WO2001066522A1 - Acylated phenyl or pyridine herbicides - Google Patents

Acylated phenyl or pyridine herbicides Download PDF

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WO2001066522A1
WO2001066522A1 PCT/EP2001/002581 EP0102581W WO0166522A1 WO 2001066522 A1 WO2001066522 A1 WO 2001066522A1 EP 0102581 W EP0102581 W EP 0102581W WO 0166522 A1 WO0166522 A1 WO 0166522A1
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alkyl
haloalkyl
alkoxy
phenyl
cyano
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PCT/EP2001/002581
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French (fr)
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Christoph Lüthy
Jürgen Schaetzer
Andrew Edmunds
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Syngenta Participations Ag
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Priority to AU2001242451A priority Critical patent/AU2001242451A1/en
Publication of WO2001066522A1 publication Critical patent/WO2001066522A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon 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
    • A01N43/34—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/07—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
    • C07C2602/44—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing eight carbon atoms

Definitions

  • the present invention relates to novel, herbicidally active benzoyl derivatives, to a process for their preparation, to compositions comprising those compounds, and to their use in controlling weeds, especially in crops of useful plants, or in inhibiting plant growth.
  • Benzoyl derivatives having herbicidal action are described, for example, in WO 97/08164, WO 99/09023 and EP-A-0 249 813. Novel benzoyl derivatives having herbicidal and growth- inhibiting properties have now been found.
  • the present invention accordingly relates to compounds of formula I
  • each R is independently hydrogen, C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 2 -C 6 -alkynyl, C 2 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, d-C 6 alkoxy, C ⁇ -C 6 haloalkoxy, C ⁇ -C 6 alkylthio, CrC 6 alkylsulfinyl, d-Cealkylsulfonyl, C C 6 haloalkyl, C ⁇ -C 6 haloalkylthio, C C 6 haloalkyl- sulfinyl, C C 6 haloalkylsulfonyl, C ⁇ -C 6 alkoxycarbonyl, C C 6 alkylcarbonyl, d-C 6 alky
  • Ri, R 3 and R 5 are each independently of the others hydrogen or C C 6 alkyl, R 2 ⁇ s NR 13 Ru, C C 6 alkyl, d-C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl or phenyl, wherein phenyl may itself be substituted by C ⁇ -C 3 alkyl, d-C 3 haloalkyl, d-C 3 alkoxy, d-C 3 haloalkoxy, halogen, cyano or by nitro, R 4 is NR 15 Rie, d-C 6 alkyl, d-C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, C 3 -C 6 alkynyl,
  • R 8 , Rn, R 13 , R 15 and R 17 are each independently of the others d-C 12 alkyl;
  • R 9 , R 12 , R 14 , R 16 and R 8 are each independently of the others d-C 12 alkyl, or R 8 and R 9 together, and/or Rn and R 12 together, and/or R 13 and R 14 together, and/or R 15 and R 16 together, and/or R 17 and R 8 together, with the nitrogen atom to which they are bonded, form a 3- to 7-membered ring;
  • Q is the group Q ⁇
  • R 19 is hydrogen or d-C 6 alkyl
  • R 20 is d-C ⁇ alkyl, d-C ⁇ 2 haloalkyl, C 2 -C ⁇ 2 alkenyl, C 2 -C 6 haloalkenyl, C ⁇ -C 2 alkoxycarbonyl- or phenyl-substituted vinyl, or is C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 allenyl, C 3 -C 6 cycloalkyl,
  • benzyl or phenyl wherein the phenyl-containing groups may themselves be substituted by C C 3 alkyl, C ⁇ -C 3 - haloalkyl, d-C 3 alkoxy, C C 3 haloalkoxy, halogen, cyano or by nitro, or R 20 is hydroxy- d-C 12 alkyl, d-C 4 alkoxy-C ⁇ -C ⁇ 2 alkyl, d-C 4 alkylthio-d-C 12 alkyl, d-dalkylsulfinyl-d-d ⁇ r alkyl, d-C 4 alkylsulfonyl-C ⁇ -C ⁇ 2 alkyl, cyano-CrC ⁇ alkyl, d-C-ealkylcarbonyloxy-d-C ⁇ alkyl,
  • R 20 ⁇ s a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the -N(R ⁇ 9 )-S(0) 2 - group by way of a C ⁇ -C 12 alkylene group, and each ring system may contain no more than two oxygen
  • W is oxygen, sulfur, sulfinyl, sulfonyl, -CR 25 , R 26 -, -C(O)-, -CR 28 R 29 -CR 30 R 3 i- or -NR 27 , wherein the carbon atom carrying the substituents R 28 R 29 is attached to the carbon atom carrying the substituents R 22 R 23 ;
  • R 25 is hydrogen, C C 4 alkyl, C C 4 haloalkyl, C 1 -C alkoxy-C ⁇ -C 4 alkyl, C ⁇ -C alkylthio-d-C - alkyl, C C alkylthio-C 3 -C 6 cycloalkyl, C ⁇ -C 4 alkylcarbonyloxy-C ⁇ -C 4 alkyl ( d-C alkylsulfonyl- oxy-C C alkyl, tosyloxy-C ⁇ -C alkyl, di(d-C 3 alkoxyalkyl)methyl, di(d-C 3 alkylthioalkyl)- methyl, (C 1 -C 3 alkoxyalkyl)-(C 1 -C 3 alkylth ⁇ oalkyl)methyl, C 3 -C 5 oxacycloalkyl, C 3 -C 5 th ⁇ acyclo- alkyl, C 3 -C 4 d ⁇ oxacyclo
  • R 26 is hydrogen, d-C alkyl or C ⁇ -C 4 haloalkyl, or R 26 together with R 25 denotes C 2 -C 6 - alkylene,
  • R 27 is hydrogen, d-C 4 alkyl, C ⁇ -C alkoxycarbonyl or phenyl which may itself be substituted by C ⁇ -C 4 alkyl, C ⁇ -C haloalkyl, d-C 4 alkoxy, d-C haloalkoxy, d-C alkylcarbonyl, d-C 4 - alkoxycarbonyl, d.-C alkylam ⁇ no, d ⁇ -d-C 4 alkylam ⁇ no, C ⁇ -C alkylth ⁇ o, C 1 -C alkylsulf ⁇ nyl, d-C alkylsulfonyl, C ⁇ -C alkylsulfonyloxy, d-C 4 haloalkylth ⁇ o, d-C 4 haloalkylsulf ⁇ nyl, d-C 4 - haloalkylsulfonyl, d-C 4 haloalkylsulf
  • R 28 , R 29 , R 30 and R 31 are each independently of the others hydrogen or d-C 6 alkyl, or R 26 or
  • R 28 or R 30 together with R 21 or R 23 form a direct bond
  • R 32 is d-C ⁇ 2 alkyl
  • R 33 is C ⁇ -C 12 alkyl, or R 32 and R 33 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring, with the proviso that R 20 is other than C ⁇ -C 12 alkyl and d-C 4 ha!oalkyl when X is nitrogen or
  • the group -C(O)-Q occupies the 3-pos ⁇ t ⁇ on in the ring and R in the 6-pos ⁇ t ⁇ on in the ring is d-C 6 haloalkyl, or Q is the group Q 2
  • R 34 is hydrogen or C C 6 alkyl
  • R 35 is d-C 12 alkyl, d-C 12 haloalkyl C 2 -C ⁇ 2 alkenyl, C 2 -C 6 haloalkenyl, d-C 2 alkoxycarbonyl- or phenyl-substituted vinyl, or is C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 allenyl, C 3 -C 6 cycloalkyl, R ⁇ i R 52 , benzyl or phenyl, wherein the phenyl-containing groups may themselves be substituted by C C 3 alkyl, C 1 -C 3 - haloalkyl, d-C 3 alkoxy, C C 3 haloalkoxy, halogen, cyano or by nitro, or R 35 is hydroxy-
  • C C 12 alkyl d-C 4 alkoxy-d-C 12 alkyl, d-C 4 alkylth ⁇ o-d-C 12 alkyl, alkyl, d-C 4 alkyisulfonyl-d-C ⁇ 2 alkyl, cyano-C ⁇ -C 12 alkyl, d-Cealkylcarbonyloxy-d-d ⁇ alkyl,
  • each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or t ⁇ -substituted by d-C 6 alkyl, C C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 - haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, d-C 6 alkoxy, d-C 6 haloalkoxy, C 3 -C 6 alkenyloxy,
  • Y is a chemical bond, an alkylene group A-i , carbonyl, oxygen, sulfur, sulfinyl, sulfonyl, -NR 40 or NH(CO)R 41 ,
  • r and m 0 ⁇ are each independently of the other 0, 1 or 2,
  • R 36 is hydrogen, methyl or d-C 3 alkoxycarbonyl
  • R 37 , 38 , R 39 , R 44 , R 45 , R 42 and R 43 are each independently of the others hydrogen, d-C 4 - alkoxy, d-C 4 alkylth ⁇ o, d-C 4 alkylsulf ⁇ nyl, d-C 4 alkylsulfonyl, halogen or methyl
  • R 39 together with an adjacent group R 45 or R 43 denotes a chemical bond
  • R 0 and R 41 are each independently of the other hydrogen or C 1 -C 4 alkyl
  • R 51 is C ⁇ -C 12 alkyl
  • R 52 is C ⁇ -C 12 alkyl, or R 51 and R 52 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring, with the proviso that R 34 is C 5 -C 6 alkyl when R 35 is d-C 4 alkyl or d-C haloalkyl and X is nitrogen or NO, or Q is the group Q 3
  • R 6 is hydrogen or d-C 6 alkyl
  • R 47 is d-C ⁇ 2 alkyl, d-C ⁇ 2 haloalkyl, C 2 -C ⁇ 2 alkenyl, C 2 -C 6 haloalkenyl, d-C 2 alkoxycarbonyl- or phenyl-substituted vinyl, or is C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 allenyl, C 3 -C 6 cycloalkyl,
  • phenyl-containmg groups may themselves be substituted by C ⁇ -C 3 alkyl, CrC 3 haloalkyl, d-C 3 alkoxy, d-C 3 haloalkoxy, halogen, cyano or by nitro, or R 47 is hydroxy-C ⁇ -C 2 alkyl, d-C alkoxy-d-C ⁇ 2 alkyl, d-C 4 alkylth ⁇ o-C ⁇ -C ⁇ 2 alkyl, C r
  • R 47 ⁇ s a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the
  • each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or t ⁇ -substituted by d-C 6 alkyl, d-C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 - haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloaIkynyl, d-C 6 alkoxy, d-C 6 haloalkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, mercapto, d-C 6 alkylth ⁇ o, d-C 6 haloalkylth ⁇ o, C 3 -C 6 alkenylth ⁇ o, C 3 -C 6 alkenylth ⁇ o, C 3 -C 6 alkenylth ⁇ o, C 3 -C 6 alkenyl
  • R 50 is hydrogen, C C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, d-C alkoxycarbonyl, benzyl or phenyl, wherein benzyl or phenyl may themselves be substituted by C ⁇ -C alkyl, d- C haloalkyl, C C 4 alkoxy, d-C 4 -haloalkoxy, C ⁇ -C alkylcarbonyl, C C 4 alkoxycarbonyl, amino, d-dalkylamino, d ⁇ -C ⁇ -C 4 -alkylamino, d-C 4 alkylth ⁇ o, C ⁇ -C 4 alkylsulfinyl, d-C 4 alkylsulfonyl, d-C 4 alkylsulfonyloxy,
  • R 54 is C ⁇ -C ⁇ 2 alkyl, or R 53 and R 54 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring; with the proviso that R 46 is C 5 -C 6 alkyl when R 47 is C ⁇ -C 4 alkyl or C ⁇ -C 4 haloalkyl and X is nitrogen or NO; or Q is the group Q 4 wherein
  • R 60 is hydrogen or d-C 6 alkyl
  • R 6 ⁇ is C C 12 alkyl, C ⁇ -C ⁇ 2 haloalkyl, C 2 -C 12 alkenyl, C 2 -C 6 haloalkenyl, d-C 2 alkoxycarbonyl- or phenyl-substituted vinyl, or is C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 allenyl, C 3 -C 6 cycloalkyl, NR 62 R 63 , benzyl or phenyl, wherein the phenyl-containing groups may themselves be substituted by d-C 3 alkyl, d-C 3 haloalkyl, d-C 3 alkoxy, C ⁇ -C 3 haloalkoxy, halogen, cyano or by nitro, or R 61 is hydroxy-d-C 12 alkyl, d-C alkoxy-C ⁇ -C ⁇ 2 alkyl, d-C
  • R 59 is hydrogen, d-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, d-C 4 alkoxycarbonyl, benzyl or phenyl, wherein benzyl or phenyl may themselves be substituted by d-C 6 alkyl, d- C 6 haloalkyl, d-C 6 alkoxy, d-C 6 -haloalkoxy, d-C 6 alkylcarbonyl, C ⁇ -C 6 alkoxycarbonyl, ammo, d-C 4 alkylam ⁇ no, C 1 -C 4 -d ⁇ alkylam ⁇ no, d-C 6 alkylth ⁇ o, C ⁇ -C 6 alkylsulf ⁇ nyl, C C 6 alkylsulfonyl, d- C 4 alkylsulfonyloxy, d-C 4 haloalkylth ⁇ o, d-
  • alkyl groups mentioned in the substituent definitions may be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl or branched isomers thereof
  • Alkoxy, alkenyl and alkynyl radicals are derived from the mentioned alkyl radicals.
  • the alkenyl and alkynyl groups may be mono- or poly-unsaturated
  • alkylene group can be substituted by one or more methyl groups, such alkylene groups are preferably unsubstituted
  • alkylene groups are preferably unsubstituted
  • Halogen is generally fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine
  • halogen in conjunction with other definitions, such as haloalkyl or halophenyl
  • Haloalkyl groups having a chain length of from 1 to 6 carbon atoms are, for example, fluoromethyl, difluoromethyl, t ⁇ fluoromethyl, chloromethyl, dichloromethyl, t ⁇ chloromethyl, 2,2,2-t ⁇ fluoroethyl, 1 -fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-fluoro-prop-2-yl, pentafluoroethyl, 1 ,1-d ⁇ fluoro-2,2,2-tr ⁇ chloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-t ⁇ chloroethyl, pentafluoroethyl, heptafluoro-n-propyl, perfluoro-n-hexyl, haloalkyl groups in the definitions R 2 , R 3 and especially R 5 are preferably t ⁇ chloromethyl, fluoromethyl, dich
  • haloalkenyl there come into consideration alkenyl groups mono- or poly-substituted by halogen, wherein halogen is fluorine, chlorine, bromine or iodine and especially fluorine or chlorine, for example 1 -chlorov ⁇ nyl, 2-chlorov ⁇ nyl, 2,2-d ⁇ fiuorov ⁇ nyl, 2,2-d ⁇ fluoroprop-1 -en-2-yl, 2,2-d ⁇ chlorov ⁇ nyl, 3-fluoroprop-1 -enyl, chloroprop-1 -en-1 -yl, 3-bromoprop-1 -en-1 -yl, 2,3,3- tr ⁇ fluoroprop-2-en-1-yl, 2,3,3-t ⁇ chloroprop-2-en-1 -yl and 4,4,4-tr ⁇ fluoro-but-2-en-1 -yl.
