WO2011051212A1 - Use of heteroaromatic compounds as herbicides - Google Patents

Use of heteroaromatic compounds as herbicides Download PDF

Info

Publication number
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
Authority
WO
WIPO (PCT)
Prior art keywords
formula
compounds
alkyl
och
methyl
Prior art date
Application number
PCT/EP2010/066037
Other languages
German (de)
French (fr)
Inventor
Dschun Song
Julia Major
Johannes Hutzler
Trevor William Newton
Original Assignee
Basf Se
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Basf Se filed Critical Basf Se
Publication of WO2011051212A1 publication Critical patent/WO2011051212A1/en

Links

Classifications

    • 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

The invention relates to the use, as herbicides, of heteroaromatic compounds of the formula I, wherein the variables are defined according to the description, and of the agriculturally suitable salts thereof, to novel compounds of the formula I, methods and intermediate products for producing the compounds of formula I and agents comprising same, and to a method for treating undesired plant growth, wherein a herbicidally effective quantity of at least one compound of formula I is allowed to act on plants, the seeds thereof, and/or the environment thereof.

Description

Verwendung heteroaromatischer Verbindungen als Herbizide  Use of heteroaromatic compounds as herbicides
Beschreibung vorliegende Erfindung betrifft die Verwendung heteroaromatischer Verbindungen Formel I
Figure imgf000002_0001
Description: The present invention relates to the use of heteroaromatic compounds of formula I.
Figure imgf000002_0001
die Variablen folgende Bedeutung haben  the variables have the following meaning
0-RA, S(0)n-RA, 0-S(0)n-RA oder NR'R";0-R A , S ( O ) n -R A , O -S ( O ) n -R A or NR'R ";
Figure imgf000002_0002
RA Wasserstoff, Ci-C4-Alkyl, Z-C3-C6-Cycloalkyl, Ci-C4-Haloalkyl, C2-C6-Al- kenyl, Z-C3-C6-Cycloalkenyl, C2-C6-Alkinyl, Z-(Tri-Ci-C4-alkyl)silyl,
Figure imgf000002_0002
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,
Z-C(=0)-Ra, Z-NR'-C(0)-NRiRii, Z-P(=0)(Ra)2, NR'R", 3- bis 7-gliedriger monocyclischer oder 9- oder 10-gliedriger bicyclischer gesättigter, ungesättigter oder aromatischer Heterocyclus, enthaltend 1 , 2, 3 oder 4 Hetero- atome ausgewählt aus O, N und S, der teilweise oder vollständig durch Gruppen Ra und/oder Rb substituiert sein kann, ZC (= O) -R a , Z-NR'-C (O) -NR i R ii , ZP (= O) (R a ) 2 , NR'R ", 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 which may be partially or completely substituted by groups R a and / or R b ,
Ra Wasserstoff, OH, Ci-C8-Alkyl, Ci-C4-Haloalkyl, Z-C3-C6-Cycloalkyl, C2-C8-Alkenyl, Z-C5-C6-Cycloalkenyl, C2-C8-Alkinyl, Z-Ci-C6-Alkoxy, Z-Ci-C4-Haloalkoxy, Z-C3-C8-Alkenyloxy, Z-C3-C8-Alkinyloxy, NR'R", Ci-C6-Alkylsulfonyl, Z-(Tri-Ci-C4-alkyl)silyl, Z-Phenyl, Z-Phenoxy, Z-Phenylamino und 5- oder 6-gliedriger monocyclischer oder 9- oder 10-gliedriger bicyclischer Heterocyclus, enthaltend 1 , 2, 3 oder 4 He- teroatome ausgewählt aus O, N und S, wobei die cyclischen Gruppen unsubstituiert oder durch 1 , 2, 3, 4 oder 5 Gruppen Rb substituiert sind, bedeutet; 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, wherein the cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or 5 groups R b , means;
R',R" unabhängig voneinander Wasserstoff, Ci-C8-Alkyl, Ci-C4-Halo- alkyl, C3-C8-Alkenyl, C3-C8-Alkinyl, Z-C3-C6-Cycloalkyl, Z-Ci-C8- Alkoxy, Z-Ci-C8-Haloalkoxy, Z-C(=0)-Ra, Z-Phenyl, über Z gebundener 3- bis 7-gliedriger monocyclischer oder 9- oder 10- gliedriger bicyclischer gesättigter, ungesättigter oder aromatischer Heterocyclus, enthaltend 1 , 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S; 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' und R" können auch gemeinsam mit dem N-Atom, an das sie gebunden sind, einen 5- oder 6-gliedrigen monocyclischen oder 9- oder 10-gliedrigen bicyclischer Heterocyclus bilden, enthaltend 1 , 2, 3 oder 4 Heteroatome ausgewählt aus O, N und 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 eine kovalente Bindung oder Ci-C4-Alkylen; Z is a covalent bond or C 1 -C 4 -alkylene;
n 0, 1 oder 2;  n is 0, 1 or 2;
R2 Phenyl, Naphthyl oder und 5- oder 6-gliedriger monocyclischer oder 9- oder 10- gliedriger bicyclischer aromatischer Heterocyclus, enthaltend 1 , 2, 3 oder 4 Hete- roatome ausgewählt aus O, N und S, wobei die cyclischen Gruppen unsubstitu- iert oder durch 1 , 2, 3 oder 4 Gruppen Rb substituiert sind, bedeutet; 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 ;
Rb unabhängig voneinander Z-CN, Z-OH, Z-NO2, Z-Halogen, Ci-Cs-Alkyl, d- C4-Haloalkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, Z-Ci-C8-Alkoxy, Z-Ci-C8-Halo- alkoxy, Z-C3-Cio-Cycloalkyl, 0-Z-C3-Cio-Cycloalkyl, Z-C(=0)-Ra, NR'R'',R b independently of one another Z-CN, Z-OH, Z-NO 2 , Z-halogen, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, Z -C 1 -C 8 alkoxy, Z-C 1 -C 8 -haloalkoxy, ZC 3 -Cio-cycloalkyl, O-ZC 3 -Cio-cycloalkyl, ZC (= O) -R a , NR'R '',
Z-(Tri-Ci-C4-alkyl)silyl, Z-Phenyl und S(0)nRbb, wobei Z- (tri-Ci-C 4 alkyl) silyl, phenyl and Z-S (0) n R bb, wherein
Rbb Ci-C8-Alkyl und Ci-C6-Haloalkyl bedeutet und n für 0, 1 oder 2 steht; Rb kann auch gemeinsam mit der an das benachbarte C-Atom gebundene Gruppe Rb einen fünf- oder sechsgliedrigen gesättigten, teilweise oder vollständig un- gesättigten Ring bilden, der neben Kohlenstoff- 1 , 2 oder 3 Heteroatome ausgewählt aus O, N und S enthalten kann; 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 unabhängig voneinander O, S oder N-R3; X, Y independently of one another are O, S or NR 3 ;
R3 Wasserstoff, Ci-C6-Alkyl, Ci-C4-Haloalkyl, C2-C6-Alkenyl, C3-C6-Alkinyl,R 3 is hydrogen, Ci-C 6 alkyl, Ci-C 4 haloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 alkynyl,
Z-C3-Cio-Cycloalkyl, Ci-C6-Alkoxy-Ci-C6-alkyl, Ci-C6-Cyanoalkyl, Z-Phenyl, Z-C(=0)-Ra2 und Tri-Ci-C4-alkylsilyl; ZC 3 -Cio cycloalkyl, Ci-C 6 alkoxy-C 6 alkyl, Ci-C 6 cyanoalkyl, phenyl-Z, Z is C (= 0) -R a2 and tri-Ci-C4-alkylsilyl;
Ra2 Ci-C6-Alkyl, Ci-C4-Haloalkyl, Z-Ci-C6-Alkoxy, Z-Ci-C4-Haloalkoxy und NR'R"; 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 ";
A,E,G O, N, S und C-Rc, wobei mindestens eine Gruppe davon nicht C-Rc bedeutet und ein N durch Rc substituiert ist, A, E, GO, N, S and CR c , wherein at least one group thereof is not CR c and one N is substituted by R c ,
mit der Maßgabe, dass E nicht für O oder S steht, wenn mindestens eine Gruppe aus A und G für O oder S steht,  with the proviso that E is not O or S if at least one of A and G is O or S,
Rc Wasserstoff oder eine der bei Rb genannten Gruppen; R c is hydrogen or one of the groups mentioned for R b ;
wobei in Gruppen RA, R3 und deren Untersubstituenten die Kohlenstoffketten und/oder die cyclischen Gruppen teilweise oder vollständig durch Gruppen Rb substituiert sein können, in 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 ,
sowie deren N-Oxide und landwirtschaftlich geeignete Salze and their N-oxides and agriculturally suitable salts
als Herbizide. as herbicides.
Außerdem betrifft die Erfindung neue Verbindungen der Formel I, Verfahren und Zwischenprodukte zur Herstellung der Verbindungen der Formel I und deren N-Oxide, deren landwirtschaftlich brauchbaren Salze, sowie sie enthaltende Wirkstoffkombinationen und sie enthaltende Mittel, sowie ein Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, bei dem man eine herbizid wirksame Menge mindestens einer Verbindung der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I auf Pflanzen, deren Samen und/oder deren Lebensraum einwirken läßt. In addition, 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.
Weitere Ausführungsformen der vorliegenden Erfindung sind den Ansprüchen, der Beschreibung und den Beispielen zu entnehmen. Es versteht sich, dass die vorstehend genannten und die nachstehend noch zu erläuternden Merkmale des erfindungsgemäßen Gegenstandes nicht nur in der jeweils angegebenen Kombination, sondern auch in anderen Kombinationen verwendbar sind, ohne den Rahmen der Erfindung zu verlassen. In WO 2008/009908 und WO 2008/071918 werden herbizide Pyridopyrazine beschrieben, ihre herbizide Wirkung bei niedrigen Aufwandmengen, bzw. Verträglichkeit gegenüber Kulturpflanzen bleibt jedoch verbesserungsbedürftig. Eine Aufgabe der vorliegenden Erfindung ist die Bereitstellung von Verbindungen mit herbizider Wirkung. Insbesondere sollen Wirkstoffe zur Verfügung gestellt werden, die eine hohe herbizide Wirkung, insbesondere bereits bei niedrigen Aufwandmengen, aufweisen und deren Verträglichkeit gegenüber Kulturpflanzen für eine kommerzielle Verwertung hinreichend ist. Further embodiments of the present invention can be taken from the claims, the description and the examples. It is understood that the features mentioned above and those yet to be explained of the subject matter according to the invention can be used not only in the particular combination specified, but also in other combinations, without departing from the scope of the invention. In WO 2008/009908 and 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. In particular, 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.
Diese und weitere Aufgaben werden durch die eingangs definierten Verbindungen der Formel I und durch ihre N-Oxide, sowie deren landwirtschaftlich geeigneten Salze gelöst.  These and other objects are achieved by the compounds of the formula I defined above and by their N-oxides, as well as their agriculturally suitable salts.
Die erfindungsgemäßen Verbindungen können analog der in WO 2008/009908 und WO 2008/071918 beschriebenen Syntheserouten nach Standardverfahren der organischen Chemie hergestellt werden, beispielsweise nach der folgenden Syntheseroute: 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:
Carbonsäuren der Formel II können mit Carbonylverbindungen der Formel III zu Verbindungen der Formel IV umgesetzt werden. In Formeln II und III haben die Variablen die für Formel I angegebene Bedeutung. Die Gruppe Hai steht für ein Halogenatom oder eine andere geeignete nucleophile Abgangsgruppe, wie Alkoxy oder Phenoxy. Carboxylic acids of the formula II can be reacted with carbonyl compounds of the formula III to give compounds of the formula IV. In formulas II and III, 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.
Figure imgf000004_0001
Figure imgf000004_0001
Diese Umsetzung erfolgt üblicherweise bei Temperaturen von -78 °C bis 120°C, vorzugsweise -20°C bis 50°C, in einem inerten organischen Lösungsmittel in Gegenwart einer Base wie z. B. Triethylamin (vgl. J. Agric. and Food Chem. 1994, 42(4), 1019 - 1025.), eines Katalysators wie z. B. Dicyclohexylcarbodiimid (vgl. Egyptian Journal of Chemistry 1994, 37(3), 273-282.) oder anderer bekannter Kupplungsreagenzien.  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.
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Petrolether, aromatische Kohlenwasserstoffe wie Toluol, o-, m- und p- Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert.-Butylmethylether, Dioxan, Anisol und Tetrahydrofuran, Nitrile wie Acetonitril und Propionitril, Ketone wie Aceton, Methylethyl- keton, Diethylketon und tert.-Butylmethylketon, sowie Dimethylsulfoxid (DMSO), Di- methylformamid (DMF) und Dimethylacetamid, besonders bevorzugt halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol. Es können auch Gemische der genannten Lösungsmittel verwendet werden.  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 chlorobenzene. It is also possible to use mixtures of the solvents mentioned.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdalkalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Cal- ziumhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Cal- ziumoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calziumhydrid, Alkalimetallamide wie Lithium- amid, Natriumamid und Kaliumamid, Alkalimetall- und Erdalkalimetallcarbonate wie Lithiumcarbonat, Kaliumcarbonat und Calziumcarbonat sowie Alkalimetallhydrogencar- bonate wie Natriumhydrogencarbonat, metallorganische Verbindungen, insbesondere Alkalimetallalkyle wie Methyllithium, Butyllithium und Phenyllithium, Alkylmagnesiumha- logenide wie Methylmagnesiumchlorid sowie Alkalimetall- und Erdalkalimetallalkohola- te wie Natriummethanolat, Natriumethanolat, Kaliumethanolat, Kalium- tert.-Butanolat und Dimethoxymagnesium, außerdem organische Basen, z.B. tertiäre Amine wie Tri- methylamin, Triethylamin, Tributylamin, Di-isopropylethylamin und N-Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4-Dimethylaminopyridin sowie bicyclische Amine in Betracht. Besonders bevorzugt werden tertiäre Amine wie Tri- methylamin, Triethylamin, Tributylamin, Di-isopropylethylamin. Die Basen werden im allgemeinen in katalytischen Mengen eingesetzt, sie können aber auch äquimolar, im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden. 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-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are 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.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Die Verbindungen der Formel IV werden durch Einführung einer Abgangsgruppe L1 aktiviert. Als Abgangsgruppen L1 kommen allgemein solche Gruppen in Frage, die die Elektrophilie der Carbonylgruppe erhöhen, beispielsweise O-Alkyl, O-Aryl, Halogenide, aktivierte Ester oder Aldehyde (wie z. B. Weinreb-Amid), insbesondere Pentafluorphe- noxy. 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.
Figure imgf000005_0001
Figure imgf000005_0001
Diese Umsetzung erfolgt üblicherweise bei Temperaturen von -78 °C bis 120°C, vorzugsweise -20°C bis 50°C, in einem inerten organischen Lösungsmittel in Gegenwart einer Base wie z. B. Triethylamin (vgl. J. Agric. and Food Chem. 1994, 42(4), 1019 - 1025.), eines Katalysators wie z. B. Dicyclohexylcarbodiimid (vgl. Egyptian Journal of Chemistry 1994, 37(3), 273-282) oder anderer bekannter Kupplungsreagenzien.  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.
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Petrolether, aromatische Kohlenwasserstoffe wie Toluol, o-, m- und p- Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert.-Butylmethylether, Dioxan, Anisol und Tetrahydrofuran, Nitrile wie Acetonitril und Propionitril, Ketone wie Aceton, Methylethyl- keton, Diethylketon und tert.-Butylmethylketon, sowie DMSO, DMF und Dimethylacet- amid, besonders bevorzugt Methylenchlorid und Toluol. Es können auch Gemische der genannten Lösungsmittel verwendet werden.  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.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Erdalkalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Calzi- umhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Calzi- umoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhyd- rid, Natriumhydrid, Kaliumhydrid und Calziumhydrid, Alkalimetallamide wie Lithium- amid, Natriumamid und Kaliumamid, Alkalimetall- und Erdalkalimetallcarbonate wie Lithiumcarbonat, Kaliumcarbonat und Calziumcarbonat sowie Alkalimetallhydrogencar- bonate wie Natriumhydrogencarbonat, metallorganische Verbindungen, insbesondere Alkalimetallalkyle wie Methyllithium, Butyllithium und Phenyllithium, Alkylmagnesiumha- logenide wie Methylmagnesiumchlorid sowie Alkalimetall- und Erdalkalimetallalkohola- te wie Natriummethanolat, Natriumethanolat, Kaliumethanolat, Kalium- tert.-Butanolat und Dimethoxymagnesium, außerdem organische Basen, z.B. tertiäre Amine wie Tri- methylamin, Triethylamin, Tributylamin, Di-isopropylethylamin und N-Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4-Dimethylaminopyridin sowie bicyclische Amine in Betracht. Besonders bevorzugt werden Alkalimetall- und Erdalkalimetallcarbonate wie Lithiumcarbonat, Kaliumcarbonat, Calziumcarbonat, Cäsiumcar- bonat und Rubidiumcarbonat. Die Basen werden im allgemeinen in katalytischen Mengen eingesetzt, sie können aber auch äquimolar, im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden. 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. chloride, 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, 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, also 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-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are 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.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt. Als Agenz H-L1 kommen Alkohole, ggf. subst. Phenole, Ν,Ο-Dialkylhydroxylamin, insbesondere Pentafluorphenol oder Ν,Ο-Dimethylhydroxylamin in Frage. The starting materials are generally reacted with one another in equimolar amounts. As agent HL 1 are alcohols, optionally subst. Phenols, Ν, Ο-dialkylhydroxylamine, in particular pentafluorophenol or Ν, Ο-dimethylhydroxylamine in question.
Die Verbindungen der Formel V werden zu den Verbindungen der Formel I cyclisiert. The compounds of formula V are cyclized to the compounds of formula I.
Figure imgf000006_0001
Figure imgf000006_0001
Diese Umsetzung erfolgt üblicherweise bei Temperaturen von -78°C bis 120°C, vorzugsweise -20°C bis 50°C, in einem inerten organischen Lösungsmittel in Gegenwart einer Base, bzw. einer Lewissäure oder eines Katalysators [vgl. Silverman, Richard B. J. Am. Chem. Soc. 1981 , 103(13), 3910].  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].
Geeignete Lösungsmittel sind aliphatische Kohlenwasserstoffe wie Pentan, Hexan, Cyclohexan und Petrolether, aromatische Kohlenwasserstoffe wie Toluol, o-, m- und p- Xylol, halogenierte Kohlenwasserstoffe wie Methylenchlorid, Chloroform und Chlorbenzol, Ether wie Diethylether, Diisopropylether, tert.-Butylmethylether, Dioxan, Anisol und Tetrahydrofuran, Nitrile wie Acetonitril und Propionitril, Ketone wie Aceton, Methylethyl- keton, Diethylketon und tert.-Butylmethylketon, sowie DMSO, DMF und Dimethylacet- amid, besonders bevorzugt Acetonitril und Dimethylformamid. Es können auch Gemische der genannten Lösungsmittel verwendet werden.  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.
Als Basen kommen allgemein anorganische Verbindungen wie Alkalimetall- und Er- dalkalimetallhydroxide wie Lithiumhydroxid, Natriumhydroxid, Kaliumhydroxid und Cal- ziumhydroxid, Alkalimetall- und Erdalkalimetalloxide wie Lithiumoxid, Natriumoxid, Cal- ziumoxid und Magnesiumoxid, Alkalimetall- und Erdalkalimetallhydride wie Lithiumhydrid, Natriumhydrid, Kaliumhydrid und Calziumhydrid, Alkalimetallamide wie Lithium- amid, Natriumamid und Kaliumamid, Alkalimetall- und Erdalkalimetallcarbonate wie Lithiumcarbonat, Kaliumcarbonat, Calziumcarbonat, Cäsiumcarbonat und Rubidium- carbonat sowie Alkalimetallhydrogencarbonate wie Natriumhydrogencarbonat, metallorganische Verbindungen, insbesondere Alkalimetallalkyle wie Methyllithium, Butylli- thium und Phenyllithium, Alkylmagnesiumhalogenide wie Methylmagnesiumchlorid sowie Alkalimetall- und Erdalkalimetallalkoholate wie Natriummethanolat, Natriumetha- nolat, Kaliumethanolat, Kalium- tert.-Butanolat und Dimethoxymagnesium, außerdem organische Basen, z.B. tertiäre Amine wie Trimethylamin, Triethylamin, Tributylamin, Di-isopropylethylamin und N-Methylpiperidin, Pyridin, substituierte Pyridine wie Collidin, Lutidin und 4-Dimethylaminopyridin sowie bicyclische Amine in Betracht. Besonders bevorzugt werden Alkalimetall- und Erdalkalimetallcarbonate wie Lithiumcarbonat, Kaliumcarbonat, Calziumcarbonat, Cäsiumcarbonat und Rubidiumcarbonat. 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, sodium ethanoate, potassium, potassium tert Butanolate and Dimethoxymagnesium, also organic bases, for example 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. Particularly preferred are alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate, calcium carbonate, cesium carbonate and rubidium carbonate.
Die Basen werden im allgemeinen in katalytischen Mengen eingesetzt, sie können aber auch äquimolar, im Überschuß oder gegebenenfalls als Lösungsmittel verwendet werden.  The bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
Die Edukte werden im allgemeinen in äquimolaren Mengen miteinander umgesetzt.  The starting materials are generally reacted with one another in equimolar amounts.
Alternativ können die Verbindungen der Formel I auch über eine umgekehrte Reaktionsfolge erhalten werden, d. h. aus der Umsetzung der Verbindungen der Formel II mit Verbind .
Figure imgf000007_0001
Alternatively, 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.
Figure imgf000007_0001
Diese Umsetzung erfolgt an sich unter den für die Umsetzung der Formel IV mit H-L1 genannten Bedingungen. This reaction takes place per se under the conditions mentioned for the reaction of formula IV with HL 1 .
Die Verbindungen der Formel VI können anschließend mit Verbindungen III zu den Derivaten der Formel V umgesetzt werden.  The compounds of the formula VI can then be reacted with compounds III to give the derivatives of the formula V.
Figure imgf000007_0002
Figure imgf000007_0002
Diese Umsetzung erfolgt an sich unter den für die Umsetzung der Formel II mit I II genannten Bedingungen.  This reaction takes place per se under the conditions mentioned for the reaction of the formula II with I II.
Die Reaktionsgemische werden in üblicher Weise aufgearbeitet, z.B. durch Mischen mit Wasser, Trennung der Phasen und gegebenenfalls chromatographische Reinigung der Rohprodukte. Die Zwischen- und Endprodukte fallen z.T. in Form farbloser oder schwach bräunlicher, zäher Öle an, die unter vermindertem Druck und bei mäßig erhöhter Temperatur von flüchtigen Anteilen befreit oder gereinigt werden. Sofern die Zwischen- und Endprodukte als Feststoffe erhalten werden, kann die Reinigung auch durch Umkristallisieren oder Digerieren erfolgen. Sofern einzelne Verbindungen I nicht auf den voranstehend beschriebenen Wegen zugänglich sind, können sie durch Derivatisierung anderer Verbindungen I hergestellt werden. The 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.
