WO2002024709A2 - Bicycloderivatives as herbicides - Google Patents

Bicycloderivatives as herbicides Download PDF

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Publication number
WO2002024709A2
WO2002024709A2 PCT/EP2001/010918 EP0110918W WO0224709A2 WO 2002024709 A2 WO2002024709 A2 WO 2002024709A2 EP 0110918 W EP0110918 W EP 0110918W WO 0224709 A2 WO0224709 A2 WO 0224709A2
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Prior art keywords
alkyl
alkoxy
phenyl
alkenyl
substituted
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PCT/EP2001/010918
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French (fr)
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WO2002024709A3 (en
Inventor
Kurt Nebel
Roger Graham Hall
Christoph Lüthy
Jean Wenger
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Syngenta Participations Ag
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Priority to AU2002221613A priority Critical patent/AU2002221613A1/en
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Publication of WO2002024709A3 publication Critical patent/WO2002024709A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
    • C07D273/06—Seven-membered rings

Definitions

  • the present invention relates to novel, herbicidally active oxa- and thia-diaza-bicyclic compounds, to processes for the preparation thereof, to compositions comprising those compounds, and to the use thereof in the control of weeds, especially in crops of useful plants, or in the inhibition of plant growth.
  • 9-Thia-1 ,7-diazabicyclodecanones having herbicidal activity are described, for example, in
  • herbicidal active ingredients are benzoxa(thia-)zol-4-yl-1 ,6,8-triaza- bicyclo[4.3.0]2-nonen-9-one-7-thiones in WO 00/13508 and 2-phenyl-hexahydro-3-thioxo-
  • WO 99/52893 and WO 99/55693 disclose 10-(6-pyridonylimino)- and 10-(2- pyridylimino)-9-thia-4-oxo-1 ,7-diaza-bicyclo[5.3.0]decan-8-one derivatives as herbicidal active ingredients.
  • the present invention accordingly relates to compounds of formula I
  • Ro is C C 4 alkyl; n 0 is 0 or from 1 to 8;
  • X is oxygen or sulfur; and Q is a group QI (Q1 )
  • Rr is hydrogen, fluorine, chlorine, bromine or methyl
  • R 2 is hydrogen, CrC 4 alkyl, d-C 4 haloalkyl, halogen, R 6 O-, nitro, amino, cyano, H 2 NC(O)-, H 2 NC(S)-, HOC(O)-, HC(O)- or R 9 S(O) n1 ;
  • R 6 is hydrogen, CrC 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 18 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloaIkenyl, CrC 8 haloalkyl, cyano-C ⁇ -C 8 alkyl, C 3 -C 8 haloalkenyl, C 3 -C 6 cycloalkyl-CrC alkyl, C 3 -C 6 halo- cycloalkyl-d-C 4 aIkyI, C 3 -C 6 cycloalkyl-C 2 -C 4 alkenyl, hydroxy-d-C 8 aIkyI, d-C 4 alkoxy-d-C 8 - alkyl, C 3 -C 6 alkenyloxy-CrC 8 alkyl, C 3 -C 6 alkynyloxy-C ⁇ -C 8 alkyI, d-C 4 aIk
  • R 6 is d-C 8 alkyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, or C 2 -C 8 alkenyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, it being possible for those phenyl, heteroaryl and heterocyclyl radicals to be mono- or poly-substituted by halogen, C C 4 alkyI, d-C 4 alkoxy, C C haloalkyl, d-C 4 haloalkoxy, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkenyl, C 2 -C 4 - haloalkynyl, C 3 -C 6 cycloalkyl, C C 4 alkyIthio, C C 4 alkylsuIfinyl, d-
  • X v ! • is oxygen, sulfur, R 8 a ⁇ N ⁇ ⁇ or F 8 O - N ⁇ — ;
  • R 7 is hydrogen, C C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 cycloalkyI, C r C 8 haloalkyl,
  • R 8 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 cycloalkyl, d-C 8 haloalkyl or benzyl;
  • R 9 is d-C ⁇ 8 alkyl, C 3 -C 18 alkenyl, C 3 -C 18 alkynyl, C 3 -C 6 cycloalkyl, C C 8 haloaIkyl, C 3 -C 8 cyclo- aIkyl-d-C alkyl, C 3 -Cehalocycloalkyl-C C 4 aIkyl, C 3 -C 8 cycloalkenyl, C 3 -C 6 cycIoalkyl-C 2 -C 4 - alkenyl, C 3 -C 8 haloalkenyl, d-C alkoxy-d-C alkyl, C 3 -C 6 alkenyloxy-d-C 4 alkyl, di(C 1 -C 3 - aIkoxy)d-C alkyl, d-C 4 alkylthio-d-C 4 alkyl, phenyl, phenyl mono- to tri-
  • R 9 is C C 8 alkyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, or C 2 -C 8 alkenyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, it being possible for those phenyl, heteroaryl and heterocyclyl radicals to be mono- or poly-substituted by halogen, d-C 4 alkyl, d-C 4 alkoxy, d-C 4 haloalkyl, C ⁇ -C 4 haloalkoxy, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkenyl, C 2 -C 4 halo- alkynyl, C 3 -C 6 cycloalkyl, d-C aIkylthio, d-C 4 alkylsulf
  • R 9 is R 10 X 2 C(O)-d-C 8 alkyl or R 10 X 2 C(O)-C 2 -C 8 alkenyl; and, when n 1 is 0,
  • R 9 is, in addition, hydrogen, d-C 8 alkylcarbonyl or R 10 X 2 C(O)-; v . ,, R ⁇ TN — R..O- N —
  • X 2 is oxygen, sulfur, 11 ⁇ or 11 ⁇ ;
  • R 10 is hydrogen, d-C 8 aIkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 cycloalkyl, CrC 8 haloalkyl, C 3 -C 8 haloalkenyl, d-C 4 alkoxy-C C 4 alkyl, C 3 -C 6 alkenyloxy-d-C 4 alkyl, C C alkylthio-C ⁇ -C 4 - alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C 4 alkyl or by C C 4 haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, d-C 4 alky ' l or by d-C 4 haloalkyl; and R
  • R 3 is hydrogen, halogen, nitro, amino, R 4 NH-, R 4 R 5 N-, R 6 O-, azido, cyano or CIS(O) 2 -;
  • R 4 and R 5 are each independently of the other C C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl,
  • R 4 and R 5 together with the nitrogen atom to which they are bonded form a saturated or unsaturated heterocyclic ring which contains as further hetero atoms oxygen, nitrogen and/or sulfur and which may be substituted by halogen, d-C 3 alkyl, d-C 3 haloalkyl, d-C 3 alkoxy, d-C 4 aIkoxycarbonyl, CrC 3 alkyl-S(O) n1 -, nitro or by cyano; or
  • R 3 is R 9 S(O) n1 - or R 12 R 13 NS(O) 2 -;
  • R 12 is hydrogen, d-C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 alkynyl or C 3 -C 6 cycloalkyl;
  • R 13 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, CrC 8 haloalkyl, d-C 4 alkoxy-d-C 4 - alkyl, C C aIkylcarbonyl, C C 4 haloalkylcarbonyl, benzyl, benzoyl, or benzyl or benzoyl mono- to tri-substituted on the phenyl ring by halogen, C C 4 alkyl or by d-C ha!oalkyl; or
  • R 3 is R 14 C(O)- or R 15 X 3 C(O)-;
  • R 14 is hydrogen, fluorine, chlorine, d-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 6 cycloalkyl,
  • C C 8 haloalkyl C 2 -C 8 haloalkenyl, d-C 4 alkoxy-d-C 4 alkyl, C 3 -C 6 alkenyloxy-CrC 4 alkyl, d-dalkylthio-d-dalkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C 4 alkyl or by
  • X 3 is oxygen, sulfur, 11 ⁇ or 1 ⁇ ;
  • R 15 is hydrogen, d-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 6 cycloalkyl, C C 8 haIoalkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 haloalkynyl, d-dalkoxy-d-dalkyl, C 3 -Cealkenyloxy-d-C 4 alkyl, C ⁇ -C alkylthio-C ⁇ -C 4 alkyl, d-Cealkoxycarbonyl-d-C e alkyl, C 2 -C 6 alkenyloxycarbonyl-d-C 6 - alkyl, C 2 -C 6 alkynyloxycarbonyl-CrC6aIkyl, CrC 6 alkylthio-C(O)-C 1 -C 6 alkyl, C 2 -C 6 alkenylthio- C(O
  • R 3 is B d-C ⁇ al yl, BrQrdalkenyl, B C 2 -C 8 alkynyl, B Cs-dcycloalkyl, B d-C 8 haloalkyl, B ⁇ -C 2 -C 8 haloalkenyl, Brd-dalkoxy-Crdalkyl or B 1 -C 1 -C 4 alkylthio-C 1 -C 4 alkyl; Br is hydrogen, cyano, hydroxy, d-C 8 alkoxy, C 3 -C 8 alkenyloxy, R 7 X 3 C(O)-, d- C 4 alkylcarbonyl or C ⁇ -C 4 haloalkylcarbonyl; or
  • B 2 is nitro, cyano or R 7 X 3 C(O)-;
  • R 16 is hydrogen, halogen, cyano or R 7 X 3 C(O)-; or
  • Q is a group Q2 or Q3
  • R 1 is as defined hereinbefore;
  • R 17 and R 18 are each independently of the other hydrogen, fluorine, chlorine, bromine, hydroxy, mercapto, amino, cyano, nitro, C C 8 alkyI, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 6 cyclo- alkyl, d-C 8 haloalkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 haloalkynyl, d-dalkoxy-d-dalkyl, C 3 -C 6 - alkenyloxy-C C 4 alkyl, d-C 4 alkylthio-C ⁇ -C 4 alkyl, phenyl, phenyl mono- to tri-substituted by halogen, C C 4 alkyl, d-C 4 alkoxy, CrC 4 haloalkyl or by C C haloalkoxy, benzyl, or benzyl mono- to tri
  • R 19 is hydrogen, C C 12 aIkyl, d-C 12 haloalkyl, C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, C 2 -C 8 alkynyl- C 2 -C 4 alkenyl, C 3 -C 12 allenyl, C 2 -C 12 haloalkenyl, C 2 -C 12 haloalkynyl, C 3 -C 6 cycloalkyl, C 3 - C 6 cycloalkyl-C C 4 alkyl, C 3 -C 6 halocycloalkyl-C 1 -C 4 alkylJri(C 1 -C aIkyl)silyl-C 1 -C alkyl, tri(d- C 4 alkyl)silyl-C 2 -C 4 alkenyl, cyano-C C 12 alkyl, d-Cealkoxy-d-dalkyl, d-C 4 al
  • Q is a group Q4 (04),
  • R- ! , R 2 , B and D are as defined hereinbefore; or
  • Q is a group Q5 (05)
  • R ⁇ , R 2 , A, B and D are as defined hereinbefore, and also the agronomically acceptable salts and stereoisomers of such compounds of formula I.
  • 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 various isomeric pentyl, hexyl, heptyl and octyl radicals. Preference is given to methyl, ethyl, n-propyl, isopropyl and n-butyl.
  • Alkenyl, alkynyl and allenyl groups may likewise be straight-chained or branched, that also being true of the alkyl, alkenyl and alkynyl moiety of hydroxyalkyl, cyanoalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonyl, alkenyloxycarbonyl-alkyl, alkenyloxy-alkyl, alkynyloxy- alkyl, alkynyl-alkenyl, alkylthio-alkyl, alkylthio-C(O)-alkyl, alkyl-S(O) n r, alkylthioalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylamino, dialkylamino, alkylaminocarbonyl-alkyl, dialkylaminocarbonyl-alkyl, phenylalkyl, B-i-alkyl, B al
  • alkenyl radicals vinyl, allyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pentenyl, 2-hexenyl, 3-heptenyl and 4-octenyl, preferably alkenyl radicals having a chain length of from 3 to 5 carbon atoms.
  • alkynyl radicals propargyl, 1 -methylpropargyl, 3- butynyl, but-2-yn-1 -yl, 2-methylbutyn-2-yl, but-3-yn-2-yl, 1-pentynyl, pent-4-yn-1 -yl, 2- hexynyl, 3-heptyn-1-yl and 4-octyn-1-yl, preferably alkynyl radicals having a chain length of 3 or 4 carbon atoms.
  • halogen is to be understood as being iodine, preferably fluorine, chlorine and bromine.
  • Alkoxy radicals preferably have a chain length of from 1 to 8 carbon atoms.
  • Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert- butoxy, or a pentyloxy, hexyloxy, heptyloxy or octyloxy isomer, preferably methoxy and ethoxy.
  • Alkenyloxy is, for example, allyloxy, methallyloxy and but-2-en-1 -yloxy.
  • Alkynyloxy is, for example, propargyloxy and 1 -methylpropargyloxy.
  • Suitable haloalkyl radicals include alkyl groups substituted one or more times, especially one to three times, by halogen, halogen being in particular iodine and especially fluorine, chlorine or bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloro- methyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2- trifluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl.
  • Suitable haloalkenyl radicals include alkenyl groups substituted one or more times by halogen, halogen being in particular bromine or iodine and especially fluorine or chlorine, for example 2- and 3-fluoropropenyI, 2- and 3-chloropropenyl, 2- and 3-bromopropenyl, 2,3,3- trifluoropropenyl, 2,3,3-trichloropropenyl, 4,4,4-trif luorobut-2-en-1 -yl and 4,4,4-trichlorobut-2- en-1 -yl.
  • alkenyl radicals substituted once, twice or three times by halogen preference is given to those having a chain length of 3 or 4 carbon atoms.
  • the alkenyl groups may be substituted by halogen at saturated or unsaturated carbon atoms.
  • Suitable haloalkynyl radicals include, for example, alkynyl groups substituted one or more times by halogen, halogen being bromine or iodine and especially fluorine or chlorine, for example 3-fluoropropynyI, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4,4,4-trifluoro-but-2-yn-1-yl.
  • alkynyl radicals substituted one or more times by halogen preference is given to those having a chain length of from 3 to 5 carbon atoms.
  • Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, 1 ,1 ,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2,2- trichloroethoxy.
  • Suitable haloalkenyloxy radicals include alkenyloxy groups substituted one or more times by halogen, halogen being in particular bromine or iodine and especially fluorine or chlorine, for example 2- and 3-fluoropropenyloxy, 2- and 3-chloropropenyloxy, 2- and 3-bromopropenyl- oxy, 2,3,3-trif luoropropenyloxy, 2,3,3-trichloropropenyloxy, 4,4,4-trif luoro-but-2-en-1 -yloxy and 4,4,4-trichloro-but-2-en-1 -yloxy.
  • Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, preferably methylsulfonyl and ethylsulfonyl.
  • Haloalkylsulfonyl is, for example, fluoromethylsulfonyi, difluoromethylsulfonyl, trifluoromethyl- sulfonyl, chloromethylsulfonyl, trichloromethylsulfonyl, 2-fluoroethylsulfonyl, 2,2,2-trifluoro- ethylsulfonyl and 2,2,2-trichloroethylsulfonyl.
  • Alkylcarbonyl is especially acetyl and propionyl.
  • Haloalkylcarbonyl is especially trifluoroacetyl, trichloroacetyl, 3,3,3-trifluoropropionyl and 3,3,3-trichloropropionyl.
  • Cyanoalkyl is, for example, cyanomethyl, cyanoethyl, cyanoeth-1-yl and cyanopropyl.
  • Hydroxyalkyl is, for example, 2-hydroxyethyl, 3-hydroxypropyl and 2,3-dihydroxypropyl.
  • Alkoxy-alkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n- propoxymethyl, n-propoxyethyl, isopropoxymethyl and isopropoxyethyl.
