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WO2003087067A1 - Aryl-alkyne compounds as herbicides - Google Patents

Aryl-alkyne compounds as herbicides Download PDF

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Publication number
WO2003087067A1
WO2003087067A1 PCT/EP2003/003467 EP0303467W WO03087067A1 WO 2003087067 A1 WO2003087067 A1 WO 2003087067A1 EP 0303467 W EP0303467 W EP 0303467W WO 03087067 A1 WO03087067 A1 WO 03087067A1
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WIPO (PCT)
Prior art keywords
dalkyl
substituted
mono
hydrogen
tri
Prior art date
Application number
PCT/EP2003/003467
Other languages
French (fr)
Inventor
Jürgen Schaetzer
Marian Valentiny
Gerald Wayne Craig
Jean Wenger
Kurt Nebel
André Stoller
Roger Graham Hall
Original Assignee
Syngenta Participations Ag
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Publication date
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Priority to CA002481008A priority Critical patent/CA2481008A1/en
Priority to US10/510,223 priority patent/US20050202973A1/en
Priority to AU2003222793A priority patent/AU2003222793A1/en
Priority to BR0308983-5A priority patent/BR0308983A/en
Priority to EP03718726A priority patent/EP1507768A1/en
Publication of WO2003087067A1 publication Critical patent/WO2003087067A1/en

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    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D237/14—Oxygen atoms
    • C07D237/16—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/18—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D253/075—Two hetero atoms, in positions 3 and 5
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links

Definitions

  • the present invention relates to novel, herbicidally active phenyl- and pyridyl-alkynes, to processes 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.
  • Phenylalkynes having herbicidal action are described, for example, in JP-A-11 147866, WO 01/55066 and WO 02/28182.
  • the present invention accordingly relates to compounds of formula
  • phenyl independently is phenyl which may in turn be mono- to penta-substituted by halogen or by C C alkyl or mono-, di- or tri-substituted by C ⁇ -C haloalkyl, C ⁇ -C alkoxy, -CN, -NO 2l C C alkylthio, CrC 4 alkylsulfinyl or by d-C 4 alkylsulfonyl; or, when Q is a group Q 1 ( Q 2 , Q 3 or Q 5 , two adjacent R 1 substituents may together form a d-C 7 alkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which may be mono- to penta-substituted by halogen or by C ⁇ -C 6 alkyl or mono-, di- or tri-substituted by C ⁇ -C 6 alkoxy, the total number of ring atoms being at least 5 and at most 9; or
  • R 3 or R are each independently of the other hydrogen, halogen, -CN, C C 4 alkyl or
  • R 3 and R 4 together are C 2 -C 5 alkylene
  • R 5 is hydrogen or C C 8 alkyl
  • R 6 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C ⁇ -C 4 alkyl or mono-, di- or tri-substituted by C ⁇ -C haloalkyl, C C 4 alkoxy, -CN, -NO 2> CrC 4 alkylthio,
  • R 5 and R 6 together are a C 2 -C 5 alkylene chain which may be interrupted by " an oxygen or sulfur atom;
  • R 7 is hydrogen, C C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is C C 8 alkyl, C 3 -C 8 alkenyl or
  • C C 4 alkoxy or by phenyl it being possible for phenyl in turn to be mono- to penta- substituted by halogen or by CrC 4 alkyl or mono-, di- or tri-substituted by CrC 4 haloalkyl, C C 4 alkoxy, -CN, -NO 2) C C 4 alkylthio, C C alkylsulfinyl or by CrC 4 alkylsulfonyl; R 8 is hydrogen or C ⁇ -C 8 alkyl;
  • R 9 is hydrogen or CrC 8 alkyl, or is C C 8 alkyl mono-, di- or tri-substituted by -COOH, CrC 8 alkoxycarbonyl or by -CN, or
  • Rg is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C ⁇ -C alkyl or mono-, di- or tri- substituted by C C 4 haloalkyl, CrC 4 alkoxy, -CN, -NO 2 , C C 4 alkylthio, d-C 4 alkylsulfinyl or by CrC alkylsulfonyl; or R 8 and R g together are C 2 -C 5 alkylene; R 10 is hydrogen, CrC 4 alkyl, C C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • Rn is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C C 4 haloalkyl or C 3 -C 6 haloalkenyl;
  • R 12 is hydrogen, CrC 4 alkyl, C C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • R 13 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl; or
  • R 13 is phenyl or phenyl-C C 6 alkyl, it being possible for the phenyl ring in turn to be mono- to penta-substituted by halogen or by C ⁇ -C alkyl or mono-, di- or tri-substituted by C C halo- alkyl, CrC 4 alkoxy, -CN, -NO 2 , CrC 8 alkylthio, CrC 8 alkylsulfinyl or by CrC 8 alkylsulfonyl, or R13 is C ⁇ -C 8 alkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, CrC 6 aIkylamino, di(CrC 6 alkyl)amino or by C r C 4 alkoxy;
  • R ⁇ 4 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is CrC 8 alkyl mono- to penta- substituted by halogen or mono-, di- or tri-substituted by -CN or by CrC alkoxy;
  • R 1 5, R 16 and R 17 are each independently of the others C r C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or C C 8 alkyl mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by C ⁇ -C 4 alkoxy;
  • R ⁇ s is hydrogen or d-Caalkyl;
  • R 19 is hydrogen, C C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C 1 -C 4 a!kyl or mono-, di- or tri-substituted by CrC 4 haloalkyl, C r C 4 alkoxy, -CN, -NO 2 , C C 4 alkylthio, CrC 4 alkylsulfinyl or by CrC 4 alkylsulfonyl; or
  • R 18 and R ⁇ g together are a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom;
  • R 20 is hydrogen, C ⁇ -C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C ⁇ -C 4 alkyl or mono-, di- or tri-substituted by C r C 4 haloalkyl, C C 4 alkoxy, -CN, -NO 2 , C C 4 alkylthio, CrC 4 alkylsulfinyl or by CrC 4 alkylsulfonyl; R 2 ⁇ is hydrogen or CrC 8 alkyl; R 22 is hydrogen or CrC 8 alkyl, or is C C 8 alkyl mono-, di- or tri-substituted by -COOH, C C 8 alkoxycarbonyI or by -CN, or
  • R 22 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by CrC 4 alkyl or mono-, di- or tri- substituted by CrOjhaloalkyl, C C 4 alkoxy, -CN, -NO 2 , CrC 4 alkylthio, C r C 4 alkylsulfinyl or by CrC 4 aIkylsulfonyI; or R 21 and R 22 together are C 2 -C 5 alkylene; R 23 is hydrogen, C C 4 alkyl, C C 4 haloalkyl or C 3 -C 6 cycloalkyl; R 2 is hydrogen, C C 4 alkyl, C C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • R 25 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C ⁇ -C haloalkyl or C 3 -C 6 haloalkenyl;
  • R 26 is hydrogen or CrC 8 alkyl;
  • R 27 is hydrogen or CrC 8 alkyl, or is CrC 8 alkyl mono-, di- or tri-substituted by -COOH, C C 8 - alkoxycarbonyl or by -CN, or
  • R 27 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by CrC 4 alkyl or mono-, di- or tri- substituted by C C 4 haloalkyl, C C 4 alkoxy, -CN, -NO 2 , C C 4 alkylthio, C C 4 alkylsulfinyl or by C ⁇ -C 4 alkylsulfonyl; or R 26 and R 27 together are C 2 -C 5 alkylene; R 28 is hydrogen or d-C 8 alkyl;
  • R 29 and R 30 are each independently of the other hydrogen, CrCsalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or C ⁇ -C 8 alkyl mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by d-C 4 alkoxy;
  • R 4 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by CrC 4 alkyl or mono-, di- or tri-substituted by CrC 4 haloalkyl, d-C 4 alkoxy, -CN, -N0 2 , d-C 4 alkylthio, CrC alkylsulfinyl or by C r C 4 alkylsulfonyl; or
  • R 33 and R 34 together are a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom;
  • R 35 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is C C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by C ⁇ -C alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta- substituted by halogen or by CrC 4 alkyl or mono-, di- or tri-substituted by C C haloalkyl, C C 4 alkoxy, -CN, -NO 2 , CrC 4 alkylthio, C C 4 alkylsulfinyl or by d-C 4 alkylsulfonyl; R 36 is hydrogen or d-C 8 alkyl;
  • R 37 is hydrogen or CrC 8 alkyl, or is CrC 8 alkyl mono-, di- or tri-substituted by -COOH, C C 8 - alkoxycarbonyl or by -CN, or
  • R3 7 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by CrC alkyl or mono-, di- or tri- substituted by C C 4 haloalkyl, C C 4 alkoxy, -CN, -NO 2 , C r C 4 alkylthio, C ⁇ -C 4 alkylsulfinyl or by C ⁇ -C 4 alkylsulfonyl; or R 36 and R 37 together are C 3 -C 5 alkylene; R 38 is hydrogen, CrC 4 alkyl, C ⁇ -C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • R 39 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C C 4 haloalkyl or C 3 -C 6 haloalkenyI;
  • R 40 is hydrogen, C 1 -C 4 alkyl, d-C 4 haloalkyl, C C 8 alkylthio, -C(O)-C(O)Od-C 4 alkyl or C 3 -C 6 - cycloalkyl;
  • R 4 ⁇ is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-Cealkoxy-d-Cealkyl, C C 8 alkyl- carbonyl, d-C 8 alkoxycarbonyl, C 3 -C 8 alkenyloxycarbonyl, d-Cealkoxy-Ci-Cealkoxycarbonyl, d-Cealkylthio-CrCealkyl, CrC 6 alkylsulfinyl-C ⁇ -C 6 alkyl or d-Cealkylsulfonyl-d-Cealkyl; or R is phenyl or phenyl-d-C 6 alkyl, it being possible for the phenyl ring in turn to be mono- to penta-substituted by halogen or by d-C 4 alkyl or mono-, di- or tri-substituted by
  • R ⁇ is C ⁇ -C 8 alkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -COOH, CrC 8 alkoxycarbonyl, d-C 6 alkylamino, di(d-C 6 alkyl)amino or by -CN;
  • R 42 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is d-C 8 alkyl mono- to penta- substituted by halogen or mono-, di- or tri-substituted by -CN or by d-C alkoxy;
  • R ⁇ and R 4 are each independently of the other d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or C C 8 alkyl mono- to penta-substituted by halogen or mono-, di- or tri-sub
  • R 5 is C C 8 alkyl, C C 8 alkyl mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by d-C alkoxy, or is C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or R 45 is phenyl, it being possible for the phenyl ring to be mono- to penta-substituted by halogen or by C C 4 alkyl or mono-, di- or tri-substituted by CrC 4 haloalkyl, d-C 4 alkoxy, -CN, NO 2 , d-C 8 alkylthio, d-C 8 alkylsulfinyl or by C ⁇ -C 8 alkylsulfonyl; R 46 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl or d-C
  • CrC 4 alkoxy C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is C r C 8 alkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, d-C 4 alkoxy, d-C 8 alkoxycarbonyl, -NH 2 , CrC 4 alkylamino, di(d-C 4 alkyl)amino, -NR 48 COR 49) -NR 50 SO 2 R 51
  • R 7 is phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta- substituted by halogen or by C C 4 alkyl or mono-, di- or tri-substituted by C C 4 haloalkyl, d-C 4 alkoxy, -CN, -NO 2 , d-C 4 aikylthio, d-C alkylsulfinyl or by C ⁇ -C 4 alkylsulfonyl; p is 0 or 1 ;
  • R 8 , R 49 , R 50 , R51, R52 and R 53 are each independently of the others hydrogen, d-C 8 alkyl, phenyl, benzyl or naphthyl, it being possible for the three last-mentioned aromatic radicals in turn to be mono- to penta-substituted by halogen or by d-C 8 alkyl or mono-, di- or tri- substituted by d-C 4 haloalkyl, d-C 4 alkoxy, C C 4 alkylamino, di(C ⁇ -C 4 alkyl)amino, -NH 2 , -CN, -NO 2 , d-C 4 alkylthio, C C 4 alkylsulfinyl or by C ⁇ -C alkylsulfonyl;
  • R 5 and R 55 are each independently of the other hydrogen, d-C 8 alkyl, or phenyl which may in turn be mono- to penta-substituted by halogen or by C ⁇ -C alkyl or mono-, di- or tri- substituted by C C haloalkyl, d-C alkoxy, -CN, -NO 2 , d-C ⁇ alkylthio, d-C 8 alkylsuifinyl or by d-C 8 alkylsulfonyl;
  • R 56 is hydrogen, d-C 8 alkyl, CrC 4 haloalkyl, d-C 4 alkoxy, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl or benzyl, it being possible for benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-C 4 haloalkyl, C C 4 aIkoxy, -CN, -NO 2 , d-Csalkylthio, C C 8 alkylsulfinyl or by C C 8 alkylsulfonyl;
  • R 5 is CrC 8 alkyl, d-C haloalkyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono- to penta-substituted by halogen or by C r C 4 alkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, d-C 4 alkylamino, di(d-C 4 alkyl)amino, -NH 2 , -CN, -NO 2 , d-dalkylthio, d-C 4 alkylsulfinyl or by C ⁇ -C 4 alkylsulfonyl; R 58 and R 5 g are each independently of the other d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl, benzyl or naphthyl, it being possible
  • R 60 and R 6 ⁇ are each independently of the other hydrogen or d-C 6 alkyl
  • Re 2 , R ⁇ 3 and R 64 are each independently of the others hydrogen or d-C 8 alkyl, or
  • R 63 and R 64 together form a C 2 -C 5 alkylene bridge
  • Res, Ree, Re7, Res, es and R 70 are each independently of the others hydrogen or d-C 8 alkyl, or
  • each R 2 independently is C C 8 alkyl substituted by a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from oxygen, nitrogen and sulfur, it being possible for that heterocyclic ring system in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, hydroxy-C 1 -C 4 alkyl, C ⁇ -C 4 alkoxy,
  • each R 2 independently is C 2 -C 8 alkenyl, or is C 2 -C 8 alkenyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -NO 2 , -CO 2 R 94 , -CONR 95 R 96 , -COR 97 ,
  • each R 2 independently is C 3 -C 6 cycloalkyl, or is C 3 -C 6 cycloalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -CO 2 Rn6 > -CONRn 7 R 118 , -COR 119 ,
  • R 72 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-C alkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-C alkylthio, d-dalkylsulfinyl or by d-C alkylsulfonyl; or
  • R 71 and R 72 together are a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom;
  • R 73 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta- substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-C haloalkyl, d-dalkoxy, -CN, -NO 2 , d-C 4 alkylthio, C C 4 alkylsulfinyl or by d-dalkylsulfonyl; R 74 is hydrogen or CrC 8 alkyl;
  • R 75 is hydrogen, C ⁇ -C 8 alkyl or C 3 -C 7 cycloalkyl, or is C ⁇ -C 8 alkyl mono-, di- or tri-substituted by -COOH, C C 8 alkoxycarbonyl, C ⁇ -C 6 alkoxy or by -CN; or
  • R 75 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C ⁇ -C 4 alkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by Crdalkylsulfonyl; or
  • R 74 and R 75 together are a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom;
  • R 76 is hydrogen, C ⁇ -C alkyl, C C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • Rrr is hydrogen, d-C 4 alkyl, d-C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • R 78 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-dhaloalkyl or C 3 -C 6 haloalkenyl;
  • R 79 is hydrogen or d-C 8 alkyl
  • Rso is hydrogen or C C 8 alkyl, or is C C 8 alkyl mono-, di- or tri-substituted by -COOH, C C 8 - alkoxycarbonyl or by -CN; or
  • R 80 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C C alkyl or mono-, di- or tri- substituted by C 1 -C 4 haloalkyl, d-C 4 alkoxy, -CN, -NO 2 , Crdalkylthio, C C 4 alkylsulfinyl or by C ⁇ -C alkylsulfonyl; or R 79 and R 80 together are C 2 -C alkylene; R 8 ⁇ is hydrogen or CrC 8 alkyl;
  • R 82 is -Si(CrC 6 alkyl) 3 , C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is C C 8 alkyl which is mono- to penta- substituted by halogen or mono-, di- or tri-substituted by -CN, -NH 2 , d-C 6 alkylamino, di(C ⁇ -C 6 alkyl)amino or by d-dalkoxy;
  • R 83 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is C C 8 alkyl which is mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -NH 2 , d-C 6 alkylamino, di(C ⁇ -C 6 alkyl)amino or by d-dalkoxy;
  • R 84 , R 85 and R 86 are each independently of the others C C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 - alkynyl, or d-C 8 alkyl which is mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by d-dalkoxy;
  • R 8 and R 89 are each independently of the other hydrogen, C C 8 alkyl or d-C 8 alkoxy;
  • R 88 is d-C 8 aIkyl;
  • R 90 is hydrogen or d-C 8 alkyl;
  • R 9 ⁇ is d-dalkyl;
  • R 92 and R 93 are each independently of the other d-C 6 alkyl
  • R 94 is hydrogen or is d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, each of which may be mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta-substituted by halogen or by d-C 4 - alkyl or mono-, di- or tri-substituted by d-C 4 haloalkyl, d-C 4 alkoxy, -CN, -NO 2 , d-dalkylthio, C 1 -C 4 alkylsulfinyl or by d-dalkylsulfonyl; R 95 is hydrogen or C ⁇ -C 8 alkyl;
  • R 96 is hydrogen or d-C 8 alkyl, or is C C 8 alkyl mono-, di- or tri-substituted by -COOH, C ⁇ -C 8 aIkoxycarbonyl or by -CN; or
  • R 96 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by C C 4 haloalkyl, C r C 4 alkoxy, -CN, -NO 2 , C r C 4 alkylthio, C C 4 alkylsulfinyl or by d-dalkylsulfonyl; or R 95 and R 96 together are C 2 -C 5 alkylene;
  • R 97 and R 98 are each independently of the other hydrogen, d-C 4 alkyl, d-C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • R 99 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-dhaloalkyl or C 3 -C 6 haloalkenyl;
  • R 100 is hydrogen or d-C 8 alkyI;
  • R 101 is hydrogen or CrC 8 alkyl, or is d-C 8 alkyl mono-, di- or tri-substituted by -COOH, d-C 8 - alkoxycarbonyl or by -CN; or
  • R 101 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-C 4 ha!oalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfiny! or by d-dalkylsulfonyl; or R 100 and R 101 together are C 2 -C 5 alkylene; Rio 2 is hydrogen or d-C 8 alkyl;
  • R1 0 3 is hydrogen, d-C 8 alkyl, -Si(d-C 6 alkyl) 3 , C 3 -C 8 alkenyl or C 3 -C 8 alkynyl;
  • R ⁇ o 4 is d-dalkyl;
  • R 105 is hydrogen or is C ⁇ -C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, each of which may be mono- to penta-substituted by halogen or mono-, di- or tri-substituted by C C 4 alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, C C 4 alkylsulfinyl or by d-dalkylsulfonyl; 106 is hydrogen or d-C 8 alkyl;
  • R ⁇ 07 is hydrogen or d-C 8 alkyl, or is d-C 8 alkyl mono-, di- or tri-substituted by -COOH, C ⁇ -C 8 alkoxycarbonyl or by -CN, or
  • R107 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-C 4 alkoxy, -CN, -NO 2 , d-dalkylthio, d-C 4 alkylsulfinyl or by d-dalkylsulfonyl; or R 106 and R 107 together are C 2 -C 5 alkylene; R 108 is hydrogen, C ⁇ -C 4 alkyl, d-dhaloalkyl or C 3 -C 6 cycloalkyl; R 109 is hydrogen, d-dalkyl, d-C 4 haloalkyl or C 3 -C 6 cycloalky
  • R 110 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, CrC 4 haloalkyl or C 3 -C 6 haloalkenyl;
  • Rm is hydrogen or d-C 8 alkyl;
  • R ⁇ 12 is hydrogen or C ⁇ -C 8 alkyl, or is CrC 8 alkyl mono-, di- or tri-substituted by -COOH, d-C 8 alkoxycarbonyl or by -CN; or
  • Rii 2 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C C 4 alkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , C C 4 alkylthio, d-C 4 alkylsulfinyl or by d-dalkylsulfonyl; or Rm and Rn 2 together are C 2 -C 5 alkylene; R is hydrogen or d-C 8 alkyl; R 114 is hydrogen, d-C 8 alkyl, -Si(C C 6 alkyl) 3 , C 3 -C 8 alkenyl or C 3 -C 8 alkynyl; R 115 is d-C 6 alkyl
  • R 116 is hydrogen or is d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, each of which may be mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-C 4 alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-C 4 haloalkyl, C 1 -C 4 alkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-C 4 alkylsulfonyl; R 117 is hydrogen or C C 8 alkyl;
  • R ⁇ 18 is hydrogen or d-C 8 alkyl, or is d-C 8 alkyl mono-, di- or tri-substituted by -COOH, d-C 8 alkoxycarbonyl or by -CN; or
  • Rns is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-C 4 alkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R 117 and R ⁇ 18 together are C 2 -C 5 alkylene; R 119 is hydrogen, d-C 4 alkyl, C C 4 haloalkyl or C 3 -C 6 cycloalkyl; R ⁇ 20 is hydrogen, d-C 4 alkyl, C C haIoalkyl or C 3 -C 6 cycloalkyl;
  • R ⁇ 21 is hydrogen, C C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-C 4 haloalkyl or C 3 -C 6 haloalkenyl;
  • R 122 is hydrogen or C ⁇ -C 8 alkyl;
  • R 123 is hydrogen or C ⁇ -C 8 alkyl, or is d-C 8 alkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbony! or by -CN; or
  • Ri 2 3 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-C 4 alkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , C ⁇ -C alkylthio, d-dalkylsulfinyl or by C ⁇ -C 4 alkyIsulfonyl; or R 122 and R ⁇ 23 together are C 2 -C 5 alkylene; and R 124 is hydrogen or C ⁇ -C 8 alkyl, and to the agrochemically acceptable salts and all stereoisomers and tautomers of the compounds of formula I.
  • substituents that are formed as a result of R 5 and R 6 together or R 18 and R ⁇ g together or R 36 and R 37 together or R 74 and R75 together being a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom are piperidine, morpholine, thiomorpholine and pyrrolidine.
  • heterocyclic ring systems which may be aromatic or partially or fully saturated in the definition of R 2 are:
  • alkyl groups appearing in the substituent definitions may be straight-chained or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and the pentyl, hexyl, heptyl and octyl isomers.
  • Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine.
  • Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1 ,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl or 2,2,2- trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl or dichlorofluoromethyl.
  • Alkoxy groups have a chain length of preferably from 1 to 6, especially from 1 to 4, carbon atoms.
  • Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, or the pentyloxy and hexyloxy isomers; preferably methoxy or ethoxy.
  • Alkoxy, alkenyl, alkynyl, alkoxyalkyl, alkylthio, alkylsulfonyl, alkylsulfinyl, alkylaminoalkoxy, alkoxycarbonyl, alkylcarbonyloxy, alkenylthio, alkenylsulfonyl, alkenylsulfinyl, alkynylsulfonyl, alkynylthio and alkynylsulfinyl groups are derived from the mentioned alkyl groups.
  • the alkenyl and alkynyl groups may be mono- or poly-unsaturated.
  • Alkenyl is, for example, vinyl, allyl, methallyl, 1 -methylvinyl or but-2-en-1-yl.
  • Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, 2-methylbutyn-2-yl or but-3-yn-2-yl.
  • Alkylthio groups preferably have a chain length of from 1 to 4 carbon atoms.
  • Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butyl- thio or tert-butylthio, preferably methylthio or ethylthio.
  • Alkylsulfinyl is, for example, methyl- sulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, 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.
  • Alkoxyalkyl groups preferably have from 1 to 6 carbon atoms.
  • Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.
  • the invention relates also to the salts which the compounds of formula I are able to form preferably with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
  • Suitable salt formers are described, for example, in WO 98/41089.
  • alkali metal and alkaline earth metal hydroxides as salt formers, special mention should be made of the hydroxides of lithium, sodium, potassium, magnesium and calcium, especially the hydroxides of sodium and potassium.
  • amines suitable for ammonium salt formation include ammonia as well as primary, secondary and tertiary C ⁇ -C ⁇ 8 alkylamines, C C 4 hydroxyalkylamines and C 2 -C 4 alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropyl- amine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methyl-hexylamine, methyl- nonylamine, methyl-pentadecylamine, methyl-octadecylamine,
  • Preferred quaternary ammonium bases suitable for salt formation correspond, for example, to the formula [N(R a R b R c Rd)]OH wherein R a , R b , c and R d are each independently of the others d-dalkyl.
  • Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.
