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WO1998007720A1 - Arylpyridine substituee en 2 utilisee comme herbicide - Google Patents

Arylpyridine substituee en 2 utilisee comme herbicide Download PDF

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Publication number
WO1998007720A1
WO1998007720A1 PCT/EP1997/004421 EP9704421W WO9807720A1 WO 1998007720 A1 WO1998007720 A1 WO 1998007720A1 EP 9704421 W EP9704421 W EP 9704421W WO 9807720 A1 WO9807720 A1 WO 9807720A1
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alkyl
alkoxy
butyl
substituted
cooch
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German (de)
English (en)
Inventor
Peter Schäfer
Gerhard Hamprecht
Markus Menges
Olaf Menke
Michael Rack
Cyrill Zagar
Helmut Walter
Karl-Otto Westphalen
Ulf Misslitz
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to new substituted 2-aryl pyridines of the formula I.
  • n zero or 1;
  • R 1 mercapto, hydroxysulfonyl, chlorosulfonyl, aminosulfonyl, C ⁇ -C 6 -alkylthio, C ⁇ -C 6 -alkylsulfinyl, Ci -C 6 -alkylsulfonyl, Ci -C 6 -alkylaminosulfonyl or di- (Ci-C ⁇ -alkyl) aminosulfonyl, -
  • R 2 , R 3 independently of one another are hydrogen or halogen
  • R 4 is hydrogen, Cx-Ce-alkyl, Ci -C 6 -haloalkyl, cyano-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxy, CI-C ⁇ -alkoxy-Ci-C ⁇ -alkyl, Ci -C -halogen - Alkoxy -CC-alkyl, -CC 6 -alkylthio -CC 6 -alkyl, -C-C 6 -alkyl-sulfinyl -CC-C 6 - alkyl, -C-C 6 -alkylsulfonyl -C ⁇ -C 6 -alkyl, -C-C 4 -alkoxy-C ⁇ -C 4 -alkoxy-C ⁇ -C 4 -alkyl, (Cj .
  • X is oxygen, sulfur, -NH-, -N (CH 3 ) - or methylene; Y is a chemical bond, carbonyl or C (R 5 , R 6 ), where
  • R 5 , R 6 independently of one another for hydrogen, nitro
  • the invention also relates to the use of the compounds I as herbicides or for
  • WO 95/02590 describes a large number of herbicidally active 2-phenylpyridines.
  • the present invention was based on new herbicidally active compounds as a task with which undesired plants can be controlled more effectively than before.
  • the task also extends to the provision of new desiccant / defoliant connections.
  • substituted 2-arylpyridines of the formula I defined at the outset with herbicidal activity and new intermediates X, XVI, XXXIa, XXXIb, XXXIIa, XXXIIc, XXVIa, XXXVIb, XXXVIIa and XXXVIIb for their preparation were found.
  • herbicidal compositions have been found which contain the compounds I and have a very good herbicidal action.
  • processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the compounds I are also suitable for the desiccation / defoliation of parts of plants, for which crop plants such as cotton, potato, rapeseed, sunflower, soybean or field beans, in particular cotton and potato, are suitable.
  • crops plants such as cotton, potato, rapeseed, sunflower, soybean or field beans, in particular cotton and potato
  • agents for the desiccation and / or defoliation of plants, methods for producing these agents and methods for the desiccation and / or defoliation of plants with the compounds I have been found.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as mixtures of enantiomers or diastereomers.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • Particularly suitable salts are those of the alkali metals, preferably sodium and potassium salts, of the alkaline earth metals, preferably calcium and magnesium salts, those of the transition metals, preferably zinc and iron salts, and also ammonium salts in which the ammonium ion, if desired, has one to four C 1 -C 4 -Alkyl-, hydroxy-C-C-alkyl substituents and / or can carry a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylamium, triethylbenzylammonium and trimethyl (2-hydroxyethyl) ammonium salts , furthermore phosphonium salts, sulfonium salts such as preferably tri- (C 1 -C 4 -alkyl) sulfonium salts, and sulfoxonium salts such as preferably tri- (C ⁇ -C-al
  • the organic molecule parts mentioned for the substituents R 1 and R 4 to R 6 or as residues on a phenyl ring represent collective terms for individual enumeration of the individual groups - members.
  • Halogenated substituents preferably carry one to five identical or different halogen atoms.
  • Halogen is in each case fluorine, chlorine, bromine or iodine, in particular fluorine or chlorine.
