WO2011051212A1 - Utilisation de composés hétéroaromatiques en tant qu'herbicides - Google Patents

Utilisation de composés hétéroaromatiques en tant qu'herbicides Download PDF

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WO2011051212A1
WO2011051212A1 PCT/EP2010/066037 EP2010066037W WO2011051212A1 WO 2011051212 A1 WO2011051212 A1 WO 2011051212A1 EP 2010066037 W EP2010066037 W EP 2010066037W WO 2011051212 A1 WO2011051212 A1 WO 2011051212A1
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formula
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alkyl
och
methyl
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Dschun Song
Julia Major
Johannes Hutzler
Trevor William Newton
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Basf Se
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    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Definitions

  • the present invention relates to the use of heteroaromatic compounds of formula I.
  • 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, Ci-C 4 haloalkyl, ZC 3 -C 6 cycloalkyl, C 2 -C 8 alkenyl, 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'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 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 He - tero atoms selected from O, N and S, where
  • R ', R "are independently hydrogen, Ci-C 8 alkyl, Ci-C 4 -Halo- alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, ZC 3 -C 6 -cycloalkyl, Z -C 1 -C 8 -alkoxy, Z-C 1 -C 8 -haloalkoxy, ZC ( O) -R a , Z-phenyl, Z-linked 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;
  • R '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 0, 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 bb is C 1 -C 8 -alkyl and C 1 -C 6 -haloalkyl and n is 0, 1 or 2; 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. may contain;
  • X, Y independently of one another are O, S or NR 3 ;
  • R 3 is hydrogen, Ci-C 6 alkyl, Ci-C 4 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 NR'R ";
  • R c is hydrogen or one of the groups mentioned for R b ;
  • groups R A , R 3 and their sub-substituents the carbon chains and / or the cyclic groups may be partially or completely substituted by groups R b ,
  • the invention relates to novel compounds of the formula I, processes and intermediates for the preparation of the compounds of formula I and their N-oxides, their agriculturally useful salts, as well as active ingredient combinations and compositions containing them, as well as a method for controlling unwanted plant growth, in which is a herbicidally effective amount of at least one compound of formula I or an agriculturally useful salt of I on plants, their seeds and / or their habitat act.
  • 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:
  • Carboxylic 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 of -78 ° C to 120 ° C, preferably -20 ° C to 50 ° 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 (DMSO), dimethylformamide (DMF) and dimethylacetamide, more preferably halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzen
  • the bases used 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 hydroxide.
  • alkali metal 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 Methyllithium, butyllithium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and also alkali metal and alkaline earth metal alkoxides such as sodium methoxide, sodium ethanolate, potassium ethanolate, potassium tert-butoxide and dimethoxy magnesium, furthermore organic bases, eg tertiary amines such as trimethylamine, triethylamine, tributylamine, Di-isopropylethyl
  • 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 of -78 ° C to 120 ° C, preferably -20 ° C to 50 ° 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 also DMSO, DMF and dimethylacetamide, particularly preferably methylene chloride and toluene. It is also possible to use mixtures of the solvents mentioned.
  • the bases used 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, calzium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydroxides.
  • 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, calzium oxide and magnesium oxide
  • alkali metal and alkaline earth metal hydrides such as lithium hydroxides.
  • 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
  • alkali metal hydrogencarbonates such as sodium hydrogencarbonate
  • 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 as sodium, sodium, potassium, potassium tert-butoxide and Dimethoxymagnesium
  • organic bases such as tertiary amines such as trimethylamine, triethylamine, tributylamine, di-isopropylethylamine and N-methylpiperidine
  • pyridine substituted pyridines such as collidine, lutidine and 4-dimethylamin
  • 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, ⁇ , ⁇ -dialkylhydroxylamine, in particular pentafluorophenol or ⁇ , ⁇ -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 -78 ° C to 120 ° C, preferably -20 ° C to 50 ° C, in an inert organic solvent in the presence of a base, or a Lewis acid or a catalyst [see. Silverman, Richard B. J. 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 also DMSO, DMF and dimethylacetamide, particularly preferably acetonitrile and dimethylformamide. It is also possible to use mixtures of the solvents mentioned.
