WO1999059990A1 - Derives pyridil-pyrazole, leur procede de preparation, et leur utilisation en tant qu'herbicides - Google Patents

Derives pyridil-pyrazole, leur procede de preparation, et leur utilisation en tant qu'herbicides Download PDF

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WO1999059990A1
WO1999059990A1 PCT/EP1999/003404 EP9903404W WO9959990A1 WO 1999059990 A1 WO1999059990 A1 WO 1999059990A1 EP 9903404 W EP9903404 W EP 9903404W WO 9959990 A1 WO9959990 A1 WO 9959990A1
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alkyl
formula
halogenalkyl
halogen
hydrogen
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PCT/EP1999/003404
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English (en)
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Kurt Nebel
Alain De Mesmaeker
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Novartis Ag
Novartis-Erfindungen Verwaltungsgesellschaft Mbh
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Priority to AU42637/99A priority Critical patent/AU4263799A/en
Priority to BR9910536-5A priority patent/BR9910536A/pt
Priority to EP99952093A priority patent/EP1080088A1/fr
Publication of WO1999059990A1 publication Critical patent/WO1999059990A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the invention relates to new, herbicidally active, substituted pyridyl-pyrazole derivatives, a process for the preparation thereof, compositions containing these compounds, as well as their usage in controlling weeds, in particular in crops of useful plants, for example cereals, maize, rice, cotton, soya, rape, sorghum, sugar cane, sugar beet, sunflowers, vegetables, plantations and fodder plants, or in inhibiting plant growth.
  • crops of useful plants for example cereals, maize, rice, cotton, soya, rape, sorghum, sugar cane, sugar beet, sunflowers, vegetables, plantations and fodder plants, or in inhibiting plant growth.
  • Phenyl-pyrazole compounds having herbicidal activity are known and are described for example in WO 98/12182.
  • substituted pyridyl-pyrazole derivatives have outstanding herbicidal and growth-inhibiting properties.
  • the present invention thus relates to compounds of formula I
  • n 13 is 1 , 2 or 3;
  • W is a group (W 2 ),
  • R is C ⁇ -C 4 -alkyl, C C 4 -halogenalkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -halogenalkenyl, C 3 -C 6 -cycloalkyl, amino, NHR 8 or NR 8 R 9 ;
  • R 8 and R 9 independently of one another, are C ⁇ -C 4 -alkyl; or
  • R 8 and R 9 together form a C 2 -C 5 -alkylene bridge
  • R 2 signifies hydrogen, C C 4 -alkyl, d-C 4 -halogenalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -haiogenalkenyl,
  • R 3 is hydrogen, C C 4 -alkyl, d-d-halogenalkyl, d-d-hydroxyalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 - halogenalkenyl, C 2 -C 6 -alkynyl, halogen, cyano, NH 2 C(S)-, nitro, OHC- or R ⁇ 8 R ⁇ 9 N- ;
  • R 18 and R 19 independently of one another, are hydrogen, C C 4 -alkyl, d-d-halogenalkyl,
  • R 4 signifies hydrogen, d-C 4 -alkyl, C C 4 -halogenalkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -halogenalkenyl,
  • R 5 signifies hydrogen, halogen, d-C 4 -alkyl, d-C 4 -halogenalkyl, cyano, nitro, amino,
  • Ru signifies hydrogen, fluorine, chlorine, bromine or methyl
  • R 13 is hydrogen, halogen, cyano, CIS(O) 2 -, CIC(O)-, Nitro, Amino, " ⁇ . , HS-,
  • R 20 and R 21 are C ⁇ -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 - C 6 -cycloalkyl, d-C- ⁇ -halogenalkyl, C 3 -C 8 -halogenalkenyl, C ⁇ -C 4 -alkylcarbonyl, C ⁇ -C 4 - halogenalkylcarbonyl, d-C-a-alkylsulphonyl, d-C 8 -halogenalkylsulphonyl, C 2 -C 8 - alkenyisulphonyl, C 2 -C 8 -halogenalkenylsulphonyl, benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, C ⁇ -C 4 -alkyl or C ⁇ -C 4 -halogenalkyl; or R 13
  • R 30 is hydrogen, d-C 8 -alkyl, C C 8 -alkyl-ethylene oxide, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 - cycioalkyl, C r C 8 -halogenalkyl, C 3 -C 8 -halogenalkenyl, C ⁇ -C -alkoxy-C r C 4 -alkyl, C 3 -C 6 - alkenyloxy-d-C 4 -alkyl, C 3 -C 6 -alkynyloxy-C ⁇ -C 4 -alkyl, d-d-alkoxy-d-d-alkoxy-d-d-alkyl, C r C 4 -alkylthio-C ⁇ -C 4 -alkyl, C ⁇ -C 8 -alkoxycarbonyl, C 3 -C 8 -alkenyloxycarbonyl, benz
