B.63 C.6 1.1316 B.104 C.6 1.1357 B.145 C.6
1.1276 B.64 C.6 1.1317 B.105 C.6 1.1358 B.146 C.6
1.1277 B.65 C.6 1.1318 B.106 C.6 1.1359 B.147 C.6
1.1278 B.66 C.6 1.1319 B.107 C.6 1.1360 B.148 C.6
1.1279 B.67 C.6 1.1320 B.108 C.6 1.1361 B.149 C.6
1.1280 B.68 C.6 1.1321 B.109 C.6 1.1362 B.150 C.6
1.1281 B.69 C.6 1.1322 B.110 C.6 1.1363 B.151 C.6
1.1282 B.70 C.6 1.1323 B.111 C.6 1.1364 B.152 C.6
1.1283 B.71 C.6 1.1324 B.112 C.6 1.1365 B.153 C.6
1.1284 B.72 C.6 1.1325 B.113 C.6 1.1366 B.154 C.6
1.1285 B.73 C.6 1.1326 B.114 C.6 1.1367 B.155 C.6
1.1286 B.74 C.6 1.1327 B.115 C.6 1.1368 B.156 C.6
1.1287 B.75 C.6 1.1328 B.116 C.6 1.1369 B.157 C.6
1.1288 B.76 C.6 1.1329 B.117 C.6 1.1370 B.158 C.6
1.1289 B.77 C.6 1.1330 B.118 C.6 1.1371 B.159 C.6
1.1290 B.78 C.6 1.1331 B.119 C.6 1.1372 B.160 C.6
1.1291 B.79 C.6 1.1332 B.120 C.6 1.1373 B.161 C.6
1.1292 B.80 C.6 1.1333 B.121 C.6 1.1374 B.162 C.6
1.1293 B.81 C.6 1.1334 B.122 C.6 1.1375 B.163 C.6
1.1294 B.82 C.6 1.1335 B.123 C.6 1.1376 B.164 C.6
1.1295 B.83 C.6 1.1336 B.124 C.6 1.1377 B.165 C.6
1.1296 B.84 C.6 1.1337 B.125 C.6 1.1378 B.166 C.6
1.1297 B.85 C.6 1.1338 B.126 C.6 1.1379 B.167 C.6
1.1298 B.86 C.6 1.1339 B.127 C.6 1.1380 B.168 C.6
1.1299 B.87 C.6 1.1340 B.128 C.6 1.1381 B.169 C.6
1.1300 B.88 C.6 1.1341 B.129 C.6 1.1382 B.170 C.6
1.1301 B.89 C.6 1.1342 B.130 C.6 1.1383 B.171 C.6
1.1302 B.90 C.6 1.1343 B.131 C.6 1.1384 B.172 C.6
1.1303 B.91 C.6 1.1344 B.132 C.6 1.1385 B.173 C.6
1.1304 B.92 C.6 1.1345 B.133 C.6 1.1386 B.174 C.6 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.1387 B.175 C.6 1.1428 B.14 C.7 1.1469 B.55 C.7
1.1388 B.176 C.6 1.1429 B.15 C.7 1.1470 B.56 C.7
1.1389 B.177 C.6 1.1430 B.16 C.7 1.1471 B.57 C.7
1.1390 B.178 C.6 1.1431 B.17 C.7 1.1472 B.58 C.7
1.1391 B.179 C.6 1.1432 B.18 C.7 1.1473 B.59 C.7
1.1392 B.180 C.6 1.1433 B.19 C.7 1.1474 B.60 C.7
1.1393 B.181 C.6 1.1434 B.20 C.7 1.1475 B.61 C.7
1.1394 B.182 C.6 1.1435 B.21 C.7 1.1476 B.62 C.7
1.1395 B.183 C.6 1.1436 B.22 C.7 1.1477 B.63 C.7
1.1396 B.184 C.6 1.1437 B.23 C.7 1.1478 B.64 C.7
1.1397 B.185 C.6 1.1438 B.24 C.7 1.1479 B.65 C.7
1.1398 B.186 C.6 1.1439 B.25 C.7 1.1480 B.66 C.7
1.1399 B.187 C.6 1.1440 B.26 C.7 1.1481 B.67 C.7
1.1400 B.188 C.6 1.1441 B.27 C.7 1.1482 B.68 C.7
1.1401 B.189 C.6 1.1442 B.28 C.7 1.1483 B.69 C.7
1.1402 B.190 C.6 1.1443 B.29 C.7 1.1484 B.70 C.7
1.1403 B.191 C.6 1.1444 B.30 C.7 1.1485 B.71 C.7
1.1404 B.192 C.6 1.1445 B.31 C.7 1.1486 B.72 C.7
1.1405 B.193 C.6 1.1446 B.32 C.7 1.1487 B.73 C.7
1.1406 B.194 C.6 1.1447 B.33 C.7 1.1488 B.74 C.7
1.1407 B.195 C.6 1.1448 B.34 C.7 1.1489 B.75 C.7
1.1408 B.196 C.6 1.1449 B.35 C.7 1.1490 B.76 C.7
1.1409 B.197 C.6 1.1450 B.36 C.7 1.1491 B.77 C.7
1.1410 B.198 C.6 1.1451 B.37 C.7 1.1492 B.78 C.7
1.1411 B.199 C.6 1.1452 B.38 C.7 1.1493 B.79 C.7
1.1412 B.200 C.6 1.1453 B.39 C.7 1.1494 B.80 C.7
1.1413 B.201 C.6 1.1454 B.40 C.7 1.1495 B.81 C.7
1.1414 B.202 C.6 1.1455 B.41 C.7 1.1496 B.82 C.7
1.1415 B.1 C.7 1.1456 B.42 C.7 1.1497 B.83 C.7
1.1416 B.2 C.7 1.1457 B.43 C.7 1.1498 B.84 C.7
1.1417 B.3 C.7 1.1458 B.44 C.7 1.1499 B.85 C.7
1.1418 B.4 C.7 1.1459 B.45 C.7 1.1500 B.86 C.7
1.1419 B.5 C.7 1.1460 B.46 C.7 1.1501 B.87 C.7
1.1420 B.6 C.7 1.1461 B.47 C.7 1.1502 B.88 C.7
1.1421 B.7 C.7 1.1462 B.48 C.7 1.1503 B.89 C.7
1.1422 B.8 C.7 1.1463 B.49 C.7 1.1504 B.90 C.7
1.1423 B.9 C.7 1.1464 B.50 C.7 1.1505 B.91 C.7
1.1424 B.10 C.7 1.1465 B.51 C.7 1.1506 B.92 C.7
1.1425 B.11 C.7 1.1466 B.52 C.7 1.1507 B.93 C.7
1.1426 B.12 C.7 1.1467 B.53 C.7 1.1508 B.94 C.7
1.1427 B.13 C.7 1.1468 B.54 C.7 1.1509 B.95 C.7 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.1510 B.96 C.7 1.1551 B.137 C.7 1.1592 B.178 C.7
1.1511 B.97 C.7 1.1552 B.138 C.7 1.1593 B.179 C.7
1.1512 B.98 C.7 1.1553 B.139 C.7 1.1594 B.180 C.7
1.1513 B.99 C.7 1.1554 B.140 C.7 1.1595 B.181 C.7
1.1514 B.100 C.7 1.1555 B.141 C.7 1.1596 B.182 C.7
1.1515 B.101 C.7 1.1556 B.142 C.7 1.1597 B.183 C.7
1.1516 B.102 C.7 1.1557 B.143 C.7 1.1598 B.184 C.7
1.1517 B.103 C.7 1.1558 B.144 C.7 1.1599 B.185 C.7
1.1518 B.104 C.7 1.1559 B.145 C.7 1.1600 B.186 C.7
1.1519 B.105 C.7 1.1560 B.146 C.7 1.1601 B.187 C.7
1.1520 B.106 C.7 1.1561 B.147 C.7 1.1602 B.188 C.7
1.1521 B.107 C.7 1.1562 B.148 C.7 1.1603 B.189 C.7
1.1522 B.108 C.7 1.1563 B.149 C.7 1.1604 B.190 C.7
1.1523 B.109 C.7 1.1564 B.150 C.7 1.1605 B.191 C.7
1.1524 B.110 C.7 1.1565 B.151 C.7 1.1606 B.192 C.7
1.1525 B.111 C.7 1.1566 B.152 C.7 1.1607 B.193 C.7
1.1526 B.112 C.7 1.1567 B.153 C.7 1.1608 B.194 C.7
1.1527 B.113 C.7 1.1568 B.154 C.7 1.1609 B.195 C.7
1.1528 B.114 C.7 1.1569 B.155 C.7 1.1610 B.196 C.7
1.1529 B.115 C.7 1.1570 B.156 C.7 1.1611 B.197 C.7
1.1530 B.116 C.7 1.1571 B.157 C.7 1.1612 B.198 C.7
1.1531 B.117 C.7 1.1572 B.158 C.7 1.1613 B.199 C.7
1.1532 B.118 C.7 1.1573 B.159 C.7 1.1614 B.200 C.7
1.1533 B.119 C.7 1.1574 B.160 C.7 1.1615 B.201 C.7
1.1534 B.120 C.7 1.1575 B.161 C.7 1.1616 B.202 C.7
1.1535 B.121 C.7 1.1576 B.162 C.7 1.1617 B.1 C.8
1.1536 B.122 C.7 1.1577 B.163 C.7 1.1618 B.2 C.8
1.1537 B.123 C.7 1.1578 B.164 C.7 1.1619 B.3 C.8
1.1538 B.124 C.7 1.1579 B.165 C.7 1.1620 B.4 C.8
1.1539 B.125 C.7 1.1580 B.166 C.7 1.1621 B.5 C.8
1.1540 B.126 C.7 1.1581 B.167 C.7 1.1622 B.6 C.8
1.1541 B.127 C.7 1.1582 B.168 C.7 1.1623 B.7 C.8
1.1542 B.128 C.7 1.1583 B.169 C.7 1.1624 B.8 C.8
1.1543 B.129 C.7 1.1584 B.170 C.7 1.1625 B.9 C.8
1.1544 B.130 C.7 1.1585 B.171 C.7 1.1626 B.10 C.8
1.1545 B.131 C.7 1.1586 B.172 C.7 1.1627 B.11 C.8
1.1546 B.132 C.7 1.1587 B.173 C.7 1.1628 B.12 C.8
1.1547 B.133 C.7 1.1588 B.174 C.7 1.1629 B.13 C.8
1.1548 B.134 C.7 1.1589 B.175 C.7 1.1630 B.14 C.8
1.1549 B.135 C.7 1.1590 B.176 C.7 1.1631 B.15 C.8
1.1550 B.136 C.7 1.1591 B.177 C.7 1.1632 B.16 C.8 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.1633 B.17 C.8 1.1674 B.58 C.8 1.1715 B.99 C.8
1.1634 B.18 C.8 1.1675 B.59 C.8 1.1716 B.100 C.8
1.1635 B.19 C.8 1.1676 B.60 C.8 1.1717 B.101 C.8
1.1636 B.20 C.8 1.1677 B.61 C.8 1.1718 B.102 C.8
1.1637 B.21 C.8 1.1678 B.62 C.8 1.1719 B.103 C.8
1.1638 B.22 C.8 1.1679 B.63 C.8 1.1720 B.104 C.8
1.1639 B.23 C.8 1.1680 B.64 C.8 1.1721 B.105 C.8
1.1640 B.24 C.8 1.1681 B.65 C.8 1.1722 B.106 C.8
1.1641 B.25 C.8 1.1682 B.66 C.8 1.1723 B.107 C.8
1.1642 B.26 C.8 1.1683 B.67 C.8 1.1724 B.108 C.8
1.1643 B.27 C.8 1.1684 B.68 C.8 1.1725 B.109 C.8
1.1644 B.28 C.8 1.1685 B.69 C.8 1.1726 B.110 C.8
1.1645 B.29 C.8 1.1686 B.70 C.8 1.1727 B.111 C.8
1.1646 B.30 C.8 1.1687 B.71 C.8 1.1728 B.112 C.8
1.1647 B.31 C.8 1.1688 B.72 C.8 1.1729 B.113 C.8
1.1648 B.32 C.8 1.1689 B.73 C.8 1.1730 B.114 C.8
1.1649 B.33 C.8 1.1690 B.74 C.8 1.1731 B.115 C.8
1.1650 B.34 C.8 1.1691 B.75 C.8 1.1732 B.116 C.8
1.1651 B.35 C.8 1.1692 B.76 C.8 1.1733 B.117 C.8
1.1652 B.36 C.8 1.1693 B.77 C.8 1.1734 B.118 C.8
1.1653 B.37 C.8 1.1694 B.78 C.8 1.1735 B.119 C.8
1.1654 B.38 C.8 1.1695 B.79 C.8 1.1736 B.120 C.8
1.1655 B.39 C.8 1.1696 B.80 C.8 1.1737 B.121 C.8
1.1656 B.40 C.8 1.1697 B.81 C.8 1.1738 B.122 C.8
1.1657 B.41 C.8 1.1698 B.82 C.8 1.1739 B.123 C.8
1.1658 B.42 C.8 1.1699 B.83 C.8 1.1740 B.124 C.8
1.1659 B.43 C.8 1.1700 B.84 C.8 1.1741 B.125 C.8
1.1660 B.44 C.8 1.1701 B.85 C.8 1.1742 B.126 C.8
1.1661 B.45 C.8 1.1702 B.86 C.8 1.1743 B.127 C.8
1.1662 B.46 C.8 1.1703 B.87 C.8 1.1744 B.128 C.8
1.1663 B.47 C.8 1.1704 B.88 C.8 1.1745 B.129 C.8
1.1664 B.48 C.8 1.1705 B.89 C.8 1.1746 B.130 C.8
1.1665 B.49 C.8 1.1706 B.90 C.8 1.1747 B.131 C.8
1.1666 B.50 C.8 1.1707 B.91 C.8 1.1748 B.132 C.8
1.1667 B.51 C.8 1.1708 B.92 C.8 1.1749 B.133 C.8
1.1668 B.52 C.8 1.1709 B.93 C.8 1.1750 B.134 C.8
1.1669 B.53 C.8 1.1710 B.94 C.8 1.1751 B.135 C.8
1.1670 B.54 C.8 1.1711 B.95 C.8 1.1752 B.136 C.8
1.1671 B.55 C.8 1.1712 B.96 C.8 1.1753 B.137 C.8
1.1672 B.56 C.8 1.1713 B.97 C.8 1.1754 B.138 C.8
1.1673 B.57 C.8 1.1714 B.98 C.8 1.1755 B.139 C.8 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.1756 B.140 C.8 1.1797 B.181 C.8 1 .1838 B.20 C.9
1.1757 B.141 C.8 1.1798 B.182 C.8 1 .1839 B.21 C.9
1.1758 B.142 C.8 1.1799 B.183 C.8 1 .1840 B.22 C.9
1.1759 B.143 C.8 1.1800 B.184 C.8 1 .1841 B.23 C.9
1.1760 B.144 C.8 1.1801 B.185 C.8 1 .1842 B.24 C.9
1.1761 B.145 C.8 1.1802 B.186 C.8 1 .1843 B.25 C.9
1.1762 B.146 C.8 1.1803 B.187 C.8 1 .1844 B.26 C.9
1.1763 B.147 C.8 1.1804 B.188 C.8 1 .1845 B.27 C.9
1.1764 B.148 C.8 1.1805 B.189 C.8 1 .1846 B.28 C.9
1.1765 B.149 C.8 1.1806 B.190 C.8 1 .1847 B.29 C.9
1.1766 B.150 C.8 1.1807 B.191 C.8 1 .1848 B.30 C.9
1.1767 B.151 C.8 1.1808 B.192 C.8 1 .1849 B.31 C.9
1.1768 B.152 C.8 1.1809 B.193 C.8 1 .1850 B.32 C.9
1.1769 B.153 C.8 1.1810 B.194 C.8 1 .1851 B.33 C.9
1.1770 B.154 C.8 1.181 1 B.195 C.8 1 .1852 B.34 C.9
1.1771 B.155 C.8 1.1812 B.196 C.8 1 .1853 B.35 C.9
1.1772 B.156 C.8 1.1813 B.197 C.8 1 .1854 B.36 C.9
1.1773 B.157 C.8 1.1814 B.198 C.8 1 .1855 B.37 C.9
1.1774 B.158 C.8 1.1815 B.199 C.8 1 .1856 B.38 C.9
1.1775 B.159 C.8 1.1816 B.200 C.8 1 .1857 B.39 C.9
1.1776 B.160 C.8 1.1817 B.201 C.8 1 .1858 B.40 C.9
1.1777 B.161 C.8 1.1818 B.202 C.8 1 .1859 B.41 C.9
1.1778 B.162 C.8 1.1819 B.1 C.9 1 .1860 B.42 C.9
1.1779 B.163 C.8 1.1820 B.2 C.9 1 .1861 B.43 C.9
1.1780 B.164 C.8 1.1821 B.3 C.9 1 .1862 B.44 C.9
1.1781 B.165 C.8 1.1822 B.4 C.9 1 .1863 B.45 C.9
1.1782 B.166 C.8 1.1823 B.5 C.9 1 .1864 B.46 C.9
1.1783 B.167 C.8 1.1824 B.6 C.9 1 .1865 B.47 C.9
1.1784 B.168 C.8 1.1825 B.7 C.9 1 .1866 B.48 C.9
1.1785 B.169 C.8 1.1826 B.8 C.9 1 .1867 B.49 C.9
1.1786 B.170 C.8 1.1827 B.9 C.9 1 .1868 B.50 C.9
1.1787 B.171 C.8 1.1828 B.10 C.9 1 .1869 B.51 C.9
1.1788 B.172 C.8 1.1829 B.1 1 C.9 1 .1870 B.52 C.9
1.1789 B.173 C.8 1.1830 B.12 C.9 1 .1871 B.53 C.9
1.1790 B.174 C.8 1.1831 B.13 C.9 1 .1872 B.54 C.9
1.1791 B.175 C.8 1.1832 B.14 C.9 1 .1873 B.55 C.9
1.1792 B.176 C.8 1.1833 B.15 C.9 1 .1874 B.56 C.9
1.1793 B.177 C.8 1.1834 B.16 C.9 1 .1875 B.57 C.9
1.1794 B.178 C.8 1.1835 B.17 C.9 1 .1876 B.58 C.9
