WO2000037437A1 - Novel herbicides - Google Patents

Novel herbicides Download PDF

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Publication number
WO2000037437A1
WO2000037437A1 PCT/EP1999/010128 EP9910128W WO0037437A1 WO 2000037437 A1 WO2000037437 A1 WO 2000037437A1 EP 9910128 W EP9910128 W EP 9910128W WO 0037437 A1 WO0037437 A1 WO 0037437A1
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Prior art keywords
alkyl
alkoxy
halogen
alkoxycarbonyl
alkylthio
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PCT/EP1999/010128
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French (fr)
Inventor
Juergen Schaetzer
Alain De Mesmaeker
Shy-Fuh Lee
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Syngenta Participations Ag
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Publication date
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Priority to BR9916396-9A priority Critical patent/BR9916396A/en
Priority to DE69932628T priority patent/DE69932628T2/en
Priority to AU19826/00A priority patent/AU1982600A/en
Priority to EP99963584A priority patent/EP1140811B1/en
Publication of WO2000037437A1 publication Critical patent/WO2000037437A1/en
Priority to US09/886,896 priority patent/US6599861B2/en
Priority to US10/454,966 priority patent/US7265230B2/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged 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
    • A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
    • A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/10—Sulfones; Sulfoxides
    • A—HUMAN NECESSITIES
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    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/20—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom three- or four-membered rings
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • 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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
    • C07D211/86—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/02—1,2-Oxazines; Hydrogenated 1,2-oxazines
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/22—All rings being cycloaliphatic the ring system containing eight carbon atoms, e.g. pentalene

Definitions

  • the present invention relates to novel herbicidally active benzoyl derivatives, to processes for their preparation, to compositions comprising said compounds, and to the use thereof for controlling weeds, in particular in crops of cultivated plants or for inhibiting plant growth.
  • X is L ⁇ -Y R 4 , L 2 -Y 2 -L 3 -Y 3 -R 5 or U-Y 4 -L 5 -Y5-L 6 -Y 6 -R 6 ;
  • C 3 -C 6 -alkenylene which may be substituted by C ⁇ -C -alkyl, halogen, C ⁇ -C 4 -alkoxy, C 2 -C 6 - alkenyl or C 2 -C 6 -alkynyl; or C 3 -C 6 -alkynylene, which may be substituted by CrC -alkyl, halogen, d-C 4 -alkoxy, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl;
  • Y ⁇ , Y 3 , Ye independently of one another, signify oxygen, sulphur, SO, SO 2 , NR 7 , OC(O),
  • R7, Re, R9 and R10 independently of one another, signify hydrogen or CrC 6 -alkyl
  • R1 and R 2 independently of one another, signify halogen, cyano, nitro, amino, CrC 6 -alkyl,
  • R 3 signifies hydrogen, d-C -alkyl or halogen
  • R ⁇ R 5 and R 6 independently of one another, signify hydrogen, d-Ce-alkyl, which may be substituted by the group A ⁇ C 3 -C 7 -cycloalkyl, which may be substituted by the group A 2 ;
  • C 3 -C -cycloalkyl which may be interrupted by 1 to 2 oxygen atoms, sulphur or NRn; C 2 -C 6 - alkenyl, which may be substituted by the group A 3 ; C 3 -C 6 -alkynyl, which may be substituted by the group A 4 ; C 3 -C 7 -cycloalkyl-d-C -alkyl, whereby the cycloalkyl group may be interrupted by 1 to 2 oxygen atoms, sulphur or NRj 2 ; benzyl or phenyl which may in tum be substituted by halogen, C ⁇ -C -alkyl, d-C -alkoxy, d-d-halogenalkyl, cyano, nitro, C ⁇ -C 4 - halogenalkoxy, C ⁇ -C -alkylthio, d-C -alkylsulphinyl, d-C -alkylsul
  • Rn and R ⁇ 2 independently of one another, signify hydrogen or d-C -alkyl
  • R 1 3 and R ⁇ 4 independently of one another, signify hydrogen or d-C 4 -Alkyl
  • Ai, A 2 , A 3 , A are hydroxy, formyl, COOH, CrC 6 -alkoxy,
  • R15 and R ⁇ 6 independently of one another, signify hydrogen or d-C 4 -alkyl
  • Q is the group Q
  • R 39 signifies hydroxy, halogen, Ci-Ce-alkoxy, Ci-Ce-alkylcarbonyloxy, d-C 6 -alkoxy- carbonyloxy, C C 6 -dialkylamino, COOH, d-C 6 -alkenylthio, d-C 6 -alkenylsulphinyl, C ⁇ -C 6 - alkenylsulphonyl, OSO 2 -d-C 6 -alkyl, benzoyloxy or OSO 2 -phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by d-C 4 -alkyl, d-d-halogenaikyl, C ⁇ -C 4 -alkoxy, C ⁇ -C -halogenalkoxy, C ⁇ -C 4 -alkylcarbonyl, C ⁇ -C 4 -alkoxycarbonyl, halogen, nitro, COOH or cyano; V is C 1
  • Ri 7 , R 1 8, i9, R 2 0 , R 21 and R 22 independently of one another, signify hydrogen, Ci-Ce-alkyl, d-Ce-alkoxycarbonyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, d-C 6 -alkylthio, d-C 6 -alkylsulphinyl, d-Ce-alkylsulphonyl, C ⁇ -C -alkylaminosuiphonyl, d-C -halogenalkyl, C ⁇ -C -alkyiamino, d-
  • R 23 signifies hydroxy, halogen, d-C 6 -alkoxy, Ci-Ce-alkyicarbonyloxy, d-C 6 -alkoxy- carbonyloxy, d-C 6 -dialkylamino, COOH, C ⁇ -C 6 -alkylthio, Ci-Ce-alkylsuiphinyl, d-C 6 - alkylsulphonyl, d-C 4 -alkoxycarbonyl-C ⁇ -C 4 -alkylthio, C ⁇ -C 4 -alkoxycarbonyl-C ⁇ -C 4 - alkylsulphinyl, C ⁇ -C 4 -alkoxycarbonyl-d-C -alkylsulphonyl, C ⁇ -C 6 -alkenylthio, d-C 6 - alkenylsulphinyl, d-C 6 -alkenylsulphonyl, OSO 2 -d-C 6
  • R 27 signifies hydroxy, halogen, Ci-Ce-alkoxy, CrCe-alkylcarbonyloxy, Ci-Ce-alkoxy- carbonyloxy, Ci-Ce-dialkylamino, COOH, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, d-Ce- alkylsulphonyl, C ⁇ -C -alkoxycarbonyl-C ⁇ -C -alkylthio, C ⁇ -C -alkoxycarbonyl-C ⁇ -C -alkyl- sulphinyl, d-C -alkoxycarbonyl-CrC 4 -alkylsulphonyl, Ci-Ce-alkenylthio, d-C 6 -alkenyl- sulphinyl, C ⁇ -C 6 -alkenylsulphonyl, OSO 2 -d-C 6 -alkyl, benzoyloxy, phen
  • R33 signifies hydroxy, halogen, Ci-Ce-alkoxy, Ci-C 6 -alkylcarbonyloxy, CrC 6 -alkoxy- carbonyloxy, Ci-Ce-dialkylamino, C r C 6 -alkylthio, Ci-Ce-alkylsulphinyl, d-Ce-alkylsulphonyl, C ⁇ -C 4 -alkoxycarbonyl-d-C -alkylthio, d-C 4 -alkoxycarbonyl-C ⁇ -C 4 -alkylsulphinyl, C -C 4 - alkoxycarbonyl-d-d-alkylsulphonyl, d-C 6 -alkenylthio, d-C 6 -alkenylsulphinyl, CrC 6 - alkenylsulphonyl, OSO 2 -d-C 6 -alkyl, benzoyloxy, phenyl
  • R 34 , R35, R36 and R 37 independently of one another, signify hydrogen, hydroxy, Ci-Ce-alkyl, C ⁇ -C 4 -alkoxy-C ⁇ -C 4 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-Ce-alkoxycarbonyl, Ci-Ce-alkylthio, C Ce-alkylsulphinyl, d-Ce-alkylsulphonyl, C r C 4 -alkylaminosulphonyl, d-C 4 -halogenalkyl, d-Ce-alkylamino, Ci-Ce-dialkylamino, d-C 6 -alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C 1 -C -alkyl, d-C -halogenalkyl, d-C -alkoxy,
  • the invention similarly relates to the salts that may be formed by the compounds of formula I, especially those compounds of formula I in which R 23 , R 27 , R33 and R39 are hydroxy, with amines, alkali metal bases and alkaline earth metal bases, or quaternary ammonium bases.
  • alkali metal hydroxides and alkaline earth metal hydroxides as salt-forming components, the hydroxides of lithium, sodium, potassium, magnesium or calcium are notable, especially those of sodium or potassium.
  • Examples of amines that are suitable for ammonium salt formation may be both ammonia and primary, secondary and tertiary CrC ⁇ 8 -alkylamines, C C 4 -hydroxyalkylamines and C 2 -C 4 -alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, iso- propylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methyl-iso-propylamine, methylhexylamine, methylnonylamine, methyipentadecylamine, methylocta
  • alkyl and alkylene groups present in the definitions of the substituents may be straight- chained or branched and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec- butyl, iso-butyl, tert.-butyl, pentyl and hexyl, as well as the branched isomers thereof.
  • Alkoxy, alkenyl, alkenylene, alkynyl and alkynylene groups are derived from the said alkyl groups.
  • the alkenyl, alkenylene, alkynyl and alkynylene groups may be mono- or multi- unsaturated.
  • Halogen normally signifies fluorine, chlorine, bromine or iodine. The same applies also to halogen in conjunction with other definitions such as halogenalkyl or halogenphenyl.
  • Halogenalkyl groups preferably have a chain length of 1 to 6 carbon atoms.
  • Halogenalkyl is for example fluoromethyl, difluoromethyl, trifluoromethyl, chioromethyl, dichloromethyi, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1 ,1- difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.
  • Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms.
  • Alkoxy is for example methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, iso-butoxy, sec.-butoxy and tert.-butoxy as well as the isomers pentyloxy and hexyloxy; preferably methoxy and ethoxy.
  • Alkylcarbonyl is preferably acetyl or propionyl.
  • Alkoxycarbonyl signifies for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxy- carbonyl, sec.-butoxycarbonyi or tert.-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl.
  • Halogenalkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Halogenalkoxy is e.g.
  • Alkylthio groups preferably have a chain length of 1 to 6 carbon atoms.
  • Alkylthio is for example methylthio, ethylthio, propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec- butylthio or tert.-butylthio, preferably methylthio and ethylthio.
  • Alkylsulphinyl is for example methylsulphinyl, ethylsulphinyl, propyisulphinyl, iso-propylsulphinyl, n-butylsulphinyl, iso- butylsulphinyl, sec.-butylsulphinyl, tert.-butylsulphinyl; preferably methylsulphinyl and ethylsulphinyl.
  • C 3 -C 7 -cycloalkyl which is interrupted by oxygen, is for example oxiranyl, oxetanyl, tetrahydrofuranyl, dioxolanyl, oxacyclohexyl, dioxacyclohexyl, oxacycloheptyl or dioxacycloheptyl.
  • C 3 -C 7 -cycloalkyl-C ⁇ -C 3 -alkyl which may be interrupted by oxygen, is for example oxiranyl- methyl, oxetanyl-ethyl, tetrahydrofuranyl-n-propyl, dioxolanyl-d-C 3 -alkyl, oxacyclohexyl-C ⁇ - C 3 -alkyl, dioxacyclohexyl-d-C 3 -alkyl, oxacycloheptyl-d-C 3 -alkyl or Dioxacycloheptyl-d-C 3 - alkyl.
  • Alkylsulphonyl is for example methylsulphonyl, ethylsulphonyl, propylsulphonyl, iso- propylsulphonyl, n-butylsulphonyl, iso-butyisulphonyl, sec.-butylsulphonyl or tert.- butylsulphonyl; preferably methylsulphonyl or ethylsulphonyl Alkoxyalkoxy groups preferably have a chain length of 2 to 4 carbon atoms.
  • alkoxyalkoxy examples are: methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy or butoxybutoxy.
  • Alkylamino is for example methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines.
  • Dialkylamino is for example dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino.
  • Alkoxyalkyl groups preferably have 2 to 4 carbon atoms.
  • Alkoxyalkyl signifies for example methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxy- methyl or isopropoxyethyl.
  • Alkylthioalkyl groups preferably have 2 to 4 carbon atoms.
  • Alkylthioalkyl signifies for example methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl.
  • the cycloalkyl groups preferably have 3 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Phenyl even as part of a substituent, such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenyialkyl or phenoxyalkyl, may be present in substituted form.
  • Ri and R 2 independently of one another, signify halogen, cyano, nitro, amino, Ci-Ce-alkyl, Ci-Ce-alkoxy, C C 4 -alkoxy-C ⁇ -C 4 - alkyl, Ci-Ce-halogenalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-Ce-alkoxycarbonyl, d-C 6 - alkylcarbonyl, C ⁇ -C 6 -alkylthio, C C 6 -alkylsulphinyl, Ci-Ce-alkylsulphonyl, C C 6 -dialkyl- aminosulphonyl, Ci-Ce-alkylaminosulphonyl, Ci-Ce-halogenalkoxy, OSO 2 -C -C 4 -alkyl, d-C 6 - halogenalkylthio,
  • R 33 signifies hydroxy, halogen, Ci-Ce-alkoxy, Ci-Ce-alkylcarbonyloxy, C ⁇ -C 6 -alkoxy- carbonyloxy, Ci-Ce-dialkylamino, COOH, d-C 6 -alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce- alkylsulphonyl, C ⁇ -C -alkoxycarbonyl-d-C -alkylthio, C ⁇ -C 4 -alkoxycarbonyl-C ⁇ -C 4 - alkylsulphinyl, C ⁇ -C 4 -alkoxycarbonyl-d-C 4 -alkylsulphonyl, C ⁇ -C 6 -alkenylthio, Ci-Ce- alkenylsulphinyl, Ci-Ce-alkenylsulphonyl, OSO 2 -C ⁇ -C 6 -alkyl, benzoyloxy,
  • Q is Q 1 or Q 2 , whereby in the group Q 2 , R 24 , R 25 and R 26 are preferably hydrogen or C ⁇ -C 6 -alkyl.
