EP2350069A1 - Pyridines substituées à action herbicide - Google Patents

Pyridines substituées à action herbicide

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Publication number
EP2350069A1
EP2350069A1 EP09736916A EP09736916A EP2350069A1 EP 2350069 A1 EP2350069 A1 EP 2350069A1 EP 09736916 A EP09736916 A EP 09736916A EP 09736916 A EP09736916 A EP 09736916A EP 2350069 A1 EP2350069 A1 EP 2350069A1
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European Patent Office
Prior art keywords
formula
compounds
combination
alkyl
row
Prior art date
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EP09736916A
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German (de)
English (en)
Inventor
Dschun Song
Eike Hupe
Christian Pilger
Trevor William Newton
Matthias Witschel
William Karl Moberg
Liliana Parra Rapado
Tao QU
Frank Stelzer
Andrea Vescovi
Thomas Seitz
Thomas Ehrhardt
Klaus Kreuz
Klaus Grossmann
Robert Reinhard
Anja Simon
Ricarda Niggeweg
Bernd Sievernich
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BASF SE
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BASF SE
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Priority to EP09736916A priority Critical patent/EP2350069A1/fr
Publication of EP2350069A1 publication Critical patent/EP2350069A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
    • C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
    • C07D311/12—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 3 and unsubstituted in position 7
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Definitions

  • the present invention relates to substituted pyridines of the formula I.
  • variables have the following meaning R 1 OR A , S (O) n -R A or OS (O) n -R A ;
  • R A is hydrogen, C 1 -C 4 -alkyl, ZC 3 -C 6 -cycloalkyl, C 1 -C 4 -haloalkyl, C 2 -C 6 -alkenyl, ZC 3 -C 6 -cycloalkenyl, C 2 -C 6 Alkynyl, Z- (tri-C 1 -C 4 -alkyl) silyl,
  • R a is hydrogen, OH, Ci-C 8 -alkyl, C 4 haloalkyl, ZC 3 -C 6 cycloalkyl, C 2 -C 8 -alkenyl-Al, ZC 5 -C 6 cycloalkenyl, C 2 -C 8 -alkynyl, Z-C 1 -C 6 -alkoxy, Z-C 1 -C 4 -haloalkoxy, ZC 3 -C 8 -alkenyloxy, ZC 3 -C 8 -alkynyloxy, NR 1 R ", C 1 -C 6 -alkylsulfonyl , Z- (tri-C 1 -C 4 -alkyl) silyl, Z-phenyl, Z-phenoxy, Z-phenylamino and 5- or 6-membered monocyclic or 9- or
  • R 1 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S, wherein the cyclic groups are unsubstituted or substituted by 1, 2, 3 or 4 groups R b ;
  • bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S;
  • R 1 and R may also together with the N-atom to which they are attached form a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S;
  • Z is a covalent bond or C 1 -C 4 -alkylene; n is O, 1 or 2;
  • R 2 is phenyl, naphthyl or and 5- or 6-membered monocyclic or 9- or 10-membered bicyclic aromatic heterocycle containing 1, 2, 3 or 4 heterocyclic roatoms selected from O, N and S, where the cyclic groups are unsubstituted or substituted by 1, 2, 3 or 4 groups R b ;
  • R b is independently Z-CN, Z-OH, Z-NO 2,
  • R bb Z- (tri-C 1 -C 4 -alkyl) silyl, Z-phenyl and S (O) "R bb , wherein R bb is C 1 -C 6 -alkyl and C 1 -C 6 -haloalkyl and n is 0, 1 or 2 stands; R b can also form, together with the group R b attached to the adjacent carbon atom, a five- or six-membered saturated, partially or completely unsaturated ring which, in addition to carbon, 1, 2 or 3 heteroatoms selected from O, N and S.
  • X is O, S or NR 3;
  • R 3 is hydrogen, C 1 -C 6 -alkyl, dd-haloalkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkynyl,
  • R a2 is C 1 -C 6 -alkyl, C 1 -C 4 -haloalkyl, Z-C 1 -C 6 -alkoxy, Z-C 1 -C 4 -haloalkoxy and
  • R c is hydrogen or one of the groups mentioned for R b ; wherein in groups R A and R 3 and their sub-substituents, the carbon chains and / or the cyclic groups may be partially or completely substituted by groups R b , and their N-oxides and agriculturally suitable salts.
  • the invention relates to processes and intermediates for the preparation of pyridines of the formula I and their N-oxides, their agriculturally useful salts, as well as active ingredient combinations containing them, agents containing them and their use as herbicides, i. for controlling harmful plants, and a method for controlling unwanted plant growth, which comprises allowing a herbicidally effective amount of at least one pyridine compound of the formula I or an agriculturally useful salt of I to act on plants, their seeds and / or their habitat.
  • WO 2008/009908 WO 2008/071918 herbicidal pyridopyrazines are described, their herbicidal activity at low application rates, or compatibility with crops remains in need of improvement.
  • An object of the present invention is to provide compounds having herbicidal activity.
  • active ingredients should be made available which have a high herbicidal action, in particular even at low application rates, and their compatibility with crop plants for commercial exploitation is sufficient.
  • the compounds according to the invention can be prepared analogously to the synthetic routes described in WO 2008/009908 and WO 2008/071918 by standard methods of organic chemistry, for example according to the following synthesis route:
  • Pyridinecarboxylic acids of the formula II can be reacted with carbonyl compounds of the formula III to give compounds of the formula IV.
  • the variables have the meaning given for formula I.
  • the group Hal represents a halogen atom or another suitable nucleophilic leaving group, such as alkoxy or phenoxy.
  • This reaction is usually carried out at temperatures from -78 0 C to 12O 0 C, preferably -2O 0 C to 5O 0 C, in an inert organic solvent in the presence of a base such as. Triethylamine (see J. Agric and Food Chem., 1994, 42 (4), 1019-1025), a catalyst such as e.g. B. Dicyclohexylcarbodiimide (see Egyptian Journal of Chemistry 1994, 37 (3), 273-282.) Or other known coupling reagents.
  • a base such as. Triethylamine (see J. Agric and Food Chem., 1994, 42 (4), 1019-1025)
  • a catalyst such as e.g. B. Dicyclohexylcarbodiimide (see Egyptian Journal of Chemistry 1994, 37 (3), 273-282.) Or other known coupling reagents.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, more preferably halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene.
  • ethers
  • Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and Calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydrogencarbonates such as sodium hydrogencarbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyl lithium and phenyl lithium, alkyl magnesium halides such as methyl magnesium chloride and alkali metal and alkaline earth metal alkoxides such as sodium methoxide.
  • tertiary amines such as trimethylamine, triethylamine, tributylamine, di-isopropylethylamine and N-methylpiperidine
  • pyridine substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration.