Sofern bei der Synthese Isomerengemische anfallen, ist im allgemeinen jedoch eine Trennung nicht unbedingt erforderlich, da sich die einzelnen Isomere teilweise während der Aufbereitung für die Anwendung oder bei der Anwendung (z.B. unter Licht-, Säureoder Baseneinwirkung) ineinander umwandeln können. Entsprechende Umwandlungen können auch nach der Anwendung, beispielsweise bei der Behandlung von Pflanzen in der behandelten Pflanze oder in der zu bekämpfenden Schadpflanze erfolgen.  However, unless 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.
Die für die Substituenten der erfindungsgemäßen Verbindungen genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenwasserstoffketten, wie Alkyl, Halo(gen)alkyl, Alkenyl, Alkinyl, sowie die Alkylteile und Alkenylteile in Alkoxy, Halo(gen)alkoxy, Alkyl- amino, Dialkylamino, N-Alkylsulfonylamino, Alkenyloxy, Alkinyloxy, Alkoxyamino, Alkyl- aminosulfonylamino, Dialkylaminosulfonylamino, Alkenylamino, Alkinylamino, N-(Alke- nyl)-N-(alkyl)-amino, N-(Alkinyl)-N-(alkyl)-amino, N-(Alkoxy)-N-(alkyl)-amino, N-(Alke- nyl)-N-(alkoxy)-amino oder N-(Alkinyl)-N-(alkoxy)-amino können geradkettig oder verzweigt sein. 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. 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- (alkoxy) -amino or N- (alkynyl) -N- (alkoxy) -amino straight-chain or branched.
Das Präfix Cn-Cm- gibt die jeweilige Kohlenstoffzahl der Kohlenwasserstoffeinheit an. Sofern nicht anders angegeben tragen halogenierte Substituenten vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome, insbesondere Fluoratome oder Chloratome. The prefix C n -C m - indicates the particular carbon number of the hydrocarbon moiety. Unless otherwise stated, halogenated substituents preferably carry one to five identical or different halogen atoms, in particular fluorine atoms or chlorine atoms.
Die Bedeutung Halogen steht jeweils für Fluor, Chlor, Brom oder lod.  The meaning halogen in each case represents fluorine, chlorine, bromine or iodine.
Ferner bedeuten beispielsweise:  Furthermore, for example:
Alkyl sowie die Alkylteile beispielsweise in Alkoxy, Alkylamino, Dialkylamino, N-Alkylsulfonylamino, Alkylaminosulfonylamino, Dialkylaminosulfonylamino, N-(Alkenyl)-N- (alkyl)-amino, N-(Alkinyl)-N-(alkyl)-amino, N-(Alkoxy)-N-(alkyl)-amino: gesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit einem oder mehr C-Atomen, z.B. 1 bis 2, 1 bis 4, oder 1 bis 6 Kohlenstoffatomen, z.B. Ci-C6-Alkyl wie Methyl, Ethyl, Propyl, 1 -Methylethyl, Butyl, 1 -Methylpropyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2,2-Dimethylpropyl, 1 -Ethylpropyl, Hexyl, 1 ,1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpen- tyl, 4-Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Dimethylbutyl, 2,2-Di- methylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2-Tri- methylpropyl, 1 ,2,2-Trimethylpropyl, 1 -Ethyl-1 -methylpropyl, 1 -Ethyl-2-methylpropyl. In einer erfindungsgemäßen Ausführungsform steht Alkyl für kleine Alkylgruppen wie Ci- C4-Alkyl. In einer anderen erfindungsgemäßen Ausführungsform steht Alkyl für größere Alkylgruppen wie Cs-Ce-Alkyl. 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-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl , 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2 , 2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1 -methylpropyl, 1-ethyl-2-methylpropyl. In one embodiment of the invention, alkyl is a small alkyl group such as C 1 -C 4 -alkyl. In another embodiment of the invention, alkyl is greater alkyl groups such as Cs-Ce-alkyl.
Halogenalkyl (auch als Haloalkyl bezeichnet): einen Alkylrest wie vorstehend genannt, dessen Wasserstoffatome partiell oder vollständig durch Halogenatome wie Fluor, Chlor, Brom und/oder lod substituiert sind, z.B. Chlormethyl, Dichlormethyl, Tri- chlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluor- methyl, Chlordifluormethyl, 2-Fluorethyl, 2-Chlorethyl, 2-Bromethyl, 2-lodethyl, 2,2-Di- fluorethyl, 2,2,2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2,2-difluorethyl, 2,2-Dichlor- 2-fluorethyl, 2,2,2-Trichlorethyl, Pentafluorethyl, 2-Fluorpropyl, 3-Fluorpropyl, 2,2-Di- fluorpropyl, 2,3-Difluorpropyl, 2-Chlorpropyl, 3-Chlorpropyl, 2,3-Dichlorpropyl, 2-Brom- propyl, 3-Brompropyl, 3,3,3-Trifluorpropyl, 3,3,3-Trichlorpropyl, 2,2,3,3,3-Pentafluor- propyl, Heptafluorpropyl, 1 -(Fluormethyl)-2-fluorethyl, 1 -(Chlormethyl)-2-chlorethyl, 1 - (Brommethyl)-2-bromethyl, 4-Fluorbutyl, 4-Chlorbutyl, 4-Brombutyl und Nonafluorbutyl. Cycloalkyl sowie die Cycloalkylteile beispielsweise in Cycloalkoxy oder Cycloalkyl- carbonyl: monocyclische, gesättigte Kohlenwasserstoffgruppen mit drei oder mehr C- Atomen, z.B. 3 bis 6 Kohlenstoffringgliedern, wie Cyclopropyl, Cyclobutyl, Cyclopentyl und Cyclohexyl. 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, pentafluoroethyl, 2-fluoropropyl, 3-fluoro-propyl, 2,2-di- fluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2, 2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluorobutyl, 4- Chlorobutyl, 4-bromobutyl and nonafluorobutyl. 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 sowie Alkenylteile beispielsweise in Alkenylamino, Alkenyloxy, N-(Alkenyl)- N-(alkyl)-amino, N-(Alkenyl)-N-(alkoxy)-amino: einfach ungesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit zwei oder mehr C-Atomen, z. B. 2 bis 4, 2 bis 6 oder 3 bis 6 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, z.B. C2-C6-Alkenyl wie 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, 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 -but- enyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2-butenyl,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 -Di- methyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2-propenyl, 1 -Ethyl-1 -prop- enyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3-Methyl-1 -pentenyl, 4-Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl,3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl 1 -propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5- Hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl,
1 - Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 ,1 -Dimethyl-2-butenyl, 1 ,1 -Dimethyl-3-butenyl, 1 ,2-Dimethyl-1 -butenyl, 1 ,2-Dimethyl-1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3 butenyl, 1, 2-dimethyl-1-butenyl, 1, 2-dimethyl
2- butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 -butenyl, 1 ,3-Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-1 -butenyl, 2,3-Dimethyl- 2-butenyl, 2,3-Dimethyl-3-butenyl, 3, 3-Dimethyl-1 -butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3-butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-but- enyl, 2-Ethyl-3-butenyl, 1 ,1 ,2-Trimethyl-2-propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl, 1 -Ethyl-2-methyl-2-propenyl. 2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3-dimethyl-1-butenyl, 1, 3-dimethyl-2-butenyl, 1, 3-dimethyl-3-butenyl, 2,2-dimethyl 3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl 2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl- 3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl-2- propenyl.
Cycloalkenyl: monocyclische, einfach ungesättigte Kohlenwasserstoffgruppen mit 3 bis 6, vorzugsweise 5 bis 6 Kohlenstoffringgliedern, wie Cyclopenten-1 -yl, Cyclopen- ten-3-yl, Cyclohexen-1 -yl, Cyclohexen-3-yl, Cyclohexen-4-yl.  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 ,
Alkinyl sowie Alkinylteile beispielsweise in Alkinyloxy, Alkinylamino, N-(Alkinyl)-N-(al- kyl)-amino oder N-(Alkinyl)-N-(alkoxy)-amino: geradkettige oder verzweigte Kohlen- wasserstoffgruppen mit zwei oder mehr C-Atomen, z. B. 2 bis 4, 2 bis 6, oder 3 bis 6 Kohlenstoffatomen und einer Dreifachbindung in beliebiger Position, z. B. C2-C6-Alkinyl wie Ethinyl, 1 -Propinyl, 2-Propinyl, 1 -Butinyl, 2-Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1 - Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1 -Methyl-2-butinyl, 1 -Methyl-3-butinyl,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-butinyl, 3-Methyl-1 -butinyl, 1 ,1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,
1 - Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, 1 -Methyl-3- pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-1 -pen- tinyl, 3-Methyl-4-pentinyl, 4-Methyl-1 -pentinyl, 4-Methyl-2-pentinyl, 1 ,1 -Dimethyl-2-but- inyl, 1 ,1 -Dimethyl-3-butinyl, 1 ,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3-Dime- thyl-1 -butinyl, 1 -Ethyl-2-butinyl, 1 -Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1 -Ethyl-1 -methyl-2- propinyl. 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 pentinyl, 2-methyl-4-pentynyl, 3-methyl-1-pentinyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-dimethyl 2-butynyl, 1, 1-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1 - Ethyl 2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl.
Alkoxy: Alkyl, wie vorstehend definiert, das über ein O-Atom gebunden ist: z. B. Me- thoxy, Ethoxy, n-Propoxy, 1 -Methylethoxy, Butoxy, 1 -Methylpropoxy, 2-Methylpropoxy oder 1 ,1 -Dimethylethoxy, Pentoxy, 1 -Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1 ,1 -Dimethylpropoxy, 1 ,2-Dimethylpropoxy, 2,2-Dimethylpropoxy, 1 -Ethylpropoxy, Hex- oxy, 1 -Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1 ,1 -Di- methylbutoxy, 1 ,2-Dimethylbutoxy, 1 ,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Di- methylbutoxy, 3,3-Dimethylbutoxy, 1 -Ethylbutoxy, 2-Ethylbutoxy, 1 ,1 ,2-Trimethylprop- oxy, 1 ,2,2-Trimethylpropoxy, 1 -Ethyl-1 -methylpropoxy oder 1 -Ethyl-2-methylpropoxy.  Alkoxy: alkyl, as defined above, which is bonded via an oxygen atom: z. Methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1 - Dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2 Dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2, 2-trimethylpropoxy, 1-ethyl-1-methylpropoxy or 1-ethyl-2-methylpropoxy.
3- bis 7-gliedriger monocyclischer oder 9- oder 10-gliedriger bicyclischer gesättigter, ungesättigter oder aromatischer Heterocyclus, enthaltend 1 , 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S kann über über C oder N gebunden sein. Bevorzugt sind davon 5- oder 6-gliedrige Heterocyclen.  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. Of these, preferred are 5- or 6-membered heterocycles.
Über N gebundene gesättigte oder ungesättigte heterocyclische Gruppen, wie: Pyri- dazin-3-yl, Pyridazin-4-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5-yl, Pyrazin-2-yl, 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-2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazole
3- yl, lsoxazol-4-yl, lsoxazol-5-yl, lsothiazol-3-yl, lsothiazol-4-yl, lsothiazol-5-yl, Imida- zol-1 -yl, lmidazol-2-yl, lmidazol-4-yl, Oxazol-2-yl, Oxazol-4-yl, Oxazol-5-yl, Thiazol-2-yl,3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazole 4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl,
Thiazol-4-yl und Thiazol-5-yl. Thiazol-4-yl and thiazol-5-yl.
Über C-gebundene heteroaromatische Gruppen, wie: Pyrazol-3-yl, lmidazol-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, Pyrazin-2-yl, [1 H]- Tetrazol-5-yl und [2H]-Tetrazol-5-yl.  Via 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.
Die Verbindungen der Formel I können, je nach Substitutionsmuster, ein oder mehrere weitere Chiralitätszentren enthalten. Die erfindungsgemäßen Verbindungen können daher als reine Enantiomere oder Diastereomere oder als Enantiomeren- oder Diastereomerengemische vorliegen. Gegenstand der Erfindung sind sowohl die reinen Enantiomeren oder Diastereomeren als auch deren Gemische. Depending on the substitution pattern, 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.
Die Verbindungen der Formel I können auch in Form der N-Oxide und/oder ihrer landwirtschaftlich brauchbaren Salze vorliegen, wobei es auf die Art des Salzes in der Regel nicht ankommt. Im Allgemeinen kommen die Salze derjenigen Kationen oder die Säureadditionssalze derjenigen Säuren in Betracht, deren Kationen, beziehungsweise Anionen, die herbizide Wirkung der Verbindungen I nicht negativ beeinträchtigen. Es kommen als Kationen insbesondere Ionen der Alkalimetalle, vorzugsweise Lithium, Natrium oder Kalium, der Erdalkalimetalle, vorzugsweise Calcium oder Magnesium, und der Übergangsmetalle, vorzugsweise Mangan, Kupfer, Zink oder Eisen in Betracht. Ebenso kann als Kation Ammonium verwendet werden, wobei hier gewünsch- tenfalls ein bis vier Wasserstoffatome durch Ci-C4-Alkyl, Hydroxy-Ci-C4-alkyl, C1-C4- Alkoxy-Ci-C4-alkyl, Hydroxy-Ci-C4-alkoxy-Ci-C4-alkyl, Phenyl oder Benzyl ersetzt sein können, vorzugsweise Ammonium, Dimethylammonium, Diisopropylammonium, Tetramethylammonium, Tetrabutylammonium, 2-(2-Hydroxyeth-1 -oxy)eth-1 -ylammonium, Di(2-hydroxyeth-1 -yl)ammonium, Trimethylbenzylammonium. Als Ammoniumkation kommt auch das durch Alkylierung oder Arylierung quaternisierte Pyridin-Stickstoffatom der Formel I in Frage. Des Weiteren kommen Phosphoniumionen, Sulfoniumionen, vorzugsweise Tri(Ci-C4-alkyl)sulfonium oder Sulfoxoniumionen, vorzugsweise Tri(Ci- C4-alkyl)sulfoxonium, in Betracht. 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. In general, 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. It is likewise possible to use 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. Also suitable as the ammonium cation is the pyridine nitrogen atom of the formula I quaternized by alkylation or arylation. Further suitable are phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 -alkyl) sulfonium or sulfoxonium ions, preferably tri (C 1 -C 4 -alkyl) sulfoxonium.
Anionen von brauchbaren Säureadditionsalzen sind in erster Linie Chlorid, Bromid, Fluorid, Hydrogensulfat, Sulfat, Dihydrogenphosphat, Hydrogenphosphat, Nitrat, Hydrogencarbonat, Carbonat, Hexafluorosilikat, Hexafluorophosphat, Benzoat sowie die Anionen von Ci-C4-Alkansäuren, vorzugsweise Formiat, Acetat, Propionat, Butyrat oder Trifluoracetat.  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.
Die besonders bevorzugten Ausführungsformen der Zwischenprodukte in Bezug auf die Variablen entsprechen denen der Gruppen der Formel I. The particularly preferred embodiments of the intermediates with respect to the variables correspond to those of the groups of the formula I.
In einer besonderen Ausführungsform haben die Variablen der Verbindungen der Formel I folgende Bedeutungen, wobei diese sowohl für sich allein betrachtet als auch in Kombination miteinander besondere Ausgestaltungen der Verbindungen der Formel I darstellen:  In a particular embodiment, the 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:
In einer bevorzugten Ausführungsform der Verbindungen der Formel I stehen A und G für N und E steht für C-Rc. Diese Verbindungen entsprechen der Formel 1.1 , In a preferred embodiment 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,
Figure imgf000011_0001
Figure imgf000011_0001
worin die Gruppen Rc1 und Rc2 jeweils einer Gruppe Rc entsprechen und bevorzugt folgende Bedeutungen haben: wherein the groups R c1 and R c2 each correspond to a group R c and preferably have the following meanings:
Rc1 H, Alkyl, Haloalkyl, insbesondere Alkyl; R c1 is H, alkyl, haloalkyl, in particular alkyl;
Rc2 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H, Br, OH und R c2 H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and
In einer bevorzugten Ausführungsform der Verbindungen der Formel I stehen A und E für N und G steht für C-Rc. Diese Verbindungen entsprechen der Formel I.2,
Figure imgf000012_0001
In a preferred embodiment of the compounds of the formula I, A and E are N and G is CR c . These compounds correspond to the formula I.2,
Figure imgf000012_0001
worin die Gruppen Rc1 jeweils einer Gruppe Rc entsprechen und bevorzugt folgende Bedeutungen haben: wherein the groups R c1 each correspond to a group R c and preferably have the following meanings:
Rc1 H, Alkyl, Haloalkyl, insbesondere Alkyl; R c1 is H, alkyl, haloalkyl, in particular alkyl;
Rc2 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H, Br, OH und R c2 H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and
OCH3. OCH 3 .
In besonders bevorzugten Ausführungsformen der Verbindungen der Formel I und insbesondere solcher der Formel 1.1 und I.2 ist R1 ausgewählt aus OH, OCH3, In particularly preferred embodiments of the compounds of the formula I and especially those of the formula I.1 and I.2, R 1 is selected from OH, OCH 3,
OC(0)CH3, OC(0)CH2CH3, OC(0)CH(CH3)2, OC(0)C(CH3)3, OC(0)-c-C3H5, OC(O)- C6H5, OC(0)-CH2C6H5, OC(0)CH2CI, OC(0)-CF3, OC(0)-CH2OCH3, OC(0)-N(CH3)2 und OC(0)-OCH2CH3. OC (0) CH 3, OC (0) CH 2 CH 3, OC (0) CH (CH 3) 2, OC (0) C (CH 3) 3, OC (0) -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 (0) -N (CH 3 ) 2 and OC (O) -OCH 2 CH 3 .
In besonders bevorzugten Ausführungsformen der Verbindungen der Formel I und insbesondere solcher der Formel 1.1 und I.2 bedeutet R2 Phenyl, welches substituiert ist durch eine Gruppe ausgewählt aus 2-Br, 2-CI, 2,4-CI2, 2-CI-4-F, 2-CI-5-F, 2-CI-6-F, 2-CI-4-CF3, 2-CI-5-CF3, 2-CI-6-CF3, 2-CI-3,6-F2, 2-F, 2,4-F2, 2,5-F2, 2,6-F2, 2-F-4-CF3, 2-F-5-CF3, 2-F-6-CF3, 2,3,6-F3, 2-N02, 2-N02-4-F, 2-N02-5-F, 2-N02-6-F, 2-N02-4-CF3, 2-N02-5-CF3, 2-N02-6-CF3, 2-N02-3,6-F2, 2-CN, 2-CH3, 2-CH3-4-F, 2-CH3-5-F, 2-CH3- 6-F, 2-CH3-4-CF3, 2-CH3-5-CF3, 2-CH3-6-CF3, 2-CH3-3,6-F2, 2-OCH3, 2-OCH3-4-F, 2-OCH3-5-F, 2-OCH3-6-F, 2-OCH3-4-CF3, 2-OCH3-5-CF3, 2-OCH3-6-CF3, 2-OCH3-3,6- F2, 2-CHF2, 2-CHF2-4-F, 2-CHF2-5-F, 2-CHF2-6-F, 2-CHF2-4-CF3, 2-CHF2-5-CF3,In particularly preferred embodiments of the compounds of the formula I and especially those of the formula I.1 and I.2, 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 -4-F, 2-CH 3 -5-F, 2-CH 3 -6-F, 2-CH 3 -4-CF 3 , 2-CH 3 -5-CF 3 , 2-CH 3 -6-CF 3 , 2-CH 3 -3,6-F 2 , 2-OCH 3 , 2-OCH 3 -4-F, 2-OCH 3 -5-F, 2-OCH 3 - 6-F, 2-OCH 3 -4-CF 3 , 2-OCH 3 -5-CF 3 , 2-OCH 3 -6-CF 3 , 2-OCH 3 -3,6-F 2 , 2-CHF 2 , 2-CHF 2 -4-F, 2-CHF 2 -5-F, 2-CHF 2 -6-F, 2-CHF 2 -4-CF 3 , 2-CHF 2 -5-CF 3 ,
2-CHF2-6-CF3, 2-CHF2-3,6-F2, 2-CF3, 2-CF3-4-F, 2-CF3-5-F, 2-CF3-6-F, 2-CF3-4-CF3, 2-CF3-5-CF3, 2-CF3-6-CF3, 2-CF3-3,6-F2, 2-OCHF2, 2-OCHF2-4-F, 2-OCHF2-5-F, 2-OCHF2-6-F, 2-OCHF2-4-CF3, 2-OCHF2-5-CF3, 2-OCHF2-6-CF3, 2-OCHF2-3,6-F2, 2-OCF3, 2-OCF3-4-F, 2-OCF3-5-F, 2-OCF3-6-F, 2-OCF3-4-CF3, 2-OCF3-5-CF3, 2-OCF3- 6-CF3 oder 2-OCF3-3,6-F2. 2-CHF 2 -6-CF 3 , 2-CHF 2 -3,6-F 2 , 2-CF 3 , 2-CF 3 -4-F, 2-CF 3 -5-F, 2-CF 3 - 6-F, 2-CF 3 -4-CF 3 , 2-CF 3 -5-CF 3 , 2-CF 3 -6-CF 3 , 2-CF 3 -3,6-F 2 , 2-OCHF 2 , 2-OCHF 2 -4-F, 2-OCHF 2 -5-F, 2-OCHF 2 -6-F, 2-OCHF 2 -4-CF 3 , 2-OCHF 2 -5-CF 3 , 2 OCHF 2 -6-CF 3 , 2-OCHF 2 -3,6-F 2 , 2-OCF 3 , 2-OCF 3 -4-F, 2-OCF 3 -5-F, 2-OCF 3 -6- F, 2-OCF 3 -4-CF 3 , 2-OCF 3 -5-CF 3 , 2-OCF 3 - 6-CF 3 or 2-OCF 3 -3,6-F 2 .
In besonders bevorzugten Ausführungsformen der Verbindungen der Formel I und insbesondere solcher der Formel 1.1 und I.2 ist X ausgewählt aus Sauerstoff und Schwefel.  In particularly preferred embodiments of the compounds of the formula I and especially those of the formula I.1 and I.2, X is selected from oxygen and sulfur.
In besonders bevorzugten Ausführungsformen der Verbindungen der Formel I und insbesondere solcher der Formel 1.1 und I.2 ist Y ausgewählt aus Sauerstoff und Schwefel.  In particularly preferred embodiments of the compounds of the formula I and especially those of the formula I.1 and I.2, Y is selected from oxygen and sulfur.
In einer weiteren Ausführungsform der Verbindungen der Formel I steht A, E und G für N. Diese Verbindungen en In a further embodiment of the compounds of the formula I, A, E and G are N. These compounds
Figure imgf000012_0002
worin die Gruppe Rc2 einer Gruppe Rc entspricht und bevorzugt für H, Alkyl, Haloal- kyl, insbesondere Alkyl steht.
Figure imgf000012_0002
wherein the group R c2 corresponds to a group R c and preferably represents H, alkyl, haloalkyl, in particular alkyl.
In einer weiteren Ausführungsform der Verbindungen der Formel I steht A für S und E und G für C-Rc. Diese Verbindungen entsprechen der Formel I.4. In a further embodiment of the compounds of the formula I, A is S and E and G is CR c . These compounds correspond to the formula I.4.
Figure imgf000013_0001
Figure imgf000013_0001
worin die Gruppen Rc1 und Rc2 je einer Gruppe Rc entsprechen und bevorzugt für H, Alkyl, Haloalkyl, insbesondere H (Rc1) und Alkyl (Rc2) stehen. wherein the groups 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 ).
In einer weiteren Ausführungsform der Verbindungen der Formel I steht A für C-Rc, E für N und G für N-Rc. Diese V sprechen der Formel I.5. In a further embodiment of the compounds of the formula I, A is CR c , E is N and G is NR c . These V speak the formula I.5.
Figure imgf000013_0002
Figure imgf000013_0002
worin die Gruppen Rc1 und Rc2 je einer Gruppe Rc entsprechen und bevorzugt für H, Alkyl, ggf. subst. Phenyl, insbesondere H (Rc1) und Alkyl und ggf. subst. Phenyl (Rc2) stehen. wherein the groups 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.
In einer weiteren Ausführungsform der Verbindungen der Formel I steht A und G für C-Rc und E für S. Diese Verbindungen entsprechen der Formel I.6. In a further embodiment of the compounds of the formula I, A and G are CR c and E is S. These compounds correspond to the formula I.6.
Figure imgf000013_0003
Figure imgf000013_0003