  • Alkenyloxy-alkyl is, for example, allyloxy-alkyl, methallyloxy-alkyl and but-2-en-1 -yloxy-alkyl.
  • Alkynyloxy-alkyl is, for example, propargyloxy-methyl and 1 -methylpropargyloxy-methyl.
  • Haloalkynyloxy-alkyl is, for example, 3-chloropropynyloxy-methyl and 3-fluoropropynyloxy- methyl.
  • Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and n-butoxycarbonyl, preferably methoxycarbonyl and ethoxycarbonyl.
  • Alkenyloxycarbonyl is, for example, allyloxycarbonyl, methallyloxycarbonyl, but-2-en-1 -yl- oxycarbonyl, pentenyloxycarbonyl and 2-hexenyloxycarbonyl.
  • cycloalkyl radicals suitable as substituents are, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Cycloalkyl-alkyl and halocycloalkyl-alkyl are, for example, cyclopropylmethyl, dimethyl- cyclopropylmethyl, difluorocyclopropylmethyl, dichlorocyclopropylmethyl, dibromocyclo- propylmethyl, 2,2,3,3-tetrafluorocyclobutylmethyl and 2,2-difluoro-3,3-dichlorocyclobutyl- methyl.
  • the cycloalkyl-containing groups may also be substituted one or more times by further d-C 3 alkyl groups, especially methyl groups, and by halogen and d-C 3 haIoalkyl.
  • cycloalkylcarbonyl radicals suitable as substituents are, for example, cyclopropyl- carbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl and cyclohexylcarbonyl.
  • Alkylthio is, for example, methylthio, ethylthio, propylthio and isopropylthio.
  • Alkylthioalkyl is, for example, methylthioethyl, ethylthioethyl, methylthiopropyl and ethylthiopropyl.
  • Phenyl or benzyl as part of a substituent for example phenylalkyl, phenylalkenyl, benzyloxy, benzyloxyalkyl, benzylcarbonyl, benzyloxycarbonyl or benzyloxycarbonylalkyl, may be in substituted form, in which case the substituents may be in the ortho-, meta- and/or para- position(s).
  • Substituents are, for example, C ⁇ -C 4 alkyl, halogen and C C 4 haloalkyl.
  • heterocycles it being possible for those heterocycles to be, in addition, substituted by halogen, d-C 3 alkyl, d-C 3 haloalkyl, d-C 3 aIkoxy, C C alkoxycarbonyl, d-C 3 alkyl-S(O) n ⁇ -, nitro or by cyano.
  • a heterocyclyl group (for example in the definitions of R 6 , Rg and R 19 ) may be aromatic, that is to say have the meaning of heteroaryl, e.g. pyridyl, pyrimidyl, pyrazinyl and pyridazinyl, and also partially or completely saturated and may contain from 1 to 4 nitrogen atoms and/or 1 or 2 oxygen atoms and/or 1 or 2 sulfur atoms.
  • Examples that may be mentioned include the 2- and 3-pyridyl groups, the 2- and 4-pyrimidyl groups, the 1 - and 3-pyrazolyl groups, the 1- and 2-furyl groups, the 1- and 2-thienyl groups, the 2-oxazolyl group, the 1 -oxadiazolyl group, the 1 ,2-oxazol-3-yl group, the 1 ,2-oxazolin-3-yl group, the 1- and 3-triazolyl group, the oxiran-2-yl group, the oxetan-3-yl group, the tetrahydrofur-2-yl group, the tetrahydropyran-2- yl group, the 1 ,3-dioxazolin-2-yl group, the .1 ,3-dioxolan-2-yl group, the ethylenedi ⁇ xy-2-yl group, the propylenedioxy-2-yl group, the 1 ,3-oxathiazol-2-
  • substituted d-C 8 alkylene chain is, in addition, substituted by phenyl at one of the 8 carbon atoms, it being possible for the phenyl ring to be mono- to tri-substituted by halogen, C 1 -C 4 - alkyl or by C C 4 haloalkyI and for the alkylene chain to be straight-chained or branched, for example methylene, ethylene, methylethylene, propylene, 1 -methyl-propylene and butylene.
  • Typical ring systems for the groups Q2, Q3 and Q4 are, for example:
  • Q2(i) e.g. Q2(i) ; for Q3, e.g. Q3(i), Q3(ii), Q3(iii),
  • Q4(i), Q4(ii), Q4(iii), Q4(iv), Q4(v) and Q4(vi) Q4(i», (Q4( ⁇ )), (Q4(iii)
  • cyanoalkyl carboxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxy- carbonyl, alkenylcarbonyl, alkynylcarbonyl, alkynyloxycarbonyl-alkyl, haloalkylcarbonyl-alkyl, cycloalkylcarbonyl-alkyl and haloalkylcarbonyl
  • the upper and lower limits of the number of carbon atoms given in each case do not include the carbon atom of the cyano, carboxy or carbonyl.
  • the invention also includes the salts that the compounds of formula I may form especially with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
  • Suitable salt formers are described, for example, in WO 99/52892 and WO 97/41112.
  • the invention also includes the salts that the compounds of formula I may form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
  • alkali metal and alkaline earth metal hydroxides used as salt formers emphasis is to be given to the hydroxides of lithium, sodium, potassium, magnesium and calcium, but especially to those of sodium and potassium.
  • amines suitable for ammonium salt formation are ammonia as well as primary, secondary and tertiary C ⁇ -C ⁇ 8 alkylamines, d-C 4 hydroxyalkyl- amines and C 2 -C 4 alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, 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-oc
  • Preferred quaternary ammonium bases that are suitable for salt formation correspond, for example, to the formula [N(R a R b R c R d )]OH, wherein R a , R b , R c and R d are each independently of the others C ⁇ -C 4 alkyl.
  • Other suitable tetraalkylammonium bases having different anions can be obtained, for example, by anion exchange reactions.
  • salts of compounds of formula I having acid hydrogen especially the derivatives having carboxylic acid groups (e.g. carboxyl-substituted alkyl and alkylene groups (R 6 ))
  • salts of compounds of formula I having basic groups especially having basic pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl and imidazolyl rings (group Q3(ii)) or having amino groups, for example alkylamino and dialkylamino groups in the definition of R 2 or R 3 .
  • Such salts are, for example, salts with inorganic or organic acids, e.g.
  • hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid, and sulfuric acid, phosphoric acid, nitric acid, and organic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, citric acid, benzoic acid, oxalic acid, formic acid, benzenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid.
  • alkyl alkenyl, alkynyl, haloalkyl or alkoxyalkyl group, or A, B, D or E is P(R 17 )R 18 >
  • X is oxygen or sulfur
  • Q is a group Q1 (Q1 ),
  • R 2 is hydrogen, d-C 4 alkyl, C 1 -C 4 haloalkyl, halogen, R 6 O-, nitro, amino, cyano, H 2 NC(O)-,
  • R 3 is halogen, nitro, amino, R 4 NH-, R 4 R 5 N-, R 6 O-, azido, cyano or CIS(O) 2 -;
  • R 4 and R 5 are each independently of the other C C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 - cycloalkyl, d-C 8 haloalkyl, C 3 -C 8 haloalkenyl, HC(O)-, d-C 4 alkylcarbonyI, C C 4 haloalkyl- carbonyl, d-C 4 alkylsulfonyl, C C 4 haloaIkyIsulfonyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, C ⁇ -C alkyl or by C C 4 haloalkyl; or R 4 and R 5 together with the nitrogen atom to which they are bonded form a saturated or unsaturated heterocyclic ring which contains as further hetero atoms oxygen, nitrogen or sulfur and which may be substituted by halogen,
  • R 6 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 cycIoalkyl, C C 8 haloalkyl, cyano-C C 8 alkyl, C 3 -C 8 haloalkenyl, hydroxy-d-C 4 alkyl, C ⁇ -C 4 alkoxy-d-C 4 alkyl, C 3 -C 6 - aIkenyloxy-d-C 4 alkyl, C 3 -C 6 alkynyloxy-C C 4 alkyl, d-dalkoxy-d-dalkoxy-d-dalkyl, d-C 4 alkylthio-d-C alkyl, d-C 8 alkylcarbonyl, C C 8 alkoxycarbonyl, C 3 -C 8 alkenyloxycarbonyl, benzyloxy-C or -C 2 -alkyI
  • R 6 is R 7 X 1 C(O)-C 1 -C 8 alkyl- or
  • R 7 is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 cycloalkyl, d-C 8 haloalkyl, C 3 -C 8 haloalkenyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, drCealkenyloxy-d-dalkyl, C 1 -C 4 alkylthio-C 1 -C 4 - alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C 4 a!kyl or by C 1 -C 4 haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, C C 4 alkyl or by d-C 4 haloalkyl; or
  • R 3 is R 9 S(O) n1 -; n! is 0, 1 or 2; and
  • R 9 is d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 cycloalkyl, d-C 8 haloalkyl, carboxy-d-C 4 - alkyl, d-C 4 alkoxycarbonyl-C ⁇ -C 4 alkyl, benzyloxycarbonyl-d-C 4 alkyl, C 1 -C 4 alkylthio-C(O)- C C 4 alkyl, C 3 -C 5 alkenyloxycarbonyl-C 1 -C 4 alkyl, d-C 4 alkylaminocarbonyl-C ⁇ -C 4 alkyl, di(C 1 -C 4 -alkyl)aminocarbonyl-C 1 -C 4 alkyl, drCsalkenylaminocarbonyl-d-dalkyl, C 3 -C 8 halo- alkenyl, d-
  • R 9 is in addition hydrogen, C C 8 alkylcarbonyl, R 10 X 2 C(O)- or R 10 X 2 C(O)-C ⁇ - or -C 2 -alkyl; or
  • Q is a group Q2 or Q3
  • R 19 is hydrogen, d-C 12 alkyl, d-C ⁇ 2 haloalkyl, C 2 -C ⁇ 2 alkenyl, C 2 -C 12 alkynyl, C 2 -C 8 alkynyl- C 2 -C 4 alkenyl, C 3 -C 12 allenyl, C 2 -C 12 haloalkenyl, C 2 -d 2 haloalkynyl, C 3 -C 6 cycIoalkyl, C 3 -C 6 - cycloalkyl-d-C 4 alkyl, C 3 -C 6 halocycloalkyl-d-C 4 alkyl, tri(C 1 -C 4 alkyl)silyl-C 1 -C 4 alkyl, tri(d-C 4 - alkyl)silyI-C 2 -C 4 alkenyl, cyano-d-C 12 alkyl, d-C 6 alkoxy-d-C 4 al
  • R ⁇ 9 is phenyl-substituted C 2 -C 4 alkeny
  • Q is a group Q4 (Q4) or Q5
  • R 0 , n 0 , R ⁇ X,, X 2 , R ⁇ , Rio, R12, R13, i4, R15, 3, Bi, B 2 , R 16 , R17, Ri ⁇ , n and G are as defined for formula I, and A, B, D and R 2 are as defined above.
  • R ⁇ is hydrogen, fluorine or chlorine. Of those compounds, special preference is given to those wherein R* is fluorine. Preference is also given to compounds of formula I wherein Q is a group Q1 , and R is halogen. Of those compounds, special preference is given to those wherein R 2 is chlorine.
  • the compounds of formula I can be prepared using processes known perse, for example described in WO 99/55693, for example by converting an isothiocyanate of formula II
  • R 0 and n 0 are as defined for formula I and Hal is halogen, especially chlorine, bromine or iodine, in an inert organic solvent, for example an ether, e.g. tetrahydrofuran (THF), at temperatures of from -10° to 30°C, preferably from 0° to 20°C, into the compound of formula IV treating that compound, in accordance with variant a), advantageously in a suitable solvent, for example an aromatic hydrocarbon, e.g. toluene or an isomer of xylene, or an ether, e.g. tetrahydrofuran, with a (thio-)carbonylating agent, e.g. (thio-)phosgene of formula Ma
  • an inert organic solvent for example an ether, e.g. tetrahydrofuran (THF)
  • THF tetrahydrofuran
  • a suitable solvent for example an aromatic hydrocarbon, e.g. tol
  • an inert organic solvent for example an aromatic hydrocarbon, e.g. toluene or an isomer of xylene, with imidazole, with gentle heating at temperatures of from 40° to 80°C, preferably from 50° to 70°C, or treating the compound of formula IV, in accordance with variant b), advantageously in a suitable solvent, for example an aromatic hydrocarbon, e.g. toluene or an isomer of xylene, or an ether, e.g. tetrahydrofuran, with a (thio-)carbonylating agent, e.g. (thio-)phosgene of formula lla
  • an aromatic hydrocarbon e.g. toluene or an isomer of xylene
  • imidazole with gentle heating at temperatures of from 40° to 80°C, preferably from 50° to 70°C
  • a suitable solvent for example an aromatic hydrocarbon, e.g. toluene or an isomer of x
  • solvent e.g. a xylene, 60°C
  • Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, 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, diethylformamide or N-methylpyrrolidinone.
  • the reaction temperatures are preferably between -20°C and +120°C.
  • the reactions are slightly exothermic and, as a rule, they can be carried out at room temperature.
  • the mixture may be heated briefly to the boiling point of the reaction mixture.
  • the reaction times can also be shortened 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-diazabicyclo[4.3.0]non-5-ene or 1 ,5-diazabicyclo- [5.4.0]undec-7-ene.
  • inorganic bases such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate, may also be used as bases.
  • hydrides e.g. sodium hydride or calcium hydride
  • hydroxides e.g. sodium hydroxide or potassium hydroxide
  • carbonates such as sodium carbonate and potassium carbonate
  • hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate
  • the compounds of formula I can be isolated in customary manner by concentrating and/or by evaporating the solvent and purified by recrystallisation or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
  • the compounds of formula I can be used as herbicides in unmodified form, that is to say as they are obtained in 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, in WO 97/34485 on pages 9 to 13.
  • 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 of formula I or at least one compound of formula I and, generally, one or more solid or liquid formulation adjuvants
  • formulation adjuvants for example solvents or solid carriers.
  • surface-active compounds surfactants
  • solvents and solid carriers are given, for example, in WO 97/34485 on page 6.
  • suitable surface- active compounds are non-ionic, cationic and/or anionic surfactants and mixtures of surfactants having good emulsifying, dispersing and wetting properties.
  • suitable anionic, non-ionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8.
  • the surfactants customarily employed in formulation technology which are described, inter alia, in " c Cutcheon's Detergents and Emulsifiers Annual” MC Publishing Corp., Ridgewood New Jersey, 1981 , Stache, H., "Tensid-Taschenbuch", Carl Hanser Verlag, Kunststoff/Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants", Vol l-lll, Chemical Publishing Co., New York, 1980-81 , are also suitable for preparation of the herbicidal compositions according to the invention.
  • the herbicidal formulations generally comprise 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 solid or liquid formulation adjuvant especially from 0 to 25 % by weight, especially from 0.1 to 25 % by weight, of a surfactant.
  • 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), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and tackifiers, as well as fertilisers or other active ingredients.
  • stabilisers for example vegetable oils or epoxidised vegetable oils (epoxidised coconut oil, rapeseed oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and tackifiers, as well as fertilisers or other active ingredients.
  • the compounds of formula I are generally applied to the plant or to 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
  • the compounds of formula I are distinguished by herbicidal and growth-inhibiting properties, allowing them to be used in crops of useful plants, especially in cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and also for non-selective weed control.
  • Crops are to be understood as including also crops that have been made tolerant to herbicides or classes of herbicides by means of conventional plant breeding or by genetic engineering methods.
  • the weeds to be controlled may be either monocotyledonous or dicotyledonous weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Panicum, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
  • Stellaria Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Panicum, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus,
  • the compounds of formula I according to the invention can also be used for weed control in admixture with known herbicides as co-herbicides, for example in the form of ready-prepared formulations or in the form of a 'tank-mix'.