  • tertiary amines such as trimethylamine, triethylamine, tributylamine, di-isopropylethylamine.
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • the starting materials are generally reacted with one another in equimolar amounts.
  • the compounds of formula IV are activated by introducing a leaving group L 1 .
  • Suitable leaving groups L 1 are generally those groups which increase the electrophilicity of the carbonyl group, for example O-alkyl, O-aryl, halides, activated esters or aldehydes (such as, for example, Weinreb amide), in particular pentafluorophenoxy.
  • This reaction is usually carried out at temperatures from -78 0 C to 12O 0 C, preferably -2O 0 C to 5O 0 C, in an inert organic solvent in the presence of a base such as. Triethylamine (see J. Agric and Food Chem., 1994, 42 (4), 1019-1025), a catalyst such as e.g. B. Dicyclohexylcarbodiimide (see Egyptian Journal of Chemistry 1994, 37 (3), 273-282) or other known coupling reagents.
  • a base such as. Triethylamine (see J. Agric and Food Chem., 1994, 42 (4), 1019-1025)
  • a catalyst such as e.g. B. Dicyclohexylcarbodiimide (see Egyptian Journal of Chemistry 1994, 37 (3), 273-282) or other known coupling reagents.
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably methylene chloride and toluene.
  • aromatic hydrocarbons such as toluene, o-,
  • Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcite oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and Calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as Lithium carbonate, potassium carbonate and calcium carbonate and alkali metal hydrogencarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and alkali metal and alkaline earth metal alkoxides such
  • alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate, calcium carbonate, cesium carbonate and rubidium carbonate.
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • agent HL 1 are alcohols, optionally subst. Phenols, N, O-dialkylhydroxylamine, in particular pentafluorophenol or N, O-dimethylhydroxylamine in question.
  • the compounds of formula V are cyclized to the compounds of formula I.
  • This reaction is usually carried out at temperatures of from -78 ° C to 120 0 C, preferably from -20 0 C to 50 0 C, in an inert organic solvent in the presence of a base or a Lewis acid or a catalyst [cf.. Silverman, Richard BJ Am. Chem. Soc. 1981, 103 (13), 3910].
  • Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably acetonitrile and dimethylformamide. Mixtures of the solvents mentioned can also be used.
  • Bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, Alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate, calcium carbonate, cesium carbonate and rubidium carbonate and also alkali metal hydrogencarbonates, such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls, such as methyllithium, butyllithium and phenyllithium, alkylmagnesium halides, such as methylmagnesium chloride, and alkali metal and alkaline earth metal alkoxides,
  • the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
  • the starting materials are generally reacted with one another in equimolar amounts.
  • the compounds of the formula I can also be obtained via a reverse reaction sequence, ie from the reaction of the compounds of the formula II with compounds HL 1 , the activated derivatives of the formula VI are obtained.
  • reaction mixtures are worked up in a customary manner, for example by mixing with water, separating the phases and optionally chromatographic purification of the crude products.
  • Some of the intermediate and end products are in the form of colorless or slightly brownish, viscous oils which are freed from volatile constituents under reduced pressure and at moderately elevated temperature. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration. If individual compounds I are not accessible in the above-described ways, they can be prepared by derivatization of other compounds I.
  • All hydrocarbon chains such as alkyl, halo (gen) alkyl, alkenyl, alkynyl, and the alkyl moieties and alkenyl moieties in alkoxy, halo (gen) alkoxy, Alkylamino, dialkylamino, N-alkylsulfonylamino, alkenyloxy, alkynyloxy, alkoxyamino, alkylaminosulfonylamino, dialkylaminosulfonylamino, alkenylamino, alkynylamino, N- (alkenyl) -N- (alkyl) -amino, N- (alkynyl) -N- (alkyl) -amino, N- (alkoxy) -N- (alkyl) -amino, N- (alkenyl) -N- (alkyl) -amino, N- (alkynyl) -N-
  • halogenated substituents preferably carry one to five identical or different halogen atoms, in particular fluorine atoms or chlorine atoms.
  • the meaning halogen in each case represents fluorine, chlorine, bromine or iodine.
  • Alkyl and the alkyl moieties for example, in alkoxy, alkylamino, dialkylamino, N-alkylsulfonylamino, alkylaminosulfonylamino, dialkylaminosulfonylamino, N- (alkenyl) -N- (alkyl) -amino, N- (alkynyl) -N- (alkyl) -amino, N- (Alkoxy) -N- (alkyl) -amino: saturated, straight-chain or branched hydrocarbon radicals having one or more C atoms, for example 1 to 2, 1 to 4, or 1 to 6 carbon atoms, for example C 1 -C 6 -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methyl
  • alkyl is small alkyl groups such as C 1 -C 4 -alkyl. In another embodiment of the invention, alkyl is greater alkyl groups such as Cs-C ⁇ -alkyl.
  • Haloalkyl also referred to as haloalkyl: an alkyl radical as mentioned above, the hydrogen atoms of which are partially or completely substituted by halogen atoms such as fluorine, chlorine, bromine and / or iodine, eg chloromethyl, dichloromethyl, trisubstituted chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-di-fluoroethyl, 2,2,2-trifluoroethyl, 2- Chloro
  • Cycloalkyl and the cycloalkyl moieties for example in cycloalkoxy or cycloalkyl carbonyl: monocyclic saturated hydrocarbon groups having three or more carbon atoms, for example 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Alkenyl and alkenyl moieties for example, in alkenylamino, alkenyloxy, N- (alkenyl) -N- (alkyl) -amino, N- (alkenyl) -N- (alkoxy) -amino: monounsaturated, straight-chain or branched hydrocarbon radicals having two or more carbon atoms. Atoms, z. 2 to 4, 2 to 6 or 3 to 6 carbon atoms and a double bond in any position, e.g.
  • C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 Methyl 2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3 Methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl 3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-1
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having 3 to 6, preferably 5 to 6 carbon ring members, such as cyclopenten-1-yl, cyclopentene-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl ,
  • Alkynyl and alkynyl moieties for example, in alkynyloxy, alkynylamino, N- (alkynyl) -N- (alkyl) -amino or N- (alkynyl) -N- (alkoxy) -amino: straight-chain or branched hydrocarbon groups with two or more C atoms -Atoms, z. B. 2 to 4, 2 to 6, or 3 to 6 carbon atoms and a triple bond in any position, for.
  • C 2 -C 6 -alkynyl such as ethynyl, 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-
  • Alkoxy alkyl, as defined above, which is bonded via an oxygen atom: z.
  • 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S may be bonded via C or N.