  • 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, calcium carbonate, cesium carbonate and rubidium carbonate and alkali metal bicarbonates 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 as sodium
  • 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 I can also be obtained via a reverse reaction sequence, ie from the reaction of the compounds of formula II with compounds.
  • 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.
  • isomeric mixtures are involved in the synthesis, separation is not necessarily required because some of the isomers may partially interconvert during processing for use or in use (e.g., under light, acid, or base action). Corresponding conversions may also take place after use, for example in the treatment of plants in the treated plant or in the harmful plant to be controlled.
  • the organic molecular moieties mentioned for the substituents of the compounds according to the invention are collective terms for individual listings of the individual group members.
  • halogenated substituents preferably carry one to five identical or different halogen atoms, in particular fluorine atoms or chlorine atoms.
  • 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-
  • 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-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, penta
  • 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,
  • Cycloalkenyl monocyclic, monounsaturated hydrocarbon groups having 3 to 6, preferably 5 to 6 carbon ring members, such as cyclopentene-1-yl, cyclopentene-3-yl, cyclohexene-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,
  • 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,
  • 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 -alkyl.
  • 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-hydroxyeth-1 -yl) ammonium, trimethylbenzylammonium.
  • ammonium cation is the pyridine nitrogen atom of the formula I quaternized by alkylation or arylation.
  • phosphonium ions preferably tri (C 1 -C 4 -alkyl) sulfonium or sulfoxonium ions, preferably tri (C 1 -C 4 -alkyl) sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate, Butyrate or trifluoroacetate.
  • 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 and G are N and E is CR c . These compounds correspond to the formula 1.1,
  • R c1 is H, alkyl, haloalkyl, in particular alkyl;
  • R c2 H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and
  • a and E are N and G is CR c . These compounds correspond to the formula I.2,
  • R c1 is H, alkyl, haloalkyl, in particular alkyl;
  • R c2 H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and
  • R 1 is selected from OH, OCH 3,
  • R 2 is phenyl which is substituted by a group selected from 2-Br, 2-CI, 2,4-CI 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-N0 2 , 2-N0 2 -4-F, 2-N0 2 -5-F, 2-N0 2 -6- F, 2-N0 2 -4-CF 3 , 2-N0 2 -5-CF 3 , 2-N0 2 -6-CF 3 , 2-N0 2 -3,6-F 2 , 2-CN, 2 CH 3 , 2-CH 3
  • X is selected from oxygen and sulfur.
  • Y is selected from oxygen and sulfur.
  • A, E and G are N.
  • group R c2 corresponds to a group R c and preferably represents H, alkyl, haloalkyl, in particular alkyl.
  • A is S and E and G is CR c . These compounds correspond to the formula I.4.
  • R c1 and R c2 each correspond to a group R c and are preferably H, alkyl, haloalkyl, in particular H (R c1 ) and alkyl (R c2 ).
  • A is CR c
  • E is N
  • G is NR c .
  • R c1 and R c2 each correspond to a group R c and preferably represents H, alkyl, optionally subst. Phenyl, in particular H (R c1 ) and alkyl and optionally subst. Phenyl (R c2 ) are.
  • a and G are CR c and E is S. These compounds correspond to the formula I.6.
  • R c1 and R c2 each correspond to a group R c and are preferably H and alkyl, in particular H.
  • R 1 is O -R A.
  • R 1 is S ( O ) n -R A , where n is preferably 0 or 2, in particular 2.
  • R 1 is O -S ( O ) n -R A , where n is preferably 0 or 2, in particular 2, such as, for example, OS (O) 2-CH 3, OS (O) 2 -C 2 H 5 , OS (0) 2 -C 3 H 7 , OS (0) 2 -C 6 H 5 or OS (0) 2- (4-CH 3 -C 6 H 4 ).
  • R 1 is O-S (O) n -NR'R ii , in particular with the groups NR'R "which are preferably mentioned below.