  • C 1 -C 4 alkyl fr CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, 1-methylpropyl, 2-methylpropyl or C (CH) 3 , in particular for CH 3 , C 2 H 5 , CH (CH 3 ) 2 or C (CH 3 ) 3 ;
  • -C 1 -C 6 alkyl for: for example CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, 1-methylpropyl, 2-methylpropyl, C (CH 3 ) 3 , n- Pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2- Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-diethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl,
  • -C-C 4 haloalkyl for: a C ⁇ -C 4 alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for CH 2 F, CHF 2 , CF 3 , CH 2 C1, CH (C1) 2 , C (C1) 3 , CHFC1, CF (C1) 2 , CF 2 C1, CF 2 Br,
  • Ci-C ö haloalkyl for: a Ci-Ce alkyl radical as mentioned above, which is partially or completely replaced by fluorine, chlorine,
  • Bromine and / or iodine is substituted, for example for CH 2 F, CHF 2 , CF 3 , CH 2 C1, CH (C1) 2 , C (C1) 3 , CHFC1, CF (C1) 2 , CF 2 C1, CF.
  • Cyano-C ⁇ -C 6 alkyl for: for example CH 2 CN, 1-cyanoethyl, 2-cyanoethyl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyanoprop-l-yl, 1-cyanobut -l-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyano-but-l-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, 3-cyanobut -2-yl, 4-cyanobut-2-yl, 1- (CH 2 CN) -eth-1-yl, 1- (CH 2 CN) -1- (CH 3 ) -eth- 1-yl, 1- (CH 2 CN) prop-1-yl or 2-cyano-hex-6-yl, in particular for CH 2 CN or 2-cyanoethyl;
  • C 3 -C 7 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, in particular for cyclopentyl or cyclohexyl;
  • cycloalkyl-C 6 -C 6 alkyl for: cyclopropyl -CH 2 , 1-cyclopropyl-ethyl, 2-cyclopropyl-ethyl, 1-cyclopropyl-prop-l-yl, 2-cyclopropyl-prop -l-yl, 3-cyclopropyl-prop-l-yl, 1-cyclopropyl-but-1-yl, 2-cyclopropyl-but-l-yl, 3-cyclopropyl-but-l-yl, 4-cyclopropyl -but-1-yl, 1-cyclopropyl-but-2-yl, 2-cyclopropyl-but-2-yl, 3-cyclopropyl-but-2-yl, 4-cyclopropyl-but-2-yl, 1 - (Cyclopropyl -CH 2 ) eth-l-yl, 1- (cyclopropyl -CH 2 ) -1- (CH 3
  • (-C-C 6 alkyl) carbonyl for: for example CO-CH 3 , CO-C 2 H 5 , CO-CH 2 -C 2 H 5 , CO-CH (CH 3 ) 2 . n-butylcarbonyl, CO-CH (CH 3 ) -C 2 H 5 , 2-methylpropylcarbonyl, CO-C (CH 3 ) 3 , n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1, 1-dimethylpropylcarbonyl, 1, 2-dimethylpropylcarbonyl, 2, 2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1, 1- Dimethylbutyl - carbonyl, 1, 2-di
  • -C-C 6 alkoxy for: for example 0CH 3 , OC 2 H 5 , n-propoxy, OCH (CH 3 ) 2 , n-butoxy, OCH (CH 3 ) -C 2 H 5 , 0CH 2 -CH (CH 3 ) 2 , OC (CH 3 ) 3 , n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethyl- propoxy, n-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-trimethylprop oxy, 1-ethyl-l-methylpropoxy or l-ethyl-2-methylpropoxy, in particular 0CH 3 , OC 2 H 5 , 0CH (CH 3 ) 2 or OC (CH 3 ) 3 ;
  • C 1 -C 6 -alkoxy-C 6 -C 6 -alkyl for: C 1 -C 6 -alkoxy as mentioned above substituted C 1 -C 6 -alkyl, for example for
  • CH 2 OCH 3 CH 2 OC 2 H 5 , CH 2 OCH 2 -C 2 H 5 , CH 2 OCH (CH 3 ) 2 , CH 2 OCH 2 CH 2 -C 2 H 5 , (l-methylpropoxy) methyl, (2-Methylpropoxy) methyl, CH 2 OC (CH) 3 , CH 2 0 (CH 2 ) 3 -C 2 H 5 , CH 2 0 (CH 2 ) 4 -C 2 H 5 , CH (CH 3 ) OCH 3 , CH (CH 3 ) OC 2 H 5 , CH 2 CH 2 OCH 3 , CH 2 CH 2 0C 2 H 5 , CH 2 CH 2 0CH 2 -C 2 H5, CH 2 CH 2 0CH (CH 3 ) 2 , CH 2 CH 2 OCH 2 CH 2 -C 2 H 5 , 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl, CH 2 CH 2 OC (CH 3 ) 3 , 2-