  • Saturated or unsaturated heterocyclic groups bonded via N such as: pyridazine-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazine-2-yl, 2 -Furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl , isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl , Oxazol-5-yl, thiazol-2-yl
  • C-linked heteroaromatic groups such as: pyrazol-3-yl, imidazol-5-yl, oxazol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, pyridin-2-yl , Pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl, pyrazine-2-yl, [1H-tetrazole-5 -yl and [2H] -tetrazol-5-yl.
  • the compounds of the formula I can contain one or more further chiral centers.
  • the compounds according to the invention can therefore be present as pure enantiomers or diastereomers or as mixtures of enantiomers or diastereomers.
  • the invention relates to both the pure enantiomers or diastereomers and mixtures thereof.
  • the compounds of the formula I can also be present in the form of the N-oxides and / or their agriculturally useful salts, the type of salt generally not being important.
  • the salts of those cations or the acid addition salts of those acids come into consideration whose cations, or anions, do not adversely affect the herbicidal activity of the compounds I.
  • the cations used are in particular ions of the alkali metals, preferably lithium, sodium or potassium, the alkaline earth metals, preferably calcium or magnesium, and the transition metals, preferably manganese, copper, zinc or iron.
  • ammonium as cation, in which case, if desired, one to four hydrogen atoms are represented by C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxyC 1 -C 4 alkoxy-C 1 -C 4 -alkyl, phenyl or benzyl, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyethyl) 1-yl) ammonium, trimethylbenzylammonium.
  • ammonium cation is the pyridine nitrogen atom of the formula I quaternized by alkylation or arylation.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate,
  • variables of the compounds of the formula I have the following meanings, these being considered both individually and in combination with one another in particular embodiments of the compounds of the formula I:
  • A is N and E, G and M are hen of the formula 1.1,
  • R c2 , R c3 and R c4 each correspond to a group R c and preferably have the following meanings: R c2 H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and
  • R c3 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H; and R c4 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H.
  • R 1 is selected from OH, OCH 3 , OC (O) CH 3 , OC (O) CH 2 CH 3 , OC (O) CH (CH 3 ) 2 , OC (O) C (CH 3 ) 3 , OC (O) -CC 3 H 5 , OC (O) -C 6 H 5 , OC (O) - CH 2 C 6 H 5 , OC (O) CH 2 Cl, OC (O) -CF 3 , OC (O) -CH 2 OCH 3 , OC (O) -N (CH 3 ) 2 and OC (O) - OCH 2 CH 3 .
  • R 2 is phenyl which is substituted by a group selected from 2-Br, 2-CI, 2,4-Cl 2 , 2-CI-4-F , 2-CI-5-F, 2-CI-6-F, 2-CI-4-CF 3 , 2-CI-5-CF 3 , 2-CI-6-CF 3 , 2-CI-3,6- F 2 , 2-F, 2,4-F 2 , 2,5-F 2 , 2,6-F 2 , 2-F-4-CF 3 , 2-F-5-CF 3 , 2-F 6-CF 3 , 2,3,6-F 3 , 2-NO 2 , 2-NO 2 -4-F, 2-NO 2 -5-F, 2-NO 2 -6-F, 2-NO 2 4-CF 3 , 2-NO 2 -5-CF 3 , 2-NO 2 -6-CF 3 , 2-NO 2 -3,6-F 2 , 2-CN, 2-CH 3 , 2-CH 3 -4-F, 2-CH 3 -5-F, 2-CN, 2-CH 3 , 2-CH 3 -4-F, 2-CH 3 -5
  • X is selected from oxygen and sulfur.
  • A, G and M are CR c and E is N. These compounds correspond to the formula 1.2,
  • R c1 , R c2 and R c4 each correspond to a group R c and preferably have the following meanings: R c1 H, OH, CN, halogen, alkyl, alkoxy, haloalkyl; R c2 H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and
  • R c4 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and
  • A, E and G are CR c and M is N.
  • R c1 , R c2 and R c3 each correspond to a group R c and preferably have the following meanings:
  • R c1 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H
  • R c2 is H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H
  • R c3 H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and
  • At least one group R c1 , R c2 and R c3 is not hydrogen.
  • Particularly preferred embodiments of the compounds of the formula I relate to those of each of the formulas 1.1 to 1.4, in which the variables have the meanings preferred for formula I.
  • R 1 is O -R A. In a further preferred embodiment of the invention, R 1 is S (O) n -R A , where n is preferably O or 2, in particular 2.
  • R 1 is OS (O) n -R A , where n is preferably O or 2, in particular 2, for example OS (O) 2 -CH 3, OS (O) 2 - C 2 H 5 , OS (O) 2 -C 3 H 7 , OS (O) 2 -C 6 H 5 or OS (O) 2 - (4-CH 3 -C 6 H 4 ).
  • R 1 is O-S (O) n -NR 1 R ", in particular with the groups NR 1 R" mentioned below as preferred.
  • Benzoyl such as C (O) C 6 H 5 , C (O) [2-CH 3 -C 6 H 4 ], C (O) [4-CH 3 -C 6 H 4 ], C (O) [2 -FC 6 H 4 ], C (O) [4-FC 6 H 4 ], or optionally subst.
  • Heteroaryl such as pyridine, which is bonded via a carbonyl group.
  • R A is H or C 1 -C 6 -alkylcarbonyl.
  • R A is selected from the group H, OCH 3 , C (O) CH 3 , C (O) CH 2 CH 3 , C (O) CH (CH 2 ) 2 , C (O) C (CH 3 ) 3 , C (O) -CC 3 H 5 , C (O) -C 6 H 5 , C (O) -CH 2 C 6 H 5 , C (O) CH 2 Cl, C (O) CF 3 , C ( O) CH 2 OCH 3 , C (O) N (CH 3 ) 2 and C (O) OCH 2 CH 3 .
  • R A is NR 1 R ".
  • R A is Z-NR'-C (O) -NR'R", where R 1 and R "are as described above
  • R 1 and R "independently of one another are also C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, in particular OCH 3 , OC 2 H 5 , CH 2 CH 2 OCH 3 and CH 2 CH 2 Cl.
  • N (di-C 1 -C 4 -alkyl) is N (di-C 1 -C 4 -alkyl), in particular N (CH 3 ) -Ci-C 4 -alkyl, such as N (CH 3 ) 2 , N (CH 3 ) CH 2 CH 3 , N (CH 3 ) C 3 H 7 and N (CH 3 ) CH (CHs) 2 .
  • NR 1 R are NH-aryl, where aryl is preferably phenyl which is substituted, in particular in the 2- and 6-position, by one to three identical or different groups, halogen, CH 3 , halogen dC 2 -alkyl, halo-C 1 -C 2 -alkoxy and carboxyl such as 2-Cl, 6-COOH-C 6 H 3 , 2,6-Cl 2 -C 6 H 3 , 2,6-F 2 -C 6 H 3 , 2,6-Cl 2 3-C 6 H 2 , 2-CF 3 , 6-CH 2 CHF 2 -C 6 H 3 , 2-CF 3 , 6-OCF 3 -C 6 H 3 and 2 -CF 3 , 6-CH 2 CHF 2 -C 6 H 3 .