  • R 23 and R 39 denote hydroxy in particular.
  • X is L 1 -Y 1 - R .
  • U signifies methylene
  • R 2 signifies Ci-Ce-alkylsulphonyl.
  • R 1 signifies methyl.
  • Particularly preferred individual compounds falling within the scope of formula I are: 4-hydroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-bicyclo[3.2.1]oct-3-en- 2-one and 5-hydroxy-4-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-2,6,6- trimethyl-6.H.-[1 ,2]oxazin-3-one.
  • the compounds of formula I may be produced by known processes which are described, for example, in US-A-5,565,410, US-A-5,608,101 and EP-A-0 282 944, whereby e.g. a compound of formula II
  • R 1 t R 2 , R 3 and X have the significances given under formula I and Z signifies a leaving group, preferably halogen, especially chlorine or cyano, is reacted with a compound of formula III (III), wherein the substituents are defined as in group
  • R 39 , R 23 , R 27 and R33 signify hydroxy, optionally in the presence of a base.
  • the compounds of formulae II, III, IV or V are known from US-A-5,565,410, US-A-5,608,101 and EP-A-0282 944 or may be produced analogously to the processes disclosed therein.
  • the reactions for obtaining the compounds of formula I are advantageously carried out in aprotic inert organic solvents.
  • solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloro- methane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile or propionitrile, amides such as N,N-dimethyl formamide, diethyl formamide or N-methylpyrrolidinone.
  • the reaction temperatures are preferably in the range from -20° to +120°C.
  • the reactions are usually slightly exothermic and can as a rule be carried out at room temperature.
  • the reaction mixture can be heated for a brief time to boiling point to shorten the reaction time or also to initiate the reaction.
  • the reaction times can also be shortened by addition of a few drops of a base as reaction catalyst.
  • Particularly suitable bases are tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1 ,4- diazabicyclo[2.2.2]octane, 1 ,5-diazabicyclo[4.3.0]non-5-ene or 1 ,5- diazabicyclo[5.4.0]undec-7-ene.
  • Further suitable bases are also inorganic bases, typically hydrides such as sodium or calcium hydride, hydroxides such as sodium or potassium hydroxide, carbonates such as sodium and potassium carbonate, or hydrogen carbonates such as potassium and sodium hydrogen carbon
  • the compounds of formula I can be isolated in conventional manner by concentrating the reaction mixture and/or removing the solvent by evaporation and by recrystallising or triturating the solid residue in solvents in which they are not readily soluble, typically ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
  • the compounds of formula I or compositions containing them may be used according to this invention by all standard methods of application used in agriculture, including preemergence application, postemergence application and seed dressing, as well as by different methods and techniques such as controlled release.
  • controlled release a solution of the herbicide is applied to a mineral granular carrier or to a polymerised granulate (urea/formaldehyde) and then dried.
  • a coating can then be additionally applied (coated granules) that allows the active ingredient to be released at a controlled rate over a specific period of time.
  • the compounds of formula I may be used as herbicides in unmodified form, i.e. as obtained in the synthesis.
  • they are processed in conventional manner with the auxiliary agents customarily employed in formulation technology to emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates or microcapsules.
  • auxiliary agents customarily employed in formulation technology to emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates or microcapsules.
  • Such formulations are described, for example, in WO 97/34485 on pages 9 to 13.
  • the methods of application such as spraying, atomising, dusting, wetting, scattering or pouring, are selected in accordance with the intended objectives and the prevailing circumstances.
  • the formulations i.e. the agents, preparations, or compositions containing the compound of formula I or at least one compound of formula I and usually one or more than one liquid or solid formulation assistant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the herbicide with said formulation auxiliaries, typically solvents or solid carriers.
  • formulation auxiliaries typically solvents or solid carriers.
  • Surface-active compounds surfactants
  • solvents and solid carriers are described in WO 97/34485 on page 6.
  • suitable surface-active compounds are nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.
  • Suitable anionic, nonionic, and cationic surfactants are listed for example in WO 97/34485 on pages 7 and 8.
  • the herbicidal compositions will as a rule contain from 0.1 to 99 % by weight, preferably from 0.1 to 95% by weight, of herbicide, from 1 to 99.9% by weight, preferably from 5 to 99.8% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant. Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations.
  • the compositions may also contain further ingredients, such as: stabilisers, e.g.
  • epoxidised vegetable oils epoxidised coconut oil, rapeseed oil, or soybean oil
  • anti-foaming agents typically silicone oil
  • preservatives viscosity regulators
  • binders binders
  • tackifiers as well as fertilisers or other chemical agents.
  • the compounds of formula I are usually applied with success to the plants or the locus thereof in concentrations of 0.001 to 4 kg/ha, preferably 0.005 to 2 kg/ha.
  • concentration required to achieve the desired action can be determined by experimentation. It will depend on the type of action, the development stage of the cultivated plant and of the weed, as well as on the application (locus, time, method), and as a resulty of these variables can vary over a wide range.
  • the compounds of formula I have excellent herbicidal and growth inhibiting properties, which make them suitable for application in crops of cultivated plants, especially in cereals, cotton, soybeans, sugar beet, sugar cane, plantations, rape, maize, and rice, and for the non-selective control of weeds. Crops will also be understood to mean those crops that have been made tolerant to herbicides or classes of herbicides by conventional breeding or genetic engineering methods.
  • the weeds to be controlled may be monocot as well as dicot weeds, typically Stellaria, Nasturtium, Agrostis, Digita ⁇ a, Avena, Seta ⁇ a, Sinapis, Lolium, Solanum, 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, Digita ⁇ a, Avena, Seta ⁇ a, Sinapis, Lolium, Solanum, Echinochloa, Sci ⁇ us, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida
  • a solution of 1.5 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid in 15 ml of methylene chloride produced in accordance with EP-A-0 282 944 is mixed at a temperature of 20°C with 2 drops of DMF. Then, whilst cooling lightly, a solution of 1.0 ml (11.6 mmols) of oxalyl chloride in 2 ml of methylene chloride is added dropwise. The reaction mixture is stirred until the evolution of gas has ended. Subsequently, the solvent is distilled off. The 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride is used without further purification directly for the next step of the process.
  • reaction mixture is stirred for half an hour at a temperature of 0°C and is subsequently diluted with methylene chloride. After washing and drying, the organic phase is concentrated by evaporation. 2.23 g of 4-methylsulphonyl-3-methoxymethyl-2-methyl- benzoic acid-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl-ester is obtained in amorphous form. This can be used for the next step without purification.
  • X 2 CH 2 OC 2 H 5
  • X 5 CH 2 CH 2 OC 2 H 5
  • X 6 CH 2 CH 2 OCH 2 CH 2 OCH 3
  • X 7 CH 2 CH 2 OCH 2 CH 2 OC 2 H 5
  • X 8 CH(CH 3 )OC 2 H 5
  • X11 CH 2 OCH 2 CH 2 CH 3
  • X ⁇ 2 CH(C 2 H 5 )OC 2 H 5
  • X 1 3 C(CH 3 ) 2 OH
  • X CH 2 CH 2 OCH(CH 3 ) 2
  • Xis CH 2 SO 2 CH 3
  • X ⁇ e CH 2 N

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Abstract

Compounds of formula (I), wherein the substituents are defined as in claim 1, as well as the agronomically acceptable salts, isomers and enantiomers of these compounds, as well as the agronomically acceptable salts/N-oxides/isomers/enantiomers of these compounds, are eminently suitable for use as herbicides.

Description

Novel herbicides
The present invention relates to novel herbicidally active benzoyl derivatives, to processes for their preparation, to compositions comprising said compounds, and to the use thereof for controlling weeds, in particular in crops of cultivated plants or for inhibiting plant growth.
Benzoyl derivatives with herbicidal activity are described for example in US-A-5.094.685. Now, novel benzoyl derivatives with herbicidal and growth-inhibiting properties have been found.
The objects of the present invention are thus compounds of formula I
Figure imgf000003_0001
wherein
X is Lι-Y R4 , L2-Y2-L3-Y3-R5 or U-Y4-L5-Y5-L6-Y6-R6; X-z, , U, U, U, independently of one another, signify d-C6-alkylene, which may be substituted by Cι-C -alkyl, halogen, C C4-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl; or
C3-C6-alkenylene, which may be substituted by Cι-C -alkyl, halogen, Cι-C4-alkoxy, C2-C6- alkenyl or C2-C6-alkynyl; or C3-C6-alkynylene, which may be substituted by CrC -alkyl, halogen, d-C4-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl;
Yι, Y3, Ye, independently of one another, signify oxygen, sulphur, SO, SO2, NR7, OC(O),
NR8SO2or OSO2;
Y2, Y , Y5, independently of one another, signify oxygen, sulphur, SO, SO2, NR9, OC(O) or
NR10SO2;
R7, Re, R9 and R10, independently of one another, signify hydrogen or CrC6-alkyl;
R1 and R2, independently of one another, signify halogen, cyano, nitro, amino, CrC6-alkyl,
CrCe-alkoxy, C C4-alkoxy-Cι-C4-alkyl, CrC6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl,
CrCe-alkoxycarbonyl, CrC6-alkylcarbonyl, Cι-C6-alkylthio, Cι-C6-alkylsulphinyl, d-C6- alkylsulphonyl, d-C6-dialkylaminosulphonyl, d-C6-alkylaminosulphonyl, C C4- alkylsulphonylamino, C C6-halogenalkoxy, OSO2-C C4-alkyl, Cι-C6-halogenalkylthio, d-C6- halogenalkylsulphinyl, Ci-Ce-halogenalkylsulphonyl, phenylthio, phenylsuiphinyl or phenylsulphonyl;
R3 signifies hydrogen, d-C -alkyl or halogen;
R^ R5 and R6, independently of one another, signify hydrogen, d-Ce-alkyl, which may be substituted by the group A^ C3-C7-cycloalkyl, which may be substituted by the group A2;
C3-C -cycloalkyl, which may be interrupted by 1 to 2 oxygen atoms, sulphur or NRn; C2-C6- alkenyl, which may be substituted by the group A3; C3-C6-alkynyl, which may be substituted by the group A4; C3-C7-cycloalkyl-d-C -alkyl, whereby the cycloalkyl group may be interrupted by 1 to 2 oxygen atoms, sulphur or NRj2; benzyl or phenyl which may in tum be substituted by halogen, Cι-C -alkyl, d-C -alkoxy, d-d-halogenalkyl, cyano, nitro, Cι-C4- halogenalkoxy, Cι-C -alkylthio, d-C -alkylsulphinyl, d-C -alkylsulphonyl, Cι-C - dialkylamino, Cι-C -alkylcarbonyl, d-C4-dialkylaminosulphonyl or NR13-CO-R1 ;
Rn and Rι2, independently of one another, signify hydrogen or d-C -alkyl;
R13 and Rι4, independently of one another, signify hydrogen or d-C4-Alkyl;
Ai, A2, A3, A,, independently of one another, are hydroxy, formyl, COOH, CrC6-alkoxy,
Cι-C4-alkylthio, d-C -alkylsulphinyl, d-C4-alkylsulphonyl, OSO2-C C4-alkyl, d-C6- alkylamino, Ci-Ce-dialkylamino, d-C6-alkylaminocarbonyl, Cι-C6-dialkylaminocarbonyl, nitro, halogen, cyano, d-d-alkoxyhalogen, d-C -alkylcarbonyl, d-C4-alkoxycarbonyi or phenyl, whereby the phenyl group may in turn be substituted by halogen, C C4-alkyl, d-C -alkoxy, d-C4-halogenalkyl, cyano, nitro, Cι-C -halogenalkoxy, C C -alkylthio, d-C4-alkylsulphinyl,
CrC4-alkylsulphonyl, d-C4-alkylcarbonyl, d-C -dialkylaminosulphonyl or NR15-CO-R16;
R15 and Rι6, independently of one another, signify hydrogen or d-C4-alkyl;
Q is the group Q,
Figure imgf000004_0001
wherein R39 signifies hydroxy, halogen, Ci-Ce-alkoxy, Ci-Ce-alkylcarbonyloxy, d-C6-alkoxy- carbonyloxy, C C6-dialkylamino, COOH, d-C6-alkenylthio, d-C6-alkenylsulphinyl, Cι-C6- alkenylsulphonyl, OSO2-d-C6-alkyl, benzoyloxy or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by d-C4-alkyl, d-d-halogenaikyl, Cι-C4-alkoxy, Cι-C -halogenalkoxy, Cι-C4-alkylcarbonyl, Cι-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano; V is C1-C4-alkylene, oxygen, sulphur, SO or SO2;