  • halogen is fluorine, chlorine, bromine or iodine and especially fluorine or chlorine
  • haloalkynyl there come into consideration, for example, alkynyl groups mono- or poly- substituted by halogen, wherein halogen is bromine, iodine and especially fluorine or chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-t ⁇ fluoro- propynyl and 4,4,4-tr ⁇ fluoro-but-2-yn-1 -yl.
  • halogen is bromine, iodine and especially fluorine or chlorine
  • alkynyl groups mono- or poly-substituted by halogen preference is given to those having a chain length of from 2 to 5 carbon atoms.
  • a C 3 -C 6 cycloalkyl group mono- or poly-substituted by halogen is, for example, the 2,2-d ⁇ - chlorocyclopropyl, 2,2-d ⁇ bromocyclopropyl, 2,2,3,3-tetrafluorocyclobutyl or 2,2-d ⁇ fluoro-3,3- dichlorocyclobutyl group
  • Alkoxy groups preferably have a chain length of from 1 to 6 carbon atoms.
  • Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert- butoxy and the isome ⁇ c pentyloxy and hexyloxy groups, preferably methoxy or ethoxy
  • Alkylcarbonyl is preferably acetyl or propionyl
  • Alkoxycarbonyl is, for example, methoxy- carbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, iso- butoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl, ethoxycarbonyl or tert-butoxycarbonyl.
  • Haloalkoxy groups preferably have a chain length of from 1 to 6 carbon atoms.
  • Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoro- ethoxy, 1 ,1 ,2,2-tetrafluoroethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-di- fluoroethoxy or 2,2,2-trichloroethoxy; preferably fluoromethoxy, difluoromethoxy, 2-chloroethoxy or trifluoromethoxy.
  • Alkylthio groups preferably have a chain length of from 1 to 8 carbon atoms.
  • Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutyl- thio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio.
  • Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, iso- butylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl; preferably methylsulfinyl or ethylsulfinyl.
  • Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl.
  • Alkylamino is, for example, methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines.
  • Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino or diisopropylamino.
  • Alkoxyalkyl groups preferably have from 1 to 6 carbon atoms.
  • Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxy- methyl or isopropoxyethyl.
  • Alkylthioalkyl groups preferably have from 1 to 6 carbon atoms.
  • Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthio- ethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butyl- thiomethyl, butylthioethyl or butylthiobutyl.
  • Phenyl also as part of a substituent, such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyl or tosyl, can be mono- or poly-substituted.
  • the substituents can in that case be in the ortho-, meta- and/or para-position(s) as desired.
  • the invention also includes the salts that can be formed by the compounds of formula I, preferably with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
  • alkali metal bases and alkaline earth metal bases as salt formers, emphasis is given to the hydroxides of lithium, sodium, potassium, magnesium or calcium, especially those of sodium or potassium.
  • amines suitable for ammonium salt formation include ammonia and also primary, secondary and tertiary d-dsalkylamines, d-C 4 hydroxyalkylamines and C 2 -C 4 alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamibes, n- amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylamine
  • Quaternary ammonium bases suitable for salt formation are, for example, [N(R a R b R c R d )] + OH " , wherein R a , R , R c and R are each independently of the others d-C 4 alkyl. Further suitable tetraalkylammonium bases containing other anions can be obtained, for example, by anion exchange reactions.
  • M + is preferably an ammonium salt, especially NH + or an alkali metal, especially potassium or sodium.
  • the compounds of formula I may occur in various tautomeric forms, such as, for example, when Q is Q ⁇ , formulae la , lb and lc, with the forms la and lc being preferred: la lb lc
  • the present invention includes also all those stereoisomeric forms of the compound of formula I.
  • R ⁇ 9 , R 34 , R 46 and R 60 are hydrogen;
  • R 20 , R 35 , R ⁇ i and R 47 are each independently of the others C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, preferably trifluoromethyl, C 3 -C alkenyl, C 3 -C 4 haloalkenyl, benzyl or phenyl; wherein the phenyl-containing groups may themselves be substituted by C ⁇ -C 3 alkyl, d-C 3 - haloalkyl, C C 3 alkoxy, d-C 3 haloalkoxy, halogen, cyano or by nitro, or R 20 , R 35 , R ⁇ i and R 47 are hydroxy-d-C 12 alkyl, d-C 4 alkoxy-C C 12 alkyl, C 1 -C 4 alkylthio-C 1 -C 12 alkyl, C C 4 alkyl- sulfinyl-C ⁇
  • Q is the group Q ⁇ wherein W is -CR 25 R 26 - or oxygen and R 25 and R 26 are each independently of the other hydrogen, methyl or ethyl;
  • R 21 , R 22 , R 23 and R 24 are each independently of the others hydrogen, methyl, ethyl or t ⁇ fluoromethyl, or a maximum of one substituent selected from R 2 ⁇ , R 22 , R 23 and R 24 is methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl or methylsulfonyl, or W is -C(O)- and R 21 , R 22 , R 23 and R 24 are each independently of the others methyl or ethyl,
  • Q is the group Q 2 ; wherein Y is a methylene group, an ethylene group, carbonyl or oxygen and A is a methylene group or an ethylene group,
  • R 36 is hydrogen or methyl; and R 37 , R 38 and R 39 are each independently of the others hydrogen or methyl;
  • Q is the group Q 4 ; wherein Y is NR 59 ; R 59 is methyl or ethyl; ⁇ , R 56 . R 57 and R 58 are each independently of the others hydrogen, methyl or ethyl; or R 55 and R 57 together form a chemical bond or a methylene bridge;
  • Q is the group Q 3 ; wherein R 48 and R 49 are each independently of the other methyl or ethyl, and R 50 is methyl or ethyl;
  • X is methine, wherein the phenyl ring containing the substituent X is substituted in the 2- position relative to the substituent -C(O)-Q by methyl, ethyl, halomethyl, chlorine, bromine, nitro or by methylsulfonyl, and in the 4-pos ⁇ t ⁇ on relative to the substituent -C(O)-Q by halomethyl, chlorine, bromine, nitro, methylthio, methylsulfinyl, methylsulfonyl, methyl- sulfonyloxy, dimethylammosulfonyl, methylsulfonylammo or by halomethylsulfonylamino, and may contain a further substituent in the 3-pos ⁇ t ⁇ on relative to the substituent -C(O)-Q;
  • X is nitrogen; the group -C(O)-Q is preferably in the 3-pos ⁇ t ⁇ on relative thereto, and the ring carrying the substitutent X is substituted in the 2-pos ⁇ t ⁇ on by methyl, ethyl, n-propyl, halomethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, methylsulfinyl or by methyl- sulfonyl; and in the 6-pos ⁇ t ⁇ on by halomethyl, chlorine, bromine, methylthio, methylsulfinyl or by methylsulfonyl,
  • X is methine, and the phenyl ring is substituted in the 4-pos ⁇ t ⁇ on relative to the substituent -C(0)-Q by halomethyl, chlorine, bromine, nitro, methylthiomethyl, methylsulfinylmethyl, methylsulfonyl, methylsulfonyloxy, methylsulfonylammo or by halomethylsulfonylamino, and in the 2,3-pos ⁇ t ⁇ on relative to the substituent -C(O)-Q by a fused ring system, such as, preferably, by groups -S(O) n CH 2 CH 2 -, -S(0)nCH(CH 3 )CH 2 -, -SO 2 N(CH 3 )C(0)-, -CH 2 CH 2 O-, -CH 2 CH(CH 3 )0-, -CH 2 CH 2 CH 2 0-, -CH 2 CH 2 CH(CH 3 )0- or -CH 2 CH(CH 2 O
  • X is methine, and the phenyl ring is substituted in the 2-pos ⁇ t ⁇ on relative to the substituent -C(0)-Q by methyl, halomethyl, chlorine or by bromine, and in the 3,4-pos ⁇ t ⁇ on relative to the substituent -C(O)-Q by a fused ring system, such as preferably by the groups -S(0)nCH 2 CH 2 -, -S(O) n CH(CH 3 )CH 2 -, -CH 2 CH 2 CH 2 S(0) n , -CH(CH 3 )CH 2 CH 2 S(O) n -, -CH(OCH 3 )CH 2 CH 2 S(O) n -, -C(0)CH 2 CH 2 S(0) n -, -C(OCH 3 ) 2 CH 2 CH 2 S(O) n -, -C(NOH)CH 2 CH 2 S(0) n -, -C(NOCH 3 )CH 2 CH 2 S(0) n
  • R, m and X are as defined for formula I and Q is a group
  • R, m and X are as defined for formula I and Qa is a group
  • R 32 , R5 1 , R53 and R 62 are each independently of the others C ⁇ -C 12 alkyl and
  • R 33 , R 52 , R ⁇ and R 63 are each independently of the others d-C 12 alkyl, or R 32 and R 33 or R 5 and R 52 , or R 53 and R 54 or R 62 and R 63 , together with the nitrogen atom to which they are bonded, form a 3- to 7-membered ring, or b) in a compound of formula II
  • X, R, m and Qa are as defined above, using ammonia in an organic solvent, such as, for example, a halogenated hydrocarbon, for example dichloromethane, or an ether, for example tetrahydrofuran, or in a polar aprotic solvent, such as dimethylformamide or sulfolan, the leaving group X 1 is replaced by the ammo group, the resulting compound of formula IV
  • an organic solvent such as, for example, a halogenated hydrocarbon, for example dichloromethane, or an ether, for example tetrahydrofuran
  • a polar aprotic solvent such as dimethylformamide or sulfolan
  • R, m and X are as defined for formula I and Qb is a group
  • R 50 is reacted, in the presence of a suitable base, such as lithium diisopropylamide, sodium hydride or sodium bistrimethylsilylamide, at temperatures of from 100 °C to -20°C (preferably from 0 to 50°C) in an ether, for example tetrahydrofuran, or in a polar aprotic solvent, such as dimethylformamide or sulfolan, to form the corresponding anion, and the latter is then reacted with a compound of formula
  • a suitable base such as lithium diisopropylamide, sodium hydride or sodium bistrimethylsilylamide
  • R, m, Q and X are as defined above for formula I and R 19 , R 34 , R 46 and R 60 are hydrogen, can be converted by alkylation in a suitable solvent with an alkylating agent L-d-C 6 alkyl, wherein L is a leaving group, such as chlorine, bromine, iodine, mesyloxy or tosyloxy, in the presence of a base, for example sodium hydride, into compounds of formula I wherein R 19 , R 3 , R 46 and R 6 o are d-C 6 alkyl.
  • the compounds of formulae II and IV can be prepared by way of processes known per se, e g processes described in EP-A-0 249 813, WO 00/15615 and WO 00/39094 According to reaction scheme 1 , the compounds of formula II wherein X, is as defined above are prepared by way of the corresponding hydroxy compounds, for example by using a halogenat g agent, e g a thionyl halide, for example thionyl chloride or bromide, a phosphorus halide or a phosphorus oxyhahde, for example phosphorus pentachlo ⁇ de or phosphorus oxychlo ⁇ de or phosphorus pentabromide or phosphoryl bromide; or an oxalyl halide, for example oxalyl chloride, or by using a reagent for the formation of an activated ester, such as N,N'-d ⁇ cyclohexylcarbod ⁇ m ⁇ de (DCC) or N
  • the reaction is preferably carried out in an inert, organic solvent, such as in an aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbon, for example n- hexane, benzene, toluene, xylenes, dichloromethane, 1 ,2-d ⁇ chloroethane or chlorobenzene, at reaction temperatures in the range of from -20°C to the reflux temperature of the reaction mixture, preferably at 40-150°C, and in the presence of a catalytic amount of N,N-d ⁇ methyl- formamide.
  • organic solvent such as in an aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbon, for example n- hexane, benzene, toluene, xylenes, dichloromethane, 1 ,2-d ⁇ chloroethane or chlorobenzene
  • the end products of formula I can be isolated in customary manner by concentration or evaporation of the solvent, and can be purified by recrystalhsation or t ⁇ turation of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, by distillation or by column chromatography using a suitable eluant
  • the product can be in the form of a mixture of two or more isomers
  • the isomers can be separated according to methods known per se
  • a suitable oxidising agent such as with the adduct of H 2 0 2 and urea
  • the reactions to form compounds of formula I are advantageously carried out in aprotic, inert organic solvents
  • solvents are hydrocarbons, such as benzene, toluene, xylene and cyclohexane, chlorinated hydrocarbons, such as dichloromethane, t ⁇ chloromethane, tetrachloromethane and chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran and dioxane, nitnles, such as acetonit ⁇ le and propionit ⁇ le, amides, such as N,N-d ⁇ methylformam ⁇ de, diethylformamide and N-methylpyrrolidinone
  • the reaction temperatures are preferably from -20°C to +120°C
  • the reactions are generally slightly exothermic and can generally be carried out at room temperature In order to shorten the reaction time or in order to initiate the reaction, it
  • the compounds of formula I can be isolated in customary manner by concentration and/or evaporation of the solvent, and can be purified by recrystallisation or tnturation of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons
  • the compounds of formula I or of compositions comprising them there is suitable any method of application customary in agriculture, such as pre-emergence application, post-emergence application and seed dressing, as well as various methods and techniques, such as the controlled release of active ingredient
  • the compound is applied in solution to mineral granule carriers or polymerised granules (urea/formaldehyde) and dried
  • a coating coated granules
  • the compounds of formula I can be used as herbicides in unmodifed form, i e as obtained during synthesis, but are preferably formulated in customary manner together with the adjuvants conventionally employed in formulation technology, e g into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules and microcapsules Such formulations are described, for example, in WO 97/34485 on pages 9 to 13 As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances
  • compositions i e the compositions, preparation or mixtures comprising the compound (active ingredient) of formula I or at least one compound of formula I and generally one or more solid or liquid formulation adjuvant(s) are prepared in known manner, e g by intimately mixing and/or grinding the active ingredients with the formulation adjuvants, e g solvents or solid carriers
  • formulation adjuvants e g solvents or solid carriers
  • Surface-active compounds surfactants
  • solvents and solid carriers are given, for example, in WO 97/34485 on page 6.
  • suitable surface- active compounds are non-ionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties
  • herbicidal compositions are also suitable for the preparation of the herbicidal compositions according to the invention.