1.1795 B.179 C.8 1.1836 B.18 C.9 1 .1877 B.59 C.9
1.1796 B.180 C.8 1.1837 B.19 C.9 1 .1878 B.60 C.9 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.1879 B.61 C.9 1.1920 B.102 C.9 1.1961 B.143 C.9
1.1880 B.62 C.9 1.1921 B.103 C.9 1.1962 B.144 C.9
1.1881 B.63 C.9 1.1922 B.104 C.9 1.1963 B.145 C.9
1.1882 B.64 C.9 1.1923 B.105 C.9 1.1964 B.146 C.9
1.1883 B.65 C.9 1.1924 B.106 C.9 1.1965 B.147 C.9
1.1884 B.66 C.9 1.1925 B.107 C.9 1.1966 B.148 C.9
1.1885 B.67 C.9 1.1926 B.108 C.9 1.1967 B.149 C.9
1.1886 B.68 C.9 1.1927 B.109 C.9 1.1968 B.150 C.9
1.1887 B.69 C.9 1.1928 B.110 C.9 1.1969 B.151 C.9
1.1888 B.70 C.9 1.1929 B.111 C.9 1.1970 B.152 C.9
1.1889 B.71 C.9 1.1930 B.112 C.9 1.1971 B.153 C.9
1.1890 B.72 C.9 1.1931 B.113 C.9 1.1972 B.154 C.9
1.1891 B.73 C.9 1.1932 B.114 C.9 1.1973 B.155 C.9
1.1892 B.74 C.9 1.1933 B.115 C.9 1.1974 B.156 C.9
1.1893 B.75 C.9 1.1934 B.116 C.9 1.1975 B.157 C.9
1.1894 B.76 C.9 1.1935 B.117 C.9 1.1976 B.158 C.9
1.1895 B.77 C.9 1.1936 B.118 C.9 1.1977 B.159 C.9
1.1896 B.78 C.9 1.1937 B.119 C.9 1.1978 B.160 C.9
1.1897 B.79 C.9 1.1938 B.120 C.9 1.1979 B.161 C.9
1.1898 B.80 C.9 1.1939 B.121 C.9 1.1980 B.162 C.9
1.1899 B.81 C.9 1.1940 B.122 C.9 1.1981 B.163 C.9
1.1900 B.82 C.9 1.1941 B.123 C.9 1.1982 B.164 C.9
1.1901 B.83 C.9 1.1942 B.124 C.9 1.1983 B.165 C.9
1.1902 B.84 C.9 1.1943 B.125 C.9 1.1984 B.166 C.9
1.1903 B.85 C.9 1.1944 B.126 C.9 1.1985 B.167 C.9
1.1904 B.86 C.9 1.1945 B.127 C.9 1.1986 B.168 C.9
1.1905 B.87 C.9 1.1946 B.128 C.9 1.1987 B.169 C.9
1.1906 B.88 C.9 1.1947 B.129 C.9 1.1988 B.170 C.9
1.1907 B.89 C.9 1.1948 B.130 C.9 1.1989 B.171 C.9
1.1908 B.90 C.9 1.1949 B.131 C.9 1.1990 B.172 C.9
1.1909 B.91 C.9 1.1950 B.132 C.9 1.1991 B.173 C.9
1.1910 B.92 C.9 1.1951 B.133 C.9 1.1992 B.174 C.9
1.1911 B.93 C.9 1.1952 B.134 C.9 1.1993 B.175 C.9
1.1912 B.94 C.9 1.1953 B.135 C.9 1.1994 B.176 C.9
1.1913 B.95 C.9 1.1954 B.136 C.9 1.1995 B.177 C.9
1.1914 B.96 C.9 1.1955 B.137 C.9 1.1996 B.178 C.9
1.1915 B.97 C.9 1.1956 B.138 C.9 1.1997 B.179 C.9
1.1916 B.98 C.9 1.1957 B.139 C.9 1.1998 B.180 C.9
1.1917 B.99 C.9 1.1958 B.140 C.9 1.1999 B.181 C.9
1.1918 B.100 C.9 1.1959 B.141 C.9 1.2000 B.182 C.9
1.1919 B.101 C.9 1.1960 B.142 C.9 1.2001 B.183 C.9 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.2002 B.184 C.9 1.2043 B.23 C.10 1.2084 B.64 C.10
1.2003 B.185 C.9 1.2044 B.24 C.10 1.2085 B.65 C.10
1.2004 B.186 C.9 1.2045 B.25 C.10 1.2086 B.66 C.10
1.2005 B.187 C.9 1.2046 B.26 C.10 1.2087 B.67 C.10
1.2006 B.188 C.9 1.2047 B.27 C.10 1.2088 B.68 C.10
1.2007 B.189 C.9 1.2048 B.28 C.10 1.2089 B.69 C.10
1.2008 B.190 C.9 1.2049 B.29 C.10 1.2090 B.70 C.10
1.2009 B.191 C.9 1.2050 B.30 C.10 1.2091 B.71 C.10
1.2010 B.192 C.9 1.2051 B.31 C.10 1.2092 B.72 C.10
1.2011 B.193 C.9 1.2052 B.32 C.10 1.2093 B.73 C.10
1.2012 B.194 C.9 1.2053 B.33 C.10 1.2094 B.74 C.10
1.2013 B.195 C.9 1.2054 B.34 C.10 1.2095 B.75 C.10
1.2014 B.196 C.9 1.2055 B.35 C.10 1.2096 B.76 C.10
1.2015 B.197 C.9 1.2056 B.36 C.10 1.2097 B.77 C.10
1.2016 B.198 C.9 1.2057 B.37 C.10 1.2098 B.78 C.10
1.2017 B.199 C.9 1.2058 B.38 C.10 1.2099 B.79 C.10
1.2018 B.200 C.9 1.2059 B.39 C.10 1.2100 B.80 C.10
1.2019 B.201 C.9 1.2060 B.40 C.10 1.2101 B.81 C.10
1.2020 B.202 C.9 1.2061 B.41 C.10 1.2102 B.82 C.10
1.2021 B.1 C.10 1.2062 B.42 C.10 1.2103 B.83 C.10
1.2022 B.2 C.10 1.2063 B.43 C.10 1.2104 B.84 C.10
1.2023 B.3 C.10 1.2064 B.44 C.10 1.2105 B.85 C.10
1.2024 B.4 C.10 1.2065 B.45 C.10 1.2106 B.86 C.10
1.2025 B.5 C.10 1.2066 B.46 C.10 1.2107 B.87 C.10
1.2026 B.6 C.10 1.2067 B.47 C.10 1.2108 B.88 C.10
1.2027 B.7 C.10 1.2068 B.48 C.10 1.2109 B.89 C.10
1.2028 B.8 C.10 1.2069 B.49 C.10 1.2110 B.90 C.10
1.2029 B.9 C.10 1.2070 B.50 C.10 1.2111 B.91 C.10
1.2030 B.10 C.10 1.2071 B.51 C.10 1.2112 B.92 C.10
1.2031 B.11 C.10 1.2072 B.52 C.10 1.2113 B.93 C.10
1.2032 B.12 C.10 1.2073 B.53 C.10 1.2114 B.94 C.10
1.2033 B.13 C.10 1.2074 B.54 C.10 1.2115 B.95 C.10
1.2034 B.14 C.10 1.2075 B.55 C.10 1.2116 B.96 C.10
1.2035 B.15 C.10 1.2076 B.56 C.10 1.2117 B.97 C.10
1.2036 B.16 C.10 1.2077 B.57 C.10 1.2118 B.98 C.10
1.2037 B.17 C.10 1.2078 B.58 C.10 1.2119 B.99 C.10
1.2038 B.18 C.10 1.2079 B.59 C.10 1.2120 B.100 C.10
1.2039 B.19 C.10 1.2080 B.60 C.10 1.2121 B.101 C.10
1.2040 B.20 C.10 1.2081 B.61 C.10 1.2122 B.102 C.10
1.2041 B.21 C.10 1.2082 B.62 C.10 1.2123 B.103 C.10
1.2042 B.22 C.10 1.2083 B.63 C.10 1.2124 B.104 C.10 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.2125 B.105 C.10 1.2166 B.146 C.10 1.2207 B.187 C.10
1.2126 B.106 C.10 1.2167 B.147 C.10 1.2208 B.188 C.10
1.2127 B.107 C.10 1.2168 B.148 C.10 1.2209 B.189 C.10
1.2128 B.108 C.10 1.2169 B.149 C.10 1.2210 B.190 C.10
1.2129 B.109 C.10 1.2170 B.150 C.10 1.2211 B.191 C.10
1.2130 B.110 C.10 1.2171 B.151 C.10 1.2212 B.192 C.10
1.2131 B.111 C.10 1.2172 B.152 C.10 1.2213 B.193 C.10
1.2132 B.112 C.10 1.2173 B.153 C.10 1.2214 B.194 C.10
1.2133 B.113 C.10 1.2174 B.154 C.10 1.2215 B.195 C.10
1.2134 B.114 C.10 1.2175 B.155 C.10 1.2216 B.196 C.10
1.2135 B.115 C.10 1.2176 B.156 C.10 1.2217 B.197 C.10
1.2136 B.116 C.10 1.2177 B.157 C.10 1.2218 B.198 C.10
1.2137 B.117 C.10 1.2178 B.158 C.10 1.2219 B.199 C.10
1.2138 B.118 C.10 1.2179 B.159 C.10 1.2220 B.200 C.10
1.2139 B.119 C.10 1.2180 B.160 C.10 1.2221 B.201 C.10
1.2140 B.120 C.10 1.2181 B.161 C.10 1.2222 B.202 C.10
1.2141 B.121 C.10 1.2182 B.162 C.10 1.2223 B.1 C.11
1.2142 B.122 C.10 1.2183 B.163 C.10 1.2224 B.2 C.11
1.2143 B.123 C.10 1.2184 B.164 C.10 1.2225 B.3 C.11
1.2144 B.124 C.10 1.2185 B.165 C.10 1.2226 B.4 C.11
1.2145 B.125 C.10 1.2186 B.166 C.10 1.2227 B.5 C.11
1.2146 B.126 C.10 1.2187 B.167 C.10 1.2228 B.6 C.11
1.2147 B.127 C.10 1.2188 B.168 C.10 1.2229 B.7 C.11
1.2148 B.128 C.10 1.2189 B.169 C.10 1.2230 B.8 C.11
1.2149 B.129 C.10 1.2190 B.170 C.10 1.2231 B.9 C.11
1.2150 B.130 C.10 1.2191 B.171 C.10 1.2232 B.10 C.11
1.2151 B.131 C.10 1.2192 B.172 C.10 1.2233 B.11 C.11
1.2152 B.132 C.10 1.2193 B.173 C.10 1.2234 B.12 C.11
1.2153 B.133 C.10 1.2194 B.174 C.10 1.2235 B.13 C.11
1.2154 B.134 C.10 1.2195 B.175 C.10 1.2236 B.14 C.11
1.2155 B.135 C.10 1.2196 B.176 C.10 1.2237 B.15 C.11
1.2156 B.136 C.10 1.2197 B.177 C.10 1.2238 B.16 C.11
1.2157 B.137 C.10 1.2198 B.178 C.10 1.2239 B.17 C.11
1.2158 B.138 C.10 1.2199 B.179 C.10 1.2240 B.18 C.11
1.2159 B.139 C.10 1.2200 B.180 C.10 1.2241 B.19 C.11
1.2160 B.140 C.10 1.2201 B.181 C.10 1.2242 B.20 C.11
1.2161 B.141 C.10 1.2202 B.182 C.10 1.2243 B.21 C.11
1.2162 B.142 C.10 1.2203 B.183 C.10 1.2244 B.22 C.11
1.2163 B.143 C.10 1.2204 B.184 C.10 1.2245 B.23 C.11
1.2164 B.144 C.10 1.2205 B.185 C.10 1.2246 B.24 C.11
1.2165 B.145 C.10 1.2206 B.186 C.10 1.2247 B.25 C.11 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.2248 B.26 C.11 1.2289 B.67 C.11 1.2330 B.108 C.11
1.2249 B.27 C.11 1.2290 B.68 C.11 1.2331 B.109 C.11
1.2250 B.28 C.11 1.2291 B.69 C.11 1.2332 B.110 C.11
1.2251 B.29 C.11 1.2292 B.70 C.11 1.2333 B.111 C.11
1.2252 B.30 C.11 1.2293 B.71 C.11 1.2334 B.112 C.11
1.2253 B.31 C.11 1.2294 B.72 C.11 1.2335 B.113 C.11
1.2254 B.32 C.11 1.2295 B.73 C.11 1.2336 B.114 C.11
1.2255 B.33 C.11 1.2296 B.74 C.11 1.2337 B.115 C.11
1.2256 B.34 C.11 1.2297 B.75 C.11 1.2338 B.116 C.11
1.2257 B.35 C.11 1.2298 B.76 C.11 1.2339 B.117 C.11
1.2258 B.36 C.11 1.2299 B.77 C.11 1.2340 B.118 C.11
1.2259 B.37 C.11 1.2300 B.78 C.11 1.2341 B.119 C.11
1.2260 B.38 C.11 1.2301 B.79 C.11 1.2342 B.120 C.11
1.2261 B.39 C.11 1.2302 B.80 C.11 1.2343 B.121 C.11
1.2262 B.40 C.11 1.2303 B.81 C.11 1.2344 B.122 C.11
1.2263 B.41 C.11 1.2304 B.82 C.11 1.2345 B.123 C.11
1.2264 B.42 C.11 1.2305 B.83 C.11 1.2346 B.124 C.11
1.2265 B.43 C.11 1.2306 B.84 C.11 1.2347 B.125 C.11
1.2266 B.44 C.11 1.2307 B.85 C.11 1.2348 B.126 C.11
1.2267 B.45 C.11 1.2308 B.86 C.11 1.2349 B.127 C.11
1.2268 B.46 C.11 1.2309 B.87 C.11 1.2350 B.128 C.11
1.2269 B.47 C.11 1.2310 B.88 C.11 1.2351 B.129 C.11
1.2270 B.48 C.11 1.2311 B.89 C.11 1.2352 B.130 C.11
1.2271 B.49 C.11 1.2312 B.90 C.11 1.2353 B.131 C.11
1.2272 B.50 C.11 1.2313 B.91 C.11 1.2354 B.132 C.11
1.2273 B.51 C.11 1.2314 B.92 C.11 1.2355 B.133 C.11
1.2274 B.52 C.11 1.2315 B.93 C.11 1.2356 B.134 C.11
1.2275 B.53 C.11 1.2316 B.94 C.11 1.2357 B.135 C.11
1.2276 B.54 C.11 1.2317 B.95 C.11 1.2358 B.136 C.11
1.2277 B.55 C.11 1.2318 B.96 C.11 1.2359 B.137 C.11
1.2278 B.56 C.11 1.2319 B.97 C.11 1.2360 B.138 C.11
1.2279 B.57 C.11 1.2320 B.98 C.11 1.2361 B.139 C.11
1.2280 B.58 C.11 1.2321 B.99 C.11 1.2362 B.140 C.11
1.2281 B.59 C.11 1.2322 B.100 C.11 1.2363 B.141 C.11
1.2282 B.60 C.11 1.2323 B.101 C.11 1.2364 B.142 C.11
1.2283 B.61 C.11 1.2324 B.102 C.11 1.2365 B.143 C.11
1.2284 B.62 C.11 1.2325 B.103 C.11 1.2366 B.144 C.11
1.2285 B.63 C.11 1.2326 B.104 C.11 1.2367 B.145 C.11
1.2286 B.64 C.11 1.2327 B.105 C.11 1.2368 B.146 C.11
1.2287 B.65 C.11 1.2328 B.106 C.11 1.2369 B.147 C.11
1.2288 B.66 C.11 1.2329 B.107 C.11 1.2370 B.148 C.11 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.2371 B.149 C.11 1.2412 B.190 C.11 1.2453 B.29 C.12
1.2372 B.150 C.11 1.2413 B.191 C.11 1.2454 B.30 C.12
1.2373 B.151 C.11 1.2414 B.192 C.11 1.2455 B.31 C.12
1.2374 B.152 C.11 1.2415 B.193 C.11 1.2456 B.32 C.12
1.2375 B.153 C.11 1.2416 B.194 C.11 1.2457 B.33 C.12
1.2376 B.154 C.11 1.2417 B.195 C.11 1.2458 B.34 C.12
1.2377 B.155 C.11 1.2418 B.196 C.11 1.2459 B.35 C.12
1.2378 B.156 C.11 1.2419 B.197 C.11 1.2460 B.36 C.12
1.2379 B.157 C.11 1.2420 B.198 C.11 1.2461 B.37 C.12
1.2380 B.158 C.11 1.2421 B.199 C.11 1.2462 B.38 C.12
1.2381 B.159 C.11 1.2422 B.200 C.11 1.2463 B.39 C.12
1.2382 B.160 C.11 1.2423 B.201 C.11 1.2464 B.40 C.12
1.2383 B.161 C.11 1.2424 B.202 C.11 1.2465 B.41 C.12
1.2384 B.162 C.11 1.2425 B.1 C.12 1.2466 B.42 C.12
1.2385 B.163 C.11 1.2426 B.2 C.12 1.2467 B.43 C.12
1.2386 B.164 C.11 1.2427 B.3 C.12 1.2468 B.44 C.12