worin die Gruppen Rc1 und Rc2 je einer Gruppe Rc entsprechen und bevorzugt für H und Alkyl, insbesondere H stehen. wherein the groups R c1 and R c2 each correspond to a group R c and are preferably H and alkyl, in particular H.
In einer ersten bevorzugten Ausführungsform der Erfindung steht R1 für 0-RA. In a first preferred embodiment of the invention, R 1 is O -R A.
In einer weiteren bevorzugten Ausführungsform der Erfindung steht R1 für S(0)n-RA, darin steht n bevorzugt für 0 oder 2, insbesondere für 2. In a further preferred embodiment of the invention, R 1 is S ( O ) n -R A , where n is preferably 0 or 2, in particular 2.
In einer weiteren bevorzugten Ausführungsform steht R1 für 0-S(0)n-RA, darin steht n bevorzugt für 0 oder 2, insbesondere für 2, wie beispielsweise OS(0)2-CH3, OS(0)2- C2H5, OS(0)2-C3H7, OS(0)2-C6H5 oder OS(0)2-(4-CH3-C6H4). In a further preferred embodiment, 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 ).
In einer weiteren bevorzugten Ausführungsform steht R1 für 0-S(0)n-NR'Rii, insbesondere mit den nachfolgend bevorzugt genannten Gruppen NR'R". In einer weiteren bevorzugten Ausführungsform steht R1 für NR'R", worin R'R" insbesondere die nachstehenden bevorzugten Bedeutungen hat oder besonders bevorzugt für Diethyl steht. RA steht insbesondere für H, d-Ce-Alkylcarbonyl, wie C(0)CH3, C(0)CH2CH3,In a further preferred embodiment, R 1 is O-S (O) n -NR'R ii , in particular with the groups NR'R "which are preferably mentioned below. In a further preferred embodiment, 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 ,
C(0)CH(CH3)2 oder C(0)C(CH3)3; d-Ce-Cycloalkylcarbonyl, wie Cyclopropylcarbonyl, Cyclopentylcarbonyl oder Cyclohexylcarbonyl; C2-C6-Alkenylcarbonyl, wie C (O) CH (CH 3 ) 2 or C (O) C (CH 3 ) 3 ; d-Ce-cycloalkylcarbonyl such as cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl; C2-C6 alkenylcarbonyl, as
C(0)CH=CH2 oder C(0)CH2CH=CH2, ggf. subst. Benzoyl, wie C(0)C6H5, C (0) CH = CH 2 or C (O) CH 2 CH = CH 2 , optionally subst. Benzoyl, such as C (O) C 6 H 5 ,
C(0)[2-CH3-C6H4], C(0)[4-CH3-C6H4], C(0)[2-F-C6H4], C(0)[4-F-C6H4], oder ggf. subst. Heteroaryl, wie Pyridin, welches über eine Carbonylgruppe gebunden ist. Besonders bevorzugt steht RA für H oder Ci-C6-Alkylcarbonyl. 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 subst. Heteroaryl, such as pyridine, which is bonded via a carbonyl group. R A is particularly preferably H or C 1 -C 6 -alkylcarbonyl.
Weiter besonders bevorzugt ist RA ausgewählt aus der Gruppe H, OCH3, C(0)CH3, C(0)CH2CH3, C(0)CH(CH3)2, C(0)C(CH3)3, C(0)-c-C3H5, C(0)-C6H5, C(0)-CH2C6H5, C(0)CH2CI, C(0)CF3, C(0)CH2OCH3, C(0)N(CH3)2 und C(0)OCH2CH3. More preferably, 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 .
In einer weiteren bevorzugten Ausführungsform der Erfindung steht RA für NR'R". In einer weiteren bevorzugten Ausführungsform der Erfindung steht RA für In a further preferred embodiment of the invention, R A is NR'R ". In a further preferred embodiment of the invention, R A is
Z-NR'-C(0)-NR'R'', wobei R' und R" wie eingangs und bevorzugt wie nachstehend definiert ist. In weiteren Ausführungsformen kommen für R' und R" unabhängig voneinander auch Ci-C4-Alkoxy, Ci-C4-Haloalkoxy und Ci-C4-Alkoxy-Ci-C4-alkyl in Frage, ins- besondere OCH3, OC2H5, CH2CH2OCH3und CH2CH2CI. Z-NR'-C (O) -NR'R ", where R 'and R" are as defined above and preferably as defined below In further embodiments, 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.
R' und R" stehen vorzugsweise für Ci-Cs-Alkyl, Ci-C4-Haloalkyl, Z-C3-C6-Cycloalkyl, Z-Ci-C8-Alkoxy, Z-Ci-C8-Haloalkoxy, Z-Phenyl, Z-C(=0)-Ra oder Z-Hetaryl. Bevorzugt sind dabei CH3, C2H5, n-Propyl, CH(CH3)2, Butyl, 2-Chorethyl, Cyclopentyl, Cyclohexyl, 2-Ethoxymethyl, 2-Chlorethoxy, Phenyl, Pyrimidine oder Triazine, welche Ringe un- substituiert oder substituiert sind. Bevorzugte Substituenten sind dabei Ci-C4-Alkyl- carbonyl oder Ci-C4-Haloalkylcarbonyl, insbesondere C(=0)-CH3, C(=0)-C2H5, C(=0)- C3H7, C(=0)-CH(CH3)2, Butylcarbonyl und C(=0)-CH2CI. Besonders bevorzugte Ausgestaltungen der Gruppe NR'R" sind N(Di-Ci-C4-alkyl), insbesondere N(CH3)-Ci-C4- alkyl, wie N(CH3)2, N(CH3)CH2CH3, N(CH3)C3H7 und N(CH3)CH(CH3)2. R 'and R "are preferably C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, ZC 3 -C 6 -cycloalkyl, Z-C 1 -C 8 -alkoxy, Z-C 1 -C 8 -haloalkoxy, Z-phenyl, Z is C (= O) -R a or Z-hetaryl, in which case CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , butyl, 2-chorethyl, cyclopentyl, cyclohexyl, 2-ethoxymethyl, 2 are preferred Chloroethoxy, phenyl, pyrimidines or triazines, which rings are unsubstituted or substituted. Preferred substituents are C 1 -C 4 -alkylcarbonyl or C 1 -C 4 -haloalkylcarbonyl, in particular C (= O) -CH 3 , C ( = 0) -C 2 H 5 , C (= O) -C 3 H 7 , C (= O) -CH (CH 3 ) 2 , butylcarbonyl and C (= O) -CH 2 Cl. Particularly preferred embodiments of the group NR'R "are 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 .
Weitere besonders bevorzugte Ausgestaltungen für NR'R" sind NH-Aryl, wobei Aryl bevorzugt für Phenyl steht, welches - insbesondere in der 2- und 6-Position - substituiert ist durch eine bis drei gleiche oder verschiedene Gruppen Halogen, CH3, Halogen- d-C2-alkyl, Halogen-Ci-C2-alkoxy und Carboxyl, wie 2-CI,6-COOH-C6H3, 2,6-CI2-C6H3, 2,6-F2-C6H3, 2,6-CI2 3-C6H2, 2-CF3,6-CH2CHF2-C6H3, 2-CF3,6-OCF3-C6H3 und 2-CF3,6- CH2CHF2-C6H3. Further particularly preferred embodiments of NR'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-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 .
Weitere Ausgestaltungen für NR'R" sind NH-Heteroaryl, wobei Heteroaryl bevorzugt für eine der nachstehenden bevorzugten heteroaromatischen Gruppen steht, insbesondere für Triazinyl, Pyrimidinyl oder Triazolopyrimidinyl, wie [1 ,2,4]triazolo[1 ,5-a]pyri- midin-2-yl, steht, welche Gruppen substituiert sein können, insbesondere durch C1-C4- Alkoxy und/oder Halogen. Besonders bevorzugt sind 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-Fluor-7-methoxy- [1 ,2,4]triazolo[1 ,5-a]pyrimidin-2-yl und 5-Fluor-7-ethoxy-[1 ,2,4]triazolo[1 ,5-a]pyrimidin- 2-yl. Further embodiments of 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.
In einer weiteren bevorzugten Ausführungsform der Erfindung steht RA für einen ggf. durch Rb substituierten 5- oder 6-gliedrigen Heterocyclus wie zuvor definiert, der vor- zugsweise entweder 1 , 2, 3 oder 4 Stickstoffatome oder 1 Sauerstoff oder 1 Schwefelatom und gegebenenfalls 1 oder 2 Stickstoffatome als Ringlieder aufweist und die un- substituiert ist oder 1 oder 2 aus Rb ausgewählte Substituenten aufweisen kann. Bevorzugt sind über N gebundene gesättigte oder ungesättigte Gruppen, wie z.B.: In a further preferred embodiment of the invention, 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 . Preference is given to saturated or unsaturated groups which are bonded via N, for example:
Heteroaromatische Gruppen: Pyridazin-3-yl, Pyridazin-4-yl, Pyrimidin-2-yl, Pyrimidin- 4-yl, Pyrimidin-5-yl, Pyrazin-2-yl, 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, Pyrazol-1 -yl, Pyrazol-3-yl, Pyrazol-4-yl, lsoxazol-3-yl, lsoxazol-4-yl, lsoxazol-5-yl, lsothiazol-3-yl, lsothiazol-4-yl, lsothiazol-5-yl, lmidazol-1 -yl, lmidazol-2-yl, lmidazol-4-yl, Oxazol-2-yl, Oxazol-4-yl, Oxazol-5-yl, Thiazol-2-yl, Thiazol-4-yl und Thiazol-5-yl.  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 thiazol-5-yl.
In einer anderen Ausgestaltung steht RA für eine über C-gebundene heteroaromati- sehe Gruppe wie Pyrazol-3-yl, lmidazol-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, Pyri- midin-5-yl, Pyridazin-4-yl, Pyrazin-2-yl, [1 H]-Tetrazol-5-yl und [2H]-Tetrazol-5-yl, wobei die hier exemplarisch genannten Heterocyclen 1 oder 2 aus Rb ausgewählte Substituenten aufweisen können. Bevorzugte Gruppen Rb sind insbesondere F, Cl, CN, NO2, CH3, C2H5, OCH3, OC2H5, OCHF2, OCF3 und CF3. In another embodiment, 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. In particular, 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 3 .
In einer weiteren bevorzugten Ausgestaltung steht R2 für Phenyl, welches unsubsti- tuiert ist oder teilweise oder vollständig durch Gruppen Rb substituiert ist. Besonders bevorzugt sind solche Verbindungen, in denen eine Gruppe Rb in ortho-Position steht. Solche Verbindungen der For I.A beschrieben:
Figure imgf000015_0001
In a further preferred embodiment, 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:
Figure imgf000015_0001
In Formel I.A steht der Index m für Null oder eine ganze Zahl von eins bis vier, bevorzugt für 0, 1 oder 2, insbesondere for 0 oder 1. R5 und R6 stehen für Gruppen Rb, wie eingangs definiert, bevorzugt für Halogen, NO2, Ci-C4-Alkyl, Ci-C2-Halogenalkyl und Ci-C4-Alkoxy. Eine Gruppe R6 steht bevorzugt in Position 5. Eine Gruppe R6 in der Position 3 stellt eine weitere bevorzugte Ausführungsform dar. In formula IA, the subscript m is zero or an integer from one to four, preferably 0, 1 or 2, in particular 0 or 1. 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.
Besonders bevorzugt steht R5 für Br, F, N02, CN, CH3, OCH3, OCF3, CF3, CHF2 oder OCHF2. R6 steht besonders bevorzugt für Halogen oder Halogenmethyl, wie Cl, F oder CF3. Insbesondere bevorzugt ist (R6)m ausgewählt aus 4-F, 5-F, 6-F, 4-CF3, 5-CF3 und 3,6-F2. 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 .
In einer bevorzugten Ausführungsform steht X für O. In a preferred embodiment, X is O.
In einer weiteren Ausführungsform steht X für S.  In another embodiment, X is S.
In einer weiteren Ausführungsform steht X für NR3. In einer bevorzugten Ausführungsform steht Y für O. In another embodiment, X is NR 3 . In a preferred embodiment, Y is O.
In einer weiteren Ausführungsform steht Y für NR3. In another embodiment, Y is NR 3 .
In einer weiteren Ausführungsform steht Y für S.  In another embodiment Y stands for S.
R3 steht bevorzugt für H, Ci-C6-Alkyl, wie CH3, C2H5, n-C3H7, CH(CH3)2, n-C3H9, oder C(CH3)3; d-Ce-Halogenalkyl, wie CH2CF3, CH2CHF2; C3-C6-Cycloalkyl-Ci-C4-alkyl, wie Cyclopropylmethyl, C3-C6-Alkenyl, wie CH2CH=CH2, CH2C(CH3)=CH2, R 3 is preferably H, C 1 -C 6 -alkyl, such as CH 3 , C 2 H 5 , nC 3 H 7 , CH (CH 3 ) 2 , nC 3 H 9 , or C (CH 3 ) 3 ; d-Ce-haloalkyl such as CH 2 CF 3 , CH 2 CHF 2 ; C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl, such as cyclopropylmethyl, C 3 -C 6 -alkenyl, such as CH 2 CH = CH 2 , CH 2 C (CH 3 ) = CH 2 ,
CH2CH2CH=CH2, CH2CH2C(CH3)=CH2, CH2CH2CH2CH=CH2, CH 2 CH 2 CH = CH 2 , CH 2 CH 2 C (CH 3 ) = CH 2 , CH 2 CH 2 CH 2 CH = CH 2 ,
CH2CH2CH2C(CH3)=CH2, oder ggf. subst. Phenyl, wie C6H5, 4-CH3-C6H4, 4-F-C6H4 oder S(0)n-RN, worin RN für Ci-C6-Halogenalkyl steht, wie CH2CF3, CH2CHF2. Besonders bevorzugt steht R3 für Halogenalkyl. Sofern sowohl X als auch Y für N-R3 stehen, sind die Gruppen R3 unabhängig voneinander ausgewählt. Eine weitere Ausführungsform betrifft die N-Oxide der Verbindungen der Formel I. Eine weitere Ausführungsform betrifft Salze der Verbindungen der Formel I, insbesondere solche erhältlich durch Quaternisierung des Pyridin-Stickstoffatoms, die bevorzugt erfolgen kann durch Alkylierung oder Arylierung der Verbindungen der Formel I. Entsprechend sind bevorzugte Salze der Verbindungen die N-Alkyl-, insbesondere die N-Methyl-, bzw. die N-Phenyl-Salze. 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.
Besonders bevorzugte Ausgestaltungen der Formel I umfassen die folgenden, in denen die Variablen die eingangs definierten und insbesondere die weiter oben genannten bevorzugten Bedeutungen haben: Particularly preferred embodiments of the formula I include the following, in which the variables have the meanings defined above and in particular the preferred meanings mentioned above:
Figure imgf000016_0001
Figure imgf000016_0001
Insbesondere sind im Hinblick auf ihre Verwendung die in den folgenden Tabellen zusammengestellten Verbindungen der Formel I, welche den Formeln 1.1 A* und I.2A* entsprechen, bevorzugt. Die in den Tabellen für einen Substituenten genannten Grup- pen stellen außerdem für sich betrachtet, unabhängig von der Kombination, in der sie genannt sind, eine besonders bevorzugte Ausgestaltung des betreffenden Substituenten dar. In particular, with regard to their use, the compounds of the formula I compiled in the following tables, which correspond to the formulas 1.1 A * and I.2A * , are preferred. Moreover, the groups mentioned in the tables for a substituent, independently of the combination in which they are mentioned, represent a particularly preferred embodiment of the substituent in question.
Tabelle 1  Table 1
Verbindungen der Formel 1.1 A*, in denen X und Y O bedeuten, der Index m in (R6)m Null bedeutet und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of formula 1.1 A * , in which X and YO, the index 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.
Tabelle 2  Table 2
Verbindungen der Formel 1.1 A*, in denen X und Y O bedeuten, (R6)m für 4-CI steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X and Y are O, (R 6 ) m is 4-Cl and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
Tabelle 3  Table 3
Verbindungen der Formel 1.1 A*, in denen X und Y O bedeuten, (R6)m für 3-F steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X and Y are O, (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.
Tabelle 4  Table 4
Verbindungen der Formel 1.1 A*, in denen X und Y O bedeuten, (R6)m für 4-F steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X and Y are O, (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.
Tabelle 5  Table 5
Verbindungen der Formel 1.1 A*, in denen X und Y O bedeuten, (R6)m für 5-F steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * in which X and Y are O, (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.
Tabelle 6  Table 6
Verbindungen der Formel 1.1 A*, in denen X und Y O bedeuten, (R6)m für 6-F steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X and Y are O, (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.
Tabelle 7  Table 7
Verbindungen der Formel 1.1 A*, in denen X und Y O bedeuten, (R6)m für 4-CF3 steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X and Y are O, (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.
Tabelle 8  Table 8
Verbindungen der Formel 1.1 A*, in denen X und Y O bedeuten, (R6)m für 5-CF3 steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X and Y are O, (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.
Tabelle 9  Table 9
Verbindungen der Formel 1.1 A*, in denen X und Y O bedeuten, (R6)m für 3,6-F2 steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X and Y are O, (R 6 ) m is 3,6-F 2 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
Tabelle 10  Table 10
Verbindungen der Formel 1.1 A*, in denen X O und Y NH bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Tabelle 1 1 Compounds of the formula 1.1 A * in which X is O and Y is NH and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A Table 1 1
Verbindungen der Formel 1.1 A*, in denen X O und Y N-CH3 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X is O and Y is N-CH3 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 12  Table 12
Verbindungen der Formel 1.1 A*, in denen X O und Y N-C2H5 bedeuten und die Kombi- nation von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Tabelle 13 Compounds of the formula 1.1 A * in which X is O and Y is N-C2H5 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A. Table 13
Verbindungen der Formel 1.1 A*, in denen X O und Y N-n-C3H7 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1A * in which XO and Y denote NnC 3 H 7 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 14  Table 14
Verbindungen der Formel 1.1 A*, in denen X O und Y N-CH(CH3)2 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * in which X is O and Y is N-CH (CH 3 ) 2 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 15  Table 15
Verbindungen der Formel 1.1 A*, in denen X O und Y N-n-C4H9 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * in which X is O and Y is NnC 4 H 9 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 16  Table 16
Verbindungen der Formel 1.1 A*, in denen X O und Y N-CH2CH=CH2 bedeuten und die Kombination von R1 , R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * in which X is O and Y is N-CH 2 CH = CH 2 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 17  Table 17
Verbindungen der Formel 1.1 A*, in denen X O und Y N-CH2C CH bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X is O and Y is N-CH 2 C-CH and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 18  Table 18
Verbindungen der Formel 1.1 A*, in denen X O und Y N-CH2CN bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * in which X is O and Y is N-CH 2 CN and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 19  Table 19
Verbindungen der Formel 1.1 A*, in denen X O und Y N-CH2CF3 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula 1.1 A * , in which X is O and Y is N-CH 2 CF 3 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 20  Table 20
Verbindungen der Formel 1.1 A*, in denen X O und Y N-CH2C6H5 bedeuten und dieCompounds of formula 1.1 A * , in which XO and Y are N-CH 2 C 6 H 5 and the
Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Combination of R 1 , R 5 and (R 6 ) n for a compound corresponds in each case to one row of Table A.
Tabelle 21  Table 21
Verbindungen der Formel I.2A*, in denen X und Y O bedeuten, der Index m in (R6)m Null bedeutet und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X and Y are O, the index 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.
Tabelle 22  Table 22
Verbindungen der Formel I.2A*, in denen X und Y O bedeuten, (R6)m für 4-CI steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X and Y are O, (R 6 ) m is 4-Cl and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
Tabelle 23  Table 23
Verbindungen der Formel I.2A*, in denen X und Y O bedeuten, (R6)m für 3-F steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X and Y are O, (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.
Tabelle 24  Table 24
Verbindungen der Formel I.2A*, in denen X und Y O bedeuten, (R6)m für 4-F steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X and Y are O, (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.
Tabelle 25  Table 25
Verbindungen der Formel I.2A*, in denen X und Y O bedeuten, (R6)m für 5-F steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X and YO are (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.
Tabelle 26  Table 26
Verbindungen der Formel I.2A*, in denen X und Y O bedeuten, (R6)m für 6-F steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X and Y are O, (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.
Tabelle 27  Table 27
Verbindungen der Formel I.2A*, in denen X und Y O bedeuten, (R6)m für 4-CF3 steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X and Y are O, (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.
Tabelle 28  Table 28
Verbindungen der Formel I.2A*, in denen X und Y O bedeuten, (R6)m für 5-CF3 steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X and YO are (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.
Tabelle 29  Table 29
Verbindungen der Formel I.2A*, in denen X und Y O bedeuten, (R6)m für 3,6-F2 steht und die Kombination von R1 und R5 für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X and Y are O, (R 6 ) m is 3,6-F 2 and the combination of R 1 and R 5 for a compound corresponds in each case to one row of Table A.
Tabelle 30  Table 30
Verbindungen der Formel I.2A*, in denen X O und Y NH bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Tabelle 31 Compounds of the formula I.2A * in which X is O and Y is NH and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A Table 31
Verbindungen der Formel I.2A*, in denen X O und Y N-CH3 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X is O and Y is N-CH3 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 32  Table 32
Verbindungen der Formel I.2A*, in denen X O und Y N-C2H5 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X is O and Y is N-C2H5 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 33  Table 33
Verbindungen der Formel I.2A*, in denen X O und Y N-n-C3H7 bedeuten und die Kom- bination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Tabelle 34 Compounds of the formula I.2A * in which X is O and Y is Nn-C3H 7 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A. Table 34
Verbindungen der Formel I.2A*, in denen X O und Y N-CH(CH3)2 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X is O and Y is N-CH (CH 3) 2 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 35  Table 35
Verbindungen der Formel I.2A*, in denen X O und Y N-n-C4Hg bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X is O and Y is Nn-C4Hg and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 36  Table 36
Verbindungen der Formel I.2A*, in denen X O und Y N-CH2CH=CH2 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X is O and Y is N-CH 2 CH = CH 2 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 37  Table 37
Verbindungen der Formel I.2A*, in denen X O und Y Ν-ΟΗ^ΟΞΟΗ bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X is O and Y is Ν-ΟΗ ^ ΟΞΟΗ and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 38  Table 38
Verbindungen der Formel I.2A*, in denen X O und Y N-CH2CN bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A ent- spricht Compounds of the formula I.2A * in which X is O and Y is N-CH 2 CN and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 39  Table 39
Verbindungen der Formel I.2A*, in denen X O und Y N-CH2CF3 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X is O and Y is N-CH 2 CF 3 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle 40  Table 40