  • R 31 X, C(O) - [C. -C 8 -alkylene]- R30 is R 3 ⁇ X ⁇ C(O)-d-C 8 -alkyl-,
  • R— N — X t signifies oxygen, sulphur or ⁇ 1 ;
  • X 1 signifies a single bond
  • R 31 signifies hydrogen, C ⁇ -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl, C ⁇ -C 8 - halogenalkyl, C 3 -C 8 -halogenalkenyl, d-C 4 -alkoxy-C ⁇ -C 4 -alkyl, C 3 -C 6 -alkenyloxy-d-C 4 -alkyl,
  • R 2 is hydrogen, C r C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl or d-C 8 - halogenalkyl; or n 2 is 0, 1 or 2; R 33 is d-C ⁇ -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl, d-C 8 -halogenalkyl, C 3 -C 8 - halogenalkenyl, d-d-alkoxy-d-d-alkyl, C3-C6-alkenyioxy-CrC 4 -alkyl, d-d-alkylthio-d- C -alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen, C C 4 -al
  • R— — X 2 is oxygen, sulphur or '35 '
  • R34 is hydrogen, d-C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl, d-C 8 - halogenalkyl, C 3 -C 8 -halogenalkenyl, C ⁇ -C 4 -alkoxy-d-C 4 -alkyl, C 3 -C 6 -alkenyloxy-d-C 4 -alkyl,
  • R 35 signifies hydrogen, d-C 8 -alkyl or C 3 -C 8 -alkenyl
  • R 36 is hydrogen, d-C 8 -alkyl, C 2 -C 8 -alkenyl, C 3 -C 8 -alkynyl or C 3 -C 6 -cycloalkyl;
  • R 37 is hydrogen, C C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, d-C 8 -halogenalkyl, C C 4 - alkylcarbonyl, CrC 4 -halogenalkylcarbonyl, benzoyi or benzoyl which is mono- to trisubstituted on the phenyl ring by halogen, d-d-alkyl or d-d-halogenalkyl; or
  • R 13 is R 40 C(O)-
  • R 40 is hydrogen, fluorine, chlorine, C C 8 -alkyl, C 2 -C 8 -alkenyl, C 2 -C 8 -alkynyl, C 3 -C 6 - cycloalkyl, d-C 8 -halogenalkyi, cyano-d-d-alkyl, C 2 -C 8 -haiogenalkenyl, d-d-alkoxy-Ci-d- alkyl, C 3 -C 6 -alkenyloxy-d-C 4 -alkyl, CrC 4 -alkylthio-d-C 4 -alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen, d-d-alkyl or d-d-halogenalkyl; benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, d-C 4 -alkyl
  • X 3 is oxygen, sulphur, 51 1 or 52 1 ;
  • R 50 is hydrogen, C ⁇ -C 8 -alkyl, C 3 -C 8 -alkenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl, d-C 8 - halogenalkyl, C 3 -C 8 -halogenalkenyl, cyano-C ⁇ -C 4 -alkyl, C ⁇ -C 4 -alkoxy-d-C -alkyl, C 3 -C 6 - alkenyloxy-d-d-alkyl, (oxiranyl)-CH 2 -, oxetanyl-, d-d-alkylthio-d-d-alkyi.
  • phenyl phenyl which is mono- to trisubstituted by halogen, C ⁇ -C -alkyl or d-C -halogenalkyl; benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, d-d-alkyl or d-C 4 - halogenalkyl; phenyl-C 2 -C 6 -alkyl, C C 6 -alkyl-CO-C 1 -C 4 -alkyl,
  • R 53 X 4 C(O)-C 1 -C 6 -alkyl, I or
  • R 53 X 4 C(O)-C 3 -C 6 -cycloalkyl
  • X v4 • is oxygen, su .lphur, RS M 'N i — or R ⁇ « 0-N 1 — ;
  • R53 is hydrogen, d-C 8 -alkyl, C 3 -C 8 -aikenyl, C 3 -C 8 -alkynyl, C 3 -C 6 -cycloalkyl, d-C 8 - halogenalkyl, C 3 -C 8 -halogenalkenyl, cyano-d-C 4 -alkyl, C C 4 -alkoxy-C ⁇ -C 4 -alkyl, C 3 -C 6 - alkenyloxy-d-C 4 -alkyl, (oxiranyl)-CH 2 -, oxetanyl-, C ⁇ -C -alkylthio-d-C 4 -alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen, d-C -alkyl or d-d-halogenalkyl; benzyl or benzyl which is mono- to trisubstituted
  • R51, Rs2» R- ⁇ and R55 independently of one another, are hydrogen, C ⁇ -C 8 -alkyl, C 3 -C 8 - alkenyl, C 3 -C 8 -alkynyl, d-C 8 -halogenalkyi or benzyl; or
  • R13 is B d-C ⁇ -alkyl, B ⁇ -C 2 -C 8 -alkenyl, B C 2 -C 8 -alkynyl, B Ci-Ce-halogenalkyl, B ⁇ -C 2 -C 8 - halogenalkenyl, B C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl I B 1 -C 1 -C 4 -alkylthio-d-C 4 -alkyl or BrC 3 -C 6 - cycloalkyl;
  • B1 is hydrogen, cyano, hydroxy, ethylene oxide, C 3 -C 6 -cycloalkyl, C C 8 -alkoxy, C 3 -C 8 - alkenyloxy, R 60 X 5 C(O)-, d-C 4 -alkylcarbonyl or d-C 4 -halogenalkylcarbonyl ;
  • X 5 has the significance of X 4 ;
  • R ⁇ o has the significance of R5 3 ;
  • B 2 is nitro, cyano or R 71 X 6 C(O)-;
  • R 70 is cyano or R 72 X 7 C(O)-;
  • R 71 and R 72 have the significance of R 53 ;
  • U signifies d- or C 2 -alkylene, -CH 2 -O-, -CH 2 -S-, oxygen or sulphur, as well as agrochemically acceptable salts and stereoisomers of these compounds of formula I.
  • halogen is understood to be iodine, and preferably fluorine, chlorine and bromine.