1.2387 B.165 C.11 1.2428 B.4 C.12 1.2469 B.45 C.12
1.2388 B.166 C.11 1.2429 B.5 C.12 1.2470 B.46 C.12
1.2389 B.167 C.11 1.2430 B.6 C.12 1.2471 B.47 C.12
1.2390 B.168 C.11 1.2431 B.7 C.12 1.2472 B.48 C.12
1.2391 B.169 C.11 1.2432 B.8 C.12 1.2473 B.49 C.12
1.2392 B.170 C.11 1.2433 B.9 C.12 1.2474 B.50 C.12
1.2393 B.171 C.11 1.2434 B.10 C.12 1.2475 B.51 C.12
1.2394 B.172 C.11 1.2435 B.11 C.12 1.2476 B.52 C.12
1.2395 B.173 C.11 1.2436 B.12 C.12 1.2477 B.53 C.12
1.2396 B.174 C.11 1.2437 B.13 C.12 1.2478 B.54 C.12
1.2397 B.175 C.11 1.2438 B.14 C.12 1.2479 B.55 C.12
1.2398 B.176 C.11 1.2439 B.15 C.12 1.2480 B.56 C.12
1.2399 B.177 C.11 1.2440 B.16 C.12 1.2481 B.57 C.12
1.2400 B.178 C.11 1.2441 B.17 C.12 1.2482 B.58 C.12
1.2401 B.179 C.11 1.2442 B.18 C.12 1.2483 B.59 C.12
1.2402 B.180 C.11 1.2443 B.19 C.12 1.2484 B.60 C.12
1.2403 B.181 C.11 1.2444 B.20 C.12 1.2485 B.61 C.12
1.2404 B.182 C.11 1.2445 B.21 C.12 1.2486 B.62 C.12
1.2405 B.183 C.11 1.2446 B.22 C.12 1.2487 B.63 C.12
1.2406 B.184 C.11 1.2447 B.23 C.12 1.2488 B.64 C.12
1.2407 B.185 C.11 1.2448 B.24 C.12 1.2489 B.65 C.12
1.2408 B.186 C.11 1.2449 B.25 C.12 1.2490 B.66 C.12
1.2409 B.187 C.11 1.2450 B.26 C.12 1.2491 B.67 C.12
1.2410 B.188 C.11 1.2451 B.27 C.12 1.2492 B.68 C.12
1.2411 B.189 C.11 1.2452 B.28 C.12 1.2493 B.69 C.12 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.2494 B.70 C.12 1.2535 B.111 C.12 1.2576 B.152 C.12
1.2495 B.71 C.12 1.2536 B.112 C.12 1.2577 B.153 C.12
1.2496 B.72 C.12 1.2537 B.113 C.12 1.2578 B.154 C.12
1.2497 B.73 C.12 1.2538 B.114 C.12 1.2579 B.155 C.12
1.2498 B.74 C.12 1.2539 B.115 C.12 1.2580 B.156 C.12
1.2499 B.75 C.12 1.2540 B.116 C.12 1.2581 B.157 C.12
1.2500 B.76 C.12 1.2541 B.117 C.12 1.2582 B.158 C.12
1.2501 B.77 C.12 1.2542 B.118 C.12 1.2583 B.159 C.12
1.2502 B.78 C.12 1.2543 B.119 C.12 1.2584 B.160 C.12
1.2503 B.79 C.12 1.2544 B.120 C.12 1.2585 B.161 C.12
1.2504 B.80 C.12 1.2545 B.121 C.12 1.2586 B.162 C.12
1.2505 B.81 C.12 1.2546 B.122 C.12 1.2587 B.163 C.12
1.2506 B.82 C.12 1.2547 B.123 C.12 1.2588 B.164 C.12
1.2507 B.83 C.12 1.2548 B.124 C.12 1.2589 B.165 C.12
1.2508 B.84 C.12 1.2549 B.125 C.12 1.2590 B.166 C.12
1.2509 B.85 C.12 1.2550 B.126 C.12 1.2591 B.167 C.12
1.2510 B.86 C.12 1.2551 B.127 C.12 1.2592 B.168 C.12
1.2511 B.87 C.12 1.2552 B.128 C.12 1.2593 B.169 C.12
1.2512 B.88 C.12 1.2553 B.129 C.12 1.2594 B.170 C.12
1.2513 B.89 C.12 1.2554 B.130 C.12 1.2595 B.171 C.12
1.2514 B.90 C.12 1.2555 B.131 C.12 1.2596 B.172 C.12
1.2515 B.91 C.12 1.2556 B.132 C.12 1.2597 B.173 C.12
1.2516 B.92 C.12 1.2557 B.133 C.12 1.2598 B.174 C.12
1.2517 B.93 C.12 1.2558 B.134 C.12 1.2599 B.175 C.12
1.2518 B.94 C.12 1.2559 B.135 C.12 1.2600 B.176 C.12
1.2519 B.95 C.12 1.2560 B.136 C.12 1.2601 B.177 C.12
1.2520 B.96 C.12 1.2561 B.137 C.12 1.2602 B.178 C.12
1.2521 B.97 C.12 1.2562 B.138 C.12 1.2603 B.179 C.12
1.2522 B.98 C.12 1.2563 B.139 C.12 1.2604 B.180 C.12
1.2523 B.99 C.12 1.2564 B.140 C.12 1.2605 B.181 C.12
1.2524 B.100 C.12 1.2565 B.141 C.12 1.2606 B.182 C.12
1.2525 B.101 C.12 1.2566 B.142 C.12 1.2607 B.183 C.12
1.2526 B.102 C.12 1.2567 B.143 C.12 1.2608 B.184 C.12
1.2527 B.103 C.12 1.2568 B.144 C.12 1.2609 B.185 C.12
1.2528 B.104 C.12 1.2569 B.145 C.12 1.2610 B.186 C.12
1.2529 B.105 C.12 1.2570 B.146 C.12 1.2611 B.187 C.12
1.2530 B.106 C.12 1.2571 B.147 C.12 1.2612 B.188 C.12
1.2531 B.107 C.12 1.2572 B.148 C.12 1.2613 B.189 C.12
1.2532 B.108 C.12 1.2573 B.149 C.12 1.2614 B.190 C.12
1.2533 B.109 C.12 1.2574 B.150 C.12 1.2615 B.191 C.12
1.2534 B.110 C.12 1.2575 B.151 C.12 1.2616 B.192 C.12 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.2617 B.193 C.12 1.2658 B.32 C.13 1 .2699 B.73 C.13
1.2618 B.194 C.12 1.2659 B.33 C.13 1 .2700 B.74 C.13
1.2619 B.195 C.12 1.2660 B.34 C.13 1 .2701 B.75 C.13
1.2620 B.196 C.12 1.2661 B.35 C.13 1 .2702 B.76 C.13
1.2621 B.197 C.12 1.2662 B.36 C.13 1 .2703 B.77 C.13
1.2622 B.198 C.12 1.2663 B.37 C.13 1 .2704 B.78 C.13
1.2623 B.199 C.12 1.2664 B.38 C.13 1 .2705 B.79 C.13
1.2624 B.200 C.12 1.2665 B.39 C.13 1 .2706 B.80 C.13
1.2625 B.201 C.12 1.2666 B.40 C.13 1 .2707 B.81 C.13
1.2626 B.202 C.12 1.2667 B.41 C.13 1 .2708 B.82 C.13
1.2627 B.1 C.13 1.2668 B.42 C.13 1 .2709 B.83 C.13
1.2628 B.2 C.13 1.2669 B.43 C.13 1 .2710 B.84 C.13
1.2629 B.3 C.13 1.2670 B.44 C.13 1 .271 1 B.85 C.13
1.2630 B.4 C.13 1.2671 B.45 C.13 1 .2712 B.86 C.13
1.2631 B.5 C.13 1.2672 B.46 C.13 1 .2713 B.87 C.13
1.2632 B.6 C.13 1.2673 B.47 C.13 1 .2714 B.88 C.13
1.2633 B.7 C.13 1.2674 B.48 C.13 1 .2715 B.89 C.13
1.2634 B.8 C.13 1.2675 B.49 C.13 1 .2716 B.90 C.13
1.2635 B.9 C.13 1.2676 B.50 C.13 1 .2717 B.91 C.13
1.2636 B.10 C.13 1.2677 B.51 C.13 1 .2718 B.92 C.13
1.2637 B.1 1 C.13 1.2678 B.52 C.13 1 .2719 B.93 C.13
1.2638 B.12 C.13 1.2679 B.53 C.13 1 .2720 B.94 C.13
1.2639 B.13 C.13 1.2680 B.54 C.13 1 .2721 B.95 C.13
1.2640 B.14 C.13 1.2681 B.55 C.13 1 .2722 B.96 C.13
1.2641 B.15 C.13 1.2682 B.56 C.13 1 .2723 B.97 C.13
1.2642 B.16 C.13 1.2683 B.57 C.13 1 .2724 B.98 C.13
1.2643 B.17 C.13 1.2684 B.58 C.13 1 .2725 B.99 C.13
1.2644 B.18 C.13 1.2685 B.59 C.13 1 .2726 B.100 C.13
1.2645 B.19 C.13 1.2686 B.60 C.13 1 .2727 B.101 C.13
1.2646 B.20 C.13 1.2687 B.61 C.13 1 .2728 B.102 C.13
1.2647 B.21 C.13 1.2688 B.62 C.13 1 .2729 B.103 C.13
1.2648 B.22 C.13 1.2689 B.63 C.13 1 .2730 B.104 C.13
1.2649 B.23 C.13 1.2690 B.64 C.13 1 .2731 B.105 C.13
1.2650 B.24 C.13 1.2691 B.65 C.13 1 .2732 B.106 C.13
1.2651 B.25 C.13 1.2692 B.66 C.13 1 .2733 B.107 C.13
1.2652 B.26 C.13 1.2693 B.67 C.13 1 .2734 B.108 C.13
1.2653 B.27 C.13 1.2694 B.68 C.13 1 .2735 B.109 C.13
1.2654 B.28 C.13 1.2695 B.69 C.13 1 .2736 B.1 10 C.13
1.2655 B.29 C.13 1.2696 B.70 C.13 1 .2737 B.1 1 1 C.13
1.2656 B.30 C.13 1.2697 B.71 C.13 1 .2738 B.1 12 C.13
1.2657 B.31 C.13 1.2698 B.72 C.13 1 .2739 B.1 13 C.13 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.2740 B.1 14 C.13 1.2781 B.155 C.13 1 .2822 B.196 C.13
1.2741 B.1 15 C.13 1.2782 B.156 C.13 1 .2823 B.197 C.13
1.2742 B.1 16 C.13 1.2783 B.157 C.13 1 .2824 B.198 C.13
1.2743 B.1 17 C.13 1.2784 B.158 C.13 1 .2825 B.199 C.13
1.2744 B.1 18 C.13 1.2785 B.159 C.13 1 .2826 B.200 C.13
1.2745 B.1 19 C.13 1.2786 B.160 C.13 1 .2827 B.201 C.13
1.2746 B.120 C.13 1.2787 B.161 C.13 1 .2828 B.202 C.13
1.2747 B.121 C.13 1.2788 B.162 C.13 1 .2829 B.1 C.14
1.2748 B.122 C.13 1.2789 B.163 C.13 1 .2830 B.2 C.14
1.2749 B.123 C.13 1.2790 B.164 C.13 1 .2831 B.3 C.14
1.2750 B.124 C.13 1.2791 B.165 C.13 1 .2832 B.4 C.14
1.2751 B.125 C.13 1.2792 B.166 C.13 1 .2833 B.5 C.14
1.2752 B.126 C.13 1.2793 B.167 C.13 1 .2834 B.6 C.14
1.2753 B.127 C.13 1.2794 B.168 C.13 1 .2835 B.7 C.14
1.2754 B.128 C.13 1.2795 B.169 C.13 1 .2836 B.8 C.14
1.2755 B.129 C.13 1.2796 B.170 C.13 1 .2837 B.9 C.14
1.2756 B.130 C.13 1.2797 B.171 C.13 1 .2838 B.10 C.14
1.2757 B.131 C.13 1.2798 B.172 C.13 1 .2839 B.1 1 C.14
1.2758 B.132 C.13 1.2799 B.173 C.13 1 .2840 B.12 C.14
1.2759 B.133 C.13 1.2800 B.174 C.13 1 .2841 B.13 C.14
1.2760 B.134 C.13 1.2801 B.175 C.13 1 .2842 B.14 C.14
1.2761 B.135 C.13 1.2802 B.176 C.13 1 .2843 B.15 C.14
1.2762 B.136 C.13 1.2803 B.177 C.13 1 .2844 B.16 C.14
1.2763 B.137 C.13 1.2804 B.178 C.13 1 .2845 B.17 C.14
1.2764 B.138 C.13 1.2805 B.179 C.13 1 .2846 B.18 C.14
1.2765 B.139 C.13 1.2806 B.180 C.13 1 .2847 B.19 C.14
1.2766 B.140 C.13 1.2807 B.181 C.13 1 .2848 B.20 C.14
1.2767 B.141 C.13 1.2808 B.182 C.13 1 .2849 B.21 C.14
1.2768 B.142 C.13 1.2809 B.183 C.13 1 .2850 B.22 C.14
1.2769 B.143 C.13 1.2810 B.184 C.13 1 .2851 B.23 C.14
1.2770 B.144 C.13 1.281 1 B.185 C.13 1 .2852 B.24 C.14
1.2771 B.145 C.13 1.2812 B.186 C.13 1 .2853 B.25 C.14
1.2772 B.146 C.13 1.2813 B.187 C.13 1 .2854 B.26 C.14
1.2773 B.147 C.13 1.2814 B.188 C.13 1 .2855 B.27 C.14
1.2774 B.148 C.13 1.2815 B.189 C.13 1 .2856 B.28 C.14
1.2775 B.149 C.13 1.2816 B.190 C.13 1 .2857 B.29 C.14
1.2776 B.150 C.13 1.2817 B.191 C.13 1 .2858 B.30 C.14
1.2777 B.151 C.13 1.2818 B.192 C.13 1 .2859 B.31 C.14
1.2778 B.152 C.13 1.2819 B.193 C.13 1 .2860 B.32 C.14
1.2779 B.153 C.13 1.2820 B.194 C.13 1 .2861 B.33 C.14
1.2780 B.154 C.13 1.2821 B.195 C.13 1 .2862 B.34 C.14 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.2863 B.35 C.14 1.2904 B.76 C.14 1 .2945 B.1 17 C.14
1.2864 B.36 C.14 1.2905 B.77 C.14 1 .2946 B.1 18 C.14
1.2865 B.37 C.14 1.2906 B.78 C.14 1 .2947 B.1 19 C.14
1.2866 B.38 C.14 1.2907 B.79 C.14 1 .2948 B.120 C.14
1.2867 B.39 C.14 1.2908 B.80 C.14 1 .2949 B.121 C.14
1.2868 B.40 C.14 1.2909 B.81 C.14 1 .2950 B.122 C.14
1.2869 B.41 C.14 1.2910 B.82 C.14 1 .2951 B.123 C.14
1.2870 B.42 C.14 1.291 1 B.83 C.14 1 .2952 B.124 C.14
1.2871 B.43 C.14 1.2912 B.84 C.14 1 .2953 B.125 C.14
1.2872 B.44 C.14 1.2913 B.85 C.14 1 .2954 B.126 C.14
1.2873 B.45 C.14 1.2914 B.86 C.14 1 .2955 B.127 C.14
1.2874 B.46 C.14 1.2915 B.87 C.14 1 .2956 B.128 C.14
1.2875 B.47 C.14 1.2916 B.88 C.14 1 .2957 B.129 C.14
1.2876 B.48 C.14 1.2917 B.89 C.14 1 .2958 B.130 C.14
1.2877 B.49 C.14 1.2918 B.90 C.14 1 .2959 B.131 C.14
1.2878 B.50 C.14 1.2919 B.91 C.14 1 .2960 B.132 C.14
1.2879 B.51 C.14 1.2920 B.92 C.14 1 .2961 B.133 C.14
1.2880 B.52 C.14 1.2921 B.93 C.14 1 .2962 B.134 C.14
1.2881 B.53 C.14 1.2922 B.94 C.14 1 .2963 B.135 C.14
1.2882 B.54 C.14 1.2923 B.95 C.14 1 .2964 B.136 C.14
1.2883 B.55 C.14 1.2924 B.96 C.14 1 .2965 B.137 C.14
1.2884 B.56 C.14 1.2925 B.97 C.14 1 .2966 B.138 C.14
1.2885 B.57 C.14 1.2926 B.98 C.14 1 .2967 B.139 C.14
1.2886 B.58 C.14 1.2927 B.99 C.14 1 .2968 B.140 C.14
1.2887 B.59 C.14 1.2928 B.100 C.14 1 .2969 B.141 C.14
1.2888 B.60 C.14 1.2929 B.101 C.14 1 .2970 B.142 C.14
1.2889 B.61 C.14 1.2930 B.102 C.14 1 .2971 B.143 C.14
1.2890 B.62 C.14 1.2931 B.103 C.14 1 .2972 B.144 C.14
1.2891 B.63 C.14 1.2932 B.104 C.14 1 .2973 B.145 C.14
1.2892 B.64 C.14 1.2933 B.105 C.14 1 .2974 B.146 C.14
1.2893 B.65 C.14 1.2934 B.106 C.14 1 .2975 B.147 C.14