Verbindungen der Formel I.2A*, in denen X O und Y N-CH2C6H5 bedeuten und die Kombination von R1, R5 und (R6)n für eine Verbindung jeweils einer Zeile der Tabelle A entspricht Compounds of the formula I.2A * in which X is O and Y is N-CH 2 C 6 H 5 and the combination of R 1 , R 5 and (R 6 ) n for each compound corresponds to one row of Table A.
Tabelle A: Verbindungen der Formel I Table A: Compounds of the formula I
Nr. R R5 Nr. R R5 No RR 5 No RR 5
A-1 OH Br A-12 OC(0)-CH2OCH3 BrA-1 OH Br A-12 OC (0) -CH 2 OCH 3 Br
A-2 OCH3 Br A-13 OC(0)-N(CH3)2 BrA-2 OCH3 Br A-13 OC (0) -N (CH 3) 2 Br
A-3 OC(0)CH3 Br A-14 OC(0)-OCH2CH3 BrA-3 OC (0) CH 3 Br A-14 OC (O) -OCH 2 CH 3 Br
A-4 OC(0)CH2CH3 Br A-15 OS(0)2-CH3 BrA-4 OC (0) CH 2 CH 3 Br A-15 OS (0) 2 -CH 3 Br
A-5 OC(0)CH(CH3)2 Br A-16 OS(0)2-C2H5 BrA-5 OC (0) CH (CH 3 ) 2 Br A-16 OS (0) 2 -C 2 H 5 Br
A-6 OC(0)C(CH3)3 Br A-17 OS(0)2-C3H7 BrA-6 OC (0) C (CH 3 ) 3 Br A-17 OS (0) 2 -C 3 H 7 Br
A-7 OC(0)-c-C3H5 Br A-18 OS(0)2-CH(CH3)2 BrA-7 OC (0) -c C 3 H 5 Br A-18 OS (0) 2 -CH (CH 3 ) 2 Br
A-8 OC(0)-C6H5 Br A-19 OS(0)2-C6H5 BrA-8 OC (0) -C 6 H 5 Br A-19 OS (0) 2 -C 6 H 5 Br
A-9 OC(0)-CH2C6H5 Br A-20 OS(0)2-T1 BrA-9 OC (0) -CH 2 C 6 H 5 Br A-20 OS (0) 2 -T1 Br
A-10 OC(0)CH2CI Br A-21 OS(0)2-T2 BrA-10 OC (0) CH 2 Cl Br A-21 OS (0) 2 -T2 Br
A-1 1 OC(0)-CF3 Br A-22 OS(0)2-T3 Br Nr. R R5 Nr. R R5 A-1 1 OC (0) CF 3 Br A-22 OS (0) 2 -T3 Br No RR 5 No RR 5
A-23 OS(0)2-T4 Br A-62 0S(0)2-T1 1 ClA-23 OS (0) 2 -T4 Br A-62 0S (0) 2 -T1 1 Cl
A-24 OS(0)2-T5 Br A-63 OS(0)2-T12 ClA-24 OS (0) 2 -T5 Br A-63 OS (0) 2 -T12 Cl
A-25 OS(0)2-T6 Br A-64 N(C2H5)2 ClA-25 OS (0) 2 -T6 Br A-64N (C 2 H 5 ) 2 Cl
A-26 OS(0)2-T7 Br A-65 OH FA-26 OS (0) 2 -T7 Br A-65 OH F
A-27 OS(0)2-T8 Br A-66 OCH3 FA-27 OS (0) 2 -T8 Br A-66 OCH 3 F
A-28 OS(0)2-T9 Br A-67 OC(0)CH3 FA-28 OS (0) 2 -T9 Br A-67 OC (0) CH 3 F
A-29 OS(O)2-T10 Br A-68 OC(0)CH2CH3 FA-29 OS (O) 2 -T10 Br A-68 OC (0) CH 2 CH 3 F
A-30 OS(0)2-T1 1 Br A-69 OC(0)CH(CH3)2 FA-30 OS (0) 2 -T1 1 Br A-69 OC (0) CH (CH 3 ) 2 F
A-31 OS(0)2-T12 Br A-70 OC(0)C(CH3)3 FA-31 OS (0) 2 -T12 Br A-70 OC (0) C (CH 3 ) 3 F
A-32 N(C2H5)2 Br A-71 OC(0)-c-C3H5 FA-32N (C 2 H 5 ) 2 Br A-71 OC (0) -cC 3 H 5 F
A-33 OH Cl A-72 OC(0)-C6H5 FA-33 OH Cl A-72 OC (0) -C 6 H 5 F
A-34 OCH3 Cl A-73 OC(0)-CH2C6H5 FA-34 OCH 3 Cl A-73 OC (0) -CH 2 C 6 H 5 F
A-35 OC(0)CH3 Cl A-74 OC(0)CH2CI FA-35 OC (0) CH 3 Cl A-74 OC (0) CH 2 CI F
A-36 OC(0)CH2CH3 Cl A-75 OC(0)-CF3 FA-36 OC (0) CH 2 CH 3 Cl A-75 OC (0) -CF 3 F
A-37 OC(0)CH(CH3)2 Cl A-76 OC(0)-CH2OCH3 FA-37 OC (0) CH (CH 3 ) 2 Cl A-76 OC (0) -CH 2 OCH 3 F
A-38 OC(0)C(CH3)3 Cl A-77 OC(0)-N(CH3)2 FA-38 OC (0) C (CH 3) 3 Cl A-77 OC (0) -N (CH 3) 2 F
A-39 OC(0)-c-C3H5 Cl A-78 OC(0)-OCH2CH3 FA-39 OC (0) -cC 3 H 5 Cl A-78 OC (0) -OCH 2 CH 3 F
A-40 OC(0)-C6H5 Cl A-79 OS(0)2-CH3 FA-40 OC (0) -C 6 H 5 Cl A-79 OS (0) 2 -CH 3 F
A-41 OC(0)-CH2C6H5 Cl A-80 OS(0)2-C2H5 FA-41 OC (0) -CH 2 C 6 H 5 Cl A-80 OS (0) 2 -C 2 H 5 F
A-42 OC(0)CH2CI Cl A-81 OS(0)2-C3H7 FA-42 OC (0) CH 2 CI Cl A-81 OS (0) 2 -C 3 H 7 F
A-43 OC(0)-CF3 Cl A-82 OS(0)2-CH(CH3)2 FA-43 OC (0) -CF 3 Cl A-82 OS (0) 2 -CH (CH 3 ) 2 F
A-44 OC(0)-CH2OCH3 Cl A-83 OS(0)2-C6H5 FA-44 OC (0) -CH 2 OCH 3 Cl A-83 OS (0) 2 -C 6 H 5 F
A-45 OC(0)-N(CH3)2 Cl A-84 OS(0)2-T1 FA-45 OC (0) -N (CH 3 ) 2 Cl A-84 OS (0) 2 -T1 F
A-46 OC(0)-OCH2CH3 Cl A-85 OS(0)2-T2 FA-46 OC (0) -OCH 2 CH 3 Cl A-85 OS (0) 2 -T2 F
A-47 OS(0)2-CH3 Cl A-86 OS(0)2-T3 FA-47 OS (0) 2 -CH 3 Cl A-86 OS (0) 2- T3 F
A-48 OS(0)2-C2H5 Cl A-87 OS(0)2-T4 FA-48 OS (0) 2 -C 2 H 5 Cl A-87 OS (0) 2 -T 4 F
A-49 OS(0)2-C3H7 Cl A-88 OS(0)2-T5 FA-49 OS (0) 2 -C 3 H 7 Cl A-88 OS (0) 2 -T5 F
A-50 OS(0)2-CH(CH3)2 Cl A-89 OS(0)2-T6 FA-50 OS (0) 2 -CH (CH 3 ) 2 Cl A-89 OS (0) 2 -T6 F
A-51 OS(0)2-C6H5 Cl A-90 OS(0)2-T7 FA-51 OS (0) 2 -C 6 H 5 Cl A-90 OS (0) 2 -T7 F
A-52 OS(0)2-T1 Cl A-91 OS(0)2-T8 FA-52 OS (0) 2 -T1 Cl A-91 OS (0) 2 -T8 F
A-53 OS(0)2-T2 Cl A-92 OS(0)2-T9 FA-53 OS (0) 2 -T2 Cl A-92 OS (0) 2 -T9 F
A-54 OS(0)2-T3 Cl A-93 OS(O)2-T10 FA-54 OS (0) 2 -T3 Cl A-93 OS (O) 2 -T10 F
A-55 OS(0)2-T4 Cl A-94 OS(0)2-T1 1 FA-55 OS (0) 2 -T4 Cl A-94 OS (0) 2 -T1 1 F
A-56 OS(0)2-T5 Cl A-95 OS(0)2-T12 FA-56 OS (0) 2 -T5 Cl A-95 OS (0) 2 -T12 F
A-57 OS(0)2-T6 Cl A-96 N(C2H5)2 FA-57 OS (0) 2 -T6 Cl A-96N (C 2 H 5 ) 2 F
A-58 OS(0)2-T7 Cl A-97 OH N02 A-58 OS (0) 2 -T7 Cl A-97 OH N0 2
A-59 OS(0)2-T8 Cl A-98 OCH3 N02 A-59 OS (0) 2 -T8 Cl A-98 OCH 3 NO 2
A-60 OS(0)2-T9 Cl A-99 OC(0)CH3 N02 A-60 OS (0) 2 -T9 Cl A-99 OC (0) CH 3 NO 2
A-61 OS(O)2-T10 Cl A-100 OC(0)CH2CH3 N02 Nr. R R5 Nr. R R5 A-61 OS (O) 2 -T10 Cl A-100 OC (0) CH 2 CH 3 NO 2 No RR 5 No RR 5
A-101 OC(0)CH(CH3)2 N02 A-140 OC(0)-CH2OCH3 CNA-101 OC (0) CH (CH 3 ) 2 NO 2 A-140 OC (0) -CH 2 OCH 3 CN
A-102 OC(0)C(CH3)3 N02 A-141 OC(0)-N(CH3)2 CNA-102 OC (0) C (CH 3) 3 N0 2 A-141 OC (0) -N (CH 3) 2 CN
A-103 OC(0)-c-C3H5 N02 A-142 OC(0)-OCH2CH3 CNA-103 OC (0) -cC 3 H 5 N0 2 A-142 OC (0) -OCH 2 CH 3 CN
A-104 OC(0)-C6H5 N02 A-143 OS(0)2-CH3 CNA-104 OC (0) -C 6 H 5 NO 2 A-143 OS (0) 2 -CH 3 CN
A-105 OC(0)-CH2C6H5 N02 A-144 OS(0)2-C2H5 CNA-105 OC (0) -CH 2 C 6 H 5 NO 2 A-144 OS (0) 2 -C 2 H 5 CN
A-106 OC(0)CH2CI N02 A-145 OS(0)2-C3H7 CNA-106 OC (0) CH 2 CI N0 2 A-145 OS (0) 2 -C 3 H 7 CN
A-107 OC(0)-CF3 N02 A-146 OS(0)2-CH(CH3)2 CNA-107 OC (O) -CF 3 NO 2 A-146 OS (0) 2 -CH (CH 3 ) 2 CN
A-108 OC(0)-CH2OCH3 N02 A-147 OS(0)2-C6H5 CNA-108 OC (0) -CH 2 OCH 3 NO 2 A-147 OS (0) 2 -C 6 H 5 CN
A-109 OC(0)-N(CH3)2 N02 A-148 OS(0)2-T1 CNA-109 OC (0) -N (CH 3 ) 2 NO 2 A-148 OS (0) 2 -T1 CN
A-110 OC(0)-OCH2CH3 N02 A-149 OS(0)2-T2 CNA-110 OC (0) -OCH 2 CH 3 NO 2 A-149 OS (0) 2 -T2 CN
A-11 1 OS(0)2-CH3 N02 A-150 OS(0)2-T3 CNA-11 1 OS (0) 2 -CH 3 N0 2 A-150 OS (0) 2 -T3 CN
A-112 OS(0)2-C2H5 N02 A-151 OS(0)2-T4 CNA-112 OS (0) 2 -C 2 H 5 NO 2 A-151 OS (0) 2 -T4 CN
A-113 OS(0)2-C3H7 N02 A-152 OS(0)2-T5 CNA-113 OS (0) 2 -C 3 H 7 NO 2 A-152 OS (0) 2 -T5 CN
A-114 OS(0)2-CH(CH3)2 N02 A-153 OS(0)2-T6 CNA-114 OS (0) 2 -CH (CH 3 ) 2 NO 2 A-153 OS (0) 2 -T6 CN
A-115 OS(0)2-C6H5 N02 A-154 OS(0)2-T7 CNA-115 OS (0) 2 -C 6 H 5 NO 2 A-154 OS (0) 2 -T7 CN
A-116 OS(0)2-T1 N02 A-155 OS(0)2-T8 CNA-116 OS (0) 2 -T1 N0 2 A-155 OS (0) 2 -T8 CN
A-117 OS(0)2-T2 N02 A-156 OS(0)2-T9 CNA-117 OS (0) 2 -T2 N0 2 A-156 OS (0) 2 -T9 CN
A-118 OS(0)2-T3 N02 A-157 OS(O)2-T10 CNA-118 OS (0) 2 -T3 N0 2 A-157 OS (O) 2 -T10 CN
A-119 OS(0)2-T4 N02 A-158 OS(0)2-T1 1 CNA-119 OS (0) 2 -T4 N0 2 A-158 OS (0) 2 -T1 1 CN
A-120 OS(0)2-T5 N02 A-159 OS(0)2-T12 CNA-120 OS (0) 2 -T5 N0 2 A-159 OS (0) 2 -T12 CN
A-121 OS(0)2-T6 N02 A-160 N(C2H5)2 CNA-121 OS (0) 2 -T6 N0 2 A-160 N (C 2 H 5 ) 2 CN
A-122 OS(0)2-T7 N02 A-161 OH CH3 A-122 OS (0) 2 -T7 N0 2 A-161 OH CH 3
A-123 OS(0)2-T8 N02 A-162 OCH3 CH3 A-123 OS (0) 2 -T8 N0 2 A-162 OCH 3 CH 3
A-124 OS(0)2-T9 N02 A-163 OC(0)CH3 CH3 A-124 OS (0) 2 -T9 NO 2 A-163 OC (0) CH 3 CH 3
A-125 OS(O)2-T10 N02 A-164 OC(0)CH2CH3 CH3 A-125 OS (O) 2 -T10 N0 2 A-164 OC (0) CH 2 CH 3 CH 3
A-126 OS(0)2-T1 1 N02 A-165 OC(0)CH(CH3)2 CH3 A-126 OS (0) 2 -T1 1 NO 2 A-165 OC (0) CH (CH 3 ) 2 CH 3
A-127 OS(0)2-T12 N02 A-166 OC(0)C(CH3)3 CH3 A-127 OS (0) 2 -T12 N0 2 A-166 OC (0) C (CH 3) 3 CH 3
A-128 N(C2H5)2 N02 A-167 OC(0)-c-C3H5 CH3 A-128N (C 2 H 5 ) 2 NO 2 A-167 OC (0) -cC 3 H 5 CH 3
A-129 OH CN A-168 OC(0)-C6H5 CH3 A-129 OH CN A-168 OC (0) -C 6 H 5 CH 3
A-130 OCH3 CN A-169 OC(0)-CH2C6H5 CH3 A-130 OCH 3 CN A-169 OC (0) -CH 2 C 6 H 5 CH 3
A-131 OC(0)CH3 CN A-170 OC(0)CH2CI CH3 A-131 OC (0) CH 3 CN A-170 OC (0) CH 2 Cl CH 3
A-132 OC(0)CH2CH3 CN A-171 OC(0)-CF3 CH3 A-132 OC (0) CH 2 CH 3 CN A-171 OC (O) -CF 3 CH 3
A-133 OC(0)CH(CH3)2 CN A-172 OC(0)-CH2OCH3 CH3 A-133 OC (0) CH (CH 3 ) 2 CN A-172 OC (O) -CH 2 OCH 3 CH 3
A-134 OC(0)C(CH3)3 CN A-173 OC(0)-N(CH3)2 CH3 A-134 OC (0) C (CH 3) 3 CN A-173 OC (0) -N (CH 3) 2 CH 3
A-135 OC(0)-c-C3H5 CN A-174 OC(0)-OCH2CH3 CH3 A-135 OC (0) -cC 3 H 5 CN A-174 OC (O) -OCH 2 CH 3 CH 3
A-136 OC(0)-C6H5 CN A-175 OS(0)2-CH3 CH3 A-136 OC (0) -C 6 H 5 CN A-175 OS (0) 2 -CH 3 CH 3
A-137 OC(0)-CH2C6H5 CN A-176 OS(0)2-C2H5 CH3 A-137 OC (0) -CH 2 C 6 H 5 CN A-176 OS (0) 2 -C 2 H 5 CH 3
A-138 OC(0)CH2CI CN A-177 OS(0)2-C3H7 CH3 A-138 OC (0) CH 2 CI CN A-177 OS (0) 2 -C 3 H 7 CH 3
A-139 OC(0)-CF3 CN A-178 OS(0)2-CH(CH3)2 CH3 Nr. R R5 Nr. R R5 A-139 OC (0) -CF 3 CN A-178 OS (0) 2 -CH (CH 3 ) 2 CH 3 No RR 5 No RR 5
A-179 OS(0)2-C6H5 CH3 A-218 OS(0)2-T7 OCH3 A-179 OS (0) 2 -C 6 H 5 CH 3 A-218 OS (0) 2 -T7 OCH 3
A-180 OS(0)2-T1 CH3 A-219 OS(0)2-T8 OCH3 A-180 OS (0) 2 -T1 CH 3 A-219 OS (0) 2 -T8 OCH 3
A-181 OS(0)2-T2 CH3 A-220 OS(0)2-T9 OCH3 A-181 OS (0) 2 -T2 CH 3 A-220 OS (0) 2 -T9 OCH 3
A-182 OS(0)2-T3 CH3 A-221 OS(O)2-T10 OCH3 A-182 OS (0) 2 -T3 CH 3 A-221 OS (O) 2 -T10 OCH 3
A-183 OS(0)2-T4 CH3 A-222 OS(0)2-T1 1 OCH3 A-183 OS (0) 2 -T4 CH 3 A-222 OS (0) 2 -T1 1 OCH 3
A-184 OS(0)2-T5 CH3 A-223 OS(0)2-T12 OCH3 A-184 OS (0) 2 -T5 CH 3 A-223 OS (0) 2 -T12 OCH 3
A-185 OS(0)2-T6 CH3 A-224 N(C2H5)2 OCH3 A-185 OS (0) 2 -T6 CH 3 A-224N (C 2 H 5 ) 2 OCH 3
A-186 OS(0)2-T7 CH3 A-225 OH CHF2 A-186 OS (0) 2 -T7 CH 3 A-225 OH CHF 2
A-187 OS(0)2-T8 CH3 A-226 OCH3 CHF2 A-187 OS (0) 2 -T8 CH 3 A-226 OCH 3 CHF 2
A-188 OS(0)2-T9 CH3 A-227 OC(0)CH3 CHF2 A-188 OS (0) 2 -T9 CH 3 A-227 OC (0) CH 3 CHF 2
A-189 OS(O)2-T10 CH3 A-228 OC(0)CH2CH3 CHF2 A-189 OS (O) 2 CH 3 A-228 -T10 OC (0) CH 2 CH 3 CHF 2
A-190 OS(0)2-T1 1 CH3 A-229 OC(0)CH(CH3)2 CHF2 A-190 OS (0) 2 -T1 1 CH 3 A-229 OC (0) CH (CH 3 ) 2 CHF 2
A-191 OS(0)2-T12 CH3 A-230 OC(0)C(CH3)3 CHF2 A-191 OS (0) 2 -T12 CH 3 A-230 OC (0) C (CH 3) 3 CHF 2
A-192 N(C2H5)2 CH3 A-231 OC(0)-c-C3H5 CHF2 A-192N (C 2 H 5 ) 2 CH 3 A-231 OC (0) -cC 3 H 5 CHF 2
A-193 OH OCH3 A-232 OC(0)-C6H5 CHF2 A-193 OH OCH 3 A-232 OC (0) -C 6 H 5 CHF 2
A-194 OCH3 OCH3 A-233 OC(0)-CH2C6H5 CHF2 A-194 OCH 3 OCH 3 A-233 OC (0) -CH 2 C 6 H 5 CHF 2
A-195 OC(0)CH3 OCH3 A-234 OC(0)CH2CI CHF2 A-195 OC (0) CH 3 OCH 3 O 234 OC (0) CH 2 CI CHF 2
A-196 OC(0)CH2CH3 OCH3 A-235 OC(0)-CF3 CHF2 A-196 OC (0) CH 2 CH 3 OCH 3 A-235 OC (0) -CF 3 CHF 2
A-197 OC(0)CH(CH3)2 OCH3 A-236 OC(0)-CH2OCH3 CHF2 A-197 OC (0) CH (CH 3 ) 2 OCH 3 A-236 OC (0) -CH 2 OCH 3 CHF 2
A-198 OC(0)C(CH3)3 OCH3 A-237 OC(0)-N(CH3)2 CHF2 A-198 OC (0) C (CH 3 ) 3 OCH 3 A-237 OC (0) -N (CH 3 ) 2 CHF 2
A-199 OC(0)-c-C3H5 OCH3 A-238 OC(0)-OCH2CH3 CHF2 A-199 OC (0) -cC 3 H 5 OCH 3 A-238 OC (0) -OCH 2 CH 3 CHF 2
A-200 OC(0)-C6H5 OCH3 A-239 OS(0)2-CH3 CHF2 A-200 OC (0) -C 6 H 5 OCH 3 A-239 OS (0) 2 -CH 3 CHF 2
A-201 OC(0)-CH2C6H5 OCH3 A-240 OS(0)2-C2H5 CHF2 A-201 OC (0) -CH 2 C 6 H 5 OCH 3 A-240 OS (0) 2 -C 2 H 5 CHF 2
A-202 OC(0)CH2CI OCH3 A-241 OS(0)2-C3H7 CHF2 A-202 OC (0) CH 2 CI OCH 3 A-241 OS (0) 2 -C 3 H 7 CHF 2
A-203 OC(0)-CF3 OCH3 A-242 OS(0)2-CH(CH3)2 CHF2 A-203 OC (0) CF 3 OCH 3 A-242 OS (0) 2 -CH (CH 3 ) 2 CHF 2
A-204 OC(0)-CH2OCH3 OCH3 A-243 OS(0)2-C6H5 CHF2 A-204 OC (0) -CH 2 OCH 3 OCH 3 A-243 OS (0) 2 -C 6 H 5 CHF 2
A-205 OC(0)-N(CH3)2 OCH3 A-244 OS(0)2-T1 CHF2 A-205 OC (0) -N (CH 3 ) 2 OCH 3 A-244 OS (0) 2 -T1 CHF 2
A-206 OC(0)-OCH2CH3 OCH3 A-245 OS(0)2-T2 CHF2 A-206 OC (0) -OCH 2 CH 3 OCH 3 A-245 OS (0) 2 -T2 CHF 2
A-207 OS(0)2-CH3 OCH3 A-246 OS(0)2-T3 CHF2 A-207 OS (0) 2 -CH 3 OCH 3 A-246 OS (0) 2- T3 CHF 2
A-208 OS(0)2-C2H5 OCH3 A-247 OS(0)2-T4 CHF2 A-208 OS (0) 2 -C 2 H 5 OCH 3 A-247 OS (0) 2 -T4 CHF 2
A-209 OS(0)2-C3H7 OCH3 A-248 OS(0)2-T5 CHF2 A-209 OS (0) 2 -C 3 H 7 OCH 3 A-248 OS (0) 2 -T5 CHF 2
A-210 OS(0)2-CH(CH3)2 OCH3 A-249 OS(0)2-T6 CHF2 A-210 OS (0) 2 -CH (CH 3 ) 2 OCH 3 A-249 OS (0) 2 -T6 CHF 2
A-21 1 OS(0)2-C6H5 OCH3 A-250 OS(0)2-T7 CHF2 A-21 1 OS (0) 2 -C 6 H 5 OCH 3 A-250 OS (0) 2 -T7 CHF 2
A-212 OS(0)2-T1 OCH3 A-251 OS(0)2-T8 CHF2 A-212 OS (0) 2 -T1 OCH 3 A-251 OS (0) 2 -T8 CHF 2
A-213 OS(0)2-T2 OCH3 A-252 OS(0)2-T9 CHF2 A-213 OS (0) 2 -T2 OCH 3 A-252 OS (0) 2 -T9 CHF 2
A-214 OS(0)2-T3 OCH3 A-253 OS(O)2-T10 CHF2 A-214 OS (0) 2 -T3 OCH 3 A-253 OS (O) 2 -T10 CHF 2
A-215 OS(0)2-T4 OCH3 A-254 OS(0)2-T1 1 CHF2 A-215 OS (0) 2 -T4 OCH 3 A-254 OS (0) 2 -T1 1 CHF 2
A-216 OS(0)2-T5 OCH3 A-255 OS(0)2-T12 CHF2 A-216 OS (0) 2 -T5 OCH 3 A-255 OS (0) 2 -T12 CHF 2
A-217 OS(0)2-T6 OCH3 A-256 N(C2H5)2 CHF2 Nr. R R5 Nr. R R5 A-217 OS (0) 2 -T6 OCH 3 A-256 N (C 2 H 5 ) 2 CHF 2 No RR 5 No RR 5
A-257 OH CF3 A-296 OC(0)-C6H5 OCHF2 A-257 OH CF 3 A-296 OC (0) -C 6 H 5 OCHF 2
A-258 OCH3 CF3 A-297 OC(0)-CH2C6H5 OCHF2 A-258 OCH 3 CF 3 A-297 OC (0) -CH 2 C 6 H 5 OCHF 2
A-259 OC(0)CH3 CF3 A-298 OC(0)CH2CI OCHF2 A-259 OC (0) CH 3 CF 3 A-298 OC (0) CH 2 Cl OCHF 2
A-260 OC(0)CH2CH3 CF3 A-299 OC(0)-CF3 OCHF2 A-260 OC (0) CH 2 CH 3 CF 3 A-299 OC (O) -CF 3 OCHF 2
A-261 OC(0)CH(CH3)2 CF3 A-300 OC(0)-CH2OCH3 OCHF2 A-261 OC (0) CH (CH 3 ) 2 CF 3 A-300 OC (0) -CH 2 OCH 3 OCHF 2
A-262 OC(0)C(CH3)3 CF3 A-301 OC(0)-N(CH3)2 OCHF2 A-262 OC (0) C (CH 3 ) 3 CF 3 A-301 OC (O) -N (CH 3 ) 2 OCHF 2
A-263 OC(0)-c-C3H5 CF3 A-302 OC(0)-OCH2CH3 OCHF2 A-263 OC (0) -cC 3 H 5 CF 3 A-302 OC (0) -OCH 2 CH 3 OCHF 2
A-264 OC(0)-C6H5 CF3 A-303 OS(0)2-CH3 OCHF2 A-264 OC (0) -C 6 H 5 CF 3 A-303 OS (0) 2 -CH 3 OCHF 2
A-265 OC(0)-CH2C6H5 CF3 A-304 OS(0)2-C2H5 OCHF2 A-265 OC (0) -CH 2 C 6 H 5 CF 3 A-304 OS (0) 2 -C 2 H 5 OCHF 2
A-266 OC(0)CH2CI CF3 A-305 OS(0)2-C3H7 OCHF2 A-266 OC (0) CH 2 Cl CF 3 A-305 OS (0) 2 -C 3 H 7 OCHF 2
A-267 OC(0)-CF3 CF3 A-306 OS(0)2-CH(CH3)2 OCHF2 A-267 OC (0) CF 3 CF 3 A-306 OS (0) 2 -CH (CH 3 ) 2 OCHF 2
A-268 OC(0)-CH2OCH3 CF3 A-307 OS(0)2-C6H5 OCHF2 A-268 OC (O) -CH 2 OCH 3 CF 3 A-307 OS (0) 2 -C 6 H 5 OCHF 2
A-269 OC(0)-N(CH3)2 CF3 A-308 OS(0)2-T1 OCHF2 A-269 OC (O) -N (CH 3 ) 2 CF 3 A-308 OS (0) 2 -T1 OCHF 2
A-270 OC(0)-OCH2CH3 CF3 A-309 OS(0)2-T2 OCHF2 A-270 OC (O) -OCH 2 CH 3 CF 3 A-309 OS (0) 2 -T2 OCHF 2
A-271 OS(0)2-CH3 CF3 A-310 OS(0)2-T3 OCHF2 A-271 OS (0) 2 -CH 3 CF 3 A-310 OS (0) 2 -T3 OCHF 2
A-272 OS(0)2-C2H5 CF3 A-31 1 OS(0)2-T4 OCHF2 A-272 OS (0) 2 -C 2 H 5 CF 3 A-31 1 OS (0) 2 -T4 OCHF 2
A-273 OS(0)2-C3H7 CF3 A-312 OS(0)2-T5 OCHF2 A-273 OS (0) 2 -C 3 H 7 CF 3 A-312 OS (0) 2 -T5 OCHF 2
A-274 OS(0)2-CH(CH3)2 CF3 A-313 OS(0)2-T6 OCHF2 A-274 OS (0) 2 -CH (CH 3 ) 2 CF 3 A-313 OS (0) 2 -T6 OCHF 2
A-275 OS(0)2-C6H5 CF3 A-314 OS(0)2-T7 OCHF2 A-275 OS (0) 2 -C 6 H 5 CF 3 A-314 OS (0) 2 -T7 OCHF 2
A-276 OS(0)2-T1 CF3 A-315 OS(0)2-T8 OCHF2 A-276 OS (0) 2 -T1 CF 3 A-315 OS (0) 2 -T8 OCHF 2
A-277 OS(0)2-T2 CF3 A-316 OS(0)2-T9 OCHF2 A-277 OS (0) 2 -T2 CF 3 A-316 OS (0) 2 -T9 OCHF 2
A-278 OS(0)2-T3 CF3 A-317 OS(O)2-T10 OCHF2 A-278 OS (0) 2 -T3 CF 3 A-317 OS (O) 2 -T 10 OCHF 2
A-279 OS(0)2-T4 CF3 A-318 OS(0)2-T1 1 OCHF2 A-279 OS (0) 2 -T4 CF 3 A-318 OS (0) 2 -T1 1 OCHF 2
A-280 OS(0)2-T5 CF3 A-319 OS(0)2-T12 OCHF2 A-280 OS (0) 2 -T5 CF 3 A-319 OS (0) 2 -T12 OCHF 2
A-281 OS(0)2-T6 CF3 A-320 N(C2H5)2 OCHF2 A-281 OS (0) 2 -T6 CF 3 A-320 N (C 2 H 5 ) 2 OCHF 2
A-282 OS(0)2-T7 CF3 A-321 OH OCF3 A-282 OS (0) 2 -T7 CF 3 A-321 OH OCF 3
A-283 OS(0)2-T8 CF3 A-322 OCH3 OCF3 A-283 OS (0) 2 -T8 CF 3 A-322 OCH 3 OCF 3
A-284 OS(0)2-T9 CF3 A-323 OC(0)CH3 OCF3 A-284 OS (0) 2 -T9 CF 3 A-323 OC (0) CH 3 OCF 3
A-285 OS(O)2-T10 CF3 A-324 OC(0)CH2CH3 OCF3 A-285 OS (O) 2 -T10 CF 3 A-324 OC (0) CH 2 CH 3 OCF 3
A-286 OS(0)2-T1 1 CF3 A-325 OC(0)CH(CH3)2 OCF3 A-286 OS (0) 2 -T1 1 CF 3 A-325 OC (0) CH (CH 3 ) 2 OCF 3
A-287 OS(0)2-T12 CF3 A-326 OC(0)C(CH3)3 OCF3 A-287 OS (0) 2 -T12 CF 3 A-326 OC (0) C (CH 3 ) 3 OCF 3
A-288 N(C2H5)2 CF3 A-327 OC(0)-c-C3H5 OCF3 A-288N (C 2 H 5 ) 2 CF 3 A-327 OC (0) -cC 3 H 5 OCF 3
A-289 OH OCHF2 A-328 OC(0)-C6H5 OCF3 A-289 OH OCHF 2 A-328 OC (0) -C 6 H 5 OCF 3
A-290 OCH3 OCHF2 A-329 OC(0)-CH2C6H5 OCF3 A-290 OCH 3 OCHF 2 A-329 OC (0) -CH 2 C 6 H 5 OCF 3
A-291 OC(0)CH3 OCHF2 A-330 OC(0)CH2CI OCF3 A-291 OC (0) CH 3 OCHF 2 A-330 OC (0) CH 2 Cl OCF 3
A-292 OC(0)CH2CH3 OCHF2 A-331 OC(0)-CF3 OCF3 A-292 OC (0) CH 2 CH 3 OCHF 2 A-331 OC (O) -CF 3 OCF 3
A-293 OC(0)CH(CH3)2 OCHF2 A-332 OC(0)-CH2OCH3 OCF3 A-293 OC (0) CH (CH 3 ) 2 OCHF 2 A-332 OC (O) -CH 2 OCH 3 OCF 3
A-294 OC(0)C(CH3)3 OCHF2 A-333 OC(0)-N(CH3)2 OCF3 A-294 OC (0) C (CH 3 ) 3 OCHF 2 A-333 OC (O) -N (CH 3 ) 2 OCF 3
A-295 OC(0)-c-C3H5 OCHF2 A-334 OC(0)-OCH2CH3 OCF3
Figure imgf000025_0001
A-295 OC (0) -cC 3 H 5 OCHF 2 A-334 OC (O) -OCH 2 CH 3 OCF 3
Figure imgf000025_0001
Die Verbindungen I und deren landwirtschaftlich brauchbaren Salze eignen sich - sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Sie eignen sich als solche oder als entsprechend formuliertes Mittel. Die herbiziden Mittel, die die Verbindung I, insbesondere die bevorzugten Ausgestaltungen davon, enthalten, bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. In Kulturen wie Weizen, Reis, Mais, Soja und Baumwolle wirken sie gegen Unkräuter und Schadgräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor allem bei niedrigen Aufwandmengen auf.  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 herbicidal compositions containing the compound I, in particular the preferred embodiments thereof, control plant growth on non-crop surfaces very well, especially at high application rates. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crops. This effect occurs especially at low application rates.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen I, insbesondere die bevorzugten Ausgestaltungen davon, bzw. sie enthaltende Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen: Depending on the particular application method, 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. For example, the following cultures may be considered:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Avena sati- va, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus li- mon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sati- vus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon ly- copersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vul- garis, Picea abies, Pinus spec, Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis und pru- nus domestica, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays. Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapeseed, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus lichen, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris. 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.
Der Begriff Kulturpflanzen schließt auch solche ein, die durch Züchtung, Mutagenese oder gentechnische Methoden verändert wurden. Gentechnisch veränderte Pflanzen sind Pflanzen, deren genetisches Material in einer Weise verändert worden ist, wie sie unter natürlichen Bedingungen durch Kreuzen, Mutationen oder natürliche Rekombination (d.h. Neuzusammenstellung der Erbinformation) nicht vorkommt. Dabei werden in der Regel ein oder mehrere Gene in das Erbgut der Pflanze integriert, um die Eigenschaften der Pflanze zu verbessern. The term 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). As a rule, one or more genes are integrated into the genome of the plant in order to improve the properties of the plant.
Der Begriff Kulturpflanzen umfasst somit auch Pflanzen, die durch züchterische und gentechnische Maßnahmen eine Toleranz gegen bestimmter Herbizidklassen, wie Hydroxyphenylpyruvat-Dioxygenase (HPPD)-Inhibitoren, Acetolactat-Synthase (ALS)- Inhibitoren, wie z. B. Sulfonylharnstoffe (EP-A 257 993, US 5,013,659) oder Imidazoli- none (siehe z. B. US 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218,  The term 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.
WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357,
WO 03/13225, WO 03/14356, WO 04/16073), Enolpyruvylshikimat-3-Phosphat- Synthase (EPSPS)-lnhibitoren wie z. B. Glyphosat (siehe z. B. WO 92/00377), Gluta- minsynthetase (GS)-lnhibitoren wie z. B. Glufosinat (siehe z. B. EP-A 242 236, EP-A 242 246) oder Oxynil-Herbizide (siehe z. B. US 5,559,024) erworben haben. 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).
Mit Hilfe klassischer Züchtungsmethoden (Mutagenese) wurden zahlreiche Kulturpflanzen, z. B. Clearfield®-Raps, erzeugt, die eine Toleranz gegen Imidazolinone, z. B. Imazamox, haben. Mit Hilfe gentechnischer Methoden wurden Kulturpflanzen, wie Soja, Baumwolle, Mais, Rüben und Raps, erzeugt, die resistent gegen Glyphosat oder Glufosinat sind, erzeugt, welche unter den Handelsnamen RoudupReady® (Glyphosat) und Liberty Link® (Glufosinat) erhältlich sind. With the help of classical breeding methods (mutagenesis) numerous crops, eg. As Clearfield® rapeseed, which produces a tolerance to imidazolinones, z. As imazamox, have. Using genetic engineering methods, 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.