  • C 1 -C 4 -alkoxy-C 4 -alkoxy-C 4 -C 4 -alkyl for: by 0CH 3 , OC 2 H 5 , n-propoxy, OCH (CH 3 ) 2 , n-butoxy, 1-methylpropoxy, 2-methyl-propoxy or OC (CH 3 ) 3 , preferably OCH 3 , substituted C 1 -C 4 -alkoxy-C 4 -C 4 -alkyl, that is, for example, for CH 2 OCH OCH 3 , CH 2 OCH 2 OC 2 H 5 , CH 2 OCH 2 OCH (CH 3 ) 2 or CH 2 OCH 2 OC (CH 3 ) 3 ;
  • Ci -C-C 4 haloalkoxy -CC 4 - alkyl for: by Ci -C 4 haloalkoxy such as OCH 2 F, OCHF 2 , 0CF 3 , 0CH 2 C1, 0CH (C1) 2 , 0C (C1) 3 , 0CHFC1 , 0CF (C1) 2 , 0CF 2 C1, 0CF 2 Br, 1-fluoroethoxy, 2-fluoroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoro ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2, 2, 2-trichloroethoxy, OC 2 F 5 , 2-fluoropropoxy, 3-fluoropropoxy , 2-chloropropoxy, 3-chloropropoxy,
  • C 3 -C Cycloalkyloxy -CC 6 alkyl for: by C 3 -C cycloalkyloxy such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy and cycloheptyloxy, preferably cyclopropyloxy, substituted -CC 6 alkyl, for example for cyclopropyl -OCH 2 , 1-cyclopropyloxy-ethyl, 2-cyclopropyloxy-ethyl, 1-cyclopropyloxy-prop-l-yl, 2-cyclopropyloxy-prop-1-yl, 3-cyclopropyloxy-prop-l-yl, 1- Cyclopropyloxy-but-1-yl, 2-cyclopropyloxy-but-l-yl, 3-cyclopropyloxy-but-1-yl, 4-cyclopropyloxy-but-l-yl, 1-cyclopropyloxy-but-2- y
  • (C ⁇ -C 4 -alkoxy) carbonyl for: COOCH 3 , COOC 2 H 5 , n-propoxycarbonyl, OCH (CH 3 ) 2 , n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or OC (CH 3 ) 3 , in particular for C00CH 3 , COOC 2 H 5 or COOC (CH 3 ) 3 ;
  • (Ci-C ö -alkoxy) carbonyl for: C00CH 3 , COOC 2 H 5 , n-propoxycarbonyl, OCH (CH 3 ), n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl, OC (CH 3 ) 3 , n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethyl-propoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl, 1,2-diethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2, 3-
  • (C 1 -C 4 alkoxy) carbonyl -C ⁇ -C 4 alkyl by (C 1 -C 4 alkoxy) - carbonyl - as mentioned above - substituted C 1 -C 4 alkyl, eg CH 2 COOCH 3 , CH 2 COOC 2 H 5 , CH 2 COOCH 2 -C 2 H 5 , CH 2 COOCH (CH 3 ) 2 , CH 2 COOCH 2 CH 2 -C 2 H 5 , (1-methylpropoxycarbonyl) - ethyl, ( 2-Methylpropoxy-carbonyDmethyl, CH 2 COOC (CH 3 ) 3 , CH 2 COO (CH 2 ) 3 -C 2 H 5 , CH 2 COO (CH 2 ) 4 -C 2 H 5 , CH (CH 3 ) COOCH 3 , CH (CH 3 ) COOC 2 H 5 , CH 2 CH 2 COOCH 3 , CH 2 CH COOC 2 H 5 , CH CH COOCH 2 H
  • C ! -C 6 alkylthio for: e.g. SCH 3 , SC 2 H 5 , n-propylthio, SCH (CH 3 ) 2 , n-butylthio, SCH (CH 3 ) -CH 5 , SCH 2 -CH (CH 3 ) 2 , SC (CH 3 ) 3 , n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1, 1-dimethylpropylthio, 1, 2 -Dimethylpropylthio, l-methyl-pentylthio, 2-methylpentylthio, 3-methylpentylthio, 4 -methyl - pentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethyl
  • C 1 -C 6 -alkylthio-C 1 -C 6 -alkyl for: C 1 -C 6 -alkyl-substituted by C 1 -C 6 -alkylthio as mentioned above, for example for CH 2 SCH 3 , CH 2 SC 2 H 5 , CH 2 SCH 2 -C 2 H 5 , CH 2 SCH (CH 3 ) 2 , CH 2 SCH 2 CH 2 -C 2 H 5 , (l-methylpropylthio) methyl, (2-methylpropylthio) methyl, CH 2 SC (CH 3 ) 3 , CH 2 S (CH 2 ) 3- 2 H5, CH 2 S (CH 2 ) 4- 2H5, CH ( CH 3 ) SCH 3 , CH (CH 3 ) SC 2 H 5 , CH 2 CH SCH 3 , CH 2 CH 2 SC 2 H 5 , CH 2 CH 2 SCH 2 -C 2 H 5 , CH 2 CH 2 SCH (CH 3 ) 2 , CH 2 CH 2
  • C 3 -C 7 cycloalkylthio-C 6 -C 6 alkyl for: by C 3 -C 7 cycloalkyl thio such as cyclopropylthio, cyclobutylthio, cyclopentyl thio, cyclohexylthio and cycloheptylthio, preferably cyclopropylthio, substituted C 1 -C 6 alkyl, that is e.g.