  • aryl is preferably phenyl which is substituted, in particular in the 2- and 6-position, by one to three identical or different groups, halogen, CH 3 , halogen dC 2 -alkyl,
  • NR 1 R are NH heteroaryl, wherein heteroaryl preferably represents one of the preferred heteroaromatic groups below, in particular triazinyl, pyrimidinyl or triazolopyrimidinyl, such as [1, 2,4] triazolo [1,5-a] pyrimidine 2-yl, which groups may be substituted, in particular by C 1 -C 4 -alkoxy and / or halogen Particularly preferred are 5,7-dimethoxy- [1,2,4] triazolo [1,5-a ] pyrimidin-2-yl, 5,7-diethoxy- [1,2,4] triazolo [1,5-a] pyrimidin-2-yl, 5-fluoro-7-methoxy- [1,2,4] triazolo [1, 5-a] pyrimidin-2-yl and 5-fluoro-7-ethoxy- [1,2,4] triazolo [1,5-a] pyrimidin-2-yl.
  • heteroaryl preferably represents one of the
  • R A is a 5- or 6-membered heterocycle optionally substituted by R b as defined above, which is preferably either 1, 2, 3 or 4 nitrogen atoms or 1 oxygen or 1 sulfur atom and optionally 1 or 2 has nitrogen atoms as ring members and which is unsubstituted or may have 1 or 2 substituents selected from R b .
  • N such as, for example: heteroaromatic groups: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazine-2 yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazole 5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazole-4 yl, oxazol-5-yl, thia
  • R A is a C-bonded heteroaromatic group such as pyrazol-3-yl, imidazol-5-yl, oxazol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazole-5 yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidine-5-yl, pyridazin-4-yl, pyrazine-2-yl yl, [1 H] -tetrazol-5-yl and [2H] -tetrazol-5-yl, where the heterocycles 1 or 2 mentioned here by way of example from R b may have selected substituents.
  • R b are F, Cl, CN, NO 2 , CH 3 , C 2 H 5 , OCH 3 , OC 2 H 5 , OCHF 2 , OCF 3 and CF 3 .
  • R 2 is phenyl which is unsubstituted or partially or completely substituted by groups R b .
  • Particularly preferred are those compounds in which a group R b is in the ortho position. Such compounds of the formula I are described by the formula I.A .:
  • R 5 and R 6 are groups R b , as defined above, preferably halogen , NO 2, C 1 -C 4 -alkyl, C 1 -C 2 -haloalkyl and C 1 -C 4 -alkoxy.
  • a group R 6 is preferably in position 5.
  • a group R 6 in position 3 represents a further preferred embodiment.
  • R 5 particularly preferably represents Br, F, NO 2 , CN, CH 3 , OCH 3 , CHF 2 or OCHF 2 .
  • R 6 particularly preferably represents halogen or halomethyl, such as Cl, F or CF 3 . More preferably, (R 6 ) m is selected from 4-F, 5-F, 6-F, 4-CF 3 , 5-CF 3 and 3,6-F 2 .
  • X is O. In another embodiment, X is S. In another embodiment, X is NR 3 .
  • C 1 -C 6 -alkyl such as CH 3 , C 2 H 5 , nC 3 H 7
  • Phenyl such as C 6 H 5 , 4 -CH 3 -C 6 H 4 , 4-FC 6 H 4 or S (O) n -R N , wherein R N is C 1 -C 6 -haloalkyl, such as CH 2 CF. 3, CH 2 CHF. 2 Particularly preferably, R 3 is H. If the compounds of the formula I have two groups R 3 , these groups may be identical or different. A preferred embodiment of R 3 is CH 2 CN, another is CH 2 C 6 H 5 . Another preferred embodiment of R 3 is optionally subst.
  • Phenyl such as C 6 H 5 , 4 -CH 3 -C 6 H 4 , 4-FC 6 H 4 or S (O) n -R N , wherein R N is C 1 -C 6 -haloalkyl, such as CH 2 CF. 3, CH 2 CHF. 2
  • a further embodiment relates to the N-oxides of the compounds of the formula I.
  • a further embodiment relates to salts of the compounds of the formula I, in particular those obtainable by quaternization of the pyridine nitrogen atom, which can preferably be effected by alkylation or arylation of the compounds of the formula I.
  • preferred salts of the compounds are the N-alkyl, in particular the N-methyl, or the N-phenyl salts.
  • One embodiment relates to the compounds of Tables 11 to 20 and 31 to 60, the compounds A-1 to A-14 and A-29 to A-341 of Tables 21 to 30, and the compounds in which R 1 is an OS ( O) represents 2- bonded group.
  • Another embodiment relates to the compounds of Tables 131 to 140 and 151 to 180, the compounds A-1 to A-14 and A-29 to A-341 of Tables 141 to 150, and the compounds in which R 1 is a via OS (O) 2- bonded group.
  • Table 13 Compounds of the formula 1.1A, in which XO and R 3 are C 2 H 5 , (R 6 ) m is 3-CI and the combination of R 1 and R 5 for a compound corresponds in each case to one row of table A.
  • Table 22 Compounds of the formula 1.1A, in which XO and R 3 are CH 3 , (R 6 ) m is 4-CI and the combination of R 1 and R 5 for each compound corresponds to one row of Table A. ## STR4 ## A-15 to A-28 preferred embodiments.
  • Table 23 Compounds of the formula 1.1A, in which XO and R 3 are C 2 H 5 , (R 6 ) m is 4-CI and the combination of R 1 and R 5 for each compound corresponds to one row of table A Darin Compounds A-15 to A-28 are preferred embodiments.
  • the compounds A-15 to A-28 are preferred embodiments.
  • Table 35 Compounds of the formula 1.1A, in which XO and R 3 are CH (CH 3 ⁇ , (R 6 ) m is 5-CI and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 44 Compounds of the formula 1.1A, in which XO and R 3 n-C ⁇ H? (R 6 ) m is 6-CI and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 52 Compounds of the formula 1.1A, in which XO and R 3 are CH 3 , (R 6 ) m is 3-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 60 Compounds of the formula 1.1A, in which XO and R 3 are CH 2 C 6 H 5, (R 6 ) m is 3-F and the combination of R 1 and R 5 for each compound corresponds to one row of Table A.
  • Table 65 Compounds of the formula 1.1A, in which XO and R 3 are CH (CH 3 ⁇ , (R 6 ) m is 4-F and the combination of R 1 and R 5 for each compound corresponds to one row of Table A.