Der Begriff Kulturpflanzen umfasst somit auch Pflanzen, die mit Hilfe gentechnischer Maßnahmen ein oder mehrere Toxine, z. B. solche aus dem Bakterienstamm Bacillus ssp., produzieren. Toxine, die durch solche gentechnisch veränderten Pflanzen hergestellt werden, umfassen z. B. Insektizide Proteine von Bacillus spp., insbesondere von B. thuringiensis, wie die Endotoxine CrylAb, CrylAc, Cryl F, Cry1 Fa2, Cry2Ab, Cry3A, Cry3Bb1 , Cry9c, Cry34Ab1 oder Cry35Ab1 ; oder vegetative Insektizide Proteine (VIPs), z. B. VIP1 , VIP2, VIP3, oder VIP3A; Insektizide Proteine von Nematoden- kolonisierenden Bakterien, z. B. Photorhabdus spp. oder Xenorhabdus spp.; Toxine aus tierischen Organismen, z. B. Wepsen,-, Spinnen- oder Skorpionstoxine; pilzliche Toxine, z. B. aus Streptomyceten; pflanzliche Lektine, z. B. aus Erbse oder Gerste; Aggluti- nine; Proteinase-Inhibitoren, z. B. Trypsin-Inhibitoren, Serinprotease-Inhibitoren, Pata- tin, Cystatin oder Papain-Inhibitoren; Ribosomen-inaktivierende Proteine (RIPs), z. B. Ricin, Mais-RIP, Abrin, Luffin, Saporin oder Bryodin; Steroid-metabolisierende Enzyme, z. B. 3-Hydroxysteroid-Oxidase, Ecdysteroid-IDP-Glycosyl-Transferase, Cholesterinoxi- dase, Ecdyson-Inhibitoren oder HMG-CoA-Reduktase; lonenkanalblocker, z. B. Inhibitoren von Natrium- oder Calziumkanälen; Juvenilhormon-Esterase; Rezeptoren für das diuretischen Hormon (Helicokininrezeptoren); Stilbensynthase, Bibenzylsynthase, Chi- tinasen und Glucanasen. Diese Toxine können in den Pflanzen auch als Prätoxine, Hybridproteine, verkürzte oder anderweitig modfizierte Proteine produziert werden. Hybridproteine zeichnen sich durch eine neue Kombination von verschiedenen Proteindomänen aus (siehe z. B. WO 2002/015701 ). Weitere Besipiele für derartige Toxine oder gentechnisch veränderte Pflanzen, die diese Toxine produzieren sind in EP- A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, The term 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. 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. Ricin, corn RIP, abrin, luffin, saporin or bryodin; 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 channels; Juvenile hormone esterase; Receptors for the diuretic hormone (helicokinin receptors); Stilbene synthase, bibenzyl synthase, chitinases and glucanases. These 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 und WO 03/052073 offenbart. Die Methoden zur Herstellung dieser gentechnisch veränderten Pflanzen sind dem Fachmann bekannt und z. B. in den oben erwähnten Publikationen dargelegt. Zahlreiche der zuvor genannten Toxine verleihen den Pflanzen, die diese produzieren, eine Toleranz gegen Schädlinge aus allen taxo- nomischen Arthropodenklassen, insbesondere gegen Käfer (Coeleropta), Zweiflügler (Diptera) und Schmetterlinge (Lepidoptera) und gegen Nematoden (Nematoda). 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. 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).
Gentechnisch veränderte Pflanzen, die ein oder mehrere Gene, die für Insektizide Toxine kodieren, produzieren sind z. B. in den oben erwähnten Publikationen beschrieben und zum Teil kommerziell erhältlich, wie z. B. YieldGard® (Maissorten, die das Toxin CrylAb produzieren), YieldGard® Plus (Maissorten, die die Toxine CrylAb und Cry3Bb1 produzieren), Starlink® (Maissorten, die das Toxin Cry9c produzieren), Herculex® RW (Maissorten, die die Toxine Cry34Ab1 , Cry35Ab1 und das Enzym Phosphinothricin-N- Acetyltransferase [PAT] produzieren); NuCOTN® 33B (Baumwollsorten, die das Toxin CrylAc produzieren), Bollgard® I (Baumwollsorten, die das Toxin CrylAc produzieren), Bollgard® II (Baumwollsorten, die die Toxine CrylAc und Cry2Ab2 produzieren); VIP- COT® (Baumwollsorten, die ein VIP-Toxin produzieren); NewLeaf® (Kartoffelsorten, die das Toxin Cry3A produzieren); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Protec- ta®, Bt1 1 (z. B. Agrisure® CB) und Bt176 von Syngenta Seeds SAS, Frankreich, (Maissorten, die das Toxin CrylAb und das PAT-Enyzm produzieren), MIR604 von Syngenta Seeds SAS, Frankreich (Maissorten, die ein modifizierte Version des Toxins Cry3A produzieren, siehe hierzu WO 03/018810), MON 863 von Monsanto Europe S.A., Belgien (Maissorten, die das Toxin Cry3Bb1 produzieren), IPC 531 von Monsanto Europe S.A., Belgien (Baumwollsorten, die eine modifizierte Version des Toxins CrylAc produzieren) und 1507 von Pioneer Overseas Corporation, Belgien (Maissorten, die das Toxin Cryl F und das PAT-Enyzm produzieren). Genetically engineered plants that produce one or more genes encoding insecticidal toxins, e.g. As described in the publications mentioned above and partly commercially available, such as. B. 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 phosphinothricin N-acetyltransferase [PAT] produce); NuCOTN ® 33B (cotton cultivars producing the toxin CrylAc), Bollgard ® I (cotton cultivars producing the toxin CrylAc), Bollgard ® II (cotton cultivars producing the toxins CrylAc and Cry2Ab2); VIP COT ® (cotton cultivars producing a VIP-toxin); NewLeaf ® (potato cultivars producing the Cry3A toxin); Bt Xtra ®, NatureGard® ®, KnockOut ®, BiteGard ®, Protec ta ®, Bt1 1 (z. B. Agrisure ® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which the toxin CrylAb and the PAT Producing enzyme), MIR604 from Syngenta Seeds SAS, France (maize varieties producing a modified version of the toxin Cry3A, see WO 03/018810), MON 863 from Monsanto Europe SA, Belgium (maize varieties producing the toxin Cry3Bb1), IPC 531 from Monsanto Europe SA, Belgium (cotton varieties that produce a modified version of the toxin CrylAc) and 1507 from Pioneer Overseas Corporation, Belgium (maize varieties that produce the toxin Cryl F and the PAT enzyme).
Der Begriff Kulturpflanzen umfasst somit auch Pflanzen, die mit Hilfe gentechnischer Maßnahmen ein oder mehrere Proteine produzieren, die eine erhöhte Resistenz oder Widerstandfähigkeit gegen bakterielle, virale oder pilzliche Pathogene bewirken, wie z. B. sogenannte Pathogenesis-related-Proteine (PR-Proteine, siehe EP-A 0 392 225), Resistenzproteine (z. B. Kartoffelsorten, die zwei Resistenzgene gegen Phytophthora infestans aus der mexikanischen Wildkartoffel Solanum bulbocastanum produzieren) oder T4-Lysozym (z. B. Kartoffelsorten, die durch die Produktion diese Proteins resistent gegen Bakterien wie Erwinia amylvora ist). The term 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) or T4 lysozyme (eg, potato varieties that are resistant to bacteria such as Erwinia amylvora as a result of the production of this protein).
Der Begriff Kulturpflanzen umfasst somit auch Pflanzen, deren Produktivität mit Hilfe gentechnischer Methoden verbessert wurde, indem z. B. die Ertragsfähigkeit (z. B. Biomasse, Kornertrag, Stärke-, Öl- oder Proteingehalt), die Toleranz gegenüber Trockenheit, Salz oder anderen begrenzenden Umweltfaktoren oder die Widerstandsfähigkeit gegenüber Schädlingen und pilzlichen, bakteriellen und viralen Pathogenen gesteigert wird.  The term crops thus also includes plants whose productivity has been improved by means of genetic engineering methods by z. For example, 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.
Der Begriff Kulturpflanzen umfasst auch Pflanzen, deren Inhaltsstoffe insbesondere zur Verbesserung der menschlichen oder tierischen Ernährung mit Hilfe gentechnischer Methoden verändert wurden, indem z. B. Ölpflanzen gesundheitsfördernde langkettige Omega-3-Fettsäuren oder einfach ungesättigte Omega-9-Fettsäuren (z. B. Nexera®- Raps) produzieren. The term 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.
Der Begriff Kulturpflanzen umfasst auch Pflanzen, die zur verbesserten Produktion von Rohstoffen mit Hilfe gentechnischer Methoden verändert wurden, indem z. B. der Amylopektin-Gehalt von Kartoffeln (Amflora®-Kartoffel) erhöht wurde. The term crops also includes plants that have been modified for the improved production of raw materials by means of genetic engineering methods by z. B. the amylopectin content of potatoes (Amflora ® potato) was increased.
Des Weiteren wurde gefunden, dass die Verbindungen der Formel I auch zur Defolia- tion und/oder Desikkation von Pflanzenteilen geeignet ist, wofür Kulturpflanzen wie Baumwolle, Kartoffel, Raps, Sonnenblume, Sojabohne oder Ackerbohnen, insbesondere Baumwolle, in Betracht kommen. Diesbezüglich wurden Mittel zur Desikkation und /oder Defoliation von Pflanzen, Verfahren zur Herstellung dieser Mittel und Verfahren zur Desikkation und/oder Defoliation von Pflanzen mit der Verbindungen der Formel I gefunden.  Furthermore, it has been found that 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. In this regard, 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.
Als Desikkantien eignen sich die Verbindungen der Formel I insbesondere zur Austrocknung der oberirdischen Teile von Kulturpflanzen wie Kartoffel, Raps, Sonnenblume und Sojabohne aber auch Getreide. Damit wird ein vollständig mechanisches Beernten dieser wichtigen Kulturpflanzen ermöglicht.  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.
Von wirtschaftlichem Interesse ist ferner die Ernteerleichterung, die durch das zeitlich konzentrierte Abfallen oder Vermindern der Haftfestigkeit am Baum bei Zitrusfrüchten, Oliven oder bei anderen Arten und Sorten von Kern-, Stein- und Schalenobst ermöglicht wird. Derselbe Mechanismus, d.h., die Förderung der Ausbildung von Trenngewebe zwischen Frucht- oder Blatt- und Sprossteil der Pflanzen ist auch für ein gut kontrollierbares Entblättern von Nutzpflanzen, insbesondere Baumwolle, wesentlich. Of economic interest is also the harvest relief, which is made possible by the time-concentrated dropping or reducing the adhesion to the tree in citrus fruits, olives or other types and varieties of pome, stone and peel fruit. The same mechanism, i.e. promoting the formation of release webs between fruit or leaf and shoot part of the plants, is also essential for a well controllable defoliation of crops, especially cotton.
Außerdem führt die Verkürzung des Zeitintervalls, in dem die einzelnen Baumwollpflanzen reif werden, zu einer erhöhten Qualität der Faser nach der Ernte.  In addition, shortening the time interval in which the individual cotton plants ripen results in increased fiber quality after harvest.
Die Verbindungen I bzw. die sie enthaltenden herbiziden Mittel können beispielsweise in Form von direkt versprühbaren wäßrigen Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen, Gießen oder Behandlung des Saatgutes bzw. Mischen mit dem Saatgut angewendet werden. Die Anwendungsformen richten sich nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten. 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.
Die herbiziden Mittel enthalten eine herbizid wirksame Menge mindestens einer Verbindung der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsstoffe.  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.
Beispiele für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel sind inerte Hilfsstoffe, feste Trägerstoffe, oberflächenaktive Stoffe (wie Dispergiermittel Schutzkolloide, Emulgatoren, Netzmittel und Haftmittel), organische und anorganische Verdicker, Bakterizide, Frostschutzmittel, Entschäumer ggf. Farbstoffe und für Saatgutformulierungen Kleber.  Examples of the formulation of pesticides conventional auxiliaries are 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.
Beispiele für Verdicker (d.h. Verbindungen, die der Formulierung ein modifiziertes Fließverhalten verleihen, d.h. hohe Viskosität im Ruhezustand und niedrige Viskosität im bewegten Zustand) sind Polysaccharide wie Xanthan Gum (Kelzan® der Fa. Kelco), Rhodopol® 23 (Rhone Poulenc) oder Veegum® (Firma R.T. Vanderbilt) sowie organische und anorganische Schichtmineralienwie Attaclay® (Firma Engelhardt).  Examples of thickeners (ie, compounds which impart modified flowability to the formulation, ie, high-level at low viscosity and low viscosity in the agitated state) are 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).
Beispiele für Antischaummittel sind Silikonemulsionen (wie z.Bsp. Silikon® SRE, Firma Wacker oder Rhodorsil® der Firma Rhodia ), langkettige Alkohole, Fettsäuren, Salze von Fettsäuren, fluororganische Verbindungen und deren Gemische.  Examples of antifoams are 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.
Bakterizide können zur Stabilisierung der wäßrigen Herbizid-Formulierung zugesetzt werden. Beispiele für Bakterizide sind Bakterizide basierend auf Diclorophen und Ben- zylalkoholhemiformal (Proxel® der Fa. ICI oder Acticide® RS der Fa. Thor Chemie und Kathon® MK der Firma Rohm & Haas) sowie Isothiazolinonderivaten wie Alkylisothiazo- linonen und Benzisothiazolinonen (Acticide MBS der Fa. Thor Chemie)  Bactericides may be added to stabilize the aqueous herbicidal formulation. Examples of 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)
Beispiele für Frostschutzmittel sind Ethylenglycol, Propylenglycol, Harnstoff oder Gly- cerin.  Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.
Beispiele für Farbmittel sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.l. Pigment Red 1 12 und C.l. Solvent Red 1 bekannten Farbstoffe, sowie 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.  Examples of 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.
Beispiele für Kleber sind Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Als inerte Zusatzstoffe kommen beispielsweise in Betracht: Examples of adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. Suitable inert additives are, for example:
Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kerosin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, alkylierte Benzole oder deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol, Cyclohexanol, Ketone wie Cycloh- exanon oder stark polare Lösungsmittel, z. B. Amine wie N-Methylpyrrolidon oder Wasser.  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.
Feste Trägerstoffe sind Mineralerden wie Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.  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.
Als oberflächenaktive Stoffe (Adjuvantien, Netz-, Haft-, Dispergier- sowie Emulgiermittel) kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Ligninsulfonsäuren (z.B. Borrespers-Typen, Borregaard), Phenolsulfonsäuren, Naphthalinsulfonsäuren (Morwet-Typen, Akzo Nobel) und Dibutylnaphthalinsulfonsäure (Nekal-Typen, BASF SE), sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octa- decanolen sowie von Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethylen- octylphenolether, ethoxyliert.es Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tribu- tylphenylpolyglykolether, Alkylarylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethy- lenoxid-Kondensate, ethoxyliert.es Rizinusöl, Polyoxyethylenalkylether oder Polyoxy- propylenalkylether, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin-Sulfitablau- gen sowie Proteine, denaturierte Proteine, Polysaccharide (z.B. Methylcellulose), hydrophob modifizierte Stärken, Polyvinylalkohol (Mowiol typen Clariant), Polycarboxylate (BASF SE, Sokalan-Typen), Polyalkoxylate, Polyvinylamin (BASF SE, Lupamin-Typen), Polyethylenimin (BASF SE, Lupasol-Typen) , Polyvinylpyrrolidon und deren Copolyme- re in Betracht.  As surfactants (adjuvants, wetting agents, tackifiers, dispersants and emulsifiers), the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Ligninsulfonsäuren (eg, Borrespers types, Borregaard), phenolsulfonic acids, naphthalenesulfonic (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), as well as 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 naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated.is isooctyl-, octyl- or Nonylphenol, alkylphenyl, tributylphenyl polyglycol ethers, alkylarylpolyether alcohols, isotridecylalcohol, fatty alcohol ethylenoxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulphite precipitates and proteins, denatured proteins, polysaccharides (eg. 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.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.  Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden.  Granules, e.g. Coating, impregnation and homogeneous granules can be prepared by binding the active compounds to solid carriers.
Wässrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergierbaren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Verbindungen der Formel I oder la als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser ho- mogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind. Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare 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. However, it is also possible to prepare concentrates consisting of active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, which are suitable for dilution with water.
Die Konzentrationen der Verbindungen der Formel I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Die Formulierungen enthalten im Allgemeinen 0,001 bis 98 Gew.-%, vorzugsweise 0,01 bis 95 Gew.-%, mindestens eines Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Spektrum) eingesetzt.  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).
Die erfindungsgemäßen Verbindungen I können beispielsweise wie folgt formuliert werden: The compounds I according to the invention can be formulated, for example, as follows:
1. Produkte zur Verdünnung in Wasser  1. Products for dilution in water
A Wasserlösliche Konzentrate  A Water-soluble concentrates
10 Gew.-Teile Wirkstoff werden mit 90 Gew.-Teilen Wasser oder einem wasserlöslichen Lösungsmittel gelöst. Alternativ werden Netzmittel oder andere Hilfsmittel zugefügt. Bei der Verdünnung in Wasser löst sich der Wirkstoff. Man erhält auf diese Weise eine Formulierung mit 10 Gew.-% Wirkstoffgehalt. 10 parts by weight of active compound are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content.
B Dispergierbare Konzentrate  B Dispersible concentrates
20 Gew.-Teile Wirkstoff werden in 70 Gew.-Teilen Cyclohexanon unter Zusatz von 10 Gew.-Teilen eines Dispergiermittels z.B. Polyvinylpyrrolidon gelöst. Bei Verdünnung in Wasser ergibt sich eine Dispersion. Der Wirkstoffgehalt beträgt 20 Gew.-% 20 parts by weight of active compound 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. The active ingredient content is 20% by weight
C Emulgierbare Konzentrate  C Emulsifiable concentrates
15 Gew.-Teile Wirkstoff werden in 75 Gew.-Teilen eines organisches Lösungsmittels (z.B. Alkylaromaten)-unter Zusatz von Ca-Dodecylbenzolsulfonat und Ricinusölethoxy- lat (jeweils 5 Gew.-Teile) gelöst. Bei der Verdünnung in Wasser ergibt sich eine Emulsion. Die Formulierung hat 15 Gew.-% Wirkstoffgehalt. 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.
D Emulsionen  D emulsions
25 Gew.-Teile Wirkstoff werden in 35 Gew.-Teilen eines organisches Lösungsmittels (z.B. Alkylaromaten) unter Zusatz von Ca-Dodecylbenzolsulfonat und Ricinusölethoxy- lat (jeweils 5 Gew.-Teile) gelöst. Diese Mischung wird mittels einer Emulgiermaschine (z.B. Ultraturax) in 30 Gew.Teile Wasser gegeben und zu einer homogenen Emulsion gebracht. Bei der Verdünnung in Wasser ergibt sich eine Emulsion. Die Formulierung hat einen Wirkstoffgehalt von 25 Gew.-%.  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). 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.
E Suspensionen  E suspensions
20 Gew.-Teile Wirkstoff werden unter Zusatz von 10 Gew.-Teilen Dispergier- und Netzmitteln und 70 Gew.-Teilen Wasser oder einem organischen Lösungsmittel in einer Rührwerkskugelmühle zu einer feinen Wirkstoffsuspension zerkleinert. Bei der Verdünnung in Wasser ergibt sich eine stabile Suspension des Wirkstoffs. Der Wirkstoffgehalt in der Formulierung beträgt 20 Gew.-% .  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.
F Wasserdispergierbare und wasserlösliche Granulate  F Water-dispersible and water-soluble granules
50 Gew.-Teile Wirkstoff werden unter Zusatz von 50 Gew-Teilen Dispergier- und Netz- mittein fein gemahlen und mittels technischer Geräte (z.B. Extrusion, Sprühturm, Wirbelschicht) als wasserdispergierbare oder wasserlösliche Granulate hergestellt. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs. Die Formulierung hat einen Wirkstoffgehalt von 50 Gew.-%. 50 parts by weight of active compound 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.
G Wasserdispergierbare und wasserlösliche Pulver  G Water-dispersible and water-soluble powders
75 Gew.-Teile Wirkstoff werden unter Zusatz von 25 Gew.-Teilen Dispergier- und Netzmitteln sowie Kieselsäuregel in einer Rotor-Strator Mühle vermählen. Bei der Verdünnung in Wasser ergibt sich eine stabile Dispersion oder Lösung des Wirkstoffs. Der Wirkstoffgehalt der Formulierung beträgt 75 Gew.-%. 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.
H Gelformulierungen  H gel formulations
In einer Kugelmühle werden 20 Gew.-Teile Wirkstoff, 10 Gew.-Teile Dispergiermittel, 1 Gew.-Teil Geliermittel und 70 Gew.-Teile Wasser oder eines organischen Lösungsmittels zu einer feinen Suspension vermählen. Bei der Verdünnung mit Wasser ergibt sich eine stabile Suspension mit 20 Gew.-% Wirkstoffgehalt.  In a ball mill, 20 parts by weight of the active ingredient, 10 parts by weight of the dispersant, 1 part by weight of the gelling agent and 70 parts by weight of water or an organic solvent are ground to a fine suspension. Dilution with water results in a stable suspension with 20% by weight active ingredient content.
2. Produkte für die Direktapplikation 2. Products for direct application
I Stäube  I dusts
5 Gew.-Teile Wirkstoff werden fein gemahlen und mit 95 Gew.-Teilen feinteiligem Kaolin innig vermischt. Man erhält dadurch ein Stäubemittel mit 5 Gew.-% Wirkstoffgehalt. 5 parts by weight of active compound are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content.
J Granulate (GR, FG, GG, MG) J Granules (GR, FG, GG, MG)
0,5 Gew-Teile Wirkstoff werden fein gemahlen und mit 99,5 Gewichtsteilen Trägerstoffe verbunden. Gängige Verfahren sind dabei die Extrusion, die Sprühtrocknung oder die Wirbelschicht. Man erhält dadurch ein Granulat für die Direktapplikation mit 0,5 Gew.-% Wirkstoffgehalt. 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.
K ULV- Lösungen (UL)  K ULV solutions (UL)
10 Gew.-Teile Wirkstoff werden in 90 Gew.-Teilen eines organischen Lösungsmittels z.B. Xylol gelöst. Dadurch erhält man ein Produkt für die Direktapplikation mit 10 Gew.- % Wirkstoffgehalt. 10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent, e.g. Xylene dissolved. This gives a product for direct application with 10% by weight of active ingredient content.