  • suitable mixing partners for the compounds of formula I include, for example, the following co-herbicides:
  • the crude product obtained is chromatographed over silica gel (eluant: hexane/ethyl acetate 1/1) at 0.6 mbar and the product obtained is recrystallised from toluene/hexane.
  • the desired target compound no. .001 is obtained as a solid having a melting point of 142-144°C.
  • Test plants Setaria (Set), Panicum (Pan), Digitaria (Digi), Sida, Abutilon (Abu), Amaranthus (Ama).
  • test plants Monocotyledonous and dicotyledonous test plants are sown in standard soil in pots.
  • the test plants are sprayed with 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), in an optimum concentration (500 litres water/ha).
  • Test plants Setaria (Set), Panicum (Pan), Digitaria (Digi), Sida, Abutilon (Abu), Xanthium (Xan), Amaranthus (Ama), Chenopodium (Chen).

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Abstract

Compounds of formula (I), wherein R0 is C1-C4alkyl; n0 is 0 or from 1 to 8; X is oxygen or sulfur; and Q is a group Q1, Q2, Q3, Q4 or Q5, wherein R1 is hydrogen, fluorine, chlorine, bromine or methyl; R2 is hydrogen, C1-C4alkyl, C1-C4haloalkyl, halogen, R6O-, nitro, amino, cyano, H2NC(O)-, H2NC(S)-, HOC(O)-, HC(O)- or R9S(O)n1; and n1 is 0, 1 or 2, and the substituents R3, R6, R9, A, B, D, E and G are as defined in claim 1, are suitable for use as herbicides.

Description

Novel herbicides
The present invention relates to novel, herbicidally active oxa- and thia-diaza-bicyclic compounds, to processes for the preparation thereof, to compositions comprising those compounds, and to the use thereof in the control of weeds, especially in crops of useful plants, or in the inhibition of plant growth.
9-Thia-1 ,7-diazabicyclodecanones having herbicidal activity are described, for example, in
EP-A-0 705 267.
Also described as herbicidal active ingredients are benzoxa(thia-)zol-4-yl-1 ,6,8-triaza- bicyclo[4.3.0]2-nonen-9-one-7-thiones in WO 00/13508 and 2-phenyl-hexahydro-3-thioxo-
1 H-[1.2.4]triazolo[1 ,2-a]pyridazin-1-ones in US-A-6 121 201.
Furthermore, WO 99/52893 and WO 99/55693 disclose 10-(6-pyridonylimino)- and 10-(2- pyridylimino)-9-thia-4-oxo-1 ,7-diaza-bicyclo[5.3.0]decan-8-one derivatives as herbicidal active ingredients.
Novel oxa- and thia-diazabicyclic derivatives having herbicidal and growth-inhibiting properties have now been found.
The present invention accordingly relates to compounds of formula I
Figure imgf000002_0001
wherein
Ro is C C4alkyl; n0 is 0 or from 1 to 8;
X is oxygen or sulfur; and Q is a group QI (Q1 )
Figure imgf000003_0001
wherein
Rr is hydrogen, fluorine, chlorine, bromine or methyl;
R2 is hydrogen, CrC4alkyl, d-C4haloalkyl, halogen, R6O-, nitro, amino, cyano, H2NC(O)-, H2NC(S)-, HOC(O)-, HC(O)- or R9S(O)n1;
Figure imgf000003_0002
R6 is hydrogen, CrC18alkyl, C3-C18alkenyl, C3-C18alkynyl, C3-C6cycloalkyl, C3-C6cycloaIkenyl, CrC8haloalkyl, cyano-Cι-C8alkyl, C3-C8haloalkenyl, C3-C6cycloalkyl-CrC alkyl, C3-C6halo- cycloalkyl-d-C4aIkyI, C3-C6cycloalkyl-C2-C4alkenyl, hydroxy-d-C8aIkyI, d-C4alkoxy-d-C8- alkyl, C3-C6alkenyloxy-CrC8alkyl, C3-C6alkynyloxy-Cι-C8alkyI, d-C4aIkoxy-d-C4alkoxy- d-C4alkyl, di(C1-C3alkoxy)C1-C4alkyl, d- alkylthio-d-Csalkyl, C C8alkylsulfonyl, d-C8haloalkylsulfonyl, d-C8alkylcarbonyl, d-C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, benzyloxy-d-C4alkyl, phenylcarbonyl-C-i- or -C2-alkyl, benzylcarbonyl, benzyloxycarbonyl, phenyl or heteroaryl, it being possible for the afore-mentioned aromatic and heteroaromatic radicals to be mono- to tri-substituted by hydroxy, amino, nitro, cyano, CO2H, CONH2, CSNH2, halogen, HC(O)-, C C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C C4haloalkyl, C2-C4halo- alkenyl, C2-C4haloalkynyl, C C4alkoxy, C2-C4alkenyloxy, C2-C4alkynyloxy, C1-C4haloalkoxy, C2-C4haloalkenyloxy, C2-C4haloalkynyloxy, C1-C4haloalkylthio, CrC4haIoalkylsulfinyl, CrC haloalkylsulfonyl, CrC4aIkylcarbonyl, CrC4alkoxycarbonyl, d-C4aIkoxy-Cι-C alkoxy, Cι-C alkyl-C2-C4alkenyloxy, d-C alkoxycarbonyl-d-C alkoxy, d-C4haloalkoxycarbonyl- d-C alkoxy, C3- or C4-alkenyloxycarbonyl-d-C4alkoxy, C3- or C4-haloalkenyloxycarbonyl- d-C4alkoxy, C3- or C4-alkynyloxycarbonyl-C C4alkoxy, HOCCOJ-C C^lkoxy, d-C4alkyl- carbonyl-C C4alkoxy, HC(O)-C C4alkoxy, R8(R8)N-d-C4alkoxy or by R8(R8)NC(O)-C C4- alkoxy; or
R6 is d-C8alkyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, or C2-C8alkenyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, it being possible for those phenyl, heteroaryl and heterocyclyl radicals to be mono- or poly-substituted by halogen, C C4alkyI, d-C4alkoxy, C C haloalkyl, d-C4haloalkoxy, C2-C4alkenyl, C2-C4alkynyl, C2-C4haloalkenyl, C2-C4- haloalkynyl, C3-C6cycloalkyl, C C4alkyIthio, C C4alkylsuIfinyl, d-C4alkylsulfonyl, d-C4halo- alkylthio, CrC4haloalkylsulfinyl, d-C4haloalkylsulfonyl, cyano, CrC6alkoxycarbonyl, nitro, phenyl, phenoxy, heteroaryl or by heteroaryloxy; or R6 is R7X1C(O)-C1-C8alkyl-, R7X1C(O)-C2-C8alkenyl- or R-X.CCO) [C C8alkylene]-
(C6H5)
X v! • is oxygen, sulfur, R8 a~N ι ~ or F 8O - N ι — ;
R7 is hydrogen, C C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyI, CrC8haloalkyl,
C3-C8haloalkenyl, d-C4alkoxy-C C alkyl, d-Cealkenyloxy-d-dalkyl, CrC4alkylthio-d-C4- alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C4aikyl or by C C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, nitro, C C4alkyl or by d-C4haloalkyl;
R8 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, d-C8haloalkyl or benzyl; and
R9 is d-Cι8alkyl, C3-C18alkenyl, C3-C18alkynyl, C3-C6cycloalkyl, C C8haloaIkyl, C3-C8cyclo- aIkyl-d-C alkyl, C3-Cehalocycloalkyl-C C4aIkyl, C3-C8cycloalkenyl, C3-C6cycIoalkyl-C2-C4- alkenyl, C3-C8haloalkenyl, d-C alkoxy-d-C alkyl, C3-C6alkenyloxy-d-C4alkyl, di(C1-C3- aIkoxy)d-C alkyl, d-C4alkylthio-d-C4alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C4aIkyl or by d-C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, d-C4a!kyl or by d-C4haloalkyl, or
R9 is C C8alkyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, or C2-C8alkenyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, it being possible for those phenyl, heteroaryl and heterocyclyl radicals to be mono- or poly-substituted by halogen, d-C4alkyl, d-C4alkoxy, d-C4haloalkyl, Cι-C4haloalkoxy, C2-C4alkenyl, C2-C4alkynyl, C2-C4haloalkenyl, C2-C4halo- alkynyl, C3-C6cycloalkyl, d-C aIkylthio, d-C4alkylsulfinyl, Cι-C alkylsulfonyl, Cι-C4haloalkyl- thio, C C4haloalkylsulfinyl, Cι-C4haloalkylsulfonyl, cyano, d-C6alkoxycarbonyl, nitro, phenyl, phenoxy, heteroaryl or by heteroaryloxy; or
R9 is R10X2C(O)-d-C8alkyl or R10X2C(O)-C2-C8alkenyl; and, when n1 is 0,
R9 is, in addition, hydrogen, d-C8alkylcarbonyl or R10X2C(O)-; v . ,, R^TN — R..O- N —
X2 is oxygen, sulfur, 11 ι or 11 ι ; R10 is hydrogen, d-C8aIkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, CrC8haloalkyl, C3-C8haloalkenyl, d-C4alkoxy-C C4alkyl, C3-C6alkenyloxy-d-C4alkyl, C C alkylthio-Cι-C4- alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C4alkyl or by C C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, d-C4alky'l or by d-C4haloalkyl; and Rn is hydrogen, d-C8alkyl or C3-C8alkenyl;
R3 is hydrogen, halogen, nitro, amino, R4NH-, R4R5N-, R6O-, azido, cyano or CIS(O)2-;
R4 and R5 are each independently of the other C C8alkyl, C3-C8alkenyl, C3-C8alkynyl,
C3-C6cycloalkyl, C C8haloalkyl, C3-C8haloalkenyl, HC(O)-, C C4alkylcarbonyl, d-C4ha!o- alkylcarbonyl, d-C4alkylsulfonyl, d-C4haIoalkylsulfonyl, phenyl, benzyl, or phenyl or benzyl mono- to tri-substituted on the phenyl ring by halogen, Cι-C4alkyl, C C4haloalkyl or by d-C4alkoxy; or
R4 and R5 together with the nitrogen atom to which they are bonded form a saturated or unsaturated heterocyclic ring which contains as further hetero atoms oxygen, nitrogen and/or sulfur and which may be substituted by halogen, d-C3alkyl, d-C3haloalkyl, d-C3alkoxy, d-C4aIkoxycarbonyl, CrC3alkyl-S(O)n1-, nitro or by cyano; or
R3 is R9S(O)n1- or R12R13NS(O)2-;
R12 is hydrogen, d-C8alkyl, C2-C8alkenyl, C3-C8alkynyl or C3-C6cycloalkyl;
R13 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, CrC8haloalkyl, d-C4alkoxy-d-C4- alkyl, C C aIkylcarbonyl, C C4haloalkylcarbonyl, benzyl, benzoyl, or benzyl or benzoyl mono- to tri-substituted on the phenyl ring by halogen, C C4alkyl or by d-C ha!oalkyl; or
R3 is R14C(O)- or R15X3C(O)-;
R14 is hydrogen, fluorine, chlorine, d-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C6cycloalkyl,
C C8haloalkyl, C2-C8haloalkenyl, d-C4alkoxy-d-C4alkyl, C3-C6alkenyloxy-CrC4alkyl, d-dalkylthio-d-dalkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C4alkyl or by
Cι-C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, d-C4alkyl or by C C4haloalkyl; , • ,* Rl N— R..O - N —
X3 is oxygen, sulfur, 11 ι or 1 ι ;
R15 is hydrogen, d-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C6cycloalkyl, C C8haIoalkyl, C2-C8haloalkenyl, C2-C8haloalkynyl, d-dalkoxy-d-dalkyl, C3-Cealkenyloxy-d-C4alkyl, Cι-C alkylthio-Cι-C4alkyl, d-Cealkoxycarbonyl-d-Cealkyl, C2-C6alkenyloxycarbonyl-d-C6- alkyl, C2-C6alkynyloxycarbonyl-CrC6aIkyl, CrC6alkylthio-C(O)-C1-C6alkyl, C2-C6alkenylthio- C(O)-C C6alkyl, C2-C6alkynylthio-C(O)-C1-C6alkyl, C1-C6alkylamino-C(O)-C1-C6alkyl, C2-C6- alkenylamino-C(O)-d-C6alkyl, C2-C6alkynylamino-C(O)-d-C6alkyl, di(C1-C6alkyl)amino- C(O)-C C6alkyl, di(C2-C6alkeny))amino-C(O)-C1-C6alkyl, di(C2-C6alkynyl)amino-C(O)-d- C6alkyl, phenyl, phenyl mono- to tri-substituted by halogen, C C4alkyl or by Cι-C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, C C alkyI or by d- C4haloalkyl, phenyl-C2-C8alkyl, or phenyl-C2-C8alkyl mono- to tri-substituted on the phenyl ring by halogen, d-C4alkyl or by d-C4haloalkyl, phenyl-C2-C8alkenyl, or phenyl-C2-C8alkenyl mono- to tri-substituted on the phenyl ring by halogen, C C4alkyl or by C C haloalkyl, or d- C6alkyl-C(O)-d-C6alkyl; or
R3 is B d-Cβal yl, BrQrdalkenyl, B C2-C8alkynyl, B Cs-dcycloalkyl, B d-C8haloalkyl, Bι-C2-C8haloalkenyl, Brd-dalkoxy-Crdalkyl or B1-C1-C4alkylthio-C1-C4alkyl; Br is hydrogen, cyano, hydroxy, d-C8alkoxy, C3-C8alkenyloxy, R7X3C(O)-, d- C4alkylcarbonyl or Cι-C4haloalkylcarbonyl; or
R3 is B2-C(R16)=CH-;
B2 is nitro, cyano or R7X3C(O)-; and
R16 is hydrogen, halogen, cyano or R7X3C(O)-; or
Q is a group Q2 or Q3
Figure imgf000006_0001
wherein
A, B, D and E are each independently of the others =C(R17)-, -O-, =N-, -N(R19)-, -S(O)„-,
-C(O)-, -C(S)-, or
-C-NR 19 ■C( 17) «
R1 is as defined hereinbefore; and
R17 and R18 are each independently of the other hydrogen, fluorine, chlorine, bromine, hydroxy, mercapto, amino, cyano, nitro, C C8alkyI, C2-C8alkenyl, C2-C8alkynyl, C3-C6cyclo- alkyl, d-C8haloalkyl, C2-C8haloalkenyl, C2-C8haloalkynyl, d-dalkoxy-d-dalkyl, C3-C6- alkenyloxy-C C4alkyl, d-C4alkylthio-Cι-C4alkyl, phenyl, phenyl mono- to tri-substituted by halogen, C C4alkyl, d-C4alkoxy, CrC4haloalkyl or by C C haloalkoxy, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, d-C alkyI, Cι-C alkoxy, C C4halo- alkyl or by d-C4haloaIkoxy, phenyl-C2-C8alkyl, or phenyl-C2-C8a!kyl mono- to tri-substituted on the phenyl ring by halogen, d-C alkyl or by d-C4haloa]kyl, phenyl-C2-C8alkenyl, or phenyl-C2-C8alkenyl mono- to tri-substituted on the phenyl ring by halogen, d-C alkyl or by C C4haloalkyl, or d-Cealkyl-C^-d-Cealkyl;