  • R 3 or R 4 are each independently of the other hydrogen, halogen, -CN, d-dalkyl or d-dalkoxy; or
  • R 3 and R 4 together are C 2 -C 5 alkylene;
  • R 5 is hydrogen or d-dalkyl;
  • R 6 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-C alky(, d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by C C 4 alkylsuIfonyl; or
  • R 5 and R 6 together are a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom;
  • R 7 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is d-dalkyl, C 3 -C 8 a!kenyl or C 3 -C 8 alkynyl mono-, di- or tri-substituted by halogen, d-C 4 alkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R 8 is hydrogen or C C 8 alkyl;
  • R 9 is hydrogen or C r C 8 alkyl, or is d-C 8 alkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
  • Rg is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-C 4 alkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , CrC 4 alkylthio, d-dalkylsulfinyl or by d-C 4 alkylsulfonyl; or R 8 and R 9 together are C 2 -C 5 alkylene; Rio is hydrogen, d-dalkyl, d-dhaloalkyl or C 3 -C 6 cycIoalkyl;
  • R 11 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-dhaloalkyl or C 3 -C 6 haloalkenyl;
  • Ri2 is hydrogen, d-dalkyl, d-dhaloalkyl or C 3 -C 6 cycloalkyl;
  • R13 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl; or
  • Ri3 is phenyl or phenyl-C C 6 alkyl, it being possible for the phenyl ring in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by C C 8 alkylsulfonyl; or
  • R 13 is d-dalkyl mono-, di- or tri-substituted by halogen, -CN, Crdalkylamino, di(Crd- alkyl)amino or by d-C 4 alkoxy;
  • R 14 is hydrogen, d-C 8 alkyl, C 3 ⁇ C 8 alkeny! or C 3 -C 8 alkynyl, or is d-C 8 alkyl mono-, di- or tri- substituted by halogen, -CN or by d-C 4 alkoxy;
  • R15, Rie and R 17 are each independently of the others d-dalky!, C 3 -C 8 alkenyl or C 3 -C 8 - alkynyl, or d-C 8 alkyl mono-, di- or tri-substituted by halogen, -CN or by d-daikoxy;
  • R 18 is hydrogen or d-dalkyl;
  • R 19 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d- dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, Crdalkylsulfinyl or by C dalkylsulfonyl; or
  • R ⁇ 8 and R ⁇ 9 together are a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom;
  • R 20 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d- dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by C r dalkylsuifonyl;
  • R 21 is hydrogen or d-dalkyl
  • R 22 is hydrogen or d-dalkyl, or is d-C 8 alkyl mono-, di- or tri-substituted by -COOH,
  • Rz> is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, C C 4 haloalkyl, d-dalkoxy,
  • R 21 and R 22 together are C 2 -C 5 alkylene
  • R 23 is hydrogen, d-C 4 alkyl, CrC 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • R 24 is hydrogen, CrC 4 alkyl, d-C 4 haloalkyl or C 3 -C 6 cycioalkyl;
  • R 25 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-C 4 haloalkyl or C 3 -C 6 haloalkenyl;
  • R 26 is hydrogen or d-C 8 alkyl
  • R 27 is hydrogen or d-C 8 alkyl, or is d-dalky! mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
  • R 27 is d-dalkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C 4 haloalkyl, d-dalkoxy,
  • R 26 and R 27 together are C 2 -C 5 alkylene
  • R 28 is hydrogen or d-dalkyl
  • R 29 and R 30 are each independently of the other hydrogen, d-dalkyl, C 3 -C 8 alkenyl or
  • R 31 and R 32 are each independently of the other d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or d-C 8 alkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy; m is O, 1 , 2, 3 or 4; each R 2 independently is hydrogen, halogen, -CN, -SCN, -OCN, -N 3 , -SF 5 , -NO 2 , -NRssR ⁇ ,
  • R 35 is a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being
  • Ru is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, Crdalkylsulfinyl or by d- dalkylsulfonyl; or
  • R 33 and R 34 together are a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom;
  • R 35 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -dalkynyl mono-, di- or tri-substituted by halogen, d-C 4 alkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-C 4 alkoxy, -CN, -NO 2> d-dalkylthio, Crdalkylsulfinyl or by d-dalkylsulfonyl; R 36 is hydrogen or d-dalkyl;
  • R 37 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
  • R 37 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C haloalkyl, d-C alkoxy, -CN, -NO 2 , d-C 4 alky!thio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R 36 and R 37 together are C 3 -C 5 alkylene; R 38 is hydrogen, d-dalkyl, d-dhaloalkyl or C 3 -C 6 cycloalkyl;
  • R 39 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-dhaloalkyl or C 3 -C 6 haloalkenyl;
  • R 40 is hydrogen, d-daikyl, d-dhaloalkyl, C C 8 alkylthio, -C(O)-C(O)Od-C 4 alkyl or C 3 -C 6 cycloalkyl;
  • R 4 ⁇ is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, CrC 6 alkoxy-CrC 6 alkyl, C C 8 alkyl- carbonyl, d-C 8 alkoxycarbonyl, C 3 -C 8 alkenyloxycarbonyl, CrC 6 alkoxy-CrC 6 alkoxycarbonyl, CrC 6 alkylthio-CrC 6 alkyl, Crdalkylsulfinyl-d-dalkyl or CrC 6 alkylsuifonyl-CrC 6 alkyl; or R 4 1 is phenyl or phenyl-d-dalkyl, it being possible for the phenyl ring in turn to be mono-, di- or tri-substituted by halogen, C C 4 alkyl, C r C 4 haloalkyl, d-dalkoxy, -CN, -
  • R 2 is hydrogen, CrC 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is d-C 8 alkyl mono-, di- or tri- substituted by halogen, -CN or by d-C 4 alkoxy;
  • R 3 and R are each independently of the other d-C 8 alkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or d-dalkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy;
  • R 45 is d-dalkyl, d-C 8 alkyl mono-, di- or tri-substituted by halogen, -CN or by d-C 4 alkoxy, or is d-C 8 alkenyl or C 3 -C 8 alkynyl, or
  • R 5 is phenyl, it being possible for the phenyl ring to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
  • R 46 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl or d-dhaloalkyl;
  • R 47 is hydrogen, d-dalkyl, d-dalkoxy, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is d-dalkyl mono-, di- or tri-substituted by halogen, -CN, C C 4 alkoxy, d-C 8 alkoxycarbonyl, -NH 2 , C C 4 alkylamino, di(C C 4 alkyl)amino, -NR 48 COR 49 , -NR 50 SO 2 R 5 ⁇ or by.
  • -NR 52 CO 2 R 53 , or R47 is phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri- substituted by halogen, d-dal
  • R 48 , R 49 , R 5 o, R5 1 , R52 and R 53 are each independently of the others hydrogen, d-dalkyl, phenyl, benzyl or naphthyl, it being possible for the three last-mentioned aromatic radicals in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dalkylamino, di(d-C 4 alkyl)amino, -NH 2 , -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
  • R 54 and R 55 are each independently of the other hydrogen, d-dalkyl, or phenyl which may in turn be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C 4 haloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
  • R 56 is hydrogen, d-dalkyl, d-C 4 haloalkyl, d-dalkoxy, C 3 -C 8 alkenyl, C 3 -C 8 aikynyl or benzyl, it being possible for benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO
  • R57 is d-dalkyl, d-dhaloalkyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono-, di- or tri-substituted by halogen, d-dalkyl, C dhaloalkyl, d-dalkoxy, d-C 4 aIkylamino, di(CrC 4 alky!)amino, -NH 2 , -CN, -NO 2) d- dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R 58 and R 59 are each independently of the other d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono-, di- or tri-substitute
  • Reo and R 6 ⁇ are each independently of the other hydrogen or d-dalkyl;
  • R 62 , R6 3 and R 64 are each independently of the others hydrogen or d-dalkyl, or R 63 and R 64 together form a C 2 -C 5 alkylene bridge;
  • Res, Ree, Re7, Res, Res and R 7 o are each independently of the others hydrogen or d-dalkyl, or
  • R 72 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , C C 4 alkylthio, Crdalkylsulfinyl or by C dalkylsulfonyl; or
  • R 7 ⁇ and R 72 together are a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom;
  • R 73 is hydrogen, Crdalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is d-dalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R 74 is hydrogen or d-dalkyl;
  • R 75 is hydrogen, -dalkyl or C 3 -C 7 cycloalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl, d-dalkoxy or by -CN; or
  • R 75 is C ⁇ -dalkenyl, d-dalkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -N0 2 , d-dalkylthio, d-C 4 alky.sulfl.1yl or by d-dalkylsulfonyl; or R 7 and R 75 together are a C 2 -C 5 alkylene chain which may be interrupted by an oxygen or sulfur atom;
  • R 7 e is hydrogen, d-dalkyl, d-dhaloalkyl or C 3 -C 6 cycloalkyl
  • R77 is hydrogen, d-dalkyl, d-dhaloalkyl or C 3 -C 6 cycloalkyl
  • R 78 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-C 4 haloalkyl or d-dhaloalkenyl;
  • R 79 is hydrogen or d-dalkyl
  • R 8 o is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
  • R ⁇ o is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-C 4 alkoxy, -CN, -N0 2 , d-dalkylthio, d-dalkylsulfinyl or by C C 4 alkylsulfonyl; or R 79 and R 80 together are C 2 -C 5 alkylene; R 8 ⁇ is hydrogen or d-dalkyl; R 8 is -Si(C ⁇ -C 6 alkyl) 3 , C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, or is d-dalkyl which is mono-, di- or tri- substituted by halogen, -CN
  • R 84 , Res and R 86 are each independently of the others d-dalkyl, C 3 -C 8 alkenyl or C 3 -C 8 - alkynyl, or d-C 8 alkyl which is mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy;
  • R 87 and R 89 are each independently of the other hydrogen, d-dalkyl or d-C 8 alkoxy; R 88 is d-dalkyl; R 90 is hydrogen or d-dalkyl; R 91 is d-dalkyl;
  • R 92 and Rg 3 are each independently of the other d-dalkyl
  • R 94 is hydrogen or is d-dalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, each of which may be mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, - CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R 95 is hydrogen or d-dalkyl;
  • R 96 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
  • R 96 is C -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R 95 and R 96 together are C 2 -C 5 alkylene;
  • R 97 and R 98 are each independently of the other hydrogen, d-dalkyl, d-C 4 haloalkyl or d-C 6 cycloalkyl;
  • R 99 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-dhaloalkyl or C 3 -C 6 haloalkenyl; Rioo is hydrogen or d-dalkyl;
  • R 101 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-C 8 alkoxycarbonyl or by -CN; or
  • R 1 0 1 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C 4 haloalkyl, d-dalkoxy, -CN, -NO 2 , d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; 0 r R 10 o and R 10 ⁇ together are C 2 -C 5 alkylene; R 102 is hydrogen or d-dalkyl; R 103 is hydrogen, d-dalkyl, -Si(CrdalkyI) 3 , C 3 -C 8 alkenyl or C 3 -C 8 alkynyl; R 10 is d-dalkyl;
  • R 1 05 is hydrogen or is d-dalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, each of which may be mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-C alkoxy, -
  • R 10 e is hydrogen or d-dalkyl
  • R 10 7 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
  • R 10 7 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy,
  • R 10 6 and R107 together are C 2 -C 5 alkylene
  • R 108 is hydrogen, d-dalkyl, d-dhaloalkyl or C 3 -C 6 cycloalkyl;
  • R109 is hydrogen, d-dalkyl, d-dhaloalkyl or C 3 -C 6 cycloalkyl;
  • R ⁇ 10 is hydrogen, C C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, d-dhaloalkyl or C 3 -C 6 haloalkenyl;
  • Rm is hydrogen or d-dalkyl
  • R 112 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
  • R1 1 2 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, Crdalkyl, d-C 4 haloalkyl, d-dalkoxy,
  • Rm and R together are C 2 -C 5 alkylene
  • R 11 3 is hydrogen or d-dalkyl
  • R 114 is hydrogen, d-dalkyl, -Si(d-C 6 alkyl) 3 , C 3 -C 8 alkenyl or C 3 -C 8 alkynyl;
  • R 115 is d-dalkyl
  • R 116 is hydrogen or is Crdalkyl, C 3 -C 8 alkenyl or C 3 -C 8 alkynyl, each of which may be mono-, di- or tri-substituted by halogen, d-C 4 aikoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -
  • R 117 is hydrogen or d-dalkyl
  • R 118 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
  • R 118 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, Crdalkyl, d-dhaloalkyl, d-dalkoxy,
  • R 117 and R 118 together are C 2 -C 5 alkylene;
  • R 119 is hydrogen, C C 4 alkyl, C r C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • R ⁇ 2 o is hydrogen, C 1 -C al yl, d-C 4 haloalkyl or C 3 -C 6 cycloalkyl;
  • R1 21 is hydrogen, d-dalkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C C 4 haloalkyl or C 3 -C 6 haloalkenyl;
  • R1 22 is hydrogen or d-dalkyl
  • R1 23 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
  • R 123 is C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy,
  • R ⁇ 22 and R 123 together are C 2 -C alkylene
  • R ⁇ 24 is hydrogen or Crdalkyl.
  • R ⁇ R 2 , R 3 , R 4 , Z, m and n are as defined for formula I, can be prepared analogously to known methods described, for example, in "Palladium in Heterocyclic Chemistry” from Tetrahedron Organic Chemistry Series 20, A Guide for the Synthetic Chemist, Editors Jie Jack Li and Gordon W. Gribble, Pergamon 2000, Tetrahedron Lett. 1986 (27), 1171 ; Tetrahedron Organic Chemistry 2000 (20), 359-362; ibid. 2000 (20), 390- 394; and K. Sonogashira in Comprehensive Organic Synthesis, Editors I. Fleming et ai, Oxford 1991 , Vol. 3, page 521 ff., for example by reacting a compound of formula lla
  • R 3 and R are as defined for formula I and M + is an alkali metal cation such as, for example, a lithium, sodium or potassium cation, to form a compound of formula IVa
  • Z, R 2 and m are as defined for formula I and A is a leaving group such as, for example, halogen or trifluoromethanesulfonate, in the presence of a palladium catalyst.
  • Q is a group Q 3 , that is to say compounds of formula lc
  • Q is a group Q 5 , that is to say compounds of formula le
  • the compounds of formula la can be obtained, for example, by reaction of substituted propargyl ethers of formula IVa with compounds of formula V by means of Sonogashira coupling.
  • the propargyl ethers of formula IVa can, for their part, be obtained by a nucleophilic aromatic substitution reaction of compounds of formula lla wherein X is halogen with alcoholates of formula Ilia.
  • Suitable catalyst mixtures are, for example, tetrakis(triphenylphosphine)palladium or bis(triphenylphosphine)palladium(ll) dichloride together with copper(l) iodide (Cul);
  • suitable bases are preferably amines, for example triethylamine, diethylamine or diisopropylethylamine.
  • the phenyl or pyridine derivatives of formula V preferably have a leaving group A, A being, for example, halogen or trifluoromethanesulfonate (Tetrahedron Organic Chemistry 2000 (20), 209-213; J. Org. Chem. 1998 (63), 8551-8553) and Tetrahedron Lett. 1986(27), 1171.
  • Solvents used for the Sonogashira reaction are usually ethers, for example tetrahydrofuran, chlorinated hydrocarbons, for example chloroform, or dipolar aprotic solvents, for example dimethylformamide or dimethyl sulfoxide, and also amines, for example triethylamine or piperidine.
  • lla M + alkali metal ion, e.g. Na + IVa
  • X halogen base, e.g. NaH solvent, e.g. THF
  • the compounds of formula I can also be obtained by further methods such as, for example, that shown in Reaction Scheme 3.
  • Activation of the alcohol of formula VII according to Reaction Scheme 3 is carried out, for example, by sulfonylation or halogenation.
  • Sulfonylation of the alcohol of formula VII is a standard reaction and can be carried out, for example, using a sulfonic acid chloride, for example mesyl chloride or para-toluenesulfonic acid chloride (p-TosCI), in the presence of a tertiary amine, e.g. triethylamine, or an aromatic amine, e.g. pyridine, in a solvent such as, for example, a chlorinated hydrocarbon, e.g. carbon tetrachloride or methylene chloride, or an amine, e.g. pyridine.
  • a sulfonic acid chloride for example mesyl chloride or para-toluenesulfonic acid chloride (p-TosCI)
  • a tertiary amine e.g. triethylamine
  • an aromatic amine e.g. pyridine
  • solvent such as, for example, a chlorinated hydro
  • Halogenation of the alcohol of formula VII can be carried out in analogy to standard methods. For example, bromination can be successfully carried out using carbon tetrabromide in the presence of triphenylphosphine (Synthesis 1998, 1015-1018) in methylene chloride. Chlorination can be successfully carried out using mineral acids, for example using concentrated hydrochloric acid (J. Org. Chem.
  • Suitable solvents are dimethylformamide or acetonitrile; suitable bases are preferably potassium carbonate or 1 ,8-diazabicylo[5.4.0]undec-7-ene (DBU).
  • DBU 1 ,8-diazabicylo[5.4.0]undec-7-ene
  • the etherification can also be carried out in halogenated or aromatic hydrocarbons as solvent, for example in chloroform or in benzene, in the presence of silver carbonate as base.
  • Such selective O-alkylation reactions in the presence of a ring nitrogen atom are described, for example, in Synth. Commun. 1994 (24), 1367 and Heterocycles 1990 (31), 819.
  • the reactions resulting in the compounds of formula I are advantageously performed in aprotic, inert, organic solvents.
  • solvents are hydrocarbons, such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons, such as dichloromethane, trichloro- methane, tetrachloromethane or chlorobenzene, ethers, such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles, such as acetonitrile or propionitrile, amides, such as N,N-dimethylformamide, diethyl- formamide or N-methylpyrrolidinone.
  • the reaction temperatures are preferably from -20°C to +120°C.
  • the reactions are generally slightly exothermic and can usually be carried out at room temperature.
  • heating, up to the boiling point of the reaction mixture may, where appropriate, be carried out for a short time. It is also possible for the reaction times to be reduced by adding a few drops of base as reaction catalyst.
  • Suitable bases are especially tertiary amines, such as trimethylamine, triethylamine, quinuclidine, 1 ,4-diazabicyclo[2.2.2]octane, 1 ,5-diaza- bicyclo[4.3.0]non-5-ene or 1 ,5-diazabicyclo[5.4.0]undec-7-ene.
  • bases inorganic bases such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, carbonates, e.g. sodium carbonate or potassium carbonate, or hydrogen carbonates, e.g. potassium hydrogen carbonate or sodium hydrogen carbonate.
  • the compounds of formula I may, in conventional manner, be isolated by concentrating and/or evaporating off the solvent and purified by recrystallising or triturating the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
  • the compounds of formulae IV (and IVa to IVf) and VII are novel. The present invention accordingly relates also to those compounds.
  • the compounds of formula I may be used as herbicides in their unmodified form, that is to say as obtained in the synthesis, but they are preferably formulated in customary manner together with the adjuvants conventionally employed in formulation technology, for example into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
  • Such formulations are described, for example, on pages 9 to 13 of WO 97/34485.
  • 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, preparations or mixtures comprising the compound (active ingredient) of formula I, or at least one compound of formula I, and, usually, one or more solid or liquid formulation adjuvants, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredient(s) with the formulation adjuvants, for example solvents or solid carriers.
  • formulation adjuvants for example solvents or solid carriers.
  • Surface-active compounds surfactants
  • solvents and solid carriers are given, for example, on page 6 of WO 97/34485.
  • suitable surface- active compounds are non-ionic, cationic and/or anionic surfactants and surfactant mixtures having good emulsifying, dispersing and wetting properties.
  • suitable anionic, non-ionic and cationic surfactants are listed, for example, on pages 7 and 8 of WO 97/34485.
  • 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 especially from 0.1 to 25 % by weight
  • compositions may also comprise further ingredients, such as stabilisers, for example vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), anti-foams, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers, and also fertilisers or other active ingredients.
  • stabilisers for example vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), anti-foams, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers, and also fertilisers or other active ingredients.
  • the compounds of formula I are generally applied to the plant or the locus thereof at 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 experiment. It is dependent on the nature of the action, the stage of development of the cultivated plant and of the weed and on the application (place, time, method) and may vary within wide limits as a function of those parameters.
  • the compounds of formula I are distinguished by herbicidal and growth-inhibiting properties, allowing them to be used in crops of useful plants, especially cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and also for non-selective weed control.
  • crops of useful plants especially cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and also for non-selective weed control.
  • crops is to be understood as including also crops that have been made tolerant to herbicides or classes of herbicides as a result of conventional methods of breeding or genetic engineering techniques.
  • the weeds to be controlied may be either monocotyledonous or dicotyledonous weeds, such as, for example, Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Panieum, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Euphorbia, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
  • Stellaria Nasturtium, Agrostis, Digitaria, Avena, Setaria, Panieum, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Euphorbia, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum hal
  • a mixture of 9.9 ml (0.1 mol) of methoxyacetic acid methyl ester and 8.1 ml (0.1 mol) of ethyl formate is added dropwise to a stirred suspension of 2.3 g (0.1 mol) of sodium in 30 ml of toluene, the temperature being kept below 30°C.
  • the toluene phase is decanted off and 15 ml of ethanol and 7.6 g (0.1 mol) of thiourea are added to the crude, viscous sodium salt of 3-hydroxy-2-methoxyacrylic acid methyl ester.
  • the resulting mixture is stirred at 20°C for 1 hour and is then heated at reflux temperature for 5 hours.
  • the solid formed is dissolved in 50 ml of water and the resulting solution is rendered neutral with 6N hydrochloric acid.
  • the desired title compound precipitates out and can, after drying at 100°C, be obtained in a yield of 8.3 g (52 % of theory).
  • the product can be further used directly for further reactions.
  • 0.23 ml (0.0038 mol) of propargyl alcohol is added to a suspension of 0.155 g (0.0038 mol) of sodium hydride (60 % suspension in oil) in 5 ml of N.N-dimethylformamide, whilst cooling with ice-water, and the resulting mixture is stirred at 20°C for 30 minutes. Then, 0.55 g (0.003 mol) of 2,5-dichloro-3-methoxy-pyrazine (Example P9) is added, whilst cooling in an ice-water bath, and the mixture is stirred further at 20°C for 3 hours. The reaction is stopped by adding ethyl acetate and water, and the aqueous phase is extracted with ethyl acetate.
  • the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate.
  • the crude product obtained is purified on a silica gel column (eluant: ethyl acetate/isohexane 1/9).
  • the desired title compound having a melting point of 71-72°C, is obtained in a yield of 0.23 g (53 % of theory), and 0.07 g (17 % of theory) of the isomeric 2-chloro-3-methoxy-5-prop-2-ynyloxy-pyrazine is obtained.
  • the reaction mixture is stirred at 20°C for 90 minutes.
  • the reaction is stopped by adding ice, and the aqueous phase is extracted three times, using 10 ml of ethyl acetate each time.
  • the combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated.
  • the crude product obtained is purified on a silica gel column (eluant: ethyl acetate/isohexane 1/3). 0.20 g (38 % of theory) of the desired title compound, having a melting point of 99-100°C, is obtained.

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Abstract

Compounds of formula (I) wherein Q is a group formula (II), (III); Z is=N-, formula (IV) or =C(R2)-; n is 0, 1, 2 or 3; R3 or R4 are each independently of the other hydrogen, alogen, -CN, C1-C4alkyl or C1-C4alkoxyl; or R3 and R4 together are C2-C5alkylene; and the agrochemically acceptable salts and all stereoisomers and tautomers of the compounds of formula (I) are suitable for use as herbicides.

Description

ARY -A KYNE COMPOUNDS AS HERBICIDES
The present invention relates to novel, herbicidally active phenyl- and pyridyl-alkynes, to processes 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.
Phenylalkynes having herbicidal action are described, for example, in JP-A-11 147866, WO 01/55066 and WO 02/28182.
Novel phenyl- and pyridyl-alkynes that have herbicidal and growth-inhibiting properties have now been found.