  • Table 68 Compounds of the formula 1.1A, in which XO and R 3 are ChbC ⁇ CH, (R 6 ) m is 4- F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 78 Compounds of the formula 1.1A, in which XO and R 3 are ChbC ⁇ CH, (R 6 ) m is 5-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 79 Compounds of the formula 1.1A, in which XO and R 3 are ChbC ⁇ CH, (R 6 ) m is 5-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 81 Compounds of the formula 1.1A, in which XO and R 3 are H, (R 6 ) m is 6-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 86 Compounds of the formula 1.1A, in which XO and R 3 (R 6 ) m is 6-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 99 Compounds of the formula 1.1A, in which XO and R 3 are CH 2 CN, (R 6 ) m is 4-CF 3 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 100 Compounds of the formula 1.1A, in which XO and R 3 are CH 2 CN, (R 6 ) m is 4-CF 3 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 102 Compounds of the formula 1.1A, in which XO and R 3 are CH3, (R 6 ) m is 5-CF3 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 110 Compounds of the formula 1.1A, in which XO and R 3 are CH 2 CeH 5 , (R 6 ) m for 5- CF3 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 120 Compounds of the formula 1.1A, in which XO and R 3 are CH 2 CeHs, (R 6 ) m is 3,6-F 2 and the combination of R 1 and R 5 is a compound of one row of Table A corresponds to Table 121
  • Table 123 Compounds of the formula 1.1A in which XS and R 3 are C2H5, the subscript m in (R 6 ) m is zero and the combination of R 1 and R 5 for a compound corresponds in each case to one row of table A.
  • Table 128 Compounds of the formula MA in which XS and R 3 are ChbC ⁇ CH, the subscript m in (R 6 ) m is zero and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 131 Compounds of the formula MA, in which XS and R 3 are H, (R 6 ) m is 3-CI and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 136 Compounds of the formula 1.1A, in which XS and R 3 nC 4 H9, (R 6 ) m is 3-CI and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 141 Compounds of the formula 1.1A, in which XS and R 3 are H, (R 6 ) m is 4-CI and the combination of R 1 and R 5 is a compound of one row of the table A corresponds
  • the compounds A-15 to A-28 are preferred embodiments.
  • Table 153 Compounds of the formula 1.1A in which XS and R 3 are C2H5, (R 6 ) m is 5-CI and the combination of R 1 and R 5 for a compound corresponds in each case to one row of table A.
  • Table 158 Compounds of the formula 1.1A, in which XS and R 3 are CH 2 C ⁇ CH, (R 6 ) m is -Cl and the combination of R 1 and R 5 for a compound corresponds in each case to one row of table A.
  • Table 162 Compounds of the formula 1.1A, in which XS and R 3 are CH 3 , (R 6 ) m is 6-CI and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 170 Compounds of the formula 1.1 A, in which XS and R 3 are CH 2 CeH 5 , (R 6 ) m for 6-CI and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 175 Compounds of the formula 1.1A, in which XS and R 3 are CH (CH 3 ⁇ , (R 6 ) m is 3-F and the combination of R 1 and R 5 for each compound corresponds to one row of Table A.
  • Table 180 Compounds of the formula 1.1A, in which XS and R 3 are CH 2 C 6 H 5, (R 6 ) m is 3-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 181 Compounds of the formula 1.1A, in which XS and R 3 are CH 2 C 6 H 5, (R 6 ) m is 3-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 188 Compounds of the formula 1.1A, in which XS and R 3 are CH 2 C ⁇ CH, (R 6 ) m is 4-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 191 Compounds of the formula 1.1A, in which XS and R 3 are H, (R 6 ) m is 5-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 196 Compounds of the formula 1.1A, in which XS and R 3 (R 6 ) m is 5-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 201 Compounds of the formula 1.1A, in which XS and R 3 are H, (R 6 ) m is 6-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 202 Compounds of the formula 1.1A, in which XS and R 3 are H, (R 6 ) m is 6-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 202 Compounds of the formula 1.1A, in which XS and R 3 are H, (R 6 ) m is 6-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 204 Compounds of the formula 1.1A, in which XS and R 3 denote n-C3H7, (R 6 ) m represents 6-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 209 Compounds of the formula 1.1A in which XS and R 3 are CH 2 CN, (R 6 ) m is 6-F and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 212 Compounds of the formula 1.1A, in which XS and R 3 are CH3, (R 6 ) m for 4-CF3 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • Table 222 Compounds of the formula 1.1A in which XS and R 3 are CH 3 , (R 6 ) m is 5CF 3 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of table A.
  • Table 223 Compounds of the formula 1.1A in which XS and R 3 are CH 3 , (R 6 ) m is 5CF 3 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of table A.
  • Table 225 Compounds of the formula 1.1A, in which XS and R 3 are CH (CH 3 ) 2, (R 6 ) m is 5 -CF 3 and the combination of R 1 and R 5 for each compound corresponds to one row of Table A.
  • Table 230 Compounds of the formula 1.1A in which XS and R 3 are CH 2 C 6 H 5, (R 6 ) m is 5 -CF 3 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of table A.
  • Table 233 Compounds of the formula 1.1A, in which XS and R 3 are C2H5, (R 6 ) m for 3,6-F2 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
  • T1 4-CH 3 -C 6 H 4
  • T3 N (CH 3) CH 2 CH 3
  • T5 N (CH 3) CH (CHs) 2
  • T9 2,6-Cl 2 , 3-CH 3 -C 6 H 2
  • T10 2-CF 3 , 6-CH 2 CHF 2 -C 6 H 3
  • T1 1 2-CF 3 , 6-OCF 3 -C 6 H 3
  • T12 2-CF 3 , 6-OCH 2 CHF 2 -C 6 H 3
  • the compounds I and their agriculturally useful salts are suitable - both as mixtures of isomers and in the form of pure isomers - as herbicides. They are suitable as such or as appropriately formulated agent.
  • the compounds I in particular the preferred embodiments thereof, or agents containing them can be used in a further number of crop plants for the removal of undesirable plants.
  • the following cultures may be considered:
  • crops also includes those that have been modified by breeding, mutagenesis or genetic engineering methods.
  • Genetically engineered plants are plants whose genetic material has been altered in a manner that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information).
  • one or more genes are integrated into the genome of the plant in order to improve the properties of the plant.
  • crops thus also encompasses plants which by breeding and genetic engineering measures tolerance to certain herbicide classes, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as. Sulfonylureas (EP-A-0257993, US Pat. No. 5,013,659) or imidazolinones (see, for example, US Pat. No.
  • certain herbicide classes such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as. Sulfonylureas (EP-A-0257993, US Pat. No. 5,013,659) or imidazolinones (see, for example, US Pat. No.