  • cyclopropyl-SCH 2 1-cyclopropylthio-ethyl, 2-cyclopropylthio-ethyl, 1-cyclopropylthio-prop-l-yl, 2-cyclopropylthio-prop-l-yl, 3-cyclopropylthio-prop-l-yl, 1 -Cyclopropylthio-but-l-yl, 2-cyclopropylthio-but-l-yl, 3-cyclopropylthio-but-l-yl, 4-cyclopropylthio-but-l-yl, l-cyclopropylthio-but-2-yl, 2 -Cyclopropylthio-but-2-yl, 3-cyclopropylthio-but-2-yl 4-cyclopropyl thio-but-2-yl, 1- (cyclopropyl-SCH 2 -) -eth-l-yl, 1- (cyclopropyl- SCH 2
  • C -Cg-alkylsulfinyl for: e.g. SOCH 3 , S0C 2 H 5 , n-propylsulfinyl, SOCH (CH 3 ) 2 , n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, SOC (CH 3 ) 3 , n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 1 -Methylpentylsulfinyl, 2-methylpentyls
  • Ci-Ce-alkylsulfonyl for: e.g. S0 2 CH 3 , S0 2 C 2 H 5 , n-propylsulfonyl, S0CH (CH 3 ) 2 , n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, S0 2 C (CH 3 ) 3 , n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl,
  • C 6 -C 6 -alkylsulfonyl-C 6 -C 6 -alkyl for: Cx-Cg-alkylsulfonyl substituted as C above ! -C 6 alkyl, e.g.
  • CH 2 S0 2 - (CH 2 ) 4 -C 2 H 5 CH (CH 3 ) S0 2 -CH 3 , CH (CH 3 ) S0 2 -C 2 H 5 , CH 2 CH 2 S0 2 -CH 3 , CH 2 CH 2 S0 2 -C 2 H 5 , CH 2 CH 2 S0 2 -CH 2 -C 2 H 5 , CH 2 CH 2 S0 2 -CH (CH 3 ) 2 , CH 2 CH 2 S0 2 -CH 2 CH -C 2 H 5 , 2- (1-methylpropylsulfonyl) ethyl, 2- (2-methylpropylsulfonyl) ethyl, CH 2 CH 2 S0 2 -C (CH 3 ) 3 , CH 2 CH 2 S0 2 - ( CH 2 ) 3 -C 2 H 5 , CH 2 CH 2 S0 2 - (CH 2 ) 4 -C 2 H 5 ,
  • Di- (Ci-Ce-alkyaminosulfonyl for: e.g. (CH 3 ) 2 N-S0 2 -, (C 2 H 5 > 2 N-S0 2 -, N, N-Dipropylamino-S0 2 -, N, N- Di (1-methyl-ethyl) amino-S0-, N, N-dibutylamino-S0 2 -, N, N-Di (1-methyl-propyl) amino-S02-, N, N-Di (2-methylpropyl) amino-S02-, N, N-Di (1, l-dimethylethyl) amino-S0 2 -, N-ethyl-N-methyl - amino-S0 2 -, N-methyl-N-propylamino-S0-, N- Methyl-N- (1-methylethyl) amino-S02-, N-butyl-N-methylamino-S ⁇ 2-, N-methyl-
  • C 3 -C 8 alkenyl for: C 3 -C ⁇ alkenyl as mentioned above, or for example for n-hept-2-en-1-yl, n-hept-3 -en- 1-yl, n-oct- 2 -en- 1-yl, n-oct-3-en-l-yl, especially for allyl;
  • C 3 -C 8 haloalkenyl for: C 3 -C 8 alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 2-chloroallyl, 3-chloroallyl, 2, 3-dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2, 3, 3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular for 3 -chloroallyl;
  • C 1 -C 6 -alkoxy-C 3 -C 8 -alkenyl for: C 3 -C 8 -alkoxy substituted by -C-C 6 -alkoxy as mentioned above, for example for 3- (methoxy) allyl; C 3 -C 6 alkenyloxy for: e.g. B.