The present invention accordingly relates to compounds of formula
Figure imgf000003_0001
wherein Q is a group
Figure imgf000003_0002
Figure imgf000003_0003
Z is =N-> }, + ~ or =C(R2)- : n is O, 1, 2 or 3; each Ri independently is halogen, -CN, -SCN, -SF5, -NO2, -NR5R6, -CO2R7, -CONR8R9,
-C(Rιo)=NORιι, -CORi2) -OR13, -SR14, -SOR15, -SO2Rι6, -OSO2R17, CrC8alkyl, C2-C8alkenyl, C2-C8alkynyl or C3-C6cycloalkyl; or is CrCsalkyl, C2-C8alkenyl or C2-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -NO2, -NR18R19, -CO2R20, -CONR2ιR22, -COR23, -C(R24)=NOR25, -C(S)NR26R2 , -C(Cι-C4alkylthio)=NR28, - OR29) -SR30, -SOR31, -SO2R32 or by C3-C6cycloalkyl; or each Ri independently is C3-C6cycloalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -NO2, -NRι8Rι9, -CO2R20,
Figure imgf000004_0001
-C(S)NR26R27, -C(C C4alkylthio)=NR28, -SR30, -SOR31, -SO2R32 or by C3-C6cycloalkyl; or each R. independently is phenyl which may in turn be mono- to penta-substituted by halogen or by C C alkyl or mono-, di- or tri-substituted by Cι-C haloalkyl, Cι-C alkoxy, -CN, -NO2l C C alkylthio, CrC4alkylsulfinyl or by d-C4alkylsulfonyl; or, when Q is a group Q1 ( Q2, Q3 or Q5, two adjacent R1 substituents may together form a d-C7alkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which may be mono- to penta-substituted by halogen or by Cι-C6alkyl or mono-, di- or tri-substituted by Cι-C6alkoxy, the total number of ring atoms being at least 5 and at most 9; or, when Q is a group Q1, Q2, Q3 or Q5, two adjacent Ri substituents may together form a C2-C7alkenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which may be mono- to penta-substituted by halogen or by CrC6alkyl or mono-, di- or tri-substituted by C C6alkoxy, the total number of ring atoms being at least 5 and at most 9;
R3 or R are each independently of the other hydrogen, halogen, -CN, C C4alkyl or
Cι-C4alkoxy; or
R3 and R4 together are C2-C5alkylene;
R5 is hydrogen or C C8alkyl;
R6 is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by Cι-C4alkyl or mono-, di- or tri-substituted by Cι-C haloalkyl, C C4alkoxy, -CN, -NO2> CrC4alkylthio,
CrC4alkylsulfinyl or by CrC4alkylsulfonyl; or
R5 and R6 together are a C2-C5alkylene chain which may be interrupted by "an oxygen or sulfur atom;
R7 is hydrogen, C C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or is C C8alkyl, C3-C8alkenyl or
C3-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by
C C4alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta- substituted by halogen or by CrC4alkyl or mono-, di- or tri-substituted by CrC4haloalkyl, C C4alkoxy, -CN, -NO2) C C4alkylthio, C C alkylsulfinyl or by CrC4alkylsulfonyl; R8 is hydrogen or Cι-C8alkyl;
R9 is hydrogen or CrC8alkyl, or is C C8alkyl mono-, di- or tri-substituted by -COOH, CrC8alkoxycarbonyl or by -CN, or
Rg is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by Cι-C alkyl or mono-, di- or tri- substituted by C C4haloalkyl, CrC4alkoxy, -CN, -NO2, C C4alkylthio, d-C4alkylsulfinyl or by CrC alkylsulfonyl; or R8 and Rg together are C2-C5alkylene; R10 is hydrogen, CrC4alkyl, C C4haloalkyl or C3-C6cycloalkyl;
Rn is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, C C4haloalkyl or C3-C6haloalkenyl; R12 is hydrogen, CrC4alkyl, C C4haloalkyl or C3-C6cycloalkyl; R13 is hydrogen, CrC8alkyl, C3-C8alkenyl or C3-C8alkynyl; or
R13 is phenyl or phenyl-C C6alkyl, it being possible for the phenyl ring in turn to be mono- to penta-substituted by halogen or by Cι-C alkyl or mono-, di- or tri-substituted by C C halo- alkyl, CrC4alkoxy, -CN, -NO2, CrC8alkylthio, CrC8alkylsulfinyl or by CrC8alkylsulfonyl, or R13 is Cι-C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, CrC6aIkylamino, di(CrC6alkyl)amino or by CrC4alkoxy;
Rι4 is hydrogen, CrC8alkyl, C3-C8alkenyl or C3-C8alkynyl, or is CrC8alkyl mono- to penta- substituted by halogen or mono-, di- or tri-substituted by -CN or by CrC alkoxy; R15, R16 and R17 are each independently of the others CrC8alkyl, C3-C8alkenyl or C3-C8alkynyl, or C C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by Cι-C4alkoxy; Rιs is hydrogen or d-Caalkyl;
R19 is hydrogen, C C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C1-C4a!kyl or mono-, di- or tri-substituted by CrC4haloalkyl, CrC4alkoxy, -CN, -NO2, C C4alkylthio, CrC4alkylsulfinyl or by CrC4alkylsulfonyl; or
R18 and Rιg together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R20 is hydrogen, Cι-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by Cι-C4alkyl or mono-, di- or tri-substituted by CrC4haloalkyl, C C4alkoxy, -CN, -NO2, C C4alkylthio, CrC4alkylsulfinyl or by CrC4alkylsulfonyl; R2ι is hydrogen or CrC8alkyl; R22 is hydrogen or CrC8alkyl, or is C C8alkyl mono-, di- or tri-substituted by -COOH, C C8alkoxycarbonyI or by -CN, or
R22 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by CrC4alkyl or mono-, di- or tri- substituted by CrOjhaloalkyl, C C4alkoxy, -CN, -NO2, CrC4alkylthio, CrC4alkylsulfinyl or by CrC4aIkylsulfonyI; or R21 and R22 together are C2-C5alkylene; R23 is hydrogen, C C4alkyl, C C4haloalkyl or C3-C6cycloalkyl; R2 is hydrogen, C C4alkyl, C C4haloalkyl or C3-C6cycloalkyl;
R25 is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, Cι-C haloalkyl or C3-C6haloalkenyl; R26 is hydrogen or CrC8alkyl;
R27 is hydrogen or CrC8alkyl, or is CrC8alkyl mono-, di- or tri-substituted by -COOH, C C8- alkoxycarbonyl or by -CN, or
R27 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by CrC4alkyl or mono-, di- or tri- substituted by C C4haloalkyl, C C4alkoxy, -CN, -NO2, C C4alkylthio, C C4alkylsulfinyl or by Cι-C4alkylsulfonyl; or R26 and R27 together are C2-C5alkylene; R28 is hydrogen or d-C8alkyl;
R29 and R30 are each independently of the other hydrogen, CrCsalkyl, C3-C8alkenyl or C3-C8alkynyl, or Cι-C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by d-C4alkoxy;
R31 and R32 are each independently of the other CrC8alkyl, C3-C8alkenyl or C3-C8alkynyl, or CrC8alkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN or by Cι-C alkoxy; m is O, 1, 2, 3 or 4; each R2 independently is halogen, -CN, -SCN, -OCN, -N3, -SF5, -NO2) -NR33R34, -CO2R35, -CONR36R37, -C(R38)=NOR39, -COR40> -OR41, -SR42, -SOR43, -SOgR-u, -OSO2R45, -N([CO]pR46)COR47, -N(OR54)COR55, -N(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR6o)R6ι- -CR62(OR63)OR64, -OC(O)NR65R66, -SC(O)NR67R68, -OC(S)NR6gR70 or -N-phthalimide; or R2 is a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for that heterocyclic ring system in turn to be mono- to penta- substituted by halogen or by C C4alkyl or mono-, di- or tri-substituted by CrC4haloalkyl, hydroxy-CrC4alkyI, CrC alkoxy, CrC4alkoxy-CrC4alkyl. -CN, -NO2, CrCeatkylthio, Cι-C6alkylsulfinyl or by C C6alkylsulfonyl; R3 is hydrogen or Cι-C8alkyl; and
R 4 is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by CrC4alkyl or mono-, di- or tri-substituted by CrC4haloalkyl, d-C4alkoxy, -CN, -N02, d-C4alkylthio, CrC alkylsulfinyl or by CrC4alkylsulfonyl; or
R33 and R34 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R35 is hydrogen, CrC8alkyl, C3-C8alkenyl or C3-C8alkynyl, or is C C8alkyl, C3-C8alkenyl or C3-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by Cι-C alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta- substituted by halogen or by CrC4alkyl or mono-, di- or tri-substituted by C C haloalkyl, C C4alkoxy, -CN, -NO2, CrC4alkylthio, C C4alkylsulfinyl or by d-C4alkylsulfonyl; R36 is hydrogen or d-C8alkyl;
R37 is hydrogen or CrC8alkyl, or is CrC8alkyl mono-, di- or tri-substituted by -COOH, C C8- alkoxycarbonyl or by -CN, or
R37 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by CrC alkyl or mono-, di- or tri- substituted by C C4haloalkyl, C C4alkoxy, -CN, -NO2, CrC4alkylthio, Cι-C4alkylsulfinyl or by Cι-C4alkylsulfonyl; or R36 and R37 together are C3-C5alkylene; R38 is hydrogen, CrC4alkyl, Cι-C4haloalkyl or C3-C6cycloalkyl;
R39 is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, C C4haloalkyl or C3-C6haloalkenyI; R40 is hydrogen, C1-C4alkyl, d-C4haloalkyl, C C8alkylthio, -C(O)-C(O)Od-C4alkyl or C3-C6- cycloalkyl;
R4ι is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, d-Cealkoxy-d-Cealkyl, C C8alkyl- carbonyl, d-C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, d-Cealkoxy-Ci-Cealkoxycarbonyl, d-Cealkylthio-CrCealkyl, CrC6alkylsulfinyl-Cι-C6alkyl or d-Cealkylsulfonyl-d-Cealkyl; or R is phenyl or phenyl-d-C6alkyl, it being possible for the phenyl ring in turn to be mono- to penta-substituted by halogen or by d-C4alkyl or mono-, di- or tri-substituted by d-C4halo- alkyl, d-C4alkoxy, -CN, -NO2 or by -S(O)2d-C8alkyl, or
R ι is Cι-C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -COOH, CrC8alkoxycarbonyl, d-C6alkylamino, di(d-C6alkyl)amino or by -CN; R42 is hydrogen, CrC8alkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-C8alkyl mono- to penta- substituted by halogen or mono-, di- or tri-substituted by -CN or by d-C alkoxy; R^ and R 4 are each independently of the other d-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or C C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN or by d-dalkoxy;
R 5 is C C8alkyl, C C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by d-C alkoxy, or is C3-C8alkenyl or C3-C8alkynyl, or R45 is phenyl, it being possible for the phenyl ring to be mono- to penta-substituted by halogen or by C C4alkyl or mono-, di- or tri-substituted by CrC4haloalkyl, d-C4alkoxy, -CN, NO2, d-C8alkylthio, d-C8alkylsulfinyl or by Cι-C8alkylsulfonyl; R46 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl or d-C haloalkyl; R47 is hydrogen, d-C8alkyl. CrC4alkoxy, C3-C8alkenyl or C3-C8alkynyl, or is CrC8alkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, d-C4alkoxy, d-C8alkoxycarbonyl, -NH2, CrC4alkylamino, di(d-C4alkyl)amino, -NR48COR49) -NR50SO2R51
Figure imgf000008_0001
R 7 is phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta- substituted by halogen or by C C4alkyl or mono-, di- or tri-substituted by C C4haloalkyl, d-C4alkoxy, -CN, -NO2, d-C4aikylthio, d-C alkylsulfinyl or by Cι-C4alkylsulfonyl; p is 0 or 1 ;
R 8, R49, R50, R51, R52 and R53 are each independently of the others hydrogen, d-C8alkyl, phenyl, benzyl or naphthyl, it being possible for the three last-mentioned aromatic radicals in turn to be mono- to penta-substituted by halogen or by d-C8alkyl or mono-, di- or tri- substituted by d-C4haloalkyl, d-C4alkoxy, C C4alkylamino, di(Cι-C4alkyl)amino, -NH2, -CN, -NO2, d-C4alkylthio, C C4alkylsulfinyl or by Cι-C alkylsulfonyl;
R5 and R55 are each independently of the other hydrogen, d-C8alkyl, or phenyl which may in turn be mono- to penta-substituted by halogen or by Cι-C alkyl or mono-, di- or tri- substituted by C C haloalkyl, d-C alkoxy, -CN, -NO2, d-Cβalkylthio, d-C8alkylsuifinyl or by d-C8alkylsulfonyl;
R56 is hydrogen, d-C8alkyl, CrC4haloalkyl, d-C4alkoxy, C3-C8alkenyl, C3-C8alkynyl or benzyl, it being possible for benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-C4haloalkyl, C C4aIkoxy, -CN, -NO2, d-Csalkylthio, C C8alkylsulfinyl or by C C8alkylsulfonyl;
R5 is CrC8alkyl, d-C haloalkyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono- to penta-substituted by halogen or by CrC4alkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, d-C4alkylamino, di(d-C4alkyl)amino, -NH2, -CN, -NO2, d-dalkylthio, d-C4alkylsulfinyl or by Cι-C4alkylsulfonyl; R58 and R5g are each independently of the other d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono- to penta-substituted by halogen or by d-C4alkyl or mono-, di- or tri-substituted by d-dhalo- alkyl, d-C4alkoxy, d-C4alkylamino, di(Cι-C4alkyl)amino, -NH2, -CN, -NO2, d-C4alkylthio,
CrC4alkylsulfinyl or by C1-C4alkylsulfonyl;
R60 and R6ι are each independently of the other hydrogen or d-C6alkyl;
Re2, Rβ3 and R64 are each independently of the others hydrogen or d-C8alkyl, or
R63 and R64 together form a C2-C5alkylene bridge;
Res, Ree, Re7, Res, es and R70 are each independently of the others hydrogen or d-C8alkyl, or
R65 and R66, or R6 and R68, or R6g and R70 in each case together form a C2-C5alkylene bridge; or each R2 independently is C C8alkyl, or is C C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -N3, -SCN, -NO2, -NR7ιR72, -CO2R73, -CONR74R75,
-COR76, -C(R77)=NOR78, -C(S)NR79R80, -C(d-C4aIkylthio)=NR81, -OR82, -SR83, -SOR84,
-SO2R85, -O(SO2)R86, -N(R87)CO2R88, -N(R89)COR9o, -S+(R9ι)2, -N+(R92)3, -Si(Rg3)3 or by
C3-C6cycloalkyl; or each R2 independently is C C8alkyl substituted by a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from oxygen, nitrogen and sulfur, it being possible for that heterocyclic ring system in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, hydroxy-C1-C4alkyl, Cι-C4alkoxy,
C C4alkoxy-d-C alkyl, -CN, -NO2, Cι-C6alkylthio, CrC6alkylsulfinyl or by CrC6alkylsulfonyl; or each R2 independently is C2-C8alkenyl, or is C2-C8alkenyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -NO2, -CO2R94, -CONR95R96, -COR97,
-C(R98)=NOR99, -C(S)NR100Rιoι, -C(d-C4alkylthio)=NRι02, -ORι03, -Si(Rι04)3 or by C3-C6- cycloalkyl; or each R2 independently is C2-C8alkynyl, or is C2-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -CO Rιo5, -CONR106Rιo7> -CORios,
Figure imgf000009_0001
-C(C1-C4alkylthio)=NR113, -ORι14, -Si(R115)3 or by
C3-C6cycloalkyl; or each R2 independently is C3-C6cycloalkyl, or is C3-C6cycloalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -CO2Rn6> -CONRn7R118, -COR119,
-C(R1 o)=NOR12ι, -C(S)NR122R123 or by -C(d-C4alkylthio)=NR124; or two adjacent R2 substituents together form a d-C7alkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono- to penta-substituted by halogen or by d-C6alkyl or mono-, di- or tri-substituted by d-C6alkoxy, the total number of ring atoms being at least 5 and at most 9; or two adjacent R2 substituents together form a C2-C alkenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono- to penta-substituted by halogen or by C C6alkyl or mono-, di- or tri-substituted by d-C6alkoxy, the total number of ring atoms being at least 5 and at most 9; R71 is hydrogen or d-C8alkyl;
R72 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-C alkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-C alkylthio, d-dalkylsulfinyl or by d-C alkylsulfonyl; or
R71 and R72 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R73 is hydrogen, d-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-C8alkyl, C3-C8alkenyl or C3-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta- substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-C haloalkyl, d-dalkoxy, -CN, -NO2, d-C4alkylthio, C C4alkylsulfinyl or by d-dalkylsulfonyl; R74 is hydrogen or CrC8alkyl;
R75 is hydrogen, Cι-C8alkyl or C3-C7cycloalkyl, or is Cι-C8alkyl mono-, di- or tri-substituted by -COOH, C C8alkoxycarbonyl, Cι-C6alkoxy or by -CN; or
R75 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by Cι-C4alkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by Crdalkylsulfonyl; or
R74 and R75 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R76 is hydrogen, Cι-C alkyl, C C4haloalkyl or C3-C6cycloalkyl; Rrr is hydrogen, d-C4alkyl, d-C4haloalkyl or C3-C6cycloalkyl;
R78 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; and
R79 is hydrogen or d-C8alkyl;
Rso is hydrogen or C C8alkyl, or is C C8alkyl mono-, di- or tri-substituted by -COOH, C C8- alkoxycarbonyl or by -CN; or
R80 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C C alkyl or mono-, di- or tri- substituted by C1-C4haloalkyl, d-C4alkoxy, -CN, -NO2, Crdalkylthio, C C4alkylsulfinyl or by Cι-C alkylsulfonyl; or R79 and R80 together are C2-C alkylene; R8ι is hydrogen or CrC8alkyl;
R82 is -Si(CrC6alkyl)3, C3-C8alkenyl or C3-C8alkynyl, or is C C8alkyl which is mono- to penta- substituted by halogen or mono-, di- or tri-substituted by -CN, -NH2, d-C6alkylamino, di(Cι-C6alkyl)amino or by d-dalkoxy;
R83 is hydrogen, d-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or is C C8alkyl which is mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -NH2, d-C6alkylamino, di(Cι-C6alkyl)amino or by d-dalkoxy;
R84, R85 and R86 are each independently of the others C C8alkyl, C3-C8alkenyl or C3-C8- alkynyl, or d-C8alkyl which is mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by d-dalkoxy;
R8 and R89 are each independently of the other hydrogen, C C8alkyl or d-C8alkoxy; R88 is d-C8aIkyl; R90 is hydrogen or d-C8alkyl; R9ι is d-dalkyl;
R92 and R93 are each independently of the other d-C6alkyl;
R94 is hydrogen or is d-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta-substituted by halogen or by d-C4- alkyl or mono-, di- or tri-substituted by d-C4haloalkyl, d-C4alkoxy, -CN, -NO2, d-dalkylthio, C1-C4alkylsulfinyl or by d-dalkylsulfonyl; R95 is hydrogen or Cι-C8alkyl;
R96 is hydrogen or d-C8alkyl, or is C C8alkyl mono-, di- or tri-substituted by -COOH, Cι-C8aIkoxycarbonyl or by -CN; or
R96 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by C C4haloalkyl, CrC4alkoxy, -CN, -NO2, CrC4alkylthio, C C4alkylsulfinyl or by d-dalkylsulfonyl; or R95 and R96 together are C2-C5alkylene;
R97 and R98 are each independently of the other hydrogen, d-C4alkyl, d-C4haloalkyl or C3-C6cycloalkyl;
R99 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; R100 is hydrogen or d-C8alkyI; R101 is hydrogen or CrC8alkyl, or is d-C8alkyl mono-, di- or tri-substituted by -COOH, d-C8- alkoxycarbonyl or by -CN; or
R101 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-C4ha!oalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfiny! or by d-dalkylsulfonyl; or R100 and R101 together are C2-C5alkylene; Rio2 is hydrogen or d-C8alkyl;
R103 is hydrogen, d-C8alkyl, -Si(d-C6alkyl)3, C3-C8alkenyl or C3-C8alkynyl; Rιo4 is d-dalkyl;
R105 is hydrogen or is Cι-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono- to penta-substituted by halogen or mono-, di- or tri-substituted by C C4alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, C C4alkylsulfinyl or by d-dalkylsulfonyl; 106 is hydrogen or d-C8alkyl;
Rι07 is hydrogen or d-C8alkyl, or is d-C8alkyl mono-, di- or tri-substituted by -COOH, Cι-C8alkoxycarbonyl or by -CN, or
R107 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-C4alkoxy, -CN, -NO2, d-dalkylthio, d-C4alkylsulfinyl or by d-dalkylsulfonyl; or R106 and R107 together are C2-C5alkylene; R108 is hydrogen, Cι-C4alkyl, d-dhaloalkyl or C3-C6cycloalkyl; R109 is hydrogen, d-dalkyl, d-C4haloalkyl or C3-C6cycloalkyl;
R110 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, CrC4haloalkyl or C3-C6haloalkenyl; Rm is hydrogen or d-C8alkyl;
Rι12 is hydrogen or Cι-C8alkyl, or is CrC8alkyl mono-, di- or tri-substituted by -COOH, d-C8alkoxycarbonyl or by -CN; or
Rii2 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C C4alkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, C C4alkylthio, d-C4alkylsulfinyl or by d-dalkylsulfonyl; or Rm and Rn2 together are C2-C5alkylene; R is hydrogen or d-C8alkyl; R114 is hydrogen, d-C8alkyl, -Si(C C6alkyl)3, C3-C8alkenyl or C3-C8alkynyl; R115 is d-C6alkyl;
R116 is hydrogen or is d-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-C4alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-C4haloalkyl, C1-C4alkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-C4alkylsulfonyl; R117 is hydrogen or C C8alkyl;
Rι18 is hydrogen or d-C8alkyl, or is d-C8alkyl mono-, di- or tri-substituted by -COOH, d-C8alkoxycarbonyl or by -CN; or
Rns is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-C4alkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R117 and Rι18 together are C2-C5alkylene; R119 is hydrogen, d-C4alkyl, C C4haloalkyl or C3-C6cycloalkyl; Rι20 is hydrogen, d-C4alkyl, C C haIoalkyl or C3-C6cycloalkyl;
Rι21 is hydrogen, C C8alkyl, C3-C8alkenyl, C3-C8alkynyl, d-C4haloalkyl or C3-C6haloalkenyl; R122 is hydrogen or Cι-C8alkyl;
R123 is hydrogen or Cι-C8alkyl, or is d-C8alkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbony! or by -CN; or
Ri23 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-C4alkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, Cι-C alkylthio, d-dalkylsulfinyl or by Cι-C4alkyIsulfonyl; or R122 and Rι23 together are C2-C5alkylene; and R124 is hydrogen or Cι-C8alkyl, and to the agrochemically acceptable salts and all stereoisomers and tautomers of the compounds of formula I.
When n is 0, all free valencies on the heterocyclic groups Q, to Q6 of the compounds of formula I are occupied by hydrogen. When m is 0, all free valencies on the phenyl or pyridyl ring of the compounds of formula I are occupied by hydrogen.
Examples of substituents that are formed as a result of R5 and R6 together or R18 and Rιg together or R36 and R37 together or R74 and R75 together being a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom are piperidine, morpholine, thiomorpholine and pyrrolidine.
Examples of heterocyclic ring systems which may be aromatic or partially or fully saturated in the definition of R2 are:
Figure imgf000014_0001
The alkyl groups appearing in the substituent definitions may be straight-chained or branched and are, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl and the pentyl, hexyl, heptyl and octyl isomers.
Halogen is fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine.
Haloalkyl is, for example, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1 ,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl or 2,2,2- trichloroethyl; preferably trichloromethyl, difluorochloromethyl, difluoromethyl, trifluoromethyl or dichlorofluoromethyl.
Alkoxy groups have a chain length of preferably from 1 to 6, especially from 1 to 4, carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy or tert-butoxy, or the pentyloxy and hexyloxy isomers; preferably methoxy or ethoxy.
Alkoxy, alkenyl, alkynyl, alkoxyalkyl, alkylthio, alkylsulfonyl, alkylsulfinyl, alkylaminoalkoxy, alkoxycarbonyl, alkylcarbonyloxy, alkenylthio, alkenylsulfonyl, alkenylsulfinyl, alkynylsulfonyl, alkynylthio and alkynylsulfinyl groups are derived from the mentioned alkyl groups. The alkenyl and alkynyl groups may be mono- or poly-unsaturated. Alkenyl is, for example, vinyl, allyl, methallyl, 1 -methylvinyl or but-2-en-1-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, 2-methylbutyn-2-yl or but-3-yn-2-yl.
Alkylthio groups preferably have a chain length of from 1 to 4 carbon atoms. Alkylthio is, for example, methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, sec-butyl- thio or tert-butylthio, preferably methylthio or ethylthio. Alkylsulfinyl is, for example, methyl- sulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, 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.
Alkoxyalkyl groups preferably have from 1 to 6 carbon atoms. Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n-propoxymethyl, n-propoxyethyl, isopropoxymethyl or isopropoxyethyl.
Substituents where two adjacent R substituents (on the group Q^ Q2, Q3 or Q5) together form a d-C7alkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono- to penta-substituted by halogen or by Cι-C6alkyl or mono-, di- or tri-substituted by d-C6alkoxy, the total number of ring atoms being at least 5 and at most 9, or where two adjacent Ri substituents together form a C2-C7alkenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dalkoxy, the total number of ring atoms being at least 5 and at most 9, have, for example, the following structures:
Figure imgf000016_0001
Figure imgf000016_0002
Substituents where two adjacent R2 substituents together form a d-C7alkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by CrCealkoxy, the total number of ring atoms being at least 5 and at most 9, or where two adjacent R2 substituents together form a C2-C7alkenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono- to penta-substituted by halogen or by Crdalkyl or mono-, di- or tri-substituted by CrC6alkoxy, the total number of ring atoms being at least 5 and at most 9, have, for example, the following structures:
Figure imgf000017_0001
Figure imgf000017_0002
Figure imgf000017_0003
The invention relates also to the salts which the compounds of formula I are able to form preferably with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Suitable salt formers are described, for example, in WO 98/41089.
Among the alkali metal and alkaline earth metal hydroxides as salt formers, special mention should be made of the hydroxides of lithium, sodium, potassium, magnesium and calcium, especially the hydroxides of sodium and potassium.
Examples of amines suitable for ammonium salt formation include ammonia as well as primary, secondary and tertiary Cι-Cι8alkylamines, C C4hydroxyalkylamines and C2-C4alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropyl- amine, the four butylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methyl-ethylamine, methyl-isopropylamine, methyl-hexylamine, methyl- nonylamine, methyl-pentadecylamine, methyl-octadecylamine, ethyl-butylamine, ethyl- heptylamine, ethyl-octylamine, hexyl-heptylamine, hexyl-octylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, ethanolamine, n- propanolamine, isopropanolamine, N,N-diethanolamine, N-ethylpropanolamine, N- butylethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl- 2-amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-n-butylamine, triisobutylamine, 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, benzidines, naphthylamines and o-, m- and p-chloroanilines; but especially triethylamine, isopropylamine and diisopropylamine.
Preferred quaternary ammonium bases suitable for salt formation correspond, for example, to the formula [N(RaRbRcRd)]OH wherein Ra, Rb, c and Rd are each independently of the others d-dalkyl. Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.