Die Applikation der Verbindungen I oder der sie enthaltenden herbiziden Mittel kann im Vorauflauf-, im Nachauflaufverfahren oder zusammen mit dem Saatgut einer Kulturpflanze erfolgen. Es besteht auch die Möglichkeit, die herbiziden Mittel bzw. Wirkstoffe dadurch zu applizieren, dass mit den herbiziden Mitteln bzw. Wirkstoffen vorbehandeltes Saatgut einer Kulturpflanze ausgebracht wird. Sind die Wirkstoffe für gewisse Kulturpflanzen weniger verträglich, so können Ausbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spritzgeräte so gespritzt werden, daß die Blätter der empfindlichen Kulturpflanzen nach Möglichkeit nicht getroffen werden, während die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post-directed, lay-by). In einer weiteren Ausführungsform kann die Applikation der Verbindungen der Formel I bzw. der herbiziden Mittel durch Behandlung von Saatgut erfolgen. 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.
Die Behandlung von Saatgut umfasst im Wesentlichen alle dem Fachmann geläufigen Techniken (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping, und seed pelleting) basierend auf den erfindungsgemäßen Verbindungen der Formel I bzw. daraus hergestellten Mitteln. Hierbei können die herbiziden Mittel verdünnt oder unverdünnt aufgetragen werden.  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. Here, the herbicidal agents can be diluted or applied undiluted.
Der Begriff Saatgut umfasst Saatgut aller Arten, wie z.B. Körner, Samen, Früchte, Knollen, Stecklinge und ähnliche Formen. Bevorzugt beschreibt der Begriff Saatgut hier Körner und Samen.  The term seed includes seeds of all kinds, e.g. Grains, seeds, fruits, tubers, cuttings and similar forms. The term seed preferably describes grains and seeds here.
Als Saatgut kann Saatgut der oben erwähnten Nutzpflanzen aber auch das Saatgut transgener oder durch herkömmliche Züchtungsmethoden erhaltener Pflanzen eingesetzt werden.  Seeds of the abovementioned crops but also the seeds of transgenic or obtained by conventional breeding methods plants can be used as seeds.
Die Aufwandmengen an Wirkstoff betragen je nach Bekämpfungsziel, Jahreszeit, Zielpflanzen und Wachstumsstadium 0.001 bis 3.0, vorzugsweise 0.01 bis 1 .0 kg/ha aktive Substanz (a. S.). Zur Saatgutbehandlung werden die Verbindungen I üblicherweise in Mengen von 0,001 bis 10 kg pro 100 kg Saatgut eingesetzt. Depending on the control target, season, target plants and growth stage, 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.). For seed treatment, the compounds I are usually used in amounts of 0.001 to 10 kg per 100 kg of seed.
Es kann auch von Vorteil sein, die Verbindungen der Formel I in Kombination mit Safenern zu verwenden. Safener sind chemische Verbindungen, die Schaden an Nutzpflanzen verhindern oder reduzieren, ohne die herbizide Wirkung der Verbindungen der Formel I auf unerwünschte Pflanzen wesentlich zu beeinflussen. Sie können sowohl vor der Aussaat (beispielsweise bei Saatgutbehandlungen, bei Stecklingen oder Setzlingen) als auch im Vor- oder Nachauflauf der Nutzpflanze verwendet werden. Die Safener und die Verbindungen der Formel I können gleichzeitig oder nacheinander verwendet werden. Geeignete Safener sind beispielsweise (Chinolin-8-oxy)essigsäuren, 1 - Phenyl-5-haloalkyl-1 H-1 ,2,4-triazol-3-carbonsäuren, 1 -Phenyl-4,5-dihydro-5-alkyl-1 H- pyrazol-3,5-dicarbonsäuren, 4,5-Dihydro-5,5-diaryl-3-isoxazolcarbonsäuren, Dichloroa- cetamide, alpha-Oximinophenylacetonitrile, Acetophenonoxime, 4,6-Dihalo-2- phenylpyrimidine, N-[[4-(Aminocarbonyl)phenyl]sulfonyl]-2-benzoesäureamide, 1 ,8- Naphthalsäureanhydrid, 2-Halo-4-(haloalkyl)-5-thiazolcarbonsäuren, Phosphorthiolate und N-Alkyl-O-phenylcarbamate sowie ihre landwirtschaftlich brauchbaren Salze, und vorausgesetzt sie haben eine Säurefunktion, ihre landwirtschaftlich brauchbaren Derivate, wie Amide, Ester und Thioester. It may also be advantageous to use the compounds of the formula I in combination with safeners. 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-phenylcarbamates and their agriculturally useful salts, and provided they have an acid function, their agriculturally useful derivatives such as amides, esters and thioesters.
Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die Verbindungen der Formel I mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen oder mit Safenern gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner 1 ,2,4- Thiadiazole, 1 ,3,4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Ami- notriazole, Anilide, Aryloxy-/Heteroaryloxyalkansäuren und deren Derivate, Benzoesäure und deren Derivate, Benzothiadiazinone, 2-(Hetaroyl/Aroyl)-1 ,3-cyclohexandione, Heteroaryl-Aryl-Ketone, Benzylisoxazolidinone, meta-CF3-Phenylderivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracetanilide, Cyclohexenonoximetherde- rivate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydrobenzofurane, Dihydro- furan-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N- Phenyl-3,4,5,6-tetrahydrophthalimide, Oxadiazole, Oxirane, Phenole, Aryloxy- und He- teroaryloxyphenoxypropionsäureester, Phenylessigsäure und deren Derivate, 2-Phe- nylpropionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincar- bonsäure und deren Derivate, Pyrimidylether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide, Uracile sowie Phenylpyrazoline und Iso- xazoline und deren Derivate in Betracht. To widen the spectrum of action and to achieve synergistic effects, 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. For example, 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-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and derivatives thereof, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uracils and P henylpyrazoline and isoxazolines and their derivatives into consideration.
Außerdem kann es von Nutzen sein, die Verbindungen I allein oder in Kombination mit anderen Herbiziden oder auch noch mit weiteren Pflanzenschutzmitteln gemischt, gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung von Ernährungs- und Spurenelementmängeln eingesetzt werden. Es können auch weitere Additve wie nicht phytotoxische Öle und Ölkonzentrate zugesetzt werden.  In addition, it may be useful to use the compounds I alone or in combination with other herbicides or even mixed with other crop protection agents, together, for example, with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used for the elimination of nutritional and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.
Beispiele für Herbizide, die in Kombination mit den Verbindungen der Formel I gemäß der vorliegenden Erfindung verwendet werden können, sind:  Examples of herbicides which can be used in combination with the compounds of the formula I according to the present invention are:
b1 ) aus der Gruppe der Lipid-Biosynthese-Inhibitoren:  b1) from the group of lipid biosynthesis inhibitors:
Alloxydim, Alloxydim-natrium, Butroxydim, Clethodim, Clodinafop, Clodinafop-propargyl, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Diclofop, Diclofop-methyl, Fenoxaprop, Feno- xaprop-ethyl, Fenoxaprop-P, Fenoxaprop-P-ethyl, Fluazifop, Fluazifop-butyl, Fluazifop- P, Fluazifop-P-butyl, Haloxyfop, Haloxyfop-methyl, Haloxyfop-P, Haloxyfop-P-methyl, Metamifop, Pinoxaden, Profoxydim, Propaquizafop, Quizalofop, Quizalofop-ethyl, Qui- zalofop-tefuryl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Sethoxydim, Tepraloxydim, Tralkoxydim, Benfuresat, Butylat, Cycloat, Dalapon, Dimepiperat, EPTC, Esprocarb, Ethofumesat, Flupropanat, Molinat, Orbencarb, Pebulat, Prosulfocarb, TCA, Thiobencarb, Tiocarbazil, Triallat und Vernolat; Alloxydim, alloxydim-sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-p-ethyl, fluazifop, Fluazifop-butyl, Fluazifop-P, Fluazifop-P-butyl, Haloxyfop, Haloxyfop-methyl, Haloxyfop-P, Haloxyfop-P-methyl, Metamifop, Pinoxaden, Profoxydim, Propaquizafop, Quizalofop, Quizalofop-ethyl, Quizalofop-tefuryl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Sethoxydim, Tepraloxydim, Tralkoxydim, Benfuresat, Butylate, Cycloat, Dalapon, Dimepiperate, EPTC, Esprocarb, Ethofumesate, Flupropanate, Molinate, Orbencarb, Pebulate, Prosulfocarb, TCA, Thiobencarb, tiocarbazil, triallate and vernolate;
b2) aus der Gruppe der ALS-Inhibitoren:  b2) from the group of ALS inhibitors:
Amidosulfuron, Azimsulfuron, Bensulfuron, Bensulfuron-methyl, Bispyribac, Bispyribac- natrium, Chlorimuron, Chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Cloransulam, Cloransulam-methyl, Cyclosulfamuron, Diclosulam, Ethametsulfuron, Ethametsulfuron- methyl, Ethoxysulfuron, Flazasulfuron, Florasulam, Flucarbazon, Flucarbazon-natrium, Flucetosulfuron, Flumetsulam, Flupyrsulfuron, Flupyrsulfuron-methyl-natrium, Foram- sulfuron, Halosulfuron, Halosulfuron-methyl, Imazamethabenz, Imazamethabenz- methyl, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, lodo- sulfuron, lodosulfuron-methyl-natrium, Mesosulfuron, Metosulam, Metsulfuron, Metsul- furon-methyl, Nicosulfuron, Orthosulfamuron, Oxasulfuron, Penoxsulam, Primisulfuron, Primisulfuron-methyl, Propoxycarbazon, Propoxycarbazon-natrium, Prosulfuron, Pyra- zosulfuron, Pyrazosulfuron-ethyl, Pyribenzoxim, Pyrimisulfan, Pyriftalid, Pyriminobac, Pyriminobac-methyl, Pyrithiobac, Pyrithiobac-natrium, Pyroxsulam, Rimsulfuron, Sulfo- meturon, Sulfometuron-methyl, Sulfosulfuron, Thiencarbazon, Thiencarbazon-methyl, Thifensulfuron, Thifensulfuron-methyl, Triasulfuron, Tribenuron, Tribenuron-methyl, Trifloxysulfuron, Triflusulfuron, Triflusulfuron-methyl und Tritosulfuron; Amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac-sodium, chlorimuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cloransulam, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, Flucarbazone sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foram-sulfurone, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, lodosulfuron- Methyl Sodium, Mesosulfuron, Metosulam, Metsulfuron, Metsul- furon-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxime, pyrimisulfan, pyriftalid, pyriminobac, pyriminobac-methyl, pyrithiobac, pyrithiobac sodium, pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron;
b3) aus der Gruppe der Photosynthese-Inhibitoren:  b3) from the group of photosynthesis inhibitors:
Ametryn, Amicarbazon, Atrazin, Bentazon, Bentazon-natrium, Bromacil, Bromofenoxim, Bromoxynil und seine Salze und Ester, Chlorobromuron, Chloridazon, Chlorotoluron, Chloroxuron, Cyanazin, Desmedipham, Desmetryn, Dimefuron, Dimethametryn, Diquat, Diquat-dibromid, Diuron, Fluometuron, Hexazinon, loxynil und seine Salze und Ester, Isoproturon, Isouron, Karbutilat, Lenacil, Linuron, Metamitron, Methabenzthiazuron, Metobenzuron, Metoxuron, Metribuzin, Monolinuron, Neburon, Paraquat, Paraquat- dichlorid, Paraquat-dimetilsulfat, Pentanochlor, Phenmedipham, Phenmedipham-ethyl, Prometon, Prometryn, Propanil, Propazin, Pyridafol, Pyridat, Siduron, Simazin, Si- metryn, Tebuthiuron, Terbacil, Terbumeton, Terbuthylazin, Terbutryn, Thidiazuron und Trietazin; Ametryn, amicarbazone, atrazine, bentazone, bentazone sodium, bromacil, bromofenoxime, bromoxynil and its salts and esters, chlorobromuron, chloridazon, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn, diquat, diquat-dibromide, diuron, fluometuron , Hexazinone, loxynil and its salts and esters, isoproturon, isourone, carbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat-dichloride, paraquat-dimetilsulfate, pentanochlor, phenmedipham, phenmedipham- ethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, symmetry, tebuthiuron, terbacil, terbumetone, terbuthylazine, terbutryn, thidiazuron and trietazine;
b4) aus der Gruppe der Protoporphyrinogen-IX-Oxidase-lnhibitoren:  b4) from the group of protoporphyrinogen IX oxidase inhibitors:
Acifluorfen, Acifluorfen-natrium, Azafenidin, Bencarbazon, Benzfendizon, Bifenox, Buta- fenacil, Carfentrazon, Carfentrazon-ethyl, Chlomethoxyfen, Cinidon-ethyl, Fluazolat, Flufenpyr, Flufenpyr-ethyl, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Fluoroglyco- fen, Fluoroglycofen-ethyl, Fluthiacet, Fluthiacet-methyl, Fomesafen, Halosafen, Lacto- fen, Oxadiargyl, Oxadiazon, Oxyfluorfen, Pentoxazon, Profluazol, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Saflufenacil, Sulfentrazon, Thidiazimin, 2-Chlor-5-[3,6-dihydro-3- methyl-2,6-dioxo-4-(trifluormethyl)-1 (2H)-pyrimidinyl]-4-fluor-N-[(isopropyl)methylsulf- amoyl]benzamid (H-1 ; CAS 372137-35-4), [3-[2-Chlor-4-fluor-5-(1 -methyl-6-trifluor- methyl-2,4-dioxo-1 ,2,3,4,-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]essigsäure- ethylester (H-2; CAS 353292-31 -6), N-Ethyl-3-(2,6-dichlor-4-trifluormethylphenoxy)-5- methyl-1 H-pyrazol-1 -carboxamid (H-3; CAS 452098-92-9), N-Tetrahydrofurfuryl-3-(2,6- dichlor-4-trifluormethylphenoxy)-5-methyl-1 H-pyrazol-1 -carboxamid (H-4; CAS 915396- 43-9), N-Ethyl-3-(2-chlor-6-fluor-4-trifluormethylphenoxy)-5-methyl-1 H-pyrazol-1 -carboxamid (H-5; CAS 452099-05-7) und N-Tetrahydrofurfuryl-3-(2-chlor-6-fluor-4-trifluor- methylphenoxy)-5-methyl-1 H-pyrazol-1 -carboxamid (H-6; CAS 45100-03-7); Acifluorfen, acifluorfen sodium, azafenidine, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidone-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pentyl, flumioxazine, fluoroglycofene, Fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazole, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimine, 2-chloro-5- [3 , 6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl) -1 (2H) -pyrimidinyl] -4-fluoro-N - [(isopropyl) methylsulfamoyl] benzamide (H-1; CAS 372137-35-4), [3- [2-chloro-4-fluoro-5- (1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-3 -yl) phenoxy] -2-pyridyloxy] acetic acid ethyl ester (H-2; CAS 353292-31 -6), N-ethyl-3- (2,6-dichloro-4-trifluoromethylphenoxy) -5-methyl-1H pyrazole-1-carboxamide (H-3; CAS 452098-92-9), N-tetrahydrofurfuryl-3- (2,6-dichloro-4-trifluoromethylphenoxy) -5-methyl-1 H-pyrazole-1-carboxamide (H-4; CAS 915396-43-9), N-ethyl-3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1-carboxamide (H-5; CAS 452099-05- 7) and N-tetrahydrofurfuryl-3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1-carboxamide (H-6; CAS 45100-03-7);
b5) aus der Gruppe der Bleacher-Herbizide:  b5) from the group of bleacher herbicides:
Aclonifen, Amitrol, Beflubutamid, Benzobicyclon, Benzofenap, Clomazon, Diflufeni- can, Fluridon, Flurochloridon, Flurtamon, Isoxaflutol, Mesotrion, Norflurazon, Picolina- fen, Pyrasulfutol, Pyrazolynat, Pyrazoxyfen, Sulcotrion, Tefuryltrion, Tembotrion, Top- ramezon, 4-Hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluormethyl)-3-pyridyl]car- bonyl]bicyclo[3.2.1 ]oct-3-en-2-one (H-7; CAS 352010-68-5) und 4-(3-Trifluormethyl- phenoxy)-2-(4-trifluormethylphenyl)pyrimidin (H-8; CAS 180608-33-7); b6) aus der Gruppe der EPSP-Synthase-lnhibitoren: Aclonifen, Amitrole, Beflubutamide, Benzobicyclone, Benzofenap, Clomazone, Diflufenicanone, Fluridone, Flurochloridone, Flurtamone, Isoxaflutole, Mesotrione, Norflurazon, Picolinefine, Pyrasulfutole, Pyrazolynate, Pyrazoxyfen, Sulcotrione, Tefuryltrione, Tembotrione, Topramezone, 4- Hydroxy-3 - [[2 - [(2-methoxyethoxy) methyl] -6- (trifluoromethyl) -3-pyridyl] carbonyl] bicyclo [3.2.1] oct-3-en-2-one (H-7 CAS 352010-68-5) and 4- (3-trifluoromethylphenoxy) -2- (4-trifluoromethylphenyl) pyrimidine (H-8; CAS 180608-33-7); b6) from the group of EPSP synthase inhibitors:
Glyphosat, Glyphosat-isopropylammonium und Glyphosat-trimesium (Sulfosat); Glyphosate, glyphosate isopropylammonium and glyphosate trimesium (sulfosate);
b7) aus der Gruppe der Glutamin-Synthase-Inhibitoren:  b7) from the group of glutamine synthase inhibitors:
Bilanaphos (Bialaphos), Bilanaphos-natrium, Glufosinat und Glufosinat-ammonium; b8) aus der Gruppe der DHP-Synthase-Inhibitoren: Asulam; Bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium; b8) from the group of DHP synthase inhibitors: asulam;
b9) aus der Gruppe der Mitose-Inhibitoren:  b9) from the group of mitosis inhibitors:
Amiprophos, Amiprophos-methyl, Benfluralin, Butamiphos, Butralin, Carbetamid, Chlorpropham, Chlorthal, Chlorthal-dimethyl, Dinitramin, Dithiopyr, Ethalfluralin, Flu- chloralin, Oryzalin, Pendimethalin, Prodiamin, Propham, Propyzamid, Tebutam, Thia- zopyr und Trifluralin; Amiprophos, Amiprophos-methyl, Benfluralin, Butamiphos, Butraline, Carbetamide, Chlorpropham, Chlorthal, Chlorthal-dimethyl, Dinitramine, Dithiopyr, Ethalfluralin, Fluchlorine, Oryzalin, Pendimethalin, Prodiamine, Propham, Propyzamide, Tebutam, Thiazopyr and Trifluralin;
b10) aus der Gruppe der VLCFA-Inhibitoren:  b10) from the group of VLCFA inhibitors:
Acetochlor, Alachlor, Anilofos, Butachlor, Cafenstrol, Dimethachlor, Dimethanamid, Di- methenamid-P, Diphenamid, Fentrazamid, Flufenacet, Mefenacet, Metazachlor, Meto- lachlor, Metolachlor-S, Naproanilid, Napropamid, Pethoxamid, Piperophos, Pretilachlor, Propachlor, Propisochlor, Pyroxasulfon (KIH-485) und Thenylchlor; 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;
Verbindungen der Formel 2:
Figure imgf000036_0001
Compounds of the formula 2:
Figure imgf000036_0001
worin die Variablen folgende Bedeutungen haben: wherein the variables have the following meanings:
Y Phenyl oder 5- oder 6-gliedriges Heteroaryl wie eingangs definiert, welche durch eine bis drei Gruppen RAA substituiert sein können; R21 ,R22,R23,R24 H, Halogen, oder Ci- C4-Alkyl; X O oder NH; n 0 oder 1. 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.
Figure imgf000036_0002
Figure imgf000036_0002
wobei # die Bindung zu dem Molekülgerüst bedeutet; und  where # is the bond to the molecular skeleton; and
R2 ,R22,R23,R24 H, Cl, F oder CH3; R25 Halogen, Ci-C4-Alkyl oder Ci-C4-Haloalkyl; R26 d-C4-Alkyl; R27 Halogen, Ci-C4-Alkoxy oder Ci-C4-Haloalkoxy; R28 H, Halogen, Ci-C4- Alkyl, Ci-C4-Haloalkyl oder Ci-C4-Haloalkoxy; m 0, 1 , 2 oder 3; X Sauerstoff; 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; X oxygen;
n 0 oder 1. n 0 or 1.
Bevorzugte Verbindungen der Formel 2 weisen folgende Be  Preferred compounds of formula 2 have the following Be
Figure imgf000036_0003
Figure imgf000036_0003
R2 H; R22, R23 F; R24 H oder F; X Sauerstoff; n 0 oder 1. R 2 H; R 22, R 23 F; R 24 H or F; X oxygen; n 0 or 1.
Besonders bevorzugte Verbindungen der Formel 2 sind: 3-[5-(2,2-Difluor-ethoxy)-1 -methyl-3-trifluormethyl-1 H-pyrazol-4-ylmethansulfonyl]-4- fluor-5,5-dimethyl-4,5-dihydro-isoxazol (2-1 ); 3-{[5-(2,2-Difluor-ethoxy)-1 -methyl-3-tri- fluormethyl-1 H-pyrazol-4-yl]-fluor-methansulfonyl}-5,5-dimethyl-4,5-dihydro-isoxazol (2- 2); 4-(4-Fluor-5,5-dimethyl-4,5-dihydro-isoxazol-3-sulfonylmethyl)-2-methyl-5-trifluor- methyl-2H-[1 ,2,3]triazol (2-3); 4-[(5,5-Dimethyl-4,5-dihydro-isoxazol-3-sulfonyl)-fluor- methyl]-2-methyl-5-trifluormethyl-2H-[1 ,2,3]triazol (2-4); 4-(5,5-Dimethyl-4,5-dihydro- isoxazol-3-sulfonylmethyl)-2-methyl-5-trifluormethyl-2H-[1 ,2,3]triazol (2-5); 3-{[5-(2,2- Difluor-ethoxy)-1 -methyl-3-trifluormethyl-1 H-pyrazol-4-yl]-difluor-methansulfonyl}-5,5- dimethyl-4,5-dihydro-isoxazol (2-6); 4-[(5,5-Dimethyl-4,5-dihydro-isoxazol-3-sulfonyl)- difluor-methyl]-2-methyl-5-trifluormethyl-2H-[1 ,2,3]triazol (2-7); 3-{[5-(2,2-Difluor- ethoxy)-1 -methyl-3-trifluormethyl-1 H-pyrazol-4-yl]-difluor-methansulfonyl}-4-fluor-5,5- dimethyl-4,5-dihydro-isoxazol (2-8); 4-[Difluor-(4-fluor-5,5-dimethyl-4,5-dihydro-isoxazol- 3-sulfonyl)-methyl]-2-methyl-5-trifluormethyl-2H-[1 ,2,3]triazol (2-9); 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-sulfonyl) fluoromethyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-4 ); 4- (5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonylmethyl) -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-5); 3 - {[5- (2,2-Difluoro-ethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] -difluoro-methanesulfonyl} -5,5-dimethyl-4,5-dihydro -isoxazole (2-6); 4 - [(5,5-Dimethyl-4,5-dihydro-isoxazol-3-sulfonyl) -difluoro-methyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-7 ); 3 - {[5- (2,2-difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] difluoro-methanesulfonyl} -4-fluoro-5,5-dimethyl-4 , 5-dihydroisoxazole (2-8); 4- [Difluoro (4-fluoro-5,5-dimethyl-4,5-dihydro-isoxazol-3-sulfonyl) -methyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-9);
b1 1 ) aus der Gruppe der Cellulose-Biosynthese-Inhibitoren:  b1 1) from the group of cellulose biosynthesis inhibitors:
Chlorthiamid, Dichlobenil, Flupoxam und Isoxaben; Chlorthiamide, Dichlobenil, Flupoxam and Isoxaben;
b12) aus der Gruppe der Entkoppler-Herbizide:  b12) from the group of decoupling herbicides:
Dinoseb, Dinoterb und DNOC und seine Salze; Dinoseb, Dinoterb and DNOC and its salts;
b13) aus der Gruppe der Auxin-Herbizide:  b13) from the group of auxin herbicides:
2,4-D und seine Salze und Ester, 2,4-DB und seine Salze und Ester, Aminopyralid und seine Salze wie Aminopyralid-tris(2-hydroxypropyl)ammonium und seine Ester, Benazolin, Benazolin-ethyl, Chloramben und seine Salze und Ester, Clomeprop, Clopy- ralid und seine Salze und Ester, Dicamba und seine Salze und Ester, Dichlorprop und seine Salze und Ester, Dichlorprop-P und seine Salze und Ester, Fluroxypyr, Fluroxy- pyr-butometyl, Fluroxypyr-meptyl, MCPA und seine Salze und Ester, MCPA-thioethyl, MCPB und seine Salze und Ester, Mecoprop und seine Salze und Ester, Mecoprop-P und seine Salze und Ester, Picloram und seine Salze und Ester, Quinclorac, Quinme- rac, TBA (2,3,6) und seine Salze und Ester, Triclopyr und seine Salze und Ester, und 5,6-Dichlor-2-cyclopropyl-4-pyrimidincarbonsäure (H-9; CAS 858956-08-8) und seine Salze und Ester;  2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts, such as aminopyralid tris (2-hydroxypropyl) ammonium and its esters, benazoline, benazolin-ethyl, chloroamben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quineme-rac, TBA (2, 3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS 858956-08-8) and its salts and esters;
b14) aus der Gruppe der Auxin-Transport-Inhibitoren: Diflufenzopyr, Diflufenzopyr- natrium, Naptalam und Naptalam-natrium;  b14) from the group of auxin transport inhibitors: diflufenzopyr, diflufenzopyrsodium, naptalam and naptalam sodium;