  • the alkyl, alkenyl and alkynyl groups present in the definitions of the substituents may be straight-chained or branched, and this also applies to the alkyl, alkenyl and alkynyl moiety of the alkylcarbonyl, alkylcarbamoyl, hydroxyalkyl, cyanoalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylthio, alkylthio-alkyl, alkylthio-C(O)-, alkenylcarbamoyl, alkenylthio-C(O)-, alkynylthio-C(O)-, alkylsulphonyl, aikylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonylalkyl, B alkyl,
  • Alkyl groups are for example methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, tert.-butyl as well as the various isomeric pentyl, hexyl, heptyl and octyl radicals. Methyl, ethyl, n-propyl, iso-propyl and n-butyl are preferred.
  • alkenyls which may be mentioned are vinyl, allyl, methallyl, 1 -methylvinyl, but- 2-en-1-yl, pentenyl, 2-hexenyl, 3-heptenyl and 4-octenyl, preferably alkenyl radicals with a chain length of 3 to 5 carbon atoms.
  • alkynyls which may be mentioned are ethynyl, propargyl, 1 -methylpropargyl, 3- butynyl, but-2-yn-1-yl, 2-methylbutyn-2-yl, but-3-yn-2-yl, 1-pentynyl, pent-4-yn-1-yl or 2- hexynyl, preferably alkynyl radicals with a chain length of 2 to 4 carbon atoms.
  • Halogenalkyl may be alkyl groups that are mono- or multi-substituted, especially mono- to trisubstituted, by halogen, whereby halogen individually signifies iodine and in particular fluorine, chlorine and bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2-trifluoroethyl and 2,2,2-trichloroethyl.
  • Halogenalkenyl may be alkenyl groups that are mono- or multi-substituted by halogen, whereby halogen individually signifies bromine, iodine and in particular fluorine and chlorine, for example 2- und 3-fluoropropenyl, 2- and 3-chloropropenyl, 2- and 3- bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl, 4,4,4-trifluoro-but-2-en-1-yl and 4,4,4-trichloro-but-2-en-1 -yl.
  • alkenyl radicals that are mono-, di- or trisubstituted by halogen, preference is given to those which have a chain length of 3 or 4 carbon atoms.
  • the alkenyl groups may be substituted by halogen at saturated or unsaturated carbon atoms.
  • Alkylsulphonyl is for example methyisulphonyl, ethylsulphonyl, propylsulphonyl, iso- propylsulphonyl, n-butylsulphonyl, iso-butylsulphonyl, sec.-butylsulphonyl, tert.- butylsulphonyl; preferably methyisulphonyl and ethylsulphonyl.
  • Halogenalkylsulphonyl is for example fluoromethylsulphonyl, difluoromethyisulphonyl, trifluoromethylsulphonyl, chloromethylsulphonyl, trichloromethylsulphonyl, 2- fluoroethylsulphonyl, 2,2,2-trifluoroethylsulphonyl and 2,2,2-trichloroethylsulphonyl.
  • Alkenylsulphonyl is for example allylsulphonyl, methallylsulphonyl, but-2-en-1 -yl-sulphonyl, pentenylsulphonyl and 2-hexenylsulphonyl.
  • Halogenalkenylsulphonyl is for example 2- and 3-fluoropropenyl-sulphonyl, 2- and 3- chloropropenyl-sulphonyl, 2- and 3-bromopropenyl-suiphonyl, 2,3,3-trifluoropropenyl- sulphonyl, 2,3,3-trichloropropenyl-sulphonyl, 4,4,4-trifluoro-but-2-en-1 -yl-sulphonyl and
  • Cyanoalkyl is for example cyanomethyl, cyanoethyl, cyanoeth-1 -yl and cyanopropyl.
  • Hydroxyalkyl is for example hydroxymethyl, 2-hydroxyethyl and 3-hydroxypropyl.
  • Alkylamino is for example methylamino, ethylamino and the isomeric propyl- and butylamino.
  • Dialkylamino is for example dimethylamino, diethyiamino and the isomeric dipropyl- and dibutylamino.
  • Alkenylamino is for example allylamino, methallylamino and but-2-en-1 -yl-amino.
  • Alkynylamino is for example propargylamino and 1 -methylpropargylamino.
  • Halogenalkylamino is for example chloroethylamino, trifluoroethylamino and
  • Di(halogenalkyl)-amino is for example di(2-chloroethyl)-amino.
  • Alkylcarbonyl is in particular acetyl and propionyl.
  • Halogenalkylcarbonyl is in particular trifluoroacetyl, trichloroacetyl, 3,3,3-trifluoropropionyl and 3,3,3-trichloropropionyl.
  • Alkenylcarbonyl is in particular vinylcarbonyl, allylcarbonyl, methallylcarbonyl, but-2-en-1 -yl- carbonyl, pentenylcarbonyl and 2-hexenylcarbonyl.
  • Alkynylcarbonyl is in particular acetylenecarbonyl, propargylcarbonyl, 1 -methylpropargyl- carbonyl, 3-butynylcarbonyl, but-2-yn-1 -yl-carbonyl and pent-4-yn-1-yl-carbonyl.
  • Alkenyloxy is for example allyloxy, methallyloxy and but-2-en-1-yloxy.
  • Alkynyloxy is for example propargyloxy and 1 -methylpropargyloxy.
  • Alkoxy-alkyl is for example methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n- propoxymethyl, n-propoxyethyl, iso-propoxymethyl and iso-propoxyethyl.
  • Alkenyloxy-alkyl is for example allyloxy-alkyl, methallyloxy-alkyl and but-2-en-1 -yloxy-alkyl.
  • Alkynyloxy-alkyl is for example propargyloxy-alkyl and 1 -methylpropargyloxy-alkyl.