  • surfactants conventionally employed in formulation technology described inter alia in "Mc Cutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp , Ridgewood New Jersey, 1981 , Stache, H , "Tensid-Taschenbuch", Carl Hanser Verlag, Kunststoff/Vienna, 1981 and M. and J Ash, "Encyclopedia of Surfactants", Vol l-lll, Chemical Publishing Co , New York, 1980-81
  • the herbicidal formulations generally contain from 0 1 to 99 % by weight, especially from 0 1 to 95 % by weight, of herbicide, from 1 to 99 9 % by weight, especially from 5 to 99 8 % by weight, of a solid or liquid formulation adjuvant and from 0 to 25 % by weight, especially from 0.1 to 25 % by weight, of a surfactant
  • a surfactant e.g., a surfactant
  • the compositions may also comprise further auxiliaries, such as stabilisers, e g vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rape oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and tackifiers as well as fertilisers or other active ingredients
  • the compounds of formula I are generally applied to the plants or to their locus in rates of application of from 0 001 to 4 kg/ha, especially from 0 005 to 2 kg/ha
  • concentration required to achieve the desired effect can be determined by experimentation It is dependent upon the type of action, the stage of development of the crop plant and of the weed, and also upon the application (place, time, method) and, in dependence upon those parameters, can vary within wide limits
  • the compounds of formula I are distinguished by herbicidal and growth-inhibiting properties which enable them to be used in crops of useful plants, especially in cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and in non- selective weed control Crops are also to be understood as including those which have been rendered tolerant to herbicides or classes of herbicide by conventional methods of breeding or genetic engineering
  • the weeds to be controlled may be either monocotyledonous or dicotyledonous weeds, for example Stellaria, Nasturtium, Agrostis, Digita ⁇ a, Avena, Setaria, Sinapis, Lohum, Solanum, Echmochloa, Scirpus, Monocho ⁇ a, Sagitta ⁇ a, Bromus, Alopecurus, Sorghum halepense, Rottboelha, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoe
  • Example P1 Preparation of C,C,C-trifluoro-N-[3-(4-methanesulfonyl-2-nitro-benzoyl)-4-oxo- bicyclo 3.2.1loct-2-en-2-yl1-methanesulfonamide:
  • 0.25 g (1 .8 mmol) of trifluoromethylsulfonamide is added to a 55 % dispersion of 0.16 g (3.6 mmol) of sodium hydride in oil in 5 ml of anhydrous N-methylpyrrolidone, and the mixture is heated to a temperature of 50°C.
  • 0.64 g (1.6 mmol) of 4-chloro-3-(4-methanesulfonyl-2-nitro-benzoyl)-bicyclo[3.2.1]oct-3-en-2- one (e.g. known from JP 06025144 A2) is added in portions and the mixture is stirred for one hour at a temperature of 50°C.
  • reaction mixture is then acidified with 0.5N hydrochloric acid and subsequently extracted with ethyl acetate in the presence of a small amount of sodium chloride solution.
  • the product which is dried over sodium sulfate and concentrated by evaporation, is recrystallised from a 1 :1 mixture of dichloromethane and hexane to yield the pure C,C,C-trifluoro-N-[3-(4-methanesulfonyl-2-nitro-benzoyl)-4-oxo- bicyclo[3.2.1]oct-2-en-2-yl]-methanesulfonamide having a melting point of 178-180°C.
  • Monocotyledonous and dicotyledonous test plants are raised in a greenhouse in plastic pots containing standard soil and at the 4- to 6-leaf stage are sprayed with an aqueous suspension of the test compounds of formula I (prepared from a 25 % wettable powder (Example F3, b) according to WO 97/34485) or with an emulsion of the test compounds of formula I (prepared from a 25 % emulsifiable concentrate (Example F1 , c) according to WO 97/34485) at a rate of application corresponding to 250 g a.i./ha (500 litres water/ha).
  • the test plants are then grown on in the greenhouse under optimum conditions.

Abstract

Compounds of formula (I) wherein X is methine, nitrogen or N=O; m is 1, 2, 3 or 4; Q is (Q1), (Q2), or (Q3) or (Q4) and the other substituents are as defined in claim 1, exhibit herbicidal activity.

Description

ACYLATED PHENYL OR PYRIDINE HERBICIDES
The present invention relates to novel, herbicidally active benzoyl derivatives, to a process for their preparation, to compositions comprising those compounds, and to their use in controlling weeds, especially in crops of useful plants, or in inhibiting plant growth.
Benzoyl derivatives having herbicidal action are described, for example, in WO 97/08164, WO 99/09023 and EP-A-0 249 813. Novel benzoyl derivatives having herbicidal and growth- inhibiting properties have now been found.
The present invention accordingly relates to compounds of formula I
Figure imgf000002_0001
wherein X is methine, nitrogen or N=O; m is 1 , 2, 3 or 4; each R is independently hydrogen, Cι-C6alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6-alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, d-C6alkoxy, Cι-C6haloalkoxy, Cι-C6alkylthio, CrC6alkylsulfinyl, d-Cealkylsulfonyl, C C6haloalkyl, Cι-C6haloalkylthio, C C6haloalkyl- sulfinyl, C C6haloalkylsulfonyl, Cι-C6alkoxycarbonyl, C C6alkylcarbonyl, d-C6alkylamino, di-C C6alkylamino, Cι-C6alkylaminosulfonyl, di-Cι-C6alkylaminosulfonyl, -N(R1)-S-R2, -N(R3)-SO-R4, -N(R5)-SO2-R6, nitro, cyano, halogen, hydroxy, amino, formyl, hydroxy- CrC6alkyl, Ci-Cδalkoxy-d-Cealkyl, Cι-C6alkoxycarbonyloxy-Cι-C6alkyl, CrC6alkylthio- CrC6alkyl, Cι-C6alkylsulfinyl-Cι-C6alkyl, d-Cealkylsulfonyl-Ci-Cealkyl, rhodano-C C6alkyl, cyano-CrC6alkyl, oxiranyl, C3-C6alkenyloxy, C3-C6alkynyloxy, d-Cβalkoxy-d-Cealkoxy- d-C3alkyl, CrC6alkoxy-Cι-C6alkoxy, cyano-d-C6alkenyloxy, d-C6alkoxycarbonyloxy- CrC6alkoxy, C3-C6alkynyloxy, cyano-d-C6alkoxy, d-C6aikoxycarbonyl-Cι-C6alkoxy- d-C3alkyl, Cι-C6alkoxycarbonyl-d-C6alkoxy, d-C-ealkylthio-d-Cealkoxy, Cι-C6alkylthio- Cι-C6alkoxy-Cι-C3alkyl, alkoxycarbonyl-d-C6alkylthio, alkoxycarbonyl-d-C-ealkylthio-d-dr alkyl, alkoxycarbonyl-C C6alkylsulfinyl, alkoxycarbonyl-Cι-C6alkylsulfinyl-d-C3alkyl, alkoxycarbonyl-d-C6alkylsulfonyl, alkoxycarbonyl-d-Cealkylsulfonyl-d-dalkyl, d-C6- alkylsulfonyloxy, d-C6haloalkylsulfonyloxy, phenyl, benzyl, phenoxy, phenylthio, phenyl- sulfinyl, phenylsulfonyl, benzylthio, benzylsulfinyl or benzylsulfonyl, wherein the phenyl and benzyl groups may themselves be mono-, di- or tπ-substituted by d-C6alkyl, d-C6halo-alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, Cι-C6alkoxy, d-C6- haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C C6alkylthιo, d-C6haloalkylthιo, C3-C6alkenylthιo, C3-C6haloalkenylthιo, C3-C6alkynylthιo, C2-C5alkoxyalkylthιo, C3-C5acetyl- alkylthio, C3-C6alkoxycarbonylalkylthιo, C2-C4cyanoalkylthιo, C C6alkylsulfιnyl, Cι-C6halo- alkylsulfinyl, d-C6alkylsulfonyl, C C6haloalkylsulfonyl, aminosulfonyl, d-C2alkylamιno- sulfonyl, C2-C4dιalkylamιnosulfonyl, R7-d-C3alkylene-, NR8Rg, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein those phenylthio and benzylthio groups may themselves be substituted on the phenyl ring by C C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, or each R is independently a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system either being bonded directly to the ring containing the substituent X or being bonded to the ring containing the substituent X by way of a d-C4alkylene group; and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tn-substituted by d-C6alkyl, d- C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, C C6alkoxy, Ci- C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, d-C6alkylthιo, d-C6halo- alkylthio, C3-C6alkenylthιo, C3-C6haloaikenylthιo, C3-C6alkynylthιo, C2-C5alkoxyalkylthιo, C3-C5acetylalkylthιo, C3-C6alkoxycarbonylalkylthιo, C2-C4cyanoalkylthιo, C-,-C6alkylsulfιnyl, d-C6haloalkylsulfιnyl, d-C6alkylsulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, d-C4alkyl- aminosulfonyl, d-C4dιalkylamιnosulfonyl, R10-d-C3alkylene, NRnR12, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents at the nitrogen atom in the heterocyclic ring are free of halogen,
Ri, R3 and R5 are each independently of the others hydrogen or C C6alkyl, R2 ιs NR13Ru, C C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may itself be substituted by Cι-C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, R4 is NR15Rie, d-C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may itself be substituted by Cι-C3alkyl, C C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro; R6 is NRι7R 8, d-C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl, C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may itself be substituted by d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro; R7 and R10 are each independently of the other d-C3alkoxy, C2-C4alkoxycarbonyl, C1-C3- alkylthio, Cι-C3alkylsulfinyl, d-C3alkylsulfonyl or phenyl, wherein phenyl may itself be substituted by d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro;
R8, Rn, R13, R15 and R17 are each independently of the others d-C12alkyl; R9, R12, R14, R16 and R 8 are each independently of the others d-C12alkyl, or R8 and R9 together, and/or Rn and R12 together, and/or R13 and R14 together, and/or R15 and R16 together, and/or R17 and R 8 together, with the nitrogen atom to which they are bonded, form a 3- to 7-membered ring; Q is the group Q^
Figure imgf000004_0001
wherein
R19 is hydrogen or d-C6alkyl;
R20 is d-C^alkyl, d-Cι2haloalkyl, C2-Cι2alkenyl, C2-C6haloalkenyl, Cι-C2alkoxycarbonyl- or phenyl-substituted vinyl, or is C3-C6alkynyl, C3-C6haloalkynyl, C3-C6allenyl, C3-C6cycloalkyl,
NR32R33, benzyl or phenyl, wherein the phenyl-containing groups may themselves be substituted by C C3alkyl, Cι-C3- haloalkyl, d-C3alkoxy, C C3haloalkoxy, halogen, cyano or by nitro, or R20 is hydroxy- d-C12alkyl, d-C4alkoxy-Cι-Cι2alkyl, d-C4alkylthio-d-C12alkyl, d-dalkylsulfinyl-d-d∑r alkyl, d-C4alkylsulfonyl-Cι-Cι2alkyl, cyano-CrC^alkyl, d-C-ealkylcarbonyloxy-d-C^alkyl,
CrC4alkoxycarbonyl-d-Cι2alkyl, CrC4alkoxycarbonyloxy-Cι-C12alkyl, rhodano-CrC^alkyl, benzoyloxy-d-Cι2alkyl, C2-C6oxiranyl,
Figure imgf000004_0002
di(Cι-C4-alkyl)amino- d-C^alkyl, Cι-Cι2alkylthiocarbonyl-C C12alkyl or formyl-d-C12alkyl; or R20 ιs a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the -N(Rι9)-S(0)2- group by way of a Cι-C12alkylene group, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tri-substituted by C C6alkyl, C C6haloalkyl, C2-C6alkenyl, C2-C6- haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, d-C6alkoxy, d-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C C6alkylthio, d-C6haloalkylthio, C3-C6alkenylthio, C3-C6halo- alkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxy- carbonylalkylthio, C2-C4cyanoalkylthio, Cι-C6alkylsulfinyl, d-C6haloalkylsulfinyl, d-C6alkyl- sulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, Cι-C2alkylaminosulfonyl, di(C1-C2alkyl)"- aminosulfonyl, di(d-C4alkyl)amino, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by Cι-C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents at the nitrogen atom in the heterocyclic ring are free of halogen; R2ι, R22, R23 and R24 are each independently of the others hydrogen, d-C6alkyl, d-C6- haloalkyl, C2-C6alkenyl, C2-C6alkynyl, C C6alkoxycarbonyl, d-C6alkylcarbonyl, d-C6- alkylthio, C C6alkylsulfinyl, Cι-C6alkylsulfonyl, d-C6alkyl-NHS(0)2, d-C6alkylamino, di- (Cι-C6alkyl)amino, hydroxy, C C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, hydroxy-Cι-C6- alkyl, C C4alkylsulfonyloxy-Cι-C6alkyl, tosyloxy-d-C6alkyl, halogen, cyano, nitro, phenyl or phenyl substituted by Cι-C4alkyl, d-C4haloalkyl, d-C4alkoxy, d-C4haloalkoxy, d-C - alkylcarbonyl, C C4alkoxycarbonyl, amino, Cι-C4alkylamino, di-C1-C4alkylamino, Cι-C6- alkylthio, d-C6alkylsulfinyl, d-C6alkylsulfonyl, Cι-C4alkylsulfonyloxy, Cι-C6haloalkylthio, d-C-ehaloalkylsulfinyl, d-C6haloalkylsulfonyl, C C haloalkylsulfonyloxy, Cι-C4alkyl-S(O)2NH, d-C6alkylthio-N(d-C4alkyl), C1-C6alkylsulfinyl-N(C1-C4alkyl), d-C6alkylsulfonyl-N(C C alkyl), halogen, nitro, COOH or by cyano; or R24 and R21 together or R22 and R23 together denote C2-C6alkylene, C(O)OCH2CH2-, C(O)OCH2CH2CH2-, S-C2-C4alkylene, S(O)-C2-C4alkylene or S(O)2-C2-C4alkylene;
W is oxygen, sulfur, sulfinyl, sulfonyl, -CR25, R26-, -C(O)-, -CR28R29-CR30R3i- or -NR27, wherein the carbon atom carrying the substituents R28R29 is attached to the carbon atom carrying the substituents R22R23;
R25 is hydrogen, C C4alkyl, C C4haloalkyl, C1-C alkoxy-Cι-C4alkyl, Cι-C alkylthio-d-C - alkyl, C C alkylthio-C3-C6cycloalkyl, Cι-C4alkylcarbonyloxy-Cι-C4alkyl( d-C alkylsulfonyl- oxy-C C alkyl, tosyloxy-Cι-C alkyl, di(d-C3alkoxyalkyl)methyl, di(d-C3alkylthioalkyl)- methyl, (C1-C3alkoxyalkyl)-(C1-C3alkylthιoalkyl)methyl, C3-C5oxacycloalkyl, C3-C5thιacyclo- alkyl, C3-C4dιoxacycloalkyl, C3-C4dιthιacycloalkyl, C3-C4oxathιacycloalkyl, formyl, d-C4- alkoxycarbonyl, carbamoyl, d-C4alkylaminocarbonyl, dι(Cι-C4alkyl)amιnocarbonyl, phenylaminocarbonyl, benzylaminocarbonyl or phenyl which may itself be substituted by d-C4alkyl, Cι-C4haloalkyl, d-C4alkoxy, d-C4haloalkoxy, Cι-C4alkylcarbonyl, C C4alkoxy- carbonyl, ammo, C C4alkylamιno, di-d-dalkylamino, d-C4alkylthιo, d-C4alkylsulfιnyl, d-C4alkylsulfonyl, d-C4alkylsulfonyloxy, Cι-C haloalkylthιo, C1-C4haloalkylsulfιnyl, C C - haloalkylsulfonyl, d-C4haloalkylsulfonyloxy, C C4alkyl-S(O)2NH, d-C6alkylthιo-N-(d-C4- alkyl), C1-C6alkylsulfιnyl-N(C1-C4alkyl), d-C6alkylsulfonyl-N(d-C4alkyl), halogen, nitro,