  • EPSPS enolpyruvylshikimate-3-phosphate synthase
  • Glyphosate see, for example, WO 92/00377
  • glutamine synthetase (GS) inhibitors such as, for example, Glufosinate (see eg EP-A-0242236, EP-A-242246) or oxynil herbicides (see eg US 5,559,024).
  • crops thus also includes plants that use genetic engineering measures one or more toxins, eg. As those from the bacterial strain Bacillus ssp., Produce.
  • Toxins produced by such genetically engineered plants include e.g. Insecticidal proteins of Bacillus spp., In particular B. thuringiensis such as the endotoxins CrylAb, CrylAc, CrylF, Cry1Fe2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), e.g.
  • VIPs vegetative insecticidal proteins
  • VIP1, VIP2, VIP3, or VIP3A insecticidal proteins of nematode-colonizing bacteria, e.g. B. Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg. B. Wepsen, spider or scorpion toxins; fungal toxins, e.g. B. from streptomycetes; herbal lectins, e.g. From pea or barley; agglutinins; Proteinase inhibitors, e.g. Trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome Inactivating Proteins (RIPs), e.g.
  • RIPs Ribosome Inactivating Proteins
  • Steroid metabolizing enzymes e.g. 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors or HMG-CoA reductase
  • ion channel blocker e.g.
  • toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins.
  • Hybrid proteins are characterized by a novel combination of different protein domains (see, for example, WO 2002/015701).
  • Further examples of such toxins or genetically modified plants which produce these toxins are described in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 and WO 03/052073.
  • the methods for producing these genetically modified plants are known in the art and z. As set forth in the publications mentioned above.
  • YieldGard ® (corn cultivars producing the toxin CrylAb), YieldGard ® Plus (corn cultivars producing the toxins CrylAb and Cry3Bb1), StarLink ® (corn cultivars producing the toxin Cry9c), Herculex ® RW (corn cultivars toxins which Cry34Ab1, Cry35Ab1 and the enzyme
  • Agrisure ® CB and Bt176 from Syngenta Seeds SAS, France corn varieties which produce the toxin CrylAb and the PAT enzyme
  • MIR604 from Syngenta Seeds SAS, France
  • MON 863 from Monsanto Europe SA, Belgium
  • IPC 531 from Monsanto Europe SA, Belgium
  • cottons producing a modified version of the toxin CrylAc 1507 from Pioneer Overseas Corporation, Belgium (maize varieties producing the toxin Cryl F and the PAT enzyme).
  • crops thus also includes plants that produce by genetic engineering measures one or more proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens, such as.
  • PR proteins pathogenesis-related proteins
  • Resistance proteins eg, potato varieties that produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum
  • T4 lysozyme eg, potato varieties that are resistant to bacteria such as Erwinia amylvora as a result of the production of this protein.
  • crops thus also includes plants whose productivity has been improved by means of genetic engineering methods by
  • crops also includes plants whose ingredients have been modified in particular to improve the human or animal diet using genetic engineering methods by z.
  • oil plants can produce health-promoting long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids (eg Nexera ® oilseed rape).
  • crops also includes plants that have been modified for the improved production of raw materials by means of genetic engineering methods by z.
  • the compounds of the formula I are also suitable for the defoliation and / or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, come into consideration.
  • compositions for the desiccation and / or defoliation of plants, processes for the preparation of these agents and methods for the desiccation and / or defoliation of plants with the compounds of formula I have been found.
  • Desiccants are the compounds of formula I in particular for dehydration of the aerial parts of crop plants such as potato, oilseed rape, sunflower and soybean but also cereals. This enables a completely mechanical harvesting of these important crops.
  • the compounds I or the herbicidal compositions containing them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-percentage aqueous, oily or other suspensions or dispersions. emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing, dusting, scattering, pouring or treating the seed or mixing with the seed.
  • the forms of application depend on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • the herbicidal compositions contain a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of pesticides.
  • thickeners ie, compounds which impart modified flowability to the formulation, ie, high-level at low viscosity and low viscosity in the agitated state
  • polysaccharides such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum ® (RT Vanderbilt) and organic and inorganic layer minerals such as Attaclay® (Engelhardt).
  • antifoam agents examples include silicone emulsions (such as, for example, Silikon® SRE, Wacker or Rhodorsil® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.
  • Bactericides may be added to stabilize the aqueous herbicidal formulation.
  • bactericides are bactericides based on diclorophene and benzyl alcohol hemiformal (Proxel® from ICI or Acticide® RS from Thor Chemie and Kathon® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS der Fa. Thor Chemie)
  • antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
  • colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned under the names rhodamine B, Cl. Pigment Red 112 and Cl. Solvent Red 1 known dyes, and pigment blue 15: 4, pigment blue 15: 3, pigment blue 15: 2, pigment blue 15: 1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 1 12, pigment red 48: 1, pigment red 48: 1, pigment red 57: 1, pigment red 53: 1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • adhesives examples include polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
  • Suitable inert additives are, for example: Mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol , Propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, eg. As amines such as N-methylpyrrolidone or water.
  • Mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example paraffin, tetrahydronaphthalene, alkylated naphthalenes or their
  • Solid carriers are mineral soils such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral soils such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour
  • alkali metal As surface-active substances (adjuvants, wetting, adhesion, dispersing and emulsifying agents), the alkali metal, alkaline earth metal, ammonium salts of aromatic sulfonic acids, e.g. Ligninsulfonklaren (eg Borrespers types, Borregaard), phenolsulfonic acids, naphthalene sulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), as well as fatty acids, alkyl and alkylaryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and Salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation
  • Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
  • Granules, e.g. Coating, impregnation and homogeneous granules can be prepared by binding the active compounds to solid carriers.
  • Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or oil dispersions the compounds of the formula I or Ia, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be made of effective substance, mesh, adhesive, Dispersing or emulsifying agent and possibly solvent or oil concentrates are prepared, which are suitable for dilution with water.
  • the concentrations of the compounds of the formula I in the ready-to-use formulations can be varied within wide limits.
  • the formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
  • the compounds I according to the invention can be formulated, for example, as follows:
  • active compound 20 parts by weight are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant, e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • a dispersant e.g. Polyvinylpyrrolidone dissolved. Dilution in water gives a dispersion.
  • the active ingredient content is 20% by weight
  • active compound 15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (for example alkylaromatics) with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion.
  • the formulation has 15% by weight active ingredient content.
  • active compound 25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (for example alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • organic solvent for example alkylaromatics
  • calcium dodecylbenzenesulfonate and castor oil ethoxylate in each case 5 parts by weight.
  • This mixture is added to water by means of an emulsifying machine (e.g., Ultraturax) in 30 parts by weight and made into a homogeneous emulsion. Dilution in water results in an emulsion.
  • the formulation has an active ingredient content of 25% by weight.
  • active compound 20 parts by weight of active compound are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient.
  • the active ingredient content in the formulation is 20% by weight.