  • Alkoxycarbonyl is for example methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, iso- propoxycarbonyl and n-butoxycarbonyl, preferably methoxycarbonyl and ethoxycarbonyl.
  • Alkenyloxycarbonyl is for example allyloxycarbonyl, methallyloxycarbonyl, but-2-en-1 -yl- oxycarbonyl, pentenyloxycarbonyl and 2-hexenyloxycarbonyl.
  • Alkynyloxycarbonyl is for example propargyloxycarbonyl, 3-butynyloxycarbonyl, but-2-yn-1 - yl-oxycarbonyl and 2-methylbutyn-2-yl-oxycarbonyl.
  • Alkoxyalkoxycarbonyl is for example methoxymethoxycarbonyl, ethoxymethoxycarbonyl, ethoxyethoxycarbonyl, propoxymethoxycarbonyl, propoxyethoxycarbonyl, propoxypropoxycarbonyl and butoxyethoxycarbonyl.
  • Halogenalkoxy is for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, 1 ,1 ,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2,2- trichloroethoxy.
  • cycloalkyl radicals considered as substituents are for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • cycioalkoxycarbonyl radicals considered as substituents are for example cyclopropoxycarbonyl, cyclobutoxycarbonyl, cyclopentoxycarbonyl and cyclohexyloxycarbonyl.
  • Alkylthio signifies for example methylthio, ethylthio, propylthio and butylthio, as well as the branched isomers thereof.
  • Alkylthioalkyl signifies for example methylthioethyl, ethylthioethyl, methylthiopropyl and ethylthiopropyl.
  • Halogenalkylthio-carbonyl is for example fluoromethylthio-carbonyi, difluoromethylthio- carbonyl, trifluoromethylthio-carbonyl, 2,2,2-trifluoroethylthio-carbonyl, 1 ,1 ,2,2- tetrafluoroethylthio-carbonyl, 2-fluoroethylthio-carbonyl, 2-chloroethylthio-carbonyl and
  • the substituents in this case are in ortho-, meta- or para-position.
  • Substituents are e.g. d-d-alkyl, halogen or
  • (C 6 H 5 ) substituted d-C 8 -alkylene chain is additionally substituted by phenyl at one of the 8 carbon atoms, whereby the phenyl ring is mono- to trisubstituted by halogen, d-d-alkyl or d-d- halogenalkyl, and the alkylene chain is straight-chained or branched and may be for example methylene, ethylene, methylethylene, propylene, 1 -methyl-propylene and butylene.
  • d-d- or d-Ce-alkyiene chain is additionally substituted by phenyl (C 6 H 5 ) at one of the 4 or 6 carbon atoms, respectively, whereby the phenyl ring is mono- to trisubstituted by halogen, C ⁇ -C 4 -alkyl or C ⁇ -C -halogenalkyl, and the alkylene chain is straight-chained or branched and may be for example methylene, ethylene, methylethylene, propylene, 1 -methyl- propylene and butylene.
  • cyanoalkyl In the definitions cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, halogenalkenyl-carbonyl, alkynylcarbonyl, alkoxycarbonyl and halogenalkylcarbonyl, the cyano- or carbonyl-carbon atom is not included in the respectively indicated lower and upper limits of the number of carbon atoms.
  • the compounds of formula I are generally present as mixtures consisting of the isomers which are substituted in position 3 and 5 of the pyrazole ring by the pyridyl group (pyrid), for example as isomers IW 1a and IW 1b
  • the isomeric ratio may vary depending on the synthesis process.
  • the invention similarly embraces the salts, which the compounds of formula I may form with bases with acidic hydrogen, especially the derivatives with carboxylic acid and sulphonamide groups (e.g. carboxyl-substituted alkyl, alkylene, alkenyl, alkynyl, alkoxyalkyl, alkylthioalkyl and cycloalkyl groups and NH 2 SO 2 -, alkylS(O) 2 NH- and halogenalkylS(O) 2 NH- substituted pyridyl groups (R13)).
  • the salts in question may be for example alkali metal salts, e.g.
  • alkaline earth metal salts such as calcium and magnesium salts
  • ammonium salts i.e. unsubstituted ammonium salts and mono- or multi- substituted ammonium salts, e.g. triethylammonium and methylammonium salts
  • salts with other organic bases e.g. sodium and potassium salts; alkaline earth metal salts, such as calcium and magnesium salts; ammonium salts, i.e. unsubstituted ammonium salts and mono- or multi- substituted ammonium salts, e.g. triethylammonium and methylammonium salts; or salts with other organic bases.
  • Notable alkali and alkaline earth metal hydroxides as salt-forming components are e.g. the hydroxides of lithium, sodium, potassium, magnesium or calcium, but especially those of sodium and potassium. Suitable salt-forming components are described for example in WO 97/41112.
  • Examples of amines which are suitable for ammonium salt formation may be both ammonia and primary, secondary and tertiary C ⁇ -C ⁇ 8 -alkylamines d-d-hydroxy- alkylamines and C 2 -C 4 -alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecyiamine, methyl-ethylamine, methyl-iso- propylamine, methyl-hexylamine, methyl-nonylamine, methyl-pentadecylamine, methyl-
  • the salts of the compounds of formula I with basic groups are for example salts with inorganic or organic acids, for example hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid, as well as sulphuric acid, phosphoric acid, nitric acid and organic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, citric acid, benzoic acid, oxalic acid, formic acid, benzenesulphonic acid, p-toluenesulphonic acid and methanesulphonic acid.
  • hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid
  • sulphuric acid phosphoric acid
  • nitric acid and organic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glyco
  • W a is a group
  • R 12 is hydrogen, halogen, d-d-alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, d-C 4 -halogenalkyl, C 2 -C 4 - halogenalkenyl, nitro, amino, CHO, d-d-halogenalkoxy, cyano, C 3 -C 6 -cycloalkyl, phenoxy, phenoxy which is mono- to trisubstituted by halogen, C C -alkyl or C C -halogenalkyl; benzyloxy or benzyloxy which is mono- to trisubstituted on the phenyl ring by halogen, C r d-alkyl or Ci-d-halogenalkyl.
  • W 3a (W 3a ) are particularly preferred. Of these compounds, those
  • R T is d-d-alkyl, d-C 4 -halogenalkyl, C 2 - C 4 -alkenyl or C 2 -d-halogenalkenyl;
  • R 3 is chlorine, bromine or methyl;
  • A N-;
  • Rn is hydrogen, fluorine or chlorine;
  • R 5 is halogen, C C -alkyl, d-C 4 -halogenalkyl or cyano; and
  • R ⁇ 2 is halogen.
  • compounds of formula la, wherein W a is the group W a are especially preferred.
  • compounds of formula la, wherein W a is the group W 3 a and R 3 is R ⁇ 8 R ⁇ 9 N- are particularly preferred.
  • Rn, R 13 and n ⁇ 3 have the significances indicated, and W 0 is a group
  • R 10 signifies hydrogen or a protecting group, is either a) when R 10 is hydrogen, reacted with a compound of formula III
  • R,S(O) 2 -L (III), wherein R, has the significance indicated under formula I, and L is a leaving group, in an appropriate solvent and in the presence of a base, or b) when R, 0 is a protecting group, this is firstly cleaved and subsequently the resulting compound of formula II, wherein R, o signifies hydrogen, is reacted as described under a) with a compound of formula III.
  • Appropriate protecting groups are for example benzyl, wherein the phenyl ring may be substituted by halogen, d-d-alkyl, C ⁇ -C 6 -alkoxy, nitro or cyano; allyl, which may be substituted by d-d-alkyl or halogen; tert.-butyl; trityl; benzhydryl (diphenylmethyl); C,-d- alkoxycarbonyl; allyloxycarbonyl; benzyloxycarbonyl, wherein the phenyl ring may be substituted by halogen, d-d-alkyl or d-d-alkoxy; C ⁇ -C -alkylcarbonyi; or benzoyl, wherein the pheny ring may be substituted by halogen, d-C -alkyl or d-d-alkoxy.
  • Cleavage of the benzyl protecting group, which is optionally substituted on the phenyl ring, may also take place under reduction conditions, e.g. using sodium in ammonia, analogously to the manner described in Synthetic Communic. 25, 761 (1995); Chem. Ber. 101 , 3265 (1968); or J. Am. Chem. Soc. 71 , 3994 (1949).
  • Cleavage of the benzyl protecting group, which is optionally substituted on the phenyl ring, may also take place by acidic catalysis, e.g. using trifluoroacetic acid optionally in the presence of an inert organic solvent such as toluene, dichloromethane or 1 ,2-dichloro- ethane, analogously to the manner described in Synthetic Communic. 25, 761 (1995).
  • an inert organic solvent such as cyclohexane, toluene, dichloromethane or chloroform
  • Suitable bases are inorganic bases such as carbonates, for example sodium or potassium carbonate, or sodium or potassium bicarbonate; hydroxides such as sodium, potassium or calcium hydroxide; metal oxides such as calcium oxide; hydrides such as sodium hydride; or organic bases such as alkylamines, for example triethylamine, H ⁇ nig's base (di-isopropyl- ethylamine), dimethyl aniline or diazabicycloundecene (DBU).
  • inorganic bases such as carbonates, for example sodium or potassium carbonate, or sodium or potassium bicarbonate
  • hydroxides such as sodium, potassium or calcium hydroxide
  • metal oxides such as calcium oxide
  • hydrides such as sodium hydride
  • organic bases such as alkylamines, for example triethylamine, H ⁇ nig's base (di-isopropyl- ethylamine), dimethyl aniline or diazabicycloundecene (DBU).
  • L in the compound of formula III signifies a leaving group, such as a halide, imidazolyl, triazolyi or R,S(O) 2 -O-.
  • R 3 is hydrogen, whilst taking into consideration the reactivities of the remaining substituents, by means of halogenation e.g. with elementary chlorine, bromine or iodine, sodium hypochlorite (NaOCI) or iodomonochloride (JCI) in an appropriate solvent and optionally in the presence of a base.
  • halogenation e.g. with elementary chlorine, bromine or iodine, sodium hypochlorite (NaOCI) or iodomonochloride (JCI) in an appropriate solvent and optionally in the presence of a base.
  • suitable bases are for example sodium acetate, imidazole or pyridine.
  • Suitable solvents are e.g. glacial acetic acid, water, alcohols, for example ethanol, chlorinated hydrocarbons, for example chlorobenzene, carbon tetrachloride, 1 ,2-dichloro- ethane, chloroform or 1 ,1 ,2,2-tetrachloroethane.
  • Halogenation may also be carried out in the presence of a catalyst, e.g. a Lewis acid such as iron (III) chloride, iron (III) bromide, aluminium chloride or thallium triacetate.
  • a catalyst e.g. a Lewis acid such as iron (III) chloride, iron (III) bromide, aluminium chloride or thallium triacetate.
  • the corresponding iodination may also conveniently take place in the presence of an oxidation agent, e.g. nitric acid or sulphur trioxide (SO 3 ).