  • C 2 -C 4 -Alkenyloxy-C ⁇ -C 4 alkyl for: by C 3 -C 4 ⁇ alkenyloxy such as vinyloxy, allyloxy, but-l-en-3-yloxy, but-l-en-4 -yloxy, but -2-en-l-yloxy, l-methylprop-2-enyloxy or 2-methyl-prop-2-enyloxy substituted C 1 -C 4 -alkyl, for example for vinyloxymethyl, allyloxymethyl, 2-allyloxyethyl or but-l- en-4-yloxymethyl, especially for 2-allyloxyethyl;
  • C 3 -C 6 alkynyl for: e.g. B. Prop-1-in-l-yl, propargyl, n-but-1 - in-l-yl, n-but-l-in-3-yl, n-but-l-in-4-yl, n- But-2-in-1-yl, n-pent-1-in-1-yl, n-pent-1-in-3-yl, n-pent-1-in-4-yl, n-pent l-in-5-yl, n-pent-2-in-l-yl, n-pent-2 -in-4-yl, n-pent-2-in- 5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-l-yl, n-hex-l- in-3-yl, n-hex-1-in-4-yl, n-hex-1
  • haloalkynyl C 3 -C ⁇ alkynyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for 1,1-difluoroprop-2- in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut-2-in-l-yl, 5-fluoropent-3- in-l-yl or 6-fluoro-hex-4-in-l-yl;
  • C 1 -C 6 -alkoxy-C 3 -C 8 -alkynyl for: C 3 -C 8 -alkynyl substituted by C ⁇ -C 6 -alkoxy as mentioned above, for example for 3-methoxy-prop-2 - in-1- yl;
  • C 3 -C 8 alkynyloxy for: for example propargyloxy, prop-2-in-1-yloxy, n-but-1-in-1-yloxy, n-but-1-in-3-yloxy, n-but- l-in-4-yloxy, n-but-2-in-l-yloxy, n-pent-1-in-l-yloxy, n-pent-l-in-3-yloxy, n-pent-l- in-4-yloxy, n-pent-1-in-5-yloxy, n-pent-2-in-1-yl-oxy, n-pent-2-in-4-yloxy, n-pent-2- in-5-yloxy, 3-methyl-but-l-in-3-yloxy, 3-methyl-but-l-in-4-yloxy, n-hex-1-in-l-yl-oxy, n- Hex-l-in-3-yloxy, n-hex-
  • C 3 -C 4 alkynyloxy -CC -alkyl for: by C 3 -C 4 -alkynyloxy such as propargyloxy, but-l-in-3-yloxy, but-l-in-4-yloxy, but-2- in-l-yloxy, l-methylprop-2-inyloxy and 2-methylprop-2-inyloxy, preferably propargyloxy, substituted C 1 -C 4 -alkyl, for example for propargyloxymethyl or 2-propargoxyethyl, in particular for 2-propargyloxyethyl;
  • the benzyl group (as one of the meanings of R 4 ) is preferably unsubstituted or carries a nitro, halogen, Cx -C 4 alkyl, Ci -C 4 alkoxy or (Ci -C 4 alkoxy) carbonyl substituent .
  • the variables preferably have the following meanings, individually or in combination:
  • R 1 mercapto, hydroxysulfonyl, chlorosulfonyl, aminosulfonyl,
  • Ci-C ⁇ -alkylthio Ci-C ⁇ -alkylsulfinyl or -C-C 6 -alkylsulfonyl, in particular Ci-C 6 -alkylsulfonyl;
  • R 2 halogen, especially chlorine
  • R 3 is hydrogen or halogen, preferably halogen, especially fluorine or chlorine;
  • R 4 is hydrogen, C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, C ⁇ -C 6 -alkoxy, Ci -C 6 -alkoxy-C ⁇ -C 6 - alkyl, Ci -C 6 -alkylthio-Ci - C 6 - alkyl, (Ci -C 6 alkoxy) carbonyl -C ⁇ -C 6 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 alkenyloxy or C3-C6 - Alkynyloxy, especially hydrogen, -C 6 alkyl, cyano -C 6 alkyl, (-C 6 alkoxy) carbonyl -C] . -C 6 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl;
  • R 5 , R 6 independently of one another are hydrogen, C 1 -C 4 alkyl or (C] .- C 4 alkoxy) carbonyl, in particular a chemical bond or Methylene.