1.2894 B.66 C.14 1.2935 B.107 C.14 1 .2976 B.148 C.14
1.2895 B.67 C.14 1.2936 B.108 C.14 1 .2977 B.149 C.14
1.2896 B.68 C.14 1.2937 B.109 C.14 1 .2978 B.150 C.14
1.2897 B.69 C.14 1.2938 B.1 10 C.14 1 .2979 B.151 C.14
1.2898 B.70 C.14 1.2939 B.1 1 1 C.14 1 .2980 B.152 C.14
1.2899 B.71 C.14 1.2940 B.1 12 C.14 1 .2981 B.153 C.14
1.2900 B.72 C.14 1.2941 B.1 13 C.14 1 .2982 B.154 C.14
1.2901 B.73 C.14 1.2942 B.1 14 C.14 1 .2983 B.155 C.14
1.2902 B.74 C.14 1.2943 B.1 15 C.14 1 .2984 B.156 C.14
1.2903 B.75 C.14 1.2944 B.1 16 C.14 1 .2985 B.157 C.14 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.2986 B.158 C.14 1.3027 B.199 C.14 1 .3068 B.38 C.15
1.2987 B.159 C.14 1.3028 B.200 C.14 1 .3069 B.39 C.15
1.2988 B.160 C.14 1.3029 B.201 C.14 1 .3070 B.40 C.15
1.2989 B.161 C.14 1.3030 B.202 C.14 1 .3071 B.41 C.15
1.2990 B.162 C.14 1.3031 B.1 C.15 1 .3072 B.42 C.15
1.2991 B.163 C.14 1.3032 B.2 C.15 1 .3073 B.43 C.15
1.2992 B.164 C.14 1.3033 B.3 C.15 1 .3074 B.44 C.15
1.2993 B.165 C.14 1.3034 B.4 C.15 1 .3075 B.45 C.15
1.2994 B.166 C.14 1.3035 B.5 C.15 1 .3076 B.46 C.15
1.2995 B.167 C.14 1.3036 B.6 C.15 1 .3077 B.47 C.15
1.2996 B.168 C.14 1.3037 B.7 C.15 1 .3078 B.48 C.15
1.2997 B.169 C.14 1.3038 B.8 C.15 1 .3079 B.49 C.15
1.2998 B.170 C.14 1.3039 B.9 C.15 1 .3080 B.50 C.15
1.2999 B.171 C.14 1.3040 B.10 C.15 1 .3081 B.51 C.15
1.3000 B.172 C.14 1.3041 B.1 1 C.15 1 .3082 B.52 C.15
1.3001 B.173 C.14 1.3042 B.12 C.15 1 .3083 B.53 C.15
1.3002 B.174 C.14 1.3043 B.13 C.15 1 .3084 B.54 C.15
1.3003 B.175 C.14 1.3044 B.14 C.15 1 .3085 B.55 C.15
1.3004 B.176 C.14 1.3045 B.15 C.15 1 .3086 B.56 C.15
1.3005 B.177 C.14 1.3046 B.16 C.15 1 .3087 B.57 C.15
1.3006 B.178 C.14 1.3047 B.17 C.15 1 .3088 B.58 C.15
1.3007 B.179 C.14 1.3048 B.18 C.15 1 .3089 B.59 C.15
1.3008 B.180 C.14 1.3049 B.19 C.15 1 .3090 B.60 C.15
1.3009 B.181 C.14 1.3050 B.20 C.15 1 .3091 B.61 C.15
1.3010 B.182 C.14 1.3051 B.21 C.15 1 .3092 B.62 C.15
1.301 1 B.183 C.14 1.3052 B.22 C.15 1 .3093 B.63 C.15
1.3012 B.184 C.14 1.3053 B.23 C.15 1 .3094 B.64 C.15
1.3013 B.185 C.14 1.3054 B.24 C.15 1 .3095 B.65 C.15
1.3014 B.186 C.14 1.3055 B.25 C.15 1 .3096 B.66 C.15
1.3015 B.187 C.14 1.3056 B.26 C.15 1 .3097 B.67 C.15
1.3016 B.188 C.14 1.3057 B.27 C.15 1 .3098 B.68 C.15
1.3017 B.189 C.14 1.3058 B.28 C.15 1 .3099 B.69 C.15
1.3018 B.190 C.14 1.3059 B.29 C.15 1 .3100 B.70 C.15
1.3019 B.191 C.14 1.3060 B.30 C.15 1 .3101 B.71 C.15
1.3020 B.192 C.14 1.3061 B.31 C.15 1 .3102 B.72 C.15
1.3021 B.193 C.14 1.3062 B.32 C.15 1 .3103 B.73 C.15
1.3022 B.194 C.14 1.3063 B.33 C.15 1 .3104 B.74 C.15
1.3023 B.195 C.14 1.3064 B.34 C.15 1 .3105 B.75 C.15
1.3024 B.196 C.14 1.3065 B.35 C.15 1 .3106 B.76 C.15
1.3025 B.197 C.14 1.3066 B.36 C.15 1 .3107 B.77 C.15
1.3026 B.198 C.14 1.3067 B.37 C.15 1 .3108 B.78 C.15 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.3109 B.79 C.15 1.3150 B.120 C.15 1.3191 B.161 C.15
1.3110 B.80 C.15 1.3151 B.121 C.15 1.3192 B.162 C.15
1.3111 B.81 C.15 1.3152 B.122 C.15 1.3193 B.163 C.15
1.3112 B.82 C.15 1.3153 B.123 C.15 1.3194 B.164 C.15
1.3113 B.83 C.15 1.3154 B.124 C.15 1.3195 B.165 C.15
1.3114 B.84 C.15 1.3155 B.125 C.15 1.3196 B.166 C.15
1.3115 B.85 C.15 1.3156 B.126 C.15 1.3197 B.167 C.15
1.3116 B.86 C.15 1.3157 B.127 C.15 1.3198 B.168 C.15
1.3117 B.87 C.15 1.3158 B.128 C.15 1.3199 B.169 C.15
1.3118 B.88 C.15 1.3159 B.129 C.15 1.3200 B.170 C.15
1.3119 B.89 C.15 1.3160 B.130 C.15 1.3201 B.171 C.15
1.3120 B.90 C.15 1.3161 B.131 C.15 1.3202 B.172 C.15
1.3121 B.91 C.15 1.3162 B.132 C.15 1.3203 B.173 C.15
1.3122 B.92 C.15 1.3163 B.133 C.15 1.3204 B.174 C.15
1.3123 B.93 C.15 1.3164 B.134 C.15 1.3205 B.175 C.15
1.3124 B.94 C.15 1.3165 B.135 C.15 1.3206 B.176 C.15
1.3125 B.95 C.15 1.3166 B.136 C.15 1.3207 B.177 C.15
1.3126 B.96 C.15 1.3167 B.137 C.15 1.3208 B.178 C.15
1.3127 B.97 C.15 1.3168 B.138 C.15 1.3209 B.179 C.15
1.3128 B.98 C.15 1.3169 B.139 C.15 1.3210 B.180 C.15
1.3129 B.99 C.15 1.3170 B.140 C.15 1.3211 B.181 C.15
1.3130 B.100 C.15 1.3171 B.141 C.15 1.3212 B.182 C.15
1.3131 B.101 C.15 1.3172 B.142 C.15 1.3213 B.183 C.15
1.3132 B.102 C.15 1.3173 B.143 C.15 1.3214 B.184 C.15
1.3133 B.103 C.15 1.3174 B.144 C.15 1.3215 B.185 C.15
1.3134 B.104 C.15 1.3175 B.145 C.15 1.3216 B.186 C.15
1.3135 B.105 C.15 1.3176 B.146 C.15 1.3217 B.187 C.15
1.3136 B.106 C.15 1.3177 B.147 C.15 1.3218 B.188 C.15
1.3137 B.107 C.15 1.3178 B.148 C.15 1.3219 B.189 C.15
1.3138 B.108 C.15 1.3179 B.149 C.15 1.3220 B.190 C.15
1.3139 B.109 C.15 1.3180 B.150 C.15 1.3221 B.191 C.15
1.3140 B.110 C.15 1.3181 B.151 C.15 1.3222 B.192 C.15
1.3141 B.111 C.15 1.3182 B.152 C.15 1.3223 B.193 C.15
1.3142 B.112 C.15 1.3183 B.153 C.15 1.3224 B.194 C.15
1.3143 B.113 C.15 1.3184 B.154 C.15 1.3225 B.195 C.15
1.3144 B.114 C.15 1.3185 B.155 C.15 1.3226 B.196 C.15
1.3145 B.115 C.15 1.3186 B.156 C.15 1.3227 B.197 C.15
1.3146 B.116 C.15 1.3187 B.157 C.15 1.3228 B.198 C.15
1.3147 B.117 C.15 1.3188 B.158 C.15 1.3229 B.199 C.15
1.3148 B.118 C.15 1.3189 B.159 C.15 1.3230 B.200 C.15
1.3149 B.119 C.15 1.3190 B.160 C.15 1.3231 B.201 C.15 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.3232 B.202 C.15 1.3273 B.41 C.16 1 .3314 B.82 C.16
1.3233 B.1 C.16 1.3274 B.42 C.16 1 .3315 B.83 C.16
1.3234 B.2 C.16 1.3275 B.43 C.16 1 .3316 B.84 C.16
1.3235 B.3 C.16 1.3276 B.44 C.16 1 .3317 B.85 C.16
1.3236 B.4 C.16 1.3277 B.45 C.16 1 .3318 B.86 C.16
1.3237 B.5 C.16 1.3278 B.46 C.16 1 .3319 B.87 C.16
1.3238 B.6 C.16 1.3279 B.47 C.16 1 .3320 B.88 C.16
1.3239 B.7 C.16 1.3280 B.48 C.16 1 .3321 B.89 C.16
1.3240 B.8 C.16 1.3281 B.49 C.16 1 .3322 B.90 C.16
1.3241 B.9 C.16 1.3282 B.50 C.16 1 .3323 B.91 C.16
1.3242 B.10 C.16 1.3283 B.51 C.16 1 .3324 B.92 C.16
1.3243 B.1 1 C.16 1.3284 B.52 C.16 1 .3325 B.93 C.16
1.3244 B.12 C.16 1.3285 B.53 C.16 1 .3326 B.94 C.16
1.3245 B.13 C.16 1.3286 B.54 C.16 1 .3327 B.95 C.16
1.3246 B.14 C.16 1.3287 B.55 C.16 1 .3328 B.96 C.16
1.3247 B.15 C.16 1.3288 B.56 C.16 1 .3329 B.97 C.16
1.3248 B.16 C.16 1.3289 B.57 C.16 1 .3330 B.98 C.16
1.3249 B.17 C.16 1.3290 B.58 C.16 1 .3331 B.99 C.16
1.3250 B.18 C.16 1.3291 B.59 C.16 1 .3332 B.100 C.16
1.3251 B.19 C.16 1.3292 B.60 C.16 1 .3333 B.101 C.16
1.3252 B.20 C.16 1.3293 B.61 C.16 1 .3334 B.102 C.16
1.3253 B.21 C.16 1.3294 B.62 C.16 1 .3335 B.103 C.16
1.3254 B.22 C.16 1.3295 B.63 C.16 1 .3336 B.104 C.16
1.3255 B.23 C.16 1.3296 B.64 C.16 1 .3337 B.105 C.16
1.3256 B.24 C.16 1.3297 B.65 C.16 1 .3338 B.106 C.16
1.3257 B.25 C.16 1.3298 B.66 C.16 1 .3339 B.107 C.16
1.3258 B.26 C.16 1.3299 B.67 C.16 1 .3340 B.108 C.16
1.3259 B.27 C.16 1.3300 B.68 C.16 1 .3341 B.109 C.16
1.3260 B.28 C.16 1.3301 B.69 C.16 1 .3342 B.1 10 C.16
1.3261 B.29 C.16 1.3302 B.70 C.16 1 .3343 B.1 1 1 C.16
1.3262 B.30 C.16 1.3303 B.71 C.16 1 .3344 B.1 12 C.16
1.3263 B.31 C.16 1.3304 B.72 C.16 1 .3345 B.1 13 C.16
1.3264 B.32 C.16 1.3305 B.73 C.16 1 .3346 B.1 14 C.16
1.3265 B.33 C.16 1.3306 B.74 C.16 1 .3347 B.1 15 C.16
1.3266 B.34 C.16 1.3307 B.75 C.16 1 .3348 B.1 16 C.16
1.3267 B.35 C.16 1.3308 B.76 C.16 1 .3349 B.1 17 C.16
1.3268 B.36 C.16 1.3309 B.77 C.16 1 .3350 B.1 18 C.16
1.3269 B.37 C.16 1.3310 B.78 C.16 1 .3351 B.1 19 C.16
1.3270 B.38 C.16 1.331 1 B.79 C.16 1 .3352 B.120 C.16
1.3271 B.39 C.16 1.3312 B.80 C.16 1 .3353 B.121 C.16
1.3272 B.40 C.16 1.3313 B.81 C.16 1 .3354 B.122 C.16 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.3355 B.123 C.16 1.3396 B.164 C.16 1 .3437 B.3 C.17
1.3356 B.124 C.16 1.3397 B.165 C.16 1 .3438 B.4 C.17
1.3357 B.125 C.16 1.3398 B.166 C.16 1 .3439 B.5 C.17
1.3358 B.126 C.16 1.3399 B.167 C.16 1 .3440 B.6 C.17
1.3359 B.127 C.16 1.3400 B.168 C.16 1 .3441 B.7 C.17
1.3360 B.128 C.16 1.3401 B.169 C.16 1 .3442 B.8 C.17
1.3361 B.129 C.16 1.3402 B.170 C.16 1 .3443 B.9 C.17
1.3362 B.130 C.16 1.3403 B.171 C.16 1 .3444 B.10 C.17
1.3363 B.131 C.16 1.3404 B.172 C.16 1 .3445 B.1 1 C.17
1.3364 B.132 C.16 1.3405 B.173 C.16 1 .3446 B.12 C.17
1.3365 B.133 C.16 1.3406 B.174 C.16 1 .3447 B.13 C.17
1.3366 B.134 C.16 1.3407 B.175 C.16 1 .3448 B.14 C.17
1.3367 B.135 C.16 1.3408 B.176 C.16 1 .3449 B.15 C.17
1.3368 B.136 C.16 1.3409 B.177 C.16 1 .3450 B.16 C.17
1.3369 B.137 C.16 1.3410 B.178 C.16 1 .3451 B.17 C.17
1.3370 B.138 C.16 1.341 1 B.179 C.16 1 .3452 B.18 C.17
1.3371 B.139 C.16 1.3412 B.180 C.16 1 .3453 B.19 C.17
1.3372 B.140 C.16 1.3413 B.181 C.16 1 .3454 B.20 C.17
1.3373 B.141 C.16 1.3414 B.182 C.16 1 .3455 B.21 C.17
1.3374 B.142 C.16 1.3415 B.183 C.16 1 .3456 B.22 C.17
1.3375 B.143 C.16 1.3416 B.184 C.16 1 .3457 B.23 C.17
1.3376 B.144 C.16 1.3417 B.185 C.16 1 .3458 B.24 C.17
1.3377 B.145 C.16 1.3418 B.186 C.16 1 .3459 B.25 C.17
1.3378 B.146 C.16 1.3419 B.187 C.16 1 .3460 B.26 C.17
1.3379 B.147 C.16 1.3420 B.188 C.16 1 .3461 B.27 C.17
1.3380 B.148 C.16 1.3421 B.189 C.16 1 .3462 B.28 C.17
1.3381 B.149 C.16 1.3422 B.190 C.16 1 .3463 B.29 C.17
1.3382 B.150 C.16 1.3423 B.191 C.16 1 .3464 B.30 C.17
1.3383 B.151 C.16 1.3424 B.192 C.16 1 .3465 B.31 C.17
1.3384 B.152 C.16 1.3425 B.193 C.16 1 .3466 B.32 C.17
1.3385 B.153 C.16 1.3426 B.194 C.16 1 .3467 B.33 C.17
1.3386 B.154 C.16 1.3427 B.195 C.16 1 .3468 B.34 C.17
1.3387 B.155 C.16 1.3428 B.196 C.16 1 .3469 B.35 C.17
1.3388 B.156 C.16 1.3429 B.197 C.16 1 .3470 B.36 C.17
1.3389 B.157 C.16 1.3430 B.198 C.16 1 .3471 B.37 C.17
1.3390 B.158 C.16 1.3431 B.199 C.16 1 .3472 B.38 C.17
1.3391 B.159 C.16 1.3432 B.200 C.16 1 .3473 B.39 C.17
1.3392 B.160 C.16 1.3433 B.201 C.16 1 .3474 B.40 C.17
1.3393 B.161 C.16 1.3434 B.202 C.16 1 .3475 B.41 C.17
1.3394 B.162 C.16 1.3435 B.1 C.17 1 .3476 B.42 C.17
1.3395 B.163 C.16 1.3436 B.2 C.17 1 .3477 B.43 C.17 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.3478 B.44 C.17 1.3519 B.85 C.17 1.3560 B.126 C.17
1.3479 B.45 C.17 1.3520 B.86 C.17 1.3561 B.127 C.17
1.3480 B.46 C.17 1.3521 B.87 C.17 1.3562 B.128 C.17