  • an oxidation agent e.g. nitric acid or sulphur trioxide (SO 3 ).
  • reaction temperatures are generally in the range -50°C to boiling point of the solvent employed.
  • the compounds of formula I, wherein R 3 signifies bromine or chlorine may be obtained by reacting the corresponding compounds of formula I, wherein R 3 is hydrogen, with sulphuryl chloride, N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS).
  • NBS N-bromosuccinimide
  • NCS N-chlorosuccinimide
  • the preferred solvent is e.g. carbon tetrachloride.
  • Reactions of this kind are described for example in WO 98/12182 and DE-A-19 638 234.
  • the choice of appropriate preparation method and of corresponding reaction conditions for the functional conversion in the pyridyl moiety is preferably made at an earlier stage of the reaction, taking into consideration the properties (reactivity) of the substituents already present.
  • This functional conversion conveniently takes place in the presence of an appropriate protecting group in the pyrazole increment, e.g. in compounds of formula II, wherein R 10 is for example benzyl.
  • the protecting group e.g. R 10 in the compounds of formula II
  • Such functionalisations in the pyridyl increment are described e.g. in WO 98/21 199.
  • R, 0 signifies a protecting group, such as benzyl, allyl, tert.-butyl, trityl, benzhydryl, alkoxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, alkylcarbonyl or benzoyl.
  • R 10 signifies benzyl or benzyl which is substituted on the phenyl ring by halogen, C,-C 4 -alkyl or d-d-alkoxy, are important intermediates.
  • R 3 , R 4 , Rn, R13, n, and n 13 have the significances indicated under formula I, and R,o signifies benzyl or benzyl which is substituted on the phenyl ring by halogen, d-C 4 -alkyl or d-d-alkoxy, are important intermediates.
  • R 3 , R 5 , R,,, R, 3 and n, 3 have the significances indicated under formula I, and R, 0 signifies benzyl or benzyl which is substituted on the phenyl ring by halogen, C,-C -alkyl or d-d-alkoxy, are important intermediates.
  • the product may be obtained as a mixture of two or more isomers.
  • the isomers may be separated by methods known perse.
  • All application methods that are usual in agriculture may be considered for the usage according to the invention of the compounds of formula I or compositions containing them, such as pre-emergence application, post-emergence application and seed dressing, as well as various methods and techniques such as controlled release of active ingredient.
  • the active ingredient in solution is absorbed onto mineral granulate substrates or polymerised granulates (urea/formaldehyde) and dried.
  • a coating may be additionally given (coated granules), which enables the active ingredient to be dispensed over a certain period of time
  • the compounds may be used in unmodified form, i e. as they are obtained during synthesis, but are preferably processed in conventional manner with the excipients that are customary in formulation techniques, e.g.
  • emulsifiable concentrates directly sprayable or diluable solutions, diluted emulsions, wettable powders, soluble powders, dusts, granules or microcapsuies.
  • Such formulations are described for example in WO 97/34485 on pages 9 to 13.
  • the application process such as spraying, misting, dusting, wetting, scattering or pouring are selected according to the type of agent, the targeted aims and the prevailing conditions.
  • the formulations i.e. the agents, preparations or compositions containing the active ingredient of formula I or at least one active ingredient of formula I and normally one or more solid or liquid formulation excipients, are produced in known manner, e.g. by intimately mixing and/or grinding the active ingredients with the formulation excipients such as solvents or solid carriers.
  • formulation excipients such as solvents or solid carriers
  • surface-active compounds surfactants
  • solvents and solid carriers are given for example in WO 97/34485 on page 6.
  • the surface-active compounds may be non-ionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.
  • suitable anionic, non-ionic and cationic surfactants are listed for example in WO 97/34485 on pages 7 and 8.
  • the surfactants which are customary in formulation techniques, and are described inter alia in "Mc Cutcheon's Detergents and Emulsifiers Annual” MC Publishing Co ⁇ ., Ridgewood New Jersey, 1981 , Stache, H., “Tensid-Taschenbuch", Carl Hanser Verlag, M ⁇ nchen/Wien, 1981 and M. and J. Ash, "Encyclopedia of Surfactants", Vol Mil, Chemical Publishing Co., New York, 1980-81 , are also suitable for the production of the herbicidal compositions according to the invention.
  • the herbicidal formulations normally contain 0.1 to 99 % by weight, especially 0.1 to 95 % by weight, of herbicide, 1 to 99.9 % by weight, especially 5 to 99.8 % by weight, of a solid or liquid formulation excipient and 0 to 25 % by weight, especially 0.1 to 25 % by weight, of a surfactant.
  • compositions may also contain further additives, such as stabilisers, e.g. optionally epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soya oil), antifoaming agents, e.g. silicone oil, preservatives, viscosity regulators, binding agents, tackifiers, as well as fertilizers or other active ingredients.
  • stabilisers e.g. optionally epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soya oil), antifoaming agents, e.g. silicone oil, preservatives, viscosity regulators, binding agents, tackifiers, as well as fertilizers or other active ingredients.
  • stabilisers e.g. optionally epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soya oil)
  • antifoaming agents e.g. silicone oil, preservatives, viscosity regulators, binding agents, tackifier
  • the active ingredients of formula I may be successfully used either as a mixture comprising the isomers la and lb or as pure isomers la or lb on the plant or the locus thereof at application rates of 0.001 to 4 kg/ha, especially 0.005 to 2 kg/ha.
  • the dosage necessary for the desired effect can be determined by tests. It is dependent on the type of activity, the stage of development of the cultivated plant and of the weed, as well as on the application (locus, time, method) and may vary within a wide range depending on these parameters.