COOH or by cyano, or R26 together with R23 or R24 denotes d-C5alkylene,
R26 is hydrogen, d-C alkyl or Cι-C4haloalkyl, or R26 together with R25 denotes C2-C6- alkylene,
R27 is hydrogen, d-C4alkyl, Cι-C alkoxycarbonyl or phenyl which may itself be substituted by Cι-C4alkyl, Cι-C haloalkyl, d-C4alkoxy, d-C haloalkoxy, d-C alkylcarbonyl, d-C4- alkoxycarbonyl, d.-C alkylamιno, dι-d-C4alkylamιno, Cι-C alkylthιo, C1-C alkylsulfιnyl, d-C alkylsulfonyl, Cι-C alkylsulfonyloxy, d-C4haloalkylthιo, d-C4haloalkylsulfιnyl, d-C4- haloalkylsulfonyl, d-C4haloalkylsulfonyloxy, C C4alkyl-S(O)2NH, C C4alkyl-S(0)2N(Ci-C4- alkyl), halogen, nitro or by cyano;
R28, R29, R30 and R31 are each independently of the others hydrogen or d-C6alkyl, or R26 or
R28 or R30 together with R21 or R23 form a direct bond;
R32 is d-Cι2alkyl;
R33 is Cι-C12alkyl, or R32 and R33 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring, with the proviso that R20 is other than Cι-C12alkyl and d-C4ha!oalkyl when X is nitrogen or
NO, the group -C(O)-Q occupies the 3-posιtιon in the ring and R in the 6-posιtιon in the ring is d-C6haloalkyl, or Q is the group Q2
Figure imgf000006_0001
wherein R34 is hydrogen or C C6alkyl,
R35 is d-C12alkyl, d-C12haloalkyl C2-Cι2alkenyl, C2-C6haloalkenyl, d-C2alkoxycarbonyl- or phenyl-substituted vinyl, or is C3-C6alkynyl, C3-C6haloalkynyl, C3-C6allenyl, C3-C6cycloalkyl, Rδi R52, benzyl or phenyl, wherein the phenyl-containing groups may themselves be substituted by C C3alkyl, C1-C3- haloalkyl, d-C3alkoxy, C C3haloalkoxy, halogen, cyano or by nitro, or R35 is hydroxy-
C C12alkyl, d-C4alkoxy-d-C12alkyl, d-C4alkylthιo-d-C12alkyl,
Figure imgf000007_0001
alkyl, d-C4alkyisulfonyl-d-Cι2alkyl, cyano-Cι-C12alkyl, d-Cealkylcarbonyloxy-d-d∑alkyl,
CrC alkoxycarbonyl-d-C12alkyl, d-C4alkoxycarbonyloxy-Cι-d2alkyl, rhodano-d-d2alkyl, benzoyloxy-d-C12alkyl, C2-C6oxιranyl, C1-C4alkylamιno-C1-C12alkyl, dι(d-C4alkyl)amιno- d-C12alkyl, d-C^alkylthiocarbonyl-CrC^alkyl or formyl-d-C^alkyl, or R35 ιs a five-to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the
-N(R34)-S(0)2- group by way of a d-C12alkylene group, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tπ-substituted by d-C6alkyl, C C6haloalkyl, C2-C6alkenyl, C2-C6- haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, d-C6alkoxy, d-C6haloalkoxy, C3-C6alkenyloxy,
C3-C6alkynyloxy, mercapto, d-C6alkylthιo, d-C6haloalkylthιo, C3-C6alkenylthιo, C3-C6halo- alkenylthio, C3-C6alkynylthιo, C2-C5alkoxyalkylthιo, C3-C5acetylalkylthιo, C3-C6alkoxy- carbonylalkylthio, C2-C4cyanoalkylthιo, d-C6alkylsulfιnyl, d-C6haloalkylsulfιnyl, d-C6alkyl- sulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, C C2alkylamιnosulfonyl, dι(d-C2alkyl)- aminosulfonyl, dι(C C4alkyl)amιno, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, Cι-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen atom in the hetero-cyclic ring are other than halogen,
Y is a chemical bond, an alkylene group A-i , carbonyl, oxygen, sulfur, sulfinyl, sulfonyl, -NR40 or NH(CO)R41 ,
Figure imgf000007_0002
r and m0ι are each independently of the other 0, 1 or 2,
R36 is hydrogen, methyl or d-C3alkoxycarbonyl, R37, 38, R39, R44, R45, R42 and R43 are each independently of the others hydrogen, d-C4- alkoxy, d-C4alkylthιo, d-C4alkylsulfιnyl, d-C4alkylsulfonyl, halogen or methyl, or R39 together with an adjacent group R45 or R43 denotes a chemical bond,
R 0 and R41 are each independently of the other hydrogen or C1-C4alkyl,
R51 is Cι-C12alkyl, and
R52 is Cι-C12alkyl, or R51 and R52 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring, with the proviso that R34 is C5-C6alkyl when R35 is d-C4alkyl or d-C haloalkyl and X is nitrogen or NO, or Q is the group Q3
Figure imgf000008_0001
wherein
R 6 is hydrogen or d-C6alkyl,
R47 is d-Cι2alkyl, d-Cι2haloalkyl, C2-Cι2alkenyl, C2-C6haloalkenyl, d-C2alkoxycarbonyl- or phenyl-substituted vinyl, or is C3-C6alkynyl, C3-C6haloalkynyl, C3-C6allenyl, C3-C6cycloalkyl,
NR53R54, benzyl or phenyl, wherein the phenyl-containmg groups may themselves be substituted by Cι-C3alkyl, CrC3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, or R47 is hydroxy-Cι-C 2alkyl, d-C alkoxy-d-Cι2alkyl, d-C4alkylthιo-Cι-Cι2alkyl, Cr
C4alkylsulfιnyl-d-C12alkyl, d-C4alkylsulfonyl-d-C12alkyl, cyano-Cι-Cι2alkyl, d-C6- alkylcarbonyloxy-C C^alkyl, d-C4alkoxycarbonyl-C -Cι2alkyl, d-C4alkoxycarbonyloxy- d-Cι2alkyl, rhodano-CrC 2alkyl, benzoyloxy-Cι-Cι2alkyl, C2-C6oxιranyl, d-C alkylamιno- d-C12alkyl, dι(d-C4alkyl)amιno-Cι-C12alkyl, d-C^alkylthiocarbonyl-Crd∑alkyl or formyl-
Cι-Cι2alkyl, or R47 ιs a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the
-N(R 6)-S(0)2- group by way of a Cι-Cι2alkylene group, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tπ-substituted by d-C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6- haloalkenyl, C2-C6alkynyl, C2-C6haloaIkynyl, d-C6alkoxy, d-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, d-C6alkylthιo, d-C6haloalkylthιo, C3-C6alkenylthιo, C3-C6halo- alkenylthio, C3-C6alkynylthιo, C2-C5alkoxyalkylthιo, C3-C5acetylalkylthιo, C3-C6alkoxy- carbonylalkylthio, C2-C4cyanoalkylthιo, d-C6alkylsulfιnyl, C C6haloalkylsulfιnyl, d-C6alkyl- sulfonyl, C C6haloalkylsulfonyl, aminosulfonyl, d-C2alkylamιnosulfonyl, dι(C C2alkyl)- aminosulfonyl, dι(d-C4alkyl)amιno, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by Cι-C3alkyl, d-C3haloalkyl, d-C3alkoxy, C C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents at the nitrogen atom in the heterocyclic ring are free of halogen; R48 and R 9 are each independently of the other hydrogen, Cι-C4alkyl, C2-C6alkenyl, C2-C6- alkynyl, Cι-C4alkoxycarbonyl, d-C6alkylthιo, C C6alkylsulfιnyl, d-C6alkylsulfonyl, C C4- aikyl-NHS(0)2, C1-C4haloalkyl, or phenyl which may itself be substituted by d-C4alkyt, CrC haloalkyl, C-|-C4alkoxy, d-C haloalkoxy, d-C4alkylcarbonyl, Cι-C4alkoxycarbonyl, ammo, Cι-C4alkylamιno, dι-d-C4alkylamιno, d-C6alkylthιo, d-C6alkylsulfιnyl, d-C6- alkylsulfonyl, d-C4alkylsulfonyloxy, Cι-C4haloalkylthιo, C1-C4haloalkylsulfιnyl, C C4- haloalkylsulfonyl, C C4haloalkylsulfonyloxy, d-C4alkyl-S(O)2NH, C1-C4alkyl-S(0)2N(C1-C4- alkyl), halogen, nitro, COOH or by cyano; or R48 and R49 together form a C2-C6alkylene bridge; and
R50 is hydrogen, C C6alkyl, C3-C6alkenyl, C3-C6alkynyl, d-C alkoxycarbonyl, benzyl or phenyl, wherein benzyl or phenyl may themselves be substituted by Cι-C alkyl, d- C haloalkyl, C C4alkoxy, d-C4-haloalkoxy, Cι-C alkylcarbonyl, C C4alkoxycarbonyl, amino, d-dalkylamino, dι-Cι-C4-alkylamino, d-C4alkylthιo, Cι-C4alkylsulfinyl, d-C4alkylsulfonyl, d-C4alkylsulfonyloxy,
Cι-C4haloalkylthιo, Cι-C4haloalkylsulfιnyl, C1-C4haloalkylsulfonyl, d-C haloalkylsulfonyloxy, d-C4alkyl-S(O)2NH, d-C4alkyl-S(O)2N(d-C4alkyl), halogen, nitro, COOH or by cyano; R53 is Cι-C12alkyl and
R54 is Cι-Cι2alkyl, or R53 and R54 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring; with the proviso that R46 is C5-C6alkyl when R47 is Cι-C4alkyl or Cι-C4haloalkyl and X is nitrogen or NO; or Q is the group Q4
Figure imgf000010_0001
wherein
R60 is hydrogen or d-C6alkyl;
R6ι is C C12alkyl, Cι-Cι2haloalkyl, C2-C12alkenyl, C2-C6haloalkenyl, d-C2alkoxycarbonyl- or phenyl-substituted vinyl, or is C3-C6alkynyl, C3-C6haloalkynyl, C3-C6allenyl, C3-C6cycloalkyl, NR62R63, benzyl or phenyl, wherein the phenyl-containing groups may themselves be substituted by d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, Cι-C3haloalkoxy, halogen, cyano or by nitro, or R61 is hydroxy-d-C12alkyl, d-C alkoxy-Cι-Cι2alkyl, d-C4alkylthio-C Cι2alkyl, Cr C alkylsulfinyl-CrC12alkyl, d-C alkylsulfonyl-C C12alkyl, cyano-C Cι2alkyl, Cι-C6- alkylcarbonyloxy-d-Cι2alkyl, Cι-C4alkoxycarbonyl-d-C12alkyl, Cι-C4alkoxycarbonyloxy- CrCι2alkyl, -rhodano-d-Cι2alkyl, benzoyloxy-Cι-C12a!kyl, C2-C6oxiranyl, d-C4alkylamino-Cr C12alkyl, di(d-C alkyl)amino-CrC12alkyl, d-Cι2alkylthiocarbonyl-d-Cι2alkyl or formyl- C Cι2alkyl; or R61 is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the -N(R60)-S(O)2- group by way of a d-Cι2alkylene group, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tri-substituted by d-C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6- haloalkenyl, C2-C6alkynyl, C -C6haloalkynyl, d-C6alkoxy, C C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, d-C6alkylthio, d-C6haloalkylthio, C3-C6alkenylthio, C3-C6halo- alkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxy- carbonylalkylthio, C2-C4cyanoalkylthio, d-C6alkylsulfinyl, Cι-C6haloalkylsulfinyl, d-C6- alkylsulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, d-C2alkylaminosuIfonyl, di(d-C2alkyl)- aminosulfonyl, di(C C4alkyl)amino, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by CrC3alkyl, CrC3haloalkyl, C C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents at the nitrogen atom in the heterocyclic ring are free of halogen; R62 is d-d∑alkyl and R63 is Cι-C12alkyl, or R62 and R63 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring, Yi is oxygen or NR59,
R59 is hydrogen, d-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, d-C4alkoxycarbonyl, benzyl or phenyl, wherein benzyl or phenyl may themselves be substituted by d-C6alkyl, d- C6haloalkyl, d-C6alkoxy, d-C6-haloalkoxy, d-C6alkylcarbonyl, Cι-C6alkoxycarbonyl, ammo, d-C4alkylamιno, C1-C4-dιalkylamιno, d-C6alkylthιo, Cι-C6alkylsulfιnyl, C C6alkylsulfonyl, d- C4alkylsulfonyloxy, d-C4haloalkylthιo, d-C4haloalkylsulfιnyl, Cι-C haloalkylsulfonyl, d-C4haloalkylsulfonyloxy, d-C4alkyl-S(0)2NH, Cι-C4alkyl-S(O)2N(C1-C4alkyl), halogen, nitro, COOH or by cyano, R55, R56, R57 and R58 are each independently of the others hydrogen, hydroxy-Cι-C4afkyl, d- C6alkyl, d-C4alkoxy-Cι-C alkyl, C2-C6alkenyl, C2-C6alkynyl, d-C6alkoxycarbonyl, d-C6- alkylthio, d-C6alkylsulfιnyl, d-C6alkylsulfonyl, C C4alkylamιnosulfonyl, Cι-C4haloalkyl, C1-C6alkylsulfonyloxy-C1-C4alkyl, phenylsulfonyloxy-Cι-C4alkyl, Cι-C6alkylamιno, d-C6- dialkylammo, C C6alkoxy or phenyl, wherein the phenyl group may itself be substituted by d-dalkyl, Cι-C4haloalkyl, C C alkoxy, C1-C4haloalkoxy, Cι-C4alkylcarbonyl, Cι-C4alkoxy- carbonyl, halogen, nitro, COOH or by cyano, or R55 and R56 together form a C2-C5alkylene chain, or R55 and R57 together form a chemical bond or a C C4alkylene chain, or R57 together with R59 forms a chemical bond or a C3-C4alkylene chain, and to the agrochemically tolerable salts and all stereoisomers and tautomers of the compounds of formula I
The alkyl groups mentioned in the substituent definitions may be straight-chain or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl or branched isomers thereof Alkoxy, alkenyl and alkynyl radicals are derived from the mentioned alkyl radicals. The alkenyl and alkynyl groups may be mono- or poly-unsaturated
An alkylene group can be substituted by one or more methyl groups, such alkylene groups are preferably unsubstituted The same applies also to all groups containing C3-C6- cycloalkyl, C3-C5oxacycloalkyl, C3-C5thιacycloalkyl, C3-C4dιoxacycloalkyl, C3-C4dιthιa- cycloalkyl or C3-C4oxathιacycloalkyl Halogen is generally fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine The same is also true of halogen in conjunction with other definitions, such as haloalkyl or halophenyl
Haloalkyl groups having a chain length of from 1 to 6 carbon atoms are, for example, fluoromethyl, difluoromethyl, tπfluoromethyl, chloromethyl, dichloromethyl, tπchloromethyl, 2,2,2-tπfluoroethyl, 1 -fluoroethyl, 2-fluoroethyl, 2-chloroethyl, 2-fluoro-prop-2-yl, pentafluoroethyl, 1 ,1-dιfluoro-2,2,2-trιchloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-tπchloroethyl, pentafluoroethyl, heptafluoro-n-propyl, perfluoro-n-hexyl, haloalkyl groups in the definitions R2, R3 and especially R5 are preferably tπchloromethyl, fluoromethyl, dichlorofluoromethyl, difluorochloromethyl, difluoromethyl, tnfluoromethyl, pentafluoroethyl or heptafluoro-n-propyl
As haloalkenyl there come into consideration alkenyl groups mono- or poly-substituted by halogen, wherein halogen is fluorine, chlorine, bromine or iodine and especially fluorine or chlorine, for example 1 -chlorovιnyl, 2-chlorovιnyl, 2,2-dιfiuorovιnyl, 2,2-dιfluoroprop-1 -en-2-yl, 2,2-dιchlorovιnyl, 3-fluoroprop-1 -enyl, chloroprop-1 -en-1 -yl, 3-bromoprop-1 -en-1 -yl, 2,3,3- trιfluoroprop-2-en-1-yl, 2,3,3-tπchloroprop-2-en-1 -yl and 4,4,4-trιfluoro-but-2-en-1 -yl. Of the C2-C6alkenyl groups mono-, di- or tπ-substituted by halogen, preference is given to those having a chain length of from 2 to 5 carbon atoms.