1.3481 B.47 C.17 1.3522 B.88 C.17 1.3563 B.129 C.17
1.3482 B.48 C.17 1.3523 B.89 C.17 1.3564 B.130 C.17
1.3483 B.49 C.17 1.3524 B.90 C.17 1.3565 B.131 C.17
1.3484 B.50 C.17 1.3525 B.91 C.17 1.3566 B.132 C.17
1.3485 B.51 C.17 1.3526 B.92 C.17 1.3567 B.133 C.17
1.3486 B.52 C.17 1.3527 B.93 C.17 1.3568 B.134 C.17
1.3487 B.53 C.17 1.3528 B.94 C.17 1.3569 B.135 C.17
1.3488 B.54 C.17 1.3529 B.95 C.17 1.3570 B.136 C.17
1.3489 B.55 C.17 1.3530 B.96 C.17 1.3571 B.137 C.17
1.3490 B.56 C.17 1.3531 B.97 C.17 1.3572 B.138 C.17
1.3491 B.57 C.17 1.3532 B.98 C.17 1.3573 B.139 C.17
1.3492 B.58 C.17 1.3533 B.99 C.17 1.3574 B.140 C.17
1.3493 B.59 C.17 1.3534 B.100 C.17 1.3575 B.141 C.17
1.3494 B.60 C.17 1.3535 B.101 C.17 1.3576 B.142 C.17
1.3495 B.61 C.17 1.3536 B.102 C.17 1.3577 B.143 C.17
1.3496 B.62 C.17 1.3537 B.103 C.17 1.3578 B.144 C.17
1.3497 B.63 C.17 1.3538 B.104 C.17 1.3579 B.145 C.17
1.3498 B.64 C.17 1.3539 B.105 C.17 1.3580 B.146 C.17
1.3499 B.65 C.17 1.3540 B.106 C.17 1.3581 B.147 C.17
1.3500 B.66 C.17 1.3541 B.107 C.17 1.3582 B.148 C.17
1.3501 B.67 C.17 1.3542 B.108 C.17 1.3583 B.149 C.17
1.3502 B.68 C.17 1.3543 B.109 C.17 1.3584 B.150 C.17
1.3503 B.69 C.17 1.3544 B.110 C.17 1.3585 B.151 C.17
1.3504 B.70 C.17 1.3545 B.111 C.17 1.3586 B.152 C.17
1.3505 B.71 C.17 1.3546 B.112 C.17 1.3587 B.153 C.17
1.3506 B.72 C.17 1.3547 B.113 C.17 1.3588 B.154 C.17
1.3507 B.73 C.17 1.3548 B.114 C.17 1.3589 B.155 C.17
1.3508 B.74 C.17 1.3549 B.115 C.17 1.3590 B.156 C.17
1.3509 B.75 C.17 1.3550 B.116 C.17 1.3591 B.157 C.17
1.3510 B.76 C.17 1.3551 B.117 C.17 1.3592 B.158 C.17
1.3511 B.77 C.17 1.3552 B.118 C.17 1.3593 B.159 C.17
1.3512 B.78 C.17 1.3553 B.119 C.17 1.3594 B.160 C.17
1.3513 B.79 C.17 1.3554 B.120 C.17 1.3595 B.161 C.17
1.3514 B.80 C.17 1.3555 B.121 C.17 1.3596 B.162 C.17
1.3515 B.81 C.17 1.3556 B.122 C.17 1.3597 B.163 C.17
1.3516 B.82 C.17 1.3557 B.123 C.17 1.3598 B.164 C.17
1.3517 B.83 C.17 1.3558 B.124 C.17 1.3599 B.165 C.17
1.3518 B.84 C.17 1.3559 B.125 C.17 1.3600 B.166 C.17 comp. herbisafener comp. herbisafener comp. herbisafener no. cide B C no. cide B C no. cide B C
1.3601 B.167 C.17 1.3619 B.185 C.17 1 .3637 — C.1
1.3602 B.168 C.17 1.3620 B.186 C.17 1 .3638 — C.2
1.3603 B.169 C.17 1.3621 B.187 C.17 1 .3639 — C.3
1.3604 B.170 C.17 1.3622 B.188 C.17 1 .3640 — C.4
1.3605 B.171 C.17 1.3623 B.189 C.17 1 .3641 — C.5
1.3606 B.172 C.17 1.3624 B.190 C.17 1 .3642 — C.6
1.3607 B.173 C.17 1.3625 B.191 C.17 1 .3643 — C.7
1.3608 B.174 C.17 1.3626 B.192 C.17 1 .3644 — C.8
1.3609 B.175 C.17 1.3627 B.193 C.17 1 .3645 — C.9
1.3610 B.176 C.17 1.3628 B.194 C.17 1 .3646 — C.10
1.361 1 B.177 C.17 1.3629 B.195 C.17 1 .3647 — C.1 1
1.3612 B.178 C.17 1.3630 B.196 C.17 1 .3648 — C.12
1.3613 B.179 C.17 1.3631 B.197 C.17 1 .3649 — C.13
1.3614 B.180 C.17 1.3632 B.198 C.17 1 .3650 — C.14
1.3615 B.181 C.17 1.3633 B.199 C.17 1 .3651 — C.15
1.3616 B.182 C.17 1.3634 B.200 C.17 1 .3652 — C.16
1.3617 B.183 C.17 1.3635 B.201 C.17 1 .3653 — C.17
1.3618 B.184 C.17 1.3636 B.202 C.17
The specific number for each single composition is deductible as follows:
Composition 1 .203 e.g. comprises the compound (1.1 .1-25), clethodim (B.1 ) and benoxacor (C.1 ) (see table B, entry B.1 and table C, entry C.1 ).
Also especially preferred are compositions 2.1 to 2.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they comprise the compound (1.3.1-4) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 3.1 to 3.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.2 as further herbicide B. Also especially preferred are compositions 4.1 to 4.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.8 as further herbicide B.
Also especially preferred are compositions 5.1 to 5.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.30 as further herbicide B. Also especially preferred are compositions 6.1 to 6.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.32 as further herbicide B.
Also especially preferred are compositions 7.1 to 7.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.35 as further herbicide B. Also especially preferred are compositions 8.1 to 8.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.38 as further herbicide B. Also especially preferred are compositions 9.1 to 9.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.40 as further herbicide B.
Also especially preferred are compositions 10.1 to 10.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.51 as further herbicide B. Also especially preferred are compositions 1 1.1 to 1 1 .3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.55 as further herbicide B.
Also especially preferred are compositions 12.1 to 12.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.56 as further herbicide B.
Also especially preferred are compositions 13.1 to 13.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.64 as further herbicide B.
Also especially preferred are compositions 14.1 to 14.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.66 as further herbicide B.
Also especially preferred are compositions 15.1 to 15.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.67 as further herbicide B.
Also especially preferred are compositions 16.1 to 16.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.68 as further herbicide B.
Also especially preferred are compositions 17.1 to 17.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.69 as further herbicide B.
Also especially preferred are compositions 18.1 to 18.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.73 as further herbicide B.
Also especially preferred are compositions 19.1 to 19.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.76 as further herbicide B.
Also especially preferred are compositions 20.1 to 20.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.81 as further herbicide B.
Also especially preferred are compositions 21.1 to 21.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.82 as further herbicide B.
Also especially preferred are compositions 22.1 to 22.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.85 as further herbicide B.
Also especially preferred are compositions 23.1 to 23.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.88 as further herbicide B.
Also especially preferred are compositions 24.1 to 24.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.89 as further herbicide B.
Also especially preferred are compositions 25.1 to 25.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.94 as further herbicide B.
Also especially preferred are compositions 26.1 to 26.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.95 as further herbicide B.
Also especially preferred are compositions 27.1 to 27.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.98 as further herbicide B.
Also especially preferred are compositions 28.1 to 28.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.100 as further herbicide B.
Also especially preferred are compositions 29.1 to 29.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.103 as further herbicide B.
Also especially preferred are compositions 30.1 to 30.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.103 and B.67 as further herbicides B.
Also especially preferred are compositions 31.1 to 31 .3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.103 and B.76 as further herbicides B.
Also especially preferred are compositions 32.1 to 32.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.103 and B.82 as further herbicides B.
Also especially preferred are compositions 33.1 to 33.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.104 as further herbicide B.
Also especially preferred are compositions 34.1 to 34.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.104 and B.67 as further herbicides B.
Also especially preferred are compositions 35.1 to 35.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.104 and B.76 as further herbicides B.
Also especially preferred are compositions 36.1 to 36.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.104 and B.82 as further herbicides B.
Also especially preferred are compositions 37.1 to 37.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.106 as further herbicide B.
Also especially preferred are compositions 38.1 to 38.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.107 as further herbicide B.
Also especially preferred are compositions 39.1 to 39.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B. 107 and B.67 as further herbicides B. Also especially preferred are compositions 40.1 to 40.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B. 107 and B.76 as further herbicides B.
Also especially preferred are compositions 41.1 to 41 .3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B. 107 and B.82 as further herbicides B.
Also especially preferred are compositions 42.1 to 42.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.109 as further herbicide B.
Also especially preferred are compositions 43.1 to 43.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 1 1 as further herbicide B.
Also especially preferred are compositions 44.1 to 44.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 1 1 and B.67 as further herbicides B.
Also especially preferred are compositions 45.1 to 45.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 1 1 and B.76 as further herbicides B.
Also especially preferred are compositions 46.1 to 46.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 1 1 and B.82 as further herbicides B.
Also especially preferred are compositions 47.1 to 47.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B. 1 16 as further herbicide B.
Also especially preferred are compositions 48.1 to 48.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 16 and B.67 as further herbicides B.