Preference is given to compounds of formula I wherein each R1 independently is halogen, -CN, -SCN, -SF5, -NO2, -NR5R6, -CO2R7, -CONR8R9, -C(Rι0)=NOR11; -COR12, -OR13, -SR14, -SOR15, -SO2R16, -OSO2R17, d-C8alkyl, C2-C8alkenyl, C2-C8alkynyl or C3-C6cycloalkyl; or is d-C8alkyl, C2-C8alkenyl or C2-C8alkynyl mono-, di- or tri-substituted by halogen, -CN, -NO2, -NR18Ri9, -CO2R20, -CONR2ιR22) -COR23, -C(R24)=NOR25, -C(S)NR26R27, -C(C C4alkyl- thio)=NR28, -OR29, -SR30, -SOR31, -SO2R32 or by C3-C6cycloa!kyl; or each Ri independently is C3-C6cycloalkyl mono-, di- or tri-substituted by halogen, -CN, -NO2, -NRι8Rι9, -CO2R20, -CONR21R22, -COR23, -C(R24)=NOR25, -C(S)NR26R27, -C(CrC4alkyl- thio)=NR28) -SR30, -SOR31, -SO2R32 or by C3-C6cycloalkyl; or each Ri independently is phenyl which may in turn be mono-, di- or tri-substituted by halogen, C C4alkyl, C C4haIoalkyl, C C4alkoxy, -CN, -NO2, C C4alkylthio, Cr C4alkylsulfinyl or by d-dalkylsulfonyl; or, when Q is a group Q,, Q2, Q3 or Q5, two adjacent Ri substituents together may form a Crdalkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted by halogen, d-dalkyl or by d-dalkoxy, the total number of ring atoms being at least 5 and at most 9; or, when Q is a group Q^ Q2, Q3 or Q5, two adjacent Ri substituents together may form a C2-C7alkenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted by halogen, d-dalkyl or by d-dalkoxy, the total number of ring atoms being at least 5 and at most 9;
R3 or R4 are each independently of the other hydrogen, halogen, -CN, d-dalkyl or d-dalkoxy; or
R3 and R4 together are C2-C5alkylene; R5 is hydrogen or d-dalkyl;
R6 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-C alky(, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C4alkylsuIfonyl; or
R5 and R6 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R7 is hydrogen, d-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl, C3-C8a!kenyl or C3-C8alkynyl mono-, di- or tri-substituted by halogen, d-C4alkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R8 is hydrogen or C C8alkyl;
R9 is hydrogen or CrC8alkyl, or is d-C8alkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
Rg is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-C4alkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, CrC4alkylthio, d-dalkylsulfinyl or by d-C4alkylsulfonyl; or R8 and R9 together are C2-C5alkylene; Rio is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycIoalkyl;
R11 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; Ri2 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl; R13 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl; or
Ri3 is phenyl or phenyl-C C6alkyl, it being possible for the phenyl ring in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C8alkylsulfonyl; or
R13 is d-dalkyl mono-, di- or tri-substituted by halogen, -CN, Crdalkylamino, di(Crd- alkyl)amino or by d-C4alkoxy;
R14 is hydrogen, d-C8alkyl, C3~C8alkeny! or C3-C8alkynyl, or is d-C8alkyl mono-, di- or tri- substituted by halogen, -CN or by d-C4alkoxy;
R15, Rie and R17 are each independently of the others d-dalky!, C3-C8alkenyl or C3-C8- alkynyl, or d-C8alkyl mono-, di- or tri-substituted by halogen, -CN or by d-daikoxy; R18 is hydrogen or d-dalkyl;
R19 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d- dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, Crdalkylsulfinyl or by C dalkylsulfonyl; or
Rι8 and Rι9 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R20 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d- dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by Cr dalkylsuifonyl;
R21 is hydrogen or d-dalkyl;
R22 is hydrogen or d-dalkyl, or is d-C8alkyl mono-, di- or tri-substituted by -COOH,
Cι-C8alkoxycarbonyl or by -CN, or
Rz> is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, C C4haloalkyl, d-dalkoxy,
-CN, -NO2, d-C4alkylthio, Crdalkylsulfinyl or by d-dalkylsulfonyl; or
R21 and R22 together are C2-C5alkylene;
R23 is hydrogen, d-C4alkyl, CrC4haloalkyl or C3-C6cycloalkyl;
R24 is hydrogen, CrC4alkyl, d-C4haloalkyl or C3-C6cycioalkyl;
R25 is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, d-C4haloalkyl or C3-C6haloalkenyl;
R26 is hydrogen or d-C8alkyl;
R27 is hydrogen or d-C8alkyl, or is d-dalky! mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R27 is d-dalkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C4haloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
R26 and R27 together are C2-C5alkylene;
R28 is hydrogen or d-dalkyl;
R29 and R30 are each independently of the other hydrogen, d-dalkyl, C3-C8alkenyl or
C3-C8alkynyl, or C C8alkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy;
R31 and R32 are each independently of the other d-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or d-C8alkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy; m is O, 1 , 2, 3 or 4; each R2 independently is hydrogen, halogen, -CN, -SCN, -OCN, -N3, -SF5, -NO2, -NRssR^,
-CO2R35, -CONR36R37, -C(R38)=NOR39, -COR^, -OR41, -SR42, -SOR43, -SO2RΨ1, -OSO2R45, -N([CO]pR46)COR47) -N(OR54)COR55, -N(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR60)R6ι, -CR62(OR63)OR6 , -OC(O)NR65R66, -SC(O)NR67R68, -OC(S)NR69R70 or -N-phthalimide; or R2 is a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for that heterocyclic ring system in turn to be mono-, di- or tri- substituted by halogen, d-C4alkyl, d-dhaloalkyl, hydroxy-d-dalkyl, d-C alkoxy, d-C4alkoxy-d-C4alkyl, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R33 is hydrogen or d-dalkyl; and
Ru is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, Crdalkylsulfinyl or by d- dalkylsulfonyl; or
R33 and R34 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R35 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-C8alkyl, C3-C8alkenyl or C3-dalkynyl mono-, di- or tri-substituted by halogen, d-C4alkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-C4alkoxy, -CN, -NO2> d-dalkylthio, Crdalkylsulfinyl or by d-dalkylsulfonyl; R36 is hydrogen or d-dalkyl;
R37 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R37 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C haloalkyl, d-C alkoxy, -CN, -NO2, d-C4alky!thio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R36 and R37 together are C3-C5alkylene; R38 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl;
R39 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; R40 is hydrogen, d-daikyl, d-dhaloalkyl, C C8alkylthio, -C(O)-C(O)Od-C4alkyl or C3-C6cycloalkyl;
R4ι is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, CrC6alkoxy-CrC6alkyl, C C8alkyl- carbonyl, d-C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, CrC6alkoxy-CrC6alkoxycarbonyl, CrC6alkylthio-CrC6alkyl, Crdalkylsulfinyl-d-dalkyl or CrC6alkylsuifonyl-CrC6alkyl; or R41 is phenyl or phenyl-d-dalkyl, it being possible for the phenyl ring in turn to be mono-, di- or tri-substituted by halogen, C C4alkyl, CrC4haloalkyl, d-dalkoxy, -CN, -NO2 or by -S(O)2CrC8alkyl, or R41 is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl, d-dalkyl- amino, di(CrC6alkyl)amino or by -CN;
R 2 is hydrogen, CrC8alkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-C8alkyl mono-, di- or tri- substituted by halogen, -CN or by d-C4alkoxy;
R 3 and R are each independently of the other d-C8alkyl, C3-C8alkenyl or C3-C8alkynyl, or d-dalkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy; R45 is d-dalkyl, d-C8alkyl mono-, di- or tri-substituted by halogen, -CN or by d-C4alkoxy, or is d-C8alkenyl or C3-C8alkynyl, or
R 5 is phenyl, it being possible for the phenyl ring to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R46 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl or d-dhaloalkyl; R47 is hydrogen, d-dalkyl, d-dalkoxy, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl mono-, di- or tri-substituted by halogen, -CN, C C4alkoxy, d-C8alkoxycarbonyl, -NH2, C C4alkylamino, di(C C4alkyl)amino, -NR48COR49, -NR50SO2R5ι or by.-NR52CO2R53, or R47 is phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri- substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C4alkylsulfonyl; p is 0 or 1 ;
R48, R49, R5o, R51, R52 and R53 are each independently of the others hydrogen, d-dalkyl, phenyl, benzyl or naphthyl, it being possible for the three last-mentioned aromatic radicals in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dalkylamino, di(d-C4alkyl)amino, -NH2, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R54 and R55 are each independently of the other hydrogen, d-dalkyl, or phenyl which may in turn be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C4haloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R56 is hydrogen, d-dalkyl, d-C4haloalkyl, d-dalkoxy, C3-C8alkenyl, C3-C8aikynyl or benzyl, it being possible for benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R57 is d-dalkyl, d-dhaloalkyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono-, di- or tri-substituted by halogen, d-dalkyl, C dhaloalkyl, d-dalkoxy, d-C4aIkylamino, di(CrC4alky!)amino, -NH2, -CN, -NO2) d- dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R58 and R59 are each independently of the other d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dalkylamino, di(C C4alkyl)amino, -NH2, -CN, -NO2, d-dalkylthio, -dalkylsulfinyl or by d-dalkylsulfonyl;
Reo and R6ι are each independently of the other hydrogen or d-dalkyl; R62, R63 and R64 are each independently of the others hydrogen or d-dalkyl, or R63 and R64 together form a C2-C5alkylene bridge;
Res, Ree, Re7, Res, Res and R7o are each independently of the others hydrogen or d-dalkyl, or
Res and R66, or R67 and R68, or R69 and R70 in each case together form a C2-C5alkylene bridge; or each R2 independently is d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by halogen, -CN, -N3, -SCN, -NO2, -NR71R72, -CO2R73, -CONR74R75, -COR76, -C(R77)=NOR78, -C(S)NR79R80, -C(CrC4alkylthio)=NR81, -OR82, -SR83, -SOR84l -SO2R85, -O(SO2)R86, -N(R87)CO2R88, -N(R89)COR90, -S+(R91)2, -N+(R92)3, -Si(R93)3 or by C3-C6cycloalkyl; or each R2 independently is d-dalkyl substituted by a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for that heterocyclic ring system in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, hydroxy-d-dalkyl, d-dalkoxy, C C4alkoxy-CrC4alkyl, -CN, -NO2, d- dalkylthio, d-dalkylsulfinyl or by C C6alkylsulfonyl; or each R2 independently is C2-C8alkenyl, or is C2-C8alkenyl mono-, di- or tri-substituted by - CN, -NO2, -CO2R94, -CONR95R96, -COR97, -C(R98)=NOR99, -C(S)NRι∞Rιoι, -C(C C4alkyl- thio)=NR102, -OR103, -Si(R104)3 or by C3-C6cycloalkyl; or each R2 independently is C2-C8alkynyl, or is C2-C8alkynyl mono-, di- or tri-substituted by halogen, -CN, -CO2R105, -CONR10eRι07, -COR108, -C(R109)=NORno, -C(S)NRmR112, -C(C1-C4alkylthio)=NRn3, -OR , -Si(R115)3 or by C3-C6cycloalkyl; or each R2 independently is C3-C6cycloalkyl, or is C3-C6cycloalkyl mono-, di- or tri-substituted by halogen, -CN, -CO2Rn6, -CONR117R118, -CORtιβ, -C(Rι20)=NORι21, -C(S)NR122Ri23 or by -C(CrC4alkylthio)=NRι24; or two adjacent R2 substituents together form a d-dalkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted by halogen, d-dalkyl or by d-dalkoxy, the total number of ring atoms being at least 5 and at most 9; or two adjacent R2 substituents together form a C2-C7alkenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted by halogen, Crdalkyl or by d-dalkoxy, the total number of ring atoms being at least 5 and at most 9; R7ι is hydrogen or d-dalkyl;
R72 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, C C4alkylthio, Crdalkylsulfinyl or by C dalkylsulfonyl; or
R7ι and R72 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R73 is hydrogen, Crdalkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R74 is hydrogen or d-dalkyl;
R75 is hydrogen, -dalkyl or C3-C7cycloalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl, d-dalkoxy or by -CN; or
R75 is Cβ-dalkenyl, d-dalkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -N02, d-dalkylthio, d-C4alky.sulfl.1yl or by d-dalkylsulfonyl; or R7 and R75 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R7e is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl; R77 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl;
R78 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, d-C4haloalkyl or d-dhaloalkenyl; and
R79 is hydrogen or d-dalkyl;
R8o is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
Rβo is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-C4alkoxy, -CN, -N02, d-dalkylthio, d-dalkylsulfinyl or by C C4alkylsulfonyl; or R79 and R80 together are C2-C5alkylene; R8ι is hydrogen or d-dalkyl; R8 is -Si(Cι-C6alkyl)3, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl which is mono-, di- or tri- substituted by halogen, -CN, -NH2, Crdalkylamino, di(CrC6alkyl)amino or by d-C4alkoxy; R83 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is Crdalkyl which is mono-, di- or tri-substituted by halogen, -CN, -NH2, Crdalkylamino, di(Cι-C6alkyl)amino or by d-C4alkoxy;
R84, Res and R86 are each independently of the others d-dalkyl, C3-C8alkenyl or C3-C8- alkynyl, or d-C8alkyl which is mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy;
R87 and R89 are each independently of the other hydrogen, d-dalkyl or d-C8alkoxy; R88 is d-dalkyl; R90 is hydrogen or d-dalkyl; R91 is d-dalkyl;
R92 and Rg3 are each independently of the other d-dalkyl;
R94 is hydrogen or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, - CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R95 is hydrogen or d-dalkyl;
R96 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R96 is C -C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R95 and R96 together are C2-C5alkylene;
R97 and R98 are each independently of the other hydrogen, d-dalkyl, d-C4haloalkyl or d-C6cycloalkyl;
R99 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; Rioo is hydrogen or d-dalkyl;
R101 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-C8alkoxycarbonyl or by -CN; or
R101 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C4haloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; 0r R10o and R10ι together are C2-C5alkylene; R102 is hydrogen or d-dalkyl; R103 is hydrogen, d-dalkyl, -Si(CrdalkyI)3, C3-C8alkenyl or C3-C8alkynyl; R10 is d-dalkyl;
R105 is hydrogen or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-C alkoxy, -
CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R10e is hydrogen or d-dalkyl;
R107 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R107 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
R106 and R107 together are C2-C5alkylene;
R108 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl;
R109 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl;
Rι10 is hydrogen, C C8alkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl;
Rm is hydrogen or d-dalkyl;
R112 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R112 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, Crdalkyl, d-C4haloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-C4alkylsulfonyl; or
Rm and R together are C2-C5alkylene;
R113 is hydrogen or d-dalkyl;
R114 is hydrogen, d-dalkyl, -Si(d-C6alkyl)3, C3-C8alkenyl or C3-C8alkynyl;
R115 is d-dalkyl;
R116 is hydrogen or is Crdalkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono-, di- or tri-substituted by halogen, d-C4aikoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -
CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R117 is hydrogen or d-dalkyl;
R118 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R118 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, Crdalkyl, d-dhaloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
R117 and R118 together are C2-C5alkylene; R119 is hydrogen, C C4alkyl, CrC4haloalkyl or C3-C6cycloalkyl;
Rι2o is hydrogen, C1-C al yl, d-C4haloalkyl or C3-C6cycloalkyl;
R121 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, C C4haloalkyl or C3-C6haloalkenyl;
R122 is hydrogen or d-dalkyl;
R123 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R123 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
Rι22 and R123 together are C2-C alkylene; and
Rι24 is hydrogen or Crdalkyl.
Preference is given also to compounds of formula I wherein each Ri independently is halogen, -CN, -NO2, -C(Rι0)=NORn, -ORι3, -SO2R16, -OSO2R17, d-dalkyl or C2-C8alkenyl, or is d-dalkyl mono-, di- or tri-substituted by halogen or by -CN; Rι0 is hydrogen or C dalkyl; and Rn is Crdalkyl.
Preference is given likewise to compounds of formula I wherein Q is a group Q^ Q2, Q3 or Q5. Among those compounds special preference is given to those wherein Q is a group Q or Q2.
Preference is given furthermore to those compounds of formula I wherein each R2 independently is halogen, -CN, -SCN, -OCN, -N3, -CONR36R37, -C(R38)----:NOR39, -COR40, -OR41, -OSO2R45) -N([CO]pR46)COR47, -N(R56)SO2R5 , -N(SO2R58)SO2R59) -N=C(OR60)R6ι or CrC8alkyl, or is Crdalkyl mono-, di- or tri-substituted by halogen, -CN, -N3, -SCN, -CONR74R75, -COR76, -C(R77)=NOR78, -C(S)NR79R80, -OR82, -SOR84, -SO2R85 or by -N(R89)COR90.
The compounds of formula la
Figure imgf000027_0001
wherein R^ R2, R3, R4, Z, m and n are as defined for formula I, can be prepared analogously to known methods described, for example, in "Palladium in Heterocyclic Chemistry" from Tetrahedron Organic Chemistry Series 20, A Guide for the Synthetic Chemist, Editors Jie Jack Li and Gordon W. Gribble, Pergamon 2000, Tetrahedron Lett. 1986 (27), 1171 ; Tetrahedron Organic Chemistry 2000 (20), 359-362; ibid. 2000 (20), 390- 394; and K. Sonogashira in Comprehensive Organic Synthesis, Editors I. Fleming et ai, Oxford 1991 , Vol. 3, page 521 ff., for example by reacting a compound of formula lla
Figure imgf000028_0001
wherein Ri and n are as defined for formula I (Q = Q^ and X is halogen, with a compound of formula Ilia
Figure imgf000028_0002
wherein R3 and R are as defined for formula I and M+ is an alkali metal cation such as, for example, a lithium, sodium or potassium cation, to form a compound of formula IVa
Figure imgf000028_0003
wherein R1 s R3, R4 and n are as defined for formula I, and then coupling that compound with a compound of formula V
Figure imgf000028_0004
wherein Z, R2 and m are as defined for formula I and A is a leaving group such as, for example, halogen or trifluoromethanesulfonate, in the presence of a palladium catalyst.
Preparation of the compounds of formula I wherein Q is a group Q2, that is to say
compounds of formula lb (lb);
Figure imgf000028_0005
wherein Q is a group Q3, that is to say compounds of formula lc
(lc); wherein Q is a group Q , that is
Figure imgf000029_0001
to say compounds of formula Id (id);
Figure imgf000029_0002
wherein Q is a group Q5, that is to say compounds of formula le
(le); and wherein Q is a group Q6,
Figure imgf000029_0003
that is to say compounds of formula If
(If), is carried out in a manner
Figure imgf000029_0004
analogous to that described above by way of example for the compounds of formula la
(0 = 0,).
These preparation procedures for the compounds of formula I are illustrated in Reaction Schemes 1 , 2 and 3 specifically using the example of the compound of formula la (Q = Qi). It is generally true of all three Reaction Schemes that the various substituents R1 and R2 in the compounds of formulae lla and V either are already present at the outset or, however, they may be successively introduced only later in the reaction sequence, for example by means of nucleophilic or electrophilic aromatic substitution.
The same is also true of the analogous preparation of compounds of formulae lb, lc, Id, le and If (Q is a group Q2 to Q6), starting from the respective compounds of formulae lib, lie, lid, lie and llf:
Figure imgf000030_0001
In accordance with Reaction Scheme 1 , the compounds of formula la can be obtained, for example, by reaction of substituted propargyl ethers of formula IVa with compounds of formula V by means of Sonogashira coupling.
The propargyl ethers of formula IVa can, for their part, be obtained by a nucleophilic aromatic substitution reaction of compounds of formula lla wherein X is halogen with alcoholates of formula Ilia. Such substitution reactions are standard methods and may be carried out, for example, in analogy to Tetrahedron 1972 (28), 4155; Heterocycles 1990 (31 ), 1275 (for Q = Q1); J. Org. Chem. 1961 (26), 2764 (for Q = Q2); Tetrahedron Lett. 1996 (37), 4065; Heterocyclic Chem. 1995 (32), 1057 (for Q = Q3); J. Am. Chem. Soc. 1951 (73), 2986 (for Q = Q4); Collect Czech. Chem. 1975 (40), 2680 (for Q = Q5); and Tetrahedron Lett. 1985 (26), 4355 (for Q = Q6).
In the next step, the propargyl ethers of formula IVa are coupled with substituted phenyl or pyridine derivatives of formula V (Z is =N- or =C(R2)-) under typical Sonogashira conditions (K. Sonogashira in Comprehensive Organic Synthesis 1991 , Vol. 3, page 521 ff.; J. Org. Chem. 1998 (63), 8551 -8553). Suitable catalyst mixtures are, for example, tetrakis(triphenylphosphine)palladium or bis(triphenylphosphine)palladium(ll) dichloride together with copper(l) iodide (Cul); suitable bases are preferably amines, for example triethylamine, diethylamine or diisopropylethylamine.
The phenyl or pyridine derivatives of formula V preferably have a leaving group A, A being, for example, halogen or trifluoromethanesulfonate (Tetrahedron Organic Chemistry 2000 (20), 209-213; J. Org. Chem. 1998 (63), 8551-8553) and Tetrahedron Lett. 1986(27), 1171. Solvents used for the Sonogashira reaction are usually ethers, for example tetrahydrofuran, chlorinated hydrocarbons, for example chloroform, or dipolar aprotic solvents, for example dimethylformamide or dimethyl sulfoxide, and also amines, for example triethylamine or piperidine.
Reaction Scheme 1
nucleophilic substitution:
Figure imgf000031_0001
lla M+ = alkali metal ion, e.g. Na+ IVa
Sonogashira coupling:
Figure imgf000031_0002
V: A = halogen, -O-SO2-CF3; Pd catalyst, Cul, base
Figure imgf000031_0003
Pd-catalysed cross-coupling of appropriately substituted phenyl or pyridine derivatives of formula V with propargyl alcohols of formula III in accordance with K. Sonogashira, as shown in diagrammatic form in Reaction Scheme 2, results in compounds of formula VII. Such reactions are documented, for example, in Tetrahedron Organic Chemistry 2000 (20), 209-213 for pyridine derivatives and in J. Org. Chem. 1988 (53), 386; ibid. 1998 (63), 8551- 8553; and Tetrahedron Lett. 1986 (27), 1171 for phenyl derivatives. Subsequent reaction of the propargyl alcohols of formula VII with pyrazine derivatives of formula lla wherein X is halogen yields the compounds of formula la (Q = Qi).
The other compounds of formula I wherein Q is a group Q2, Q3, Q4l Q5 or Q6 can also be prepared in a manner analogous to that shown in Reaction Scheme 2. Reaction Scheme 2
Sonogashira:
Figure imgf000032_0001
lla: X = halogen base, e.g. NaH solvent, e.g. THF
Figure imgf000032_0002
V: A = halogen, O-SO2-CF3; VII Z = =C(R2)-, =N-
Figure imgf000032_0003
la
The compounds of formula I can also be obtained by further methods such as, for example, that shown in Reaction Scheme 3.
Reaction Scheme 3
Sonogashira:
sulfonylation or halogenation
Figure imgf000033_0001
V: A = halogen, O-SO2-CF3; VII
Figure imgf000033_0002
VIII: X1 = halogen, OTs, OMs la
Activation of the alcohol of formula VII according to Reaction Scheme 3 is carried out, for example, by sulfonylation or halogenation.
Sulfonylation of the alcohol of formula VII is a standard reaction and can be carried out, for example, using a sulfonic acid chloride, for example mesyl chloride or para-toluenesulfonic acid chloride (p-TosCI), in the presence of a tertiary amine, e.g. triethylamine, or an aromatic amine, e.g. pyridine, in a solvent such as, for example, a chlorinated hydrocarbon, e.g. carbon tetrachloride or methylene chloride, or an amine, e.g. pyridine. Such reactions are generally known and are described, for example, in J. Org. Chem. 1997 (62), 8987; J. Het. Chem. 1995 (32), 875-882; and Tetrahedron Lett. 1997 (38), 8671 -8674. Halogenation of the alcohol of formula VII can be carried out in analogy to standard methods. For example, bromination can be successfully carried out using carbon tetrabromide in the presence of triphenylphosphine (Synthesis 1998, 1015-1018) in methylene chloride. Chlorination can be successfully carried out using mineral acids, for example using concentrated hydrochloric acid (J. Org. Chem. 1955 (20), 95), or using para- toluenesulfonic acid chloride in the presence of an amine, for example triethylamine, in a solvent, for example methylene chloride (Tetrahedron Lett. 1984 (25), 2295). Preparation of the compound of formula la according to Reaction Scheme 3 can be carried out analogously to Synthesis 1995, 707-712 and Tetrahedron Lett. 1994 (35), 6405-6408, for example by means of copper iodide-catalysed etherification of the hydroxy-pyrazine of formula lla in the presence of the tosylate (Xi = OTs) or mesylate (X. = OMs) or halide (X^ = halogen) of formula VIII. Suitable solvents are dimethylformamide or acetonitrile; suitable bases are preferably potassium carbonate or 1 ,8-diazabicylo[5.4.0]undec-7-ene (DBU). The etherification can also be carried out in halogenated or aromatic hydrocarbons as solvent, for example in chloroform or in benzene, in the presence of silver carbonate as base. Such selective O-alkylation reactions in the presence of a ring nitrogen atom are described, for example, in Synth. Commun. 1994 (24), 1367 and Heterocycles 1990 (31), 819.
A further method by which the compounds of formula I can be prepared is performed with the aid of the Mitsunobu reaction in a manner analogous to that described, for example, in Synthesis 1981 (1); Tetrahedron Lett. 35, 2819-2822 (1994); and Chem. Letters 1994, 539 (with TMAD reagent as a replacement for the DEAD in the two aforesaid references). This synthesis route is illustrated in Reaction Scheme 4 using the example of the compounds of formula la (pyrazinyloxy-alkyne derivatives).
Figure imgf000034_0001
lla: X=OH la
The following applies to the individual reaction steps according to Reaction Schemes 1 to 4: The reactions resulting in the compounds of formula I are advantageously performed in aprotic, inert, organic solvents. Such solvents are hydrocarbons, such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons, such as dichloromethane, trichloro- methane, tetrachloromethane or chlorobenzene, ethers, such as diethyl ether, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetrahydrofuran or dioxane, nitriles, such as acetonitrile or propionitrile, amides, such as N,N-dimethylformamide, diethyl- formamide or N-methylpyrrolidinone. The reaction temperatures are preferably from -20°C to +120°C. The reactions are generally slightly exothermic and can usually be carried out at room temperature. For reducing the reaction time or also for initiation of the reaction, heating, up to the boiling point of the reaction mixture, may, where appropriate, be carried out for a short time. It is also possible for the reaction times to be reduced by adding a few drops of base as reaction catalyst. Suitable bases are especially tertiary amines, such as trimethylamine, triethylamine, quinuclidine, 1 ,4-diazabicyclo[2.2.2]octane, 1 ,5-diaza- bicyclo[4.3.0]non-5-ene or 1 ,5-diazabicyclo[5.4.0]undec-7-ene. However, there may also be used as bases inorganic bases, such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, carbonates, e.g. sodium carbonate or potassium carbonate, or hydrogen carbonates, e.g. potassium hydrogen carbonate or sodium hydrogen carbonate.