R19 is hydrogen, C C12aIkyl, d-C12haloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C8alkynyl- C2-C4alkenyl, C3-C12allenyl, C2-C12haloalkenyl, C2-C12haloalkynyl, C3-C6cycloalkyl, C3- C6cycloalkyl-C C4alkyl, C3-C6halocycloalkyl-C1-C4alkylJri(C1-C aIkyl)silyl-C1-C alkyl, tri(d- C4alkyl)silyl-C2-C4alkenyl, cyano-C C12alkyl, d-Cealkoxy-d-dalkyl, d-C4alkoxy-d- or -C2- alkoxy-d- or -C2-alkyl, di(d-C4alkoxy)-d- or -C2-alkyl, ethylenedioxy-d- or -C2-alkyl, C2- C6alkenyloxy-d-C4alkyl, C2-C6haloalkenyloxy-d-C4alkyl, C2-C6alkynyloxy-d-C4alkyl, C3- C6haloaIkynyloxy-C C4alkyl, C Cealkylthio-d-C4alkyl, d-Cealkylsulfinyl-d-dalkyl, d- C6alkylsulfonyl-d-C4alkyl, hydroxy-d-C12alkyl, d-CealkyIcarbonyl-d-C4alkyl, d- C6haloalkylcarbonyl-CrC4alkyl, d-Cealkoxycarbonyl-d-dalkyl, d-Cealkoxy-d- or -C2- alkoxycarbonyl-C C4alkyl, CrCealkoxycarbonyl-d-C4haloaIkyl, C C4alkoxycarbonyl-C3- C6cycloalkyl, C3-C6cycloalkylcarbonyl-d-C4alkyl, or benzoyl-CrC4alkyl, it being possible for the benzoyl group to be substituted by halogen, d-C3alkyl, d-C3haloalkyl, C C3alkoxy or by d-C3haloalkoxy, C3-C6alkenyloxycarbonyl-C-ι-C alkyl, C3-C6alkynyloxycarbonyl-d-C alkyl, CrC8alkylcarbonyloxy-CrC4alkyl, C2-C6alkenylcarbonyloxy-d-C4alkyl, C3- C6cycloalkylcarbonyloxy-d-C alkyl, benzoyloxy-d-C4alkyl, d-C6alkoxycarbonyloxy-d- C4alkyl, carbamoyl-C C4alkyl, Cι-Cealkylaminocarbonyl-d-C4alkyl, or phenyl- or heterocyclyl-substituted C -C alkyl, it being possible for the phenyl and heterocyclyl groups to be substituted by halogen, C C6alkyl, d-C6alkoxy, C C6haloalkyl, Cι-C6haloalkoxy, d- C4alkylthio, d-C4alkylsulfinyl, d-C4alkylsulfonyI, d-C4haloalkylthio, d-C4haloalkylsulfinyl, CrC4haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3- C6cycloalkyl-d-C4alkyl, C3-C6halocycloalkyl-C C4alkyl, cyano-C C4alkyl, C Cealkoxy-d- C4alkyl, d-C6alkylthio-d-C4alkyl, CrC6alkylsulfinyl-CrC4alkyl, d-CealkylsuIfonyi-Crdalkyl, hydroxy-C C4alkyl, d-Cealkylcarbonyl-C^C^Ikyl, d-C6alkoxycarbonyl, C C6alkoxycarbonyl-Cι-C4alkyl, CrC6alkoxycarbonyl-d-C4haloalkyl, CrCealkoxycarbonyl-Cr C4alkoxy, C Cealkylcarbonyloxy-CrC^lkyl, d-Cealkoxycarbonyloxy-d-dalkyl, C
Figure imgf000007_0001
d-Cealkylaminocarbonyl-Cr C4alkoxy, phenyl, phenoxy or by benzyloxy, it being possible for the phenyl rings of the last three definitions to be in turn substituted by halogen, methyl, trifluoromethyl, methylsulfonyl, methoxy, ethoxy or by cyano; or phenyl-substituted C2-C4alkenyl or C2-C alkynyl, it being possible for the phenyl group to be substituted by halogen, methyl, trifluoromethyl, methylthio, methylsulfinyl, methylsulfonyl, methoxy, ethoxy, cyano or by nitro; or Ri9 is phenyl, heteroaryl or heterocyclyl, it being possible for those phenyl, heteroaryl and heterocyclyl radicals to be mono- or poly-substituted by halogen, d-C4alkyl, d-C4alkoxy, d-C4haloalkyl, C C4haloalkoxy, C2-C4alkenyl, C2-C alkynyl, C2-C4haloalkenyl, C2-C4haIo- alkynyl, C3-C6cycloalkyl, d-C alkylthio, d-C4alkylsuIfinyl, d-C4alkylsulfonyl, d-C4haloalkyl- thio, Cι-C4haloalkylsulfinyl, d-C4haloalkylsulfonyl, cyano, d-C6alkoxycarbonyl or by nitro; and n is 0, 1 or 2; or
Q is a group Q4 (04),
Figure imgf000008_0001
wherein
G is =C(R17)-, -O-, -S(O)„-. -C(O)-, -C(S)- I or and — C=NR 19 (R-|7)R1f
R-!, R2, B and D are as defined hereinbefore; or
Q is a group Q5 (05),
Figure imgf000008_0002
wherein
Rι, R2, A, B and D are as defined hereinbefore, and also the agronomically acceptable salts and stereoisomers of such compounds of formula I.
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 various isomeric pentyl, hexyl, heptyl and octyl radicals. Preference is given to methyl, ethyl, n-propyl, isopropyl and n-butyl.
Alkenyl, alkynyl and allenyl groups may likewise be straight-chained or branched, that also being true of the alkyl, alkenyl and alkynyl moiety of hydroxyalkyl, cyanoalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonyl, alkenyloxycarbonyl-alkyl, alkenyloxy-alkyl, alkynyloxy- alkyl, alkynyl-alkenyl, alkylthio-alkyl, alkylthio-C(O)-alkyl, alkyl-S(O)nr, alkylthioalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylamino, dialkylamino, alkylaminocarbonyl-alkyl, dialkylaminocarbonyl-alkyl, phenylalkyl, B-i-alkyl, B alkenyl, B alkynyl, B alkylthio-alkyl, HOC(O)-alkyl and R^dO^d-dalkyl groups.
There may be mentioned as examples of alkenyl radicals vinyl, allyl, methallyl, 1-methylvinyl, but-2-en-1-yl, pentenyl, 2-hexenyl, 3-heptenyl and 4-octenyl, preferably alkenyl radicals having a chain length of from 3 to 5 carbon atoms.
There may be mentioned as examples of alkynyl radicals propargyl, 1 -methylpropargyl, 3- butynyl, but-2-yn-1 -yl, 2-methylbutyn-2-yl, but-3-yn-2-yl, 1-pentynyl, pent-4-yn-1 -yl, 2- hexynyl, 3-heptyn-1-yl and 4-octyn-1-yl, preferably alkynyl radicals having a chain length of 3 or 4 carbon atoms.
In the above definitions, halogen is to be understood as being iodine, preferably fluorine, chlorine and bromine.
Alkoxy radicals preferably have a chain length of from 1 to 8 carbon atoms. Alkoxy is, for example, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy and tert- butoxy, or a pentyloxy, hexyloxy, heptyloxy or octyloxy isomer, preferably methoxy and ethoxy.
Alkenyloxy is, for example, allyloxy, methallyloxy and but-2-en-1 -yloxy.
Alkynyloxy is, for example, propargyloxy and 1 -methylpropargyloxy.
Suitable haloalkyl radicals include alkyl groups substituted one or more times, especially one to three times, by halogen, halogen being in particular iodine and especially fluorine, chlorine or bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloro- methyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloroethyl, 2,2-dichloroethyl, 2,2,2- trifluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl.
Suitable haloalkenyl radicals include alkenyl groups substituted one or more times by halogen, halogen being in particular bromine or iodine and especially fluorine or chlorine, for example 2- and 3-fluoropropenyI, 2- and 3-chloropropenyl, 2- and 3-bromopropenyl, 2,3,3- trifluoropropenyl, 2,3,3-trichloropropenyl, 4,4,4-trif luorobut-2-en-1 -yl and 4,4,4-trichlorobut-2- en-1 -yl. Among the alkenyl radicals substituted once, twice or three times by halogen, preference is given to those having a chain length of 3 or 4 carbon atoms. The alkenyl groups may be substituted by halogen at saturated or unsaturated carbon atoms.
Suitable haloalkynyl radicals include, for example, alkynyl groups substituted one or more times by halogen, halogen being bromine or iodine and especially fluorine or chlorine, for example 3-fluoropropynyI, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4,4,4-trifluoro-but-2-yn-1-yl. Among the alkynyl radicals substituted one or more times by halogen, preference is given to those having a chain length of from 3 to 5 carbon atoms.
Haloalkoxy is, for example, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2,2,2- trifluoroethoxy, 1 ,1 ,2,2-tetrafluoroethoxy, 2-fluoroethoxy, 2-chloroethoxy and 2,2,2- trichloroethoxy.
Suitable haloalkenyloxy radicals include alkenyloxy groups substituted one or more times by halogen, halogen being in particular bromine or iodine and especially fluorine or chlorine, for example 2- and 3-fluoropropenyloxy, 2- and 3-chloropropenyloxy, 2- and 3-bromopropenyl- oxy, 2,3,3-trif luoropropenyloxy, 2,3,3-trichloropropenyloxy, 4,4,4-trif luoro-but-2-en-1 -yloxy and 4,4,4-trichloro-but-2-en-1 -yloxy.
Alkylsulfonyl is, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, sec-butylsulfonyl, tert-butylsulfonyl, preferably methylsulfonyl and ethylsulfonyl.
Haloalkylsulfonyl is, for example, fluoromethylsulfonyi, difluoromethylsulfonyl, trifluoromethyl- sulfonyl, chloromethylsulfonyl, trichloromethylsulfonyl, 2-fluoroethylsulfonyl, 2,2,2-trifluoro- ethylsulfonyl and 2,2,2-trichloroethylsulfonyl.
Alkylcarbonyl is especially acetyl and propionyl.
Haloalkylcarbonyl is especially trifluoroacetyl, trichloroacetyl, 3,3,3-trifluoropropionyl and 3,3,3-trichloropropionyl.
Cyanoalkyl is, for example, cyanomethyl, cyanoethyl, cyanoeth-1-yl and cyanopropyl. Hydroxyalkyl is, for example, 2-hydroxyethyl, 3-hydroxypropyl and 2,3-dihydroxypropyl.
Alkoxy-alkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n- propoxymethyl, n-propoxyethyl, isopropoxymethyl and isopropoxyethyl.
Alkenyloxy-alkyl is, for example, allyloxy-alkyl, methallyloxy-alkyl and but-2-en-1 -yloxy-alkyl.
Alkynyloxy-alkyl is, for example, propargyloxy-methyl and 1 -methylpropargyloxy-methyl.
Haloalkynyloxy-alkyl is, for example, 3-chloropropynyloxy-methyl and 3-fluoropropynyloxy- methyl.
Alkoxycarbonyl is, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl and n-butoxycarbonyl, preferably methoxycarbonyl and ethoxycarbonyl.
Alkenyloxycarbonyl is, for example, allyloxycarbonyl, methallyloxycarbonyl, but-2-en-1 -yl- oxycarbonyl, pentenyloxycarbonyl and 2-hexenyloxycarbonyl.
The cycloalkyl radicals suitable as substituents are, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
Cycloalkyl-alkyl and halocycloalkyl-alkyl are, for example, cyclopropylmethyl, dimethyl- cyclopropylmethyl, difluorocyclopropylmethyl, dichlorocyclopropylmethyl, dibromocyclo- propylmethyl, 2,2,3,3-tetrafluorocyclobutylmethyl and 2,2-difluoro-3,3-dichlorocyclobutyl- methyl.
The cycloalkyl-containing groups may also be substituted one or more times by further d-C3alkyl groups, especially methyl groups, and by halogen and d-C3haIoalkyl.
The cycloalkylcarbonyl radicals suitable as substituents are, for example, cyclopropyl- carbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl and cyclohexylcarbonyl.
Alkylthio is, for example, methylthio, ethylthio, propylthio and isopropylthio.
Alkylthioalkyl is, for example, methylthioethyl, ethylthioethyl, methylthiopropyl and ethylthiopropyl. Phenyl or benzyl as part of a substituent, for example phenylalkyl, phenylalkenyl, benzyloxy, benzyloxyalkyl, benzylcarbonyl, benzyloxycarbonyl or benzyloxycarbonylalkyl, may be in substituted form, in which case the substituents may be in the ortho-, meta- and/or para- position(s). Substituents are, for example, Cι-C4alkyl, halogen and C C4haloalkyl.
When R4 and R5 together with the nitrogen atom to which they are bonded form a saturated or unsaturated heterocyclic ring which may contain as further hetero atoms O, N or S, the following heterocycles, for example are meant:
Figure imgf000012_0001
, it being possible for those heterocycles to be, in addition, substituted by halogen,
Figure imgf000012_0002
d-C3alkyl, d-C3haloalkyl, d-C3aIkoxy, C C alkoxycarbonyl, d-C3alkyl-S(O)nι-, nitro or by cyano.
A heterocyclyl group (for example in the definitions of R6, Rg and R19) may be aromatic, that is to say have the meaning of heteroaryl, e.g. pyridyl, pyrimidyl, pyrazinyl and pyridazinyl, and also partially or completely saturated and may contain from 1 to 4 nitrogen atoms and/or 1 or 2 oxygen atoms and/or 1 or 2 sulfur atoms. Examples that may be mentioned include the 2- and 3-pyridyl groups, the 2- and 4-pyrimidyl groups, the 1 - and 3-pyrazolyl groups, the 1- and 2-furyl groups, the 1- and 2-thienyl groups, the 2-oxazolyl group, the 1 -oxadiazolyl group, the 1 ,2-oxazol-3-yl group, the 1 ,2-oxazolin-3-yl group, the 1- and 3-triazolyl group, the oxiran-2-yl group, the oxetan-3-yl group, the tetrahydrofur-2-yl group, the tetrahydropyran-2- yl group, the 1 ,3-dioxazolin-2-yl group, the .1 ,3-dioxolan-2-yl group, the ethylenediόxy-2-yl group, the propylenedioxy-2-yl group, the 1 ,3-oxathiazol-2-yl group and also the N- phthalimidyl group.
Corresponding meanings may also be given to the substituents in combined definitions, for example haloalkynyloxy, alkoxy-alkoxy, alkoxycarbonylalkyl, haloalkylcarbonyl-alkyl, alkoxycarbonyl-haloalkyl, cycloalkylcarbonyl-alkyl, alkenylaminocarbonyl-alkyl, alkenyloxy- carbonyl-alkyl, phenylalkenyl, alkenylcarbonyl, alkynylcarbonyl, alkynyloxy-alkyl, haloalkynyloxy-alkyl, R6O-, R4NH-, R4R5N-, alkylthio-C(O)-a!kyl, R9S(O)n1-, R10X2C(O)-, R10X2C(O)-alkyl, B alkyl, Bralkenyl, B alkynyl, B haloalkyl, B haloalkenyl, B^alkoxyalkyl, B1-alkylthioalkyl, B cycloalkyl and B2-C(Rι6)=CH-.
R^C^-fC.-C8alkylene]-
In the definition of R6 the group indicates that the RT-X^O)-
(C6HJ
substituted d-C8alkylene chain is, in addition, substituted by phenyl at one of the 8 carbon atoms, it being possible for the phenyl ring to be mono- to tri-substituted by halogen, C1-C4- alkyl or by C C4haloalkyI and for the alkylene chain to be straight-chained or branched, for example methylene, ethylene, methylethylene, propylene, 1 -methyl-propylene and butylene.