Also especially preferred are compositions 49.1 to 49.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 16 and B.94 as further herbicides B.
Also especially preferred are compositions 50.1 to 50.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 16 and B.103 as further herbicides B.
Also especially preferred are compositions 51.1 to 51.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 16 and B.128 as further herbicides B.
Also especially preferred are compositions 52.1 to 52.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 16 and B.104 as further herbicides B.
Also especially preferred are compositions 53.1 to 53.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 16 and B.107 as further herbicides B.
Also especially preferred are compositions 54.1 to 54.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.1 16 and B.1 1 1 as further herbicides B.
Also especially preferred are compositions 55.1 to 55.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.122 as further herbicide B.
Also especially preferred are compositions 56.1 to 56.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.126 as further herbicide B.
Also especially preferred are compositions 57.1 to 57.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.128 as further herbicide B.
Also especially preferred are compositions 58.1 to 58.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.131 as further herbicide B.
Also especially preferred are compositions 59.1 to 59.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.132 as further herbicide B.
Also especially preferred are compositions 60.1 to 60.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.133 as further herbicide B.
Also especially preferred are compositions 61.1 to 61.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.135 as further herbicide B.
Also especially preferred are compositions 62.1 to 62.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.137 as further herbicide B.
Also especially preferred are compositions 63.1 to 63.3653 which differ from the corresponding compositions 1 1 .1 to 1 .3653 only in that they additionally comprise B.138 as further herbicide B.
Also especially preferred are compositions 64.1 to 64.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.140 as further herbicide B.
Also especially preferred are compositions 65.1 to 65.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.145 as further herbicide B.
Also especially preferred are compositions 66.1 to 66.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.153 as further herbicide B.
Also especially preferred are compositions 67.1 to 67.3653 which differ from the correspond- ing compositions 1.1 to 1 .3653 only in that they additionally comprise B.156 as further herbicide B.
Also especially preferred are compositions 68.1 to 68.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.171 as further herbicide B. Also especially preferred are compositions 69.1 to 69.3653 which differ from the corresponding compositions 1.1 to 1 .3653 only in that they additionally comprise B.174 as further herbicide B.
Also especially preferred are compositions 70.1 to 70.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-10) in place of the compound (1.3.1-3).
Also especially preferred are compositions 71.1 to 71 .3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-1 1 ) in place of the compound (1.3.1-3).
Also especially preferred are compositions 72.1 to 72.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-17) in place of the compound (1.3.1-3).
Also especially preferred are compositions 73.1 to 73.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-18) in place of the compound (1.3.1-3).
Also especially preferred are compositions 74.1 to 74.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-24) in place of the compound (1.3.1-3).
Also especially preferred are compositions 75.1 to 75.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-25) in place of the compound (1.3.1-3).
Also especially preferred are compositions 76.1 to 76.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-31 ) in place of the compound (1.3.1-3).
Also especially preferred are compositions 77.1 to 77.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-32) in place of the compound (1.3.1-3).
Also especially preferred are compositions 78.1 to 78.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-38) in place of the compound (1.3.1-3).
Also especially preferred are compositions 79.1 to 79.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-39) in place of the compound (1.3.1-3).
Also especially preferred are compositions 80.1 to 80.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-45) in place of the compound (1.3.1-3).
Also especially preferred are compositions 81.1 to 81 .3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-46) in place of the compound (1.3.1-3).
Also especially preferred are compositions 82.1 to 82.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-52) in place of the compound (1.3.1-3).
Also especially preferred are compositions 83.1 to 83.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-53) in place of the compound (1.3.1-3).
Also especially preferred are compositions 84.1 to 84.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-59) in place of the compound (1.3.1-3).
Also especially preferred are compositions 85.1 to 85.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-60) in place of the compound (1.3.1-3).
Also especially preferred are compositions 86.1 to 86.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-66) in place of the compound (1.3.1-3).
Also especially preferred are compositions 87.1 to 87.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .3.1-67) in place of the compound (1.3.1-3).
Also especially preferred are compositions 88.1 to 88.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1 .15.1-3) in place of the compound (1.3.1-3).
Also especially preferred are compositions 89.1 to 89.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .15.1-4) in place of the compound (1.3.1-3).
Also especially preferred are compositions 90.1 to 90.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-10) in place of the compound (1.3.1-3).
Also especially preferred are compositions 91.1 to 91.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-1 1 ) in place of the compound (1.3.1-3).
Also especially preferred are compositions 92.1 to 92.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-17) in place of the compound (1.3.1-3).
Also especially preferred are compositions 93.1 to 93.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-24) in place of the compound (1.3.1-3).
Also especially preferred are compositions 94.1 to 94.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-25) in place of the compound (1.3.1-3).
Also especially preferred are compositions 95.1 to 95.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-31 ) in place of the compound (1.3.1-3).
Also especially preferred are compositions 96.1 to 96.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-32) in place of the compound (1.3.1-3).
Also especially preferred are compositions 97.1 to 97.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-38) in place of the compound (1.3.1-3). Also especially preferred are compositions 98.1 to 98.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-39) in place of the compound (1.3.1-3).
Also especially preferred are compositions 99.1 to 99.3653 which differ from the correspond- ing compositions 1.1 to 1.3653 only in that they comprise the compound (1.15.1-45) in place of the compound (1.3.1-3).
Also especially preferred are compositions 100.1 to 100.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.15.1-46) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 101 .1 to 101.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.15.1-52) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 102.1 to 102.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.15.1-53) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 103.1 to 103.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.15.1-59) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 104.1 to 104.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.15.1-60) in place of the compound (1.3.1-3).
Also especially preferred are compositions 105.1 to 105.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.15.1-66) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 106.1 to 106.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .15.1-67) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 107.1 to 107.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.16.1-3) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 108.1 to 108.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.16.1-4) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 109.1 to 109.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.16.1-10) in place of the compound (1.3.1-3).
Also especially preferred are compositions 1 10.1 to 1 10.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.16.1-1 1 ) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 1 1 1 .1 to 1 1 1.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.16.1-17) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 1 12.1 to 1 12.3653 which differ from the corresponding compositions 1 .1 to 1.3653 only in that they comprise the compound (1.16.1-18) in place of the compound (1.3.1-3).
Also especially preferred are compositions 1 13. to 1 13.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-24) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 1 14. to 1 14.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-25) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 1 15. to 1 15.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-31 ) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 1 16. to 1 16.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-32) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 1 17. to 1 17.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-38) in place of the compound (1.3.1-3).
Also especially preferred are compositions 1 18. to 1 18.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-39) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 1 19. to 1 19.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-45) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 120. to 120.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-46) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 121 . to 121 .3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-52) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 122. to 122.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-53) in place of the compound (1.3.1-3).
Also especially preferred are compositions 123. to 123.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-59) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 124. to 124.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-60) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 125. to 125.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-66) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 126. to 126.3653 which differ from the corre- sponding compositions 1 .1 to 1.3653 only in that hey comprise the compound (1.16.1-67) in place of the compound (1 .3.1-3).
Also especially preferred are compositions 127.1 to 127.3653 which differ from the corresponding compositions 1.1 to 1.3653 only in that they comprise the compound (1 .15.1-18) in place of the compound (1 .3.1-3).
The invention also relates to agrochemical compositions comprising at least an auxiliary and at least one pyridine compound of formula (I) according to the invention.
An agrochemical composition comprises a pesticidal effective amount of a pyridine compound of formula (I). The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling unwanted plants, especially for controlling unwanted plants in cultivated plants and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the plants to be controlled, the treated cultivated plant or material, the climatic conditions and the specific pyridine compound pyridine compound of formula (I) used.
The pyridine compound pyridine compounds of formula (I), their N-oxides, salts or derivatives can be converted into customary types of agrochemical compositions, e. g. solutions, emul- sions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for agrochemical composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), pressings (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e.g. GF). These and further agrochemical compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, disper- sants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibil- izers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, al- kylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime- stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof. Suitable surfactants are surface-active compounds, such as anionic, cationic, non-ionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & De- tergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl- sulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty ac- ids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose, and glucose esters, or al- kylpoly-glucosides. Examples of polymeric surfactants are home- or copolymers of vinylpyrroli- done, vinylalcohols, or vinylacetate.
Suitable cationic surfactants are quaternary surfactants, e.g. quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyeth- yleneamines.
Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the pyridine compound pyridine compounds of formula (I) on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants, and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea, and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e.g. in red, blue, or green) are pigments of low water solubility and water- soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo-, and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for agrochemical composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a pyridine compound pyridine compound of formula (I) according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water- soluble solvent (e.g. alcohols) ad 100 wt%. The active substance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a pyridine compound pyridine compound of formula (I) according to the invention and 1-10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in organic solvent (e.g. cyclo- hexanone) ad 100 wt%. Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a pyridine compound pyridine compound of formula (I) according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion.
iv) Emulsions (EW, EO, ES)
5-40 wt% of a pyridine compound pyridine compound of formula (I) according to the invention and 1-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mix- ture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion.
v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a pyridine compound pyridine compound of formula (I) according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1 -2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e.g. polyvinylalcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a pyridine compound pyridine compound of formula (I) according to the invention are ground finely with addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a pyridine compound pyridine compound of formula (I) according to the invention are ground in a rotor-stator mill with addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and solid carrier (e.g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance. viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a pyridine compound pyridine compound of formula (I) according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lig- nosulfonate), 1 -5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
iv) Microemulsion (ME)
5-20 wt% of a pyridine compound pyridine compound of formula (I) according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexa- none), 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
iv) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a pyridine compound pyridine compound of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid, and a di- or tri- acrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radical initiator results in the formation of poly(meth)acry- late microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a pyridine compound pyr- idine compound of formula (I) according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4'-diiso- cyanate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 -10 wt%. The wt% relate to the total CS composi- tion.
ix) Dustable powders (DP, DS)
1-10 wt% of a pyridine compound pyridine compound of formula (I) according to the invention are ground finely and mixed intimately with solid carrier (e.g. finely divided kaolin) ad 100 wt%. x) Granules (GR, FG)
0.5-30 wt% of a pyridine compound pyridine compound of formula (I) according to the invention is ground finely and associated with solid carrier (e.g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or the fluidized bed.
xi) Ultra-low volume liquids (UL)
1-50 wt% of a pyridine compound pyridine compound of formula (I) according to the invention are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%.
The agrochemical compositions types i) to xi) may optionally comprise further auxiliaries, such as 0,1-1 wt% bactericides, 5-15 wt% anti-freezing agents, 0,1 -1 wt% anti-foaming agents, and 0,1-1 wt% colorants.
The agrochemical compositions comprising generally comprise between 0.01 and 95%, prefer- ably between 0.1 and 90%, and in particular between 0.5 and 75%, by weight of the pyridine compound pyridine compound of formula (I). The pyridine compound pyridine compounds of formula (I) are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
Solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds. The agrochemi- cal compositions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40% by weight, in the ready-to-use preparations. Application can be carried out before or during sowing.
Methods for applying pyridine compound pyridine compounds of formula (I) and agrochemical compositions thereof, on to plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, pyridine compounds of formula (I) and agrochemical compositions thereof, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners) may be added to the pyri- dine compounds of formula (I) and the agrochemical compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the agrochemical compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1 .
The user applies the pyridine compound of formula (I) according to the invention and the agro- chemical compositions comprising them usually from a pre-dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g. components comprising pyridine compounds of formula (I) may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
In a further embodiment, individual components of the agrochemical composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
In a further embodiment, either individual components of the agrochemical composition according to the invention or partially premixed components, e. g components comprising pyridine compounds of formula (I) can be applied jointly (e.g. after tank mix) or consecutively.
The pyridine compounds of formula (I), are suitable as herbicides. They are suitable as such or as an appropriately formulated composition (agrochemical composition).
The pyridine compounds of formula (I), or the agrochemical compositions comprising the pyridine compounds of formula (I), control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and grass weeds in crops such as wheat, rice, maize, soya, and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
The pyridine compounds of formula (I), or the agrochemical compositions comprising them, are applied to the plants mainly by spraying the leaves. Here, the application can be carried out using, e.g., water as carrier by customary spraying techniques using spray liquor amounts of from about 100 to 1000 l/ha (e.g. from 300 to 400 l/ha). The pyridine compounds of formula (I), or the agrochemical compositions comprising them, may also be applied by the low-volume or the ultra-low-volume method, or in the form of micro granules.
Application of the pyridine compounds of formula (I), or the agrochemical compositions comprising them, can be done before, during, and/or after, preferably during and/or after, the emergence of the undesirable plants.
The pyridine compounds of formula (I), or the agrochemical compositions comprising them, can be applied pre-, post-emergence or pre-plant, or together with the seed of a crop plant. It is also possible to apply the pyridine compounds of formula (I), or the agrochemical compositions comprising them, by applying seed, pretreated with the pyridine compounds of formula (I), or the agrochemical compositions comprising them, of a crop plant. If the active ingredients are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that as far as possible they do not come into contact with the leaves of the sensitive crop plants, while the active ingredients reach the leaves of undesirable plants growing underneath, or the bare soil surface (post-directed, lay-by).
In a further embodiment, the pyridine compounds of formula (I), or the agrochemical compositions comprising them, can be applied by treating seed. The treatment of seeds comprises essentially all procedures familiar to the person skilled in the art (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the pyridine compounds of formula (I), or the agrochemical compositions prepared therefrom. Here, the herbicidal compositions can be applied diluted or undiluted.
The term "seed" comprises seed of all types, such as, e.g., corns, seeds, fruits, tubers, seedlings and similar forms. Here, preferably, the term seed describes corns and seeds. The seed used can be seed of the useful plants mentioned above, but also the seed of transgenic plants or plants obtained by customary breeding methods.
When employed in plant protection, the amounts of active substances applied, i.e. the pyridine compounds of formula (I) without formulation auxiliaries, are, depending on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and in particular from 0.1 to 0.75 kg per ha.
In another embodiment of the invention, the application rate of the pyridine compounds of formula (I) is from 0.001 to 3 kg/ha, preferably from 0.005 to 2.5 kg/ha and in particular from 0.01 to 2 kg/ha of active substance (a.s.).
In another preferred embodiment of the invention, the rates of application of the pyridine compounds of formula (I) according to the present invention (total amount of pyridine
compounds of formula (I)) are from 0.1 g/ha to 3000 g/ha, preferably 10 g/ha to 1000 g/ha, depending on the control target, the season, the target plants and the growth stage.
In another preferred embodiment of the invention, the application rates of the pyridine compounds of formula (I) are in the range from 0.1 g/ha to 5000 g/ha and preferably in the range from 1 g/ha to 2500 g/ha or from 5 g/ha to 2000 g/ha. In another preferred embodiment of the invention, the application rate of the pyridine compounds of formula (I) is 0.1 to 1000 g/ha, preferablyl to 750 g/ha, more preferably 5 to 500 g/ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drench- ing seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g, and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
In another embodiment of the invention, to treat the seed, the amounts of active substances applied, i.e. the pyridine compounds of formula (I) are generally employed in amounts of from 0.001 to 10 kg per 100 kg of seed.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Depending on the application method in question, the pyridine compounds of formula (I), or the agrochemical compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable crops are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec, altissima, Beta vulgaris spec, rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum,
Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, and Zea mays.
Preferred crops are Arachis hypogaea, Beta vulgaris spec, altissima, Brassica napus var. napus, Brassica oleracea, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora,
Coffea liberica), Cynodon dactylon, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hordeum vulgare, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Medicago sativa, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa , Phaseolus lunatus, Phaseolus vulgaris, Pistacia vera, Pisum sativum, Prunus dulcis, Saccharum officinarum,
Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Triticale, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, and Zea mays.