The compounds of formula I may, in conventional manner, be isolated by concentrating and/or evaporating off the solvent and purified by recrystallising or triturating the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
The starting compounds of formula lla used in Reaction Schemes 1 , 2 and 3, and the corresponding starting compounds of formulae lib, lie, lid, He and llf for preparation of the compounds of formulae lb, lc, Id, le and If are for the most part known or they can be prepared in analogy to known methods as described, for example, in J. Org. Chem. 1997 (62), 91 12; ibid. 1958 (23), 1522; J. Chem. Soc. 1948, 2191 ; Bull. Soc. Chim. Fr. 1957, 1009; J. Am. Chem. Soc. 74, 1580-1582 (1952); US-A-5 547 919; J. Chem. Soc. 1960, 4590; J. Org. Chem. 1963 (28), 1682; J. Heterocycl. Chem. 1994 (31 ), 1 177; and ibid 1982 (19), 1061.
The starting compounds of formulae III and Ilia are likewise known and in some cases are commercially available, or they can be prepared in analogy to known methods.
The compounds of formula V are likewise known and in some cases are commercially available. Examples of substituted compounds of formula V wherein Z is =N- are described, for example, in Tetrahedron Organic Chemistry 20, 209 (2000). The compounds of formulae IV (and IVa to IVf) and VII are novel. The present invention accordingly relates also to those compounds.
For the use according to the invention of the compounds of formula I, or of compositions comprising them, there come into consideration all methods of application customary in agriculture, for example pre-emergence application, post-emergence application and seed dressing, and also various methods and techniques such as, for example, the controlled release of active ingredient. For that purpose a solution of the active ingredient is applied to mineral granule carriers or polymerised granules (urea/formaldehyde) and dried. If required, 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 of time.
The compounds of formula I may be used as herbicides in their unmodified form, that is to say as obtained in the synthesis, but they are preferably formulated in customary manner together with the adjuvants conventionally employed in formulation technology, for example into emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules. Such formulations are described, for example, on pages 9 to 13 of WO 97/34485. 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, that is to say the compositions, preparations or mixtures comprising the compound (active ingredient) of formula I, or at least one compound of formula I, and, usually, one or more solid or liquid formulation adjuvants, are prepared in known manner, e.g. by homogeneously mixing and/or grinding the active ingredient(s) with the formulation adjuvants, for example solvents or solid carriers. Surface-active compounds (surfactants) may also be used in addition in the preparation of the formulations. Examples of solvents and solid carriers are given, for example, on page 6 of WO 97/34485.
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, on pages 7 and 8 of WO 97/34485. In addition, the surfactants conventionally employed in formulation technology, which are described, inter alia, in "McCutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981 , Stache, H., "Tensid- Taschenbuch", Carl Hanser Veriag, Munich/Vienna, 1981 , and M. and J. Ash, "Encyclopedia of Surfactants", Vol. I-III, Chemical Publishing Co., New York, 1980-81 , are also suitable for the preparation of the herbicidal compositions according to the invention.
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 ingredients, such as stabilisers, for example vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), anti-foams, for example silicone oil, preservatives, viscosity regulators, binders, tackifiers, and also fertilisers or other active ingredients.
The compounds of formula I are generally applied to the plant or the locus thereof at 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 experiment. It is dependent on the nature of the action, the stage of development of the cultivated plant and of the weed and on the application (place, time, method) and may vary within wide limits as a function of those parameters.
The compounds of formula I are distinguished by herbicidal and growth-inhibiting properties, allowing them to be used in crops of useful plants, especially cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and also for non-selective weed control. The term "crops" is to be understood as including also crops that have been made tolerant to herbicides or classes of herbicides as a result of conventional methods of breeding or genetic engineering techniques. The weeds to be controlied may be either monocotyledonous or dicotyledonous weeds, such as, for example, Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Panieum, Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Euphorbia, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
The following Examples further illustrate but do not limit the invention. Preparation Examples:
Example P1 : Preparation of 2-mercapto-5-methoxy-3H-pyrimidin-4-one (see J. Chem. Soc. 1960, 4590)
H
Figure imgf000038_0001
A mixture of 9.9 ml (0.1 mol) of methoxyacetic acid methyl ester and 8.1 ml (0.1 mol) of ethyl formate is added dropwise to a stirred suspension of 2.3 g (0.1 mol) of sodium in 30 ml of toluene, the temperature being kept below 30°C. On the following day, the toluene phase is decanted off and 15 ml of ethanol and 7.6 g (0.1 mol) of thiourea are added to the crude, viscous sodium salt of 3-hydroxy-2-methoxyacrylic acid methyl ester. The resulting mixture is stirred at 20°C for 1 hour and is then heated at reflux temperature for 5 hours. After cooling, the solid formed is dissolved in 50 ml of water and the resulting solution is rendered neutral with 6N hydrochloric acid. The desired title compound precipitates out and can, after drying at 100°C, be obtained in a yield of 8.3 g (52 % of theory). The product can be further used directly for further reactions.
For purification, the crude product is recrystallised from water, the desired title compound being obtained in the form of needles having a melting point of 280-281 °C (decomposition). 1H NMR (300 MHz, DMSO-d6): 12.526 ppm (broad singlet, 1 H); 12.136 ppm (broad singlet, 1 H); 7.016 ppm (s, 1 H); 3.630 ppm (s, 3H).
Figure imgf000038_0002
3.9 g of Raney nickel (slurry) are added to a hot solution of 4.1 g (0.026 mol) of 2-mercapto- 5-methoxy-3H-pyrimidin-4-one (Example P1) in 60 ml of water. After vigorous stirring for 8 hours at reflux temperature, the reaction mixture is filtered and the combined filtrates and washing fractions are concentrated by evaporation on a hot water bath. The residue obtained is recrystallised from ethanol in the presence of activated carbon. The desired target compound is obtained in a yield of 1.9 g (69 % of theory) in the form of needles having a melting point of 206-208°C. 1H NMR (300 MHz, DMSO-d6): 7.828 ppm (s, 1 H); 7.527 ppm (s, 1 H); 3.728 ppm (s, 3H). Example P3: Preparation of 4-chloro-5-methoxy-pyrimidine (see J. Chem. Soc. 1960. 4590 and US-A-5 547 919)
Figure imgf000039_0001
A suspension of 1.9 g (0.015 mol) of 5-methoxy-3H-pyrimidin-4-one (Example P2) in 4.2 ml (0.046 mol) of phosphorus oxychloride and 5.0 ml (0.031 mol) of N,N-diethylaniline is heated at 115°C for 3 hours. The dark, homogeneous mixture obtained is hydrolysed by adding crushed ice, the temperature being kept below 30°C. Extraction with diethyl ether, drying of the combined organic ethereal phases over sodium sulfate, and purification on a silica gel column (eluant: ethyl acetate/n-hexane 1/9) yields the desired target compound in a yield of 1.3 g (58 % of theory).
Further purification by means of sublimation at 80-85°C/15 Torr yields the desired title compound, having a melting point of 63-64°C.
1H NMR (300 MHz, CDCI3): 8.635 ppm (s, 1 H); 8.321 ppm (s, 1H); 4.025 ppm (s, 3H).
Example P4: Preparation of 5-methoxy-4-prop-2-vnyloxy-pyrimidine
Figure imgf000039_0002
0.59 ml (0.01 mol) of propargyl alcohol is added to a suspension of 0.265 g (0.011 mol) of sodium hydride in 8 ml of N,N-dimethylformamide whilst cooling with ice-water. The reaction mixture is stirred at 20°C for 30 minutes and then 1.44 g (0.01 mol) of 4-chloro-5- methoxy-pyrimidine (Example P3) at 0°C are added and stirring is carried out at 20°C for a further 3 hours. The reaction is stopped by adding ethyl acetate and water, and working- up is carried out. Purification of the resulting crude product on a silica gel column (eluant: ethyl acetate/isohexane 1/3) yields the desired target compound, having a melting point of 86-87°C, in a yield of 1.3 g (79 % of theory).
1H NMR (300 MHz, CDCI3): 8.436 ppm (s, 1 H); 8.101 ppm (s, 1 H); 5.090 ppm (d, 2H); 3.945 ppm (s, 3H); 2.510 ppm (dxd, 1H). Example P5: Preparation of {3-r3-(5-methoxy-pyrimidin-4-yloxy)-prop-1-ynyll-phenyl) acetonitrile
Figure imgf000040_0001
0.493 g (0.003 mol) of 5-methoxy-4-prop-2-ynyloxy-pyrimidine (Example P4) and 1.094 g (0.0045 mol) of 3-iodophenylacetonitrile are dissolved in separate amounts, each of 4 ml, of piperidine. Then, to the solution of 3-iodophenylacetonitrile, there are added first 0.175 g (0.00015 mol) of tetrakis(triphenylphosphine)palladium (Pd(PPh3) ) and also, after 5 minutes, the piperidine solution containing 5-methoxy-4-prop-2-ynyioxy-pyrimidine. 0.060 g (0.0003 mol) of copper(l) iodide (Cul) is added to the combined solution, whilst cooling with ice, and the reaction mixture is stirred at 20°C for 3 hours. Working-up of the reaction mixture is starting by adding 25 ml of saturated aqueous ammonium chloride solution and 25 ml of ethyl acetate. The aqueous phase is extracted twice with ethyl acetate, and the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. After filtering and concentrating by evaporation, 1.3 g of a yellow oil are obtained, which is purified by silica gel chromatography (eluant: ethyl acetate/isohexane 1/1). The desired target compound, having a melting point of 96- 97°C, is obtained in a yield of 0.75 g (89 % of theory).
1H NMR (300 MHz, CDCI3): 8.457 ppm (s, 1 H); 8.116 ppm (s, 1 H); 7.282-7.434 ppm (m, 4H); 5.318 ppm (s, 2H); 3.964 ppm (s, 3H); 3.724 ppm (s, 2H).
Example P6: Preparation of 2-methoxy-pyrazine 4-oxide (see J. Org. Chem. 1963 (28), 1682)
Figure imgf000040_0002
1.9 g (0.017 mol) of 30 % hydrogen peroxide are added to a solution of 1.1 g (0.01 mol) of 2-methoxy-pyrazine in 3 ml of glacial acetic acid and the resulting solution is heated at 65-68°C for 17 hours. The solution is concentrated to 1/3 of the original volume, diluted with the same amount of water and concentrated again. The residue is extracted with chloroform and the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. After concentration, two amounts, each of 25 ml, of toluene are added to the residue obtained and are concentrated again. The desired title compound, which can be used directly for further reactions, is obtained in a yield of 0.98 g (77 % of theory).
1H NMR (300 MHz, CDCI3): 7.988 ppm (d (J=4.2 Hz), 1H); 7.766-7.773 ppm (m, 1 H);
7.745 ppm (dxd (J=4.2 and 1.5 Hz), 1 H); 3.995 ppm (s, 3H).
Example P7: Preparation of 2-chloro-6-methoxy-pyrazine (see J. Heterocycl. Chem. 1994 (31 ). 1177)
Figure imgf000041_0003
Figure imgf000041_0001
A mixture of 0.98 g (0.0078 mol) of 2-methoxy-pyrazine 4-oxide (Example P6) in 4 ml of phosphoryl chloride is stirred for 2 hours whilst heating at reflux, with 1.25 ml (0.0078 mol) of N,N-diethylaniline being metered in with the aid of a syringe before the start of the reaction. The resulting solution is cooled to 20°C and poured onto ice-water. After adjusting the mixture to pH 9 with 30 % aqueous sodium hydroxide solution, extraction is carried out four times, using 10 ml of chloroform each time. The combined extracts are washed with 3N hydrochloric acid and saturated sodium chloride solution and are dried over sodium sulfate. A mixture of the desired target compound and of the isomeric 2-chloro-3-methoxy-pyrazine is obtained, which can be separated on a silica gel column (eluant: ethyl acetate/isohexane 1/8). The desired title compound is obtained in a yield of 0.29 g (25 % of theory), and the isomeric 2-chloro-3-methoxy-pyrazine in a yield of 0.38 g (33 % of theory). H NMR (300 MHz, CDCI3) of the title compound: 8.143 ppm (s, 1 H); 8.131 ppm (s, 1 H); 3.988 ppm (s, 3H).
1H NMR (300 MHz, CDCI3) of 2-chloro-3-methoxy-pyrazine: 8.031 ppm (d (J=2.7 Hz), 1 H); 7.937 ppm (d (J=2.7 Hz), 1 H); 4.057 ppm (s, 3H).
Example P8: Preparation of 2-chloro-6-methoxy-pyrazine 4-oxide
Figure imgf000041_0002
To a solution of 0.49 g (0.0034 mol) of 2-chloro-6-methoxy-pyrazine (Example P7) in 9 ml of dichloromethane there are added, under an argon gas atmosphere, first, within a period of 45 minutes and at 20°C, 0.19 g (0.002 mol) of hydrogen peroxide-urea adduct and then, dropwise, 0.3 ml (0.0021 mol) of trifluoroacetic anhydride in dichloromethane. Then there are again added, within a period of 45 minutes and at 20°C, 0.19 g (0.002 mol) of hydrogen peroxide-urea adduct and 0.3 ml (0.0021 mol) of trifluoroacetic anhydride in dichloromethane, and the reaction mixture is stirred further at 20°C for 30 minutes. The reaction is stopped by adding water, and the aqueous phase obtained is extracted with chloroform. The combined organic phases are washed with 5 % sodium hydrogen carbonate solution and saturated sodium chloride solution and dried over sodium sulfate. The desired title compound, having a melting point of 121-123°C, is obtained in a yield of 0.53 g (98 % of theory). The compound can be used directly for the next reaction step. 1H NMR (300 MHz, CDCI3): 7.802 ppm (d (J=1.2 Hz), 1 H); 7.691 ppm (d (J=1.2 Hz), 1 H); 4.012 ppm (s, 3H).
Example P9: Preparation of 2,5-dichloro-3-methoxy-pyrazine (see J. Heterocycl. Chem.
Figure imgf000042_0001
A mixture of 0.53 g (0.0033 mol) of 2-chloro-6-methoxy-pyrazine 4-oxide (Example P8) and 3 ml of phosphoryl chloride is boiled at reflux for 90 minutes. The excess of phosphoryl chloride is then removed under reduced pressure and the reaction mixture is poured onto ice-water and extracted with chloroform. The organic phase is washed with 5 % sodium hydrogen carbonate solution and dried over sodium sulfate. After removal of the solvent by distillation, the crude product is obtained, which is purified on a silica gel column (eluant: ethyl acetate/isohexane 1/9). The desired target compound is obtained in a yield of 0.55 g (92 % of theory). H NMR (300 MHz, CDCI3): 7.953 ppm (s, 1 H); 4.078 ppm (s, 3H).
Example P10: Preparation of 5-chloro-3-methoxy-2-prop-2-ynyloxy-pyrazine
Figure imgf000042_0002
0.23 ml (0.0038 mol) of propargyl alcohol is added to a suspension of 0.155 g (0.0038 mol) of sodium hydride (60 % suspension in oil) in 5 ml of N.N-dimethylformamide, whilst cooling with ice-water, and the resulting mixture is stirred at 20°C for 30 minutes. Then, 0.55 g (0.003 mol) of 2,5-dichloro-3-methoxy-pyrazine (Example P9) is added, whilst cooling in an ice-water bath, and the mixture is stirred further at 20°C for 3 hours. The reaction is stopped by adding ethyl acetate and water, and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. The crude product obtained is purified on a silica gel column (eluant: ethyl acetate/isohexane 1/9). The desired title compound, having a melting point of 71-72°C, is obtained in a yield of 0.23 g (53 % of theory), and 0.07 g (17 % of theory) of the isomeric 2-chloro-3-methoxy-5-prop-2-ynyloxy-pyrazine is obtained. 1H NMR (300 MHz, CDCI3) of the desired title compound: 7.650 ppm (s, 1 H); 5.007 ppm (d (J=2.4 Hz), 2H); 4.043 ppm (s, 3H); 2.496 ppm (dxd (J=2.4 Hz), 1 H). 1H NMR (300 MHz, CDCI3) of the isomeric 2-chloro-3-methoxy-5-prop-2-ynyloxy-pyrazine: 7.649 ppm (s, 1 H); 4.953 ppm (d (J=2.4 Hz), 2H); 4.057 ppm (s, 3H); 2.493 ppm (dxd (J=2.4 Hz), 1 H).
Example P11 : Preparation of {3-f3-(5-chloro-3-methoxy-pyrazin-2-yloxy)-prop-1 -ynvH-
Figure imgf000043_0001
To a solution of 0.33 g (0.0016 mol) of 5-chloro-3-methoxy-2-prop-2-ynyloxy-pyrazine (Example P10) and 0.60 g (0.0025 mol) of 3-iodophenylacetonitrile in 3 ml of N,N-dimethyl- formamide and 1.5 ml of diisopropylethylamine there is added a mixture of 0.03 g of bis(triphenylphosphine)palladium dichloride (PdCl2(PPh3)2), 0.03 g of triphenyiphosphine (PPh3) and 0.03 g of copper(l) iodide (Cul) at 20°C under an argon gas atmosphere. The reaction mixture is stirred at 20°C for 90 minutes. The reaction is stopped by adding ice, and the aqueous phase is extracted three times, using 10 ml of ethyl acetate each time. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product obtained is purified on a silica gel column (eluant: ethyl acetate/isohexane 1/3). 0.20 g (38 % of theory) of the desired title compound, having a melting point of 99-100°C, is obtained. 1H NMR (300 MHz, CDCI3): 7.671 ppm (s, 1 H); 7.278-7.425 ppm (m, 4H); 5.233 ppm (s, 2H); 4.060 ppm (s, 3H); 3.721 ppm (s, 2H). It is also possible for the preferred compounds listed in the following Tables to be obtained in a manner analogous to that described in Examples P1 to P11 or by the methods shown in Reaction Schemes 1 -4 and in the references indicated. In the column "Phys. data", the indicated temperatures denote the melting point (m.p.) of the compounds in question.
Table 1 : Compounds of formula Ia1 :
Figure imgf000044_0001
Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
1.001 3-OCH3, 5-CN 3-CI H H
1.002 3-F, 5-CI 3-CI H H
1.003 3-CI, 5-CI 3-CI H H
1.004 3-OCH3, 5-F 3-CI H H
1.005 3-OCH3, 5-CI 3-CI H H
1.006 3-OCH3, 5-Br 3-CI H H
1.007 3-CI, 5-CF3 3-CI H H
1.008 3-OCH3, 5-CF3 3-CI H H
1.009 3-OCH3, 5-CH3 3-CI H H
1.010 3-OCH3, 5-CH=NOCH3 3-CI H H
1.011 3-F, 5-CF3 3-CI H H
1.012 3-OCH3 3-CI H H
1.013 3-OCH3, 5-CN 3-CH2CN, 4-F H H
1.014 3-F, 5-CI 3-CH2CN, 4-F H H
1.015 3-CI, 5-CI 3-CH2CN, 4-F H H
1.016 3-OCH3, 5-F 3-CH2CN, 4-F H H
1.017 3-OCH3, 5-CI 3-CH2CN, 4-F H H
1.018 3-OCH3, 5-Br 3-CH2CN, 4-F H H
1.019 3-CI, 5-CF3 3-CH2CN, 4-F H H
1.020 3-OCH3, 5-CF3 3-CH2CN, 4-F H H
1.021 3-OCH3, 5-CH3 3-CH2CN, 4-F H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
1.022 3-OCH3, 5-CH=NOCH3 3-CH2CN, 4-F H H
1.023 3-F, 5-CF3 3-CH2CN, 4-F H H
1.024 3-OCH3 3-CH2CN, 4-F H H
1.025 3-OCH3, 5-CN 3-CH(CH3)CN H H
1.026 3-F, 5-CI 3-CH(CH3)CN H H
1.027 3-CI, 5-CI 3-CH(CH3)CN H H
1.028 3-OCH3, 5-F 3-CH(CH3)CN H H
1.029 3-OCH3, 5-CI 3-CH(CH3)CN H H
1.030 3-OCH3, 5-Br 3-CH(CH3)CN H H
1.031 3-CI, 5-CF3 3-CH(CH3)CN H H
1.032 3-OCH3, 5-CF3 3-CH(CH3)CN H H
1.033 3-OCH3, 5-CH3 3-CH(CH3)CN H H
1.034 3-OCH3, 5-CH=NOCH3 3-CH(CH3)CN H H
1.035 3-F, 5-CF3 3-CH(CH3)CN H H
1.036 3-OCH3 3-CH(CH3)CN H H
1.037 3-OCH3, 5-CN 3-CH2CN H H
1.038 3-F, 5-CI 3-CH2CN H H
1.039 3-CI, 5-CI 3-CH2CN H H
1.040 3-OCH3, 5-F 3-CH2CN H H
1.041 3-OCH3, 5-CI 3-CH2CN H H crystalline
1.042 3-OCH3, 5-Br 3-CH2CN H H
1.043 3-CI, 5-CF3 3-CH2CN H H
1.044 3-OCH3, 5-CF3 3-CH2CN H H
1.045 3-OCH3, 5-CH3 3-CH2CN H H
1.046 3-OCH3, 5-CH=NOCH3 3-CH2CN H H
1.047 3-F, 5-CF3 3-CH2CN H H
1.048 3-OCH3 3-CH2CN H H 104-105
1 .049 3-OCH3, 5-F 3-CH2CN CH3 H
1.050 3-OCH3, 5-CI 3-CH2CN CH3 H
1.051 3-OCH3, 5-CF3 3-CH2CN CH3 H
1.052 3-OCH3, 5-Br 3-CH2CN CH3 H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
1.053 3-CI, 5-CF3 3-CH2CN CH3 H
1.054 3-OCH3, 5-CN 3-CH2CN CH3 H
1.055 3-OCH3, 5-F 3-CHF2 H H -
1.056 3-OCHs, 5-CI 3-CHF2 H H
1.057 3-OCH3, 5-CF3 3-CHF2 H H
1.058 3-OCH3, 5-Br 3-CHF2 H H
1.059 3-CI, 5-CF3 3-CHF2 H H
1.060 3-OCH3, 5-CN 3-CHF2 H H
1.061 3-OCH3, 5-F 3-CH3 H H
1.062 3-OCH3, 5-CI 3-CH3 H H
1.063 3-OCH3, 5-CF3 3-CH3 H H
1.064 3-OCH3, 5-Br 3-CH3 H H
1.065 3-CI, 5-CF3 3-CH3 H H
1.066 3-OCH3, 5-CN 3-CH3 H H
1.067 3-OCH3, 5-F 3-CH2-CN F F
1.068 3-OCH3, 5-CI 3-CH2-CN F F
1 .069 3-OCH3, 5-CFs 3-CH2-CN F F
1.070 3-OCH3, 5-Br 3-CH2-CN F F
1.071 3-CI, 5-CF3 3-CHs-CN F F
1.072 3-OCH3, 5-CN 3-CH2-CN F F
1.073 5-OCHg, 6-F 3-CH2-CN H H
1.074 5-OCH3, 6-CI 3-CH2-CN H H crystalline
1.075 5-OCH3, 6-F 3-CH(CH3)CN H H
1.076 5-OCH3, 6-CI 3-CH(CH3)CN H H
1.077 5-OCH3, 6-CI 3-CHF2 H H
1.078 6-OCH3 3-CH2-CN H H 71-72
1.079 5,6-CH=CH-CH=CH- 3-CH2-CN H H amorphous
1.080 5,6-CH=CCI-CH=CH- 3-CH2-CN H H solid
1.081 5,6-CH-=CH-CH=CH-, 3-CH2-CN H H solid 3-OCH3
1.082 5,6-CH=CCI-CH=CH-, 3-CH2-CN H H crystalline Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
3-OCH3
1.083 5,6-CH=CCI-CH=CH-, 4-CI H H crystalline 3-OCH3