  • R 1 is NR'R ", in which R'R" in particular has the following preferred meanings or particularly preferably stands for diethyl.
  • R A is in particular H, C 1 -C 6 -alkylcarbonyl, such as C (O) CH 3 , C (O) CH 2 CH 3 ,
  • Benzoyl such as C (O) C 6 H 5 ,
  • Heteroaryl such as pyridine, which is bonded via a carbonyl group.
  • R A is particularly preferably H or C 1 -C 6 -alkylcarbonyl.
  • R A is selected from the group consisting of H, OCH 3 , C ( O ) CH 3 , C (O) CH 2 CH 3 , C (O) CH (CH 3 ) 2 , C (O) C (CH 3 ) 3 , C (0) -cC 3 H 5 , C (O) -C 6 H 5 , C (O) -CH 2 C 6 H 5 , C (O) CH 2 Cl, C (0) 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'R ". In a further preferred embodiment of the invention, R A is
  • R' and R " are also independently of one another C 1 -C 4 -alkoxy , C 1 -C 4 -haloalkoxy and C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl in question, 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) especially 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 (CH 3 ) 2 .
  • NR'R is 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-CI 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 .
  • halogen CH 3
  • halogen dC 2 -alkyl halo-C 1 -C 2 -alkoxy and carboxyl
  • carboxyl such as 2-Cl, 6-COOH-C 6 H 3
  • NR'R are NH heteroaryl, heteroaryl preferably being one of the preferred heteroaromatic groups below, in particular triazinyl, pyrimidinyl or triazolopyrimidinyl, such as [1,2,4] triazolo [1,5-a] pyridine.
  • 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.
  • 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 nitrogen atoms as ring members and which is unsubstituted or may have 1 or 2 substituents selected from R b .
  • R b 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 nitrogen atoms as ring members and which is unsubstituted or may have 1 or 2 substituents selected from R b .
  • 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, isoxazol-5-yl, isothiazol-3-yl, isothiazole-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 , Thiazol-4-yl and
  • 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, pyrimidin-5-yl, pyridazin-4-yl, pyrazine 2-yl, [1 H] -tetrazol-5-yl and [2H] -tetrazol-5-yl, wherein the heterocycles 1 or 2 mentioned here by way of example from R b may have selected substituents.
  • preferred groups 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
  • 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 For IA are described:
  • 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 , OCF 3 , CF 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.
  • X is S.
  • X is NR 3 .
  • Y is O.
  • Y is NR 3 .
  • Y stands for S.
  • CH 2 CH 2 CH 2 C (CH 3 ) CH 2 , or 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 More preferably R 3 is haloalkyl. If both X and Y are NR 3 , the groups R 3 are independently selected.
  • 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.
  • Combination of R 1 , R 5 and (R 6 ) n for a compound corresponds in each case to one row of Table A.
  • 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:
  • Garis Picea abies, Pinus spp., 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, Seeale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (see vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
  • 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 257 993, US Pat. No. 5,013,659) or imidazolinones (see, for example, US Pat. Nos. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, US Pat.
  • HPPD hydroxyphenylpyruvate dioxygenase
  • ALS acetolactate synthase
  • Sulfonylureas EP-A 257 993, US Pat. No. 5,013,659
  • imidazolinones see, for example, US Pat. Nos. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, US Pat.
  • WO 03/13225, WO 03/14356, WO 04/16073), enolpyruvylshikimate-3-phosphate synthase (EPSPS) -inhibitors such. Glyphosate (see, for example, WO 92/00377), glutamine synthetase (GS) inhibitors such as. Glufosinate (see eg EP-A 242 236, EP-A 242 246) or oxynil herbicides (see eg US 5,559,024).
  • mutagenesis With the help of classical breeding methods (mutagenesis) numerous crops, eg. As Clearfield® rapeseed, which produces a tolerance to imidazolinones, z. As imazamox, have.
  • crop plants such as soybean, produces cotton, corn, beets and rape, which are resistant to glyphosate or glufosinate, and sold under the trade name RoudupReady ® (glyphosate) and Liberty Link ® (glufosinate) are available.