  • the compounds of formula I and normally in particular the isomers of formula la, are notable for their herbicidal and growth-inhibiting properties, which enable them to be used in crops of useful plants, especially cereals, cotton, soya, sugar beet, sugar cane, plantations, rape, maize and rice, as well as for non-selective weed control (Total Vegetation Management, TVM). Crops are also understood to be those which have been made tolerant towards herbicides or classes of herbicide by means of conventional breeding or by genetic engineering.
  • the weeds to be controlled are both monocot and dicot weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Sci ⁇ us, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
  • Stellaria Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Solanum, Phaseolus, Echinochloa, Sci ⁇ us, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida,
  • Example P6 Preparation of 3-(5-chloro-3-fluoropyridin-2-ylH-chloromethanesulphonyl- 4,5.6.7-tetrahvdro-1.H.-indazole (isomer A) and 3-(5-chloro-3-fluoropyridin-2-yl)-1- chloromethanesulphonyl-4.5.6.7-tetrahvdro-2.H.-indazole (isomer B)
  • the crude product is purified in a flash chromatography column [silica gel; eluant: n-hexane/ethyl acetate 4/1 (v/v)]. 0.16 g of an isomer A with a m.p. of 108-110°C and 0.08 g of an isomer B as a resin are obtained.
  • Table B Physico-chemical data of compounds produced in the above-mentioned tables. The figure before the point indicates the number of the table, e.g. 36.002 means in Table 36 the compound no. 002 of Table A.
  • Test plants Setaria, Solanum.
  • the compounds according to the invention show good herbicidal action in this test.
  • Table B1 shows an example of the good herbicidal activity of the compounds of formula I.
  • Test plant Setaria Solanum dosage [g AS/ha]
  • Monocot and dicot test plants are raised in standard soil in plastic pots in the greenhouse, and sprayed at the 4- to 6-leaf stage with an aqueous suspension or emulsion of the test substances of formula I, prepared from a 25% emulsion concentrate [example F1 , c)] at a rate of 500 I water/ha, corresponding to a dosage of 2000 g active substance/ha.
  • Test plants Setaria, Sinapsis, Solanum, Ipomea.
  • the compounds of formula I show good herbicidal action in this test.
  • Table B2 shows an example of the good herbicidal activity of the compounds of formula I.
  • Test plant Setaria Sinapis Solanum Ipomea dosage [g AS/ha]
  • the active ingredients of formula I according to the invention may also be used in a mixture with known herbicides as co-herbicides for controlling weeds, for example as ready-to-use formulations or as a "tank mix".
  • the following co-herbicides may be considered for example as components for mixing with the active ingredients of formula I : compound of formula I + Acetochlor; compound of formula I + Acifluorfen; compound of formula I + Aclonifen; compound of formula I + Alachlor; compound of formula I + Ametryn; compound of formula I + Aminotriazol; compound of formula I + Amidosulfuron; compound of formula I + Asulam; compound of formula I + Atrazin; compound of formula I + BAY FOE 5043; compound of formula I + Benazolin; compound of formula I + Bensulfuron; compound of formula I + Bentazone; compound of formula I + Bifenox; compound of formula I + Bispyribac-sodium; compound of formula I + Bialaphos; compound

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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Abstract

L'invention concerne des composés correspondant à la formule (I) dans laquelle A représente =N- ou (a), n13 vaut 1, 2 ou 3, W représente un groupe (W1), (W2), (W3) ou (W4), R1 représente alkyle C1-C4, halogénalkyle C1-C4, alcényle C2-C4, halogénalcényle C2-C4, cycloalkyle C3-C6, amino, NHR8 ou NR8R9; R8 et R9 représentent indépendamment alkyle C1-C4, ou bien ils forment ensemble un pont alkylène C2-C5; R2 représente hydrogène, alkyle C1-C4, halogénalkyle C1-C4, alcényle C3-C6, halogénalcényle C3-C6, alcynyle C3-C6, alkylsulfonyle C1-C4, halogénalkylsulfonyle C1-C4, alcénylsulfonyle C2-C4 ou halogénalcénylsufonyle C2-C4; R3 représente hydrogène, alkyle C1-C4, halogénalkyle C1-C4, hydroxyalkyle C1-C4, alcényle C2-C6, halogénalkyle C2-C6, alcynyle C2-C6, halogène, cyano, NH2C(S)-, nitro, OHC- ou R18R19N-; R18 et R19 représentent chacun indépendamment hydrogène, alkyle C1-C4, halogénalkyle C1-C4, alcényle C3-C4, halogénalcényle C3-C4, cycloalkyle C3-C6, alcynyle C3-C6, alkylcarbonyle C1-C6, halogénalkylcarbonyle C1-C6, alcénylcarbonyle C2-C6, halogénalcénylcarbonyle C2-C6, alkylsulfonyle C1-C6 ou halogénalkylsulfonyle C1-C6; n vaut 0, 1 ou 2; R4 représente hydrogène, alkyle C1-C4, halogénalkyle C1-C4, alcényle C3-C6, halogénalcényle C3-C6, alcynyle C3-C6 ou cycloalkyle C3-C6; R5 représente hydrogène, halogène, alkyle C1-C4, halogénalkyle C1-C4, cyano, nitro, amino, NH2C(S)-, alkylcarbonyle C1-C4, halogénalkylcarbonyle C1-C4, alcénylcarbonyle C2-C4, halogénalkylcarbonyle C2-C4 ou alcynylcarbonyle C2-C4; U représente alkylène C1 ou C2, -CH2-O-, -CH2-S-, oxygène ou soufre; R11 représente hydrogène, fluor, chlore, brome ou méthyle; R13 possède les notations données dans la revendication 1. L'invention concerne également des sels et stéréo-isomères des composés de la formule (I), acceptables sur le plan agrochimique, lesquels ainsi que les composés possèdent des bonnes propriétés herbicides sélectives, de prélevée et postlevée. L'invention concerne en outre la préparation de ces composés de même que l'utilisation de ceux-ci en tant que principes actifs herbicides.