1.084 5-CI, 6-OCH3 3-CH2-CN H H crystalline
1.085 5,6-CH=CH-CCI=CH-, 3-CH2-CN H H crystalline 3-CI
1.086 5,6-CH=CCI-CH=CH-, 3-CHs-CN H H crystalline 3-CI
1.087 3-CI 3-CH2-CN H H crystalline
1.088 5,6-CH=CCI-CH=CH-, 3-CH2-CN H H 3-N-piperidyl
1.089 5,6-CH=CH-CH-=CH-, 4-CI H H 3-(2-thienyl)
1.090 5,6-CH=CH-CH=CH-, 4-CI H H 3-phenyl
1.091 3-OCHg, 5-CI 3-CH2CN H H
1.092 3-OCH3, 5-CI 3-CH(CH3)CN H H
1.093 3-OCH3> 5-CI 3-CI H H
1.094 3-OCH3, 5-CI 3-CH2-CN, 4-F H H
1.095 3-OCH3, 5-CI 3-CH(CH3)CN, 4-F H H
1.096 3-OCH3, 5-CI 3-CH2-CN, 6-F H H
1.097 3-OCH3, 5-CI 3-CH(CH3)CN, 6-F H H
1.098 3-OCH3, 5-CI 3-CH2-CN, 4-F, 6-F H H
1.099 3-OCH3, 5-CI 3-CH(CH3)CN, 4-F, 6-F H H
1.100 3-OCH3, 5-CI 3-CH2-CN, 4-CI, 6-F H H
1.101 3-OCH3, 5-CI 3-CH(CH3)CN, 4-CI, 6-F H H
1.102 3-OCHg, 5-CI 3-CI, 6-F H H
1.103 3-OCH3, 5-CI 3-CH2-CN, 4-CN H H
1.104 3-OCH3, 5-CI 3-CH2-CN, 4-CH3 H H
1.105 3-OCH3, 5-CI 3-CH(CH3)CN, 4-CH3 H H
1.106 3-OCH3, 5-CI 3-Br H H
Figure imgf000048_0001
Figure imgf000049_0001
Comp. Ri R2 Rs R4 Phys. data no. m.p. (°C)
1.169 3-OCH3 3-CHF2, 6-F H H
1.170 3-OCH3 3-CHF2, 4-F, 6-F H H
1.171 3-OCHg, 5-F 3-CH2CN, 4-F H H
1.172 3-OCH3, 5-F 3-CH(CH3)CN, 4-F H H
1.173 3-OCH3, 5-F 3-CH2CN, 6-F H H
1.174 3-OCH3, 5-F 3-CH(CH3)CN, 6-F H H
1.175 3-OCH3, 5-F 3-CH2CN, 4-F, 6-F H H
1.176 3-OCH3, 5-F 3-CH(CH3)CN, 4-F, 6-F H H
1.177 3-OCH3, 5-F 3-CH2CN, 4-CI, 6-F H H
1.178 3-OCH3, 5-F 3-CH(CH3)CN, 4-CI, 6-F H H
1.179 3-OCH3, 5-F 3-CH2CN, 4-CN H H
1.180 3-OCH3, 5-F 3-CH2CN, 4-CH3 H H
1.181 3-OCH3, 5-F 3-CH(CH3)CN, 4-CH3 H H
1.182 3-OCH3, 5-F 3-CH2CN, 4-NO2 H H
1.183 3-OCH3, 5-F 3-CH2CN, 4-NH2 H H
1.184 3-OCH3, 5-F 3-CHF2, 4-F H H
1.185 3-OCH3, 5-F 3-CHF2, 6-F H H
1.186 3-OCH3, 5-F 3-CHF2, 4-F, 6-F H H
Table 2: Compounds of formula Ia3:
Figure imgf000050_0001
Figure imgf000051_0001
Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
2.037 3-OCH3, 5-CN 5-CH(CH3)CN H H
2.038 3-F, 5-CI 5-CH(CH3)CN H H
2.039 3-CI, 5-CI 5-CH(CH3)CN H H
2.040 3-OCHs, 5-F 5-CH(CH3)CN H H
2.041 3-OCH3, 5-CI 5-CH(CH3)CN H H
2.042 3-OCH3, 5-Br 5-CH(CH3)CN H H
2.043 3-CI, 5-CF3 5-CH(CH3)CN H H
2.044 3-OCHs, 5-CF3 5-CH(CH3)CN H H
2.045 3-OCH3, 5-CH3 5-CH(CH3)CN H H
2.046 3-OCH3, 5-CH=NOCH3 5-CH(CH3)CN H H
2.047 3-F, 5-CF3 5-CH(CH3)CN H H
2.048 3-OCH3 5-CH(CH3)CN H H
2.049 3-OCH3, 5-F 5-CH2-CN F F
2.050 3-OCH3, 5-CI 5-CH2-CN F F
2.051 3-OCH3, 5-CFg 5-CH2-CN F F
2.052 3-OCH3, 5-Br 5-CH2-CN F F
2.053 3-CI, 5-CF3 5-CH2-CN F F
2.054 3-OCH3, 5-CN 5-CH2-CN F F
Figure imgf000052_0001
Comp. Ri Ra R3 R4 Phys. data no. m.p. (°C)
3.006 3-OCHs, 5-Br 4-CH3 H H
3.007 3-CI, 5-CF3 4-CH3 H H
3.008 3-OCH3, 5-CF3 4-CH3 H H
3.009 3-OCH3, 5-CH3 4-CH3 H H
3.010 3-OCHg, 5-CH=NOCH3 4-CH3 H H
3.011 3-F, 5-CF3 4-CH3 H H
3.012 3-OCH3 4-CH3 H H
3.013 3-OCH3, 5-CN 4-CH2-CN H H
3.014 3-F, 5-CI 4-CH2-CN H H
3.015 3-CI, 5-CI 4-CH2-CN H H
3.016 3-OCH3, 5-F 4-CH2-CN H H
3.017 3-OCH3, 5-CI 4-CH2-CN H H
3.018 3-OCH3, 5-Br 4-CH2-CN H H
3.019 3-CI, 5-CF3 4-CH2-CN H H
3.020 3-OCH3, 5-CF3 4-CH2-CN H H
3.021 3-OCH3, 5-CH3 4-CH2-CN H H
3.022 3-OCH3, 5-CH=NOCH3 4-CH2-CN H H
3.023 3-F, 5-CFg 4-CH2-CN H H
3.024 3-OCH3 4-CH2-CN H H
3.025 3-OCH3, 5-F 4-CH2-CN F F
3.026 3-OCHs, 5-CI 4-CH2-CN F F
3.027 3-OCH3, 5-CF3 4-CH2-CN F F
3.028 3-OCH3, 5-Br 4-CH2-CN F F
3.029 3-CI, 5-CFg 4-CH2-CN F F
3.030 3-OCH3, 5-CN 4-CH2-CN F F
3.031 3-OCHs, 5-F 4-CHF2 H H
3.032 3-OCH3, 5-CI 4-CHF2 H H
3.033 3-OCH3, 5-CF3 4-CHF2 H H
3.034 3-OCH3, 5-Br 4-CHF2 H H
3.035 3-CI, 5-CF3 4-CHF2 H H
3.036 3-OCH3, 5-CN 4-CHF2 H H able 4: Compounds of formula lbg1 :
Figure imgf000054_0001
Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
4.001 2-CN; 4-OCH3 3-CH2-CN, 4-F H H
4.002 2-CI, 4-F 3-CH2-CN, 4-F H H
4.003 2-CI, 4-CI 3-CH2-CN, 4-F H H
4.004 2-F, 4-OCH3 3-CH2-CN, 4-F H H
4.005 2-CI, 4-OCH3 3-CH2-CN, 4-F H H
4.006 2-Br, 4-OCHg 3-CH2-CN, 4-F H H
4.007 2-CF3, 4-CI 3-CH2-CN, 4-F H H
4.008 2-CF3, 4-OCH3 3-CH2-CN, 4-F H H
4.009 2-CH3, 4-OCH3 3-CH2-CN, 4-F H H
4.010 2-CH=NOCH3, 4-OCH3 3-CH2-CN, 4-F H H
4.01 1 2-CF3, 4-F 3-CH2-CN, 4-F H H
4.012 4-OCH3 3-CH2-CN, 4-F H H
4.013 2-CN; 4-OCH3 3-CH(CH3)CN H H
4.014 2-CI, 4-F 3-CH(CH3)CN H H
4.015 2-CI, 4-CI 3-CH(CH3)CN H H
4.016 2-F, 4-OCH3 3-CH(CH3)CN H H
4.017 2-CI, 4-OCH3 3-CH(CH3)CN H H
4.018 2-Br, 4-OCH3 3-CH(CH3)CN H H
4.019 2-CF3, 4-CI 3-CH(CH3)CN H H
4.020 2-CF3, 4-OCH3 3-CH(CH3)CN H H
4.021 2-CH3, 4-OCH3 3-CH(CH3)CN H H
4.022 2-CH=NOCH3, 4-OCH3 3-CH(CH3)CN H H
4.023 2-CF3, 4-F 3-CH(CH3)CN H H
4.024 4-OCH3 3-CH(CH3)CN H H
4.025 2-CN; 4-OCH3 3-CH2-CN H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
4.026 2-CI, 4-F 3-CH2-CN H H
4.027 2-CI, 4-CI 3-CH2-CN H H
4.028 2-F, 4-OCHg 3-CH2-CN H H
4.029 2-CI, 4-OCHg 3-CH2-CN H H crystalline
4.030 2-Br, 4-OCH3 3-CH2-CN H H
4.031 2-CF3, 4-CI 3-CH2-CN H H
4.032 2-CF3, 4-OCH3 3-CH2-CN H H resin
4.033 2-CH3, 4-OCH3 3-CH2-CN H H crystalline
4.034 2-CH=NOCH3, 4-OCH3 3-CH2-CN H H
4.035 2-CF3, 4-F 3-CH2-CN H H
4.036 4-OCH3 3-CH2-CN H H
4.037 2-F, 4-OCH3 3-CH2-CN F F
4.038 2-CI, 4-OCH3 3-CH2-CN F F
4.039 2-CF3, 4-OCH3 3-CH2-CN F F
4.040 2-Br, 4-OCH3 3-CH2-CN F F
4.041 2-CF3, 4-CI 3-CH2-CN F F
4.042 2-CN; 4-OCH3 3-CH2-CN F F
4.043 2-NH2, 4-OCH3 3-CH2-CN H H crystalline
4.044 2-SCH3 3-CH2-CN H H 97-98
4.045 2-CF3, 4-N(CH3)2 3-CH2-CN H H crystalline
4.046 2-CH3) 4-SCH3 3-CH2-CN H H
4.047 2-S(O)2CH3 4-CI H H
4.048 2-CN; 4-OCH3 3-CH2-CN, 6-F H H
4.049 2-CI, 4-F 3-CH2-CN, 6-F H H
4.050 2-CI, 4-CI 3-CH2-CN, 6-F ' H H
4.051 2-F, 4-OCH3 3-CH2-CN, 6-F H H
4.052 2-CI, 4-OCH3 3-CH2-CN, 6-F H H
4.053 2-Br, 4-OCH3 3-CH2-CN, 6-F H H
4.054 2-CF3, 4-CI 3-CH2-CN, 6-F H H
4.055 2-CF3, 4-OCH3 3-CH2-CN, 6-F H H
4.056 2-CH3, 4-OCH3 3-CH2-CN, 6-F H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
4.057 2-CH=NOCH3, 4-OCH3 3-CH2-CN, 6-F H H
4.058 2-CF3, 4-F 3-CH2-CN, 6-F H H
4.059 4-OCH3 3-CH2-CN, 6-F H H
4.060 2-CN; 4-OCH3 3-CH(CH3)CN, 4-F H H
4.061 2-CI, 4-F 3-CH(CH3)CN, 4-F H H
4.062 2-CI, 4-CI 3-CH(CH3)CN, 4-F H H
4.063 2-F, 4-OCH3 3-CH(CH3)CN, 4-F H H
4.064 2-CI, 4-OCHg 3-CH(CH3)CN, 4-F H H
4.065 2-Br, 4-OCHg 3-CH(CH3)CN, 4-F H H
4.066 2-CF3, 4-CI 3-CH(CH3)CN, 4-F H H
4.067 2-CF3, 4-OCH3 3-CH(CH3)CN, 4-F H H
4.068 2-CH3, 4-OCH3 3-CH(CH3)CN, 4-F H H
4.069 2-CH=NOCH3, 4-OCH3 3-CH(CH3)CN, 4-F H H
4.070 2-CF3, 4-F 3-CH(CH3)CN, 4-F H H
4.071 4-OCH3 3-CH(CH3)CN, 4-F H H
4.072 2-CN; 4-OCH3 3-CH2-CN, 4-CI, 6-F H H
4.073 2-CI, 4-F 3-CH2-CN, 4-CI, 6-F H H
4.074 2-CI, 4-CI 3-CH2-CN, 4-CI, 6-F H H
4.075 2-F, 4-OCH3 3-CH2-CN, 4-CI, 6-F H H
4.076 2-CI, 4-OCHg 3-CH2-CN, 4-CI, 6-F H H
4.077 2-Br, 4-OCH3 3-CH2-CN, 4-CI, 6-F H H
4.078 2-CF3, 4-CI 3-CH2-CN, 4-CI, 6-F H H
4.079 2-CF3, 4-OCHg 3-CH2-CN, 4-CI, 6-F H H
4.080 2-CH3, 4-OCH3 3-CH2-CN, 4-CI, 6-F H H
4.081 2-CH=NOCH3, 4-OCH3 3-CH2-CN, 4-CI, 6-F H H
4.082 2-CF3, 4-F 3-CH2-CN, 4-CI, 6-F H H
4.083 4-OCH3 3-CH2-CN, 4-CI, 6-F H H
4.084 2-NH2, 4-OCHg 3-CH(CH3)CN, 4-F H H
4.085 2-SCH3 3-CH(CH3)CN, 4-F H H
4.086 2-CF3, 4-N(CH3)2 3-CH(CH3)CN, 4-F H H
4.087 2-CH3, 4-SCH3 3-CH(CH3)CN, 4-F H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
4.088 2-S(O)2CH3 3-CH(CH3)CN, 4-F H H
4.089 2-NH2, 4-OCH3 3-CH2-CN, 6-F H H
4.090 2-SCH3 3-CH2-CN, 6-F H H
4.091 2-CF3, 4-N(CH3)2 3-CH2-CN, 6-F H H
4.092 2-CH3, 4-SCH3 3-CH2-CN, 6-F H H
4.093 2-S(O)2CH3 3-CH2-CN, 6-F H H
4.094 2-NH2, 4-OCHg 3-CH2-CN, 4-CI, 6-F H H
4.095 2-SCH3 3-CH2-CN, 4-CI, 6-F H H
4.096 2-CF3, 4-N(CH3)2 3-CH2-CN, 4-CI, 6-F H H
4.097 2-CH3, 4-SCH3 3-CH2-CN, 4-CI, 6-F H H
4.098 2-S(O)2CH3 3-CH2-CN, 4-CI, 6-F H H
4.099 4-OCH3 3-CHF2, 4-F H H
4.100 4-OCH3 3-CHF2, 6-F H H
4.101 4-OCH3 3-CHF2, 4-F, 6-F H H
4.102 4-OCH3 3-CHF2, 4-CI, 6-F H H
4.103 4-OCH3 3-CHF2 H H
4.104 2-CI, 4-OCH3 3-CHF2, 4-F H H
4.105 2-CI, 4-OCH3 3-CHF2, 6-F H H
4.106 2-CI, 4-OCH3 3-CHF2, 4-F, 6-F H H
4.107 2-CI, 4-OCH3 3-CHF2, 4-CI, 6-F H H
4.108 2-CI, 4-OCH3 3-CHF2 H H
4.109 2-CH3, 4-OCH3 3-CHF2, 4-F H H
4.110 2-CH3, 4-OCH3 3-CHF2, 6-F H H
4.111 2-CH3, 4-OCH3 3-CHF2, 4-F, 6-F H H
4.1 12 2-CH3, 4-OCH3 3-CHF2, 4-CI, 6-F H H
4.113 2-CH3, 4-OCH3 3-CHF2 H H
4.114 2-CF3, 4-OCH3 3-CHF2, 4-F H H
4.1 15 2-CF3, 4-OCH3 3-CHF2, 6-F H H
4.1 16 2-CF3, 4-OCH3 3-CHF2, 4-F, 6-F H H
4.1 17 2-CF3, 4-OCH3 3-CHF2, 4-CI, 6-F H H
4.118 2-CF3, 4-OCH3 3-CHF2 H H Comp. Ri R2 R3 H Phys. data no. m.p. (°C)
4.119 2-CH3, 4-OCH3 3-CHF2, 4-F H H
4.120 4-OCH3 3-CHF2, 4-F H H
4.121 4-OCH3 3-CHF2, 6-F H H
4.122 4-OCH3 3-CHF2, 4-F, 6-F H H
4.123 4-OCH3 3-CHF2, 4-CI, 6-F H H
4.124 4-OCH3 3-CHF2 H H
Table 5: Compounds of formula lb 1 :
Figure imgf000058_0001
Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
5.001 2-F, 5-OCH3 3-CH2-CN, 4-F H H
5.002 2-CI, 5-OCH3 3-CH2-CN, 4-F H H
5.003 5-OCH3 3-CH2-CN, 4-F H H
5.004 5-F 3-CH2-CN, 4-F H H
5.005 5-CI 3-CH2-CN, 4-F H H
5.006 2-CH3, 5-CI 3-CH2-CN, 4-F H H
5.007 2-F, 5-CI 3-CH2-CN, 4-F H H
5.008 5-CH3 3-CHs-CN, 4-F H H
5.009 2-F, 5-OCH3 3-CI H H
5.010 2-CI, 5-OCH3 3-CI H H
5.011 5-OCH3 3-CI H H
5.012 5-F 3-CI H H
5.013 5-CI 3-CI H H
5.014 2-CH3, 5-CI 3-CI H H
5.015 2-CI, 5-F 3-CI H H 99-100
5.016 5-CH3 3-CI H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
5.017 2-F, 5-OCH3 3-CH2-CN H H
5.018 2-CI, 5-OCH3 3-CH2-CN H H
5.019 5-OCH3 3-CH2-CN H H
5.020 5-F 3-CH2-CN H H
5.021 5-CI 3-CH2-CN H H
5.022 2-CH3, 5-CI 3-CH2-CN H H crystalline
5.023 2-CI, 5-F 3-CH2-CN H H
5.024 5-CH3 3-CH2-CN H H
5.025 5-OCH3 3-CH2-CN H H 96-97
5.026 2-CH3, 5-OCH3 3-CH2-CN H H 109-1 10
5.027 5-OCH3 3-CH2CN, 4-CI H H
5.028 5-OCH3 3-CH2CN, 4-CH3 H H
5.029 5-OCH3 3-CH2CN, 4-F, 6-F H H
5.030 5-OCH3 3-CH2CN, 4-CI, 6-F H H
5.031 5-OCH3 3-CH2CN, 4-CH3, H H 6-F
5.032 5-OCH3 3-CHF2 H H
5.033 5-OCH3 3-CHF2, 4-F H H
5.034 5-OCHg 3-CHF2, 4-CI H H
5.035 5-OCH3 3-CHF2, 4-CH3 H H
5.036 5-OCH3 3-CHF2, 4-F, 6-F H H
5.037 5-OCH3 3-CHF2, 4-CI, 6-F H H
5.038 5-OCH3 3-CHF2, 4-CH3, 6-F H H
5.039 5-OCHg 3-CH(CH)3CN H H
5.040 5-OCH3 3-CH(CH)3CN, 4-F H H
5.041 5-OCH3 3-CH(CH)3CN, 4-CI H H
5.042 5-OCH3 3-CH(CH)3CN, H H 4-CH3
5.043 5-OCH3 3-CH(CH)3CN, 4-F, H H 6-F
5.044 5-OCH3 3-CH(CH)3CN, 4-CI, H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
6-F
5.045 5-OCH3 3-CH(CH)3CN, H H 4-CH3, 6-F
5.046 5-OCH3, 2-CH3 3-CH2CN, 4-F H H
5.047 5-OCH3, 2-CH3 3-CH2CN, 4-CI H H
5.048 5-OCH3, 2-CH3 3-CH2CN, 4-CHg H H
5.049 5-OCH3, 2-CH3 3-CH2CN, 4-F, 6-F H H
5.050 5-OCHg, 2-CH3 3-CH2CN, 4-CI, 6-F H H
5.051 5-OCH3, 2-CH3 3-CH2CN, 4-CH3, H H 6-F
5.052 5-OCH3, 2-F 3-CH2CN, 4-F H H
5.053 5-OCH3, 2-F 3-CH2CN, 4-CI H H
5.054 5-OCH3, 2-F 3-CH2CN, 4-CH3 H H
5.055 5-OCH3, 2-F 3-CH2CN, 4-F, 6-F H H
5.056 5-OCH3, 2-F 3-CH2CN, 4-CI, 6-F H H
5.057 5-OCH3, 2-F 3-CH2CN, 4-CH3, H H 6-F
5.058 2-OCH2CH2CH3, 3-CH2CN H H resin 6-OCH3
5.059 2-CH3, 6-N-piperidyl 3-CH2CN H H resin
5.060 2-CFg, 5-OCH3 3-CH2CN H H crystalline
5.061 2-SCH3, 6-OCH3 3-CH2CN H H amorphous
5.062 2-CH3, 6-CI 3-CH2CN H H amorphous
5.063 2-SCH3, 5-OCH3 3-CH2CN H H 87-88
5.064 2-CH(CH3)2, 3-CH2CN H H resin 6-CH2OCH2CH3
5.065 5-NH2, 6-CI 3-CH2CN H H oil
Figure imgf000061_0001
Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
6.001 2-CN; 4-OCH3 5-CH2-CN H H
6.002 2-CI, 4-F 5-CH2-CN H H
6.003 2-CI, 4-CI 5-CH2-CN H H
6.004 2-F, 4-OCH3 5-CH2-CN H H
6.005 2-CI, 4-OCH3 5-CH2-CN H H
6.006 2-Br, 4-OCH3 5-CH2-CN H H
6.007 2-CFg, 4-CI 5-CH2-CN H H
6.008 2-CFg, 4-OCHg 5-CH2-CN H H
6.009 2-CHg, 4-OCH3 5-CH2-CN H H
6.010 2-CH=NOCH3, 4-OCH3 5-CH2-CN H H
6.01 1 2-CF3, 4-F 5-CH2-CN H H
6.012 4-OCH3 5-CH2-CN H H
6.013 2-CN; 4-OCH3 6-CI H H
6.014 2-CI, 4-F 6-CI H H
6.015 2-CI, 4-CI 6-CI H H
6.016 2-F, 4-OCH3 6-CI H H
6.017 2-CI, 4-OCH3 6-CI H H
6.018 2-Br, 4-OCH3 6-CI H H
6.019 2-CF3, 4-CI 6-CI H H
6.020 2-CF3, 4-OCH3 6-CI H H
6.021 2-CH3, 4-OCH3 6-CI H H
6.022 2-CH=NOCH3, 4-OCH3 6-CI H H
6.023 2-CF3, 4-F 6-CI H H
6.024 4-OCH3 6-CI H H
6.025 4-OCH3 6-CI F F Comp. Ri R2 R3 R Phys. data no. m.p. (°C)
6.026 2-CN, 4-OCH3 6-CH3 H H
6.027 2-CI, 4-F 6-CH3 H H
6.028 2-CI, 4-CI 6-CH3 H H
6.029 2-F, 4-OCH3 6-CH3 H H
6.030 2-CI, 4-OCH3 6-CH3 H H
6.031 2-Br, 4-OCH3 6-CH3 H H
6.032 2-CF3, 4-CI 6-CH3 H H
6.033 2-CF3, 4-OCH3 6-CH3 H H
6.034 2-CH3, 4-OCH3 6-CH3 H H
6.035 2-CH=NOCH3, 4-OCH3 6-CH3 H H
6.036 2-CFg, 4-F 6-CH3 H H
6.037 4-OCH3 6-CH3 H H
6.038 4-OCH3 6-CH3 F F
Table 7: Compounds of formula lb?1 :
Figure imgf000062_0001
Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
7.001 5-Br 3-CI H H
7.002 5-CI 3-CI H H
7.003 5-F 3-CI H H
7.004 4-CH3, 6-CH3 3-CI H H
7.005 4-CF3, 6-CF3 3-CI H H
7.006 5-Br 3-CH2-CN H H solid
7.007 5-CI 3-CH2-CN H H
7.008 5-F 3-CH2-CN H H 95-96
7.009 4-CH3, 6-CH3 3-CH2-CN H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
7.010 4-CF3, 6-CF3 3-CH2-CN H H
7.011 5-Br 3-CH2-CN F F
7.012 5-Br 3-CH2-CN, 4-F H H
7.013 5-Br 3-CH(CH3)CN H H
7.014 H 3-CH2-CN H H 98
7.015 H 3-CI H H oil
7.016 5-Br 3-CI H H 132-133
7.017 5-Br 3-Br H H 142-143
7.018 H 3,4-OCF2O- H H 94-95
7.019 4-CF3 3-CH2CN H H resin
7.020 5-CI 3-CH2-CN, 4-CI, 6-F H H 152-154
7.021 5-CI 3-CH2-CN H H 116-118
7.022 5-CI 3-CH2-CN, 4-F H H solid
7.023 5-F 3-CH2-CN, 6-F H H 96-97
7.024 5-CH2CH2CH3 3-CH2-CN H H resin
7.025 4-OC2H5, 6-OC2H5 3-CH2-CN H H oil
7.026 5-F 3-CH2-CN, 4-CI, 6-F H H 163-164
7.027 5-F 3-CH2-CN, 4-F H H solid
7.028 5-CI 3-CH2-CN, 6-F H H 108-110
7.029 5-Br 3-OCH2COOCH3 H H 95-97
7.030 5-CI 3-OCH2COOCH3 H H 90-91
7.031 5-CI 3-CH2-CN, 4-F, 6-F H H oil
7.032 5-CI 3-CH2-CN, 4-NO2 H H 106-109
7.033 5-CF3 3-CH2CN H H
7.034 5-CF3 3-CH(CH3)CN H H
7.035 5-CF3 3-CI H H
7.036 5-CF3 3-CH2-CN, 4-F H H
7.037 5-CF3 3-CH(CH3)CN, 4-F H H
7.038 5-CF3 3-CH2-CN, 6-F H H
7.039 5-CF3 3-CH(CH3)CN, 6-F H H
7.040 5-CF3 3-CH2-CN, 4-F, 6-F H H
Figure imgf000064_0001
Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
7.067 5-Br 3-CH(CH3)CN, 4-CI, H H 5-F
7.068 5-Br 3-CI, 6-F H H
7.069 5-Br 3-CH2-CN, 4-CN H H
7.070 5-Br 3-CH2-CN, 4-CH3 H H
7.071 5-Br 3-CH(CH3)CN, H H
Figure imgf000065_0001
7.072 5-Br 3-Br H H
7.073 5-Br 3-I H H
7.074 5-Br 3-I, 6-F H H
7.075 5-Br 3-CH2-CN, 4-NO2 H H
7.076 5-Br 3-CH2-CN, 4-NH2 H H
7.077 5-Br 3-CHF2 H H
7.078 * 5-Br 3-CHF2, 4-F H H
7.079 5-Br 3-CHF2, 6-F H H
7.080 5-Br 3-CHF2, 4-F, 6-F H H
7.081 5-CI 3-CH2CN H H
7.082 5-CI 3-CH(CH3)CN H H
7.083 5-CI 3-CI H H
7.084 5-CI 3-CH2-CN, 4-F H H
7.085 5-CI 3-CH(CH3)CN, 4-F H H
7.086 5-CI 3-CH2-CN, 6-F H H
7.087 5-CI 3-CH(CH3)CN, 6-F H H
7.088 5-CI 3-CH2-CN, 4-F, 6-F H H
7.089 5-CI 3-CH(CH3)CN, 4-F, H H 6-F
7.090 5-CI 3-CH2-CN, 4-CI, 5-F H H
7.091 5-CI 3-CH(CH3)CN, 4-CI, H H 5-F
7.092 5-CI 3-CI, 6-F H H
7.093 5-CI 3-CH2-CN, 4-CN H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
7.094 5-CI 3-CH2-CN, 4-CH3 H H
7.095 5-CI 3-CH(CH3)CN, H H
Figure imgf000066_0001
7.096 5-CI 3-Br H H
7.097 5-CI 3-1 H H
7.098 5-CI 3-1, 6-F H H
7.099 5-CI 3-CH2-CN, 4-NO2 H H
7.100 5-CI 3-CH2-CN, 4-NH2 H H
7.101 5-CI 3-CHF2 H H
7.102 5-CI 3-CHF2, 4-F H H
7.103 5-CI 3-CHF2, 6-F H H
7.104 5-CI 3-CHF2, 4-F, 6-F H H
7.105 5-F 3-CH2CN H H
7.106 5-F 3-CH(CH3)CN H H
7.107 5-F 3-CI H H
7.108 5-F 3-CH2-CN, 4-F H H
7.109 5-F 3-CH(CH3)CN, 4-F H H
7.110 5-F 3-CH2-CN, 6-F H H
7.1 11 5-F 3-CH(CH3)CN, 6-F H H
7.112 5-F 3-CH2-CN, 4-F, 6-F H H
7.113 5-F 3-CH(CH3)CN, 4-F, H H 6-F
7.114 5-F 3-CH2-CN, 4-CI, 6-F H H
7.115 5-F 3-CH(CH3)CN, 4-CI, H H .6-F
7.1 16 5-F 3-CI, 6-F H H
7.117 5-F 3-CH2-CN, 4-CN H H
7.1 18 5-F 3-CH2-CN, 4-CH3 H H
7.1 19 5-F 3-CH(CH3)CN, H H
7.120 5-F 3-Br H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
7.121 5-F 3-1 H H
7.122 5-F 3-1, 6-F H H
7.123 5-F 3-CH2-CN, 4-NO2 H H
7.124 5-F 3-CH2-CN, 4-NH2 H H
7.125 5-F 3-CHF2 H H
7.126 5-F 3-CHF2, 4-F H H
7.127 5-F 3-CHF2, 6-F H H
7.128 5-F 3-CHF2, 4-F, 6-F H H
7.129 5-CN 3-CH2CN H H
7.130 5-CN 3-CH(CH3)CN H H
7.131 5-CN 3-CI H H
7.132 5-CN 3-CH2-CN, 4-F H H
7.133 5-CN 3-CH(CH3)CN, 4-F H H
7.134 5-CN 3-CH2-CN, 6-F H H
7.135 5-CN 3-CH(CH3)CN, 6-F H H
7.136 5-CN 3-CH2-CN, 4-F, 6-F H H
7.137 5-CN 3-CH(CH3)CN, 4-F, H H 6-F
7.138 5-CN 3-CH2-CN, 4-CI, 6-F H H
7.139 5-CN 3-CH(CH3)CN, 4-CI, H H 6-F
7.140 5-CN 3-CI, 6-F H H
7.141 5-CN 3-CH2-CN, 4-CN H H
7.142 5-CN 3-CH2-CN, 4-CH3 H H
7.143 5-CN 3-CH(CH3)CN, H H 4-CH3
7.144 5-CN 3-Br H H
7.145 5-CN 3-1 H H
7.146 5-CN 3-1, 6-F H H
7.147 5-CN 3-CH2-CN, 4-NO2 H H
7.148 5-CN 3-CH2-CN, 4-NH2 H H
Figure imgf000068_0001
Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
7.176 5-CH3 3-CHF2, 4-F, 6-F H H
7.177 5-CH2CH3 3-CH2CN H H
7.178 5-CH2CH3 3-CH(CH3)CN H H
7.179 5-CH2CH3 3-CI H H
7.180 5-CH2CH3 3-CH2-CN, 4-F H H
7.181 5-CH2CH3 3-CH(CH3)CN, 4-F H H
7.182 5-CH2CH3 3-CH2-CN, 6-F H H
7.183 5-CH2CH3 3-CH(CH3)CN, 6-F H H
7.184 5-CH2CH3 3-CH2-CN, 4-F, 6-F H H
7.185 5-CH2CH3 3-CH(CH3)CN, 4-F, H H 6-F
7.186 5-CH2CH3 3-CH2-CN, 4-CI, 6-F H H
7.187 5-CH2CH3 3-CH(CH3)CN, 4-CI, H H 6-F
7.188 5-CH2CH3 3-CI, 6-F H • H
7.189 5-CH2CH3 3-CH2-CN, 4-CN H H
7.190 5-CH2CH3 3-CH2-CN, 4-CH3 H H
7.191 5-CH2CH3 3-CH(CH3)CN, H H
Figure imgf000069_0001
7.192 5-CH2CH3 3-Br H H
7.193 5-CH2CH3 3-1 H H
7.194 5-CH2CH3 3-1, 6-F H H
7.195 5-CH2CH3 3-CH2-CN, 4-NO2 H H
7.196 5-CH2CH3 3-CH2-CN, 4-NH2 H H
7.197 5-CH2CH3 3-CHF2 H H
7.198 5-CH2CH3 3-CHF2, 4-F H H
7.199 5-CH2CH3 3-CHF2, 6-F H H
7.200 5-CH2CH3 3-CHF2, 4-F, 6-F H H
7.201 5-CH(CH3)2 3-CH2CN H H
7.202 5-CH(CH3)2 3-CH(CH3)CN H H
7.203 5-CH(CH3)2 3-CI H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
7.204 5-CH(CH3)2 3-CH2-CN, 4-F H H
7.205 5-CH(CH3)2 3-CH(CH3)CN, 4-F H H
7.206 5-CH(CH3)2 3-CH2-CN, 6-F H H
7.207 5-CH(CH3)2 3-CH(CH3)CN, 6-F H H
7.208 5-CH(CH3)2 3-CH2-CN, 4-F, 6-F H H
7.209 5-CH(CH3)2 3-CH(CH3)CN, 4-F, H H 6-F
7.210 5-CH(CH3)2 3-CH2-CN, 4-CI, 5-F H H
7.21 1 5-CH(CH3)2 3-CH(CH3)CN, 4-CI, H H 5-F
7.212 5-CH(CH3)2 3-CI, 6-F H H
7.213 5-CH(CH3)2 3-CH2-CN, 4-CN H H
7.214 5-CH(CH3)2 3-CH2-CN, 4-CH3 H H
7.215 5-CH(CH3)2 3-CH(CH3)CN, H H 4-CH3
■ 7.216 5-CH(CH3)2 3-Br H H
7.217 5-CH(CH3)2 3-1 H H
7.218 5-CH(CH3)2 3-1, 6-F H H
7.219 5-CH(CH3)2 3-CH2-CN, 4-NO2 H H
7.220 5-CH(CH3)2 3-CH2-CN, 4-NH2 H H
7.221 5-CH(CH3)2 3-CHF2 H H
7.222 5-CH(CH3)2 3-CHF2, 4-F H H
7.223 5-CH(CH3)2 3-CHF2, 6-F H H
7.224 5-CH(CH3)2 3-CHF2, 4-F, 6-F H H
7.225 5-CH2CH2CH3 3-CH2CN H H
7.226 5-CH2CH2CH3 3-CH(CH3)CN H H
7.227 5-CH2CH2CH3 3-CI H H
7.228 5-CH2CH2CH3 3-CH2-CN, 4-F H H
7.229 5-CH2CH2CH3 3-CH(CH3)CN, 4-F H H
7.230 5-CH2CH2CH3 3-CH2-CN, 6-F H H
7.231 5-CH2CH2CH3 3-CH(CH3)CN, 6-F H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
7.232 5-CH2CH2CH3 3-CH2-CN, 4-F, 6-F H H
7.233 5-CH2CH2CH3 3-CH(CH3)CN, 4-F, H H 6-F
7.234 5-CH2CH2CH3 3-CHa-CN, 4-CI, 6-F H H
7.235 5-CH2CH2CH3 3-CH(CH3)CN, 4-CI, H H 6-F
7.236 5-CH2CH2CH3 3-CI, 6-F H H
7.237 5-CH2CH2CH3 3-CH2-CN, 4-CN H H
7.238 5-CH2CH2CH3 3-CH2-CN, 4-CH3 H H
7.239 5-CH2CH2CH3 3-CH(CH3)CN, H H
Figure imgf000071_0001
7.240 5-CH2CH2CH3 3-Br H H
7.241 5-CH2CH2CH3 3-1 H H
7.242 5-CH2CH2CH3 3-1, 6-F H H
7.243 5-CH2CH2CH3 3-CH2-CN, 4-NO2 H H
7.244 5-CH2CH2CH3 3-CH2-CN, 4-NH2 H H
7.245 5-CH2CH2CH3 3-CHF2 H H
7.246 5-CH2CH2CH3 3-CHF2, 4-F H H
7.247 5-CH2CH2CH3 3-CHF2, 6-F H H
7.248 5-CH2CH2CH3 3-CHF2, 4-F, 6-F H H
7.249 5-CH=NOCH3 3-CH2CN H H
7.250 5-CH=NOCH3 3-CH(CH3)CN H H
7.251 5-CH=NOCH3 3-CI H H
7.252 5-CH=NOCH3 3-CH2-CN, 4-F H H
7.253 5-CH=NOCH3 3-CH(CH3)CN, 4-F H H
7.254 5-CH=NOCH3 3-CH2-CN, 6-F H H
7.255 5-CH=NOCH3 3-CH(CH3)CN, 6-F H H
7.256 5-CH=NOCH3 3-CH2-CN, 4-F, 6-F H H
7.257 5-CH=NOCH3 3-CH(CH3)CN, 4-F, H H 6-F
7.258 5-CH=NOCH3 3-CH2-CN, 4-CI, 6-F H H Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
7.259 5-CH=NOCH3 3-CH(CH3)CN, 4-CI, H H 6-F
7.260 5-CH=NOCH3 3-CI, 6-F H H
7.261 5-CH=NOCH3 3-CH2-CN, 4-CN H H
7.262 δ-CH-NOCHg 3-CH2-CN, 4-CH3 H H
7.263 5-CH=NOCH3 3-CH(CH3)CN, H H 4-CH3
7.264 5-CH=NOCH3 3-Br H H
7.265 5-CH=NOCH3 3-1 H H
7.266 5-CH=NOCH3 3-1, 6-F H H
7.267 5-CH-=NOCH3 3-CH2-CN, 4-NO2 H H
7.268 5-CH=NOCH3 3-CH2-CN, 4-NH2 H H
7.269 5-CH=NOCH3 3-CHF2 H H
7.270 5-CH=NOCH3 3-CHF2, 4-F H H
7.271 5-CH=NOCH3 3-CHF2, 6-F H H
7.272 5-CH=NOCH3 3-CHF2, 4-F, 6-F H H
7.273 H (n = 0) 3-CHF2, 4-F, 6-F H H
7.274 H (n = 0) 3-CHF2, 4-CI, 6-F H H
7.275 H (n = 0) 3-CHF2, 4-F H H
7.276 H (n = 0) 3-CHF2, 6-F H H
7.277 H (n = 0) 3-CHF2 H H
7.278 H (n = 0) 3-CH2-CN, 4-F, 6-F H H
7.279 H (n = 0) 3-CH2-CN, 4-CI, 6-F H H
7.280 H (n = 0) 3-CH2-CN, 4-F H H
7.281 H (n = 0) 3-CH2-CN, 6-F H H
7.282 H (n = 0) 3-CH2-CN H H Comp. Ri R2 Rs R4 Phys. data no. m.p. (°C)
7.283 H (n = 0) 3-CH(CH3)CN, H H 4-F, 6-F
7.284 H (n = 0) 3-CH(CH3)CN, H H 4-F
7.285 H (n = 0) 3-CH(CH3)CN, H H 6-F
7.286 H (π = 0) 3-CH(CH3)CN H H
7.287 H (n = 0) 3-CI H H
7.288 H (n = 0) 3-Br H H
7.289 H (n = 0) 3-F H H
7.290 H (n = 0) 3-CH3 H H
7.291 H (n = 0) 3-1 H H
Table 8: Compounds of formula leg1 :
Figure imgf000073_0001
Comp. Ri R2 R3 R4 Phys. data no. m.p. (°C)
8.001 3-CN, 5-OCHg 3-CH2-CN H H
8.002 3-CI, 5-F 3-CH2-CN H H
8.003 3-CI, 5-CI 3-CH2-CN H H
8.004 3-F, 5-OCHg 3-CH2-CN H H
8.005 3-CI, 5-OCH3 3-CH2-CN H H
8.006 3-Br, 5-OCH3 3-CH2-CN H H
8.007 3-CF3, 5-CI 3-CH2-CN H H