As haloalkynyl there come into consideration, for example, alkynyl groups mono- or poly- substituted by halogen, wherein halogen is bromine, iodine and especially fluorine or chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-tπfluoro- propynyl and 4,4,4-trιfluoro-but-2-yn-1 -yl. Of the alkynyl groups mono- or poly-substituted by halogen, preference is given to those having a chain length of from 2 to 5 carbon atoms.
A C3-C6cycloalkyl group mono- or poly-substituted by halogen is, for example, the 2,2-dι- chlorocyclopropyl, 2,2-dιbromocyclopropyl, 2,2,3,3-tetrafluorocyclobutyl or 2,2-dιfluoro-3,3- dichlorocyclobutyl group
Alkoxy groups preferably have a chain length of from 1 to 6 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert- butoxy and the isomeπc pentyloxy and hexyloxy groups, preferably methoxy or ethoxy Alkylcarbonyl is preferably acetyl or propionyl Alkoxycarbonyl is, for example, methoxy- carbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, iso- butoxycarbonyl, sec-butoxycarbonyl or tert-butoxycarbonyl; preferably methoxycarbonyl, ethoxycarbonyl or tert-butoxycarbonyl. Haloalkoxy groups preferably have a chain length of from 1 to 6 carbon atoms.
Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2-trifluoro- ethoxy, 1 ,1 ,2,2-tetrafluoroethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2,2-di- fluoroethoxy or 2,2,2-trichloroethoxy; preferably fluoromethoxy, difluoromethoxy, 2-chloroethoxy or trifluoromethoxy.
Alkylthio groups preferably have a chain length of from 1 to 8 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutyl- thio, sec-butylthio or tert-butylthio, preferably methylthio or ethylthio. Alkylsulfinyl is, for example, methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, iso- butylsulfinyl, sec-butylsulfinyl or tert-butylsulfinyl; preferably methylsulfinyl or ethylsulfinyl.
Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl or tert-butylsulfonyl; preferably methylsulfonyl or ethylsulfonyl.
Alkylamino is, for example, methylamino, ethylamino, n-propylamino, isopropylamino or the isomeric butylamines. Dialkylamino is, for example, dimethylamino, methylethylamino, diethylamino, n-propylmethylamino, dibutylamino or diisopropylamino. Preference is given to alkylamino groups having a chain length of from 1 to 4 carbon atoms. Alkoxyalkyl groups preferably have from 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxy- methyl or isopropoxyethyl. Alkylthioalkyl groups preferably have from 1 to 6 carbon atoms. Alkylthioalkyl is, for example, methylthiomethyl, methylthioethyl, ethylthiomethyl, ethylthio- ethyl, n-propylthiomethyl, n-propylthioethyl, isopropylthiomethyl, isopropylthioethyl, butyl- thiomethyl, butylthioethyl or butylthiobutyl.
Phenyl, also as part of a substituent, such as phenoxy, benzyl, benzyloxy, benzoyl, phenylthio, phenylalkyl, phenoxyalkyl or tosyl, can be mono- or poly-substituted. The substituents can in that case be in the ortho-, meta- and/or para-position(s) as desired. Allenyl is, for example, CH2=C=CH2 , CH2=CH-CH2-CH=CH2 , CH2=CH-CH2-CH2-CH=CH2 or CH2=CH-CH2 _CH=CH-CH3.
The invention also includes the salts that can be formed by the compounds of formula I, preferably with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Among the alkali metal bases and alkaline earth metal bases as salt formers, emphasis is given to the hydroxides of lithium, sodium, potassium, magnesium or calcium, especially those of sodium or potassium. Examples of amines suitable for ammonium salt formation include ammonia and also primary, secondary and tertiary d-dsalkylamines, d-C4hydroxyalkylamines and C2-C4alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamibes, n- amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptyl- amine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, di-iso-amylamine, dihexylamine, diheptylamine, dioctyl- amine, ethanolamine, n-propanolamine, isopropanolamine, N,N-diethanolamine, N-ethyl- propanolamine, N-butylethanolamine, 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, triisopropylamine, tri-n-butylamine, triiso- butylamine, tri-sec-butylamine, tri-n-amylamine, methoxyethylamine and ethoxyethylamine; heterocyclic amines, for example pyridine, quinoline, isoquinoline, morpholine, piperidine, pyrrolidine, indoline, quinuclidine and azepine; primary arylamines, for example anilines, methoxyanilines, ethoxyanilines, o-, m- and p-toluidines, phenylenediamines, naphthyl- amines and o-, m- and p-chloroanilines; but especially triethylamine, isopropylamine and diisopropylamine. Quaternary ammonium bases suitable for salt formation are, for example, [N(Ra Rb R c R d)]+ OH" , wherein Ra, R , Rc and R are each independently of the others d-C4alkyl. Further suitable tetraalkylammonium bases containing other anions can be obtained, for example, by anion exchange reactions. M+ is preferably an ammonium salt, especially NH +or an alkali metal, especially potassium or sodium.
The compounds of formula I may occur in various tautomeric forms, such as, for example, when Q is Qι, formulae la , lb and lc, with the forms la and lc being preferred:
Figure imgf000015_0001
la lb lc
The present invention includes also all those stereoisomeric forms of the compound of formula I.
Of the compounds of formula I, special preference is given to those groups wherein:
a) Rι9, R34, R46 and R60 are hydrogen; R20, R35, Rβi and R47 are each independently of the others Cι-C4alkyl, Cι-C4haloalkyl, preferably trifluoromethyl, C3-C alkenyl, C3-C4haloalkenyl, benzyl or phenyl; wherein the phenyl-containing groups may themselves be substituted by Cι-C3alkyl, d-C3- haloalkyl, C C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, or R20, R35, Rεi and R47 are hydroxy-d-C12alkyl, d-C4alkoxy-C C12alkyl, C1-C4alkylthio-C1-C12alkyl, C C4alkyl- sulfinyl-Cι-C12alkyl, d-dalkylsulfonyl-d-C^alkyl, cyano-Cι-Ci2alkyl, d-C6alkylcarbonyl-oxy- C C12alkyl, C1-C alkoxycarbonyl-C1-C12alkyl, d-C4alkoxycarbonyloxy-d-C 2alkyl, rhodano- Cι-Cι2alkyl, benzoyloxy-C C^alkyl, C2-C6oxiranyl, d-dalkylamino-d-C^alkyl, di(Cι- C4alkyl)amino-d-C12alkyl, d-C^alkylthiocarbonyl-CrC^alkyl, NR32R33, NR51R52, NR53R54, NR55R56 or formyl-Cι-Cι2alkyl; or R 0, R35, R8i and R47 are a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di-or tri-substituted by d-C6alkyl, d-C6haloalkyl, d-C6alkoxy, d-C6alkyl-thio, C1- C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthio, d-C6alkylsulfinyl, d-C6- haloalkylsulfinyl, d-C6alkylsulfonyl, d-C6haloalkylsulfonyl, halogen, cyano, nitro, phenylthio and/or by benzylthio, and wherein the substituents at the nitrogen atom in the heterocyclic ring are free of halogen; R32, R51, R53 and R62 are each independently of the others d-C12alkyl and R33, R52, Rδ and R63 are each independently of the others Cι-C12alkyl, or R32 and R33, or R51 and R52, or R53 and R54, or R62 and R63, together with the nitrogen atom to which they are bonded, form a 3- to 7 membered ring,
b) Q is the group Q^ wherein W is -CR25R26- or oxygen and R25 and R26 are each independently of the other hydrogen, methyl or ethyl;
R21 , R22, R23 and R24 are each independently of the others hydrogen, methyl, ethyl or tπfluoromethyl, or a maximum of one substituent selected from R2ι , R22, R23 and R24 is methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl or methylsulfonyl, or W is -C(O)- and R21, R22, R23 and R24 are each independently of the others methyl or ethyl,
c) Q is the group Q2; wherein Y is a methylene group, an ethylene group, carbonyl or oxygen and A is a methylene group or an ethylene group,
R36 is hydrogen or methyl; and R37, R38 and R39 are each independently of the others hydrogen or methyl;
d) Q is the group Q4; wherein Y is NR59; R59 is methyl or ethyl; δδ, R56. R57 and R58 are each independently of the others hydrogen, methyl or ethyl; or R55 and R57 together form a chemical bond or a methylene bridge;
e) Q is the group Q3; wherein R48 and R49 are each independently of the other methyl or ethyl, and R50 is methyl or ethyl;
f) X is methine, wherein the phenyl ring containing the substituent X is substituted in the 2- position relative to the substituent -C(O)-Q by methyl, ethyl, halomethyl, chlorine, bromine, nitro or by methylsulfonyl, and in the 4-posιtιon relative to the substituent -C(O)-Q by halomethyl, chlorine, bromine, nitro, methylthio, methylsulfinyl, methylsulfonyl, methyl- sulfonyloxy, dimethylammosulfonyl, methylsulfonylammo or by halomethylsulfonylamino, and may contain a further substituent in the 3-posιtιon relative to the substituent -C(O)-Q;
g) X is nitrogen; the group -C(O)-Q is preferably in the 3-posιtιon relative thereto, and the ring carrying the substitutent X is substituted in the 2-posιtιon by methyl, ethyl, n-propyl, halomethyl, methoxymethyl, ethoxymethyl, methylthiomethyl, methylsulfinyl or by methyl- sulfonyl; and in the 6-posιtιon by halomethyl, chlorine, bromine, methylthio, methylsulfinyl or by methylsulfonyl,
h) X is methine, and the phenyl ring is substituted in the 4-posιtιon relative to the substituent -C(0)-Q by halomethyl, chlorine, bromine, nitro, methylthiomethyl, methylsulfinylmethyl, methylsulfonyl, methylsulfonyloxy, methylsulfonylammo or by halomethylsulfonylamino, and in the 2,3-posιtιon relative to the substituent -C(O)-Q by a fused ring system, such as, preferably, by groups -S(O)nCH2CH2-, -S(0)nCH(CH3)CH2-, -SO2N(CH3)C(0)-, -CH2CH2O-, -CH2CH(CH3)0-, -CH2CH2CH20-, -CH2CH2CH(CH3)0- or -CH2CH(CH2OCH3)0-, wherein n is 0, 1 or 2; and
i) X is methine, and the phenyl ring is substituted in the 2-posιtιon relative to the substituent -C(0)-Q by methyl, halomethyl, chlorine or by bromine, and in the 3,4-posιtιon relative to the substituent -C(O)-Q by a fused ring system, such as preferably by the groups -S(0)nCH2CH2-, -S(O)nCH(CH3)CH2-, -CH2CH2CH2S(0)n, -CH(CH3)CH2CH2S(O)n-, -CH(OCH3)CH2CH2S(O)n-, -C(0)CH2CH2S(0)n-, -C(OCH3)2CH2CH2S(O)n-, -C(NOH)CH2CH2S(0)n-, -C(NOCH3)CH2CH2S(0)n- or -SO2N(CH3)C(O)-, wherein n is 0, 1 or 2.