b15) aus der Gruppe der sonstigen Herbizide: Bromobutid, Chlorflurenol, Chlor- flurenol-methyl, Cinmethylin, Cumyluron, Dalapon, Dazomet, Difenzoquat, Difenzoquat- metilsulfate, Dimethipin, DSMA, Dymron, Endothal und seine Salze, Etobenzanid, Flamprop, Flamprop-isopropyl, Flamprop-methyl Flamprop-M-isopropyl, Flamprop-M- methyl, Flurenol, Flurenol-butyl, Flurprimidol, Fosamin, Fosamine-ammonium, Indano- fan, Maleinsäure-hydrazid, Mefluidid, Metam, Methylazid, Methylbromid, Methyl-dym- ron, Methyljod id. MSMA, Ölsäure, Oxaziclomefon, Pelargonsäure, Pyributicarb, Quino- clamin, Triaziflam, Tridiphan und 6-Chlor-3-(2-cyclopropyl-6-methylphenoxy)-4-pyrida- zinol (H-10; CAS 499223-49-3) und seine Salze und Ester. Beispiele für bevorzugte Safener C sind Benoxacor, Cloquintocet, Cyometrinil, Cy- prosulfamid, Dichlormid, Dicyclonon, Dietholate, Fenchlorazol, Fenclorim, Flurazol, Flu- xofenim, Furilazol, Isoxadifen, Mefenpyr, Mephenat, Naphthalsäureanhydrid, Oxabetri- nil, 4-(Dichloracetyl)-1 -oxa-4-azaspiro[4.5]decan (H-1 1 ; MON4660, CAS 71526-07-3) und 2,2,5-Trimethyl-3-(dichloracetyl)-1 ,3-oxazolidin (H-12; R-29148, CAS 52836-31 -4). De Wirkstoffe der Gruppen b1 ) bis b15) und die Safener C sind bekannte Herbizide und Safener, siehe z. B. The Compendium of Pesticide Common Names b15) from the group of the other herbicides: bromobutide, chlorofluorol, chlorofluorolmethyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metylsulfates, dimethipine, DSMA, dymron, endothal and its salts, etobenzanide, flamprop, flamprop- isopropyl, flamprop-methyl flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indan fan, maleic hydrazide, mefluidide, metam, methyl azide, methyl bromide, methyl dym - ron, methyl iodine id. 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
(http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, R. R. Schmidt, Herbizide, Georg Thieme Verlag, Stuttgart 1995. Weitere herbizide Wirkstoffe sind aus WO 96/26202, WO 97/41 1 16, WO 97/41 1 17, WO 97/41 1 18, WO 01/83459 und WO (Http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, RR Schmidt, herbicides, Georg Thieme Verlag, Stuttgart 1995. Further herbicidal active ingredients are known from WO 96/26202, WO 97/41 1 16, WO 97/41 1 17, WO 97/41 1 18 , WO 01/83459 and WO
2008/074991 sowie aus W. Krämer et al. (ed.) "Modern Crop Protection Compounds", Vol. 1 , Wiley VCH, 2007 und der darin zitierten Literatur bekannt. 2008/074991 as well as from W. Krämer et al. (ed.) "Modern Crop Protection Compounds", Vol. 1, Wiley VCH, 2007 and the literature cited therein.
Die Erfindung betrifft auch Zusammensetzungen in Form eines als 1 -Komponentenzusammensetzung formulierten Pflanzenschutzmittels, enthaltend eine Wirkstoffkombination, die wenigstens eine Verbindung der Formel I und wenigstens einen weiteren Wirkstoff, bevorzugt ausgewählt aus den Wirkstoffen der Gruppen b1 bis b15, und wenigstens einen festen oder flüssigen Träger und/oder eine oder mehrere grenzflächenaktive Substanzen und gewünschtenfalls einen oder mehrere für Pflanzenschutzmittel übliche weitere Hilfsstoffe. 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.
Die Erfindung betrifft auch Zusammensetzungen in Form eines als 2-Komponenten- zusammensetzung formulierten Pflanzenschutzmittels, umfassend eine erste Komponente, enthaltend wenigstens eine Verbindung der Formel I, einen festen oder flüssigen Träger und/oder eine oder mehrere grenzflächenaktive Substanzen, und eine zweite Komponente, enthaltend wenigstens einen weiteren Wirkstoff, ausgewählt aus den Wirkstoffen der Gruppen b1 bis b15, einem festen oder flüssigen Träger und/oder eine oder mehrere grenzflächenaktive Substanzen, wobei zusätzlich beide Komponenten auch weitere, für Pflanzenschutzmittel üblichen Hilfsmittel enthalten können.  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.
In binären Zusammensetzungen, die wenigstens eine Verbindung der Formel I als Komponente A und wenigstens ein Herbizid B enthalten, liegt das Gewichtsverhältnis der Wirkstoffe A:B in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 .  In binary compositions containing at least one compound of the formula I as component A and at least one herbicide B, the weight ratio of the active compounds A: B is generally in the range 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.
In binären Zusammensetzungen, die wenigstens eine Verbindung der Formel I als Komponente A und wenigstens einen Safener C enthalten, liegt das Gewichtsverhältnis der Wirkstoffe A:C in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 .  In binary compositions which comprise at least one compound of the formula I as component A and at least one safener C, the weight ratio of the active compounds A: C is generally in the range 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.
In ternären Zusammensetzungen, die sowohl wenigstens eine Verbindung der Formel I als Komponente A, wenigstens ein Herbizid B und wenigstens einen Safener C enthalten, liegen die relativen Gewichtsanteile der Komponenten A:B in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 , das Gewichtsverhältnis der Komponente A:C in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 , und das Gewichtsverhältnis der Komponenten B:C in der Regel im Bereich von 1 :1000 bis 1000:1 , vorzugsweise im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1 . Vorzugsweise liegt das Gewichtsverhältnis der Komponenten A + B zur Komponente C im Bereich von 1 :500 bis 500:1 , insbesondere im Bereich von 1 :250 bis 250:1 und besonders bevorzugt im Bereich von 1 :75 bis 75:1. In ternary compositions which contain both at least one compound of the formula I as component A, at least one herbicide B and at least one safener C, the relative proportions by weight of the components A: B are generally in the range 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 in the range from 1: 250 to 250: 1 and particularly preferably in the range from 1: 75 to 75: 1.
Die Verbindungen I und die erfindungsgemäßen Zusammensetzungen können auch eine pflanzenstärkende Wirkung aufweisen. Sie eigenen sich daher zu Mobilisierung pflanzeneigener Abwehrkräfte gegen Befall durch unerwünschte Mikroorganismen, wie Schadpilze, aber auch Viren und Bakterien. Unter pflanzenstärkenden (resistenzinduzierenden) Stoffen sind in diesem Zusammenhang solche Substanzen zu verstehen, die in der Lage sind, das Abwehrsystem von behandelten Pflanzen so zu stimulieren, dass diese bei nachfolgender Inokulation mit unerwünschten Mikroorganismen weitgehende Resistenz gegen diese Mikroorganismen entfalten. 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. In this context, 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.
Die Verbindungen I können eingesetzt werden, um Pflanzen innerhalb eines gewissen Zeitraumes nach der Behandlung gegen den Befall durch unerwünschte Mikroorganismen zu schützen. Der Zeitraum, innerhalb dessen Schutz herbeigeführt wird, erstreckt sich im Allgemeinen auf 1 bis 28 Tage, vorzugsweise 1 bis 14 Tage nach der Behandlung der Pflanzen mit den Verbindungen I bzw. nach Behandlung des Saatguts, auf bis zu 9 Monate nach Aussaat.  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.
Die Verbindungen I und die erfindungsgemäßen Zusammensetzungen eignen sich auch zur Steigerung des Ernteertrages.  The compounds I and the compositions according to the invention are also suitable for increasing crop yield.
Sie sind außerdem mindertoxisch und weisen eine gute Pflanzenverträglichkeit auf.  They are also low toxicity and have good plant tolerance.
Im Folgenden wird die Herstellung von Verbindungen der Formel I anhand von Beispielen erläutert. The preparation of compounds of the formula I is explained below by way of examples.
Synthesebeispiele synthesis Examples
Die in den nachstehenden Synthesebeispielen wiedergegebenen Vorschriften wurden unter entsprechender Abwandlung der Ausgangsverbindungen zur Gewinnung weiterer Verbindungen I benutzt. Die so erhaltenen Verbindungen sind in der anschließenden Tabelle mit physikalischen Angaben aufgeführt. Die Charakterisierung der im Folgenden gezeigten Produkte erfolgte durch Bestimmung des Schmelzpunktes, durch NMR-Spektroskopie oder anhand der durch MS-Spektro- metrie ermittelten Massen [m/z]. The instructions given in the Synthesis Examples below were used with appropriate modification of the starting compounds to obtain further compounds I. The compounds thus obtained are listed in the following table with physical data. The characterization of the products shown below was carried out by determining the melting point, by NMR spectroscopy or by the masses determined by MS spectrometry [m / z].
MS: Quadrupol Elektrospray-Ionisation, 80 V (Positiv-Modus).]  MS: Quadrupole electrospray ionization, 80V (positive mode).]
I. Herstellungsbeispiele I. Preparation Examples
Beispiel 1 : Herstellung von 7-(2,2-Difluor-ethoxy)-1 -methyl-6-(2-trifluormethyl-phenyl)- 1 ,4-dihydro-imidazo[4,5-b]pyridin-5-on Example 1: Preparation of 7- (2,2-difluoro-ethoxy) -1-methyl-6- (2-trifluoromethyl-phenyl) -1,4-dihydro-imidazo [4,5-b] pyridin-5-one
1 .a) Stufe 1 : 3-Methyl-5-[2-(2-trifluormethyl-phenyl)-acetylamino]-3H-imidazol-4- carbonsäureethylester  1 .a) Step 1: Ethyl 3-methyl-5- [2- (2-trifluoromethylphenyl) acetylamino] -3H-imidazole-4-carboxylate
Eine Lösung von 2,5g 5-Amino-3-methyl-3H-imidazol-4-carbonsäureethylester in 30ml Dichlormethan wurde mit 2,5g (2-Trifluormethlyphenyl)-essigsäurechlorid und 2,24g Triethylamin versetzt. Die Mischung wurde 16 Sd. gerührt, dann mit Wasser und gesätt. NaCI-Lösung gewaschen, getrocknet und vom Lösungsmittel befreit. Das Rohprodukt wurde an einer Si02-Säule mit Petrolether-Essigester chromatographiert; man erhielt 2g der Titelverbindung als farblose Kristalle. To a solution of 2.5 g of ethyl 5-amino-3-methyl-3H-imidazole-4-carboxylate in 30 ml of dichloromethane was added 2.5 g of (2-trifluoromethlyphenyl) -acetic acid chloride and 2.24 g of triethylamine. The mixture was 16 sd. stirred, then with water and sat. NaCl solution, dried and freed from the solvent. The crude product was chromatographed on a SiO 2 column with petroleum ether-ethyl acetate; 2 g of the title compound were obtained as colorless crystals.
H-NMR (CDCIs): 8,47 (s); 7,72 (d); 7,62 (t); 7,53 (d); 7,48 (t); 5,48 (s); 4,37 (q); 4,08 (s); 3,65 (s); 1 ,37 (t).  H-NMR (CDCIs): 8.47 (s); 7.72 (d); 7.62 (t); 7.53 (d); 7.48 (t); 5.48 (s); 4.37 (q); 4.08 (s); 3.65 (s); 1, 37 (t).
1 .b) Stufe 2: 7-Hydroxy-1 -methyl-6-(2-trifluormethyl-phenyl)-1 ,4-dihydro-imidazo[4,5- b]pyridin-5-on 1 b) Step 2: 7-Hydroxy-1-methyl-6- (2-trifluoromethyl-phenyl) -1,4-dihydro-imidazo [4,5-b] pyridin-5-one
Eine Lösung von 1 ,6g des Esters aus Stufe 1 in 5ml DMF wurde mit 0,72g Natriumhydrid (60%ig) bei 0°C versetzt. Die Mischung wurde 16h gerührt, dann 50ml Wasser zugegeben und mit Essigester extrahiert. Die wässrige Phase wurde mit 2N HCl auf pH 3 angesäuert, mit Essigester extrahiert, der Essigester mit Wasser und gesättigter NaCI-Lösung gewaschen, getrocknet und eingeengt. Das Rohprodukt wurde aus Methanol umkristallisiert. Man erhielt 0,7g der Titelverbindung als farblose Kristalle. To a solution of 1.6 g of the ester from Step 1 in 5 ml of DMF was added 0.72 g of 60% sodium hydride at 0 ° C. The mixture was stirred for 16 h, then 50 ml of water added and extracted with ethyl acetate. The aqueous phase was acidified to pH 3 with 2N HCl, extracted with ethyl acetate, the ethyl acetate washed with water and saturated NaCl solution, dried and concentrated. The crude product was recrystallized from methanol. 0.7 g of the title compound were obtained as colorless crystals.
H-NMR (CDCIs): 7,95 (s); 7,74 (d); 7,65 (t); 7,52 (t); 7,25 (d), 3,71 (s).  H-NMR (CDCIs): 7.95 (s); 7.74 (d); 7.65 (t); 7.52 (t); 7.25 (d), 3.71 (s).
MS (M+H): m/z=309,9  MS (M + H): m / z = 309.9
1 c) Stufe 3: 7-(2,2-Difluorethoxy)-1 -methyl-6-(2-trifluormethyl-phenyl)-1 ,4-dihydro- imidazo[4,5-b]pyridin-5-on 1 c) Step 3: 7- (2,2-Difluoroethoxy) -1-methyl-6- (2-trifluoromethyl-phenyl) -1,4-dihydro-imidazo [4,5-b] pyridin-5-one
Zu einer Lösung von 0,5g des Pyridins aus Stufe 2 in 5ml Acetonitril wurden 0,41 g Diisopropylamin und 0,69g 2,2-Difluorethoxy-trifluormethansulfonat gegeben und 16 Std. gerührt. Die Mischung wurde mit Wasser und Essigester versetzt, mit gesättigter NaCI-Lösung gewaschen, getrocknet und eingeengt. Nach Reinigung mit präparativer Si02-Dünnschichtchromatographie wurden 66mg der Titelverbindung als farbloses Öl erhalten. To a solution of 0.5 g of the pyridine from Step 2 in 5 ml of acetonitrile was added 0.41 g of diisopropylamine and 0.69 g of 2,2-difluoroethoxy-trifluoromethanesulfonate and stirred for 16 hrs. The mixture was mixed with water and ethyl acetate, washed with saturated NaCl solution, dried and concentrated. After purification by preparative SiO 2 thin-layer chromatography, 66 mg of the title compound were obtained as a colorless oil.
H-NMR (CDCIs): 8,26 (s); 7,77 (d); 7,64 (t); 7,54 (t); 7,31 (d); 6,5-5,5 (m); 5,0-4,5 (m); 3,86 (s). MS (M+H): m/z=374,0 H-NMR (CDCIs): 8.26 (s); 7.77 (d); 7.64 (t); 7.54 (t); 7,31 (d); 6.5-5.5 (m); 5.0-4.5 (m); 3.86 (s). MS (M + H): m / z = 374.0
Beispiel 2: Herstellung von 7-Hydroxy-1 -methyl-6-(2-trifluormethyl-phenyl)-1 H- pyrano[3,2-c]pyrazol-5-on Example 2: Preparation of 7-hydroxy-1-methyl-6- (2-trifluoromethyl-phenyl) -1H-pyrano [3,2-c] pyrazol-5-one
2.a) Stufe 1 : 3-(4-Benzyloxy-2-methyl-2H-pyrazol-3-yl)-3-hydroxy-2-(2-trifluormethyl- phenyl)-acrylsäuremethylester  2.a) Step 1: 3- (4-Benzyloxy-2-methyl-2H-pyrazol-3-yl) -3-hydroxy-2- (2-trifluoromethyl-phenyl) -acrylic acid methyl ester
Zu einer Lösung von 1 ,16g 4-Benzyloxy-2-methyl-2H-pyrazol-3-carbonsäure in 20ml DMF wurden 0,89g Carbonyldiimidazol zugegeben, nach 30 min Rühren wurde bei -40°C 1 ,2g (2-Trifluoromethylphenyl)-essigsäuremethlyester und 0,4g Natriumhydrid zugegeben. Die Mischung wurde bei 20-25°C 16 Std. gerührt, Wasser zugegeben, mit 2N HCl auf pH5-6 eingestellt und mit Essigester extrahiert. Die organische Phase wurde getrocknet und eingeengt. Der ölige Rückstand (1 .07 g) wurde ohne weitere Reinigung in der nächsten Stufe eingesetzt. To a solution of 1.16 g of 4-benzyloxy-2-methyl-2H-pyrazole-3-carboxylic acid in 20 ml of DMF was added 0.89 g of carbonyldiimidazole, after stirring for 30 min at -40 ° C 1, 2g (2-trifluoromethylphenyl) acetic acid methyl ester and 0.4 g of sodium hydride are added. The mixture was stirred at 20-25 ° C for 16 hrs, added water, adjusted to pH5-6 with 2N HCl and extracted with ethyl acetate. The organic phase was dried and concentrated. The oily residue (1.07 g) was used without further purification in the next step.
H-NMR (CDCIs): 7,70 (d); 7,63 (d); 7,53 (t); 7,43 (t); 7,35 (s); 5,57 (s); 3,76 (s); 3,59 (s).  H-NMR (CDCIs): 7.70 (d); 7.63 (d); 7.53 (t); 7.43 (t); 7.35 (s); 5.57 (s); 3.76 (s); 3.59 (s).
2.b) Stufe 2: 7-Hydroxy-1 -methyl-6-(2-trifluormethyl-phenyl)-1 H-pyrano[3,2-c]pyrazol- 5-on  2.b) Step 2: 7-Hydroxy-1-methyl-6- (2-trifluoromethylphenyl) -1H-pyrano [3,2-c] pyrazol-5-one
Eine Lösung von 0,83g des Esters aus Stufe 1 in 5ml DMSO wurde bei 1 10°C 16 Std. gerührt. Nach Einengen der Lösung wurde der Rückstand mit praperativer HPLC gereinigt. Man erhielt 76 mg der Titelverbnidung als gelbe Kristallmasse. A solution of 0.83 g of the ester from step 1 in 5 ml of DMSO was stirred at 110 ° C. for 16 hours. After concentrating the solution, the residue was purified by preparative HPLC. This gave 76 mg of the Titelverbnidung as a yellow crystal mass.
H-NMR (CDCIs): 7,83 (d); 7,71 -7,66 (m); 7,59 (t); 7,40 (d); 3,89 (s).  H-NMR (CDCIs): 7.83 (d); 7.71 -7.66 (m); 7.59 (t); 7,40 (d); 3.89 (s).
MS (M+H): m/z= 285  MS (M + H): m / z = 285
Tabelle I - Verbindungen der Formel I phys. DatenTable I - Compounds of Formula I Phys. Data
Nr. A E G Y X R R2 MS [m/z]; No. AEGYXRR 2 MS [m / z];
Fp. [°C] Mp [° C]
1-1 CH N N-C6H5 NH 0 OH ΟβΗδ 304 (M+H)+ 1-1 CH N NC 6 H 5 NH 0 OH ΟβΗδ 304 (M + H) +
I-2 S CH CH N-CH3 0 OCH3 3-F-CeH4 290 (M+H)+ I-2S CH CHN-CH 3 OCH 3 3-F-CeH 4 290 (M + H) +
I-3 S CH C-CH3 N-CH3 0 OCH3 3-F-CeH4 130°CI-3S CHC-CH 3 N-CH 3 OCH 3 3-F-CeH 4 130 ° C
I-4 S CH CH NH 0 OH ΟβΗδ 270°CI-4 S CH CH NH O OH ΟβΗδ 270 ° C
I-5 S CH CH NH 0 OH 2-CI-6-F-C6H3 260°C1-5 S CH CH NH O OH 2-CI-6-FC 6 H 3 260 ° C
I-6 CH N CH NH 0 OH ΟβΗδ 304 (M+H)+ I-6 CH N CH NH 0 OH ΟβΗδ 304 (M + H) +
I-7 S CH C-CH3 NH 0 OH 2-F-C6H4 318°CI-7S CHC-CH 3 NH 0 OH 2-FC 6 H 4 318 ° C
I-8 CH S CH N-CH3 0 OH 3-F-CeH4 26 3°C1-8 CH 2 CH 3 CH 3 CH 3 OH 3-F-CeH 4 26 3 ° C
I-9 CH S CH N-CH3 0 OCH3 3-F-CeH4 97°C-10 S CH C-CH3 NH 0 OH 3-F-CeH4 302°C 1-9 CH 2 CH 3 CH 2 -CH 3 O-F-CeH 4 97 ° C-10 S CH C-CH 3 NH 0 OH 3-F-CeH 4 302 ° C
2,4,6-CH3)3--1 1 CH N N-C6H5 NH 0 OH 346 (M+H)+ 2,4,6-CH 3 ) 3 - 1 CH 1 NC 6 H 5 NH 0 OH 346 (M + H) +
C6H2 phys. DatenC6H2 phys. data
Nr. A E G Y X R R2 MS [m/z]; No. AEGYXRR 2 MS [m / z];
Fp. [°C] Mp [° C]
1-12 N CH N-CHs NH 0 OH 2-CF3-C6H4 312 (M+H)+ 1-12 N CH N-CHs NH 0 OH 2-CF 3 -C 6 H 4 312 (M + H) +
1-13 CH N N-CHs NH 0 OH 2-CF3-C6H4 310 (M+H)+ 1-13 CH NN-CHs NH 0 OH 2-CF 3 -C 6 H 4 310 (M + H) +
1-14 N CH N-CHs NH 0 OCH2CHF2 2-CF3-C6H4 374 (M+H)+ 1-14 N CH N-CHs NH OCH 2 CHF 2 2-CF 3 -C 6 H 4 374 (M + H) +
1-15 CH N N-CHs 0 0 OH 2-CF3-C6H4 31 1 (M+H)+ 1-15 CH N-CHs 0 0 OH 2-CF3-C6H4 31 1 (M + H) +
Anwendungsbeispiele applications
Die herbizide Wirkung der Verbindungen der Formel I ließ sich durch Gewächshausversuche zeigen: The herbicidal activity of the compounds of the formula I was demonstrated by greenhouse experiments:
Als Kulturgefäße dienten Plastiktöpfe mit lehmigem Sand mit etwa 3,0% Humus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät. 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.
Bei Vorauflaufbehandlung wurden die in Wasser suspendierten oder emulgierten Wirkstoffe direkt nach Einsaat mittels fein verteilender Düsen aufgebracht. Die Gefäße wurden leicht beregnet, um Keimung und Wachstum zu fördern, und anschließend mit durchsichtigen Plastikhauben abgedeckt, bis die Pflanzen angewachsen waren. Diese Abdeckung bewirkt ein gleichmäßiges Keimen der Testpflanzen, sofern dies nicht durch die Wirkstoffe beeinträchtigt wurde.  In pre-emergence treatment, 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.
Zum Zweck der Nachauflaufbehandlung wurden die Testpflanzen je nach Wuchsform erst bis zu einer Wuchshöhe von 3 bis 15 cm angezogen und dann mit den in Wasser suspendierten oder emulgierten Wirkstoffen behandelt. Die Testpflanzen wurden dafür entweder direkt gesät und in den gleichen Gefäßen aufgezogen oder sie wurden erst als Keimpflanzen getrennt angezogen und einige Tage vor der Behandlung in die Versuchsgefäße verpflanzt.  For the postemergence treatment, the 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. For this purpose, 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.
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 - 25°C bzw. 20 - 35°C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet. 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.
Bewertet wurde nach einer Skala von 0 bis 100. Dabei bedeutet 100 kein Aufgang der Pflanzen bzw. völlige Zerstörung zumindest der oberirdischen Teile und 0 keine Schädigung oder normaler Wachstumsverlauf. Eine gute herbizide Aktivität ist bei Werten von wenigstens 70 und eine sehr gute herbizide Aktivität ist bei Werten von wenigstens 85 gegeben.  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.
Die in den Gewächshausversuchen verwendeten Pflanzen setzten sich aus folgenden Arten zusammen: Bayercode Lateinischer Name Deutscher Name Englischer NameThe plants used in the greenhouse experiments were composed of the following species: Bayer code Latin name German name English name
ABUTH Abutilon theophrasti chinesische Jute China jute ABUTH Abutilon theophrasti Chinese jute China jute
CHEAL Chenopodium album weisser Gänsefuss pigweed  CHEAL Chenopodium album white goosefoot pigweed
ECHCG Echinochloa crus-galli Hahnenkammhirse Cockspur  ECHCG Echinochloa crus-galli Cockscomb Cockspur
SETFA Setaria faberi grosse Borstenhirse giant foxtail SETFA Setaria faberi big bristle giant giant foxtail
SETIT Setaria italica Kolbenhirse Foxtail millet SETIT Setaria italica piston millet Foxtail millet
1 ) Der Wirkstoff I-2 zeigte bei 2,0 kg/ha im Nachauflauf gegen ABUTH eine sehr gute und der Wirkstoff I-9 bei 1 ,0 kg/ha eine gute herbizide Wirkung. 1) The active ingredient I-2 at 2.0 kg / ha postemergence against ABUTH a very good and the active ingredient I-9 at 1, 0 kg / ha a good herbicidal action.
2) Der Wirkstoff I-3 zeigte bei einer Aufwandmenge von 1 ,0 kg/ha im Nachauflauf gegen ECHCG eine sehr gute herbizide Wirkung.  2) The active ingredient I-3 showed at a rate of 1, 0 kg / ha postemergence against ECHCG a very good herbicidal activity.
3) Der Wirkstoff 1-12 zeigte bei 1 ,0 kg/ha im Nachauflauf gegen CHEAL eine gute herbizide Wirkung.  3) The active ingredient 1-12 showed at 1, 0 kg / ha postemergence against CHEAL a good herbicidal activity.
4) Der Wirkstoff I-5 zeigte bei einer Aufwandmenge von 3,0 kg/ha im Nachauflauf gegen SETIT eine sehr gute herbizide Wirkung.  4) The active ingredient I-5 showed at a rate of 3.0 kg / ha postemergence against SETIT a very good herbicidal activity.
5) Die Wirkstoffe I-4, bzw. I-8 zeigten bei 3,0 kg/ha im Nachauflauf gegen SETFA eine sehr gute herbizide Wirkung.  5) The active ingredients I-4, and I-8 showed at 3.0 kg / ha postemergence against SETFA a very good herbicidal activity.