  • substituted 2-arylpyridines of the formulas Ib, Ic, Id, le, If, Ig, Ih, Ii, Ik, Im and In are particularly preferred, in particular
  • the substituted 2-arylpyridines of the formula I can be obtained in various ways, for example by one of the following processes:
  • oxidizing agents customary for the oxidation of the pyridine ring are peracetic acid, trifluoroperacetic acid, perbenzoic acid, m-chloroperbenzoic acid, monopermaleic acid, magnesium onoperphthalate, sodium perborate and oxones
  • Suitable solvents are e.g. Water, sulfuric acid, carboxylic acids such as acetic acid and trifluoroacetic acid and halogenated hydrocarbons such as dichloromethane and chloroform.
  • the oxidation is usually successful at temperatures from 0 ° C to the boiling point of the reaction mixture.
  • the oxidizing agent is normally used in at least equimolar amounts, based on the starting compound. In general, an excess of oxidizing agent has proven to be particularly advantageous.
  • IIIIIVM 1 stands for B (OH) 2 , Mg-Cl, Mg-Br, Mg-J, Zn-Cl, Zn-Br, Zn-J, lithium, copper or tin tri (C 1 -C 4 alkyl), preferably for B (OH) 2 , Mg-Cl, Mg-Br, Mg-J, Zn-Cl, Zn-Br or Zn-J.
  • Palladium catalysts such as tetrakis (triphenylphosphine) palladium (0), bis (triphenylphosphine) palladium (II) chloride, 1,4-bis (diphenylphosphino) butane-palladium (II) chloride come in particular as catalysts , 1,2-bis (diphenylphosphino) ethane-palladium (II) chloride, palladiu (II) acetate + triphenylphosphine, palladium (II) acetate + tri - (o-tolyl) -phosphine or palladium on activated carbon, and nickel catalysts such as bis (triphenylphosphine) nickel (II) chloride, 1,3-bis (diphenylphosphino) propane nickel (II) chloride or nickel (II) acetylacetonate.
  • nickel catalysts such as bis (triphenylphosphine) nickel (I
  • aminophenol VIII can also be reacted with oxalic acid (derivatives) XI such as oxalic acid chloride and (if desired substituted) maleic anhydride:
  • Sulfur, -NH- or -N (CH 3 ) - means can be prepared according to synthesis scheme (3):
  • X ' represents oxygen, sulfur, -NH- or -N (CH 3 ) -;
  • R 4 ' represents one of the meanings of R 4 with the exception of hydrogen.
  • the p-fluorophenylpyridines of the formula XII are, for example, analogously to process C) by transition metal-catalyzed cross-coupling reaction of II with XVII
  • R 4 represents one of the meanings of R 4 with the exception of hydrogen.
  • Synthesis scheme (3) ⁇ is obtained by nucleophilic aromatic substitution of the fluorine by a malonic ester residue and subsequent acid hydrolysis with decarboxylation to give the phenylacetic acid derivative XX. With its reduction occurs ⁇ as in the case of XVI; see.
  • Such implementations are also known per se, for example from the following literature:
  • CH 2 can be prepared according to synthesis scheme (5):
  • Alkyl is preferably
  • R 4 represents one of the meanings of R 4 with the exception of hydrogen.
  • Transition metal-catalyzed cross-coupling reaction of the halopyridine II with a boronic acid or trialkyltin compound of the formula XXIII leads to the aldehyde XXIV.
  • XXIV can also be obtained by reacting II with the metal organyl XXI and hydrolysis of the reaction product XXII.
  • the nitro group on the pyridine can be reduced both before and after the alkylation of the benzoxazinone XXXIIa.
  • XXIX one first obtains XXXa or XXXb depending on the reducing agent, its amount and the reduction conditions.
  • O-alkyl preferably Ci-Cg
  • X ' represents oxygen, sulfur, -NH-, -N (CH 3 ) -;
  • R 4 represents one of the meanings of R 4 with the exception of hydrogen.