  • Water-dispersible and water-soluble granules 50 parts by weight of active compound are finely ground with the addition of 50 parts by weight of dispersing and wetting agents and prepared by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. In the Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the formulation has an active ingredient content of 50% by weight.
  • active compound 75 parts by weight of active compound are ground with the addition of 25 parts by weight of dispersing agent and wetting agent as well as silica gel in a rotor-stator mill. Dilution in water results in a stable dispersion or solution of the active ingredient.
  • the active ingredient content of the formulation is 75% by weight.
  • 0.5 parts by weight of active compound are finely ground and combined with 99.5 parts by weight of carrier substances. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.
  • the application of the compounds I or the herbicidal compositions containing them can take place in the pre-emergence, post-emergence or together with the seed of a crop. It is also possible to apply the herbicidal compositions or active ingredients characterized in that with the herbicidal agents or active ingredients pretreated seed of a crop plant is applied. If the active ingredients are less compatible with certain crops, then application techniques may be employed whereby the herbicidal agents are sprayed by the sprayers so as not to hit the leaves of the sensitive crops as far as possible, while the active ingredients affect the leaves underneath growing undesirable plants or the uncovered floor surface (post-directed, lay-by).
  • the application of the compounds of the formula I or of the herbicidal compositions can be carried out by treating seed.
  • seed dressing seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting
  • seed dressing seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, and seed pelleting
  • the herbicidal agents can be diluted or applied undiluted.
  • seed includes seeds of all kinds, such as grains, seeds, fruits, tubers, cuttings and similar forms.
  • seed preferably describes grains and seeds here.
  • Seeds of the crops mentioned above, but also the seed of transgenic plants or plants obtained by conventional breeding methods, can be used as seed.
  • the application rates of active ingredient are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a. S.).
  • the compounds I are usually used in amounts of 0.001 to 10 kg per 100 kg of seed.
  • Safeners are chemical compounds that prevent or reduce damage to crops without significantly affecting the herbicidal activity of the compounds of formula I on undesirable plants. They can be used both before sowing (for example in seed treatments, cuttings or seedlings) as well as in the pre- or post-emergence of the crop. The safeners and the compounds of formula I can be used simultaneously or sequentially.
  • Suitable safeners are, for example, (quinoline- ⁇ -oxy) acetic acids, 1-phenyl-5-haloalkyl-1H-1, 2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5 alkyl-1H-pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N- [ [4- (aminocarbonyl) phenyl] sulfonyl] -2-benzoic acid amides, 1,8-naphthalic anhydride, 2-halo-4- (haloalkyl) -5-thiazolecarboxylic acids, phosphorothiolates and N-alkyl-O-phenylcarba
  • the compounds of formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups or with safeners and applied together.
  • Glyphosate, glyphosate isopropylammonium and glyphosate trimesium sulfosate
  • Y is phenyl or 5- or 6-membered heteroaryl as defined above, which may be substituted by one to three groups R aa ; R 21 , R 22 , R 23 , R 24 are H, halogen, or C 1 -C 4 -alkyl; X is O or NH; n 0 or 1.
  • # is the bond to the molecular skeleton; and R 21 , R 22 , R 23 , R 24 are H, Cl, F or CH 3 ; R 25 is halogen, C 1 -C 4 -alkyl or C 1 -C 4 -haloalkyl; R 26 is dC 4 alkyl; R 27 is halogen, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; R 28 is H, halogen, CrC 4 - alkyl, Ci-C 4 haloalkyl or Ci-C4-haloalkoxy; m is 0, 1, 2 or 3; X oxygen; n 0 or 1.
  • Particularly preferred compounds of the formula 2 are:
  • MSMA oleic acid, oxaziclomefon, pelargonic acid, pyributicarb, quinoclamin, triaziflam, tridiphan and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (H-10; CAS 499223-49-3 ) and its salts and esters.
  • Examples of preferred safeners C are Benoxacor, Cloquintocet, Cyometrinil, Cyprusulfamide, Dichlormid, Dicyclonon, Dietholate, Fenchlorazole, Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen, Mefenpyr, Mephenate, Naphthalic Anhydride, Oxabetrinile, 4- (Dichloroacetyl ) -1-oxa-4-azaspiro [4.5] decane (H-1 1; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (H -12; R-29148, CAS 52836-31-4).
  • the active compounds of groups b1) to b15) and the safeners C are known herbicides and safeners, see, for example, US Pat. B. The Compendium of Pesticide Common Names
  • the invention also relates to compositions in the form of a crop protection agent formulated as a 1-component composition
  • a crop protection agent formulated as a 1-component composition
  • a combination of active substances comprising at least one pyridine compound of the formula I and at least one further active ingredient, preferably selected from the active substances of groups b1 to b15, and at least one solid or liquid carrier and / or one or more surface-active substances and, if desired, one or more further auxiliaries customary for crop protection agents.
  • the invention also relates to compositions in the form of a plant protection composition formulated as a 2-component composition, comprising a first component comprising at least one pyridine compound of the formula I, a solid or liquid carrier and / or one or more surface-active substances, and a second component containing at least one further active ingredient selected from the active compounds of groups b1 to b15, a solid or liquid carrier and / or one or more surface-active substances, wherein in addition both components may also contain other, customary for crop protection agents.
  • a plant protection composition formulated as a 2-component composition, comprising a first component comprising at least one pyridine compound of the formula I, a solid or liquid carrier and / or one or more surface-active substances, and a second component containing at least one further active ingredient selected from the active compounds of groups b1 to b15, a solid or liquid carrier and / or one or more surface-active substances, wherein in addition both components may also contain other, customary for crop protection agents.
  • the weight ratio of the active compounds A: B is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and particularly preferably in the range of 1: 75 to 75: 1.
  • the weight ratio of the active compounds A: C is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and particularly preferably in the range of 1: 75 to 75: 1.
  • the relative proportions by weight of the components A: B are generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and more preferably in the range from 1: 75 to 75: 1,
  • the weight ratio of component A: C is generally in the Range of 1: 1000 to 1000: 1, preferably in the range of 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and more preferably in the range of 1: 75 to 75: 1
  • the weight ratio of the components B: C generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and particularly preferably in the range from 1: 75 to 75: 1.
  • the weight ratio of components A + B to component C is preferably within the range ranges from 1: 500 to 500: 1, in
  • compositions according to the invention containing in each case an individualized compound of the formula I and a mixing partner, or a mixture partner combination are given in the following Table B.
  • a further embodiment of the invention relates to the compositions B-1 to B-1227 listed in Table B, wherein in each case one row of Table B corresponds to a herbicidal composition comprising a compound of the formula I (component 1) individualized in the present specification. and the further active ingredient from groups b1) to b15) and / or safener C (component 2) respectively indicated in the relevant line.