Typical ring systems for the groups Q2, Q3 and Q4 are, for example:
for Q2, e.g. Q2(i) ; for Q3, e.g. Q3(i), Q3(ii), Q3(iii),
Figure imgf000013_0001
Q3(iv) and Q3(v)
(Q3(i)), (Q3(ϋ)) (Q3(iii)),
Figure imgf000013_0002
Figure imgf000013_0003
Figure imgf000013_0004
Figure imgf000013_0005
and for Q4, e.g. Q4(i), Q4(ii), Q4(iii), Q4(iv), Q4(v) and Q4(vi) (Q4(i», (Q4(ϋ)), (Q4(iii)),
Figure imgf000014_0003
(Q4(iv)) (Q4(v)) and (Q4(vi)).
Figure imgf000014_0002
Figure imgf000014_0001
Figure imgf000014_0004
In the definitions of cyanoalkyl, carboxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxy- carbonyl, alkenylcarbonyl, alkynylcarbonyl, alkynyloxycarbonyl-alkyl, haloalkylcarbonyl-alkyl, cycloalkylcarbonyl-alkyl and haloalkylcarbonyl, the upper and lower limits of the number of carbon atoms given in each case do not include the carbon atom of the cyano, carboxy or carbonyl.
The invention also includes the salts that the compounds of formula I may form especially with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Suitable salt formers are described, for example, in WO 99/52892 and WO 97/41112.
The invention also includes the salts that the compounds of formula I may form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases. Among the alkali metal and alkaline earth metal hydroxides used as salt formers, emphasis is to be given to the hydroxides of lithium, sodium, potassium, magnesium and calcium, but especially to those of sodium and potassium.
Examples of amines suitable for ammonium salt formation that come into consideration are ammonia as well as primary, secondary and tertiary Cι-Cι8alkylamines, d-C4hydroxyalkyl- amines and C2-C4alkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, 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-heptyiamine, 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-butyl- ethanolamine, allylamine, n-butenyl-2-amine, n-pentenyl-2-amine, 2,3-dimethylbutenyl-2- amine, dibutenyl-2-amine, n-hexenyl-2-amine, propylenediamine, trimethylamine, triethyl- amine, 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 diisopropyl- amine.
Preferred quaternary ammonium bases that are suitable for salt formation correspond, for example, to the formula [N(RaRbRcRd)]OH, wherein Ra, Rb, Rc and Rd are each independently of the others Cι-C4alkyl. Other suitable tetraalkylammonium bases having different anions can be obtained, for example, by anion exchange reactions.
Also possible - in addition to the formation of salts of compounds of formula I having acid hydrogen, especially the derivatives having carboxylic acid groups (e.g. carboxyl-substituted alkyl and alkylene groups (R6)) - are salts of compounds of formula I having basic groups, especially having basic pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl and imidazolyl rings (group Q3(ii)) or having amino groups, for example alkylamino and dialkylamino groups in the definition of R2 or R3. Such salts are, for example, salts with inorganic or organic acids, e.g. hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydriodic acid, and sulfuric acid, phosphoric acid, nitric acid, and organic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, citric acid, benzoic acid, oxalic acid, formic acid, benzenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid.
The presence of an asymmetric carbon atom in the compounds of formula I, for example in the substituent R2 or R3 = -OR6, wherein R6 is a branched alkyl, alkenyl, alkynyl, haloalkyl or alkoxyalkyl group, or R3 = R9S(O)n -, wherein, for example ^ = 1 or R9 or R19 is a branched
alkyl, alkenyl, alkynyl, haloalkyl or alkoxyalkyl group, or A, B, D or E is P(R17)R18 >
means that the compounds may be in the form of optically active individual isomers or in the form of racemic mixtures. In the present invention, 'compounds of formula I' is to be understood as including both the pure optical antipodes and the racemates or diastereo- isomers.
When an aliphatic C=C or C=N double bond is present, geometric isomerism may occur. As N. an example there may be mentioned the exocyclic group "Q in the compound
of formula I, which can be present in the two geometric isomeric forms <E> and <Z> (syn and anti). The same is also true of aliphatic C=C double bonds as in, for example, the alkenyl or haloalkenyl groups of the substituents R6 or R19. The present invention also includes all such isomers.
Preference is given to compounds of formula la
Figure imgf000016_0001
wherein
X is oxygen or sulfur; and
Q is a group Q1 (Q1 ),
Figure imgf000016_0002
wherein
R2 is hydrogen, d-C4alkyl, C1-C4haloalkyl, halogen, R6O-, nitro, amino, cyano, H2NC(O)-,
H2NC(S)-, HOC(O)- or HC(O)-; and
R3 is halogen, nitro, amino, R4NH-, R4R5N-, R6O-, azido, cyano or CIS(O)2-;
R4 and R5 are each independently of the other C C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6- cycloalkyl, d-C8haloalkyl, C3-C8haloalkenyl, HC(O)-, d-C4alkylcarbonyI, C C4haloalkyl- carbonyl, d-C4alkylsulfonyl, C C4haloaIkyIsulfonyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, Cι-C alkyl or by C C4haloalkyl; or R4 and R5 together with the nitrogen atom to which they are bonded form a saturated or unsaturated heterocyclic ring which contains as further hetero atoms oxygen, nitrogen or sulfur and which may be substituted by halogen, C C3alkyl, d-C3haloalkyl, C C3alkoxy, C-|-C aikoxycarbonyl, Cι-C3alkyl-S(O)π1-, nitro or by cyano;
R6 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycIoalkyl, C C8haloalkyl, cyano-C C8alkyl, C3-C8haloalkenyl, hydroxy-d-C4alkyl, Cι-C4alkoxy-d-C4alkyl, C3-C6- aIkenyloxy-d-C4alkyl, C3-C6alkynyloxy-C C4alkyl, d-dalkoxy-d-dalkoxy-d-dalkyl, d-C4alkylthio-d-C alkyl, d-C8alkylcarbonyl, C C8alkoxycarbonyl, C3-C8alkenyloxycarbonyl, benzyloxy-C or -C2-alkyI, benzylcarbonyl, benzyloxycarbonyl, phenyl, phenyl-d-C8alkyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, it being possible for the afore-mentioned aromatic and heteroaromatic rings to be mono- to tri-substituted by hydroxy, amino, nitro, cyano, CO2H, CONH2, CSNH2, halogen, HC(O)-, C C4alkyl, C2-C4alkenyl, C2-C4alkynyl, d-C4haloalkyl, C2-C4haloalkenyl, C2-C haloalkynyl, d-C4alkoxy, C2-C4aIkenyloxy, C2-C4- alkynyloxy, d-C4haIoalkoxy, C2-C4haloalkenyloxy, C2-C4haloalkynyloxy, d-C4alkylcarbonyl, Cι-C4alkoxycarbonyl, d-C alkoxy-CrC4alkoxy, C C4alkyl-C2-C4aIkenyloxy, C C4alkoxy- carbonyl-CrC4alkoxy, d-C4haloalkoxycarbonyl-d-C alkoxy, d-C4alkenyloxycarbonyl- d-C4alkoxy, C1-C4haIoalkenyloxycarbonyl-C1-C4alkoxy, C C4alkynyloxycarbonyl-d-C4- alkoxy, HOC(O)-C C4alkoxy, d-C4alkylcarbonyl-d-C4alkoxy, HC(O)-d-C4alkoxy, R8(R8)N-C C4alkoxy or by R8(R8)NC(O)-d-C4alkoxy; or
R^CfO) [C.-C8alkylene]-
R6 is R7X1C(O)-C1-C8alkyl- or | ; and
(C6H5)
R7 is hydrogen, d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, d-C8haloalkyl, C3-C8haloalkenyl, C1-C4alkoxy-C1-C4alkyl, drCealkenyloxy-d-dalkyl, C1-C4alkylthio-C1-C4- alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C4a!kyl or by C1-C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, C C4alkyl or by d-C4haloalkyl; or
R3 is R9S(O)n1-; n! is 0, 1 or 2; and
R9 is d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, d-C8haloalkyl, carboxy-d-C4- alkyl, d-C4alkoxycarbonyl-Cι-C4alkyl, benzyloxycarbonyl-d-C4alkyl, C1-C4alkylthio-C(O)- C C4alkyl, C3-C5alkenyloxycarbonyl-C1-C4alkyl, d-C4alkylaminocarbonyl-Cι-C4alkyl, di(C1-C4-alkyl)aminocarbonyl-C1-C4alkyl, drCsalkenylaminocarbonyl-d-dalkyl, C3-C8halo- alkenyl, d-C4alkoxy-d-C4alkyl, C3-C8alkenyloxy-C C alkyl, C1-C4alkylthio-C1-C4alkyl, phenyl, phenyl mono- to tri-substituted by halogen, C C4alkyl or by C1-C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, d-C4alkyl or by C1-C halo- alkyl,
Figure imgf000018_0001
R9 is in addition hydrogen, C C8alkylcarbonyl, R10X2C(O)- or R10X2C(O)-Cι- or -C2-alkyl; or
R3 is R12R13NS(O)2-, Rι4C(O)-, R15X3C(O)-, Brd-dalkyi, B C2-C8alkenyl, B C2-C8alkynyl, B^QrCecycloalkyl, B d-Cshaloalkyl, BrC2-C8haloalkenyl, Brd-dalkoxy-d-dalkyl or B d-dalkylthio-d-dalkyl or B2-C(R16)=CH-; or
Q is a group Q2 or Q3
Figure imgf000018_0002
wherein
A, B, D and E are each independently of the others =C(R17)-, -O-, =N-, -N(R19)-, -S(O)n-,
-C(O)-, -C(S)-, or ; and
-C=NR 19 -C(R17)R1£
R19 is hydrogen, d-C12alkyl, d-Cι2haloalkyl, C2-Cι2alkenyl, C2-C12alkynyl, C2-C8alkynyl- C2-C4alkenyl, C3-C12allenyl, C2-C12haloalkenyl, C2-d2haloalkynyl, C3-C6cycIoalkyl, C3-C6- cycloalkyl-d-C4alkyl, C3-C6halocycloalkyl-d-C4alkyl, tri(C1-C4alkyl)silyl-C1-C4alkyl, tri(d-C4- alkyl)silyI-C2-C4alkenyl, cyano-d-C12alkyl, d-C6alkoxy-d-C4alkyl, CrC alkoxy-d- or -C2- alkoxy-d- or -C2-alkyl, di(C1-C4alkoxy)-C1- or -C2-alkyl, ethylenedioxy-d- or -C2-alkyl, C2-C6alkenyloxy-d-C4alkyl, C2-C6haloalkenyloxy-d-C alkyl, C2-C6alkynyloxy-Cι-C4alkyl, C3-C6haloalkynyloxy-d-C4alkyl, C1-C6alkylthio-C1-C4alkyl, d-C6alkylsulfinyl-d-C4alkyl, d-Cealkylsulfonyl-d-dalkyl, hydroxy-d-C^alkyl, d-Cealkylcarbonyl-d-dalkyl, Q C6halo- alkylcarbonyl-C C alkyl, Cι-C6alkoxycarbonyl-d-C4alkyl, d-Cealkoxy-d- or -C2-alkoxy- carbonyI-d-C alkyl, d-Cealkoxycarbonyl-d-dhaloalkyl, C3-C6cycloalkylcarbonyl-Cι-C4alkyl, or benzoyl-Cι-C4alkyl, it being possible for the benzoyl group to be substituted by halogen, d-C3alkyl, C C3haloalkyl, C C3aIkoxy or by d-C3haloalkoxy, C3-C6alkenyloxycarbonyl- d-C4alkyl, C3-C6alkynyloxycarbonyl-d-C4alkyl, C1-C6alkylcarbonyloxy-C1-C4alkyl, C2-C6alkenylcarbonyloxy-C C4aIkyl, C3-C6cycloalkyIcarbonyIoxy-d-C alkyl, benzoyloxy- d-C alkyl, d-Cealkoxycarbonyloxy-d-dalkyl, carbamoyl-Cι-C4alkyl, d-Cealkylamino- carbonyl-C C4alkyl, or phenyl- or heterocyclyl-substituted d-C4alkyl, it being possible for the phenyl and heterocyclyl groups to be substituted by halogen, d-C6alkyl, d-C6alkoxy, CrC6- haloalkyl, CrC6haloalkoxy, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, C2-C6haIoalkynyl, C3-C6cycloalkyl-Cι-C4alkyl, C3-C6halocycloalky!-d-C4alkyI, cyano-d-C4alkyl, d-C6alkoxy- d-C4alkyl, Cι-C6alkylthio-C C4alkyl, d-C6alkylsulfinyl-Cι-C alkyl, C C6alkyIsulfonyl-Cι-C4- alkyl, hydroxy-d-C4alkyl, d-Cealkylcarbonyl-CrC alkyl, C Cealkoxycarbonyl, C C6alkoxy- carbonyl-d-C4alkyl, d-C6alkoxycarbonyl-Cι-C4haloalkyl, Cι-C6alkoxycarbonyl-Cι-C4alkoxy, CrCealkylcarbonyloxy-CrC4alkyl, C -C6alkoxycarbonyloxy-Cι-C4alkyl, d-C4alkoxy-d-C2- alkoxy-CrC2alkyl, CrC alkylaminocarbonyl, Cι-C6alkylaminocarbonyl-d-C4alkoxy, phenyl, phenoxy or by benzyloxy, it being possible for the phenyl ring of the last three definitions to be substituted by halogen, methyl, trifluoromethyl, methylsulfonyl, methoxy, ethoxy or by cyano; or
Rι9 is phenyl-substituted C2-C4alkeny| or C2-C4alkynyl, it being possible for the phenyl group to be substituted by halogen, methyl, trifluoromethyl, methylthio, methylsulfinyl, methylsulfonyl, methoxy, ethoxy, cyano or by nitro; or
Q is a group Q4 (Q4) or Q5
Figure imgf000019_0001
Figure imgf000019_0002
wherein R0, n0, R^ X,, X2, Rβ, Rio, R12, R13, i4, R15, 3, Bi, B2, R16, R17, Riβ, n and G are as defined for formula I, and A, B, D and R2 are as defined above.
Preference is given to compounds of formula I wherein n0 is 0.
Preference is also given to compounds of formula I wherein R^ is hydrogen, fluorine or chlorine. Of those compounds, special preference is given to those wherein R* is fluorine. Preference is also given to compounds of formula I wherein Q is a group Q1 , and R is halogen. Of those compounds, special preference is given to those wherein R2 is chlorine.
Preference is further given to those compounds of formula I wherein Q is a group Q1 , and R3 is R6O-, R9S(O)ni or Rι5X3C(O)-, especially R6O-.
Preference is given to compounds of formula I wherein Q is a group Q2, especially Q2(i).
Preference is also given to compounds of formula I wherein Q is a group Q3, especially Q3(iv).
Preference is given to those compounds of formula I wherein Q is a group Q4, especially Q4(v).
Special preference is given to those compounds of formula I wherein Q is a group Q2(i), Q3(iv) or Q4(v), and R< is fluorine.
Special preference is given to those compounds of formula I wherein Q is a group Q1 , R2 is chlorine and R3 is R6O-.