Ri7, R18, i9, R20 , R21 and R22, independently of one another, signify hydrogen, Ci-Ce-alkyl, d-Ce-alkoxycarbonyl, C2-C6-alkenyl, C2-C6-alkynyl, d-C6-alkylthio, d-C6-alkylsulphinyl, d-Ce-alkylsulphonyl, Cι-C -alkylaminosuiphonyl, d-C -halogenalkyl, Cι-C -alkyiamino, d-
C4-dialkylamino, Ci-Ce-alkoxy, cyano, nitro, halogen or phenyl, q is 1 or 2; or Q is the group Q2
Figure imgf000005_0001
wherein
R23 signifies hydroxy, halogen, d-C6-alkoxy, Ci-Ce-alkyicarbonyloxy, d-C6-alkoxy- carbonyloxy, d-C6-dialkylamino, COOH, Cι-C6-alkylthio, Ci-Ce-alkylsuiphinyl, d-C6- alkylsulphonyl, d-C4-alkoxycarbonyl-Cι-C4-alkylthio, Cι-C4-alkoxycarbonyl-Cι-C4- alkylsulphinyl, Cι-C4-alkoxycarbonyl-d-C -alkylsulphonyl, Cι-C6-alkenylthio, d-C6- alkenylsulphinyl, d-C6-alkenylsulphonyl, OSO2-d-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by d-C4-alkyl, Cι-C4-halogenalkyl, d-C4-alkoxy, d-C4- halogenalkoxy, d-C4-alkylcarbonyl, d-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano; R24 and R25, independently of one another, signify hydrogen, hydroxy, Ci-Ce-alkyl, Cι-C4- alkoxy-d-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Ce-alkoxycarbonyl, d-C6-alkylthio, Ci-Ce-alkylsulphinyl, d-Ce-alkylsulphonyl, Cι-C4-alkylaminosulphonyl, Cι-C -halogenalkyl, Cι-C6-alkylamino, Ci-Ce-dialkylamino, Ci-Ce-alkoxy, cyano, nitro, halogen or phenyl, which may in tum be substituted by d-C4-alkyl, d-C -halogenalkyl, d-C4-alkoxy, Cι-C4- halogenalkoxy, Cι-C4-alkylcarbonyl, d-C -alkoxycarbonyl, amino, Cι-C -alkylamino, Cι-C - dialkylamino, d-C6-alkylthio, Ci-Ce-alkylsulphinyl, d-C6-alkylsulphonyl, Cι-C -alkyl-S(O)2O, Cι-C4-halogenalkylthio, d-C -halogenalkylsulphinyl, Cι-C4-halogenalkylsulphonyl, d-C - halogenalkyl-S(O)2O, Cι-C4-alkyl-S(O)2NH, Cι-C4-alkyl-S(O)2N(d-C4-alkyl), halogen, nitro, COOH or cyano; or R24 and R25 together form a C2-C6-alkylene bridge, R26 signifies hydrogen, Cι-C -alkyl, Cι-C4-alkoxycarbonyl or phenyl, which may in turn be substituted by Ci-Ce-alkyl, Cι-C6-halogenalkyl, Ci-Ce-alkoxy, Ci-Ce-halogenalkoxy, d-C6- alkylcarbonyl, Ci-Ce-alkoxycarbonyl, amino, Cι-C4-alkylamino, Cι-C -dialkylamino, d-C6- alkylthio, Ci-Ce-alkylsulphinyl, d-Ce-alkylsulphonyl, Cι-C4-alkyl-S(O)2O, d-d-halogen- alkylthio, d-C4-halogenalkylsulphinyl, d-C4-halogenalkylsulphonyl, Cι-C -halogenalkyl- S(O)2O, Cι-C4-alkyl-S(O)2NH, Cι-C4-alkyl-S(O)2N(Cι-C4-alkyl), halogen, nitro, COOH or cyano; or Q is the group Q3
Figure imgf000006_0001
wherein
R27 signifies hydroxy, halogen, Ci-Ce-alkoxy, CrCe-alkylcarbonyloxy, Ci-Ce-alkoxy- carbonyloxy, Ci-Ce-dialkylamino, COOH, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, d-Ce- alkylsulphonyl, Cι-C -alkoxycarbonyl-Cι-C -alkylthio, Cι-C -alkoxycarbonyl-Cι-C -alkyl- sulphinyl, d-C -alkoxycarbonyl-CrC4-alkylsulphonyl, Ci-Ce-alkenylthio, d-C6-alkenyl- sulphinyl, Cι-C6-alkenylsulphonyl, OSO2-d-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in tum be substituted by Cι-C4-alkyl, d-C4-halogenalkyl, d-C -alkoxy, d-C -halogen- alkoxy, Cι-C4-alkylcarbonyl, d-C -alkoxycarbonyl, halogen, nitro, COOH or cyano; 28, R29 and F o, independently of one another, signify hydrogen, hydroxy, Ci-Ce-alkyl, Cι-C -alkoxy-Cι-C -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxycarbonyl, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, d-C6-alkylsulphonyl, Cι-C -alkylaminosuiphonyl, Cι-C -halogenalkyl, Ci-Ce-alkylamino, Ci-Ce-dialkylamino, Ci-Ce-alkoxy, cyano, nitro, halogen or phenyl, which may in tum be substituted by C C4-alkyl, d-C4-halogenalkyl, Cι-C4-alkoxy, d-C -halogen- alkoxy, Cι-C4-alkylcarbonyl, Cι-C4-alkoxycarbonyl, amino, Cι-C -alkylamino, C1-C4-dialkyl- a ino, CrC6-alkylthio, Ci-Ce-alkylsulphinyl, d-C6-alkylsulphonyl, d-C4-alkyl-S(O)2O, d-C - halogenalkylthio, Cι-C -halogenalkylsulphinyl, Cι-C -halogenalkylsulphonyl, C C4-halogen- alkyl-S(O)2O, Cι-C4-alkyl-S(O)2NH, Cι-C4-alkyl-S(O)2N(d-C4-alkyl), halogen, nitro, COOH or cyano; or R28 and R29 together form a C2-C6-alkylene bridge, R30 signifies Ci-Ce-alkyl, which may be substituted by a group A5; C2-C6-alkenyl, which may be substituted by a group A6; C2-C6-alkynyl, which may be substituted by a group A7; A5, A6 and A7, independently of one another, are hydroxy, formyl, COOH, Ci-Ce-alkoxy, Cι-C -alkylthio, Cι-C4-alkylsulphinyl, d-C4-alkylsulphonyl, OSO2-Cι-C4-alkyl, d-C6- alkylamino, Ci-C6-dialkylamino, Ci-Ce-alkylaminocarbonyl, Ci-Ce-dialkylaminocarbonyl, nitro, halogen, cyano, Cι-C4-alkoxyhalogen, Cι-C4-alkylcarbonyl, d-C4-alkoxycarbonyl or phenyl, whereby the phenyl is in turn substituted by halogen, Cι-C -alkyl, d-C -alkoxy, Cι-C - halogenalkyl, cyano, nitro, Cι-C -haiogenalkoxy, Cι-C4-alkylthio, Cι-C4-alkylsuiphinyl, Cι-C4- alkylsulphonyl, Cι-C -alkylcarbonyl, Cι-C4-dialkylaminosulphonyl or NR31-CO-R32; R31, R32, independently of one another, signify hydrogen or Cι-C4-alkyl; or Q is the group Q
Figure imgf000007_0001
wherein
R33 signifies hydroxy, halogen, Ci-Ce-alkoxy, Ci-C6-alkylcarbonyloxy, CrC6-alkoxy- carbonyloxy, Ci-Ce-dialkylamino, CrC6-alkylthio, Ci-Ce-alkylsulphinyl, d-Ce-alkylsulphonyl, Cι-C4-alkoxycarbonyl-d-C -alkylthio, d-C4-alkoxycarbonyl-Cι-C4-alkylsulphinyl, C -C4- alkoxycarbonyl-d-d-alkylsulphonyl, d-C6-alkenylthio, d-C6-alkenylsulphinyl, CrC6- alkenylsulphonyl, OSO2-d-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in tum be substituted by Cι-C4-alkyl, C -C -halogenalkyl, Cι-C4-alkoxy, d-C -halogenalkoxy, Cι-C4- alkylcarbonyl, C -C4-alkoxycarbonyl, halogen, nitro, COOH or cyano; W is oxygen, sulphur, SO, SO2, NR38 or C=O; R38 signifies hydrogen or Ci-Ce-alkyl;
R34, R35, R36 and R37, independently of one another, signify hydrogen, hydroxy, Ci-Ce-alkyl, Cι-C4-alkoxy-Cι-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Ce-alkoxycarbonyl, Ci-Ce-alkylthio, C Ce-alkylsulphinyl, d-Ce-alkylsulphonyl, CrC4-alkylaminosulphonyl, d-C4-halogenalkyl, d-Ce-alkylamino, Ci-Ce-dialkylamino, d-C6-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by C1-C -alkyl, d-C -halogenalkyl, d-C -alkoxy, C C4-halogen- alkoxy, Cι-C4-aikylcarbonyl, d-C -alkoxycarbonyl, amino, d-C4-alkylamino, Cι-C4-dialkyl- amino, d-C6-alkylthio, Ci-C6-alkylsulphinyl, Ci-Ce-alkylsulphonyl, Cι-C4-alkyl-S(O)2O, Cι-C - halogenalkylthio, C -C4-halogenalkylsulphinyl, Cι-C4-halogenalkylsulphonyl, Cι-C -halogen- alkyl-S(O)2O, Cι-C -alkyl-S(O)2NH, Cι-C -alkyl-S(O)2N(Cι-C4-alkyl), halogen, nitro, COOH or cyano; or R34 and R35 together form a C2-C6-alkylene bridge, as well as agronomically acceptable salts, isomers and enantiomers of these compounds.
The invention similarly relates to the salts that may be formed by the compounds of formula I, especially those compounds of formula I in which R23, R27, R33 and R39 are hydroxy, with amines, alkali metal bases and alkaline earth metal bases, or quaternary ammonium bases.
Of the alkali metal hydroxides and alkaline earth metal hydroxides as salt-forming components, the hydroxides of lithium, sodium, potassium, magnesium or calcium are notable, especially those of sodium or potassium.
Examples of amines that are suitable for ammonium salt formation may be both ammonia and primary, secondary and tertiary CrCι8-alkylamines, C C4-hydroxyalkylamines and C2-C4-alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, iso- propylamine, the four isomeric butylamines, n-amylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methyl-iso-propylamine, methylhexylamine, methylnonylamine, methyipentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propyiamine, di-iso-propylamine, di-n-butylamine, di-n- amylamine, di-iso-amylamine, dihexyiamine, diheptylamine, dioctylamine, ethanolamine, n- propanolamine, iso-propanolamine, N,N-diethanolamine, N-ethylpropanolamine, N-butyl- ethanoiamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2- amine, di-butenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, tπ'-iso-propylamine, tri-n-butylamine, tri-iso-butylamine, tri- sec.-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines such as pyridine, quinoline, iso-quinoline, moφholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines such as anilines, methoxyanilines, ethoxyanilines, o,m,p-toluidines, phenylenediamines, benzidines, naphthylamines and o,m,p-chloroanilines; but especially triethylamine, iso-propylamine and di-iso-propylamine. The alkyl and alkylene groups present in the definitions of the substituents may be straight- chained or branched and are, for example, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec- butyl, iso-butyl, tert.-butyl, pentyl and hexyl, as well as the branched isomers thereof. Alkoxy, alkenyl, alkenylene, alkynyl and alkynylene groups are derived from the said alkyl groups. The alkenyl, alkenylene, alkynyl and alkynylene groups may be mono- or multi- unsaturated.
Halogen normally signifies fluorine, chlorine, bromine or iodine. The same applies also to halogen in conjunction with other definitions such as halogenalkyl or halogenphenyl.
Halogenalkyl groups preferably have a chain length of 1 to 6 carbon atoms. Halogenalkyl is for example fluoromethyl, difluoromethyl, trifluoromethyl, chioromethyl, dichloromethyi, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1 ,1- difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl and dichlorofluoromethyl.
Alkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Alkoxy is for example methoxy, ethoxy, propoxy, i-propoxy, n-butoxy, iso-butoxy, sec.-butoxy and tert.-butoxy as well as the isomers pentyloxy and hexyloxy; preferably methoxy and ethoxy. Alkylcarbonyl is preferably acetyl or propionyl. Alkoxycarbonyl signifies for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, iso-propoxycarbonyl, n-butoxycarbonyl, iso-butoxy- carbonyl, sec.-butoxycarbonyi or tert.-butoxycarbonyl; preferably methoxycarbonyl or ethoxycarbonyl. Halogenalkoxy groups preferably have a chain length of 1 to 6 carbon atoms. Halogenalkoxy is e.g. fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, 1,1 ,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-difluoroethoxy and 2,2,2-trichloroethoxy; preferably difluoromethoxy, 2-chloroethoxy and trifluoromethoxy. Alkylthio groups preferably have a chain length of 1 to 6 carbon atoms. Alkylthio is for example methylthio, ethylthio, propylthio, iso-propylthio, n-butylthio, iso-butylthio, sec- butylthio or tert.-butylthio, preferably methylthio and ethylthio. Alkylsulphinyl is for example methylsulphinyl, ethylsulphinyl, propyisulphinyl, iso-propylsulphinyl, n-butylsulphinyl, iso- butylsulphinyl, sec.-butylsulphinyl, tert.-butylsulphinyl; preferably methylsulphinyl and ethylsulphinyl. C3-C7-cycloalkyl, which is interrupted by oxygen, is for example oxiranyl, oxetanyl, tetrahydrofuranyl, dioxolanyl, oxacyclohexyl, dioxacyclohexyl, oxacycloheptyl or dioxacycloheptyl.
C3-C7-cycloalkyl-Cι-C3-alkyl, which may be interrupted by oxygen, is for example oxiranyl- methyl, oxetanyl-ethyl, tetrahydrofuranyl-n-propyl, dioxolanyl-d-C3-alkyl, oxacyclohexyl-Cι- C3-alkyl, dioxacyclohexyl-d-C3-alkyl, oxacycloheptyl-d-C3-alkyl or Dioxacycloheptyl-d-C3- alkyl.
Alkylsulphonyl is for example methylsulphonyl, ethylsulphonyl, propylsulphonyl, iso- propylsulphonyl, n-butylsulphonyl, iso-butyisulphonyl, sec.-butylsulphonyl or tert.- butylsulphonyl; preferably methylsulphonyl or ethylsulphonyl Alkoxyalkoxy groups preferably have a chain length of 2 to 4 carbon atoms.
Examples of alkoxyalkoxy are: methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy, propoxymethoxy or butoxybutoxy.
Alkylamino is for example methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines. Dialkylamino is for example dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino and diisopropylamino. Preference is given to alkylamino groups with a chain length of 1 to 4 carbon atoms. Alkoxyalkyl groups preferably have 2 to 4 carbon atoms. Alkoxyalkyl signifies for example methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxy- methyl or isopropoxyethyl. Alkylthioalkyl groups preferably have 2 to 4 carbon atoms. Alkylthioalkyl signifies for example methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthioethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butylthiomethyl, butylthioethyl or butylthiobutyl. The cycloalkyl groups preferably have 3 to 6 ring carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. Phenyl, even as part of a substituent, such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenyialkyl or phenoxyalkyl, may be present in substituted form.