  • 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. B. Insecticidal proteins of Bacillus spp., In particular of B. thuringiensis, such as the endotoxins CrylAb, CrylAc, Cryl F, Cry1 Fa2, 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; Agglutinin; Proteinase inhibitors, e.g. B. trypsin inhibitors, serine protease inhibitors, pata tin, cystatin or papain inhibitors; Ribosome Inactivating Proteins (RIPs), e.g.
  • RIPs Ribosome Inactivating Proteins
  • Steroid metabolizing enzymes e.g. 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyl transferase, cholesterol oximes, ecdysone inhibitors or HMG CoA reductase
  • ion channel blocker e.g. B. inhibitors of sodium or calcium
  • 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,
  • the methods for producing these genetically modified plants are known in the art and z. As set forth in the publications mentioned above. Many of the aforementioned toxins confer on the plants that produce them a tolerance to pests of all taxonomic arthropod classes, in particular to beetles (Coeleropta), diptera (Diptera) and butterflies (Lepidoptera) and nematodes (Nematoda).
  • 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.
  • B. so-called pathogenesis-related proteins PR proteins, see EP-A 0 392 225
  • 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 z.
  • yield eg biomass, grain yield, starch, oil or protein content
  • tolerance to drought salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens may be increased.
  • crops also includes plants whose ingredients have been modified in particular to improve the human or animal diet using genetic engineering methods by z. (- rape, for example Nexera ®.) Produce as oil plants producing health long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids.
  • 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 allows a completely mechanical harvesting of these important crops.
  • the compounds I or the herbicidal compositions containing them for example in the form of directly sprayable aqueous solutions, powders, suspensions, 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 treatment of 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.
  • auxiliaries examples include inert excipients, solid carriers, surfactants (such as dispersants protective colloids, emulsifiers, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze, defoamers, if necessary dyes and adhesives for seed formulations.
  • 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).
  • antifoams 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) as well as 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, C.I. Pigment Red 1 12 and C.I. Solvent Red 1 known dyes, as well as 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: 2, 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 are 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, e.g. 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.
  • amines such as N-methylpyrrolidone or water.
  • Solid carriers are mineral earths 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 earths 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
  • surfactants adjuvants, wetting agents, tackifiers, dispersants and emulsifiers
  • the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Ligninsulfonklaren (eg, Borrespers types, Borregaard), phenolsulfonic acids, naphthalenesulfonic (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE)
  • fatty acids alkyl and alkylarylsulfonates, 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 products of naphthalen
  • B methyl cellulose
  • hydrophobically modified starches polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, lupamine types), polyethylenimine (BASF SE, Lupasol types), polyvinylpyrrolidone and their copolymers into consideration.
  • 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 heated in water by means of wetting agents, tackifiers, dispersants or emulsifiers. be homogenized.
  • concentrates consisting of active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, 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.
  • active compound 50 parts by weight are added with the addition of 50 parts by weight of dispersing and wetting agents. with a finely ground and produced by means of technical equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. 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 and wetting agents and silica gel in a rotor-Strator 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 carriers. 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 be carried out in the pre-emergence, postemergence 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 crop if possible, while the active ingredients affect the leaves underneath growing undesirable plants or the uncovered floor surface (post-directed, lay-by). In a further embodiment, the application of the compounds of the formula I or of the herbicidal compositions can be carried out by treating seed.
  • the treatment of seed comprises essentially all techniques familiar to the skilled worker (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula according to the invention I or agents produced therefrom.
  • the herbicidal agents can be diluted or applied undiluted.
  • seed includes seeds of all kinds, e.g. Grains, seeds, fruits, tubers, cuttings and similar forms.
  • seed preferably describes grains and seeds here.
  • Seeds of the abovementioned crops but also the seeds of transgenic or obtained by conventional breeding methods plants can be used as seeds.
  • 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-8-oxy) acetic acids, 1-phenyl-5-haloalkyl-1H-1, 2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl- 1 H-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-phenylc
  • 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.
  • 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.