The compounds of formula I can be prepared using processes known perse, for example described in WO 99/55693, for example by converting an isothiocyanate of formula II
Q-N=C=S (II), wherein Q is as defined for formula I, with a compound of formula III (in the form of the free base or in salt form)
Figure imgf000020_0001
wherein R0 and n0 are as defined for formula I and Hal is halogen, especially chlorine, bromine or iodine, in an inert organic solvent, for example an ether, e.g. tetrahydrofuran (THF), at temperatures of from -10° to 30°C, preferably from 0° to 20°C, into the compound of formula IV
Figure imgf000021_0001
treating that compound, in accordance with variant a), advantageously in a suitable solvent, for example an aromatic hydrocarbon, e.g. toluene or an isomer of xylene, or an ether, e.g. tetrahydrofuran, with a (thio-)carbonylating agent, e.g. (thio-)phosgene of formula Ma
CI2C(X) (lla), wherein X is oxygen or sulfur, for example in the form of a 20 % solution of (thio-)phosgene in toluene, at from -10° to 30°C, preferably from 0° to 20°C, yielding the compound of formula V
Figure imgf000021_0002
the radicals Q, X and R0 and n0 in the compounds of formulae IV and V being as defined, and then treating that compound in an inert organic solvent, for example an aromatic hydrocarbon, e.g. toluene or an isomer of xylene, with imidazole, with gentle heating at temperatures of from 40° to 80°C, preferably from 50° to 70°C, or treating the compound of formula IV, in accordance with variant b), advantageously in a suitable solvent, for example an aromatic hydrocarbon, e.g. toluene or an isomer of xylene, or an ether, e.g. tetrahydrofuran, with a (thio-)carbonylating agent, e.g. (thio-)phosgene of formula lla
CI2C(X) (lla), wherein X is as defined, for example in the form of a 20 % solution of (thio-)phosgene in toluene, and in the presence of an excess of base (e.g. 3 molar equivalents, based on compound (IV)), for example triethylamine. The structurally isomeric (N-cyclised) compound of formula X
Figure imgf000022_0001
wherein X is oxygen or sulfur and R0, n0 and Q are as defined for formula I, can also be isolated as a subsidiary product. Such subsidiary products of formula X also exhibit pronounced herbicidal activity.
The above procedure for the preparation of compounds of formula I is illustrated in Reaction Scheme 1.
Reaction Scheme 1
Figure imgf000023_0001
IV
Figure imgf000023_0002
Figure imgf000023_0003
solvent, e.g. a xylene, 60°C
Figure imgf000023_0005
Figure imgf000023_0004
V
The compounds of formula II used in Reaction Scheme 1 either are known or can be readily prepared from the corresponding aniline derivatives analogously to standard methods for the preparation of isothiocyanates.
The compounds of formula III in Reaction Scheme 1 are known and can be prepared, for example, as described in WO 99/47525.
The compounds of formula IV in Reaction Scheme 1 are new. Those compounds of formula IV, wherein R0, n0 and Q are as defined for formula I, constitute important intermediates for the synthesis of compounds of formula I and the invention relates also thereto. The reactions to give compounds of formula I are advantageously carried out in aprotic inert organic solvents. Such solvents are hydrocarbons such as benzene, toluene, xylene or cyclohexane, chlorinated hydrocarbons such as dichloromethane, trichloromethane, 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, diethylformamide or N-methylpyrrolidinone. The reaction temperatures are preferably between -20°C and +120°C. In general, the reactions are slightly exothermic and, as a rule, they can be carried out at room temperature. To shorten the reaction time, or else to start the reaction, the mixture may be heated briefly to the boiling point of the reaction mixture. The reaction times can also be shortened 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-diazabicyclo[4.3.0]non-5-ene or 1 ,5-diazabicyclo- [5.4.0]undec-7-ene. However, inorganic bases such as hydrides, e.g. sodium hydride or calcium hydride, hydroxides, e.g. sodium hydroxide or potassium hydroxide, carbonates such as sodium carbonate and potassium carbonate, or hydrogen carbonates such as potassium hydrogen carbonate and sodium hydrogen carbonate, may also be used as bases.
The compounds of formula I can be isolated in customary manner by concentrating and/or by evaporating the solvent and purified by recrystallisation or trituration of the solid residue in solvents in which they are not readily soluble, such as ethers, aromatic hydrocarbons or chlorinated hydrocarbons.
For the use according to the invention of the compounds of formula I, or of compositions comprising them, there 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 desired, 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 can be used as herbicides in unmodified form, that is to say as they are obtained in 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, in WO 97/34485 on pages 9 to 13. As with the nature of the compositions, the methods of application, such as spraying, atomising, dusting, wetting, scattering or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
The formulations, that is to say the compositions, preparations or mixtures comprising the compound of formula I or at least one compound of formula I and, generally, one or more solid or liquid formulation adjuvants, are prepared in known manner, for example by homogeneously mixing and/or grinding the active ingredients with the formulation adjuvants, for example solvents or solid carriers. Furthermore, surface-active compounds (surfactants) may also be used in the preparation of the formulations. Examples of solvents and solid carriers are given, for example, in WO 97/34485 on page 6.
Depending on the nature of the compound of formula I being formulated, suitable surface- active compounds are non-ionic, cationic and/or anionic surfactants and mixtures of surfactants having good emulsifying, dispersing and wetting properties. Examples of suitable anionic, non-ionic and cationic surfactants are listed, for example, in WO 97/34485 on pages 7 and 8. Furthermore, the surfactants customarily employed in formulation technology, which are described, inter alia, in " c Cutcheon's Detergents and Emulsifiers Annual" MC Publishing Corp., Ridgewood New Jersey, 1981 , Stache, H., "Tensid-Taschenbuch", Carl Hanser Verlag, Munich/Vienna, 1981 and M. and J. Ash, "Encyclopedia of Surfactants", Vol l-lll, Chemical Publishing Co., New York, 1980-81 , are also suitable for preparation of the herbicidal compositions according to the invention.
The herbicidal formulations generally comprise 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), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and tackifiers, as well as fertilisers or other active ingredients. The compounds of formula I are generally applied to the plant or to 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 in cereals, cotton, soybeans, sugar beet, sugar cane, plantation crops, rape, maize and rice, and also for non-selective weed control. Crops are to be understood as including also crops that have been made tolerant to herbicides or classes of herbicides by means of conventional plant breeding or by genetic engineering methods. The weeds to be controlled may be either monocotyledonous or dicotyledonous weeds, for example Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria, Sinapis, Lolium, Panicum, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria, Bromus, Alopecurus, Sorghum halepense, Rottboellia, Cyperus, Abutilon, Sida, Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Viola and Veronica.
The compounds of formula I according to the invention can also be used for weed control in admixture with known herbicides as co-herbicides, for example in the form of ready-prepared formulations or in the form of a 'tank-mix'. Suitable mixing partners for the compounds of formula I include, for example, the following co-herbicides:
compound of formula I + acetochlor; compound of formula I + acifluorfen; compound of formula I + aclonifen; compound of formula I + alachlor; compound of formula I + ametryn; compound of formula I + aminotriazole; compound of formula I + amidosulfuron; compound of formula I + asulam; compound of formula I + atrazine; compound of formula I + BAY FOE 5043; compound of formula I + benazolin; compound of formula I + bensulfuron; compound of formula I + bentazone; compound of formula I + bifenox; compound of formula I + bispyribac-sodium; compound of formula I + bialaphos; compound of formula I + bromacil; compound of formula I + bromoxynil; compound of formula I + bromofenoxim; compound of formula I + butachlor; compound of formula I + butylate; compound of formula I + caf enstrole; compound of formula I + carbetamide; compound of formula I + chloridazone; compound of formula I + chlorimuron-ethyl; compound of formula I + chlorbromuron; compound of formula I + chlorsulfuron; compound of formula I + chlortoluron; compound of formula I + cinosulfuron; compound of formula I + clethodim; compound of formula I + clodinafop; compound of formula I + clomazone; compound of formula I + clopyralid; compound of formula I + cloransulam; compound of formula I + cyanazine; compound of formula I + cyhalofop; compound of formula I + dalapon; compound of formula I + 2,4-D; compound of formula I + 2,4-DB; compound of formula I + desmetryn; compound of formula I + desmedipham; compound of formula I + dicamba; compound of formula I + diclofop; compound of formula I + difenzoquat metilsulfate; compound of formula I + diflufenican; compound of formula I + dimefuron; compound of formula I + dimepiperate; compound of formula I + dimethachlor; compound of formula I + dimethametryn; compound of formula I + dimethenamid; compound of formula I + S-dimethenamid; compound of formula I + dinitramine; compound of formula I + dinoterb; compound of formula I + dipropetryn; compound of formula I + diuron; compound of formula I + diquat; compound of formula I + DSMA; compound of formula I + EPTC; compound of formula I + esprocarb; compound of formula I + ethalfluralin; compound of formula I + ethametsulfuron; compound of formula I + ethephon; compound of formula I + ethofumesate; compound of formula I + ethoxysulfuron; compound of formula I + fenclorim; compound of formula I + flamprop; compound of formula I + flazasulfuron; compound of formula I + fluazifop; compound of formula I + flumetralin; compound of formula I + flumetsulam; compound of formula I + fluometuron; compound of formula I + flurochloridone; compound of formula I + fluoxaprop; compound of formula I + fluroxypyr; compound of formula I + f luthiacet-methyl; compound of formula I + fluxofenim; compound of formula I + fomesafen; compound of formula I + glufosinate; compound of formula I + glyphosate; compound of formula I + halosulfuron; compound of formula I + haloxyfop; compound of formula I + hexazinone; compound of formula I + imazamethabenz; compound of formula I + imazapyr; compound of formula I + imazaquin; compound of formula I + imazethapyr; compound of formula I + imazosulfuron; compound of formula I + ioxynil; compound of formula I + isoproturon; compound of formula I + isoxaben; compound of formula 1 + isoxaflutole; compound of formula I + karbutilate; compound of formula I + lactofen; compound of formula I + lenacil; compound of formula I + linuron; compound of formula I + MCPP; compound of formula I + metamitron; compound of formula I + metazachlor; compound of formula I + methabenzthiazuron; compound of formula I + methazole; compound of formula I + metobromuron; compound of formula I + metolachlor; compound of formula I + S-metolachlor; compound of formula I + metosulam; compound of formula I + metribuzin; compound of formula I + metsulfuron- methyl; compound of formula I + molinate; compound of formula I + MCPA; compound of formula I + MSMA; compound of formula I + napropamide; compound of formula I + NDA- 402989; compound of formula I + nefenacet; compound of formula I + nicosulfuron; compound of formula I + norflurazon; compound of formula I + oryzalin; compound of formula I + oxadiazon; compound of formula I + oxasulfuron; compound of formula I + oxyfluorfen; compound of formula I + paraquat; compound of formula I + pendimethalin; compound of formula I + phenmedipham; compound of formula I + phenoxaprop-P-ethyl (R); compound of formula I + picloram; compound of formula I + pretilachlor; compound of formula I + primisulfuron; compound of formula I + prometon; compound of formula I + prometryn; compound of formula I + propachlor; compound of formula I + propanil; compound of formula I + propazine; compound of formula I + propaquizafop; compound of formula I + propyzamide; compound of formula I + prosulf uron; compound of formula I + pyrazolynate; compound of formula I + pyrazosulfuron-ethyl; compound of formula I + pyrazoxyphen; compound of formula I + pyridate; compound of formula I + pyriminobac- methyl; compound of formula I + pyrithiobac-sodium; compound of formula I + quinclorac; compound of formula I + quizalofop; compound of formula I + rimsulfuron; compound of formula I + sequestrene; compound of formula I + sethoxydim; compound of formula I + simetryn; compound of formula I + simazine; compound of formula I + sulcotrione; compound of formula I + sulfosate; compound of formula I + sulfosulfuron-methyl; compound of formula I + tebutam; compound of formula I + tebuthiuron; compound of formula I + terbacil; compound of formula I + terbumeton; compound of formula I + terbuthylazine; compound of formula I + terbutryn; compound of formula I + thiazafluron; compound of formula I + thiazopyr; compound of formula I + thifensulfuron-methyl; compound of formula I + thiobencarb; compound of formula I + tralkoxydim; compound of formula I + triallate; compound of formula I + triasulfuron; compound of formula I + trifluralin; compound of . formula I + tribenuron-methyl; compound of formula I + triclopyr; compound of formula I + triflusulfuron; and compound of formula I + trinexapac-ethyl, and esters and salts of those mixing partners for the compound of formula I that are mentioned e.g. in The Pesticide Manual, Eleventh Edition, 1997, BCPC.
The Examples that follow illustrate the invention without limiting it.
Preparation Examples:
Example P1 : Preparation of compound (4):
Figure imgf000029_0001
6.35 g of compound (3) are introduced into 100 ml of ethyl alcohol at 0-5°C. 4.85 g of triethylamine are then added thereto and stirring is carried out for 10 minutes. 8.7 g of 2- fluoro-4-chloro-5-methoxyphenyl isothiocyanate (compound (2)) are then added. The reaction mixture is then stirred for a further 4 hours at room temperature. 50 ml of water are added to the reaction mixture, the precipitate that forms is filtered off, and washing with water is carried out twice. The crude product is dissolved in dichloromethane and the solution is washed with water three times; the organic phase is dried over sodium sulfate, filtered and concentrated in a water-jet vacuum. The residue obtained is recrystallised using toluene/hexane. The desired target compound (4) is obtained as a brown solid having a melting point of 152-153°C.
Example P2: Preparation of compound no. lι.0Q1
Figure imgf000030_0001
(4) (.,.001)
9.6 g of compound (4) are introduced into 150 ml of tetrahydrofuran at 0-5°C, and 10.9 g of triethylamine are added. At 0-5°C, 18.8 ml of phosgene solution (20 % in toluene) are added dropwise. The reaction mixture is subsequently stirred for 3 hours at room temperature and then concentrated in a water-jet vacuum. The residue obtained is dissolved in ethyl acetate and the organic phase is washed with brine three times. The separated organic phase is dried over sodium sulfate, filtered and concentrated in a water-jet vacuum. The crude product obtained is chromatographed over silica gel (eluant: hexane/ethyl acetate 1/1) at 0.6 mbar and the product obtained is recrystallised from toluene/hexane. The desired target compound no. .001 is obtained as a solid having a melting point of 142-144°C.
In analogous manner, or using the method as described in Reaction Scheme 1 and in the mentioned reference, it is also possible to obtain the preferred compounds listed in the following Tables.
Table 1 : Compounds of formula Ii
Figure imgf000031_0001
Figure imgf000031_0002
Figure imgf000032_0001
Figure imgf000033_0002
Table 2: Compounds of formula l2
Figure imgf000033_0001
Figure imgf000034_0001
Figure imgf000035_0002
Table 3: Compounds of formula l3
Figure imgf000035_0001
Figure imgf000035_0003
Figure imgf000036_0001
Figure imgf000037_0002
Table 4: Compounds of formula l4
Figure imgf000037_0001
Figure imgf000038_0002
Table 5: Compounds of formula l5
Figure imgf000038_0001
Figure imgf000038_0003
Biological Examples:
Example B1 : Herbicidal action before emergence of the plants (pre-emerqence action) Monocotyledonous and dicotyledonous test plants are sown in standard soil in 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 water/ha). The test plants are then grown in a greenhouse under optimum conditions. After a test duration of 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: Setaria (Set), Panicum (Pan), Digitaria (Digi), Sida, Abutilon (Abu), Amaranthus (Ama).
Table B1 : Pre-emerqence action at 250 g a.i./ha
Figure imgf000039_0001
Similarly good results are obtained when the compounds of formula I are formulated in accordance with the other Examples according to WO 97/34485.
Example B2: Post-emergence herbicidal action
Monocotyledonous and dicotyledonous test plants are sown in standard soil in pots. At the 2- to 3-leaf stage, the test plants are sprayed with 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), in an optimum concentration (500 litres water/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: Setaria (Set), Panicum (Pan), Digitaria (Digi), Sida, Abutilon (Abu), Xanthium (Xan), Amaranthus (Ama), Chenopodium (Chen).
Figure imgf000039_0002
Similarly good results are obtained when the compounds of formula I are formulated in accordance with the other Examples according to WO 97/34485.