Preference is given to compounds of formula I, in which Ri and R2, independently of one another, signify halogen, cyano, nitro, amino, Ci-Ce-alkyl, Ci-Ce-alkoxy, C C4-alkoxy-Cι-C4- alkyl, Ci-Ce-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Ce-alkoxycarbonyl, d-C6- alkylcarbonyl, Cι-C6-alkylthio, C C6-alkylsulphinyl, Ci-Ce-alkylsulphonyl, C C6-dialkyl- aminosulphonyl, Ci-Ce-alkylaminosulphonyl, Ci-Ce-halogenalkoxy, OSO2-C -C4-alkyl, d-C6- halogenalkylthio, Ci-Ce-halogen-alkylsulphinyl, Ci-Ce-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl and
R33 signifies hydroxy, halogen, Ci-Ce-alkoxy, Ci-Ce-alkylcarbonyloxy, Cι-C6-alkoxy- carbonyloxy, Ci-Ce-dialkylamino, COOH, d-C6-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce- alkylsulphonyl, Cι-C -alkoxycarbonyl-d-C -alkylthio, Cι-C4-alkoxycarbonyl-Cι-C4- alkylsulphinyl, Cι-C4-alkoxycarbonyl-d-C4-alkylsulphonyl, Cι-C6-alkenylthio, Ci-Ce- alkenylsulphinyl, Ci-Ce-alkenylsulphonyl, OSO2-Cι-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by Cι-C4-alkyl, d-C -halogenalkyl, Cι-C4-alkoxy, d-C4- halogenalkoxy, Cι-C -alkylcarbonyl, Cι-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano.
Further preferred compounds of formula I are characterised in that Q is Q1 or Q2, whereby in the group Q2, R24, R25 and R26 are preferably hydrogen or Cι-C6-alkyl. R23 and R39 denote hydroxy in particular. Also notable are those compounds of formula I, in which X is L1-Y1- R . Of this group, the compounds in which U signifies methylene are preferred. In a further preferred group of compounds of formula I, R2 signifies Ci-Ce-alkylsulphonyl. Also of interest are compounds of formula I, in which R1 signifies methyl.
Particularly preferred individual compounds falling within the scope of formula I are: 4-hydroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-bicyclo[3.2.1]oct-3-en- 2-one and 5-hydroxy-4-(4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoyl)-2,6,6- trimethyl-6.H.-[1 ,2]oxazin-3-one.
The compounds of formula I may be produced by known processes which are described, for example, in US-A-5,565,410, US-A-5,608,101 and EP-A-0 282 944, whereby e.g. a compound of formula II
Figure imgf000011_0001
wherein R1 t R2, R3 and X have the significances given under formula I and Z signifies a leaving group, preferably halogen, especially chlorine or cyano, is reacted with a compound of formula III (III), wherein the substituents are defined as in group
Figure imgf000012_0001
Qι, or with a compound of formula IV (IV) , wherein the substituents
Figure imgf000012_0002
are defined as in group Q2, or with a compound of formula V
Figure imgf000012_0003
wherein the substituents are defined as in group Q3, or with a compound of formula VI
(VI), wherein the substituents are defined as in group Q and
Figure imgf000012_0004
correspondingly R39, R23, R27 and R33 signify hydroxy, optionally in the presence of a base. The compounds of formulae II, III, IV or V are known from US-A-5,565,410, US-A-5,608,101 and EP-A-0282 944 or may be produced analogously to the processes disclosed therein.
The reactions for obtaining the compounds of formula I are advantageously carried out in aprotic inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloro- methane, tetrachloromethane or chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles such as acetonitrile or propionitrile, amides such as N,N-dimethyl formamide, diethyl formamide or N-methylpyrrolidinone. The reaction temperatures are preferably in the range from -20° to +120°C. The reactions are usually slightly exothermic and can as a rule be carried out at room temperature. The reaction mixture can be heated for a brief time to boiling point to shorten the reaction time or also to initiate the reaction. The reaction times can also be shortened by addition of a few drops of a base as reaction catalyst. Particularly suitable bases are tertiary amines such as trimethylamine, triethylamine, quinuclidine, 1 ,4- diazabicyclo[2.2.2]octane, 1 ,5-diazabicyclo[4.3.0]non-5-ene or 1 ,5- diazabicyclo[5.4.0]undec-7-ene. Further suitable bases are also inorganic bases, typically hydrides such as sodium or calcium hydride, hydroxides such as sodium or potassium hydroxide, carbonates such as sodium and potassium carbonate, or hydrogen carbonates such as potassium and sodium hydrogen carbonate.
The compounds of formula I can be isolated in conventional manner by concentrating the reaction mixture and/or removing the solvent by evaporation and by recrystallising or triturating the solid residue in solvents in which they are not readily soluble, typically ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
The compounds of formula I or compositions containing them may be used according to this invention by all standard methods of application used in agriculture, including preemergence application, postemergence application and seed dressing, as well as by different methods and techniques such as controlled release. For controlled release, a solution of the herbicide is applied to a mineral granular carrier or to a polymerised granulate (urea/formaldehyde) and then dried. A coating can then be additionally applied (coated granules) that allows the active ingredient to be released at a controlled rate over a specific period of time.
The compounds of formula I may be used as herbicides in unmodified form, i.e. as obtained in the synthesis. Preferably they are processed in conventional manner with the auxiliary agents customarily employed in formulation technology to emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granulates or microcapsules. Such formulations are described, for example, in WO 97/34485 on pages 9 to 13. As with the type of agents, the methods of application such as spraying, atomising, dusting, wetting, scattering or pouring, are selected in accordance with the intended objectives and the prevailing circumstances.
The formulations, i.e. the agents, preparations, or compositions containing the compound of formula I or at least one compound of formula I and usually one or more than one liquid or solid formulation assistant, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the herbicide with said formulation auxiliaries, typically solvents or solid carriers. Surface-active compounds (surfactants) may additionally be used for preparing the formulations. Examples of solvents and solid carriers are described in WO 97/34485 on page 6.
Depending on the herbicide of formula I to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.
Examples of suitable anionic, nonionic, and cationic surfactants are listed for example in WO 97/34485 on pages 7 and 8.
Also the surfactants customary in the art of formulation and described, inter alia, in "McCutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981 , Stache, H., "Tensid-Taschenbuch" (Handbook of Surfactants), Carl Hanser Veriag, Munich/Vienna, 1981 , and M. and J. Ash, "Encyclopedia of Surfactants", Vol l-lll, Chemical Publishing Co., New York, 1980-81 , are suitable for manufacture of the herbicides according to the invention.
The herbicidal compositions will as a rule contain from 0.1 to 99 % by weight, preferably from 0.1 to 95% by weight, of herbicide, from 1 to 99.9% by weight, preferably from 5 to 99.8% by weight, of a solid or liquid adjuvant, and from 0 to 25% by weight, preferably from 0.1 to 25% by weight, of a surfactant. Whereas it is preferred to formulate commercial products as concentrates, the end user will normally use dilute formulations. The compositions may also contain further ingredients, such as: stabilisers, e.g. where appropriate epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil, or soybean oil); anti-foaming agents, typically silicone oil; preservatives; viscosity regulators; binders; and tackifiers; as well as fertilisers or other chemical agents. The compounds of formula I are usually applied with success to the plants or the locus thereof in concentrations of 0.001 to 4 kg/ha, preferably 0.005 to 2 kg/ha. The concentration required to achieve the desired action can be determined by experimentation. It will depend on the type of action, the development stage of the cultivated plant and of the weed, as well as on the application (locus, time, method), and as a resulty of these variables can vary over a wide range.
The compounds of formula I have excellent herbicidal and growth inhibiting properties, which make them suitable for application in crops of cultivated plants, especially in cereals, cotton, soybeans, sugar beet, sugar cane, plantations, rape, maize, and rice, and for the non-selective control of weeds. Crops will also be understood to mean those crops that have been made tolerant to herbicides or classes of herbicides by conventional breeding or genetic engineering methods. The weeds to be controlled may be monocot as well as dicot weeds, typically Stellaria, Nasturtium, Agrostis, Digitaπa, Avena, Setaπa, Sinapis, Lolium, Solanum, Echinochloa, Sciφus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola, and Veronica.
The invention is illustrated by the following non-limitative Examples.
Preparation Examples:
Example P1 : Preparation of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride:
Figure imgf000015_0001
A solution of 1.5 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid in 15 ml of methylene chloride produced in accordance with EP-A-0 282 944 is mixed at a temperature of 20°C with 2 drops of DMF. Then, whilst cooling lightly, a solution of 1.0 ml (11.6 mmols) of oxalyl chloride in 2 ml of methylene chloride is added dropwise. The reaction mixture is stirred until the evolution of gas has ended. Subsequently, the solvent is distilled off. The 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride is used without further purification directly for the next step of the process.
Example P2: Preparation of 4-hvdroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methyl- benzoyπ-bicvclor3.2.1 ]oct-3-en-2-one:
Figure imgf000016_0001
0.8 g (5.8 mmols) of bicyclo[3.2.1]octan-2,4-dione (the preparation thereof is described for example in US-A-5,608,101 and in the references cited therein) are dissolved in 15 ml of methylene chloride at 20°C. The solution is mixed with 0.97 ml of triethylamine and cooled to a temperature of 0°C. Then, a solution of 1.6 g (5.8 mmols) of 4-methylsulphonyl-3- methoxymethyl-2-methyibenzoic acid chloride in 10 ml of methylene chloride is added dropwise. The reaction mixture is stirred for half an hour at a temperature of 0°C and is subsequently diluted with methylene chloride. After washing and drying, the organic phase is concentrated by evaporation. 2.23 g of 4-methylsulphonyl-3-methoxymethyl-2-methyl- benzoic acid-4-oxo-bicyclo[3.2.1]oct-2-en-2-yl-ester is obtained in amorphous form. This can be used for the next step without purification.
2.23 g (5.8 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoic acid-4-oxo- bicyclo[3.2.1]oct-2-en-2-yl-ester and 1.6 ml (11.6 mmols) of triethylamine are dissolved in 20 ml of acetonitrile. 0.2 ml of acetocyanohydrin are added at a temperature of 20°C. After stirring for 20 hours, the mixture is worked up and the crude product is purified by thick- layer chromatography. 1.0 g of 4-hydroxy-3-(4-methylsulphonyl-3-methoxymethyl-2-methyl- benzoyl)-bicyclo[3.2.1]oct-3-en-2-one is obtained in amorphous form.
Example P3: Preparation of 5-hvdroxy-4-(4-methylsulphonyl-3-methoxymethyl-2-methyl- benzovπ-2.6.6-trimethyl-6.H.-n .21oxazin-3-one:
Figure imgf000017_0001
0.79 g (5.04 mmols) of 2,6,6-trimethyl-2H-1 ,2-oxazin-3,5-dione (the preparation thereof is described for example in US-A-5.565.410), 15 ml of methylene chloride and 0.97 ml of triethylamine are prepared, and at a temperature of 0°C, a solution of 1.3 g (4.7 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methylbenzoic acid chloride in 10 ml methylene chloride is added dropwise. After stirring for 30 minutes, the solution is diluted with methylene chloride. The reaction solution is subsequently acidified with diluted hydrochloric acid, the organic phase separated, dried and concentrated. 2.0 g of 4-methyisulphonyl-3- methoxymethyl-2-methyl-benzoic acid-2,6,6-trimethyl-5-oxo-5,6-dihydro-2.H.-[1 ,2]oxazin-3- yl-ester are obtained in amorphous form. The product may be further used directly without purification.
2.0 g (5.04 mmols) of 4-methylsulphonyl-3-methoxymethyl-2-methyl-benzoic acid-2,6,6- trimethyl-5-oxo-5,6-dihydro-2.H.-[1 ,2]oxazin-3-yl-ester are dissolved in a mixture of 35 ml of acetonitrile and 10 ml of methylene chloride, then 1.4 ml (10.08 mmols) of triethylamine and 0.18 ml of acetocyanohydrin are added. After stirring for 20 hours at a temperature of 20°C and then working up, recrystallisation is effected, and finally hydroxy-4-(4-methylsulphonyl- 3-methoxymethyl-2-methyl-benzoyl)-2,6,6-trimethyl-6.H.-[1 ,2]oxazin-3-one is obtained with a melting point of 157°C.