In the process according to the invention for the preparation of compounds of formula I
Figure imgf000017_0001
wherein R, m and X are as defined for formula I and Q is a group
Figure imgf000018_0001
Figure imgf000018_0002
R 5. 0
either a) a compound of formula II
Figure imgf000018_0003
wherein R, m and X are as defined for formula I and Qa is a group
Figure imgf000018_0004
Figure imgf000019_0001
R50 wherein -\ is a leaving group, for example halogen, is reacted in a polar aprotic solvent, such as acetonitπle, dimethylformamide or sulfolan, with a compound of formula M-N(R19)SO2R20 (llla, when Qa is Q,a), or M-N(R34)S02R35 (lllb, when Qa is Q2a), or M-N(R46)S02R47 (lllc, when Qa is Q3a), or M-N(R60)SO2R61 (llld, when Qa is Q4a), wherein M is lithium, sodium, potassium, magnesium or calcium, especially sodium or potassium; R19, R34, R46 and R60 are each independently of the others hydrogen or d-C6- alkyl; and R20, R35, R47 and R61 are each independently of the others Cι-Cι2alkyl, Cι-Cι2- haloalkyl, C2-C12alkenyl, C2-C6haloalkenyl, C1-C2alkoxycarbonyl- or phenyl-substituted vinyl, or is C3-C6alkynyl, C3-C6haloalkynyl, C3-C6allenyl, C3-C6cycloalkyl, NR32R33, NR51 R52, NR53R5 , NR62R63, benzyl or phenyl, wherein the phenyl-containing groups may themselves be substituted by d-C3alkyl, d-C3- haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, or R20, R35, R6ι and R47 are hydroxy-d-d2alkyl, d-C4alkoxy-Cι-C12alkyl, Cι-C4alkylthιo-Cι-Cι2alkyl, d-C alkyl- sulfιnyl-Cι-C12alkyl, d-C4alkylsulfonyl-Cι-C12alkyl, cyano-d-d2alkyl, d-C6alkylcarbonyl-oxy- d-Cι2alkyl, C -C4alkoxycarbonyl-C1-C12alkyl, d-C4alkoxycarbonyloxy-Cι-C12alkyl, rhodano- C Cι2alkyl, benzoyloxy-d-C12alkyl, C2-C6oxιranyl, Cι-C alkylamιno-d-Ci2alkyl, dι(Cι- dalkyhamino-Crd∑alkyl, d-d2alkylthιocarbonyl-Cι-Cι2alkyl or formyl-CrC12alkyl; or R20, R35, R6ι and R47 are a five-to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the -N(R19)-S(0)2-, -N(R34)-S(0)2-, -N(R46)-S(0)2- or -N(R60)-S(O)2- group by way of a d-Cι2alkylene group, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tπ- substituted by d-C6alkyl, C C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, d-C6alkoxy, d-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, d-C6alkylthιo, d-C6haloalkylthιo, C3-C6alkenylthιo, C3-C6haloalkenylthιo, C3-C6- alkynylthio, C2-C5alkoxyalkylthιo, C3-C5acetylalkylthιo, C3-C6alkoxycarbonylalkylthιo, C2-C - cyanoalkylthio, C C6alkylsulfιnyl, d-C6haloalkylsulfιnyl, d-C6alkylsulfonyl, d-C6haloalkyl- sulfonyl, aminosulfonyl, C C2alkylamιnosulfonyl, dι(d-C2-alkyl)amιnosulfonyl, dι(d-C4- alkyl)amιno, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by d-C3alkyI, Cι-C3haloaikyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen atom in the heterocyclic ring are other than halogen,
R32, R51 , R53 and R62 are each independently of the others Cι-C12alkyl and
R33, R52, Rβ and R63 are each independently of the others d-C12alkyl, or R32 and R33 or R5 and R52, or R53 and R54 or R62 and R63, together with the nitrogen atom to which they are bonded, form a 3- to 7-membered ring, or b) in a compound of formula II
Figure imgf000020_0001
wherein X, R, m and Qa are as defined above, using ammonia in an organic solvent, such as, for example, a halogenated hydrocarbon, for example dichloromethane, or an ether, for example tetrahydrofuran, or in a polar aprotic solvent, such as dimethylformamide or sulfolan, the leaving group X1 is replaced by the ammo group, the resulting compound of formula IV
Figure imgf000020_0002
wherein R, m and X are as defined for formula I and Qb is a group
Figure imgf000021_0001
Figure imgf000021_0002
Figure imgf000021_0003
R50 is reacted, in the presence of a suitable base, such as lithium diisopropylamide, sodium hydride or sodium bistrimethylsilylamide, at temperatures of from 100 °C to -20°C (preferably from 0 to 50°C) in an ether, for example tetrahydrofuran, or in a polar aprotic solvent, such as dimethylformamide or sulfolan, to form the corresponding anion, and the latter is then reacted with a compound of formula
(X2)SO2R20 (Va, when Q is Q^), or
(X2)S02R35 (Vb), when Q is Q2b), or
(X2)S02R47 (Vc, when Q is Q3b), or
(X2)S02R61 (Vd, when Q is Q4b), wherein X2 is a leaving group, for example halogen, and R2o, R35, R47 and R61 are as defined above.
The resulting compound of formula I
Figure imgf000022_0001
wherein R, m, Q and X are as defined above for formula I and R19, R34, R46 and R60 are hydrogen, can be converted by alkylation in a suitable solvent with an alkylating agent L-d-C6alkyl, wherein L is a leaving group, such as chlorine, bromine, iodine, mesyloxy or tosyloxy, in the presence of a base, for example sodium hydride, into compounds of formula I wherein R19, R3 , R46 and R6o are d-C6alkyl.
Those reaction sequences, Routes a) and b), are described in more detail by way of the following Example (Q, Q2):
Scheme 1
Figure imgf000023_0001
activation e g halogenation e g (C(XI)2 , cat DMF
Figure imgf000023_0002
The compounds of formulae II and IV can be prepared by way of processes known per se, e g processes described in EP-A-0 249 813, WO 00/15615 and WO 00/39094 According to reaction scheme 1 , the compounds of formula II wherein X, is as defined above are prepared by way of the corresponding hydroxy compounds, for example by using a halogenat g agent, e g a thionyl halide, for example thionyl chloride or bromide, a phosphorus halide or a phosphorus oxyhahde, for example phosphorus pentachloπde or phosphorus oxychloπde or phosphorus pentabromide or phosphoryl bromide; or an oxalyl halide, for example oxalyl chloride, or by using a reagent for the formation of an activated ester, such as N,N'-dιcyclohexylcarbodιιmιde (DCC) or N-ethyl-N'-(3-dιmethylamιnopropyl)- carbodnmide (EDC)
The reaction is preferably carried out in an inert, organic solvent, such as in an aliphatic, halogenated aliphatic, aromatic or halogenated aromatic hydrocarbon, for example n- hexane, benzene, toluene, xylenes, dichloromethane, 1 ,2-dιchloroethane or chlorobenzene, at reaction temperatures in the range of from -20°C to the reflux temperature of the reaction mixture, preferably at 40-150°C, and in the presence of a catalytic amount of N,N-dιmethyl- formamide. Such reactions are generally known and are described in the literature with a number of variations for the leaving group Xi (or X2)
The end products of formula I can be isolated in customary manner by concentration or evaporation of the solvent, and can be purified by recrystalhsation or tπturation of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons, by distillation or by column chromatography using a suitable eluant
The person skilled in the art will also be familiar with the order in which it is expedient to carry out certain reactions in order to avoid any possible secondary reactions. Where the synthesis is not targeted at the isolation of pure isomers, the product can be in the form of a mixture of two or more isomers The isomers can be separated according to methods known per se
Compounds of formula I wherein X is N=0 can be prepared by reacting a compound of formula I wherein X is nitrogen with a suitable oxidising agent, such as with the adduct of H202and urea, in the presence of an acid anhydride, for example tπfluoroacetic anhydride. The reactions to form compounds of formula I are advantageously carried out in aprotic, inert organic solvents Such solvents are hydrocarbons, such as benzene, toluene, xylene and cyclohexane, chlorinated hydrocarbons, such as dichloromethane, tπchloromethane, tetrachloromethane and chlorobenzene, ethers such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran and dioxane, nitnles, such as acetonitπle and propionitπle, amides, such as N,N-dιmethylformamιde, diethylformamide and N-methylpyrrolidinone The reaction temperatures are preferably from -20°C to +120°C The reactions are generally slightly exothermic and can generally be carried out at room temperature In order to shorten the reaction time or in order to initiate the reaction, it is also possible to heat the reaction mixture for a short time up to its boiling point The reaction times can also be shortened by the addition of a few drops of a base as reaction catalyst Suitable bases are especially tertiary amines, such as tπmethylamine, triethylamine, quinuchdine, 1 ,4-dιazabιcyclo[2 2 2]octane, 1 ,5-dιazabιcyclo[4 3 0]non-5-ene or 1 ,5- dιazabιcyclo[5 4 0]undec-7-ene but as bases it is also possible to use inorganic bases, such as hydrides, such as sodium or calcium hydride, hydroxides, such as sodium or potassium hydroxide, carbonates, such as sodium or potassium carbonate, or hydrogen carbonates, such as potassium or sodium hydrogen carbonate
The compounds of formula I can be isolated in customary manner by concentration and/or evaporation of the solvent, and can be purified by recrystallisation or tnturation of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons
For the use according to the invention of the compounds of formula I or of compositions comprising them there is suitable any method of application customary in agriculture, such as pre-emergence application, post-emergence application and seed dressing, as well as various methods and techniques, such as the controlled release of active ingredient In that method, the compound is applied in solution to mineral granule carriers or polymerised granules (urea/formaldehyde) and dried Where appropriate, it is also possible to apply a coating (coated granules), which allows the active ingredient to be released in metered amounts over a specific period
The compounds of formula I can be used as herbicides in unmodifed form, i e as obtained during synthesis, but are preferably formulated in customary manner together with the adjuvants conventionally employed in formulation technology, e g into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules and microcapsules Such formulations are described, for example, in WO 97/34485 on pages 9 to 13 As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances
The formulations, i e the compositions, preparation or mixtures comprising the compound (active ingredient) of formula I or at least one compound of formula I and generally one or more solid or liquid formulation adjuvant(s), are prepared in known manner, e g by intimately mixing and/or grinding the active ingredients with the formulation adjuvants, e g solvents or solid carriers Surface-active compounds (surfactants) may additionally be used in the preparation of the formulations Examples of solvents and solid carriers are given, for example, in WO 97/34485 on page 6.
Depending upon the nature of the compound of formula I to be formulated, suitable surface- active compounds are non-ionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties
Examples of suitable anionic, non-ionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8
Also suitable for the preparation of the herbicidal compositions according to the invention are the surfactants conventionally employed in formulation technology described inter alia in "Mc Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp , Ridgewood New Jersey, 1981 , Stache, H , "Tensid-Taschenbuch", Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J Ash, "Encyclopedia of Surfactants", Vol l-lll, Chemical Publishing Co , New York, 1980-81
The herbicidal formulations generally contain from 0 1 to 99 % by weight, especially from 0 1 to 95 % by weight, of herbicide, from 1 to 99 9 % by weight, especially from 5 to 99 8 % by weight, of a solid or liquid formulation adjuvant and from 0 to 25 % by weight, especially from 0.1 to 25 % by weight, of a surfactant Whereas commercial products will preferably be formulated as concentrates, the end user will normally employ dilute formulations The compositions may also comprise further auxiliaries, such as stabilisers, e g vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rape oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and tackifiers as well as fertilisers or other active ingredients
The compounds of formula I are generally applied to the plants or to their locus in rates of application of from 0 001 to 4 kg/ha, especially from 0 005 to 2 kg/ha The concentration required to achieve the desired effect can be determined by experimentation It is dependent upon the type of action, the stage of development of the crop plant and of the weed, and also upon the application (place, time, method) and, in dependence upon those parameters, can vary within wide limits
The compounds of formula I are distinguished by herbicidal and growth-inhibiting properties which enable them to be used in crops of useful plants, especially in cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and in non- selective weed control Crops are also to be understood as including those which have been rendered tolerant to herbicides or classes of herbicide by conventional methods of breeding or genetic engineering The weeds to be controlled may be either monocotyledonous or dicotyledonous weeds, for example Stellaria, Nasturtium, Agrostis, Digitaπa, Avena, Setaria, Sinapis, Lohum, Solanum, Echmochloa, Scirpus, Monochoπa, Sagittaπa, Bromus, Alopecurus, Sorghum halepense, Rottboelha, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Gahum, Viola and Veronica
The following Examples illustrate the invention further but do not limit the invention
Preparation Examples:
Example P1 : Preparation of C,C,C-trifluoro-N-[3-(4-methanesulfonyl-2-nitro-benzoyl)-4-oxo- bicyclo 3.2.1loct-2-en-2-yl1-methanesulfonamide:
Figure imgf000028_0001
0.25 g (1 .8 mmol) of trifluoromethylsulfonamide is added to a 55 % dispersion of 0.16 g (3.6 mmol) of sodium hydride in oil in 5 ml of anhydrous N-methylpyrrolidone, and the mixture is heated to a temperature of 50°C. Once the evolution of hydrogen has ceased, 0.64 g (1.6 mmol) of 4-chloro-3-(4-methanesulfonyl-2-nitro-benzoyl)-bicyclo[3.2.1]oct-3-en-2- one (e.g. known from JP 06025144 A2) is added in portions and the mixture is stirred for one hour at a temperature of 50°C. The reaction mixture is then acidified with 0.5N hydrochloric acid and subsequently extracted with ethyl acetate in the presence of a small amount of sodium chloride solution. The product, which is dried over sodium sulfate and concentrated by evaporation, is recrystallised from a 1 :1 mixture of dichloromethane and hexane to yield the pure C,C,C-trifluoro-N-[3-(4-methanesulfonyl-2-nitro-benzoyl)-4-oxo- bicyclo[3.2.1]oct-2-en-2-yl]-methanesulfonamide having a melting point of 178-180°C.
Example P2: Preparation of N-f2-(4-methanesulfonyl-2-nitro-benzoyl)-3-oxo-cyclohex-1 - envH-methanesulfonamide:
Figure imgf000028_0002
1 g (2.96 mmol) of 3-amino-2-(4-methanesulfonyl-2-nitro-benzoyl)-cyclohex-2-enone (m.p. 137-138°C, prepared by treatment of 3-chloro-2-(4-methanesulfonyl-2-nitro-benzoyl)- cyclohex-2-enone (m.p. 149-150°C, prepared analogously to DE-A-42 41 999) with 25% ammonia solution at room temperature in tetrahydrofuran) is placed in 10 ml of anhydrous dimethylformamide. 0.81 g (4 43 mmol) of sodium bistrimethylsilylamide is then added in portions After stirring for 30 minutes, 0.28 ml (3.55 mmol) of methanesulfonyl chloride is added dropwise and the mixture is stirred for a further 8 hours. The reaction mixture is then poured into ethyl acetate and 1 N hydrochloric acid, and the organic phase is separated off, washed with water, dried over sodium sulfate and concentrated by evaporation. The residue that remains behind is chromatographed on silica gel using a mixture of toluene, ethyl alcohol, dioxane, triethylamine and water (100:40:20:20:5 parts by volume) as eluant. The resulting oil is dissolved in ethyl acetate and washed in succession with 10 % hydrochloric acid and water. Concentration of the dried organic solution by evaporation yields pure N-[2- (4-methanesulfonyl-2-nιtro-benzoyl)-3-oxo-cyclohex-1 -enyl]-methane-sulfonamιde in the form of crystals having a melting point of 191 -192°C.
Table 1 : Compounds of formula Id:
Figure imgf000029_0001
Figure imgf000029_0002
Figure imgf000030_0002
Table 2: Compounds of formula le
Figure imgf000030_0001
Figure imgf000031_0001
Table 3: Compounds of formula If:
Figure imgf000032_0001
Figure imgf000032_0002
Figure imgf000033_0002
Table 4: Compounds of formula Iq:
Figure imgf000033_0001
Figure imgf000033_0003
Figure imgf000034_0002
Table 5: Compounds of formula Ih:
Figure imgf000034_0001
Figure imgf000034_0003
Figure imgf000035_0001
Table 6 Compounds of formula Ik
Figure imgf000036_0001
Figure imgf000036_0002
Figure imgf000037_0001
Figure imgf000038_0002
Table 7: Compounds of formula Im:
Figure imgf000038_0001
Figure imgf000039_0001
Figure imgf000040_0002
Table 8: Compounds of formula In:
Figure imgf000040_0001
Figure imgf000040_0003
Figure imgf000041_0002
Table 9: Compounds of formula Ip:
Figure imgf000041_0001
Figure imgf000041_0003
Figure imgf000042_0001
Table 10: Compounds of formula Iq:
Figure imgf000043_0001
Figure imgf000043_0002
Figure imgf000044_0002
Table 1 1 : Compounds of formula Ir:
Figure imgf000044_0001
Figure imgf000044_0003
Figure imgf000045_0001
Table 12: Compounds of formula Is:
Figure imgf000046_0001
Figure imgf000046_0002
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Biological Examples
Example B1 : Herbicidal action before emergence of the plants (pre-emerqence action) Monocotyledonous and dicotyledonous test plants are sown in standard soil in plastiG pots. Immediately after sowing, an aqueous suspension (prepared from a 25 % wettable powder (Example F3, b) according to WO 97/34485) or an emulsion (prepared from a 25 % emulsifiable concentrate (Example F1 , c)) of the test compounds is applied by spraying at a rate of application corresponding to 250 g a.i./ha (500 litres water/ha). The test plants are then cultivated in a greenhouse under optimum conditions. After 3 weeks the test is evaluated in accordance with a scale of nine ratings (1 = total damage, 9 = no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action.