Claims

What is claimed is:
1. A compound of formula I
Figure imgf000041_0001
wherein
R0 is C,-C4alkyl; n0 is 0 or from 1 to 8;
X is oxygen or sulfur; and
Q is a group Q1 (Q1 ),
Figure imgf000041_0002
wherein
R, is hydrogen, fluorine, chlorine, bromine or methyl;
R2 is hydrogen, C C4alkyl, C,-C4haloalkyl, halogen, R6O-, nitro, amino, cyano, H2NC(O)-,
H2NC(S)-, HOC(O)-, HC(O)- or R9S(O)n,; n, is 0, 1 or 2;
R6 is hydrogen, C,-C18alkyl, C3-C,8alkenyl, C3-C18alkynyl, C3-C6cycloalkyl, C3-C6cycloalkenyl,
Cι-C8haloalkyl, cyano-C,-C8alkyl, C3-C8haloalkenyl, C3-C8cycloalkyl-C,-C4alkyl, C3-C6halo- cycloalkyl-C,-C4alkyl, C3-Cecycloalkyl-C2-C4alkenyl, hydroxy-C,-C8alkyl, Cι-C4alkoxy-C,-C8- alkyl, C3-C6alkenyloxy-C,-C8alkyl, C3-C6alkynyloxy-C,-C8alkyl, d-dalkoxy-d-dalkoxy-
C,-C4alkyl, di(C,-C3alkoxy)C,-C4alkyl, d-dalkylthio-d-dalkyl, C,-C8alkylsulfonyl,
C,-C8haloalkylsulfonyl, C,-C8alkylcarbonyl, C,-C8alkoxycarbonyl, C3-C8aIkenyloxycarbonyI, benzyloxy-Cι-C4alkyl, phenylcarbonyl-Ci- or -C2-alkyl, benzylcarbonyl, benzyloxycarbonyl, phenyl or heteroaryl, it being possible for the afore-mentioned aromatic and heteroaromatic radicals to be mono- to tri-substituted by hydroxy, amino, nitro, cyano, CO2H, CONH2,
CSNH2, halogen, HC(O)-, C,-C4alkyl, C2-C4alkenyl, C2-C4alkynyl, C,-C4haloalkyl, C2-C4halo- alkenyl, C2-C4haloalkynyl, d-C alkoxy, C2-C4alkenyloxy, C2-C4alkynyloxy, CrC4haIoaIkoxy,
C2-C4haloalkenyloxy, C2-C4haloalkynyloxy, C,-C4haloalkylthio, C,-C haloalkylsulfinyl, C,-C4haloalkyIsulfonyl, C,-C4alkylcarbonyl, C,-C4alkoxycarbonyl, d-C4alkoxy-C,-C4alkoxy, C,-C4alkyl-C2-C4alkenyloxy, d-dalkoxycarbonyl-d-dalkoxy, C,-C4haloalkoxycarbonyl- C,-C4alkoxy, C3- or C -alkenyloxycarbonyl-C,-C4alkoxy, C3- or C4-haloalkenyloxycarbonyl- C,-C4alkoxy, C3- or C4-alkynyloxycarbonyl-C,-C4alkoxy, HOC(O)-d-C4alkoxy, C,-C4alkyl- carbonyl-C,-C4alkoxy, HC(O)-C,-C4alkoxy, R8(R8)N-C,-C4alkoxy or by R8(R8)NC(O)-C,-C4- alkoxy; or
R6 is C,-C8alkyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, or C2-C8alkenyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, it being possible for those phenyl, heteroaryl and heterocyclyl radicals to be mono- or poly-substituted by halogen, C,-C4alkyl, C,-C4alkoxy, C,-C4haloalkyl, C,-C4haloalkoxy, C2-C4alkenyl, C2-C4alkynyl, C2-C4haloalkenyl, C2-C4- haloalkynyl, C3-C6cycloalkyl, C,-C4alkylthio, C,-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4halo- alkylthio, C,-C4haloalkylsulfinyl, C,-C4haloalkylsulfonyl, cyano, C,-C6alkoxycarbonyl, nitro, phenyl, phenoxy, heteroaryl or by heteroaryloxy; or R6 is R7X,C(O)-d-C8alkyl-, R7X,C(O)-C2-C8alkenyl- or R7XnC(0) [C.-C8alkylene]-
(C6HJ
v • „ R8-N— R80 - N —
X, is oxygen, sulfur, b ι or 8 ι ;
R7 is hydrogen, C,-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, C,-C8haloalkyl,
C3-C8haloalkenyl, C,-C4alkoxy-C,-C4alkyl, C3-C6alkenyloxy-C,-C4alkyl, d-C4alkylthio-d-C4- alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C alkyl or by d-C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, nitro, C,-C4alkyl or by C,-C4haloalkyl;
R8 is hydrogen, C,-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, C,-C8haloalkyl or benzyl; and
R9 is d-C,8alkyI, C3-C18alkenyl, C3-C,8alkynyl, C3-C6cycloalkyl, C,-C8haloalkyl, C3-C8cyclo- alkyl-C,-C4alkyl, C3-C6halocycloalkyl-C C4alkyl, C3-C6cycloalkenyl, C3-C6cycloalkyl-C2-C4- alkenyl, C3-C8haloalkenyl, C,-C4alkoxy-d-C4alkyl, C3-C6alkenytoxy-d-C4alkyl, di(d-C3- alkoxy)C,-C4aIkyl, C,-C4alkylthio-C,-C4alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C4alkyl or by C,-C haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, d-C4alkyI or by C,-C4haloalkyl, or
Rg is C,-C8alkyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, or C2-C8alkenyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or by heterocyclyloxy, it being possible for those phenyl, heteroaryl and heterocyclyl radicals to be mono- or poly-substituted by halogen, C,-C4alkyl, Cι-C alkoxy,
C,-C haloalkyl, C,-C4haloalkoxy, C2-C4alkenyl, C2-C alkynyl, C2-C4haloalkenyl, C2-C4halo- alkynyl, C3-C6cycloalkyl, C,-C4alkylthio, C1-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4haloalkyl- thio, C,-C4haloalkyIsulfinyl, C,-C4haloalkylsulfonyl, cyano, Cι-C6alkoxycarbonyl, nitro, phenyl, phenoxy, heteroaryl or by heteroaryloxy; or
R9 is R10X2C(O)-d-C8alkyl or R10X2C(O)-C2-C8alkenyl; and, when n, is 0,
R9 is, in addition, hydrogen, d-C8aIkylcarbonyl or R,0X2C(O)-;
X v2 i •s oxygen, sul »fur, R, "TN ι — or R^ "O - N ι — ;
R,0 is hydrogen, C,-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, C,-C8haloalkyl, C3-C8haloalkenyl, C,-C4alkoxy-C,-C4alkyl, C3-C6alkenyloxy-C,-C4alkyI, C,-C4alkylthio-Cι-C4- alkyl, phenyl, phenyl mono- to tri-substituted by halogen, C,-C4alkyl or by C C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, C,-C4alkyl or by d-C4ha!oalkyl; and R,, is hydrogen, C,-C8alkyl or C3-C8alkenyl;
R3 is hydrogen, halogen, nitro, amino, R4NH-, R4R5N-, R6O-, azido, cyano or CIS(O)2-;
R4 and R5 are each independently of the other d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl,
C3-C6cycloalkyl, C C8haloalky!( C3-C8haloalkenyl, HC(O)-, C C4alkylcarbonyl, C C4halo- alkylcarbonyl, C,-C4alkylsulfonyl, C,-C4haloalkylsulfonyl, phenyl, benzyl, or phenyl or benzyl mono- to tri-substituted on the phenyl ring by halogen, Cι-C4alkyl, Cι-C4haloalkyl or by d-C4alkoxy; or
R4 and R5 together with the nitrogen atom to which they are bonded form a saturated or unsaturated heterocyclic ring which contains as further hetero atoms oxygen, nitrogen and/or sulfur and which may be substituted by halogen, C,-C3alkyl, C,-C3haloalkyl, C,-C3alkoxy,
C,-C4alkoxycarbonyl, Cι-C3alkyl-S(O)nι-, nitro or by cyano; or
R3 is R9S(O)n1- or R,2R,3NS(O)2-;
R12 is hydrogen, d-C8alkyl, C2-C8alkenyl, C3-C8alkynyl or C3-C6cycloalkyl;
R,3 is hydrogen, Cι-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C,-C8haloalkyl, C,-C4alkoxy-C,-C4- alkyl, C,-C alkylcarbonyl, C,-C4haloalkylcarbonyl, benzyl, benzoyl, or benzyl or benzoyl mono- to tri-substituted on the phenyl ring by halogen, C,-C4alkyl or by C,-C4haloalkyl; or
R3 is R14C(O)- or R15X3C(O)-; R,4 is hydrogen, fluorine, chlorine, d-C8alkyI, C2-C8alkenyl, C2-C8alkynyl, C3-C6cycloalkyl,
C,-C8haloalkyl, C2-C8haloalkenyl, C,-C4alkoxy-C C alkyl, C3-C6alkenyloxy-d-C alkyl,
C,-C4alkylthio-C,-C4alkyl, phenyl, phenyl mono- to tri-substituted by halogen, C,-C alkyl or by
Cι-C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen,
C C4alkyl or by C,-C4haloalkyl;
Rl N— R.-0- N —
X3 is oxygen, sulfur, η I or 1 ι ;
R15 is hydrogen, C,-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C6cycloalkyl, C,-C8haloalkyl, C -C8haloalkenyl, C2-C8haloalkynyl, C,-C alkoxy-d-C4a!kyl, C3-C6alkenyloxy-C,-C4alkyl, C,-C alkylthio-C,-C4alkyl, Cι-C6alkoxycarbonyl-C,-C6alkyl, C2-C6alkenyloxycarbonyl-Cι-C6- alkyl, C2-C6alkynyloxycarbonyl-Cι-C6alkyl, Cι-C6alkylthio-C(O)-Cι-C6alkyl, C2-C6alkenylthio- C(O)-C,-C6alkyl, C2-C6alkynylthio-C(O)-d-C6alkyl, C,-C6alkylamino-C(O)-C,-C6alkyl, C2-C6- alkenylamino-C(O)-CrC6alkyl, C2-C6alkynylamino-C(O)-Cι-C6alkyl, di(Cι-C6alkyl)amino- C(O)-C,-C6alkyl, di(C2-C6alkenyl)amino-C(O)-C,-C6alkyl, di(C2-C6alkynyl)amino-C(O)-C,- C6alkyl, phenyl, phenyl mono- to tri-substituted by halogen, C C4alkyl or by C,-C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, C,-C4alkyl or by d- dhaloalkyl, phenyl-C2-C8alkyl, or phenyl-C2-C8alkyl mono- to tri-substituted on the phenyl ring by halogen, C,-C4alkyl or by C,-C4haloalkyl, phenyl-C2-C8alkenyl, or phenyl-C2-C8alkenyl mono- to tri-substituted on the phenyl ring by halogen, C,-C4alkyl or by d-C4haloalkyl, or C,- C6alkyl-C(O)-C,-C6alkyl; or
R3 is B,-C,-C8alkyl, B,-C2-C8alkenyl, B,-C2-C8alkynyl, B,-C3-C6cycloalkyl, B,-C,-C8haloalkyl, B,-C2-C8haloalkenyl, B d-dalkoxy-d-dalkyl or B,-C,-C4alkyIthio-C,-C4alkyl; B, is hydrogen, cyano, hydroxy, C,-C8alkoxy, C3-C8alkenyloxy, R7X3C(O)-, C,- C4alkylcarbonyl or Cι-C4haloalkylcarbonyl; or
R3 is B2-C(R,6)=CH-;
B2 is nitro, cyano or R7X3C(O)-; and
R,6 is hydrogen, halogen, cyano or R7X3C(O)-; or
Q is a group Q2 or Q3
Figure imgf000045_0001
wherein
A, B, D and E are each independently of the others =C(R17)-, -O-, =N-, -N(R19)-, -S(O)n-,
-C(O)-, -C(S)-, or
— C=NR 19 -C(R17)Rlt
Ri is as defined hereinbefore; and
Rι7 and R,8 are each independently of the other hydrogen, fluorine, chlorine, bromine, hydroxy, mercapto, amino, cyano, nitro, C,-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C6cyclo- alkyl, C,-C8haIoaIkyl, C2-C8haloalkenyl, C2-C8haloalkynyl, C,-C4alkoxy-C,-C4alkyl, C3-C6- alkenyloxy-d-C4alkyl, C,-C4alkylthio-d-C4alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C4alkyl, C,-C4alkoxy, C,-C4haloalkyl or by d-C4haloalkoxy, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, Cι-C alkyl, C,-C4aIkoxy, C,-C haIo- alkyl or by d-C4haloaIkoxy, phenyl-C2-C8alkyl, or phenyI-C2-C8alkyl mono- to tri-substituted on the phenyl ring by halogen, d-C4alkyl or by C,-C4haloalkyl, phenyl-C2-C8aIkenyl, or phenyl-C2-C8alkenyl mono- to tri-substituted on the phenyl ring by halogen, d-C alkyl or by C-dhaloalkyl, or Cι-C6alkyI-C(O)-d-C6alkyl;
R19 is hydrogen, d-d2alkyl, C,-C,2haloalkyl, C2-C12alkenyl, C2-C12alkynyl, C2-C8alkynyl- C2-C4alkenyl, C3-Cι2allenyl, C2-Cι2haloalkenyl, C2-Cι2haloalkynyl, C3-C6cycloalkyl, C3- C6cycloalkyl-C,-C4alkyl, C3-C6halocycloalkyl-Cι-C4alkyl, tri(C C4alkyl)silyl-C,-C4alkyl, tri(C,- C4alkyl)silyl-C2-C4alkenyl, cyano-C,-C,2alkyl, d-C6alkoxy-d-C4alkyl, C,-C4alkoxy-d- or -C2- alkoxy-Cr or -C2-alkyl, di(C,-C4alkoxy)-C,- or -C2-alkyl, ethylenedioxy-C,- or -C2-alkyl, C2- C6alkenyloxy-C,-C4alkyl, C2-C6haloalkenyloxy-Cι-C4alkyl, C2-C6alkynyIoxy-C C4alkyl, C3- C6haloalkynyIoxy-C,-C4alkyl, C,-C6alkylthio-C,-C4alkyl, C,-C6alkylsulfinyl-C,-C alkyl, C,- C6alkylsulfonyl-C,-C4aIkyl, hydroxy-C,-C,2alkyl, C,-C6alkylcarbonyl-C,-C4alkyl, d- C6haloalkylcarbonyl-C,-C4alkyl, C,-C6alkoxycarbonyl-d-C4alkyl, C,-C6alkoxy-C,- or -C2- alkoxycarbonyI-C,-C4alkyl, Cι-C6alkoxycarbonyl-C,-C4haloalkyl, d-C4alkoxycarbonyl-C3- C6cycloaIkyl, C3-C6cycloalkylcarbonyI-C,-C4alkyl, or benzoyl-C,-C4alkyl, it being possible for the benzoyl group to be substituted by halogen, C,-C3alkyl, C,-C3haloalkyl, C,-C3alkoxy or by C,-C3haloaIkoxy, C3-C6alkenyloxycarbonyl-CrC alkyl, C3-C6alkynyloxycarbonyl-CrC4alkyl, Cι-C6alkylcarbonyloxy-C,-C4alkyl, C2-C6alkenyIcarbonyloxy-C,-C4alkyl, C3- C6cycloalkylcarbonyloxy-d-C4alkyl, benzoyloxy-C,-C4alkyl, C,-C6alkoxycarbonyloxy-Cr C alkyl, carbamoyl-C,-C4alkyl, d-C6alkylaminocarbonyl-C,-C4alkyl, or phenyl- or heterocyclyl-substituted C,-C4alkyl, it being possible for the phenyl and heterocyclyl groups to be substituted by halogen, C,-C6alkyl, C,-C6alkoxy, C,-C6haloalkyl, C,-C6haloalkoxy, C,- C4alkylthio, d-C4alkylsulfinyl, C,-C alkylsulfonyl, C,-C4haloalkylthio, C,-C4haloalkylsulfinyl, C,-C4haloalkylsulfonyl, C2-C6alkenyl, C2-C6alkynyl, C2-C6haloalkenyl, C2-C6haloalkynyl, C3- C6cycIoalkyl-C,-C4alkyl, C3-C6halocycloalkyl-C,-C alkyl, cyano-C,-C alkyl, C,-C6alkoxy-d- C4alkyl, C Cealkylthio-d-C^lkyl, Cι-C6alkylsulfinyl-d-C4alkyl, C,-C6alkylsuIfonyl-C,-C4alkyl, hydroxy-C,-C4alkyl, CrC6alkyIcarbonyl-C,-C4alkyl, d-C6alkoxycarbonyl, C,- C6alkoxycarbonyl-C,-C alkyl, d-Cealkoxycarbonyl-d-dhaloalkyl, d-Cealkoxycarbonyl-d- C4alkoxy, Cι-C6alkylcarbonyloxy-C,-C alkyl, C,-C6alkoxycarbonyloxy-Cι-C4alkyl, C C alkoxy-C,-C2alkoxy-d-C2alkyl, C,-C alkylaminocarbonyl, d-C6alkylaminocarbonyl-C,- C4alkoxy, phenyl, phenoxy or by benzyloxy, it being possible for the phenyl rings of the last three definitions to be in turn substituted by halogen, methyl, trifluoromethyl, methylsulfonyl, methoxy, ethoxy or by cyano; or phenyl-substituted C2-C alkenyl or C2-C4alkynyl, it being possible for the phenyl group to be substituted by halogen, methyl, trifluoromethyl, methylthio, methylsulfinyl, methylsulfonyl, methoxy, ethoxy, cyano or by nitro; or R,9 is phenyl, heteroaryl or heterocyclyl, it being possible for those phenyl, heteroaryl and heterocyclyl radicals to be mono- or poly-substituted by halogen, C,-C4alkyl, C,-C4alkoxy, C,-C4haloalkyl, C,-C4haloalkoxy, C2-C4alkenyl, C2-C4alkynyl, C2-C4haloalkenyl, C2-C haIo- alkynyl, C3-C6cycloalkyl, C,-C4alkylthio, d-C4alkylsulfinyl, C,-C4alkylsulfonyl, C,-C4haIoalkyl- thio, d-dhaloalkylsulfinyl, C,-C4haloalkylsulfonyl, cyano, Cι-C6alkoxycarbonyl or by nitro; and n is 0, 1 or 2; or