The substances named in the following Tables 1 to 4 may also be prepared analogously to the methods described above. In Tables 1 to 4, X denotes the following groups: Xi = CH2OCH3.X2 = CH2OC2H5, X3 = CH2OH, X, = CH2CH2OCH3, X5 = CH2CH2OC2H5, X6 = CH2CH2OCH2CH2OCH3, X7 = CH2CH2OCH2CH2OC2H5, X8 = CH(CH3)OC2H5, Xι0 = CH2OCH2CH=CH2, X11 = CH2OCH2CH2CH3, Xι2 = CH(C2H5)OC2H5, X13 = C(CH3)2OH, X = CH2CH2OCH(CH3)2, Xis = CH2SO2CH3, Xιe= CH2N(CH3)C2H5, X17 = CH2NHCH3, Xι8 = CH2OCH(CH3)2, X,9 = C(CH3)2OCH3, X20 = CH2CH2OH, X2i = CH2OCH2CCH, X∞ = C(CH3)2OC2H5, X23 = CH(C2H5)OCH3, X24 = CH(CH3)OH, X25 = CH(OH)C2H5, X26 = CH2SCH3, X27 = CH2N(CH3)2, X2Θ = CH2CH2N(CH3)2, X29 = CH2OCOCH3, X30 = CH2OPh, X3, = CH2CH2OPh, X32 = CH2OCH2CH2OCH3, X33 = CH2OCH2CH2OC2H5l
Figure imgf000018_0001
Figure imgf000018_0002
Table 1 : Compounds of formula (la):
Figure imgf000019_0001
Comp. V R17 R^ Ri X R2 Phys
No. data
1,001 CH2 H H CH3 Xi SO2CH3 resin
1,002 CH2 H H CH3 χ2 SO2CH3
1,003 CH2 H H CH3 χ3 SO2CH3
1,004 CH2 H H CH3 X, SO2CH3
1,005 CH2 H H CH3 χ5 SO2CH3
1,006 CH2 H H CH3 χ6 SO2CH3
1,007 CH2 H H CH3 x7 SO2CH3
1,008 CH2 H H CH3 Xβ SO2CH3
1,009 CH2 H H CH3 χ9 SO2CH3
1,010 CH2 H H CH3 X10 SO2CH3
1,011 CH2 H H CH3 X11 SO2CH3
1,012 CH2 H H CH3 Xl2 SO2CH3
1,013 CH2 H H CH3 Xl3 SO2CH3
1,014 CH2 H H CH3 Xι4 SO2CH3 ,015 CH2 H H CH3 Xl5 SO2CH3 ,016 CH2 H H CH3 Xl6 SO2CH3 ,017 CH2 H H CH3 Xl7 SO2CH3 ,018 CH2 H H CH3 Xlβ SO2CH3 ,019 CH2 H H CH3 Xl9 SO2CH3 ,020 CH2 H H CH3 X20 SO2CH3 ,021 CH2 H H CH3 X21 SO2CH3 ,022 CH2 H H CH3 X22 SO2CH3 ,023 CH2 H H CH3 X23 SO2CH3 ,024 CH2 H H CH3 X24 SO2CH3 Comp. V R17 R22 R1 X R2 Phys,
No. data
1,025 CH2 H H CH3 X25 SO2CH3
1,026 CH2 H H CH3 X26 SO2CH3
1,027 CH2 H H CH3 x2 SO2CH3
1,028 CH2 H H CH3 X28 SO2CH3
1,029 CH2 H H CH3 X29 SO2CH3
1,030 CH2 H H CH3 X30 SO2CH3
1,031 CH2 H H CH3 X31 SO2CH3
1,032 CH2 H H CH3 x32 SO2CH3
1,033 CH2 H H CH3 X33 SO2CH3
1,034 CH2 H H CH3 x34 SO2CH3
1,035 CH2 H H CH3 X35 SO2CH3
1,036 CH2 H H CH3 X36 SO2CH3
1,037 CH2 H H CH3 X37 SO2CH3
1,038 CH2 H H CH3 X38 SO2CH3
1,039 CH2 H H CH3 X39 SO2CH3
1,040 CH2 H H CH3 X^ SO2CH3
1,041 CH2 H H CH3 X« SO2CH3 ,042 CH2 H H CH3 X« SO2CH3
Figure imgf000020_0001
,044 CH2 H H CH3 χ2 SCH3
Figure imgf000020_0002
,046 CH2 H H CH3 X, SCH3 ,047 CH2 H H CH3 χ5 SCH3 ,048 CH2 H H CH3 χ6 SCH3 ,049 CH2 H H CH3 χ7 SCH3
Figure imgf000020_0003
,055 CH2 H H CH3 x27 SCH3 Comp. V R17 T 22 Ri x R2 Phys
No. data
Figure imgf000021_0001
1,058 CH3 CH3 CH3 CH3 Xi SO2CH3
1,059 CH3 CH3 CH3 CH3 χ2 SO2CH3
1,060 CH3 CH3 CH3 CH3 X. SO2CH3
1,061 CH3 CH3 CH3 CH3 X10 SO2CH3
1,062 CH3 CH3 CH3 CH3 Xl5 SO2CH3
1,063 CH3 CH3 CH3 CH3 X21 SO2CH3
1,064 CH3 CH3 CH3 CH3 X26 SO2CH3
1,065 O CH3 CH3 CH3 X1 SO2CH3
1,066 O CH3 CH3 CH3 χ2 SO2CH3
1,067 O CH3 CH3 CH3 X. SO2CH3
1,068 O CH3 CH3 CH3 X10 SO2CH3
1,069 O CH3 CH3 CH3 Xl5 SO2CH3
1,070 O CH3 CH3 CH3 X21 SO2CH3
1,071 O CH3 CH3 CH3 X26 SO2CH3
Figure imgf000021_0002
,073 CH2 H H Cl χ2 SO2CH3 ,074 CH2 H H Cl χ3 SO2CH3 ,075 CH2 H H Cl X. SO2CH3 ,076 CH2 H H Cl χ5 SO2CH3 ,077 CH2 H H Cl χ6 SO2CH3
Figure imgf000021_0003
,085 CH2 H H Cl Xι4 SO2CH3
Figure imgf000021_0004
Comp. V R17 R22 R1 X R2 Phys
No. data
1,087 CH2 H H Cl X16 SO2CH3
1,088 CH2 H H Cl Xl7 SO2CH3
1,089 CH2 H H Cl Xιβ SO2CH3
1,090 CH2 H H Cl Xl9 SO2CH3
1,091 CH2 H H Cl X20 SO2CH3
1,092 CH2 H H Cl X21 SO2CH3
1,093 CH2 H H Cl X22 SO2CH3
1,094 CH2 H H Cl X23 SO2CH3
1,095 CH2 H H Cl x24 SO2CH3
1,096 CH2 H H Cl X25 SO2CH3
1,097 CH2 H H Cl X26 SO2CH3
1,098 CH2 H H Cl x2 SO2CH3
Figure imgf000022_0001
,105 CH2 H H Cl X34 SO2CH3
Figure imgf000022_0002
,109 CH2 H H Cl X∞ SO2CH3
Figure imgf000022_0003
,113 CH2 H H Cl χ2 SO2CH3
Figure imgf000022_0004
Comp. V R17 R22 R1 X R2 Phys,
No. data
1 ,118 CH2 H H CH3 χ5 CF3
1 ,119 CH2 H H CH3 χ6 CF3
1 ,120 CH2 H H CH3 χ7 CF3
Figure imgf000023_0001
1 ,124 CH2 H H CH3 X2ι CF3
Figure imgf000023_0002
,126 CH2 H H CH3 x27 CF3
Figure imgf000023_0003
,130 CH2 H H CH3 χ2 Br ,131 CH2 H H CH3 χ3 Br ,132 CH2 H H CH3 X. Br ,133 CH2 H H CH3 χ5 Br ,134 CH2 H H CH3 χ6 Br ,135 CH2 H H CH3 χ7 Br
Figure imgf000023_0004
,141 CH2 H H CH3 x2 Br
Figure imgf000023_0005
,145 CH2 H H CH3 χ2 CN ,146 CH2 H H CH3 χ3 CN ,147 CH2 H H CH3 X CN ,148 CH2 H H CH3 χ6 CN Comp. V R17 ∑2 Ri X R2 Phys,
No. data
Figure imgf000024_0001
1 ,151 CH2 H H CH3 X2ι CN
Figure imgf000024_0002
1 ,154 CH2 H H CF3 X1 SO2CH3
1 ,155 CH2 H H CF3 χ2 SO2CH3
1 ,156 CH2 H H CF3 X3 SO2CH3
1 ,157 CH2 H H CF3 X, SO2CH3
1 ,158 CH2 H H CF3 Xe SO2CH3
1 ,159 CH2 H H CF3 X10 SO2CH3
1 ,160 CH2 H H CF3 Xl5 SO2CH3
1 ,161 CH2 H H CF3 21 SO2CH3
1 ,162 CH2 H H CF3 X26 SO2CH3 ,163 CH2 H H CF3 X30 SO2CH3 ,164 CH3 CH3 CH3 CF3 X1 SO2CH3 ,165 CH3 CH3 CH3 CF3 χ2 SO2CH3 ,166 CH3 CH3 CH3 CF3 X. SO2CH3 ,167 CH3 CH3 CH3 CF3 X10 SO2CH3 ,168 CH3 CH3 CH3 CF3 Xl5 SO2CH3 ,169 CH3 CH3 CH3 CF3 X21 SO2CH3 ,170 CH3 CH3 CH3 CF3 X26 SO2CH3
Figure imgf000024_0003
,172 CH2 H H SO2CH3 χ2 CF3
Figure imgf000024_0004
,174 CH2 H H SO2CH3 χ» CF3 ,175 CH2 H H SO2CH3 Xe CF3 ,176 CH2 H H SO2CH3 X10 CF3 ,177 CH2 H H SO2CH3 Xl5 CF3 ,178 CH2 H H SO2CH3 X21 CF3 ,179 CH2 H H SO2CH3 X26 CF3 Comp. V Rl7 T 2Z Ri X R2 Phys
No. data
1,180 CH2 H H SO2CH3 X30 CF3
Figure imgf000025_0001
1,182 CH2 H H CH3 χ2 Cl
Figure imgf000025_0002
1,184 CH2 H H CH3 X. Cl
1,185 CH2 H H CH3 χ6 Cl
Figure imgf000025_0003
1,191 CH2 H H NO2 X1 SO2CH3
1,192 CH2 H H NO2 χ2 SO2CH3
1,193 CH2 H H NO2 X. SO2CH3
1,194 CH2 H H NO2 X10 SO2CH3
1,195 CH2 H H NO2 Xl5 SO2CH3
1,196 CH2 H H NO2 X21 SO2CH3
1,197 CH2 H H NO2 X26 SO2CH3
Table 2: Compou mds of forrr lula (lb:
Figure imgf000025_0004
Comp. R24 R25 R26 R1 X R2 m.p.
No. (βC)
2,001 CH3 CH3 CH3 CH3 X1 SO2CH3 157°C
2,002 CH3 CH3 CH3 CH3 χ2 SO2CH3 - ,003 CH3 CH3 CH3 CH3 X3 SO2CH3 - Comp. R2 R25 R26 R1 X R2 m.p.
No. (°C)
2,004 CH3 CH3 CH3 CH3 X, SO2CH3
2,005 CH3 CH3 CH3 CH3 χ5 SO2CH3
2,006 CH3 CH3 CH3 CH3 Xe SO2CH3
2,007 CH3 CH3 CH3 CH3 χ7 SO2CH3
2,008 CH3 CH3 CH3 CH3 χ8 SO2CH3
2,009 CH3 CH3 CH3 CH3 X9 SO2CH3
2,010 CH3 CH3 CH3 CH3 X10 SO2CH3
2,011 CH3 CH3 CH3 CH3 X11 SO2CH3
2,012 CH3 CH3 CH3 CH3 X12 SO2CH3
2,013 CH3 CH3 CH3 CH3 Xι3 SO2CH3
2,014 CH3 CH3 CH3 CH3 Xι4 SO2CH3
2,015 CH3 CH3 CH3 CH3 Xl5 SO2CH3 ,016 CH3 CH3 CH3 CH3 X16 SO2CH3 ,017 CH3 CH3 CH3 CH3 Xl7 SO2CH3 ,018 CH3 CH3 CH3 CH3 X18 SO2CH3 ,019 CH3 CH3 CH3 CH3 Xl9 SO2CH3 ,020 CH3 CH3 CH3 CH3 X20 SO2CH3 ,021 CH3 CH3 CH3 CH3 X2ι SO2CH3 ,022 CH3 CH3 CH3 CH3 x22 SO2CH3 ,023 CH3 CH3 CH3 CH3 X23 SO2CH3 ,024 CH3 CH3 CH3 CH3 x24 SO2CH3 ,025 CH3 CH3 CH3 CH3 X25 SO2CH3 ,026 CH3 CH3 CH3 CH3 X∞ SO2CH3 ,027 CH3 CH3 CH3 CH3 x2 SO2CH3 ,028 CH3 CH3 CH3 CH3 X28 SO2CH3 ,029 CH3 CH3 CH3 CH3 X29 SO2CH3 ,030 CH3 CH3 CH3 CH3 XM SO2CH3 ,031 CH3 CH3 CH3 CH3 X31 SO2CH3 ,032 CH3 CH3 CH3 CH3 x32 SO2CH3 ,033 CH3 CH3 CH3 CH3 χ33 SO2CH3 ,034 CH3 CH3 CH3 CH3 XM SO2CH3 Comp. R2 R25 26 R1 X R2 m.p.
No. (°C)
2,035 CH3 CH3 CH3 CH3 X35 SO2CH3
2,036 CH3 CH3 CH3 CH3 XM SO2CH3
2,037 CH3 CH3 CH3 CH3 X37 SO2CH3
2,038 CH3 CH3 CH3 CH3 38 SO2CH3 ,039 CH3 CH3 CH3 CH3 X3g SO2CH3 ,040 CH3 CH3 CH3 CH3 X10 SO2CH3 ,041 CH3 CH3 CH3 CH3 X41 SO2CH3 ,042 CH3 CH3 CH3 CH3 X42 SO2CH3 ,043 CH3 CH3 CH3 Cl X1 SO2CH3 ,044 CH3 CH3 CH3 Cl χ2 SO2CH3 ,045 CH3 CH3 CH3 Cl χ3 SO2CH3 ,046 CH3 CH3 CH3 Cl X, SO2CH3 ,047 CH3 CH3 CH3 Cl χ5 SO2CH3 ,048 CH3 CH3 CH3 Cl Xe SO2CH3 ,049 CH3 CH3 CH3 Cl X7 SO2CH3 ,050 CH3 CH3 CH3 Cl X10 SO2CH3 ,051 CH3 CH3 CH3 Cl Xl5 SO2CH3 ,052 CH3 CH3 CH3 Cl X20 SO2CH3 ,053 CH3 CH3 CH3 Cl X21 SO2CH3 ,054 CH3 CH3 CH3 Cl X26 SO2CH3 ,055 CH3 CH3 CH3 Cl x27 SO2CH3 ,056 CH3 CH3 CH3 Cl X∑9 SO2CH3 ,057 CH3 CH3 CH3 Cl χ∞ SO2CH3 ,058 CH3 CH3 CH3 CH3 X1 SCH3 ,059 CH3 CH3 CH3 CH3 X2 SCH3 ,060 CH3 CH3 CH3 CH3 X3 SCH3 ,061 CH3 CH3 CH3 CH3 A SCH3 ,062 CH3 CH3 CH3 CH3 χ5 SCH3 ,063 CH3 CH3 CH3 CH3 Xe SCH3 ,064 CH3 CH3 CH3 CH3 X7 SCH3 ,065 CH3 CH3 CH3 CH3 X10 SCH3 Comp. R24 R25 R2β Ri X R2 m.p.
No. CO
2,066 CH3 CH3 CH3 CH3 l5 SCH3
2,067 CH3 CH3 CH3 CH3 X∞ SCH3
2,068 CH3 CH3 CH3 CH3 X21 SCH3
2,069 CH3 CH3 CH3 CH3 X∞ SCH3
2,070 CH3 CH3 CH3 CH3 X27 SCH3 ,071 CH3 CH3 CH3 CH3 χ» SCH3 ,072 CH3 CH3 CH3 CH3 X30 SCH3 ,073 H H C2Hs CH3 X1 SO2CH3 ,074 H H C2Hs CH3 χ2 SO2CH3 ,075 H H C2Hδ CH3 X. SO2CH3 ,076 H H C2Hs CH3 X10 SO2CH3 ,077 H H C2Hs CH3 Xl5 SO2CH3 ,078 H H C2Hs CH3 X21 SO2CH3 ,079 H H C2Hs CH3 X26 SO2CH3 ,080 H H C3H CH3 Xi SO2CH3 ,081 H H C3H CH3 χ2 SO2CH3 ,082 H H C3H7 CH3 X SO2CH3 ,083 H H C3H7 CH3 X10 SO2CH3 ,084 H H C3H CH3 Xl5 SO2CH3 ,085 H H CsH7 CH3 X21 SO2CH3 ,086 H H C3H7 CH3 X26 SO2CH3 ,087 CH3 CH3 CH3 Cl X1 SCH3 ,088 CH3 CH3 CH3 Cl χ2 SCH3 ,089 CH3 CH3 CH3 Cl X. SCH3 ,090 CH3 CH3 CH3 Cl X∞ SCH3 ,091 CH3 CH3 CH3 CH3 X1 CF3 ,092 CH3 CH3 CH3 CH3 χ2 CF3 ,093 CH3 CH3 CH3 CH3 X3 CF3 ,094 CH3 CH3 CH3 CH3 X4 CF3 ,095 CH3 CH3 CH3 CH3 Xe CF3 ,096 CH3 CH3 CH3 CH3 X10 CF3 Comp. R24 R25 R26 Ri X R2 m.p.