  • the active ingredients in the described compositions are each preferably present in synergistically effective amounts.
  • the compounds I and the compositions according to the invention may also have a plant-strengthening effect. They are therefore suitable for mobilizing plant-own defenses against infestation by undesirable microorganisms, such as harmful fungi, but also viruses and bacteria.
  • plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of treated plants in such a way that they develop extensive resistance to these microorganisms during subsequent inoculation with undesired microorganisms.
  • the compounds I can be used to protect plants against attack by undesired microorganisms within a certain period of time after the treatment.
  • the period within which protection is provided generally extends from 1 to 28 days, preferably 1 to 14 days after Treatment of the plants with the compounds I or after treatment of the seeds, up to 9 months after sowing.
  • the compounds I and the compositions according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
  • Step 1 3-Hydroxy-pyridin-2-carbonsaure-pent.afluorphenylest.er
  • Step 2 4-Hydroxy-3- (3-trifluoromethoxyphenyl) pyrano [3,2-b] pyridin-2-one
  • a solution of 0.64 g of 3-hydroxy-pyridine-2-carboxylic acid pentafluorophenyl ester (from Step 1) and 0.5 g (3-trifluoromethoxy-phenyl) -acetyl chloride in 150 ml of acetonitrile were mixed with 3.5 g of K 2 CO 3 and stirred under N 2 atmosphere for about 12 hrs. At 20-25 ° C. After filtration, the eluate was freed from the solvent, the residue obtained was taken up in water and, after acidification, extracted to pH ⁇ 4 with CH 2 Cl 2.
  • Step 1
  • Methyl 3- [2- (2-trifluoromethyl-phenyl) -acetylamino] -pyridine-2-carboxylate 0.6 g of triethylamine were added to a solution of 0.45 g of 3-aminopyridine-2-methyl ester and 0.66 g of (2-trifluoromethylphenyl) acetyl chloride in 50 ml CH 2 Cl 2. The solution was washed after about 6 hr. Stirring at 20-25 0 C with water. After phase separation, the combined organic phases were dried, then freed from the solvent in vacuo.
  • Step 2 4-Hydroxy-3- (2-trifluoromethylphenyl) -1H- [1,5] naphthyridin-2-one.
  • 4.8 ml of a 1.0 M solution was added to a solution of 0.8 g of the ester from Step 1 in 50 ml of THF under N 2 atmosphere at -40 0 C given.
  • the mixture was diluted with water after about 15 hours of stirring at 20-25 ° C, then the solution was extracted with CH 2 Cl 2.
  • the combined organic phases were freed from the solvent in vacuo after drying. From the residue, 200 mg of the title compound were obtained by preparative HPLC (see Example 1).
  • Step 1
  • Step 3 4-Hydroxy-1-methyl-3- (2-trifluoromethylphenyl) -1H- [1,5] naphthyridin-2-one
  • the culture vessels used were plastic pots with loamy sand with about 3.0% humus as substrate.
  • the seeds of the test plants were sown separately by species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing by means of finely distributing nozzles.
  • the jars were lightly rained to promote germination and growth and then covered with clear plastic hoods until the plants had grown. This cover causes a uniform germination of the test plants, if it was not affected by the active ingredients.
  • test plants were grown depending on the growth form only to a height of from 3 to 15 cm and then treated with the suspended or emulsified in water agents.
  • the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the plants were kept species-specific at temperatures of 10 - 25 ° C and 20 - 35 ° C, respectively.
  • the trial period lasted for 2 to 4 weeks. During this time, the plants were cared for, and their response to each treatment was evaluated.
  • the rating was based on a scale of 0 to 100. 100 means no emergence of the plants or complete destruction of at least the above-ground parts and 0 no damage or normal growth course.
  • a good herbicidal activity is at values of at least 70 and a very good herbicidal activity is given at values of at least 85.
  • the plants used in the greenhouse experiments were composed of the following species:
  • the active ingredient I-6 showed at a rate of 1, 0 kg / ha and the active ingredients I-7, or I-8 at 0.5 kg / ha postemergence against AMARE a very good herbicidal activity.
  • the active compounds 1-1, and I-2 showed at a rate of 3.0 kg / ha postemergence against AVEFA a very good herbicidal activity.

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  • Organic Chemistry (AREA)
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  • Agronomy & Crop Science (AREA)
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  • Pyridine Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne des pyridines substituées de formule I, dans laquelle les variables sont telles que définies dans la description, leurs sels acceptables en agriculture, les procédés et produits intermédiaires pour la production des pyridines de formule I, les produits les contenant et leur utilisation comme herbicides, c'est-à-dire pour la lutte contre les mauvaises herbes, et un procédé de lutte de la croissance indésirable des plantes, selon lequel on laisse agir sur les plantes, leurs semences et/ou leur biotope au moins un composé pyridine de la formule I en quantité d'action herbicide.
EP09736916A 2008-10-29 2009-10-14 Pyridines substituées à action herbicide Withdrawn EP2350069A1 (fr)

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EP09736916A EP2350069A1 (fr) 2008-10-29 2009-10-14 Pyridines substituées à action herbicide

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EP08167850 2008-10-29
EP09736916A EP2350069A1 (fr) 2008-10-29 2009-10-14 Pyridines substituées à action herbicide
PCT/EP2009/063386 WO2010049269A1 (fr) 2008-10-29 2009-10-14 Pyridines substituées à action herbicide

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UY32212A (es) 2010-05-31
EP2350074A1 (fr) 2011-08-03
EP2350074B1 (fr) 2013-03-06
AU2009309837A1 (en) 2010-05-06
CN102203091A (zh) 2011-09-28
BRPI0920102A2 (pt) 2015-08-18
CN102203091B (zh) 2014-08-13
WO2010049270A1 (fr) 2010-05-06
MX2011004396A (es) 2011-05-25
EA201100661A1 (ru) 2011-12-30
CR20110266A (es) 2011-06-03
UY32211A (es) 2010-05-31
AR074069A1 (es) 2010-12-22
US8338337B2 (en) 2012-12-25
BRPI0919652A2 (pt) 2015-08-18
CL2011000955A1 (es) 2011-09-02
TW201022263A (en) 2010-06-16
JP2012506885A (ja) 2012-03-22
TW201022277A (en) 2010-06-16
JP2012506886A (ja) 2012-03-22
KR20110082058A (ko) 2011-07-15
US20110201501A1 (en) 2011-08-18
ZA201103873B (en) 2012-08-29
CN102203090A (zh) 2011-09-28
CA2741138A1 (fr) 2010-05-06
US20110224078A1 (en) 2011-09-15
WO2010049269A1 (fr) 2010-05-06
IL212536A0 (en) 2011-06-30
JP5681634B2 (ja) 2015-03-11

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