Q is a group Q4 (04),
Figure imgf000046_0001
wherein
G is =C(R,7)-, -O-, -S(O)n-, -C(O)-, -C(S)- I or and — C=NR 19 -C(R17)R1£
R,, R2, B and D are as defined hereinbefore; or Q is a group Q5
Figure imgf000047_0001
wherein
R,, R2, A, B and D are as defined hereinbefore, or an agronomically acceptable salt or stereoisomer of such a compound of formula
2. A compound of formula la
Figure imgf000047_0002
wherein
X is oxygen or sulfur; and
Q is a group Q1 (Q1),
Figure imgf000047_0003
wherein
R2 is hydrogen, C,-C4alkyl, C,-C4haloalkyI, halogen, R6O-, nitro, amino, cyano, H2NC(O)-,
H2NC(S)-, HOC(O)- or HC(O)-; and
R3 is halogen, nitro, amino, R4NH-, R4R5N-, R6O-, azido, cyano or CIS(O)2-;
R4 and R5 are each independently of the other d-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6- cycloalkyl, d-C8haloalkyI, C3-C8haloalkenyl, HC(O)-, C C alkylcarbonyl, C,-C4haloalkyl- carbonyl, C,-C4alkylsulfonyl, C,-C4haloalkylsulfonyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, C,-C4alkyl or by C,-C4haloalkyI; or
R4 and R5 together with the nitrogen atom to which they are bonded form a saturated or unsaturated heterocyclic ring which contains as further hetero atoms oxygen, nitrogen or sulfur and which may be substituted by halogen, C,-C3alkyl, C,-C3haloalkyl, d-C3alkoxy, C,-C4alkoxycarbonyl, C,-C3alkyl-S(O)n1-, nitro or by cyano;
R6 is hydrogen, C,-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C8cycloalkyI, C,-C8haloalkyl, cyano-C,-C8alkyl, C3-C8haloalkenyl, hydroxy-C,-C4alkyl, C,-C4alkoxy-C,-C4alkyl, C3-C6- alkeny!oxy-d-C4alkyl, C3-C6alkynyloxy-C,-C4alkyl, Cι-C4alkoxy-Cι-C4aIkoxy-d-C alkyl, C,-C4alkylthio-C,-C4alkyl, C C8alkylcarbonyl, C,-C8alkoxycarbonyl, C3-C8aIkenyloxycarbonyl, benzyloxy-C,- or -C2-alkyl, benzylcarbonyl, benzyloxycarbonyl, phenyl, phenyl-d-C8alkyl, pyridyl, pyrimidinyl, pyrazinyl or pyridazinyl, it being possible for the afore-mentioned aromatic and heteroaromatic rings to be mono- to tri-substituted by hydroxy, amino, nitro, cyano, CO2H, CONH2, CSNH2, halogen, HC(O)-, C C4alkyl, C2-C4alkenyl, C2-C4alkynyl, CrC4haloalkyI, C2-C4haloalkenyl, C2-C4haloalkynyl, C,-C alkoxy, C2-C4alkenyloxy, C2-C alkynyIoxy, C,-C4haloalkoxy, C2-C4haloalkenyloxy, C2-C4haIoalkynyloxy, d-C alkyl- carbonyl, Cι-C4alkoxycarbonyl, C,-C4alkoxy-C,-C4alkoxy, C,-C4alkyl-C2-C4alkenyIoxy, Cι-C alkoxycarbonyl-C,-C4alkoxy, d-C4haloalkoxycarbonyl-d-C4alkoxy, C,-C4alkenyl- oxycarbonyl-C,-C alkoxy, C,-C4haloaIkenyloxycarbonyl-d-C4alkoxy, d-C4alkynyloxy- carbonyl-C,-C4alkoxy, HOC(O)-C,-C4alkoxy, C,-C4alkylcarbonyl-d-C4alkoxy, HC(O)-C,-C - alkoxy, R8(R8)N-C,-C4alkoxy or by R8(R8)NC(O)-C,-C4alkoxy; or
R7X.C(0) [C^Cgalkylenej-
R6 is R7X,C(O)-C,-C8alkyl- or and
(C6HJ
R7 is hydrogen, C,-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, C,-C8haloaIkyl, C3-C8haloalkenyl, C,-C4alkoxy-C1-C4alkyl, C3-C6alkenyloxy-C,-C4alkyl, C,-C alkylthio-d-C4- alkyl, phenyl, phenyl mono- to tri-substituted by halogen, d-C4alkyl or by C,-C4haloaIkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, d-C4alkyl or by C,-C4haloalkyl; or
R3 is R9S(O)n,-; n, is 0, 1 or 2; and
R9 is C,-C8alkyl, C3-C8alkenyl, C3-C8alkynyl, C3-C6cycloalkyl, C,-C8haloalkyl, carboxy-C,-C - alkyl, C,-C4alkoxycarbonyl-C,-C4alkyl, benzyloxycarbonyl-C,-C4alkyl, C,-C4alkylthio-C(O)- C,-C4alkyl, drCsalkenyloxycarbonyl-d-dalkyl, C,-C4alkylaminocarbonyl-C,-C4a!kyl, di(C,-C4-alkyl)aminocarbonyl-C,-C4alkyl, C3-C5alkenylaminocarbonyl-C,-C4alkyl, C3-C8halo- alkenyl, C,-C4alkoxy-C,-C alkyl, C3-C6alkenyloxy-C,-C4alkyl, Cι-C4alkyIthio-d-C4alkyl, phenyl, phenyl mono- to tri-substituted by halogen, C,-C4alkyl or by C,-C4haloalkyl, benzyl, or benzyl mono- to tri-substituted on the phenyl ring by halogen, d-C4alkyI or by d-C halo- alkyl, and, when n, is 0,
R9 is in addition hydrogen, C,-C8alkylcarbonyl, R10X2C(O)- or R10X2C(O)-C - or -C2-alkyl; or
R3 is R,2R,3NS(O)2-, R,4C(O)-, R,5X3C(O)-, B,-C,-C8alkyl, B,-C2-C8alkenyl, B,-C2-C8alkynyl, B,-C3-C6cycloalkyl, B,-C,-C8haloalkyl, B,-C2-C8haloalkenyl, B,-d-C4alkoxy-C,-C4alkyl or B d-C^lkylthio-d-C^lkyl or B2-C(R,6)=CH-; or
Q is a group Q2 or Q3
Figure imgf000049_0001
wherein
A, B, D and E are each independently of the others =C(R,7)-, -O-, =N-, -N(R,9)-, -S(O)n-,
-C(O)-, -C(S)-, or and
C=NR 19 C(R17)R1E
R,9 is hydrogen, C,-C,2alkyl, C,-C,2haloalkyl, C2-C12alkenyl, C2-C,2alkynyl, C2-C8alkynyl- C2-C4alkenyl, C3-C12allenyl, C2-C12haloalkenyl, C2-C,2haloalkynyl, C3-C6cycloalkyl, C3-C6- cycloalkyl-C,-C4alkyl, C3-C6halocycloalkyl-C,-C4alkyl, tri(C,-C4alkyl)silyl-C1-C4alkyl, tri(d-C4- alkyl)siIyl-C2-C4alkenyl, cyano-C,-d2alkyl, Cι-C6alkoxy-C,-C4alkyl, Cι-C4alkoxy-C,- or -C2- alkoxy-C,- or -C2-alkyl, di(C,-C4alkoxy)-C,- or -C2-alkyl, ethylenedioxy-C,- or -C2-alkyf, C2-C6alkenyloxy-CrC4alkyl, C2-C6haloalkenyloxy-C,-C4alkyl, C2-C6alkynyloxy-C,-C4alkyl, C3-C6haloalkynyloxy-Cι-C4alkyl, Cι-C6alkylthio-C,-C4alkyl, Cι-C6alkylsulfinyl-C,-C4alkyl, d-Cealkylsulfonyl-d-dalkyi, hydroxy-C,-C,2aIkyl, C-Cealkylcarbonyl-d-dalkyl, C,-C6halo- alkylcarbonyl-d-C4alkyl, Cι-C6alkoxycarbonyl-d-C4alkyl, d-Cealkoxy-C,- or -C2-alkoxy- carbonyl-C,-C4aIkyl, d-Cealkoxycarbonyl-Crdhaloalkyl, C3-C6cycloalkylcarbonyl-C,-C4alkyl, or benzoyl-C,-C alkyI, it being possible for the benzoyl group to be substituted by halogen, d-C3a!kyl, C,-C3haloalkyl, C,-C3alkoxy or by C,-C3haloalkoxy, C3-C6alkenyloxycarbonyl- C,-C alkyl, C3-C6alkynyIoxycarbonyl-C,-C4alkyl, Cι-C6alkylcarbonyloxy-C,-C alkyl, C2-C6alkenylcarbonyloxy-Cι-C4alkyl, C3-C6cycloalkylcarbonyloxy-Cι-C4alkyl, benzoyloxy- d-C4alkyl, C,-C6alkoxycarbonyloxy-Cι-C4alkyl, carbamoyl-Cι-C aIkyl, C,-C6alkyIamino- carbonyl-C,-C4alkyl, or phenyl- or heterocyclyl-substituted d-C alkyl, it being possible for the phenyl and heterocyclyl groups to be substituted by halogen, d-C6alkyl, Cι-C6alkoxy, d-C6- haloalkyl, C,-C6haloalkoxy, C2-C6alkenyl, C2-C6alkynyl, C2-C6haIoalkenyl, C2-C6haloalkynyl, C3-C6cycloalkyl-C,-C4alkyl, C3-C6haIocycloalkyl-C,-C4alkyl, cyano-C,-C4alkyl, C,-C6alkoxy- C,-C4alkyl, d-C6alkylthio-C,-C4alkyl, C,-C6alkylsulfinyl-CrC4alkyl, C,-C6alkylsulfonyl-C,-C4- alkyl, hydroxy-C,-C4alkyl, C,-C6alkylcarbonyl-Cι-C4alkyl, C,-C6alkoxycarbonyl, C,-C6alkoxy- carbonyl-C,-C4alkyl, d-C6alkoxycarbonyI-Ci-C4haloalkyl, d-Cβalkoxycarbonyl-d-dalkoxy, C, -C6alkylcarbonyloxy-Cι -C al kyl, d -C6alkoxycarbonyIoxy-Cι -C4alkyl, C, -C4alkoxy-C, -C2- alkoxy-CrC2alkyl, C,-C4alkylaminocarbonyl, C,-C6alkyIaminocarbonyl-Cι-C4alkoxy, phenyl, phenoxy or by benzyloxy, it being possible for the phenyl ring of the last three definitions to be substituted by halogen, methyl, trifluoromethyl, methylsulfonyl, methoxy, ethoxy or by cyano; or
R,9 is phenyl-substituted C2-C alkenyl or C2-C4alkynyl, it being possible for the phenyl group to be substituted by halogen, methyl, trifluoromethyl, methylthio, methylsulfinyl, methylsulfonyl, methoxy, ethoxy, cyano or by nitro; or
Q is a group Q4 (Q4) or Q5
Figure imgf000050_0001
Figure imgf000050_0002
wherein R0, n0, R,, X,, X2, R8, R,0, R12, R13, R , R15, X3, B,, B2, R16> R,7, R1B, n and G are as defined in claim 1 , and A, B, D and R2 are as defined above.
3. A process for the preparation of a compound of formula I according to claim 1 , which process comprises converting an isothiocyanate of formula II
Q-N=C=S (II), wherein Q is as defined in claim 1 , with a compound of formula III
Figure imgf000051_0001
wherein R0 and n0 are as defined in claim 1 and Hal is halogen, especially chlorine, bromine or iodine, in an inert organic solvent, at temperatures of from 0° to 20°C, into the compound of formula IV
Figure imgf000051_0002
treating that compound, in accordance with variant a), advantageously in a suitable solvent, with a (thio-)carbonylating agent at from 0° to 20°C, yielding the compound of formula V
Figure imgf000051_0003
the radicals Q and R0 and n0 in the compounds of formulae IV and V being as defined and X being oxygen or sulfur, and then treating that compound in an inert organic solvent with imidazole, with gentle heating at temperatures of from 50° to 70°C, or treating the compound of formula IV, in accordance with variant b), advantageously in a suitable solvent, with a (thio-)carbonylating agent in the presence of an excess of base.
4. A compound of formula IV
Figure imgf000052_0001
wherein R0, n0 and Q are as defined in claim 1.
5. A herbicidal and plant-growth-inhibiting composition comprising a herbicidally effective amount of a compound of formula I on an inert carrier.
6. A method of controlling undesired plant growth, which method comprises applying a compound of formula I, or a composition comprising such a compound, in a herbicidally effective amount to plants or to the locus thereof.
7. A method of inhibiting plant growth, which method comprises applying a compound of formula I, or a composition comprising such a compound, in a herbicidally effective amount to plants or to the locus thereof.
8. A composition according to claim 5, comprising a further herbicide.
PCT/EP2001/010918 2000-09-22 2001-09-20 Bicycloderivatives as herbicides WO2002024709A2 (en)

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WO2009044777A1 (en) * 2007-10-02 2009-04-09 Research Foundation Itsuu Laboratory Oxazolidinone derivative having 7-membered hetero ring
US8530646B2 (en) 2007-10-02 2013-09-10 Research Foundation Itsuu Laboratory Oxazolidinone derivative having 7-membered hetero ring

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