No. (°C)
2,097 CH3 CH3 CH3 CH3 Xl5 CF3 -
2,098 CH3 CH3 CH3 CH3 X21 CF3 -
2,099 CH3 CH3 CH3 CH3 ∞ CF3 -
2,100 CH3 CH3 CH3 CH3 X30 CF3 -
2,101 CH3 CH3 CH3 SO2CH3 X1 CF3 -
2,102 CH3 CH3 CH3 SO2CH3 χ2 CF3 -
2,103 CH3 CH3 CH3 SO2CH3 X4 CF3 -
2,104 CH3 CH3 CH3 SO2CH3 X26 CF3 -
2,105 CH3 CH3 CH3 NO2 X1 CF3 -
2,106 CH3 CH3 CH3 NO2 χ2 CF3 -
2,107 CH3 CH3 CH3 NO2 X. CF3 -
2,108 CH3 CH3 CH3 NO2 XM CF3 -
2,109 CH3 CH3 CH3 NO2 X1 SO2CH3 -
2,110 CH3 CH3 CH3 NO2 χ2 SO2CH3 -
2,11 1 CH3 CH3 CH3 NO2 X4 SO2CH3 -
2,112 CH3 CH3 CH3 NO2 2B SO2CH3 -
2,113 CH3 CH3 CH3 Br X1 SO2CH3 -
2,114 CH3 CH3 CH3 Br χ2 SO2CH3 -
2,115 CH3 CH3 CH3 Br X. SO2CH3 -
2,1 16 CH3 CH3 CH3 Br X26 SO2CH3 -
Table 3: Compounds of formula (lc):
Comp. >28 129
Figure imgf000029_0001
Phys.
No. data
3,001 CH3 CH3 CHa CH3 X1 SO2CH3 Comp. R28 R∞ R30 Ri X R2 Phys,
No. data
3,002 CH3 CH3 CH3 CH3 χ2 SO2CH3
3,003 CH3 CH3 CH3 CH3 X3 SO2CH3
3,004 CH3 CH3 CH3 CH3 X. SO2CH3
3,005 CH3 CH3 CH3 CH3 χ5 SO2CH3
3,006 CH3 CH3 CH3 CH3 Xβ SO2CH3
3,007 CH3 CH3 CH3 CH3 χ7 SO2CH3
3,008 CH3 CH3 CH3 CH3 χ8 SO2CH3
3,009 CH3 CH3 CH3 CH3 X9 SO2CH3
3,010 CH3 CH3 CH3 CH3 X10 SO2CH3
3,01 1 CH3 CH3 CH3 CH3 X11 SO2CH3
3,012 CH3 CH3 CH3 CH3 Xι2 SO2CH3
3,013 CH3 CH3 CH3 CH3 Xl3 SO2CH3
3,014 CH3 CH3 CH3 CH3 Xl4 SO2CH3
3,015 CH3 CH3 CH3 CH3 Xl5 SO2CH3
3,016 CH3 CH3 CH3 CH3 X16 SO2CH3
3,017 CH3 CH3 CH3 CH3 Xl7 SO2CH3
3,018 CH3 CH3 CH3 CH3 X18 SO2CH3
3,019 CH3 CH3 CH3 CH3 Xl9 SO2CH3
3,020 CH3 CH3 CH3 CH3 X20 SO2CH3
3,021 CH3 CH3 CH3 CH3 X21 SO2CH3
3,022 CH3 CH3 CH3 CH3 Xz. SO2CH3
3,023 CH3 CH3 CH3 CH3 X_α SO2CH3 ,024 CH3 CH3 CH3 CH3 x24 SO2CH3 ,025 CH3 CH3 CH3 CH3 X25 SO2CH3
3,026 CH3 CH3 CH3 CH3 X26 SO2CH3 ,027 CH3 CH3 CH3 CH3 x2 SO2CH3 ,028 CH3 CH3 CH3 CH3 X28 SO2CH3 ,029 CH3 CH3 CH3 CH3 χ» SO2CH3 ,030 CH3 CH3 CH3 CH3 Xβo SO2CH3 ,031 CH3 CH3 CH3 CH3 X31 SO2CH3 ,032 CH3 CH3 CH3 CH3 χ32 SO2CH3 Comp. R28 29 R30 R1 X R2 Phys
No. data
3,033 CH3 CH3 CH3 CH3 XM SO2CH3
3,034 CH3 CH3 CH3 CH3 XM SO2CH3
3,035 CH3 CH3 CH3 CH3 Xs5 SO2CH3
3,036 CH3 CH3 CH3 CH3 X36 SO2CH3
3,037 CH3 CH3 CH3 CH3 X37 SO2CH3
3,038 CH3 CH3 CH3 CH3 X∞ SO2CH3
3,039 CH3 CH3 CH3 CH3 X39 SO2CH3
3,040 CH3 CH3 CH3 CH3 XJO SO2CH3
3,041 CH3 CH3 CH3 CH3 X»1 SO2CH3
3,042 CH3 CH3 CH3 CH3 χ2 SO2CH3
3,043 CH3 CH3 CH3 CH3 X1 SCH3
3,044 CH3 CH3 CH3 CH3 χ2 SCH3
3,045 CH3 CH3 CH3 CH3 X3 SCH3
3,046 CH3 CH3 CH3 CH3 X SCH3
3,047 CH3 CH3 CH3 CH3 χ5 SCH3
3,048 CH3 CH3 CH3 CH3 Xe SCH3
3,049 CH3 CH3 CH3 CH3 χ7 SCH3
3,050 CH3 CH3 CH3 CH3 X10 SCH3 ,051 CH3 CH3 CH3 CH3 Xl5 SCH3 ,052 CH3 CH3 CH3 CH3 X20 SCH3 ,053 CH3 CH3 CH3 CH3 X21 SCH3 ,054 CH3 CH3 CH3 CH3 X26 SCH3 ,055 CH3 CH3 CH3 CH3 x2 SCH3 ,056 CH3 CH3 CH3 CH3 X29 SCH3 ,057 CH3 CH3 CH3 CH3 X30 SCH3 ,058 CH3 CH3 CH3 Cl X1 SO2CH3 ,059 CH3 CH3 CH3 Cl χ2 SO2CH3 ,060 CH3 CH3 CH3 Cl X3 SO2CH3 ,061 CH3 CH3 CH3 Cl X SO2CH3 ,062 CH3 CH3 CH3 Cl χ5 SO2CH3 ,063 CH3 CH3 CH3 Cl Xe SO2CH3 Comp. R28 R29 R30 R1 X R2 Phys
No. data
3,064 CH3 CH3 CH3 Cl χ7 SO2CH3
3,065 CH3 CH3 CH3 Cl Xβ SO2CH3
3,066 CH3 CH3 CH3 Cl χ9 SO2CH3
3,067 CH3 CH3 CH3 Cl X10 SO2CH3
3,068 CH3 CH3 CH3 Cl X11 SO2CH3
3,069 CH3 CH3 CH3 Cl X12 SO2CH3
3,070 CH3 CH3 CH3 Cl Xl3 SO2CH3
3,071 CH3 CH3 CH3 Cl Xι4 SO2CH3
3,072 CH3 CH3 CH3 Cl Xl5 SO2CH3
3,073 CH3 CH3 CH3 Cl X16 SO2CH3
3,074 CH3 CH3 CH3 Cl Xl7 SO2CH3 ,075 CH3 CH3 CH3 Cl X18 SO2CH3 ,076 CH3 CH3 CH3 Cl Xl9 SO2CH3 ,077 CH3 CH3 CH3 Cl X20 SO2CH3 ,078 CH3 CH3 CH3 Cl X21 SO2CH3 ,079 CH3 CH3 CH3 Cl 22 SO2CH3 ,080 CH3 CH3 CH3 Cl X23 SO2CH3 ,081 CH3 CH3 CH3 Cl x24 SO2CH3 ,082 CH3 CH3 CH3 Cl X25 SO2CH3 ,083 CH3 CH3 CH3 Cl X26 SO2CH3 ,084 CH3 CH3 CH3 Cl X27 SO2CH3 ,085 CH3 CH3 CH3 Cl X28 SO2CH3 ,086 CH3 CH3 CH3 Cl X29 SO2CH3 ,087 CH3 CH3 CH3 Cl X3o SO2CH3 ,088 CH3 CH3 CH3 Cl X31 SO2CH3 ,089 CH3 CH3 CH3 Cl X32 SO2CH3 ,090 CH3 CH3 CH3 Cl X33 SO2CH3 ,091 CH3 CH3 CH3 Cl XM SO2CH3 ,092 CH3 CH3 CH3 Cl X35 SO2CH3 ,093 CH3 CH3 CH3 Cl X36 SO2CH3 ,094 CH3 CH3 CH3 Cl X37 SO2CH3 Comp. R2β R29 R30 R1 X R2 Phys.
No. data
3,095 CH3 CH3 CH3 Cl X38 SO2CH3
3,096 CH3 CH3 CH3 Cl X39 SO2CH3
3,097 CH3 CH3 CH3 Cl X^ SO2CH3
3,098 CH3 CH3 CH3 Cl 41 SO2CH3
3,099 CH3 CH3 CH3 Cl χ2 SO2CH3
3,100 CH3 CH3 CH3 CH3 X1 CF3
3,101 CH3 CH3 CH3 CH3 χ2 CF3
3,102 CH3 CH3 CH3 CH3 X3 CF3
3,103 CH3 CH3 CH3 CH3 A CF3 ,104 CH3 CH3 CH3 CH3 Xe CF3 ,105 CH3 CH3 CH3 CH3 X10 CF3 ,106 CH3 CH3 CH3 CH3 Xl5 CF3 ,107 CH3 CH3 CH3 CH3 X21 CF3 ,108 CH3 CH3 CH3 CH3 X26 CF3 ,109 CH3 CH3 CH3 CH3 X30 CF3 ,110 CH3 CH3 CH3 NO2 Xi SO2CH3 ,111 CH3 CH3 CH3 NO2 χ2 SO2CH3 ,112 CH3 CH3 CH3 NO2 X SO2CH3 ,113 CH3 CH3 CH3 NO2 X26 SO2CH3 ,114 CH3 CH3 CH3 NO2 X1 CF3 ,115 CH3 CH3 CH3 NO2 χ2 CF3 ,116 CH3 CH3 CH3 NO2 X CF3 ,117 CH3 CH3 CH3 NO2 X∞ CF3 ,118 CH3 C2Hs CH3 CH3 X1 SO2CH3 ,119 CH3 C2Hs CH3 CH3 χ2 SO2CH3 ,120 CH3 C2Hδ CH3 CH3 X3 SO2CH3 ,121 CH3 C2Hs CH3 CH3 X SO2CH3 ,122 CH3 C2Hs CH3 CH3 Xe SO2CH3 ,123 CH3 C2Hs CH3 CH3 X10 SO2CH3 ,124 CH3 C2Hs CH3 CH3 Xl5 SO2CH3 ,125 CH3 C2Hs CH3 CH3 X21 SO2CH3 Comp. R28 29 R30 R1 X R2 Phys
No. data
3,126 CH3 C2H5 CH3 CH3 χ∞ SO2CH3
3,127 CH3 C2Hs CH3 CH3 X30 SO2CH3
3,128 C2Hs C2Hs CH3 CH3 X1 SO2CH3
3,129 C2Hs C2Hδ CH3 CH3 χ2 SO2CH3
3,130 C2Hs C2Hs CH3 CH3 X SO2CH3
3,131 C2Hs C2Hs CH3 CH3 X10 SO2CH3
3,132 C2Hδ C2Hs CH3 CH3 Xl5 SO2CH3
3,133 C2Hs C2Hs CH3 CH3 X21 SO2CH3
3,134 C2Hs C2Hs CH3 CH3 X26 SO2CH3
3,135 CH3 CH3 CH3 Cl X1 SCH3
3,136 CH3 CH3 CH3 Cl χ2 SCH3
3,137 CH3 CH3 CH3 Cl X3 SCH3
3,138 CH3 CH3 CH3 Cl X SCH3
3,139 CH3 CH3 CH3 Cl Xs SCH3
3,140 CH3 CH3 CH3 Cl Xe SCH3
3,141 CH3 CH3 CH3 Cl X7 SCH3
3,142 CH3 CH3 CH3 Cl X10 SCH3
3,143 CH3 CH3 CH3 Cl Xl5 SCH3
3,144 CH3 CH3 CH3 Cl X20 SCH3
3,145 CH3 CH3 CH3 Cl X21 SCH3
3,146 CH3 CH3 CH3 Cl χ« SCH3
3,147 CH3 CH3 CH3 Cl x2 SCH3
3,148 CH3 CH3 CH3 Cl χ∞ SCH3
3,149 CH3 CH3 CH3 Cl X30 SCH3
Table 4: Compounds of formula 1 (Id):
Figure imgf000034_0001
j*. .p., . *>. .&. *» o o o o o o o o o o o o Z Oo co co o o o o o
-»■ O
Figure imgf000035_0001
eo cn ~J cn en oj>. oco pf ό-i ' 3J
O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O X X X X X X X X X X X X X X X X X X X X X X X X X x x x x x x x s
O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O O x ωx ωx ωx ux ωx ωx ωx wx cxo cxo wx ωx ωx ωx ωx ωx ωx ωx cxo ωx cxo ox ωx cxo cxo ωx ωx cxo cx ux cxo
o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o
o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x x
2 X gX x x x x x x x x x x x x x x x x x x x x x x x x x x x x
X o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o o ox o o o o o o o o o o o o o o o X X X X X X X ωX ωx ωx ωx ωx ωx ωx ω ωx ωx ω X uX ωX X X X X X X X X X X