8.008 3-CF3, 5-OCH3 3-CH2-CN H H
8.009 3-CH3, 5-OCH3 3-CH2-CN H H
8.010 3-CH=NOCH3, 5-OCH3 3-CH2-CN H H Comp. Rϊ R2 R3 R4 Phys. data no. m.p. (°C)
8.011 3-CF3, 5-F 3-CH2-CN H H
8.012 5-OCH3 3-CH2-CN H H
8.013 5-OCH3 3-CH2-CN F F
8.014 5-OCH3 3-CHF2 H H
8.015 5-OCH3 3-CHF2, 4-F H H
8.016 H (n = 0) 3-CH2-CN H H
8.017 H (n = 0) 3-CHF2 H H
8.018 H (n = 0) 3-CHF2, 4-F H H
8.019 H (n = 0) 3-CH2-CN, 4-F H H
Table 9: Compounds of formula lc31 :
Figure imgf000074_0001
Figure imgf000075_0001
Biological Examples
Example B1 : Herbicidal action prior to emergence of the plants (pre-emerqence action) Monocotyledonous and dicotyledonous test plants are sown in standard soil in pots. Immediately after sowing, the test compounds, in the form of an aqueous suspension (prepared from a wettable powder (Example F3, b) according to WO 97/34485) or in the form of an emulsion (prepared from an emulsifiable concentrate (Example F1 , c) according to WO 97/34485), are applied by spraying, in an optimum concentration (500 litres of water per ha). The test plants are then grown in a greenhouse under optimum conditions. After a test duration of 4 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.
Test plants: Panieum (Pani), Digitaria (Digit), Euphorbia (Euph), Sida, Abutilon (Abut), Amaranthus (Amar), Chenopodium (Cheno), Stellaria (Stell).
Figure imgf000076_0001
The same results are obtained when the compounds of formula I are formulated analogously to the other Examples of WO 97/34485.
Example B2: Post-emergence herbicidal action
Monocotyledonous and dicotyledonous test plants are sown in standard soil in pots. When the test plants are at the 2- to 3-leaf stage, the test compounds, in the form of an aqueous suspension (prepared from a wettable powder (Example F3, b) according to WO 97/34485) or in the form of an emulsion (prepared from an emulsifiable concentrate (Example F1 , c) according to WO 97/34485), are applied by spraying, in an optimum concentration (500 litres of water per ha). The test plants are then grown on in a greenhouse under optimum conditions.
After a test duration of 2 to 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. Test plants: Panieum (Pani), Euphorbia (Euph), Abutilon (Abut), Amaranthus (Amara), Stellaria (Stell), Veronica (Vero).
Figure imgf000077_0001
In the two Tables above, "-" means that there are no data available for the compounds and weeds in question.
The same results are obtained when the compounds of formula I are formulated analogously to the other Examples of WO 97/34485.

Claims

What is claimed is:
1. A compound of formula I
Figure imgf000078_0001
wherein Q is a group
(Q3),
Figure imgf000078_0002
Figure imgf000078_0003
Z is =N-, I + - or =C(R2)- ;
=N-0 n is 0, 1 , 2 or 3; each Ri independently is halogen, -CN, -SCN, -SF5, -NO2, -NR5R6, -CO2R7, -CONR8R9, -C(Rιo)=NORιι, -COR12, -OR13, -SRι4, -SOR15, -SO2Rι6, -OSO2R17, Cι-C8al yl, C2-C8alkenyl, C2-C8alkynyl or C3-C6cycloalkyl; or is C C8alkyl, C2-C8alkenyl or C2-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -N02, - Rι8 i9, -CO2R20, -CONR21R22, -COR23,
Figure imgf000078_0004
- OR29, -SR30, -SOR31, -SO2R32 or by C3-C6cycloalkyl; or each Ri independently is C3-C6cycloalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -NO2, -NR18R19, -CO2R20, -CONR21R22, -COR23, -C(R24)-=-NOR25, -C(S)NR26R27, -C(C C4alkylthio)=NR28, -SR30, -SOR31, -SO2R32 or by C3-C6cycloalkyi; or each R. independently is phenyl which may in turn be mono- to penta-substituted by halogen or by CrC4alkyl or mono-, di- or tri-substituted by d-C4haloalkyl, CrC alkoxy, -CN, -NO2, C C alkylthio, C C4alkylsulfinyl or by C C4alkylsulfonyl; or, when Q is a group Qi, Q2, Q3 or Q5) two adjacent Ri substituents may together form a d-C7alkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which may be mono- to penta-substituted by halogen or by C1-C6alkyl or mono-, di- or tri-substituted by C C6alkoxy, the total number of ring atoms being at least 5 and at most 9; or, when Q is a group Qi, Q2, Q3 or Q5, two adjacent Ri substituents may together form a C2-C7alkenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and which may be mono- to penta-substituted by halogen or by CrC6alkyl or mono-, di- or tri-substituted by C C6alkoxy, the total number of ring atoms being at least 5 and at most 9;
R3 or R are each independently of the other hydrogen, halogen, -CN, C C4alkyl or CrC alkoxy; or
R3 and R4 together are C2-C5alkylene; R5 is hydrogen or C-ι-C8alkyl;
R6 is hydrogen, CrC8alkyl, C3-C8a!kenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C C alkyl or mono-, di- or tri-substituted by C C haloalkyl, Cι-C alkoxy, -CN, -NO2, CrC4alkylthio, CrC4alkyIsulfinyl or by C C alkylsulfonyl; or
R5 and R6 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R7 is hydrogen, CrC8alkyl, C3-C8alkenyl or C3-C8alkynyl, or is C C8alkyl, C3-C8alkenyl or C3-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by CrC4alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta- substituted by halogen or by C1-C alkyl or mono-, di- or tri-substituted by C C4haloalkyl, C C alkoxy, -CN, -NO2, CrC alkylthio, C C4alkylsulfinyl or by CrC4alkylsulfonyl; R8 is hydrogen or CrC8alkyl;
R9 is hydrogen or C C8alkyl, or is C C8alkyl mono-, di- or tri-substituted by -COOH, CrC8alkoxycarbonyl or by -CN, or
R9 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C C4alkyl or mono-, di- or tri- substituted by C C4haloalkyl, C C alkoxy, -CN, -NOz, C C4alkylthio, C C4alkylsulfinyl or by CrC4alkylsulfonyl; or R8 and R9 together are C2-C5alkylene; R10 is hydrogen, C C4alkyl, C C haloalkyl or C3-C6cycloalkyl; Rn is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, C C4haloalkyl or C3-C6haloalkenyl; R 2 is hydrogen, d-C4alkyl, C C haIoalkyl or C3-C6cycloalkyl; R13 is hydrogen, C C8alkyl, C3-C8alkenyl or C3-C8alkynyl; or
R13 is phenyl or phenyl-CrC6alkyl, it being possible for the phenyl ring in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-C halo- alkyl, C C alkoxy, -CN, -NO2, C C8alkylthio, C C8alkylsulfinyl or by d-C8alkylsu.fonyl, or R13 is d-dalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, C C6alkylamino, di(C C6alkyl)amino or by d-C alkoxy;
R14 is hydrogen, C C8alkyl, C3-C8alkenyl or C3-C8aikynyl, or is d-C8alkyl mono- to penta- substituted by halogen or mono-, di- or tri-substituted by -CN or by d-C4alkoxy; R15, R-I6 and R17 are each independently of the others CrC8alkyl, C3-C8alkeny! or C3-C8alkynyl, or d-C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by C C alkoxy; R18 is hydrogen or Crdalkyl;
R19 is hydrogen, C C8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-C haloalkyl, d-C alkoxy, -CN, -NO2, C C4alkylthio, C C4alkylsulfinyl or by d-C alkylsulfonyi; or
R18 and R19 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R20 is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by Cι-C4alkyl or mono-, di- or tri-substituted by C C haloalkyl, C C alkoxy, -CN, -NO2, C C4alkylthio, C C4alkylsulfinyl or by C1-C4alkylsulfonyl; R21 is hydrogen or CrC8alkyl;
R22 is hydrogen or CrC8alkyl, or is d-C8aIkyl mono-, di- or tri-substituted by -COOH, C C8alkoxycarbonyl or by -CN, or
R22 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by C C alkyl or mono-, di- or tri- substituted by C C4haloalkyl, CrC alkoxy, -CN, -NO2, d-dalkylthio, C C alkylsulfinyl or by d-dalkylsulfonyl; or R21 and R22 together are C2-C5alkylene; R23 is hydrogen, d-dalkyl, d-C haloalkyl or C3-C6cycloa!kyl; R24 is hydrogen, C C4alkyl, C C haloalkyl or C3-C6cycloalkyl;
R25 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; R26 is hydrogen or C C8alkyl; R27 is hydrogen or C C8alkyl, or is d-C8alkyl mono-, di- or tri-substituted by -COOH, d-C8- alkoxycarbonyl or by -CN, or
R27 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by CrC4alkyl or mono-, di- or tri- substituted by d-dhaloalkyl, CrC4alkoxy, -CN, -NO2, C C alkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R26 and R27 together are C2-C5alkylene; R28 is hydrogen or d-C8alkyl;
R29 and R30 are each independently of the other hydrogen, d-C8alkyl, C3-C8alkenyi or C3-C8alkynyl, or d-C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by C C aIkoxy;
R31 and R32 are each independently of the other d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or d-dalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN or by d-C4alkoxy; m is 0, 1 , 2, 3 or 4; each R2 independently is halogen, -CN, -SCN, -OCN, -N3, -SF5, -NO2, -NR33R34, -CO2R35, -CONR36R37, -C(R38)=NOR39, -COR40, -OR4ι, -SR42, -SOR43, -SO2R44, -OSO2R45, -N([CO]pR46)COR47, -N(OR54)COR55, -N(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR60)R61, -CR62(OR63)OR6 , -OC(O)NR65R66, -SC(O)NR67R68, -OC(S)NR69R7o or -N-phthalimide; or R2 is a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for that heterocyclic ring system in turn to be mono- to penta- substituted by halogen or by C C4alkyl or mono-, di- or tri-substituted by C C4haloalkyl, hydroxy-d-dalkyl, C C4alkoxy, C C alkoxy-CrC alkyl, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C6alkylsulfonyl; R33 is hydrogen or d-dalkyl; and
R34 is hydrogen, Cι-C8alky), C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-C4haloalkyl, C C4alkoxy, -CN, -NO2, C C4alkylthio, d-dalkylsulfinyl or by C C4alkylsulfonyl; or
R33 and R34 together are a C2-C5a!kylene chain which may be interrupted by an oxygen or sulfur atom;
R35 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is C C8alkyl, C3-C8alkenyl or C3-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta- substituted by halogen or by d-C4alkyl or mono-, di- or tri-substituted by d-C4haloalkyl, d-dalkoxy, -CN, -NO2, d-C4alkylthio, C C alkylsulfinyl or by d-dalkylsulfonyl; R36 is hydrogen or d-dalkyl;
R37 is hydrogen or d-dalky), or is Crdalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R37 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, C C4alkoxy, -CN, -NO , d-C4alkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R36 and R37 together are C3-C5alkylene; R38 is hydrogen, d-C atkyl, d-dhaloalkyl or C3-C6cycloalkyl;
R39 is hydrogen, C C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C C4haloalkyl or C3-C6haloalkenyl; R40 is hydrogen, C C4alkyl, C C haloalkyl, C C8alkylthio, -C(O)-C(O)Od-C4alkyl or C3-C6- cycloalkyl;
R41 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C C6alkoxy-CrC6alkyl, Crdalkyl- carbonyl, C1-C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, Cι-C6alkoxy-CrC6alkoxycarbonyl, Cι-C6alkylthio-CrC6alkyl, d-dalkylsulfinyl-Crdalkyl or d-dalkylsulfonyl-Crdalky); or R4ι is phenyl or phenyl-Crdaikyl, it being possible for the phenyl ring in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2 or by -S(O)2d-C8alkyl, or
R4ι is d-dalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -COOH, d-C8alkoxycarbonyl, Crdalkylamino, di(C C6alkyl)amino or by -CN; R42 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl mono- to penta- substituted by halogen or mono-, di- or tri-substituted by -CN or by d-dalkoxy; R 3 and R are each independently of the other CrC8alkyl, C3-C8alkenyl or C3-C8alkynyl, or d-dalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN or by d-dalkoxy;
R 5 is d-dalkyl, d-C8alkyl mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by d-dalkoxy, or is C3-C8alkenyl or C3-C8alkynyl, or R45 is phenyl, it being possible for the phenyl ring to be mono- to penta-substituted by halogen or by C C4alkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-C4alkoxy, -CN, NO2, d-dalkylthio, d-dalkylsulfinyl 0r by d-dalkylsulfonyl; R46 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl or CrC4haloalkyl; R is hydrogen, d-dalkyl, d-C4alkoxy, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, d-C4alkoxy, d-dalkoxycarbonyl, -NH2, Crdalkylamino, di(CrC alkyl)amino, -NR 8COR 9, -NR50SO2R5ι or by -NR52CO2R53, or
R 7 is phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta- substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; p is 0 or 1 ;
R48, R49, R5o, R51, Rδ2 and R53 are each independently of the others hydrogen, d-dalkyl, phenyl, benzyl or naphthyl, it being possible for the three last-mentioned aromatic radicals in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, Crdalkylamino, di(d-C4alkyl)amino, -NH2, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R5 and R55 are each independently of the other hydrogen, d-dalkyl, or phenyl which may in turn be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R56 is hydrogen, d-dalkyl, d-C4haloalkyl, d-dalkoxy, C3-C8alkenyl, C3-C8alkynyl or benzyl, it being possible for benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-C alkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R57 is Crdalkyl, d-C4haloalkyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, Crdalkylamino, di(CrC alkyl)amino, -NH2, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C4alkylsulfonyl; R58 and R59 are each independently of the other d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, Crdalkylamino, di(C C4alkyl)amino, -NH2, -CN, -NO2, C C4alkylthio, d-dalkylsulfinyl or by C C alkylsulfonyl;
R60 and R6ι are each independently of the other hydrogen or Crdalkyl; R62, R63 and R64 are each independently of the others hydrogen or d-C8alkyl, or R63 and R6 together form a C2-C5alkylene bridge;
Res, Ree. Re7, Reβ, Reg and R70 are each independently of the others hydrogen or d-dalkyl, or
R65 and R66, or R67 and R68, or R69 and R70 in each case together form a C2-C5alkylene bridge; or each R2 independently is d-C8alkyl, or is d-dalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -N3, -SCN, -NO2, -NR71R72, -CO2R73, -CONR74R75,
-COR76, -C(R77)=NOR78, -C(S)NR79R80, -C(C C4alkylthio)=NR81, -OR82, -SR83, -SOR84,
-SO2R85, -O(SO2)R86, -N(R87)CO2R88, -N(R89)COR90, -S+(R9ι)2, -N+(R92)3, -Si(R93)3 or by
C3-dcycloalkyl; or each R2 independently is d-dalkyl substituted by a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from oxygen, nitrogen and sulfur, it being possible for that heterocyclic ring system in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, hydroxy-C C alkyl, d-dalkoxy, d-dalkoxy-d-dalkyl, -CN, -NO2, Crdalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or each R2 independently is C2-C8alkenyl, or is C2-C8alkenyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -NO2, -CO2R94, -CONR95R96, -COR97,
-C(R98)=NOR99, -C(S)NR100R10ι, -C(CrC4alkylthio)=NR102, -OR103, -Si(R104)3 or by C3-C6- cycloalkyl; or each R2 independently is C2-C8alkynyl, or is C2-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -CO2Rι05, -CONR106R107, -CORι08,
-C(R109)=NOR110, -dSJNR^R , -C(C C4alkylthio)=NR113, -OR114, -Si(R115)3 or by d-dcycloalkyl; or each R2 independently is C3-C6cycloalkyl, or is C3-C6cycloalkyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -CO2Rn6, -CONRn7R118, -COR119,
-C(R120)=NOR12ι, -C(S)NR122R123 or by -C(C C4alkylthio)=NR124; or two adjacent R2 substituents together form a d-dalkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono- to penta-substituted by halogen or by d-dalkyl or mono:, di- or tri-substituted by Crdalkoxy, the total number of ring atoms being at least 5 and at most 9; or two adjacent R2 substituents together form a C2-C7alkenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dalkoxy, the total number of ring atoms being at least 5 and at most 9;
R71 is hydrogen or d-dalkyl;
R72 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by C C haloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R71 and R72 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R73 is hydrogen, d-C8a!kyl, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-C alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta- substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, -CN, -N02, C C4alkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R74 is hydrogen or d-dalkyl;
R75 is hydrogen, d-dalkyl or C3-C7cycloalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl, C C6alkoxy or by -CN; or
R75 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-C4alkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
R74 and R75 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R76 is hydrogen, d-dalkyl, d-C4haloalkyl or C3-C6cycloalkyl; R77 is hydrogen, d-dalkyl, C C4haIoalkyl or C3-C6cycloalkyl;
R78 is hydrogen, Crdalkyl, C3-C8alkenyl, C3-C8alkynyl, d-C4haloalkyl or C3-C6haloalkenyl; and
R 9 is hydrogen or d-dalkyl;
R80 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R80 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, Crdalkylthio, Crdalkylsulfinyl or by d-dalkylsulfonyl; or R79 and R80 together are C2-C5alkylene; R8 is hydrogen or Crdalkyl;
R82 is -Si(d-C6alkyl)3, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl which is mono- to penta- substituted by halogen or mono-, di- or tri-substituted by -CN, -NH2, C C6alkylamino, di(d-C6alkyl)amino or by d-dalkoxy;
R83 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is C C8alkyl which is mono- to penta-substituted by halogen or mono-, di- or tri-substituted by -CN, -NH2, Crdalkylamino, di(CrC6alkyl)amino or by C C4alkoxy; Rs4, Rδδ and R86 are each independently of the others d-dalkyl, C3-C8alkenyl or C3-C8- alkynyl, or C C8alkyl which is mono- to penta-substituted by halogen or mono-, di- or tri- substituted by -CN or by d-dalkoxy;
R87 and R89 are each independently of the other hydrogen, d-dalkyl or d-dalkoxy; R88 is d-dalkyl; R90 is hydrogen or d-dalkyl; R91 is d-dalkyl;
R92 and R93 are each independently of the other Crdalkyl;
R9 is hydrogen or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R95 is hydrogen or d-dalkyl;
R96 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-C8alkoxycarbonyl or by -CN; or
R96 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, C C4alkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R95 and R96 together are C2-C5alkylene;
R97 and Rg8 are each independently of the other hydrogen, d-dalkyl, C C4haloalkyl or C3-C6cycloalkyl;
R9 is hydrogen, Crdalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; R10o is hydrogen or d-dalkyl;
R10ι is hydrogen or Crdalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R101 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R100 and R10ι together are C2-C5alkylene; R102 is hydrogen or Crdalkyl;
Rι03 is hydrogen, d-dalkyl, -Si(CrC6alkyl)3, C3-C8alkenyl or C3-C8alkynyl; Rι04 is d-C6alkyl; R105 is hydrogen or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-C alkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, Crdalkylsulfinyl or by d-dalkylsulfonyl; R106 is hydrogen or d-dalkyl;
Ri07 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R107 is d-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, C C4aIkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R106 and R107 together are C2-C5alkylene; R-ios is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl; R10g is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl;
R110 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; Rm is hydrogen or d-dalkyl;
R112 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R112 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or Rm and R112 together are C2-C5alkylene; Rn3 is hydrogen or d-dalkyl;
R114 is hydrogen, d-dalkyl, -Si(d-C6alkyl)3, C3-C8alkenyl or C3-C8alkynyl; R115 is d-dalkyl;
R116 is hydrogen or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono- to penta-substituted by halogen or mono-, di- or tri-substituted by d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri-substituted by C C4haloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R117 is hydrogen or d-dalkyl;
Rns is hydrogen or d-dalkyl, or is C C8alkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or R118 is d-dalkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R117 and Rns together are C2-C5alkylene; R119 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl; R120 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl;
R121 is hydrogen, d-dalkyl, d-C8alkenyl, C3-C8alkynyl, d-C haloalkyl or C3-C6haloalkenyl; R122 is hydrogen or d-dalkyl;
R123 is hydrogen or Crdalkyl, or is Crdalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
Rι23 is d-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono- to penta-substituted by halogen or by d-dalkyl or mono-, di- or tri- substituted by d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or Rι22 and R123 together are C2-C5alkylene; and R12 is hydrogen or d-dalkyl, or an agrochemically acceptable salt or any stereoisomer or tautomer of a compound of formula I.