Claims

Patentansprüche: claims:
1 . Verwendung von heteroaromatischen Verbindungen der Formel I
Figure imgf000044_0001
1 . Use of heteroaromatic compounds of the formula I
Figure imgf000044_0001
worin die Variablen folgende Bedeutung haben  wherein the variables have the following meaning
R1 0-RA, S(0)n-RA, 0-S(0)n-RA oder NR'R"; R 1 0-R A, S (0) n -R A, 0-S (0) n -R A or NR'R ";
RA Wasserstoff, Ci-C4-Alkyl, Z-C3-C6-Cycloalkyl, Ci-C4-Haloalkyl, C2-C6- Alkenyl, Z-C3-C6-Cycloalkenyl, C2-C6-Alkinyl, Z-(Tri-Ci-C4-alkyl)silyl, Z-C(=0)-Ra, Z-NR'-C(0)-NRiRii, Z-P(=0)(Ra)2, NR'R", über C oder N gebundener 3- bis 7-gliedriger monocyclischer oder 9- oder 10- gliedriger bicyclischer gesättigter, ungesättigter oder aromatischer Heterocyclus, enthaltend 1 , 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S, der teilweise oder vollständig durch Gruppen Ra und/oder Rb substituiert sein kann, 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, ZC (= O) -R a , Z-NR'-C (O) -NR i R ii , ZP (= O) (R a ) 2 , NR 'R', C or N bonded 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, the partial or can be completely substituted by groups R a and / or R b ,
Ra Wasserstoff, OH, Ci-C8-Alkyl, Ci-C4-Haloalkyl, Z-Cs-Ce-Cyclo- alkyl, C2-C8-Alkenyl, Z-C5-C6-Cycloalkenyl, C2-C8-Alkinyl, Z-Ci- C6-Alkoxy, Z-Ci-C4-Haloalkoxy, Z-C3-C8-Alkenyloxy, R a is hydrogen, OH, Ci-C 8 alkyl, Ci-C4-haloalkyl, Cs-Z-Ce-cyclo- alkyl, C 2 -C 8 alkenyl, ZC 5 -C 6 cycloalkenyl, C 2 -C 8- alkynyl, Z-Ci- C6-alkoxy, Z-C 1 -C 4 -haloalkoxy, ZC 3 -C 8 -alkenyloxy,
Z-Cs-Cs-Alkinyloxy, NR'R", Ci-C6-Alkylsulfonyl, Z-(Tri-Ci-C4- alkyl)silyl, Z-Phenyl, Z-Phenoxy, Z-Phenylamino und 5- oder 6- gliedriger monocyclischer oder 9- oder 10-glied riger bicyclischerZ is-Cs-Cs-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
Heterocyclus, enthaltend 1 , 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S, wobei die cyclischen Gruppen unsubsti- tuiert oder durch 1 , 2, 3 oder 4 Gruppen Rb substituiert sind, bedeutet; 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 , means;
R',R" unabhängig voneinander Wasserstoff, Ci-C8-Alkyl, Ci-C4-Halo- alkyl, C3-C8-Alkenyl, C3-C8-Alkinyl, Z-C3-C6-Cycloalkyl, Z-Ci-C8- Alkoxy, Z-Ci-C8-Haloalkoxy, Z-C(=0)-Ra, Z-Phenyl, über Z gebundener 3- bis 7-gliedriger monocyclischer oder 9- oder 10- gliedriger bicyclischer gesättigter, ungesättigter oder aroma- tischer Heterocyclus, enthaltend 1 , 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S; 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' und R" können auch gemeinsam mit dem N-Atom, an das sie gebunden sind, einen 5- oder 6-gliedrigen monocyclischen oder 9- oder 10-gliedrigen bicyclischer Heterocyclus bilden, enthal- tend 1 , 2, 3 oder 4 Heteroatome ausgewählt aus O, N und 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 eine kovalente Bindung oder Ci-C4-Alkylen; Z is a covalent bond or C 1 -C 4 -alkylene;
n 0, 1 oder 2;  n is 0, 1 or 2;
R2 Phenyl, Naphthyl oder und 5- oder 6-gliedriger monocyclischer oder 9- oder 10-gliedriger bicyclischer aromatischer Heterocyclus, enthaltend 1 , 2, 3 o- der 4 Heteroatome ausgewählt aus O, N und S, wobei die cyclischen Gruppen unsubstituiert oder durch 1 , 2, 3 oder 4 Gruppen Rb substituiert sind, bedeutet; R 2 is phenyl, naphthyl or and 5- or 6-membered monocyclic or 9- or 10-membered bicyclic aromatic heterocycle containing 1, 2, 3 o- the 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 ;
Rb unabhängig voneinander Z-CN, Z-OH, Z-NO2, Z-Halogen, Ci-Cs-Al- kyl, Ci-C4-Haloalkyl, C2-C8-Alkenyl, C2-C8-Alkinyl, Z-Ci-C8-Alkoxy,R b is independently Z-CN, Z-OH, Z-NO 2 , Z-halogen, C 1 -C 8 -alkyl, C 1 -C 4 -haloalkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl , Z-C 1 -C 8 -alkoxy,
Z-Ci-Cs-Haloalkoxy, Z-C3-Cio-Cycloalkyl, 0-Z-C3-Cio-Cycloalkyl, Z-C(=0)-Ra, NR'R'', Z-(Tri-Ci-C4-alkyl)silyl, Z-Phenyl und S(0)nRbb, wobei Rbb Ci-C8-Alkyl und d-Ce-Haloalkyl bedeutet und Z-Ci-Cs-haloalkoxy, ZC 3 -Cio-cycloalkyl, 0-ZC 3 -Cio-cycloalkyl, ZC (= O) -R a , NR'R '', Z- (tri-Ci-C 4 -alkyl ) silyl, Z-phenyl and S (O) n R bb , wherein R bb is Ci-C 8 -alkyl and d-Ce-haloalkyl and
n für 0, 1 oder 2 steht;  n is 0, 1 or 2;
Rb kann auch gemeinsam mit der an das benachbarte C-Atom gebundeneR b can also be used together with the bound to the adjacent carbon atom
Gruppe Rb einen fünf- oder sechsgliedrigen gesättigten, teilweise oder vollständig ungesättigten Ring bilden, der neben Kohlenstoff- 1 , 2 oder 3 Heteroatome ausgewählt aus O, N und S enthalten kann; Group R b form a five- or six-membered saturated, partially or completely unsaturated ring which, in addition to carbon, may contain 1, 2 or 3 heteroatoms selected from O, N and S;
X, Y O, S oder N-R3; X, YO, S or NR 3;
R3 Wasserstoff, Ci-C6-Alkyl, Ci-C4-Haloalkyl, C2-C6-Alkenyl, C3-C6-Alki- nyl, Z-Cs-C-io-Cycloalkyl, Ci-C6-Alkoxy-Ci-C6-alkyl, Ci-C6-Cyanoalkyl, Z-Phenyl, Z-C(=0)-Ra2 und Tri-Ci-C4-alkylsilyl; R 3 is hydrogen, Ci-C 6 alkyl, Ci-C 4 haloalkyl, C 2 -C 6 alkenyl, C 3 -C 6 -Alki- nyl, Z-Cs-C-io-cycloalkyl, Ci-C 6 alkoxy-Ci-C 6 alkyl, Ci-C 6 cyanoalkyl, phenyl-Z, Z is C (= 0) -R a2 and tri-Ci-C4-alkylsilyl;
Ra2 Ci-C6-Alkyl, Ci-C4-Haloalkyl, Z-Ci-C6-Alkoxy, Z-Ci-C4-Haloalk- oxy und NR'R"; 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 ";
A,E,G O, N, S und C-Rc, wobei mindestens eine Gruppe davon nicht C-Rc bedeutet und ein N durch Rc substituiert ist, A, E, GO, N, S and CR c , wherein at least one group thereof is not CR c and one N is substituted by R c ,
mit der Maßgabe, dass E nicht für O oder S steht, wenn mindestens eine Gruppe aus A und G für O oder S steht,  with the proviso that E is not O or S if at least one of A and G is O or S,
Rc Wasserstoff oder eine der bei Rb genannten Gruppen; R c is hydrogen or one of the groups mentioned for R b ;
wobei in Gruppen RA, R3 und deren Untersubstituenten die Kohlenstoffketten und/oder die cyclischen Gruppen teilweise oder vollständig durch Gruppen Rb substituiert sein können, in 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 ,
sowie deren N-Oxide und landwirtschaftlich geeignete Salze als Herbizide. 2. Verbindungen der Formel I gemäß Anspruch 1 , worin A für N steht.  and their N-oxides and agriculturally suitable salts as herbicides. 2. Compounds of formula I according to claim 1, wherein A is N.
3. Verbindungen der Formel I gemäß Anspruch 2, worin R1 für 0-RA, S(0)n-RA oder 0-S(0)n-RA steht. 4. Verbindungen der Formel I gemäß Anspruch 2 oder 3, worin Y für O steht. 3. Compounds of formula I according to claim 2, wherein R 1 is O -R A , S (0) n -R A or 0-S (0) n -R A. 4. Compounds of formula I according to claim 2 or 3, wherein Y is O.
5. Verbindungen der Formel I gemäß Anspruch 2 oder 3, worin Y für N-R3 steht. 5. Compounds of formula I according to claim 2 or 3, wherein Y is NR 3 .
6. Verbindungen der Formel I gemäß einem der Ansprüche 2 bis 5, worin R1 für 0-RA oder 0-S(0)n-RA steht. Verbindungen der Formel I gemäß einem der Ansprüche 2 bis 6, worin X für O steht. 6. Compounds of formula I according to any one of claims 2 to 5, wherein R 1 is 0-R A or 0-S (0) n -R A. Compounds of formula I according to any one of claims 2 to 6, wherein X is O.
Verbindungen der Formel I gemäß einem der Ansprüche 2 bis 7, welche der Formel I.A entsprechen,
Figure imgf000046_0001
Compounds of the formula I according to any one of claims 2 to 7, which correspond to the formula IA,
Figure imgf000046_0001
in der R5 und R6 für Gruppen Rb und m für Null oder eine ganze Zahl von eins bis vier stehen. in which R 5 and R 6 are groups R b and m are zero or an integer from one to four.
9. Verbindungen der Formel I gemäß einem der Ansprüche 2 bis 8, welche der Formel 1.1 entsprechen, 9. Compounds of the formula I according to any one of claims 2 to 8, which correspond to the formula 1.1,
Figure imgf000046_0002
Figure imgf000046_0002
in der Rc1 und Rc2 je einer Gruppe Rc entsprechen. in which R c1 and R c2 each correspond to a group R c .
10 Verbindungen der Formel I gemäß Anspruch 9, in der Rc1 für Wasserstoff und Rc2 für Methyl stehen. 1 1 Verbindungen der Formel I, gemäß einem der Ansprüche 2 bis 10, worin 10 compounds of the formula I according to claim 9, in which R c1 is hydrogen and R c2 is methyl. 1 1 Compounds of formula I, according to any one of claims 2 to 10, wherein
R1 OH, OCH3, OC(0)CH3, OC(0)CH2CH3, OC(0)CH(CH3)2, OC(0)C(CH3)3, OC(0)-c-C3H5, OC(0)-C6H5, OC(0)-CH2C6H5, OC(0)CH2CI, OC(0)-CF3, OC(0)-CH2OCH3, OC(0)-N(CH3)2 oder OC(0)-OCH2CH3; und R2 Phenyl, welches substituiert ist durch eine Gruppe ausgewählt aus 2-Br, 2-CI, 2,4-CI2, 2-CI-4-F, 2-CI-5-F, 2-CI-6-F, 2-CI-4-CF3, 2-CI-5-CF3, 2-CI-6- CF3, 2-CI-3,6-F2, 2-F, 2,4-F2, 2,5-F2, 2,6-F2, 2-F-4-CF3, 2-F-5-CF3, 2-F-6- CF3, 2,3,6-F3, 2-N02, 2-N02-4-F, 2-N02-5-F, 2-N02-6-F, 2-N02-4-CF3, 2-N02-5-CF3, 2-N02-6-CF3, 2-N02-3,6-F2, 2-CN, 2-CH3, 2-CH3-4-F, 2-CH3-R 1 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 (0) cC 3 H 5, OC (0) -C 6 H 5, OC (0) -CH 2 C 6 H 5, OC (0) CH 2 Cl, OC (0) -CF 3, OC (0) -CH 2 OCH 3 , OC (O) -N (CH 3 ) 2 or OC (O) -OCH 2 CH 3 ; and 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 -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-CH3-6-F, 2-CH3-4-CF3, 2-CH3-5-CF3, 2-CH3-6-CF3, 2-CH3-3,6-F2, 2-OCH3, 2-OCH3-4-F, 2-OCH3-5-F, 2-OCH3-6-F, 2-OCH3-4-CF3, 2-OCH3-5- CF3, 2-OCH3-6-CF3, 2-OCH3-3,6-F2, 2-CHF2, 2-CHF2-4-F, 2-CHF2-5-F, 2-CHF2-6-F, 2-CHF2-4-CF3, 2-CHF2-5-CF3, 2-CHF2-6-CF3, 2-CHF2-3,6-F2, 2-CF3, 2-CF3-4-F, 2-CF3-5-F, 2-CF3-6-F, 2-CF3-4-CF3, 2-CF3-5-CF3, 2-CF3-5-F, 2-CH 3 -6-F, 2-CH 3 -4-CF 3 , 2-CH 3 -5-CF 3 , 2-CH 3 -6-CF 3 , 2-CH 3 -3, 6-F 2 , 2-OCH 3 , 2-OCH 3 -4-F, 2-OCH 3 -5-F, 2-OCH 3 -6-F, 2-OCH 3 -4-CF 3 , 2-OCH 3 -5- CF 3 , 2-OCH 3 -6-CF 3 , 2-OCH 3 -3,6-F 2 , 2-CHF 2 , 2-CHF 2 -4-F, 2-CHF 2 -5- F, 2-CHF 2 -6-F, 2-CHF 2 -4-CF 3 , 2-CHF 2 -5-CF 3 , 2-CHF 2 -6-CF 3 , 2-CHF 2 -3,6- F 2 , 2-CF 3 , 2-CF 3 -4-F, 2-CF 3 -5-F, 2-CF 3 -6-F, 2-CF 3 -4-CF 3 , 2-CF 3 - 5-CF 3 , 2-CF 3 -
6- CF3, 2-CF3-3,6-F2, 2-OCHF2, 2-OCHF2-4-F, 2-OCHF2-5-F, 2-OCHF2-6-F, 2-OCHF2-4-CF3, 2-OCHF2-5-CF3, 2-OCHF2-6-CF3, 2-OCHF2-3,6-F2, 2-OCF3, 2-OCF3-4-F, 2-OCF3-5-F, 2-OCF3-6-F, 2-OCF3-4-CF3, 2-OCF3-5- CF3, 2-OCF3-6-CF3 oder 2-OCF3-3,6-F2 bedeuten. Mittel, enthaltend eine herbizid wirksame Menge mindestens einer Verbindung der Formel I oder eines landwirtschaftlich geeigneten Salzes davon nach einem der Ansprüche 1 bis 1 1 und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel. 6- CF 3 , 2-CF 3 -3,6-F 2 , 2-OCHF 2 , 2-OCHF 2 -4-F, 2-OCHF 2 -5-F, 2-OCHF 2 -6-F, 2 -OCHF 2 -4-CF 3 , 2-OCHF 2 -5-CF 3 , 2-OCHF 2 -6-CF 3 , 2-OCHF 2 -3,6-F 2 , 2-OCF 3 , 2-OCF 3 4-F, 2-OCF 3 -5-F, 2-OCF 3 -6-F, 2-OCF 3 -4-CF 3 , 2-OCF 3 -5-CF 3 , 2-OCF 3 -6- CF 3 or 2-OCF 3 -3,6-F 2 . An agent containing a herbicidally effective amount of at least one compound of the formula I or an agriculturally suitable salt thereof according to any one of claims 1 to 11 and auxiliaries customary for the formulation of crop protection agents.
13. Mittel gemäß Anspruch 12, enthaltend mindestens einen weiteren Wirkstoff. 13. Composition according to claim 12, containing at least one further active ingredient.
14. Mittel gemäß Anspruch 12 oder 13, enthaltend zwei weitere Wirkstoffe aus der Gruppe der Herbizide und/oder Safener. 14. Composition according to claim 12 or 13, containing two further active compounds from the group of herbicides and / or safeners.
15. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, dass man eine herbizid wirksame Menge mindestens einer Verbindung der Formel I oder eines landwirtschaftlich brauchbaren Salzes davon nach einem der Ansprüche 1 bis 1 1 auf Pflanzen, deren Samen und/oder deren15. A method for controlling undesired plant growth, characterized in that comprising a herbicidally effective amount of at least one compound of formula I or an agriculturally useful salt thereof according to one of claims 1 to 1 1 on plants, their seeds and / or their
Lebensraum einwirken lässt. Habitat acts.
PCT/EP2010/066037 2009-10-28 2010-10-25 Use of heteroaromatic compounds as herbicides WO2011051212A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09174356.7 2009-10-28
EP09174356 2009-10-28

Publications (1)

Publication Number Publication Date
WO2011051212A1 true WO2011051212A1 (en) 2011-05-05

Family

ID=43303296

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2010/066037 WO2011051212A1 (en) 2009-10-28 2010-10-25 Use of heteroaromatic compounds as herbicides

Country Status (1)

Country Link
WO (1) WO2011051212A1 (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012028582A1 (en) * 2010-09-01 2012-03-08 Bayer Cropscience Ag Herbicidally active ketosultams and diketopyridines
US8440594B2 (en) 2010-03-23 2013-05-14 Basf Se Pyridothiazines having herbicidal action
WO2013144096A1 (en) * 2012-03-27 2013-10-03 Bayer Intellectual Property Gmbh Herbicidally and insecticidally active thiazolopyridinones
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 (en) * 2014-12-22 2016-06-30 Syngenta Participations Ag Thiazolopyridinones as herbicides
JP2018515469A (en) * 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 Herbicidal compounds
WO2022078403A1 (en) * 2020-10-15 2022-04-21 江苏先声药业有限公司 Substituted pyridone compound and application

Citations (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5630979A (en) * 1979-08-22 1981-03-28 Taiho Yakuhin Kogyo Kk Pyranoindolizine derivative and its preparation
EP0242236A1 (en) 1986-03-11 1987-10-21 Plant Genetic Systems N.V. Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
EP0257993A2 (en) 1986-08-26 1988-03-02 E.I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en) 1989-03-24 1990-10-17 Ciba-Geigy Ag Disease-resistant transgenic plants
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
WO1992000377A1 (en) 1990-06-25 1992-01-09 Monsanto Company Glyphosate tolerant plants
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
EP0588137A1 (en) * 1992-09-10 1994-03-23 Bayer Ag 3-Aryl-2-pyranone derivatives
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
WO1996026202A1 (en) 1995-02-21 1996-08-29 Degussa Aktiengesellschaft Process for producing thietanones
US5559024A (en) 1988-03-23 1996-09-24 Rhone-Poulenc Agrochimie Chimeric nitrilase-encoding gene for herbicidal resistance
WO1997001535A1 (en) * 1995-06-28 1997-01-16 Bayer Aktiengesellschaft 2,4,5-trisubstituted phenylketo-enols for use as pesticides and herbicides
WO1997036868A1 (en) * 1996-04-02 1997-10-09 Bayer Aktiengesellschaft Substituted phenyl keto enols as pesticides and herbicides
WO1997041116A1 (en) 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Benzene derivatives substituted by heterocycles and herbicides
WO1997041218A1 (en) 1996-04-29 1997-11-06 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
WO1997041117A1 (en) 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Novel benzene derivatives substituted by heterocycles and herbicides
WO1997041118A1 (en) 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Benzene derivatives substituted by heterocycles and herbicides
WO1998002526A1 (en) 1996-07-17 1998-01-22 Michigan State University Imidazolinone herbicide resistant sugar beet plants
WO1998002527A1 (en) 1996-07-17 1998-01-22 Michigan State University Imidazolinone herbicide resistant sugar beet plants
WO2000008026A2 (en) * 1998-08-06 2000-02-17 E.I. Du Pont De Nemours And Company Fungicidal fused bicyclic heterocycles
WO2000021946A1 (en) * 1998-10-09 2000-04-20 Bayer Aktiengesellschaft 3-phenyl-pyrones
WO2000026390A2 (en) 1998-10-29 2000-05-11 American Cyanamid Company Genes and vectors for conferring herbicide resistance in plants
US6222100B1 (en) 1984-03-06 2001-04-24 Mgi Pharma, Inc. Herbicide resistance in plants
WO2001083459A2 (en) 2000-05-04 2001-11-08 Basf Aktiengesellschaft Uracil substituted phenyl sulfamoyl carboxamides
WO2001082685A1 (en) 2000-04-28 2001-11-08 Basf Aktiengesellschaft Use of the maize x112 mutant ahas 2 gene and imidazolinone herbicides for selection of transgenic monocots, maize, rice and wheat plants resistant to the imidazolinone herbicides
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2002018383A2 (en) * 2000-09-01 2002-03-07 Chiron Corporation Aza heterocyclic derivatives and their therapeutic use
WO2003014356A1 (en) 2001-08-09 2003-02-20 University Of Saskatchewan Wheat plants having increased resistance to imidazolinone herbicides
WO2003013225A2 (en) 2001-08-09 2003-02-20 Northwest Plant Breeding Company Wheat plants having increased resistance to imidazolinone herbicides
WO2003014357A1 (en) 2001-08-09 2003-02-20 University Of Saskatchewan Wheat plants having increased resistance to imidazolinone herbicides
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2003066630A2 (en) * 2002-02-07 2003-08-14 Amgen Inc. Quinolinone derivatives for treating cell proliferation related disorders
WO2004016073A2 (en) 2002-07-10 2004-02-26 The Department Of Agriculture, Western Australia Wheat plants having increased resistance to imidazolinone herbicides
WO2004106529A2 (en) 2003-05-28 2004-12-09 Basf Aktiengesellschaft Wheat plants having increased tolerance to imidazolinone herbicides
WO2005020673A1 (en) 2003-08-29 2005-03-10 Instituto Nacional De Technologia Agropecuaria Rice plants having increased tolerance to imidazolinone herbicides
WO2008009908A1 (en) 2006-07-20 2008-01-24 Syngenta Limited Pyrido [2, 3-b] pyrazine derivatives useful as herbicidal compounds
WO2008071918A1 (en) 2006-12-12 2008-06-19 Syngenta Limited Pyrido-pyrazine derivatives useful as herbicidal compounds
WO2008074991A1 (en) 2006-12-21 2008-06-26 Syngenta Limited Novel herbicides

Patent Citations (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5630979A (en) * 1979-08-22 1981-03-28 Taiho Yakuhin Kogyo Kk Pyranoindolizine derivative and its preparation
US6222100B1 (en) 1984-03-06 2001-04-24 Mgi Pharma, Inc. Herbicide resistance in plants
EP0451878A1 (en) 1985-01-18 1991-10-16 Plant Genetic Systems, N.V. Modifying plants by genetic engineering to combat or control insects
EP0242236A1 (en) 1986-03-11 1987-10-21 Plant Genetic Systems N.V. Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
EP0242246A1 (en) 1986-03-11 1987-10-21 Plant Genetic Systems N.V. Plant cells resistant to glutamine synthetase inhibitors, made by genetic engineering
EP0257993A2 (en) 1986-08-26 1988-03-02 E.I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5013659A (en) 1987-07-27 1991-05-07 E. I. Du Pont De Nemours And Company Nucleic acid fragment encoding herbicide resistant plant acetolactate synthase
US5559024A (en) 1988-03-23 1996-09-24 Rhone-Poulenc Agrochimie Chimeric nitrilase-encoding gene for herbicidal resistance
EP0374753A2 (en) 1988-12-19 1990-06-27 American Cyanamid Company Insecticidal toxines, genes coding therefor, antibodies binding them, transgenic plant cells and plants expressing these toxines
EP0392225A2 (en) 1989-03-24 1990-10-17 Ciba-Geigy Ag Disease-resistant transgenic plants
EP0427529A1 (en) 1989-11-07 1991-05-15 Pioneer Hi-Bred International, Inc. Larvicidal lectins and plant insect resistance based thereon
WO1992000377A1 (en) 1990-06-25 1992-01-09 Monsanto Company Glyphosate tolerant plants
WO1993007278A1 (en) 1991-10-04 1993-04-15 Ciba-Geigy Ag Synthetic dna sequence having enhanced insecticidal activity in maize
EP0588137A1 (en) * 1992-09-10 1994-03-23 Bayer Ag 3-Aryl-2-pyranone derivatives
WO1995034656A1 (en) 1994-06-10 1995-12-21 Ciba-Geigy Ag Novel bacillus thuringiensis genes coding toxins active against lepidopteran pests
WO1996026202A1 (en) 1995-02-21 1996-08-29 Degussa Aktiengesellschaft Process for producing thietanones
WO1997001535A1 (en) * 1995-06-28 1997-01-16 Bayer Aktiengesellschaft 2,4,5-trisubstituted phenylketo-enols for use as pesticides and herbicides
WO1997036868A1 (en) * 1996-04-02 1997-10-09 Bayer Aktiengesellschaft Substituted phenyl keto enols as pesticides and herbicides
WO1997041118A1 (en) 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Benzene derivatives substituted by heterocycles and herbicides
WO1997041117A1 (en) 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Novel benzene derivatives substituted by heterocycles and herbicides
WO1997041116A1 (en) 1996-04-26 1997-11-06 Nippon Soda Co., Ltd. Benzene derivatives substituted by heterocycles and herbicides
WO1997041218A1 (en) 1996-04-29 1997-11-06 Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College Herbicide resistant rice
WO1998002526A1 (en) 1996-07-17 1998-01-22 Michigan State University Imidazolinone herbicide resistant sugar beet plants
WO1998002527A1 (en) 1996-07-17 1998-01-22 Michigan State University Imidazolinone herbicide resistant sugar beet plants
WO2000008026A2 (en) * 1998-08-06 2000-02-17 E.I. Du Pont De Nemours And Company Fungicidal fused bicyclic heterocycles
WO2000021946A1 (en) * 1998-10-09 2000-04-20 Bayer Aktiengesellschaft 3-phenyl-pyrones
WO2000026390A2 (en) 1998-10-29 2000-05-11 American Cyanamid Company Genes and vectors for conferring herbicide resistance in plants
WO2001082685A1 (en) 2000-04-28 2001-11-08 Basf Aktiengesellschaft Use of the maize x112 mutant ahas 2 gene and imidazolinone herbicides for selection of transgenic monocots, maize, rice and wheat plants resistant to the imidazolinone herbicides
WO2001083459A2 (en) 2000-05-04 2001-11-08 Basf Aktiengesellschaft Uracil substituted phenyl sulfamoyl carboxamides
WO2002015701A2 (en) 2000-08-25 2002-02-28 Syngenta Participations Ag Bacillus thuringiensis crystal protein hybrids
WO2002018383A2 (en) * 2000-09-01 2002-03-07 Chiron Corporation Aza heterocyclic derivatives and their therapeutic use
WO2003014356A1 (en) 2001-08-09 2003-02-20 University Of Saskatchewan Wheat plants having increased resistance to imidazolinone herbicides
WO2003013225A2 (en) 2001-08-09 2003-02-20 Northwest Plant Breeding Company Wheat plants having increased resistance to imidazolinone herbicides
WO2003014357A1 (en) 2001-08-09 2003-02-20 University Of Saskatchewan Wheat plants having increased resistance to imidazolinone herbicides
WO2003018810A2 (en) 2001-08-31 2003-03-06 Syngenta Participations Ag Modified cry3a toxins and nucleic acid sequences coding therefor
WO2003052073A2 (en) 2001-12-17 2003-06-26 Syngenta Participations Ag Novel corn event
WO2003066630A2 (en) * 2002-02-07 2003-08-14 Amgen Inc. Quinolinone derivatives for treating cell proliferation related disorders
WO2004016073A2 (en) 2002-07-10 2004-02-26 The Department Of Agriculture, Western Australia Wheat plants having increased resistance to imidazolinone herbicides
WO2004106529A2 (en) 2003-05-28 2004-12-09 Basf Aktiengesellschaft Wheat plants having increased tolerance to imidazolinone herbicides
WO2005020673A1 (en) 2003-08-29 2005-03-10 Instituto Nacional De Technologia Agropecuaria Rice plants having increased tolerance to imidazolinone herbicides
WO2008009908A1 (en) 2006-07-20 2008-01-24 Syngenta Limited Pyrido [2, 3-b] pyrazine derivatives useful as herbicidal compounds
WO2008071918A1 (en) 2006-12-12 2008-06-19 Syngenta Limited Pyrido-pyrazine derivatives useful as herbicidal compounds
WO2008074991A1 (en) 2006-12-21 2008-06-26 Syngenta Limited Novel herbicides

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
B. HOCK; C. FEDTKE; R. R. SCHMIDT: "Herbizide", 1995, GEORG THIEME VERLAG
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 1981, "Pyranoindolizine derivatives", XP002615500, retrieved from STN Database accession no. 1981:515506 *
EGYPTIAN JOURNAL OF CHEMISTRY, vol. 37, no. 3, 1994, pages 273 - 282
J. AGRIC. AND FOOD CHEM., vol. 42, no. 4, 1994, pages 1019 - 1025
SILVERMAN; RICHARD B., J. AM. CHEM. SOC., vol. 103, no. 13, 1981, pages 3910
W. KRÄMER ET AL.: "Modern Crop Protection Compounds", vol. 1, 2007, WILEY VCH

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 (en) * 2010-09-01 2013-07-03 拜耳知识产权有限责任公司 Herbicidally active ketosultams and diketopyridines
JP2013536818A (en) * 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 Ketosultams and diketopyridines with herbicidal activity
WO2012028582A1 (en) * 2010-09-01 2012-03-08 Bayer Cropscience Ag Herbicidally active ketosultams and diketopyridines
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 (en) * 2012-03-27 2015-02-11 拜耳知识产权有限责任公司 Herbicidally and insecticidally active thiazolopyridinones
WO2013144096A1 (en) * 2012-03-27 2013-10-03 Bayer Intellectual Property Gmbh Herbicidally and insecticidally active thiazolopyridinones
JP2015512906A (en) * 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 Thiazolopyridinones with herbicidal and insecticidal activity
US9307767B2 (en) 2012-03-27 2016-04-12 Bayer Intellectual Property Gmbh Herbicidally and insecticidally active thiazolopyridinones
CN104350059B (en) * 2012-03-27 2016-12-07 拜耳知识产权有限责任公司 There is the thiazolopyridin ketone of weeding and insecticidal activity
GB2525270A (en) * 2013-12-05 2015-10-21 Syngenta Ltd Herbicidal compounds
WO2016102253A1 (en) * 2014-12-22 2016-06-30 Syngenta Participations Ag Thiazolopyridinones as herbicides
CN107108654A (en) * 2014-12-22 2017-08-29 先正达参股股份有限公司 It is used as the thiazolopyridin ketone of herbicide
JP2018515469A (en) * 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 Herbicidal compounds
US10512269B2 (en) 2015-04-30 2019-12-24 Syngenta Participations Ag Herbicidal compounds
CN111484509A (en) * 2015-04-30 2020-08-04 先正达参股股份有限公司 Herbicidal compounds
WO2022078403A1 (en) * 2020-10-15 2022-04-21 江苏先声药业有限公司 Substituted pyridone compound and application

Similar Documents

Publication Publication Date Title
US8658569B2 (en) Substituted quinolinones having herbicidal action
EP2350074B1 (en) Substituted pyridines having a herbicidal effect
WO2011051212A1 (en) Use of heteroaromatic compounds as herbicides
DE102010042866A1 (en) New thioamide compounds, useful for controlling undesirable plant growth or weeds in cultural plants e.g. Arachis hypogaea, Allium cepa, Elaeis guineensis and Gossypium herbaceum
WO2010069802A1 (en) Heterocyclic diketone derivatives with herbicidal action
WO2011003776A2 (en) Substituted cyanobutyrates having a herbicidal effect
WO2011003775A2 (en) Substituted cyanobutyrates having a herbicidal effect
CN108473444A (en) Benzamide compounds and its purposes as herbicide
KR20130051932A (en) Pyridothiazines having herbicidal action
JP2013522335A (en) Pyrazinothiazine with herbicidal activity
WO2011042378A1 (en) Substituted cyanobutyrates having herbicidal effect
WO2010139657A1 (en) Substituted pyrazine (thio)pyrans with a herbicidal action
EP2655381A1 (en) Substituted pyridines having herbicidal activity
WO2011057989A1 (en) Heterocyclic compounds having herbicidal action
WO2011058036A1 (en) Tricyclic compounds having herbicidal action
JP2013522340A (en) Substituted pyridines with herbicidal action
WO2011067184A1 (en) 3- (4, 5 -dihydroisoxazol- 5 -yl) benzoylpyrazole compounds and mixtures thereof with safeners
DE102010042867A1 (en) Use of heterocyclic compounds as herbicides and for controlling undesirable plants in culture of useful plants e.g. wheat, barley, rye, oats, millet and rice
DE102011080568A1 (en) New substituted cyanobutyrate compounds useful for combating weeds in culture plants e.g. cotton, rice, maize or wheat

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10768254

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10768254

Country of ref document: EP

Kind code of ref document: A1