Q. "0
Comp. Rββ R37 W R1 X R2 Phys
No. data
4,032 CH3 CH3 O CH3 X32 SO2CH3
4,033 CH3 CH3 O CH3 X33 SO2CH3
4,034 CH3 CH3 O CH3 XM SO2CH3
4,035 CH3 CH3 O CH3 X35 SO2CH3
4,036 CH3 CH3 O CH3 X36 SO2CH3
4,037 CH3 CH3 O CH3 X37 SO2CH3
4,038 CH3 CH3 O CH3 X38 SO2CH3
4,039 CH3 CH3 O CH3 X39 SO2CH3
4,040 CH3 CH3 O CH3 XJO SO2CH3
4,041 CH3 CH3 O CH3 Xn SO2CH3
4,042 CH3 CH3 O CH3 x 2 SO2CH3
4,043 CH3 CH3 O CH3 Xi SCH3
4,044 CH3 CH3 O CH3 χ2 SCH3
4,045 CH3 CH3 O CH3 X3 SCH3
4,046 CH3 CH3 O CH3 X. SCH3
4,047 CH3 CH3 O CH3 χ5 SCH3 ,048 CH3 CH3 O CH3 Xe SCH3 ,049 CH3 CH3 O CH3 χ7 SCH3 ,050 CH3 CH3 O CH3 X10 SCH3 ,051 CH3 CH3 O CH3 Xl5 SCH3 ,052 CH3 CH3 O CH3 X∞ SCH3 ,053 CH3 CH3 O CH3 X21 SCH3 ,054 CH3 CH3 O CH3 X26 SCH3 ,055 CH3 CH3 O CH3 X27 SCH3 ,056 CH3 CH3 O CH3 χ∞ SCH3 ,057 CH3 CH3 O CH3 X30 SCH3 ,058 CH3 CH3 O Cl Xi SO2CH3 ,059 CH3 CH3 O Cl χ2 SO2CH3 ,060 CH3 CH3 O Cl X3 SO2CH3 ,061 CH3 CH3 O Cl X, SO2CH3 ,062 CH3 CH3 O Cl Xs SO2CH3 Comp. R∞ R37 W R1 X R2 Phys
No. data
4,063 CH3 CH3 O Cl Xe SO2CH3
4,064 CH3 CH3 O Cl X7 SO2CH3
4,065 CH3 CH3 O Cl χ8 SO2CH3
4,066 CH3 CH3 O Cl χ9 SO2CH3
4,067 CH3 CH3 O Cl X10 SO2CH3
4,068 CH3 CH3 O Cl X11 SO2CH3
4,069 CH3 CH3 O Cl Xι2 SO2CH3
4,070 CH3 CH3 O Cl Xl3 SO2CH3
4,071 CH3 CH3 O Cl Xι4 SO2CH3
4,072 CH3 CH3 O Cl Xl5 SO2CH3
4,073 CH3 CH3 O Cl X16 SO2CH3
4,074 CH3 CH3 O Cl Xl7 SO2CH3
4,075 CH3 CH3 O Cl X18 SO2CH3
4,076 CH3 CH3 O Cl Xl9 SO2CH3 ,077 CH3 CH3 O Cl X20 SO2CH3 ,078 CH3 CH3 O Cl X21 SO2CH3 ,079 CH3 CH3 O Cl 22 SO2CH3 ,080 CH3 CH3 O Cl X23 SO2CH3 ,081 CH3 CH3 O Cl x24 SO2CH3 ,082 CH3 CH3 O Cl X25 SO2CH3 ,083 CH3 CH3 O Cl χ∞ SO2CH3 ,084 CH3 CH3 O Cl X27 SO2CH3 ,085 CH3 CH3 O Cl X28 SO2CH3 ,086 CH3 CH3 O Cl X29 SO2CH3 ,087 CH3 CH3 O Cl X30 SO2CH3 ,088 CH3 CH3 O Cl X31 SO2CH3 ,089 CH3 CH3 O Cl X32 SO2CH3 ,090 CH3 CH3 O Cl X33 SO2CH3 ,091 CH3 CH3 O Cl X34 SO2CH3 ,092 CH3 CH3 O Cl X35 SO2CH3 ,093 CH3 CH3 O Cl X36 SO2CH3 Comp. R3β R37 W Ri X R2 Phys,
No. data
4,094 CH3 CH3 O Cl X37 SO2CH3
4,095 CH3 CH3 O Cl X38 SO2CH3
4,096 CH3 CH3 O Cl X39 SO2CH3
4,097 CH3 CH3 O Cl Xrø SO2CH3
4,098 CH3 CH3 O Cl X»1 SO2CH3
4,099 CH3 CH3 O Cl X»2 SO2CH3
Figure imgf000038_0001
4,101 CH3 CH3 O CH3 χ2 CF3
Figure imgf000038_0002
4,104 CH3 CH3 O CH3 Xe CF3
4,105 CH3 CH3 O CH3 X10 CF3
4,106 CH3 CH3 O CH3 Xl5 CF3
4,107 CH3 CH3 O CH3 X21 CF3
4,108 CH3 CH3 O CH3 X26 CF3
Figure imgf000038_0003
,110 CH3 CH3 O NO2 Xi SO2CH3 ,111 CH3 CH3 O NO2 χ2 SO2CH3 ,112 CH3 CH3 O NO2 X. SO2CH3 ,113 CH3 CH3 O NO2 X26 SO2CH3
Figure imgf000038_0004
,115 CH3 CH3 O NO2 χ2 CF3 ,116 CH3 CH3 O NO2 X. CF3 ,117 CH3 CH3 O NO2 X∞ CF3 ,118 CH3 C2Hs O CH3 XI SO2CH3 ,119 CH3 C2Hδ O CH3 X2 SO2CH3 ,120 CH3 C2Hs O CH3 χ3 SO2CH3 ,121 CH3 C2Hδ O CH3 X. SO2CH3 ,122 CH3 C2Hδ O CH3 Xe SO2CH3 ,123 CH3 C2Hs O CH3 X10 SO2CH3 ,124 CH3 C2Hs O CH3 Xl5 SO2CH3 ^ -^ 4^ ^ ^ 4^ ^ ^ ^ ^ ^ ^ ^ ^ ^ ^- ^ 4*. -F>> 4*- -P>- -&• zo oo cn c c cn cn c -Pk 4^ .^ 4^ ^ 4^ 4 4 4^ c co co c co c co c c co ro i ro r r cn 4 co to ^ o co c» ^j cn cn 4^ co r>o ->- o co co -vi cn cn 4i» co f\3 --k O co oo --4 cn cn 3
o o o o o o o o o o o o o o o o o o o o o p p p p o o o X c Xo cXo cXo uX cXo cXo cXo cXo cXo cX cXo cX cXo cXo cXo cXo cXo cX cXo cXo cXo ' -Ti- ' -*- — T -J- *TJ-- T — >• T J- cXo cXo cXo
o o o o o o o o o o o o o o o o o o o o o p p p p p p p p p p X c Xo cXo cXo tXo cXo cXo cXo cXo cXo cXo cXo cXo cXo cXo cXo cXo tXo cXo cXo cXo cXo T — *-•» X «x- X X ■*» -*• -*• — ■■ X •*—
CΛ C/J CΛ O W CΛ O O O O O O O O O O O O O O O O O O O O O O O O O
o - o— oχ oχ oι oχ o— o- o- o— o— o— o- o- o— o— o— o— o- o— o— oX oX oX oX oX oX oX oX oX oX
Figure imgf000039_0001
x cxfi x x x ox <xδ "x-j x> -x* ox σxι θx x x x x x x x x x x x x x x x x x
(n o) (o tn w w co M W Co to t/) W C/) w cfl cn (/i w co » tn w w w cn cn w to w to o t Xo o X
Figure imgf000039_0002
Q. TJ
0) _y
CO CO
Comp. R36 R37 W Ri X R2 Phys
No. data
4,156 CH3 CH3 S Cl χ> SO2CH3 -
4,157 CH3 CH3 S Cl Xα SO2CH3 -
4,158 CH3 CH3 NCH3 CH3 XI SO2CH3 -
4,159 CH3 CH3 NCH3 CH3 χ2 SO2CH3 -
4,160 CH3 CH3 NCH3 CH3 X, SO2CH3 -
4,161 CH3 CH3 NCH3 CH3 X26 SO2CH3 -
Figure imgf000040_0001
4,163 H H O CH3 χ2 SO2CH3 -
4,164 H H O CH3 X. SO2CH3 -
4,165 H H O CH3 X26 SO2CH3 -
Bioloαical Examples
Example B1 : Prø' -emerαent herbicidal action
Monocot and dicot test plants are sown in standard soil in plastic pots. Immediately after sowing, the plants are sprayed at a concentration of 2 kg active substance/ha with an aqueous suspension of the test compound [prepared from a 25% wettable powder (Example F3, b) in accordance with WO 97/34485] or an emulsion of the test compound [prepared from a 25% emulsifiable concentrate (Example F1 c)] (500 I of water/ha). The test plants are then cultivated in the greenhouse under optimum conditions. The test is evaluated 3 weeks later on a rating scale of 1-9 (1 = total damage, 9 = no action). Ratings of 1 to 4 (especially of 1 to 3) denote good to very good herbicidal action.
Table B1 : Pre-emergent action:
test plant Setaria Cyperus Sinapsis Solanig Stellaria dosage [g AS/ha]
Active ingredient
No.
1,001 3 3 3 2 2 2000
2,001 3 3 2 2 2 2000 The same results are obtained by formulating the compounds of formula I in accordance with Examples F2 and F4 to F8 of WO 97/34485.
Example B2: Post-emerαent herbicidal action
In a greenhouse, monocot and dicot test plants are sown in standard soil in plastic pots and sprayed in the 4- to 6-leaf stage with an aqueous suspension of the test compounds of formula I prepared from a 25 % wettable powder [Example F3, b) of WO 97/34485] or with an emulsion of the test compound of formula I prepared from a 25 % emulsifiable concentrate [Example F1 c) of WO 97/34485] at a concentration of 2 kg active substance/ha (500 I of water/ha). The test plants are then further cultivated in the greenhouse under optimum conditions. The test is evaluated about 18 days later on a rating scale of 1-9 (1 = total damage, 9 = no action). Ratings of 1 to 4 (especially of 1 to 3) denote good to very good herbicidal action. In this test the compounds of formula I exhibit a pronounced herbicidal action.
Table B2: Post-emergent action test plant Setaria Cyperus Sinapsis Solanig Stellaria dosage [g AS/ha]
Active ingredient
No.
1,001 2 3 2 2 2 2000
2,001 3 3 2 2 4 2000
The same results are obtained by formulating the compounds of formula I in accordance with Examples F2 and F4 to F8 of WO 97/34485.