Table B1 : Pre-emergence action of the compounds of formula I:
Figure imgf000049_0002
The same results are obtained when the compounds of formula I are formulated in accordance with Examples F2 and F4 to F8 according to WO 97/34485.
Example B2: Post-emergence herbicidal action
Monocotyledonous and dicotyledonous test plants are raised in a greenhouse in plastic pots containing standard soil and at the 4- to 6-leaf stage are sprayed with an aqueous suspension of the test compounds of formula I (prepared from a 25 % wettable powder (Example F3, b) according to WO 97/34485) or with an emulsion of the test compounds of formula I (prepared from a 25 % emulsifiable concentrate (Example F1 , c) according to WO 97/34485) at a rate of application corresponding to 250 g a.i./ha (500 litres water/ha). The test plants are then grown on in the greenhouse under optimum conditions. After about 18 days the test is evaluated in accordance with a scale of nine ratings (1 = total damage, 9 = no action). Ratings of from 1 to 4 (especially from 1 to 3) indicate good to very good herbicidal action. In this test too, the compounds of formula I exhibit strong herbicidal action.
Table B2: Post-emergence action of the compounds of formula I:
Figure imgf000050_0001

Claims

What is claimed is
1 A compound of formula
Figure imgf000051_0001
wherem X is methine, nitrogen or N=0, m is 1 , 2, 3 or 4, each R is independently hydrogen, d-C6alkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6-alkynyl, C2-C6haloalkynyl, C3-C6cycloalkyl, C C6alkoxy, CrC6haloalkoxy, Cι-C6alkylthιo, d-C6alkylsulfιnyl, d-dalkylsulfonyl, d-C6haloalkyl, d-C6haloalkylthιo, d-C6haloalkyl- sulfmyl, d-C6haloalkylsulfonyl, d-C6alkoxycarbonyl, d-C6alkylcarbonyl, Cι-C6alkylamιno, dι-Cι-C6alkylamιno, d-C6alkylamιnosulfonyl, dι-d-C6alkylamιnosulfonyl, -N(R )-S-R2, -N(R3)-S0-R4, -N(R5)-S02-R6, nitro, cyano, halogen, hydroxy, ammo, formyl, hydroxy- d-C6alkyl, d-Cβalkoxy-d-Cealkyl, d-C6alkoxycarbonyloxy-Cι-C6alkyl, d-C6alkylthιo- d-C6alkyl, Cι-C6alkylsulfιnyl-Cι-C6alkyl, Cι-C6alkylsulfonyl-C C6alkyl, rhodano-d-C6alkyl, cyano-C C6alkyl, oxiranyl, C3-C6alkenyloxy, C3-C6alkynyloxy, d-C6alkoxy-Cι-C6alkoxy- d-C3alkyl, d-dalkoxy-d-Cβalkoxy, cyano-Cι-C6alkenyloxy, C C6alkoxycarbonyloxy- Cι-C6alkoxy, C3-C6alkynyloxy, cyano-C C6alkoxy, d-Cealkoxycarbonyl-d-Cealkoxy- Cι-C3alkyl, d-Cealkoxycarbonyl-CrCεalkoxy, d-dalkylthio-d-Cealkoxy, d-C6alkylthιo- Ci-Cεalkoxy-C Csalkyl, alkoxycarbonyl-Cι-C6alkylthιo, alkoxycarbonyl-d-C6alkylthιo-d-C3- alkyl, alkoxycarbonyl-C C6alkylsulfinyl, alkoxycarbonyl-d-C6alkylsulfιnyl-d-C3alkyl, alkoxycarbonyl-C Cealkylsulfonyl, alkoxycarbonyl-d-Cealkylsulfonyl-d-djalkyl, Cι-C6- alkylsulfonyloxy, d-C6haloalkylsulfonyloxy, phenyl, benzyl, phenoxy, phenylthio, phenylsulfinyl, phenylsulfonyl, benzylthio, benzylsulfinyl or benzylsulfonyl, wherein the phenyl and benzyl groups may themselves be mono-, di- or tπ-substituted by d-C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, d-C6-alkoxy, d-C6haloa!koxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, d-C6alkylthιo, C C6- haloalkylthio, C3-C6alkenylthιo, C3-C6haloalkenylthιo, C3-C6alkynylthιo, C2-C5alkoxyalkylthιo, C -C5acetylalkylthιo, C3-C6alkoxycarbonylalkylthιo, C2-C4cyanoalkylthιo, CrCealkylsulfmyl, d-C6haloalkylsulfιnyl, d-C6alkylsulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, d-C2- alkylaminosulfonyl, C2-C4dιalkylamιnosulfonyl, R7-Cι-C3alkylene-, NR8R9, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein those phenylthio and benzylthio groups may themselves be substituted on the phenyl ring by d-C3alkyl, d-C3haloalkyl, C C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, or each R is independently a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system either being bonded directly to the ring containing the substituent X or being bonded to the ring containing the substituent X by way of a d-C4alkylene group, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tπ-substituted by C C6alkyl, d-
C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, d-C6alkoxy, Ci-
C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, Cι-C6alkylthιo, d-C6halo- alkylthio, C3-C6alkenylthιo, C3-C6haloalkenylthιo, C3-C6alkynylthιo, C2-C5alkoxyalkylthιo,
C3-C5acetylalkylthιo, C3-C6alkoxycarbonylalkylthιo, C2-C4cyanoalkylthιo, d-C6alkylsulfιnyl,
Cι-C6haloalkylsulfιnyl, Cι-C6alkylsulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, C C4alkyl- aminosulfonyl, d-C dιalkylamιnosulfonyl, R10-Cι-C3alkylene, NR^ R^, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, C C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents at the nitrogen atom in the heterocyclic ring are free of halogen;
R R3 and R5 are each independently of the others hydrogen or d-C6alkyl,
R2 ιs NR13R14, C C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl,
C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may itself be substituted by
Cι-C alkyl, d-C3haloalkyl, Cι-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro,
R4 is NRι5R16, d-C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl,
C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may itself be substituted by
Cι-C3alkyl, CrC3haloalkyl, d-C3alkoxy, Cι-C3haloalkoxy, halogen, cyano or by nitro,
R6 ιs NR17R18, Cι-C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C3-C6alkynyl,
C3-C6haloalkynyl, C3-C6cycloalkyl or phenyl, wherein phenyl may itself be substituted by
C C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro,
R7 and R10 are each independently of the other Cι-C3alkoxy, C2-C4alkoxycarbonyl, d-C3- alkylthio, d-C3alkylsulfιnyl, d-C3alkylsulfonyl or phenyl, wherein phenyl may itself be substituted by d-C3alkyl, C C3haloalkyl, Cι-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro;
R8, Rn, R13, Ri5 and R17 are each independently of the others d-Cι2alkyl;
R9, R12, R14, R16 and R18 are each independently of the others d-d∑alkyl, or R8 and R9 together, and/or Rn and R 2 together, and/or R 3 and R14 together, and/or R15 and R16 together, and/or R,7 and R18 together, with the nitrogen atom to which they are bonded, form a 3- to 7-membered ring;
Q is the group Q^
Figure imgf000053_0001
wherein
R19 is hydrogen or Cι-C6alkyl;
R20 is Cι-Cι2alkyl, d-C12haloalkyl, C2-C12alkenyl, C2-C6haloalkenyl, d-C2alkoxycarbonyl- or phenyl-substituted vinyl, or is C3-C6alkynyl, C3-C6haloalkynyl, C3-C6allenyl, C3-C6cycloalkyl,
NR32R33, benzyl or phenyl, wherein the phenyl-containing groups may themselves be substituted by d-C3alkyl, C C3- haloalkyl, d-C3alkoxy, d-C3haloaIkoxy, halogen, cyano or by nitro, or R20 is hydroxy-
Cι-C12alkyl, d-dalkoxy-d-dsalkyl, d-C4alkylthio-C C12alkyl, d-C4alkylsulfinyl-d-C12- alkyl, Cι-C alkylsulfonyl-Cι-Cι2alkyl, cyano-d-d2alkyl, d-Cealkylcarbonyloxy-d-d∑-alkyl, d-C alkoxycarbonyl-d-Cι2alkyl, Cι-C alkoxycarbonyloxy-d-C12alkyl, rhodano-d-Cι2alkyl, benzoyloxy-Cι-C12alkyl, C2-C6oxiranyl, Cι-C4alkylamino-d-C12alkyl, di(d-C4alkyl)amino-
Cι-Cι2alkyl, d-C^alkylthiocarbonyl-d-C^alkyl or formyl-d-C12alkyl; or R20 is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the
-N(Rι9)-S(0)2- group by way of a d-Cι2alkylene group, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tri-substituted by Cι-C6alkyl, d-C6haloalkyl, C2-C6alkenyl,
C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, d-C6alkoxy, d-C6haloalkoxy, C3-C6- alkenyloxy, C3-C6alkynyloxy, mercapto, d-C6alkylthio, d-C6haloalkylthio, C3-C6alkenylthio, C3-C6haloalkenylthιo, C3-C6alkynylthιo, C2-C5alkoxyalkylthιo, C3-C5acetylalkylthιo, C3-C6- alkoxycarbonylalkylthio, C2-C4cyanoalkylthιo, d-C6alkylsulfιnyl, d-C6haloalkylsulfιnyl, Cι-C6alkylsulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, d-C2alkylaminosulfonyl, dι(d-C2- alkyl)amιnosulfonyl, dι(d-C4alkyl)amιno, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by Cι-C3alkyl, d-C3haloalkyl, d-C3alkoxy, C C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen atom in the hetero-cyclic ring are other than halogen,
R21, R22, R23 and R2 are each independently of the others hydrogen, d-C6alkyl, d-C6- haloalkyl, C2-C6alkenyl, C2-C6alkynyl, d-C6aikoxycarbonyl, d-C6alkylcarbonyl, C C6- alkylthio, C C6alkylsulfιnyl, d-C6alkylsulfonyl, d-C6alkyl-NHS(0)2, d-C6alkylamιno, di- (Cι-C6alkyl)amιno, hydroxy, d-C6alkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, hydroxy-d-C6- alkyl, C1-C4alkylsulfonyloxy-C1-C6alkyl, tosyloxy-d-C6alkyl, halogen, cyano, nitro, phenyl or phenyl substituted by d-C4alkyl, C C haloalkyl, d-C4alkoxy, d-C haloalkoxy, d-C4alkyl- carbonyl, Cι-C4alkoxycarbonyl, ammo, Cι-C4alkylamιno, dι-Cι-C4alkylamιno, d-C6alkylthιo, d-C6alkylsulfιnyl, d-C6alkylsulfonyl, Cι-C4alkylsulfonyloxy, d-C6haloalkylthιo, CrC6- haloalkylsulfmyl, Cι-C6haloalkylsulfonyl, C C haloalkylsulfonyloxy, d-C4alkyl-S(0)2NH, C1-C6alkylthιo-N(C1-C4alkyl), C C6alkylsulfιnyl-N(Cι-C4alkyl), C C6alkylsulfonyl-N(CrC4- alkyl), halogen, nitro, COOH or by cyano, or R24 and R21 together or R22 and R23 together denote C2-C6alkylene, C(0)OCH2CH2-, C(0)OCH2CH2CH2-, S-C2-C4alkylene, S(0)-C2-C4- alkylene or S(0)2-C2-C alkylene,
W is oxygen, sulfur, sulfmyl, sulfonyl, -CR25, R26-, -C(O)-, -CR28R29-CR30R31- or -NR27-, wherein the carbon atom carrying the substituents R28R2g is attached to the carbon atom carrying the substituents R22R23,
R25 is hydrogen, d-C alkyl, Cι-C4haloalkyl, d-C alkoxy-d-C4alkyl, Cι-C4alkylthιo-CrC4- alkyl, CrC alkylthιo-C3-C6cycloalkyl, d-C4alkylcarbonyloxy-d-C4alkyl, C C4alkylsulfonyl- oxy-C C4alkyl, tosyloxy-C C4alkyl, dι(Cι-C3alkoxyalkyl)methyl, dι(Cι-C3alkylthιoalkyl)- methyl, (CrC3alkoxyalkyl)-(d-C3alkylthιoalkyl)methyl, C3-C5oxacycloalkyl, C3-C5thιacyclo- alkyl, C3-C4dιoxacycloalkyl, C3-C4dιthιacycloalkyl, C3-C4oxathιacycloalkyl, formyl, Cι-C4- alkoxycarbonyl, carbamoyl, Cι-C alkylamιnocarbonyl, dι(d-C alkyl)amιnocarbonyl, phenylammocarbonyl, benzylammocarbonyl or phenyl which may itself be substituted by d-C4alkyl, d-C4haloalkyl, C C4alkoxy, C1-C haloalkoxy, d-C alkylcarbonyl, C C - alkoxycarbonyl, ammo, C1-C4alkylamιno, dι-Cι-C4alkylamιno, Cι-C4alkylthιo, C C alkyl- sulfmyl, C1-C4alkylsulfonyl, d-C4alkylsulfonyloxy, d-C4haloalkylthιo, d-C4haloalkylsulfιnyl, d-C4haloalkylsulfonyl, d-C4haloalkylsulfonyloxy, d-C4alkyl-S(0)2NH, d-C6alkylthιo-
N(d-C4alkyl), C1-C6alkylsulfιnyl-N(C1-C4alkyl), C1-C6alkylsulfonyl-N(C1-C4alkyl), halogen, nitro, COOH or by cyano, or R26 together with R23 or R24 denotes d-C5alkylene,
R26 is hydrogen, C1-C4alkyl or C C4haloalkyl, or R26 together with R25 denotes C2-C6- alkylene,
R27 is hydrogen, Cι-C4alkyl, C C4alkoxycarbonyl or phenyl which may itself be substituted by Cι-C4alkyl, C C4haloalkyl, C C4alkoxy, C C4haloalkoxy, Cι-C4alkylcarbonyl, Cι-C4- alkoxycarbonyl, C1-C4alkylamιno, dι-d-C4alkylamιno, Cι-C4alkylthιo, Cι-C4alkylsulfιnyl, d-C4alkylsulfonyl, C1-C4alkylsulfonyloxy, C C4haloalkylthιo, C C4haloalkylsulfιnyl, Cι-C4- haloalkylsulfonyl, d-C4haloalkylsulfonyloxy, d-C4alkyl-S(0)2NH, C1-C4alkyl-S(0)2N(C1-C4- alkyl), halogen, nitro or by cyano,