  • D the literature cited for methods D
  • G the literature cited for methods D
  • the 2 - (-Fluoro-3-nitrophenyl) - 5-nitropyridines XXXV can be obtained by nitrating the corresponding 2 - (4-fluorophenyl) - 5-nitropyridines ⁇ cf. refer to the literature ⁇ listed in Method D ( Figure 2 -. (4-fluorophenyl) - 5 -nitropyridine in turn are, for example analogously to Process C> by cross-coupling reaction of the 2-halo-5-nitropyridine XXXIV with XVII accessible.
  • the substituted 2-arylpyridines I can normally be prepared by one of the synthesis processes mentioned above. For economic or procedural reasons, however, it may be more expedient to prepare some compounds I from similar 2-arylpyridines, but which differ in the meaning of a radical.
  • reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and subsequent
  • Solvent extraction or by removing the solvent, distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase on the
  • the substituted 2-arylpyridines I can be obtained as isomer mixtures which, however, can be separated, if desired, by customary methods such as crystallization or chromatography, also on an optically active adsorbate, in the far ⁇ continuously pure isomers in the production. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.
  • Agricultural salts of the compounds I can be formed by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride.
  • Salts of I, the metal ion of which is not an alkali metal ion, can also be prepared in a conventional manner by salting the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the substituted 2-arylpyridines I are also suitable for the desiccation and / or defoliation of plants.
  • the compounds I or the compositions containing them can be, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous, oily or other suspensions or dispersions, emulsions,
  • Old dispersions, pastes, dusts, sprinkles or granules by spraying, atomizing, dusting, scattering or pouring can be used.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • inert auxiliaries mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tarols as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tarols as well as oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffins, tetrahydronaphthalene, alky
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • emulsions, pastes or old dispersions can be carried out as such or dissolved in a substrate or solvent, can be homogenized in water using wetting agents, adhesives, dispersants or emulsifiers.
  • wetting agents adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl poly
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, 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, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations contain from about 0.001 to 98% by weight, preferably 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 the NMR spectrum).
  • the following formulation examples illustrate the preparation of such preparations:
  • Benzene 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide in 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide in 1 mole of castor oil.
  • an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
  • Wettol ® EM 31 nonionic emulsifier based on ethoxylated castor oil; BASF AG.
  • the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.
  • the substituted 2-arylpyridines I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together.
  • a suspension of 55.4 g 3 was added in portions at 15 to 20 ° C. to a solution of 24.3 g of 3-chlorine -2 - (4-methoxyphenyl) -5-methyl-thiopyridine (from stage 1) in 150 ml of trichloromethane -Chlorper- benzoic acid (from Aldrich; content 56 to 87 wt .-%) in 250 ml trichloromethane. After the addition was complete, stirring was continued for 45 minutes. The resulting 3-chlorobenzoic acid was then filtered off and washed with trichloromethane.
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
  • test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. 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 vessels a few days before the treatment.
  • the application rate for the post-emergence treatment was 15.6 or 7.8 g / ha aS (active substance).
  • the plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • the plants used in the greenhouse experiments are composed of the following types:
  • the young cotton plants were dripping wet with aqueous preparations of the active ingredients (with an addition of 0.15 wt -.% Of the fatty alcohol alkoxylate Plurafac LF ® 700 1), based on the
  • Spray broth treated with leaves.
  • the amount of water applied was the equivalent of 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation in% were determined.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Arylpyridine substituée en 2 répondant à la formule (I) et ses sels. Dans ladite formule (I), R1 = SH, SO¿2?OH, SO2C1, SO2NH2, C1-C6-Alkylthio, C1-C6-Alkyle sulfinyle, C1-C6-alkylsulfonyle, C1-C6-alkylamino-sulfonyle, Di(C1-C6-alkyl)aminosulfonyle; R?2, R3¿ = H, halogène; R4 = H, C¿1?-C6-alkyle, C1-C6-halogenalkyle, cyano-C1-C6-alkyle, C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkyle, C1-C4-halogène-alkoxy-C1-C4-alkyle, C1-C6-alkylthio-C1-C6-alkyle-, C1-C6-alkylsulfinyle-C1-C6-alkyle, C1-C6-alkylsulfonyl-C1-C6 alkyle, C1-C4-alkoxy-C1-C4-alkoxy-C1-C4-alkyle, C1-C6-alkoxycarbonyle-C1-C6-alkyle, C1-C3-alkoxy-C1-C3-alkoxycarbonyl-C1-C6-alkyle, C2-C4-alkenyloxy-C1-C4-alkyle, C3-C4-alkinyloxy-C1-C4-alkyle, C3-C7-cycloalkyle, C3-C7-cycloalkyl-C1-C6-alkyle, C3-C7-cycloalkyloxy-C1-C6-alkyle, C3-C7-cycloalkylthio-C1-C6-alkyle, C3-C8-alkenyle, C3-C8-alkinyle, C3-C8-halogenalkenyle, C3-C8-halogenalkinyle, C1-C6-alkoxy-C3-C8-alkenyle, C1-C6-alkoxy-C3-C8-alkinyle, C1-C6-alkylcarbonyle, C1-C6-alkylsulfonyle, C3-C6-alkenyloxy, C3-C6-alkinyloxy ou benzyl éventuellement substitué; X = -O-, -S-, -NH-, -N(CH3)-, -CH2-; Y = liaison chimique, -CO-, C(R?5,R6); R5,R6¿ = H, NO¿2?, CN, OCH3, SCH3, halogène, C1-C4-alkyle, C1-C4-halogenalkyle, C1-C4-alkoxycarbonyle, C2-C6-alkenyle, C3-C6-alkinyle, C1-C4-alkoxycarbonyl-C1-C4-alkyle. Application: comme herbicide; pour la dessication/défoliation des plantes.