Especially preferred crops are crops of cereals, corn, soybeans, rice, oilseed rape, cotton, potatoes, peanuts, or permanent crops. The pyridine compounds of formula (I) according to the invention, or the agrochemical compositions comprising them, can also be used in genetically modified plants. The term "genetically modified plants" is to be understood as plants whose genetic material has been modified by the use of recombinant DNA techniques to include an inserted sequence of DNA that is not native to that plant species' genome or to exhibit a deletion of DNA that was native to that species' genome, wherein the modification(s) cannot readily be obtained by cross breeding, mutagenesis or natural recombination alone. Often, a particular genetically modified plant will be one that has obtained its genetic modification(s) by inheritance through a natural breeding or propagation process from an ancestral plant whose genome was the one directly treated by use of a recom- binant DNA technique. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides, e. g., by inclusion therein of amino acid mutation(s) that permit, decrease, or promote glycosylation or polymer additions such as prenylation, acetylation farnesylation, or PEG moiety attachment.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e.g. have been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxyphenylpyruvate dioxygen- ase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) in- hibitors such as sulfonyl ureas or imidazolinones; enolpyruvyl shikimate 3-phosphate synthase (EPSP) inhibitors such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering; furthermore, plants have been made re- sistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are, e.g., described in Pest Management Science 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Science 57, 2009, 108; Australian Journal of Agricultural Research 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by mutagenesis and conventional methods of breeding, e. g., Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g., ima- zamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g., tribe- nuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate, imidazolinones, and glufosinate, some of which are under development or commercially available under the brands or trade names RoundupReady® (glyphosate tolerant, Monsanto, USA), Cultivance® (imidazolinone tolerant, BASF SE, Germany), and LibertyLink® (glufosinate tolerant, Bayer CropScience, Germany).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as delta-endotoxins, e. g., CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g., VIP1 , VIP2, VIP3, or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g., Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins pro- duced by fungi, such as Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cys- tatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxy-steroid oxidase, ec- dysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-re- ductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as including pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combina- tion of protein domains, (see, e. g., WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810, and WO
03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g., in the publications mentioned above.
These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coeloptera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), Yield- Gard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme Phosphinothricin-N-Acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protecta®, Bt1 1 (e. g., Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enzyme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cryl F toxin and PAT enzyme).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques ca- pable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "pathogene- sis-related proteins" (PR proteins, see, e.g., EP-A 392 225), plant disease resistance genes (e. g., potato culti-vars, which express resistance genes acting against Phytophthora infestans de- rived from the Mexican wild potato, Solanum bulbocastanum) or T4-lyso-zym (e.g., potato culti- vars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylovora). The methods for producing such genetically modi-fied plants are generally known to the person skilled in the art and are described, e.g., in the publications mentioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g., bio-mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve human or animal nutrition, e. g., oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g., Nexera® rape, Dow AgroSciences, Canada).
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of ingredients or new ingredients, specifically to improve raw material production, e.g., potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato, BASF SE, Germany).

Claims

Claims
1 . The pyridine compounds of formula (I)
Figure imgf000128_0001
wherein
the dotted line ( ) is a single bond or a double bond;
R1 is Ci-C6-alkyl, Ci-C6-haloalkyl, hydroxy-CrC6-alkyl, C2-C6-alkenyl, C2-C6-haloal- kenyl, C2-C6-alkynyl, C3-C6-haloalkynyl, Ci-C6-alkoxy-CrC6-alkyl, Ci-C6-alkoxy, C3- C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkynyloxy, C3-C6-haloalkynyloxy, C1-C6 haloalkoxy, C3-C6-cycloalkoxy, C3-C6-halocycloalkoxy, C3-C6-cycloalkenyloxy, C3-C6 halocycloalkenyloxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, (Ci-C6-alkyl)amino, di(Ci- C6-alkyl)amino, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, C3-C6-cycloalkyl, C3-C6-cyclo alkenyl, C3-C6-halocycloalkyl, C3-C6-halocycloalkenyl, [1 -(Ci-C6-alkyl)]-C3-C6-cycloal kyl, [1 -(C2-C6-alkenyl)]-C3-C6-cycloalkyl, [1 -(C2-C6-alkynyl)]-C3-C6-cycloalkyl, [1 -(Ci- C6-haloalkyl)]-C3-C6-cycloalkyl, [1 -(C2-C6-haloalkenyl)]-C3-C6-cycloalkyl, [1 -(C3-C6- haloalkynyl)]-C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, C3-C6-cycloalkyl-Ci-C6- haloalkyl, C3-C6-cycloalkyl-Ci-C6-alkoxy, C3-C6-cycloalkyl-Ci-C6-haloalkoxy, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein the cyclic groups of R1 are unsubstituted or substituted by Ra;
R2 is d-Ce-alkyl, d-Ce-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy-C2-C6 alkenyl, Ci-C6-alkoxy-C2-C6-haloalkenyl, Ci-C6-haloalkoxy-C2-C6-alkenyl, C1-C6- haloalkoxy-C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, Ci-C6-alkoxy-C2-C6- alkynyl, CrC6-alkoxy-C3-C6-haloalkynyl, Ci-C6-haloalkoxy-C2-C6-alkynyl, C1-C6- haloalkoxy-C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, Cs-Ce-cycloalkenyl, C3-C6-halocycloalkenyl, C3-C6-cycloalkyl- Ci-C6-alkyl, C3-C6-cycloalkyl- C1-C6- haloalkyl, C3-C6-halocycloalkyl- Ci-C6-alkyl, C3-C6-halocycloalkyl-Ci-C6-haloalkyl, C3-C6-cycloalkenyl- Ci-C6-alkyl, C3-C6-cycloalkenyl-Ci-C6-haloalkyl, C3-C6-halocyclo alkenyl- Ci-C6-alkyl, C3-C6-halocycloalkenyl- Ci-C6-haloalkyl, C3-C6-cycloalkyl- C2- C6-alkenyl, C3-C6-cycloalkyl- C2-C6-haloalkenyl, C3-C6-halocycloalkyl- C2-C6-alkenyl, C3-C6-halocycloalkyl- C2-C6-haloalkenyl, C3-C6-cycloalkenyl- C2-C6-alkenyl, Cs-Ce- cycloalkenyl- C2-C6-haloalkenyl, C3-C6-halocycloalkenyl- C2-C6-alkenyl, Cs-Ce-halocycloalkenyl- C2-C6-haloalkenyl, C3-C6-cycloalkyl- C2-C6-alkynyl, C3-C6-cycloalkyl-C3 C6-haloalkynyl, C3-C6-halocycloalkyl-C2-C6-alkynyl, C3-C6-halocycloalkyl-C3-C6- haloalkynyl, C3-C6-cycloalkenyl-C2-C6-alkynyl, C3-C6-cycloalkenyl-C3-C6-haloalkynyl, C3-C6-halocycloalkenyl-C2-C6-alkynyl, C3-C6-halocycloalkenyl-C3-C6-haloalkynyl, C3- C6-cycloalkyl-Ci-C6-alkylidenyl, C3-C6-cycloalkyl-C2-C6-haloalkylidenyl, C3-C6-halocy cloalkyl-Ci-Ce-alkylidenyl, C3-C6-halocycloalkyl-C2-C6-haloalkylidenyl, C3-C6-cycloal- kenyl-Ci-C6-alkylidenyl, C3-C6-cycloalkenyl-C2-C6-haloalkylidenyl, C3-C6-halocycloal- kenyl-Ci-C6-alkylidenyl, C3-C6-halocycloalkenyl-C2-C6-haloalkylidenyl, heterocyclyl- Ci-C6-alkylidenyl, heterocyclyl-Ci-C6- aloalkylidenyl, C3-C6-hydroxycycloalkyl-Ci-C6 alkyl, C3-C6- ydroxycycloalkyl-Ci-C6- aloalkyl, C3-C6-hydroxycycloalkenyl-Ci-C6-al- kyl, C3-C6- ydroxycycloalkenyl-Ci-C6- aloalkyl, Ci-C6- ydroxyalkyl, C2-C6-hydroxy- haloalkyl, C3-C6- ydroxyalkenyl, C3-C6- ydroxyhaloalkenyl, C3-C6- ydroxyalkynyl, C4-C6- ydroxyhaloalkynyl, C3-C6- ydroxycycloalkyl, C3-C6- ydroxyhalocycloalkyl, C3-C6- ydroxycycloalkenyl, C3-C6-hydroxyhalocycloalkenyl, C3-C6-cycloalkyl-Ci-C6- hydroxyalkyl, C3-C6-cycloalkyl-C2-C6- ydroxyhaloalkyl, C3-C6-halocycloalkyl-Ci-C6- hydroxyalkyl, C3-C6- alocycloalkyl-C2-C6- ydroxyhaloalkyl, C3-C6-cycloalkenyl-Cr C6- ydroxyalkyl, C3-C6-cycloalkenyl-C2-C6- ydroxyhaloalkyl, C3-C6-halocycloalkenyl Ci-C6- ydroxyalkylC3-C6- alocycloalkenyl-C2-C6- ydroxyhaloalkyl, C3-C6-cycloalkyl- C3-C6- ydroxyalkenyl, C3-C6-cycloalkyl-C3-C6- ydroxyhaloalkenyl, C3-C6-halocyclo- alkyl-C3-C6-hydroxyalkenyl, C3-C6- alocycloalkyl-C3-C6- ydroxyhaloalkenyl, C3-C6- cycloalkenyl-C3-C6-hydroxyalkenyl, C3-C6-cycloalkenyl-C3-C6- ydroxyhaloalkenyl, C3-C6- alocycloalkenyl-C3-C6-hydroxyalkenyl, C3-C6-halocycloalkenyl-C3-C6-hydrox- yhaloalkenyl, C3-C6-cycloalkyl-C3-C6- ydroxyalkynyl, C3-C6-halocycloalkyl-C3-C6-hy- droxyalkynyl, C3-C6-cycloalkenyl-C3-C6- ydroxyalkynyl, C3-C6-halocycloalkenyl-C3- C6- ydroxyalkynyl, C3-C6-cycloalkyl-C2-C6-hydroxyalkylidenyl, C3-C6-halocycloalkyl- C2-C6- ydroxyalkylidenyl, C3-C6-cycloalkenyl-C2-C6- ydroxyalkylidenyl, C3-C6-halo- cycloalkyl-C2-C6- ydroxyalkylidenyl, heterocyclyl-C2-C6-hydroxyalkylidenyl, hy- droxycarbonyl-Ci-C6- ydroxyalkyl, hydroxycarbonyl-Ci-C6-alkyl, hydroxycarbonyl- Ci-C6- aloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6- ydroxyalkyl, Ci-C6-haloalkoxycar- bonyl-Ci-C6- ydroxyalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloal- koxycarbonyl-CrC6- aloalkyl, Ci-C6-alkoxycarbonyl-CrC6-alkyl, Ci-C6-haloal- koxycarbonyl-CrC6-alkyl, C3-C6- ydroxycycloalkyl-Ci-C6- ydroxyalkyl, C3-C6- y- droxycycloalkenyl-Ci-C6- ydroxyalkyl, C3-C6- ydroxycycloalkyl-C3-C6- ydroxy- alkenyl, C3-C6- ydroxycycloalkenyl-C3-C6-hydroxyalkenyl, C3-C6- ydroxycycloalkyl- C3-C6- ydroxyalkynyl, C3-C6-hydroxycycloalkenyl-C3-C6- ydroxyalkenyl, C2-C6-dihy- droxyalkyl, C3-C6-dihydroxyhaloalkyl, C4-C6-dihydroxyalkenyl, C4-C6-dihydroxy- haloalkenyl, C4-C6-dihydroxyalkynyl, Cs-Ce-dihydroxyhaloalkynyl, C4-C6-dihydroxycy cloalkyl, C4-C6-dihydroxyhalocycloalkyl, C4-C6-dihydroxycycloalkenyl, C4-C6-dihy- droxyhalocycloalkenyl, C3-C6-cycloalkyl-C2-C6-dihydroxyalkyl, C3-C6-halocycloalkyl- C2-C6-dihydroxyalkyl, C3-C6-cycloalkenyl-C2-C6-dihydroxyalkyl, C3-C6-halocycloal- kenyl-C2-C6-dihydroxyalkyl, C3-C6-cycloalkyl-C3-C6-dihydroxyalkenyl, C3-C6-halocy- cloalkyl-C3-C6-dihydroxyalkenyl, C3-C6-cycloalkenyl-C3-C6-dihydroxyalkenyl, C3-C6- halocycloalkenyl-C3-C6-dihydroxyalkenyl, C3-C6-cycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-halocycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-cycloalkenyl-C4-C6-dihydroxy- alkynyl, C3-C6-halocycloalkyl-C4-C6-dihydroxyalkynyl, C3-C6-cycloalkyl-C3-C6-dihy- droxyalkylidenyl, C3-C6-halocycloalkyl-C3-C6-dihydroxyalkylidenyl, heterocyclyl-C3- C6-dihydroxyalkylidenyl, hydroxycarbonyl-C2-C6-dihydroxyalkyl, hydroxycarbonyl-C3- C6-dihydroxyhaloalkyl, Ci-C6-alkoxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-haloal- koxycarbonyl-C2-C6-dihydroxyalkyl, Ci-C6-haloalkoxycarbonyl-C3-C6-dihydroxy- haloalkyl, C3-C6-dihydroxycycloalkyl- Ci-C6-alkyl, C3-C6-dihydroxycycloalkyl- C1-C6- haloalkylC3-C6-dihydroxycycloalkyl- C2-C6-alkenyl, C3-C6-dihydroxycycloalkyl- C2-C6- haloalkenyl, C3-C6-dihydroxycycloalkyl- C2-C6-alkynyl, C3-C6-dihydroxycycloalkyl- C3-C6- aloalkynyl, Ci-C6-alkylcarbonyl-CrC6-alkyl, d-drhaloalkylcarbonyl-d-dr alkyl, Ci-C6-alkylcarbonyl-Ci-C6- aloalkyl, Ci-C6- aloalkylcarbonyl-Ci-C6- aloalkyl, hydroxycarbonyl-C2-C6-alkenyl, hydroxycarbonyl-C2-C6-haloalkenyl, d-dralkoxy- carbonyl-C2-C6-alkenyl, Ci-C6- aloalkoxycarbonyl-C2-C6-alkenyl, Ci-C6-alkoxycar- bonyl-C2-C6- aloalkenyl, Ci-C6- aloalkoxycarbonyl-C2-C6- aloalkenyl, hydroxycar- bonyl-C2-C6-alkynyl, hydroxycarbonyl-C3-C6- aloalkynyl, d-Gralkoxycarbonyl-d- C6-alkynyl, Ci-C6-haloalkoxycarbonyl-C2-C6-alkynyl, Ci-C6-alkoxycarbonyl-C3-C6- haloalkynyl, CrC6-haloalkoxycarbonyl-C3-C6- aloalkynyl, Ci-C6-cyanoalkyl, C2-C6- cyanohaloalkyl, Ci-C6-dicyanoalkyl, C2-C6-dicyanohaloalkyl, di(hydroxycarbonyl)-d- C6-alkyl, di(hydroxycarbonyl)-Ci-C6-haloalkyl, di(Ci-C6-alkoxycarbonyl)-Ci-C6-alkyl, di(Ci-C6- aloalkoxycarbonyl)-Ci-C6-alkyl, di(Ci-C6-alkoxycarbonyl)-Ci-C6- aloalkyl, di(Ci-C6- aloalkoxycarbonyl)-Ci-C6- aloalkyl, di(d-C6-alkoxyl)phosphoryl-d-C6- alkyl, di(Ci-C6-haloalkoxyl)phosphoryl-Ci-C6-alkyl, di(d-C6-alkoxyl)phosphoryl-d- C6- aloalkyl, di(Ci-C6- aloalkoxyl)phosphoryl-Ci-C6- aloalkyl, phosphoryl-d-dral- kyl , phosphoryl-Ci-C6- aloalkyl , di[di(Ci-C6-alkoxyl)phosphoryl-)]Ci-C6-alkyl, di[di(Ci-C6- aloalkoxyl)phosphoryl-)]CrC6-alkyl, di[di(d-C6-alkoxyl)phosphoryl-)]d- C6- aloalkyl, di[di(CrC6- aloalkoxyl)phosphoryl-)]Ci-C6- aloalkyl, diphosphoryl-d- C6-alkyl , diphosphoryl-Ci-C6- aloalkyl, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-haloal- kylthio-Ci-Ce-alkyl, Ci-C6-alkylthio-Ci-C6- aloalkyl, d-C6-haloalkylthio-d-C6-haloal- kyl, Ci-C6-alkylsulfinly-Ci-C6-alkyl, Ci-C6- aloalkylsulfinly-Ci-C6-alkyl, d-C6-alkyl- sulfinly-Ci-Ce-haloalkyl, Ci-C6-haloalkylsulfinly-Ci-C6-haloalkyl, Ci-C6-alkylsulfonyl- Ci-C6-alkyl, Ci-C6-haloalkylsulfonyl-Ci-C6-alkyl, d-drhaloalkylsulfonyl-d-Ce- haloalkyl, phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein hydroxy groups of R2 are unsubstituted or substituted by Rb;
cyclic groups of R2 are unsubstituted or substituted by Rc; and
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd;
Rb is d-Ce-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3- C6-halocycloalkenyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-drhaloalkoxycarbonyl- Ci-C6-alkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci- C6-haloalkyl, CrC6-alkylcarbonyl, CrC6-haloalkylcarbonyl, hydroxycarbonyl-Ci- C6-alkyl, hydroxycarbonyl-CrC6-haloalkyl, Ci-C6-alkyloxycarbonyl, Ci-C6-haloal- kyloxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-haloalkylthiocarbonyl, Ci-di-alkyl- aminocarbonyl, Ci-C6-haloalkylaminocarbonyl, Ci-C6-dialkylaminocarbonyl, Ci- C6-dihaloalkylaminocarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C1-C6- alkoxy-Ci-C6-alkyl, Ci-C6-haloalkoxy-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-haloalkyl, Ci-C6-haloalkoxy-Ci-C6-haloalkyl, phenyl-Ci-C6-alkyl, or phenyl-Ci-C6-haloalkyl; Rc is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci-
C6-haloalkoxy, Ci-C6-alkylthio, d-di-alkylsulfinyl, or Ci-C6-alkylsulfonyl;
Rd is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein the substituent Rd is unsubstituted or substituted by Re;
Re is halogen, CN, NO2, d-Ce-alkyl, d-Ce-haloalkyl, hydroxy, Ci-Ce-alkoxy or Ci- drhaloalkoxy, Ci-C6-alkylsulfonyl;
is a 9 or 10 membered bicyclic ring comprising A; A is C*, CR3, NR3A, N, O, or S;
C* is a bridge carbon of the bicyclic ring Z;
R3 is halogen, CN, CHO, N02, Ci-Ce-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6- haloalkenyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R3 are unsubstituted or substituted by substituents Ra;
R3A is H, Ci-Ce-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6-alkenyl, C2-C6-haloal- kenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, Ci-C6-haloalkoxy, C3-C6- alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C1-C6- alkoxy-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R3A are unsubstituted or substituted by Ra;
R4 is halogen, CN, CHO, N02, Ci-Ce-alkyl, Ci-C6-haloalkyl, Ci-C6-alkylcarbonyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkenyl, C2-C6-haloalkenyl, Ci-C6-alkoxy, C1-C6- haloalkoxy, C3-C6-alkenyloxy, C3-C6-haloalkenyloxy, C3-C6-alkenyloxy, C3-C6- haloalkenyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, hydroxycarbonyl, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio, Ci-C6-haloalkylthio, NH2, (Ci-C6-alkyl)amino, di(Ci-C6-alkyl)amino, (Ci-C6-alkyl)sulfinyl, (Ci-C6-alkyl)sulfonyl, C3-C6-cycloalkyl, (C3-C6-cycloalkyl)oxy, or phenyl;
wherein the cyclic groups of R4 are unsubstituted or substituted by Ra;
Ra is halogen, CN , NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, d-Ce-alkoxy, or Ci-Ce-haloal- koxy;
m is 0, 1 , 2, or 3;
including agriculturally acceptable salts or derivatives of the pyridine compounds of formula (I) having an acidic functionality.