R28, R29, R30 and R31 are each independently of the others hydrogen or d-C6alkyl, or R26 or
R28 or R30 together with R21 or R23 form a direct bond,
R32 is d-Cι2alkyl,
R33 is Cι-C12alkyl, or R32 and R33 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring, with the proviso that R20 is other than d-C12alkyl and d-C haloalkyl when X is nitrogen or
NO, the group -C(0)-Q occupies the 3-posιtιon in the ring and R in the 6-posιtιon in the ring is d-C6haloalkyl, or Q is the group Q2
Figure imgf000055_0001
wherein
R3 is hydrogen or d-C6alkyl,
R35 is C Cι2alkyl, C C12haloalkyl, C2-Cι2alkenyl, C2-C6haloalkenyl, Cι-C2alkoxycarbonyl- or phenyl-substituted vinyl, or is C3-C6alkynyl, C3-C6haloalkynyl, C3-C6allenyl, C3-C6cycloalkyl,
NR51R52, benzyl or phenyl, wherein the phenyl-contaming groups may themselves be substituted by C C3alkyl, d-C3- haloalkyl, Cι-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, or R35 is hydroxy- d-C12alkyl, d-dalkoxy-d-dsalkyl, Cι-C4alkylthio-Cι-C12alkyl, d-C^lkylsulfinyl-d-C^- alkyl, Cι-C4alkylsulfonyl-d-C12alkyl, cyano-d-C1 alkyl, d-Cealkylcarbonyloxy-d-C^alkyl,
Cι-C4alkoxycarbonyl-d-Cι2alkyl, C1-C4alkoxycarbonyloxy-d-C12alkyl, rhodano-d-C12alkyl, benzoyloxy-d-C12alkyl, C2-C6oxiranyl, Cι-C4alkylamino-d-Cι2alkyl, di(Cι-C4alkyl)amino-
Cι-C12alkyl, Cι-C12alkylthiocarbonyl-d-C12alkyl or formyl-d-C12alkyl; or R35 is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the
-N(R34)-S(0)2- group by way of a Cι-C12alkylene group, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tri-substituted by d-C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6- haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, Cι-C6alkoxy, Cι-C6haloalkoxy, C3-C6alkenyloxy,
C3-C6alkynyloxy, mercapto, Cι-C6alkylthio, Cι-C6haloalkylthio, C3-C6alkenylthio, C3-C6halo- alkenylthio, C3-C6alkynylthio, C2-C5alkoxyalkylthio, C3-C5acetylalkylthio, C3-C6alkoxy- carbonylalkylthio, C2-C4cyanoalkylthio, C C6alkylsulfinyl, d-C6haloalkylsulfinyl, Cι-C6alkyl- sulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, Cι-C2alkylaminosulfonyl, di(d-C2alkyl)- aminosulfonyl, di(Cι-C4alkyl)amino, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by
Cι-C3alkyl, d-C3haloalkyl, d-C3alkoxy, Cι-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents on the nitrogen atom in the hetero-cyclic ring are other than halogen;
Y is a chemical bond, an alkylene group A^ carbonyl, oxygen, sulfur, sulfinyl, sulfonyl,
-NR40 or NH(CO)R41 ;
Figure imgf000056_0001
A is C(R44R45)r ; r and m0ι are each independently of the other 0, 1 or 2;
R36 is hydrogen, methyl or C C3alkoxycarbonyl;
R37, R38, R39, R-M, R45, R42 and R 3 are each independently of the others hydrogen, d-C - alkoxy, Cι-C4alkylthio, Cι-C4alkylsulfinyl, Cι-C4alkylsulfonyl, halogen or methyl, or R39 together with an adjacent group R45 or R43 denotes a chemical bond;
R40 and R4ι are each independently of the other hydrogen or C C4alkyl;
R51 is d-Cι2alkyl; and R52 is Cι-C12alkyl, or R51 and R52 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring, with the proviso that R34 is C5-C6alkyl when R35 is d-C alkyl or C C haloalkyl and X is nitrogen or NO, or Q is the group Q3
Figure imgf000057_0001
R50 wherein
R46 is hydrogen or d-C6alkyl,
R 7 is d-C12alkyl, Cι-C12haloalkyl, C2-C12alkenyl, C2-C6haloalkenyl, d-C2alkoxycarbonyl- or phenyl-substituted vinyl, or is C3-C6alkynyl, C3-C6haloalkynyl, C3-C6allenyl, C3-C6cycloalkyl, NR53R54, benzyl or phenyl, wherein the phenyl-containmg groups may themselves be substituted by C C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, or R 7 is hydroxy-Cι-C12alkyl, d-C4alkoxy-d-C12alkyl, Cι-C4alkylthιo-CrCi2alkyl, C C4alkylsulfιnyl-C1-C1 alkyl, C1-C4alkylsulfonyl-CrC12alkyl, cyano-d-C12alkyl, d-C6- alkylcarbonyloxy-Cι-C12alkyl, Cι-C4alkoxycarbonyl-Cι-C12alkyl, Cι-C4alkoxycarbonyloxy- d-C12alkyl, rhodano-C C12alkyl, benzoyloxy-d-Ci∑alkyI, C2-C6oxιranyl, d-C4alkylamιno- Cι-Cι2alkyl, d^d-dalky ammo-d-C^alkyl, d-C12alkylthιocarbonyl-Cι-Cι2alkyl or formyl- d-Cι2alkyl, or R 7 is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the -N(R46)-S(0)2- group by way of a C C12alkylene group, and each ring system may contain no more than two oxygen atoms and no more more than two sulfur atoms, and the ring system itself may be mono-, di- or tπ-substituted by Cι-C6alkyl, d-C6haloalkyl, C2-C6alkenyl, C2-C6haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, d-C6alkoxy, d-C6haloalkoxy, C3-C6- alkenyloxy, C3-C6alkynyloxy, mercapto, d-C6alkylthιo, d-C6haloalkylthιo, C3-C6alkenylthιo, C3-C6haloalkenylthιo, C3-C6alkynylthιo, C2-C5alkoxyalkylthιo, C3-C5acetylaIkylthιo, C3-C6- alkoxycarbonylalkylthio, C2-C4cyanoalkylthιo, d-C6alkylsulfιnyl, d-C6haloalkylsulfιnyl, Cι-C6a!kylsulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, Cι-C2alkylamιnosulfonyl, dι(d-C2- alky!)amιnosulfonyl, dι(Cι-C alkyl)amιno, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents at the nitrogen atom in the heterocyclic ring are free of halogen,
R 8 and R49 are each independently of the other hydrogen, d-C4alkyl, C2-C6alkenyl, C2-C6- alkynyl, C C4alkoxycarbonyl, C C6alkylthιo, d-C6alkylsulfιnyl, d-C6alkylsulfonyl, d-C4- alkyl-NHS(0)2, d-C4haloalkyl, or phenyl which may itself be substituted by d-C4alkyl,
Cι-C4haloalkyl, d-C4alkoxy, C C haloalkoxy, d-C4alkylcarbonyl, d-C alkoxycarbonyl, ammo, Cι-C4alkylamιno, dι-d-C4alkylamιno, d-C6alkylthιo, d-C6alkylsulfιnyl, d-C6- alkylsuifonyl, d-C4alkylsulfonyloxy, C1-C4haloalkylthιo, d-C4haloalkylsulfιnyl, Cι-C4- haloalkylsulfonyl, d-C4haloalkylsulfonyloxy, C C4alkyl-S(0)2NH, C C4alkyl-S(0)2N(C C4- alkyl), halogen, nitro, COOH or by cyano, or R48 and R 9 together form a C -C6alkylene bridge, and
R50 ιs hydrogen, d-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, d-C4alkoxycarbonyl, benzyl or phenyl, wherein benzyl or phenyl may themselves be substituted by d-C alkyl, d-
C4haloalkyl, Cι-C4alkoxy, d-C -haloalkoxy, Cι-C4alkylcarbonyl, d-C alkoxycarbonyl, am o, d-C alkylamιno, dι-Cι-C -alkylamιno, d-C4alkylthιo, C1-C4alkylsulfιnyl, d-C4alkylsulfonyl, d-C alkylsulfonyloxy, d-C4haloalkylthιo, d-C haloalkylsulfιnyl, C C4haloalkylsulfonyl, Cι-C4haloalkylsulfonyloxy, d-C4alkyl-S(0)2NH, d-C4alkyl-S(0)2N(d-C4alkyl), halogen, nitro, COOH or by cyano,
R53 is d-C12alkyl and
R54 is d-Cι2alkyl, or R53 and R54 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring, with the proviso that R46 is C5-C6alkyl when R47 is Cι-C4alkyl or C C4haloalkyl and X is nitrogen or NO; or Q is the group Q
Figure imgf000058_0001
wherein R60 is hydrogen or d-C6alkyl,
R6ι is Cι-C12alkyl, d-Cι2haloalkyl, C2-C12alkenyl, C2-C6haloalkenyl, d-C2alkoxycarbonyl- or phenyl-substituted vinyl, or is C3-C6alkynyl, C3-C6haloalkynyl, C3-C6allenyl, C3-C6cycloalkyl, NR62R63, benzyl or phenyl, wherein the phenyl-contaming groups may themselves be substituted by d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, or R61 is hydroxy-d-C12alkyl, C1-C4alkoxy-C C12alkyl, d-C alkylthιo-d-Cι2alkyl, Cr C4alkylsulfιnyl-C1-C12alkyl, Cι-C4alkylsulfonyl-C1-C12alkyl, cyano-d-C12alkyl, C C6- alkylcarbonyloxy-d-C^alkyl, d-C4alkoxycarbonyl-Cι-C12alkyl, d-C alkoxycarbonyloxy- Cι-C12alkyl, -rhodano-Cι-d2alkyl, benzoyloxy-Cι-Cι2alkyl, C2-C6oxιranyl, d-C4alkylamιno-d- Cι2alkyl,
Figure imgf000059_0001
d-C12alkylthιocarbonyl-Cι-C12alkyl or formyl- d-C12alkyl, or R61 is a five- to ten-membered monocyclic or fused bicyclic ring system, which may be aromatic or partially saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, the ring system being bonded to the sulfur atom of the -N(R60)-S(O)2- group by way of a d-d2alkylene group, and each ring system may contain no more than two oxygen atoms and no more than two sulfur atoms, and the ring system itself may be mono-, di- or tπ-substituted by Cι-C6alkyl, Cι-C6haloalkyl, C2-C6alkenyl, C2-C6- haloalkenyl, C2-C6alkynyl, C2-C6haloalkynyl, Cι-C6alkoxy, d-C6haloalkoxy, C3-C6alkenyloxy, C3-C6alkynyloxy, mercapto, C C6alkylthιo, d-C6haloalkylthιo, C3-C6alkenylthιo, C3-C6halo- alkenylthio, C3-C6alkynylthιo, C2-C5alkoxyalkylthιo, C3-C5acetylalkylthιo, C3-C6alkoxy- carbonylalkylthio, C2-C4cyanoalkylthιo, d-C6alkylsulfιnyl, d-C6haloalkylsulfιnyl, C C6- alkylsulfonyl, d-C6haloalkylsulfonyl, aminosulfonyl, d-C2alkylamιnosulfonyl, dι(d-C2- alkyl)amιnosulfonyl, dι(C1-C4alkyl)amιno, halogen, cyano, nitro, phenylthio and/or by benzylthio, wherein phenylthio and benzylthio may themselves be substituted on the phenyl ring by d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C3haloalkoxy, halogen, cyano or by nitro, and wherein the substituents at the nitrogen atom in the heterocyclic ring are free of halogen;
R62 is Cι-C12alkyl and
R63 is Cι-C12alkyl, or R62 and R63 together with the nitrogen atom to which they are bonded form a 3- to 7-membered ring, Yi is oxygen or NR59;
R59 is hydrogen, d-C6alkyl, C3-C6alkenyl, C3-C6alkynyl, d-C4alkoxycarbonyl, benzyl or phenyl, wherein benzyl or phenyl may themselves be substituted by d-C6alkyl, d- C6haloalkyl, d-C6alkoxy, d-C6-haloalkoxy, d-C6alkylcarbonyl, d-C6alkoxycarbonyl, ammo, Cι-C4alkylamιno, C1-C4-dιalkylamιno, CrC6alkylthιo, d-C6alkylsulfιnyl, Cι-C6alkylsulfonyl, d- C4alkylsulfonyloxy, d-C4haloalkylthιo, C1-C4haloalkyisulfιnyl, d-C4haloalkylsulfonyl, C1-C4haloalkylsulfonyloxy, d-C4alkyl-S(0)2NH, Ci-C4alkyl-S(0)2N(d-C4alkyl), halogen, nitro, COOH or by cyano, R55, s6, R57 and R58 are each independently of the others hydrogen, hydroxy-d-C4alkyl, C-i- C6alkyl, C1-C4alkoxy-C1-C4alkyl, C2-C6alkenyl, C2-C6alkynyl, d-C6alkoxycarbonyl, d-C6- alkylthio, Cι-C6alkylsulfιnyl, d-C6alkylsulfonyl, d-C4alkylamιnosulfonyl, d-C4haloalkyl, d-Cβalkylsulfonyloxy-d-dalkyl, phenylsulfonyloxy-d-C4alkyl, d-C6alkylamιno, CrC6- dialkylamino, d-C6alkoxy or phenyl, wherein the phenyl group may itself be substituted by Cι-C4alkyl, CrC4haloalkyl, Cι-C4alkoxy, C C4haloalkoxy, C C4alkylcarbonyl, d-C4- alkoxycarbonyl, halogen, nitro, COOH or by cyano, or R55 and R56 together form a C2-C5- alkylene chain, or R55 and R57 together form a chemical bond or a CrC4alkylene chain, or R57 together with R59 forms a chemical bond or a C3-C4alkylene chain; or an agrochemically tolerable salt or any stereoisomer or tautomer of a compound of formula I
2. A herbicidal and plant-growth-mhibitmg composition that comprises a herbicidally effective amount of a compound of formula I on an inert carrier.
3. A method of controlling undesired plant growth, which comprises applying a herbicidally effective amount of a compound of formula I or of a composition comprising that compound to the plants or to their locus.
4. A method of inhibiting plant growth, which comprises applying a herbicidally effective amount of a compound of formula I or of a composition comprising that compound to the plants or to their locus
5. The use of a composition according to claim 2 in controlling undesired plant growth
PCT/EP2001/002581 2000-03-09 2001-03-07 Acylated phenyl or pyridine herbicides WO2001066522A1 (en)

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