2. A compound of formula I wherein each
Figure imgf000088_0001
independently is halogen, -CN, -SCN, -SF5,
-NO2, -NR5Re, -CO2R7, -CONR8R9, -C(R10)=NORn, -COR12, -OR13, -SR14, -SORι5, -SO2R16,
-OSO2R17, d-dalkyl, C2-C8alkenyl, C2-C8alkynyl or C3-C6cycloalkyl; or is C C8alkyl,
C2-C8alkenyl or C2-C8alkynyl mono-, di- or tri-substituted by halogen, -CN, -NO2, -NRι8R19,
-CO2R20, -CONR21R22, -COR23, -C(R24)=NOR25, -C(S)NR26R27, -C(d-C4alkylthio)=NR28, -
OR29, -SR30, -SOR31, -SO2R32 or by C3-C6cycloalkyl; or each Ri independently is C3-C6cycloalkyl mono-, di- or tri-substituted by halogen, -CN, -NO2,
-NR18R19, -CO2R20, -CONR2ιR22, -COR23, -C(R24)=NOR25, -C(S)NR26R27, -C(CrC4alkyl- thio)=NR28, -SR30, -SOR31, -SO2R32 or by C3-C6cycloalkyl; or each Ri independently is phenyl which may in turn be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, C dalkylsulfinyl or by C C4alkylsulfonyl; or, when Q is a group Qi, Q2, Q3 or Q5, two adjacent R, substituents together may form a d-dalkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted by halogen, d-dalkyl or by d-C6alkoxy, the total number of ring atoms being at least 5 and at most 9; or, when Q is a group Qi, Q2, Q3 or Q5, two adjacent R, substituents together may form a C2-C7aikenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted by halogen, d-dalkyl or by d-dalkoxy, the total number of ring atoms being at least 5 and at most 9;
R3 or R4 are each independently of the other hydrogen, halogen, -CN, d-dalkyl or d-dalkoxy; or
R3 and R together are C2-C5alkylene; R5 is hydrogen or Crdalkyl;
R6 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C4alkylsulfonyl; or
R5 and R6 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R7 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R8 is hydrogen or C C8alkyl;
R9 is hydrogen or Crdalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R9 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-C4alkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C4alkylsulfonyl; or R8 and R9 together are C2-C5alkylene; Rio s hydrogen, Crdalkyl, d-dhaloalkyl or C3-C6cycIoalkyl; R11 s hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; Rι2 s hydrogen, d-dalkyl, d-C4haloalkyl or C3-C6cycloalkyl;
Rl3 s hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl; or Rl3 s phenyl or phenyl-d-dalkyl, it being possible for the phenyl ring in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, C C4haloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C8alkylsulfonyl; or
R13 is d-dalkyl mono-, di- or tri-substituted by halogen, -CN, d-dalkyiamino, di(C C6- alkyl)amino or by d-dalkoxy; Rι is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is C C8alkyl mono-, di- or tri- substituted by halogen, -CN or by d-dalkoxy;
R15, R16 and R17 are each independently of the others d-dalkyl, C3-C8alkenyl or C3-C8- alkynyl, or d-C8alkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy; Rι8 is hydrogen or d-dalkyl;
R19 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d- dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by Cr dalkylsulfonyl; or
R18 and R19 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R20 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, C dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, Crdalkylsulfinyl or by C dalkylsulfonyl; R2ι is hydrogen or Crdalkyl;
R22 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R22 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C4alkylsulfonyl; or R2ι and R22 together are C2-C5alkylene; R23 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl; R24 is hydrogen, d-dalkyl, CrC4haloalkyl or C3-C6cycloalkyl;
R25 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, C C4haloalkyl or C3-C6haloalkenyl; R26 is hydrogen or d-dalkyl;
R27 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R27 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, C C alkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R26 and R27 together are C2-C5alkylene; R28 is hydrogen or d-dalkyl;
R2g and R30 are each independently of the other hydrogen, d-dalkyl, C3-C8alkenyl or d-dalkynyl, or Crdalkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy; R3ι and R32 are each independently of the other d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or CrC8alkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy; m is 0, 1 , 2, 3 or 4; each R2 independently is hydrogen, halogen, -CN, -SCN, -OCN, -N3, -SF5, -N02, -NR33R34, -CO2R35, -CONR36R37, -C(R38)=NOR39, -COR40, -OR41, -SR42, -SOR43, -SO2R44, -OSO2R45, -N([CO]pR46)COR47, -N(OR54)COR55, -N(R56)SO2R57, -N(SO2R58)SO2R59, -N=C(OR6o)R6ι, -CR62(OR63)OR64, -OC(O)NR65R66, -SC(O)NR67R68l -OC(S)NR6gR7o or -N-phthalimide; or R2 is a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for that heterocyclic ring system in turn to be mono-, di- or tri- substituted by halogen, d-dalkyl, d-dhaloalkyl, hydroxy-d-C4alkyl, d-dalkoxy, d-dalkoxy-Crdatkyl, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R33 is hydrogen or d-dalkyl; and
R34 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C dalkylsulfonyl; or
R33 and R34 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R35 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R36 is hydrogen or d-dalkyl;
R37 is hydrogen or d-dalkyl, or is C C8alkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R37 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, C1-C4alkylsulfinyl or by d-dalkylsulfonyl; or R36 and R37 together are C3-C5alkylene; R38 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloaikyl;
R3g is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, C C4haloalkyl or C3-C6haloalkenyl; R40 is hydrogen, d-dalkyl, d-dhaloalkyl, d-dalkylthio, -C(O)-C(O)OC C4alkyl or C3-dcycloalkyl; R ι is hydrogen, CrC8alkyl, C3-C8alkenyl, C3-C8alkynyl, d-dalkoxy-Crdalkyl, d-dalkyl- carbonyl, C C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, d-dalkoxy-d-Cealkoxycarbonyl, CrC6alkylthio-CrC6alkyl, CrC6alkylsulfinyl-CrC6alkyl or Cι-C6alkylsulfonyl-CrCβalkyl; or R41 is phenyl or phenyl-d-dalkyl, it being possible for the phenyl ring in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, C C4haloalkyl, d-dalkoxy, -CN, -NO2 or by -S(O)2CrC8alkyl, or
R4ι is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl, Crdalkylamino, di(Crdalkyl)amino or by -CN;
R42 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl mono-, di- or tri- substituted by halogen, -CN or by d-dalkoxy;
R 3 and R44 are each independently of the other Crdalkyl, C3-C8alkenyl or C3-C8alkynyl, or d-dalkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy; R45 is Crdalkyl, d-dalkyl mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy, or is C3-C8alkenyl or C3-C8alkynyl, or
R45 is phenyl, it being possible for the phenyl ring to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R46 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl or d-dhaloalkyl; R47 is hydrogen, d-dalkyl, d-dalkoxy, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl mono-, di- or tri-substituted by halogen, -CN, d-dalkoxy, d-C8alkoxycarbonyl, -NH2, d-dalkylamino, di(d-C4alkyl)amino, -NR48COR49, -NR50SO2R5ι or by -NR52CO2R53, or R47 is phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri- substituted by halogen, d-dalkyl, d-C4haloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by C C alkylsulfonyl; p is 0 or 1 ;
R48, R49, R50, R51, R52 and R53 are each independently of the others hydrogen, d-dalkyl, phenyl, benzyl or naphthyl, it being possible for the three last-mentioned aromatic radicals in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C4haIoalkyl, d-dalkoxy, d-dalkylamino, di(Cι-C4alkyl)amino, -NH2, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R5 and R55 are each independently of the other hydrogen, d-dalkyl, or phenyl which may in turn be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2> d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R56 is hydrogen, d-dalkyl, C C4haloalkyl, CrC4alkoxy, C3-C8alkenyl, C3-C8alkynyl or benzyl, it being possible for benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, CrC haloalkyl, C C alkoxy, -CN, -N02, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R57 is d-dalkyl, CrC haloalkyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono-, di- or tri-substituted by halogen, d-dalkyl, C dhaloalkyl, d-dalkoxy, d-dalkylamino, di(C C4alkyl)amino, -NH2, -CN, -NO2, d- C4alkyIthio, d-C4alkylsulfinyl or by d-dalkylsulfonyl;
R58 and R59 are each independently of the other d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl, benzyl or naphthyl, it being possible for the last three aromatic rings to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dalkylamino, di(CrC4alkyl)amino, -NH2, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R60 and R61 are each independently of the other hydrogen or d-dalkyl; R62, Rδ3 and R64 are each independently of the others hydrogen or d-dalkyl, or R63 and R64 together form a C2-C5alkylene bridge;
R65> Ree, Re7, Res, Reg and R70 are each independently of the others hydrogen or d-dalkyl, or
R65 and R66, or R67 and R6s. or R69 and R70 in each case together form a C2-C5alkylene bridge; or each R2 independently is d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by halogen, -CN, -N3, -SCN, -NO2, -NR7ιR72. -CO2R73, -CONR74R75, -COR76, -C(R77)=NOR78, -C(S)NR7gR80, -C(C C4alkylthio)=NR81, -OR82, -SR83, -SOR84, -SO2R85, -O(SO2)R86, -N(R87)CO2R88, -N(R89)COR9o, -S+(R91)2, -N+(R92)3, -Si(R93)3 or by C3-C6cycloalkyl; or each R2 independently is d-dalkyl substituted by a 5- to 7-membered heterocyclic ring system which may be aromatic or partially or fully saturated and may contain from 1 to 4 hetero atoms selected from nitrogen, oxygen and sulfur, it being possible for that heterocyclic ring system in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, hydroxy-d-dalkyl, C C4alkoxy, d-dalkoxy-Crdalkyl, -CN, -NO2, C dalkylthio, d-dalkylsulfinyl or by d-daikylsulfonyl; or each R2 independently is C2-C8alkenyl, or is C2-C8alkenyl mono-, di- or tri-substituted by - CN, -NO2, -CO2R94, -CONR95R96, -COR97, -C(R98)=NOR99, -C(S)NR100Rιoι, -C(C C4alkyl- thio)=NR102, -ORios, -Si(R104)3 or by C3-C6cycloalkyl; or each R2 independently is C2-C8alkynyl, or is C2-C8alkynyl mono-, di- or tri-substituted by halogen, -CN, -CO2Rι0S, -CONR106Rιo7, -COR108> -C(R109)=NOR110, -C(S)NR111R112, -C(CrC4alkylthio)=NR113, -OR114, -Si(Rn5)3 or by C3-C6cycloalkyl; or each R2 independently is C3-C6cycloalkyl, or is C3-C6cycloaikyl mono-, di- or tri-substituted by halogen, -CN, -CO2Rn6, -CONR117Rι18, -CORng, -C(R120)=NOR121, -C(S)NR122R123 or by
-C(CrC alkylthio)=NR124; or two adjacent R2 substituents together form a d-C7alkylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted by halogen, d-dalkyl or by d-dalkoxy, the total number of ring atoms being at least 5 and at most 9; or two adjacent R2 substituents together form a C2-dalkenylene bridge which may be interrupted by from 1 to 3 hetero atoms selected from oxygen, nitrogen and sulfur and may be mono-, di- or tri-substituted by halogen, d-dalkyl or by d-dalkoxy, the total number of ring atoms being at least 5 and at most 9;
R71 is hydrogen or d-dalkyl;
R72 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, Crdalkylsulfinyl or by C dalkylsulfonyl; or
R7ι and R72 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R73 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl, C3-C8alkenyl or
C3-C8alkynyl mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, Crdalkyl, Crd- haloalkyl, d-dalkoxy, -CN, -NO2, Crdalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
R74 is hydrogen or Crdalkyl;
R75 is hydrogen, d-dalkyl or C3-C7cycloalkyl, or is d-dalkyl mono-, di- or tri-substituted by
-COOH, d-dalkoxycarbonyl, d-dalkoxy or by -CN; or
R75 is d-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
R74 and R75 together are a C2-C5alkylene chain which may be interrupted by an oxygen or sulfur atom;
R76 is hydrogen, d-dalkyl, C C haloalkyl or C3-C6cycloalkyl;
R77 is hydrogen, d-dalkyl, CrC4haloalkyl or C3-C6cycloalkyl;
R78 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl; and
R79 is hydrogen or d-dalkyl; R80 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R80 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-C4haloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R79 and R80 together are C2-C5alkylene; R81 is hydrogen or d-dalkyl;
R82 is -Si(CrC6alkyI)3, C3-C8alkenyl or C3-C8alkynyl, or is Crdalkyl which is mono-, di- or tri- substituted by halogen, -CN, -NH2, d-dalkylamino, di(d-C6alkyi)amino or by C C alkoxy; R83 is hydrogen, d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, or is d-dalkyl which is mono-, di- or tri-substituted by halogen, -CN, -NH2, d-dalkylamino, di(CrC6alkyl)amino or by d-dalkoxy;
R84, R-35 and R86 are each independently of the others d-dalkyl, C3-C8alkenyl or C3-C8- alkynyl, or -dalkyl which is mono-, di- or tri-substituted by halogen, -CN or by d-dalkoxy;
R87 and R89 are each independently of the other hydrogen, d-C8alkyl or d-dalkoxy; R88 is d-dalkyl; R90 is hydrogen or d-dalkyl; R91 is d-dalkyl;
R92 and R93 are each independently of the other d-dalkyl;
R94 is hydrogen, or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono-, di- or tri-substituted by halogen, d-dalkoxy or by phenyl, it being possible for phenyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, - CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; R95 is hydrogen or d-dalkyl;
R96 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
Rg6 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or R95 and Rg6 together are C2-C5alkylene;
R97 and R98 are each independently of the other hydrogen, d-dalkyl, C C haloalkyl or Cg-dcycloalkyl;
R9g is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyi or C3-C6haloalkenyl; R100 is hydrogen or d-dalkyl; R10ι is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R10ι is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-C4alkylsulfonyl; or
R100 and R 0ι together are C2-C5alkylene;
R102 is hydrogen or d-dalkyl;
R103 is hydrogen, d-dalkyl, -Si(CrC6alkyl)3, C3-C8alkenyl or C3-C8alkynyl;
R104 is d-dalkyl;
R105 is hydrogen or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono-, di- or tri-substituted by halogen, C C alkoxy or by phenyl, it being possible for phenyl' in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy, -
CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl;
Rioe is hydrogen or d-dalkyl;
R107 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN, or
R107 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
R106 and R107 together are C2-C5alkylene;
R108 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl;
R10g is hydrogen, d-dalkyl, C C haloalkyl or C3-C6cycloalkyl;
R11o is hydrogen, Crdalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl;
Rm is hydrogen or d-dalkyl;
R112 is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R112 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
Rm and Rn2 together are C2-C5alkylene;
R113 is hydrogen or d-dalkyl;
R114 is hydrogen, d-dalkyl, -Si(d-C6alkyl)3, C3-C8alkenyl or C3-C8alkynyl;
R115 is d-dalkyl;
R116 is hydrogen or is d-dalkyl, C3-C8alkenyl or C3-C8alkynyl, each of which may be mono-, di- or tri-substituted by halogen, Cι-C alkoxy or by phenyl, it being possible for phenyl in tum to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, CrC alkoxy, -
CN, -NO2, d-dalkylthio, Crdalkylsulfinyl or by d-dalkylsulfonyl;
R117 is hydrogen or d-dalkyl;
RUB is hydrogen or d-dalkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R118 is d-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, d-dalkyl, d-dhaloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
Rι17 and Rn8 together are C2-dalkylene;
R119 is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl;
Rι2o is hydrogen, d-dalkyl, d-dhaloalkyl or C3-C6cycloalkyl;
R121 is hydrogen, d-dalkyl, C3-C8alkenyl, C3-C8alkynyl, d-dhaloalkyl or C3-C6haloalkenyl;
R122 is hydrogen or d-dalkyl;
Rι23 is hydrogen or CrC8alkyl, or is d-dalkyl mono-, di- or tri-substituted by -COOH, d-dalkoxycarbonyl or by -CN; or
R123 is C3-C8alkenyl, C3-C8alkynyl, phenyl or benzyl, it being possible for phenyl and benzyl in turn to be mono-, di- or tri-substituted by halogen, -dalkyl, d-dhaloalkyl, d-dalkoxy,
-CN, -NO2, d-dalkylthio, d-dalkylsulfinyl or by d-dalkylsulfonyl; or
R122 and R123 together are C2-C5alkylene; and
Ri24 is hydrogen or d-dalkyl.
3. A compound according to claim 2, wherein each Ri independently is halogen, -CN, -NO , -C(R10)=NORn, -OR13, -SO2Rι6, -OSO2R17, d-dalkyl or C2-C8alkenyl, or is CrC8alkyl mono- , di- or tri-substituted by halogen or by -CN; R10 is hydrogen or d-dalkyi; and Rn is d-dalkyl.
4. A compound according to claim 2, wherein Q is a group Q., Q2, Q3 or Q5.
5. A compound according to claim 4, wherein Q is a group Q, or Q2.
6. A compound according to claim 2, wherein each R independently is halogen, -CN, -SCN, -OCN, -N3, -CONR36R37, -C(R38)=NOR39, -COR4o, -OR41, -OSO2R45, -N([CO]pR46)COR47, -N(R56)SO2R57, -N(SO2R58)SO2R59J -N=C(OR6o)R6ι or Crdalkyl, or is d-dalkyl mono-, di- or tri-substituted by halogen, -CN, -N3, -SCN, -CONR74R75, -COR76, -C(R77)=NOR78, -C(S)NR79R80, -OR82, -SOR84, -SO2R85 or by -N(R89)COR90.
7. A process for the preparation of a compound of formula la
Figure imgf000098_0001
wherein Ri, R2, R3, R4, Z, m and n are as defined in claim 1, which process comprises reacting a compound of formula lla
Figure imgf000098_0002
wherein Ri and n are as defined in claim 1 (Q = Qi) and X is halogen, with a compound of formula Ilia
Figure imgf000098_0003
wherein R3 and R4 are as defined in claim 1 and M+ is an alkali metal cation, to form a compound of formula IVa
Figure imgf000098_0004
wherein Ri, R3, R4 and n are as defined in claim 1 , and then coupling that compound with a compound of formula V
Figure imgf000098_0005
wherein Z, R2 and m are as defined in claim 1 and A is a leaving group, in the presence of a palladium catalyst.
8. A herbicidal and plant-growth-inhibiting composition which comprises, on an inert carrier, a herbicidally effective amount of a compound of formula I.
9. 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 such a compound to the plants or to the locus thereof.
10. A method of inhibiting plant growth, which comprises applying a herbicidally effective amount of a compound of formula I or of a composition comprising such a compound to the plants or to the locus thereof.
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