The pyridine compounds of formula (I) according to claim 1 , wherein
R1 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, or C3-C6-cycloal- kyl;
wherein the cycloalkyl substituent is unsubstituted.
The pyridine compounds of formula (I) according claim 1 or 2, wherein
R2 is C2-C6-alkenyl, C2-C6-haloalkenyl, CrC6-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C3- C6-cycloalkenyl, C3-C6-cycloalkenyl-Ci-C6-alkyl, C3-C6-cycloalkyl-CrC6-alkylidenyl, C3-C6-halocycloalkyl-Ci-C6-alkylidenyl, C3-C6-cycloalkenyl-Ci-C6-alkylidenyl, C3-C6- hydroxycycloalkyl-Ci-C6-alkyl, hydroxycycloalkenyl-Ci-C6-alkyl, Ci-C6-hydroxyalkyl, C3-C6-cycloalkyl-C2-C6-hydroxyalkylidenyl, hydroxycarbonyl-Ci-C6-alkyl, hydroxycar- bonyl-Ci-C6-haloalkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, C3-C6-hydroxycycloalkyl- Ci-C6-hydroxyalkyl, C2-C6-dihydroxyalkyl, d-Ce-cycloalkyl-d-drdihydroxyalkyli- denyl, hydroxycarbonyl-C2-C6-dihydroxyalkyl, d-dralkoxycarbonyl-d-Ce-dihydrox- yalkyl, Ci-C6-dicyanoalkyl, or 5- or 6-membered heteroaryl;
wherein hydroxy groups of R2 are unsubstituted or substituted by Rb;
cyclic groups of R2 are unsubstituted or substituted by Rc;
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd;
Rb is d-Ce-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C4-C6-cycloalkenyl, C3- C6-halocycloalkenyl, Ci-C6-alkoxycarbonyl-CrC6-alkyl, Ci-drhaloalkoxycarbonyl- Ci-C6-alkyl, Ci-C6-alkoxycarbonyl-Ci-C6-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci- C6-haloalkyl, Ci-C6-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, hydroxycarbonyl-Ci- C6-alkyl, hydroxycarbonyl-Ci-C6-haloalkyl, Ci-C6-alkyloxycarbonyl, Ci-C6-haloal- kyloxycarbonyl, Ci-C6-alkylthiocarbonyl, Ci-C6-haloalkylthiocarbonyl, Ci-di-alkyl- aminocarbonyl, Ci-C6-haloalkylaminocarbonyl, Ci-C6-dialkylaminocarbonyl, Ci- C6-dihaloalkylaminocarbonyl, Ci-C6-alkylsulfonyl, Ci-C6-haloalkylsulfonyl, C1-C6- alkoxy-Ci-C6-alkyl, CrC6-haloalkoxy-Ci-C6-alkyl, Ci-C6-alkoxy-CrC6-haloalkyl, CrC6-haloalkoxy-Ci-C6-haloalkyl, phenyl-Ci-C6-alkyl, or phenyl-Ci-C6-haloalkyl;
Rc is halogen, CN , NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci- C6-haloalkoxy, d-Gralkylthio, Ci-C6-alkylsulfinyl, or Ci-C6-alkylsulfonyl;
Rd is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl;
wherein the substituent Rd is unsubstituted or substituted by Re;
Re is halogen, CN , NO2, d-Ce-alkyl, Ci-Ce-haloalkyl, hydroxy, Ci-Ce-alkoxy or d- C6-haloalkoxy, Ci-C6-alkylsulfonyl.
The pyridine compounds of formula (I) according to any of claims 1 to 3, wherein Z is selected from below groups A to O,
Figure imgf000132_0001
Figure imgf000133_0001
wherein
Y 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2, or 3 heteroatoms selected from O, N, and S;
R3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
m is 0, 1 or 2;
R4 is halogen, CN, d-d-alkyl, d-d-haloalkyl, or d-d-alkoxy;
X is O, S, or NR3A;
R3A is H, d-d-alkyl, C C6-haloalkyl, d-C6-alkylcarbonyl, C3-C6-alkenyl, d-d- haloalkenyl, d-d-alkenyl, d-d-haloalkenyl, or C3-C6-cycloalkyl; and
# denotes the point of attachment to the pyridine ring.
The pyridine compounds of formula (I) according to any of claims 1 to 4, wherein
R1 is d-dralkyl, d-C6-alkoxy, d-drhaloalkoxy, d-d-alkenyloxy, d-d-haloal- kenyloxy d-d-alkynyloxy, d-C6-haloalkynyloxy, Ci-C6-alkylthio, or d-d-cycloal- kyl;
wherein the cycloalkyl substituent is unsubstituted;
R2 is d-d-alkenyl, d-d-haloalkenyl, d-d-alkoxy-d-d-alkenyl, d-d-alkynyl, d- d-cycloalkenyl, d-d-cycloalkenyl-d-d-alkyl, d-d-cycloalkyl-d-d-alkylidenyl, d-d-halocycloalkyl-d-d-alkylidenyl, d-d-cycloalkenyl-d-d-alkylidenyl, d-d- hydroxycycloalkyl-d-d-alkyl, hydroxycycloalkenyl-Ci-d-alkyl, Ci-d-hydroxyalkyl, d-d-cycloalkyl-C2-d-hydroxyalkylidenyl, hydroxycarbonyl-Ci-d-alkyl, hydroxycar- bonyl-Ci-d-haloalkyl, Ci-d-alkoxycarbonyl-Ci-d-alkyl, d-d-hydroxycycloalkyl- Ci-d-hydroxyalkyl, d-d-dihydroxyalkyl, d-C6-cycloalkyl-C3-d-dihydroxyalkyli- denyl, hydroxycarbonyl-d-d-dihydroxyalkyl, Ci-d-alkoxycarbonyl-d-C6-dihydrox- yalkyl, Ci-C6-dicyanoalkyl, or 5- or 6-membered heteroaryl;
wherein hydroxy groups of R2 are unsubstituted or substituted by Rb;
cyclic groups of R2 are unsubstituted or substituted by Rc;
acyclic aliphatic groups of R2 are unsubstituted or substituted by Rd;
Rb is d-d-alkyl, Ci-d-haloalkyl, d-C6-alkenyl, C3-d-haloalkenyl, d-d-alkynyl, d-C6-haloalkynyl, d-d-cycloalkyl, d-C6-halocycloalkyl, d-d-cycloalkenyl, d- d-halocycloalkenyl, Ci-d-alkoxycarbonyl-Ci-d-alkyl, Ci-d-haloalkoxycarbonyl- Ci-C6-alkyl, d-d-alkoxycarbonyl-d-d-haloalkyl, Ci-C6-haloalkoxycarbonyl-Ci- d-haloalkyl, Ci-d-alkylcarbonyl, Ci-C6-haloalkylcarbonyl, hydroxycarbonyl-d- d-alkyl, hydroxycarbonyl-Ci-C6-haloalkyl, Ci-d-alkyloxycarbonyl, Ci-C6-haloal- kyloxycarbonyl, Ci-d-alkylthiocarbonyl, Ci-d-haloalkylthiocarbonyl, Ci-d-alkyl- aminocarbonyl, d-d-haloalkylaminocarbonyl, Ci-d-dialkylaminocarbonyl, Ci- d-dihaloalkylaminocarbonyl, Ci-d-alkylsulfonyl, d-d-haloalkylsulfonyl, C1-C6- alkoxy-Ci-d-alkyl, Ci-d-haloalkoxy-Ci-d-alkyl, Ci-d-alkoxy-Ci-C6-haloalkyl, d-d-haloalkoxy-d-d-haloalkyl, phenyl-Ci-d-alkyl, or phenyl-Ci-d-haloalkyl; Rc is halogen, CN, N02, CrC6-alkyl, CrC6-haloalkyl, hydroxy, CrC6-alkoxy or Ci C6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, or Ci-C6-alkylsulfonyl;
Rd is phenyl, 5- or 6-membered heteroaryl, or 3- to 6-membered heterocyclyl; wherein the substituent Rd is unsubstituted or substituted by Re;
Re is halogen, CN, NO2, Ci-Ce-alkyl, d-Ce-haloalkyl, hydroxy, d-Ce-alkoxy or Ci C6-haloalkoxy, Ci-C6-alkylsulfonyl;
Z is selected from below groups A to O,
Figure imgf000134_0001
wherein
Y 5- or 6-membered partially or fully unsaturated carbocycle comprising 0, 1 , 2,
3 heteroatoms selected from O, N, and S;
R3 is halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, or Ci-C6-alkoxy;
m is 0, 1 or 2;
R4 is halogen, CN, Ci-Ce-alkyl, Ci-Ce-haloalkyl, or d-Ce-alkoxy;
X is O, S, or NR3A;
R3A is H, Ci-Ce-alkyl, Ci-Ce-haloalkyl, Ci-Ce-alkylcarbonyl, C3-C6-alkenyl, C3-C6- haloalkenyl, C3-C6-alkenyl, C3-C6-haloalkenyl, or C3-C6-cycloalkyl; and # denotes the point of attachment to the pyridine ring.
A use of pyridine compounds of formula (I), including agriculturally acceptable salts or derivatives of the pyridine compounds of formula (I) having an acidic functionality, according to any of claims 1 to 5, as herbicide.
A herbicidal compositions comprising: A) at least one pyridine compound of formula I, including agriculturally acceptable salts or derivatives of the pyridine compounds of formula (I) having an acidic functionality, according to any of claims 1 to 5;
and
B) herbicides of class b1 ) to b15):
b1 ) lipid biosynthesis inhibitors;
b2) acetolactate synthase inhibitors (ALS inhibitors);
b3) photosynthesis inhibitors;
b4) protoporphyrinogen-IX oxidase inhibitors,
b5) bleacher herbicides;
b6) enolpyruvyl shikimate 3-phosphate synthase inhibitors (EPSP inhibitors); b7) glutamine synthetase inhibitors;
b8) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); b9) mitosis inhibitors;
b10) inhibitors of the synthesis of very long chain fatty acids (VLCFA inhibitors);
b1 1 ) cellulose biosynthesis inhibitors;
b12) decoupler herbicides;
b13) auxinic herbicides;
b14) auxin transport inhibitors; and
b15) other herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, dalapon, daz- omet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flamprop, flamprop-isopropyl, flam- prop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol- butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, indazi- flam, maleic hydrazide, mefluidide, metam, methiozolin (CAS 403640- 27-7), methyl azide, methyl bromide, methyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoc- lamine, triaziflam, tridiphane and 6-chloro-3-(2-cyclopropyl-6-methylphe- noxy)-4-pyridazinol, and its salts and esters;
including their agriculturally acceptable salts or derivatives.
A herbicidal composition comprising the herbicidal composition according to claim 7, and safeners.
The herbicidal composition according to claim 7 or 8, wherein the herbicidal composition comprises at least one herbicide B selected from herbicides of class b1 , b2, b3, b4, b5, b6, b9, b10, b13 and b14.
0. The herbicidal composition according to claim 7 or 8, wherein the herbicidal composition comprises at least one herbicide B selected from herbicides of class b1 , b2, b4, b5, b9, b10, b13 and b14. 1 1 The herbicidal composition according to any of claims 7 to 10, wherein the weight ratio of component A to component B is in the range of from 1 :500 to 500:1.
A herbicidal composition comprising a herbicidal active amount of at least one pyridine compound of formula (I), including agriculturally acceptable salts or derivatives of the pyridine compounds of formula (I) having an acidic functionality, according to any of claims 1 to 5, and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substance.
A herbicidal composition comprising a herbicidal composition according to any of claims 7 to 1 1 , and at least one inert liquid and/or solid carrier and, if appropriate, at least one surface-active substance.
A method of controlling undesired vegetation, which comprises allowing a herbicidal active amount of at least one pyridine compound of formula (I), including agriculturally acceptable salts or derivatives of the pyridine compounds of formula (I) having an acidic functionality, according to any of claims 1 to 5 or a herbicidal composition according to any of claims 7 to 13 to act on plants, their environment or on seed. 15. A use of the herbicidal compositions according to any of claims 7 to 13 as herbicides.
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