  • 1, 2,4-thiadiazoles, 1, 3,4-thiadiazoles, amides, aminophosphoric acid and their derivatives, amides are used as the mixing partners.
  • notriazoles anilides, aryloxy / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2- (hetaroyl / aroyl) -1, 3-cyclohexanediones, heteroaryl-aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and derivatives thereof, dihydrobenzofurans, dihydro-furan-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,
  • herbicides which can be used in combination with the compounds of the formula I according to the present invention are:
  • Bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium; b8) from the group of DHP synthase inhibitors: asulam;
  • Acetochlor alachlor, anilofos, butachlor, cafenstrol, dimethachlor, dimethanamide, dimethamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metachachlor, metolachlor-S, naproanilide, napropamide, pethoxamide, piperophos, pretilachlor, propachlor, Propisochlor, Pyroxasulfone (KIH-485) and Thenylchlor;
  • 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.
  • R 2 , 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, Ci-C 4 - alkyl, Ci-C 4 haloalkyl or Ci-C4-haloalkoxy;
  • m is 0, 1, 2 or 3;
  • Preferred compounds of formula 2 have the following Be
  • Particularly preferred compounds of the formula 2 are: 3- [5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfonyl] -4-fluoro-5,5-dimethyl-4,5-dihydro-isoxazole (2-1); 3 - ⁇ [5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] -fluoro-methanesulfonyl ⁇ -5,5-dimethyl-4,5 dihydro-isoxazole (2- 2); 4- (4-Fluoro-5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonylmethyl) -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-3 ); 4 - [(5,5-dimethyl-4,5-dihydroisoxazol-3
  • auxin transport inhibitors diflufenzopyr, diflufenzopyrsodium, naptalam and naptalam sodium;
  • 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, Fluoxofenim, 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).
  • De agents of groups b1) to b15) and the safeners C are known herbicides and safeners, see, for. 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, comprising a combination of active substances comprising at least one 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 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 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 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 particularly preferably in the range of 1: 75 to 75: 1, the weight ratio of Component A: C 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 particularly preferably in the range of 1: 75 to 75: 1, and the weight ratio of the components B: C usually 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 components A + B to component C is preferably in the range from 1: 500 to 500: 1, in particular
  • 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 seed, up to 9 months after sowing.
  • the compounds I and the compositions according to the invention are also suitable for increasing crop yield.
  • Step 1 Ethyl 3-methyl-5- [2- (2-trifluoromethylphenyl) acetylamino] -3H-imidazole-4-carboxylate
  • Step 3 7- (2,2-Difluoroethoxy) -1-methyl-6- (2-trifluoromethyl-phenyl) -1,4-dihydro-imidazo [4,5-b] pyridin-5-one
  • Step 1 3- (4-Benzyloxy-2-methyl-2H-pyrazol-3-yl) -3-hydroxy-2- (2-trifluoromethyl-phenyl) -acrylic acid methyl ester
  • 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 active ingredient I-5 showed at a rate of 3.0 kg / ha postemergence against SETIT a very good herbicidal activity.

Abstract

L'invention concerne l'utilisation de composés hétéroaromatiques de formule I, dans laquelle les variables sont définies selon la description, et de leurs sels adaptés à l'agriculture en tant qu'herbicides. L'invention concerne également de nouveaux composés de formule I, des procédés et des produits intermédiaires pour la production des composés de formule I et de produits les contenant, ainsi qu'un procédé de lutte contre la croissance de plantes indésirables, qui consiste à laisser agir une quantité à efficacité herbicide d'au moins un composé de formule I sur des plantes, leurs graines et/ou leur habitat.