PCT/EP1999/003404 1998-05-20 1999-05-18 Derives pyridil-pyrazole, leur procede de preparation, et leur utilisation en tant qu'herbicides WO1999059990A1 (fr)

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AU42637/99A AU4263799A (en) 1998-05-20 1999-05-18 Pyridyl-pyrazole derivatives, process for their preparation, and their use as herbicides
BR9910536-5A BR9910536A (pt) 1998-05-20 1999-05-18 Derivados de piridila - pirazol, processo para preparação deles, e uso dos mesmos como herbicidas
EP99952093A EP1080088A1 (fr) 1998-05-20 1999-05-18 Derives pyridil-pyrazole, leur procede de preparation, et leur utilisation en tant qu'herbicides

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1108720A1 (fr) * 1999-12-08 2001-06-20 Basf Aktiengesellschaft 2-Pyrazolyl-6-Aryloxy-Pyri(mi)dine herbicide
US6528456B2 (en) 1999-12-08 2003-03-04 Basf Aktiengesellschaft Herbicidal 2-pyrazolyl-6-aryloxypyri(mi)dines
WO2003029243A2 (fr) * 2001-09-24 2003-04-10 Basf Aktiengesellschaft 2-aryloxy-6-pyrazolyl-pyridines

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA3114133A1 (fr) * 2018-12-18 2020-06-25 Indorama Ventures Oxides Llc Tensioactifs aromatiques benzhydryles

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FR2529891A1 (fr) * 1982-07-12 1984-01-13 Nativelle Sa Ets Derives du pyridyl-3 alcoxy-5 pyrazole, procede de preparation et application en therapeutique
DE3623302A1 (de) * 1985-11-09 1987-05-14 Bayer Ag Nicotinsaeurederivate
WO1994029300A1 (fr) * 1993-06-07 1994-12-22 Rhone Poulenc Agrochimie Fongicides pyrazoles substitues en position 3 par un heterocycle
DE19530606A1 (de) * 1995-08-21 1997-02-27 Basf Ag 1-(Pyridyl)-pyrazole
WO1997011943A1 (fr) * 1995-09-26 1997-04-03 Nippon Soda Co., Ltd. Composes de pyrazole, procede de preparation et bactericide agrohorticole
WO1997034485A1 (fr) * 1996-03-15 1997-09-25 Novartis Ag Composition herbicide synergique et procede de lutte contre les mauvaises herbes
WO1997041112A1 (fr) * 1996-04-25 1997-11-06 Novartis Ag Sels de sulfonyluree en tant qu'herbicides
WO1998012182A1 (fr) * 1996-09-19 1998-03-26 Basf Aktiengesellschaft 1-sulfonyl-3-phenylpyrazoles et leur utilisation comme herbicides et pour le dessechement ou la defoliation de vegetaux
WO1998021199A2 (fr) * 1996-11-12 1998-05-22 Novartis Ag Nouveaux herbicides

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2529891A1 (fr) * 1982-07-12 1984-01-13 Nativelle Sa Ets Derives du pyridyl-3 alcoxy-5 pyrazole, procede de preparation et application en therapeutique
DE3623302A1 (de) * 1985-11-09 1987-05-14 Bayer Ag Nicotinsaeurederivate
WO1994029300A1 (fr) * 1993-06-07 1994-12-22 Rhone Poulenc Agrochimie Fongicides pyrazoles substitues en position 3 par un heterocycle
DE19530606A1 (de) * 1995-08-21 1997-02-27 Basf Ag 1-(Pyridyl)-pyrazole
WO1997011943A1 (fr) * 1995-09-26 1997-04-03 Nippon Soda Co., Ltd. Composes de pyrazole, procede de preparation et bactericide agrohorticole
WO1997034485A1 (fr) * 1996-03-15 1997-09-25 Novartis Ag Composition herbicide synergique et procede de lutte contre les mauvaises herbes
WO1997041112A1 (fr) * 1996-04-25 1997-11-06 Novartis Ag Sels de sulfonyluree en tant qu'herbicides
WO1998012182A1 (fr) * 1996-09-19 1998-03-26 Basf Aktiengesellschaft 1-sulfonyl-3-phenylpyrazoles et leur utilisation comme herbicides et pour le dessechement ou la defoliation de vegetaux
WO1998021199A2 (fr) * 1996-11-12 1998-05-22 Novartis Ag Nouveaux herbicides

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1108720A1 (fr) * 1999-12-08 2001-06-20 Basf Aktiengesellschaft 2-Pyrazolyl-6-Aryloxy-Pyri(mi)dine herbicide
US6528456B2 (en) 1999-12-08 2003-03-04 Basf Aktiengesellschaft Herbicidal 2-pyrazolyl-6-aryloxypyri(mi)dines
WO2003029243A2 (fr) * 2001-09-24 2003-04-10 Basf Aktiengesellschaft 2-aryloxy-6-pyrazolyl-pyridines
WO2003029243A3 (fr) * 2001-09-24 2003-09-12 Basf Ag 2-aryloxy-6-pyrazolyl-pyridines

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