Claims

Patent Claims:
1. Compounds of formula
Figure imgf000043_0001
wherein
X is Lι-Y,-FU , L2-Y2-L3-Y3-R5 or
Figure imgf000043_0002
Li ,L2, L3, , U, , independently of one another, signify Cι-C6-alkylene, which may be substituted by Cι-C4-alkyl, halogen, Cι-C4-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl; or C3-C6-alkenylene, which may be substituted by Cι-C -alkyl, halogen, Cι-C -alkoxy, C2-C6- alkenyl or C2-C6-alkynyl; or C3-C6-alkynylene, which may be substituted by Cι-C -alkyl, halogen, Cι-C4-alkoxy, C2-C6-alkenyl or C2-C6-alkynyl;
Yι, Y3, Ye, independently of one another, signify oxygen, sulphur, SO, SO2, NR7, OC(O), NR8SO2or OSO2;
Y2, Y4. Y5, independently of one another, signify oxygen, sulphur, SO, SO2, NR9, OC(O) or
R7, Rβ> R9 and R , independently of one another, signify hydrogen or Ci-Ce-alkyl; R1 and R2, independently of one another, signify halogen, cyano, nitro, amino, Ci-Ce-alkyl, Ci-Ce-alkoxy, CrC -alkoxy-Cι-C4-alkyl, Cι-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Ce-alkoxycarbonyl, Cι-C6-alkylcarbonyl, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce- alkylsulphonyl, Ci-Ce-dialkylaminosulphonyl, Cι-C6-alkylaminosulphonyl, Cι-C - alkylsulphonylamino, Ci-Ce-halogenalkoxy, OSO2-Cι-C4-alkyl, Ci-Ce-halogenalkylthio, C C6- halogenalkylsulphinyl, Cι-C6-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl;
R3 signifies hydrogen, Cι-C4-alkyl or halogen;
R4, R5 and R6, independently of one another, signify hydrogen, CrC6-alkyl, which may be substituted by the group A1; C3-C7-cycloalkyl, which may be substituted by the group A2; C3-C7-cycloalkyl, which may be interrupted by 1 to 2 oxygen atoms, sulphur or NRn; C2-C6- alkenyl, which may be substituted by the group A3; C3-C6-alkynyl, which may be substituted by the group A,; C3-C7-cycloalkyl-C C4-alkyl, whereby the cycloalkyl group may be interrupted by 1 to 2 oxygen atoms, sulphur or NR 2; benzyl or phenyl which may in turn be substituted by halogen, Cι-C4-alkyl, CrC -alkoxy, Cι-C -halogenalkyl, cyano, nitro, Cι-C4- halogenalkoxy, CrC -alkylthio, Cι-C4-alkylsulphinyl, Cι-C -alkylsulphonyl, Cι-C - dialkylamino, Cι-C4-alkylcarbonyl, CrC4-dialkylaminosulphonyl or NRι3-CO-Rι4 ; Rn and Rι2, independently of one another, signify hydrogen or d-C -alkyl; R13 and Rι , independently of one another, signify hydrogen or d-C -Alkyl; Aι, A2, A3, t, independently of one another, are hydroxy, formyl, COOH, Cι-C6-alkoxy, CrC4-alkylthio, Cι-C4-alkylsulphinyl, d-C4-alkylsulphonyl, OSO2-Cι-C4-alkyl, d-C6- alkylamino, Ci-Ce-dialkylamino, Ci-C6-alkylaminocarbonyl, Ci-Ce-dialkylaminocarbonyl, nitro, halogen, cyano, CrC4-alkoxyhalogen, CrC4-alkylcarbonyl, d-C4-alkoxycarbonyl or phenyl, whereby the phenyl group may in turn be substituted by halogen, C C4-alkyl, C C4-alkoxy, Cι-C4-halogenalkyl, cyano, nitro, CrC -halogenalkoxy, Cι-C4-alkylthio, CrC4-alkylsulphinyl, Cι-C4-alkylsulphonyl, Cι-C4-alkylcarbonyl, CrC4-dialkylaminosulphonyl or NRι5-CO-Rι6; Ri5 and Rι6, independently of one another, signify hydrogen or d-C4-alkyl; Q is the group Qι
Figure imgf000044_0001
wherein R39 signifies hydroxy, halogen, Cι-C6-alkoxy, Cι-C6-alkylcarbonyloxy, Ci-Ce-alkoxy- carbonyloxy, Ci-Ce-dialkylamino, COOH, Ci-Ce-alkenylthio, Cι-C6-alkenylsulphinyl, d-C6- alkenylsulphonyl, OSO2-Cι-C6-alkyl, benzoyioxy or OSO2-phenyl, whereby the phenyl and benzoyl groups may in tum be substituted by CrC4-alkyl, Cι-C -halogenalkyl, d-C -alkoxy, Cι-C -halogenalkoxy, Cι-C -alkylcarbonyl, Cι-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano;V is Cι-C4-alkylene, oxygen, sulphur, SO or SO2;
R17. i8, Ri9, 20 , R21 and R^, independently of one another, signify hydrogen, Ci-Ce-alkyl, Ci-Ce-alkoxycarbonyl, C2-C6-alkenyl, C2-C6-alkynyl, CrC6-alkylthio, Ci-Ce-alkylsulphinyl, CrCe-alkylsulphonyl, C C4-alkylaminosulphonyl, Cι-C4-halogenalkyl, Cι-C4-alkylamino, Cι- C4-dialkylamino, Ci-Ce-alkoxy, cyano, nitro, halogen or phenyl, q is 1 or 2; or Q is the group Q2
Figure imgf000045_0001
wherein
R23 signifies hydroxy, halogen, Cι-C6-alkoxy, Ci-Ce-alkylcarbonyloxy, Cι-C6-alkoxy- carbonyloxy, Ci-Ce-dialkylamino, COOH, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce- alkylsulphonyl, Cι-C4-alkoxycarbonyl-Cι-C -alkylthio, Cι-C -alkoxycarbonyl-Cι-C - alkylsulphinyl, Cι-C4-alkoxycarbonyl-Cι-C4-alkylsulphonyl, Ci-Ce-alkenylthio, d-C6- alkenylsulphinyl, CrC6-alkenylsulphonyl, OSO2-d-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in tum be substituted by Cι-C -alkyl, Cι-C -halogenalkyl, Cι-C4-alkoxy, Cι-C4- halogenalkoxy, Cι-C -alkylcarbonyl, Cι-C -alkoxycarbonyl, halogen, nitro, COOH or cyano; R24 and R25, independently of one another, signify hydrogen, hydroxy, Ci-Ce-alkyl, Cι-C - alkoxy-Cι-C -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxycarbonyl, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce-alkylsulphonyl, Cι-C4-alkylaminosulphonyl, Cι-C -halogenalkyl, Ci-Ce-alkylamino, Ci-Ce-dialkylamino, Ci-Ce-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by d-C4-alkyl, Cι-C -halogenalkyl, Cι-C -alkoxy, d-C - halogenalkoxy, d-C4-alkylcarbonyl, Cι-C -alkoxycarbonyl, amino, d-C4-alkylamino, d-C - dialkylamino, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce-alkylsulphonyl, C C4-alkyl-S(O)2O, Cι-C4-halogenalkylthio, Cι-C -halogenalkylsulphinyl, Cι-C4-halogenalkylsulphonyl, Cι-C4- halogenalkyl-S(O)2O, Cι-C4-alkyl-S(O)2NH, Cι-C4-alkyl-S(O)2N(C C4-alkyl), halogen, nitro, COOH or cyano; or R24 and R25 together form a C2-C6-alkylene bridge, R26 signifies hydrogen, d-C4-alkyl, Cι-C4-alkoxycarbonyl or phenyl, which may in turn be substituted by d-C6-alkyl, Cι-C6-haiogenalkyl, Ci-Ce-alkoxy, Ci-Ce-halogenalkoxy, Ci-Ce- alkylcarbonyl, Ci-Ce-alkoxycarbonyl, amino, Cι-C4-alkylamino, Cι-C4-dialkylamino, Ci-Ce- alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce-alkylsulphonyl, d-C4-alkyl-S(O)2O, Cι-C -halogen- alkylthio, d-C4-halogenalkylsulphinyl, Cι-C -halogenalkylsulphonyl, d-C -halogenalkyl- S(O)2O, Cι-C4-alkyl-S(O)2NH, Cι-C4-alkyl-S(O)2N(Cι-C4-alkyl), halogen, nitro, COOH or cyano; or Q is the group Q3
Figure imgf000046_0001
wherein
R27 signifies hydroxy, halogen, Ci-Ce-alkoxy, d-Ce-alkylcarbonyloxy, d-C6-alkoxy- carbonyloxy, Ci-Ce-dialkylamino, COOH, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce- alkylsulphonyl, Cι-C -alkoxycarbonyl-Cι-C -alkylthio, Cι-C4-alkoxycarbonyl-Cι-C -alkyl- sulphinyl, Cι-C4-alkoxycarbonyl-Cι-C4-alkylsulphonyl, Ci-Ce-alkenylthio, Ci-Ce-alkenyl- sulphinyl, Ci-Ce-alkenylsulphonyl, OSO2-C1-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by Cι-C4-alkyl, d-C -halogenalkyl, Cι-C4-alkoxy, Cι-C4-halogen- alkoxy, Cι-C4-alkylcarbonyl, Cι-C -alkoxycarbonyl, halogen, nitro, COOH or cyano; R28, R29 and R40, independently of one another, signify hydrogen, hydroxy, Ci-Ce-alkyl, Cι-C -alkoxy-Cι-C -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Ce-alkoxycarbonyl, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce-alkylsulphonyl, Cι-C -alkylaminosulphonyl, Cι-C4-halogenalkyl, Ci-Ce-alkylamino, Ci-Ce-dialkylamino, Ci-Ce-alkoxy, cyano, nitro, halogen or phenyl, which may in tum be substituted by Cι-C -alkyl, Cι-C4-halogenalkyl( C C4-alkoxy, d-C4-halogen- alkoxy, Cι-C -alkylcarbonyl, C C4-alkoxycarbonyl, amino, d-C -alkylamino, d-C4-dialkyl- amino, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, d-Ce-alkylsulphonyl, d-C -alkyl-S(O)2O, d-C4- halogenalkylthio, Cι-C4-halogenalkylsulphinyl, Cι-C -halogenalkylsulphonyl, Cι-C -halogen- alkyl-S(O)2O, C C4-alkyl-S(O)2NH, Cι-C4-alkyi-S(O)2N(CrC4-alkyl), halogen, nitro, COOH or cyano; or R28 and R29 together form a C2-C6-alkylene bridge,
R30 signifies Ci-Ce-alkyl, which may be substituted by a group A5; C2-C6-alkenyl, which may be substituted by a group A6; C2-C6-alkynyl, which may be substituted by a group A7; A5, A6 and A7, independently of one another, are hydroxy, formyl, COOH, Ci-Ce-alkoxy, Cι-C4-alkylthio, C C4-alkylsulphinyl, d-C -alkylsulphonyl, OSO2-C C4-alkyl, d-C6- alkylamino, Ci-Ce-dialkylamino, Ci-Ce-alkylaminocarbonyl, Ci-Ce-dialkylaminocarbonyl, nitro, halogen, cyano, Cι-C -alkoxyhalogen, Cι-C4-alkylcarbonyl, d-C -alkoxycarbonyl or phenyl, whereby the phenyl is in turn substituted by halogen, d-C -alkyl, d-C4-alkoxy, Cι-C4- halogenalkyl, cyano, nitro, Cι-C -halogenalkoxy, d-C4-alkylthio, d-C4-alkylsulphinyl, Cι-C4- alkylsulphonyl, d-C4-alkylcarbonyl, Cι-C4-dialkylaminosulphonyl or NR3ι-CO-R32; R31. R32. independently of one another, signify hydrogen or Cι-C4-alkyl; or Q is the group CU
Figure imgf000047_0001
wherein
R33 signifies hydroxy, halogen, Ci-Ce-alkoxy, Cι-C6-alkylcarbonyloxy, Ci-Ce-alkoxy- carbonyloxy, Ci-Ce-dialkylamino, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce-alkylsulphonyl, Cι-C -alkoxycarbonyl-Cι-C -alkylthio, Cι-C4-alkoxycarbonyl-Cι-C -alkylsulphinyl, Cι-C4- alkoxycarbonyl-Cι-C4-alkylsulphonyl, d-Ce-alkenylthio, Ci-Ce-alkenylsulphinyl, d-C6- alkenylsulphonyl, OSO2-d-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSOrphenyl, whereby the phenyl and benzoyl groups may in turn be substituted by C -C -alkyl, Cι-C -haiogenalkyl, Cι-C4-alkoxy, Cι-C4-halogenalkoxy, Cι-C4- alkylcarbonyl, CrC4-alkoxycarbonyl, halogen, nitro, COOH or cyano; W is oxygen, sulphur, SO, SO2, NR3β or C=O; R38 signifies hydrogen or Ci-Ce-alkyl;
R34, R35, 36 and R37, independently of one another, signify hydrogen, hydroxy, Ci-Ce-alkyl, Cι-C4-alkoxy-Cι-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C Ce-alkoxycarbonyl, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce-alkylsulphonyl, Cι-C4-alkylaminosulphonyl, d-C4-halogenalkyl, Ci-Ce-alkylamino, Ci-Ce-dialkylamino, Ci-Ce-alkoxy, cyano, nitro, halogen or phenyl, which may in turn be substituted by d-C -alkyl, Cι-C -haiogenalkyl, Cι-C4-alkoxy, CrC4-halogen- alkoxy, Cι-C4-alkylcarbonyl, d-C4-alkoxycarbonyl, amino, Cι-C4-alkylamino, Cι-C4-dialkyl- amino, d-C6-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce-alkylsulphonyl, d-C4-alkyl-S(O)2O, Cι-C4- halogenalkylthio, Cι-C4-halogenalkylsulphinyl, Cι-C4-halogenalkylsulphonyl, C C4-halogen- alkyi-S(O)2O, CrC4-alkyl-S(O)2NH, Cι-C4-alkyl-S(O)2N(C C4-alkyl), halogen, nitro, COOH or cyano; or R3 and R35 together form a C2-C6-alkylene bridge, as well as agronomically acceptable salts, isomers and enantiomers of these compounds.
2. Compounds according to 1 , whereby
R1 and R2, independently of one another, signify halogen, cyano, nitro, amino, Ci-Ce-alkyl,
Ci-Ce-alkoxy, Cι-C -alkoxy-d-C4-alkyl, Ci-Ce-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, d- Ce-alkoxycarbonyl, Cι-C6-alkylcarbonyl, Ci-Ce-alkylthio, Ci-C6-alkylsulphinyl, Ci-Ce- alkylsulphonyl, Ci-Ce-dialkylaminosulphonyl, Ci-Ce-alkylaminosulphonyl, d-C6- halogenalkoxy, OSO2-d-C -alkyl, Ci-Ce-halogenalkylthio, Cι-C6-halogen-alkylsulphinyl, d- Ce-halogenalkylsulphonyl, phenylthio, phenylsulphinyl or phenylsulphonyl and R33 signifies hydroxy, halogen, Cι-C6-alkoxy, Ci-Ce-alkylcarbonyloxy, Ci-Ce-alkoxy- carbonyloxy, Ci-Ce-dialkylamino, COOH, Ci-Ce-alkylthio, Ci-Ce-alkylsulphinyl, Ci-Ce- alkylsulphonyl, Cι-C4-alkoxycarbonyl-Cι-C4-alkylthio, Cι-C4-alkoxycarbonyl-Cι-C - alkylsulphinyl, CrC4-alkoxycarbonyl-Cι-C4-alkylsulphonyl, Ci-Ce-alkenylthio, d-C6- alkenylsulphinyl, Ci-Ce-alkenylsulphonyl, OSO2-d-C6-alkyl, benzoyloxy, phenylthio, phenylsulphinyl, phenylsulphonyl or OSO2-phenyl, whereby the phenyl and benzoyl groups may in turn be substituted by d-C -alkyl, Cι-C4-haiogenalkyl, Cι-C -alkoxy, Cι-C4- halogenalkoxy, Cι-C4-alkylcarbonyl, Cι-C4-alkoxycarbonyl, halogen, nitro, COOH or cyano.
3. Compounds according to claim 1 , whereby Q is Qι or Q2.
4. Compounds according to claim 1 , whereby X is Li-Y FU.
5. Compounds according to claim 4, whereby Li signifies methylene.
6. Compounds according to claim 1 , whereby R2 signifies Ci-Ce-alkylsulphonyl.
7. A herbicidal and plant growth inhibiting composition, which comprises a herbicidally effective amount of the compound of formula I on an inert carrier.
8. A method of controlling undesirable plant growth, which comprises treating the plants or the locus thereof with a herbicidally effective amount of a compound of formula I or of a composition containing such a compound.
9. A method of inhibiting undesirable plant growth, which comprises treating the plants or the locus thereof with a herbicidally effective amount of a compound of formula I or of a composition containing such a compound.
10. Use of a composition according to claim 7 for controlling undesirable plant growth.
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US20030236167A1 (en) 2003-12-25
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ATE334961T1 (en) 2006-08-15
US6599861B2 (en) 2003-07-29
CN1331675A (en) 2002-01-16
CN100386313C (en) 2008-05-07
DE69932628D1 (en) 2006-09-14
AU1982600A (en) 2000-07-12
US7265230B2 (en) 2007-09-04
BR9916396A (en) 2001-09-11
US20070265165A1 (en) 2007-11-15
EP1140811B1 (en) 2006-08-02
US20020165096A1 (en) 2002-11-07

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