PCT/EP2010/066037 2009-10-28 2010-10-25 Utilisation de composés hétéroaromatiques en tant qu'herbicides WO2011051212A1 (fr)

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012028582A1 (fr) * 2010-09-01 2012-03-08 Bayer Cropscience Ag Cétosultames et dicétopyridines herbicides
US8440594B2 (en) 2010-03-23 2013-05-14 Basf Se Pyridothiazines having herbicidal action
WO2013144096A1 (fr) * 2012-03-27 2013-10-03 Bayer Intellectual Property Gmbh Thiazolopyridinones substituées par un phényle, à action herbicide et insecticide
US8575068B2 (en) 2010-03-23 2013-11-05 Basf Se Pyrazinothiazines having herbicidal action
US8809535B2 (en) 2010-03-23 2014-08-19 Basf Se Substituted pyridines having herbicidal action
US8921273B2 (en) 2010-03-23 2014-12-30 Basf Se Substituted pyridazines having herbicidal action
GB2525270A (en) * 2013-12-05 2015-10-21 Syngenta Ltd Herbicidal compounds
WO2016102253A1 (fr) * 2014-12-22 2016-06-30 Syngenta Participations Ag Thiazolopyridinones en tant qu'herbicides
JP2018515469A (ja) * 2015-04-30 2018-06-14 シンジェンタ パーティシペーションズ アーゲー 除草性化合物
WO2022078403A1 (fr) * 2020-10-15 2022-04-21 江苏先声药业有限公司 Composé de pyridone substitué et application

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US8921273B2 (en) 2010-03-23 2014-12-30 Basf Se Substituted pyridazines having herbicidal action
US8440594B2 (en) 2010-03-23 2013-05-14 Basf Se Pyridothiazines having herbicidal action
US8575068B2 (en) 2010-03-23 2013-11-05 Basf Se Pyrazinothiazines having herbicidal action
US8809535B2 (en) 2010-03-23 2014-08-19 Basf Se Substituted pyridines having herbicidal action
CN103189376A (zh) * 2010-09-01 2013-07-03 拜耳知识产权有限责任公司 具有除草活性的酮基磺内酰胺和二酮基吡啶
JP2013536818A (ja) * 2010-09-01 2013-09-26 バイエル・インテレクチユアル・プロパテイー・ゲー・エム・ベー・ハー 除草活性を有するケトスルタム類及びジケトピリジン類
WO2012028582A1 (fr) * 2010-09-01 2012-03-08 Bayer Cropscience Ag Cétosultames et dicétopyridines herbicides
US8686000B2 (en) 2010-09-01 2014-04-01 Bayer Cropscience Ag Herbicidally active ketosultams and diketopyridines
US20150045217A1 (en) * 2012-03-27 2015-02-12 Bayer Intellectual Property Gmbh Herbicidally and Insecticidally Active Thiazolopyridinones
CN104350059A (zh) * 2012-03-27 2015-02-11 拜耳知识产权有限责任公司 具有除草和杀虫活性的噻唑并吡啶酮
WO2013144096A1 (fr) * 2012-03-27 2013-10-03 Bayer Intellectual Property Gmbh Thiazolopyridinones substituées par un phényle, à action herbicide et insecticide
JP2015512906A (ja) * 2012-03-27 2015-04-30 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ 除草活性及び殺虫活性を有するチアゾロピリジノン類
US9307767B2 (en) 2012-03-27 2016-04-12 Bayer Intellectual Property Gmbh Herbicidally and insecticidally active thiazolopyridinones
CN104350059B (zh) * 2012-03-27 2016-12-07 拜耳知识产权有限责任公司 具有除草和杀虫活性的噻唑并吡啶酮
GB2525270A (en) * 2013-12-05 2015-10-21 Syngenta Ltd Herbicidal compounds
WO2016102253A1 (fr) * 2014-12-22 2016-06-30 Syngenta Participations Ag Thiazolopyridinones en tant qu'herbicides
CN107108654A (zh) * 2014-12-22 2017-08-29 先正达参股股份有限公司 作为除草剂的噻唑并吡啶酮
JP2018515469A (ja) * 2015-04-30 2018-06-14 シンジェンタ パーティシペーションズ アーゲー 除草性化合物
US10512269B2 (en) 2015-04-30 2019-12-24 Syngenta Participations Ag Herbicidal compounds
CN111484509A (zh) * 2015-04-30 2020-08-04 先正达参股股份有限公司 除草化合物
WO2022078403A1 (fr) * 2020-10-15 2022-04-21 江苏先声药业有限公司 Composé de pyridone substitué et application

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