PCT/EP1997/004421 1996-08-22 1997-08-13 Arylpyridine substituee en 2 utilisee comme herbicide Ceased WO1998007720A1 (fr)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6225313B1 (en) 1997-09-17 2001-05-01 Basf Aktiengesellschaft Substituted 2-phenyl-3(2H)-pyridazinones
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides
CN105837564A (zh) * 2016-03-30 2016-08-10 贵州大学 一种含吡啶苯并硫氮杂卓衍生物、其制备方法及用途
WO2019101513A1 (fr) 2017-11-23 2019-05-31 Basf Se Pyridyléthers en tant qu'herbicides
WO2019101551A1 (fr) 2017-11-23 2019-05-31 Basf Se Phényléthers herbicides

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001512117A (ja) * 1997-07-14 2001-08-21 ビーエーエスエフ アクチェンゲゼルシャフト 置換２−（ベンゾアリール）ピリジン
TW200848021A (en) 2007-03-06 2008-12-16 Wyeth Corp Sulfonylated heterocycles useful for modulation of the progesterone receptor

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0263958A1 (fr) * 1986-09-16 1988-04-20 Sumitomo Chemical Company, Limited Dérivés de 2,6-diphénylpyridine substitués en position 4, leur procédé de préparation, intermédiaires chimiques et leur application comme herbicides
EP0451585A2 (fr) * 1990-04-07 1991-10-16 Bayer Ag Derivés de 2-aryl-6-hétéroaryl pyridine
WO1995002590A2 (fr) * 1993-07-16 1995-01-26 Basf Aktiengesellschaft Phenylpyridines 2 fusionnees substituees a action herbicide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0263958A1 (fr) * 1986-09-16 1988-04-20 Sumitomo Chemical Company, Limited Dérivés de 2,6-diphénylpyridine substitués en position 4, leur procédé de préparation, intermédiaires chimiques et leur application comme herbicides
EP0451585A2 (fr) * 1990-04-07 1991-10-16 Bayer Ag Derivés de 2-aryl-6-hétéroaryl pyridine
WO1995002590A2 (fr) * 1993-07-16 1995-01-26 Basf Aktiengesellschaft Phenylpyridines 2 fusionnees substituees a action herbicide

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ARCH. PHARM. (WEINHEIM, GER.), vol. 325, no. 6, 1992, pages 357 - 359 *
CHEMICAL ABSTRACTS, vol. 117, no. 11, 14 September 1992, Columbus, Ohio, US; abstract no. 111445c, K. GOERLITZER, W. DUEWEL: "Pyridine compounds from etacrynic acid. II" page 848; XP002048736 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6225313B1 (en) 1997-09-17 2001-05-01 Basf Aktiengesellschaft Substituted 2-phenyl-3(2H)-pyridazinones
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides
CN105837564A (zh) * 2016-03-30 2016-08-10 贵州大学 一种含吡啶苯并硫氮杂卓衍生物、其制备方法及用途
CN105837564B (zh) * 2016-03-30 2019-02-05 贵州大学 一种含吡啶苯并硫氮杂卓衍生物、其制备方法及用途
WO2019101513A1 (fr) 2017-11-23 2019-05-31 Basf Se Pyridyléthers en tant qu'herbicides
WO2019101551A1 (fr) 2017-11-23 2019-05-31 Basf Se Phényléthers herbicides

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