WO2002024704A1 - Nouveaux herbicides - Google Patents

Nouveaux herbicides Download PDF

Info

Publication number
WO2002024704A1
WO2002024704A1 PCT/EP2001/010917 EP0110917W WO0224704A1 WO 2002024704 A1 WO2002024704 A1 WO 2002024704A1 EP 0110917 W EP0110917 W EP 0110917W WO 0224704 A1 WO0224704 A1 WO 0224704A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
phenyl
haloalkyl
halogen
Prior art date
Application number
PCT/EP2001/010917
Other languages
English (en)
Inventor
Roger Graham Hall
Kurt Nebel
Christoph Lüthy
Jean Wenger
Original Assignee
Syngenta Participations Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Priority to AU2001289902A priority Critical patent/AU2001289902A1/en
Publication of WO2002024704A1 publication Critical patent/WO2002024704A1/fr

Links

Classifications

    • 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
    • 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

Definitions

  • the present invention relates to novel herbicidally active fused triazoledione compounds, to processes for their preparation, to compositions comprising these compounds, and to their use for controlling weeds, in particular in crops of useful plants, or for inhibiting plant growth.
  • benzoxa(thia)zol-4-yl- 1 ,6,8-triazabicyc!o[4.3.0]non-2-en-9-one-7-thiones and 2- phenylhexahydro-3-thioxo-1 H-[1 ,2,43triazolo[1 ,2-a]pyridazin-1-ones are described as herbicidally active compounds in WO 00/13508 and US-A-6 121 201 , respectively.
  • 9-(2-pyridyl)- and 9-(6-pyridonyl)-8,10-dioxo-4,1 ,7,9-oxatriaza- bicyclo[5.3.0]decane derivatives are disclosed as herbicidally active compounds in WO 99/52892, WO 99/52893 and in WO 99/55693.
  • R 0 is d-C 4 alkyl; n 0 is 0 or from 1 to 8;
  • X and Y independently of one another are oxygen or sulphur; and Q is a group QI (Q1),
  • R- is hydrogen, fluorine, chlorine, bromine or methyl
  • R 2 is hydrogen, d-C 4 alkyl, C 1 -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 ;
  • ⁇ T is 0, 1 or 2;
  • R 6 is hydrogen, C C 18 alkyl, C 3 -C 18 alkenyl, C 3 -C ⁇ 8 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl, C ⁇ -C 8 haloalkyl, cyano-CrC 8 a!kyl, C 3 -C 8 haloalkenyl, C 3 -C 6 cycloalkyl-C 1 -C 4 alkyl, C 3 -C 6 halocycloalkyI-CrC 4 alkyl, C 3 -C 6 cycloalkyl-C 2 -C 4 alkenyl, hydroxy-d-C 8 aIkyl, C C ⁇ lkoxy-CrCsalkyl, Cs-C ⁇ alkenyloxy-d-Csalkyl, C 3 -C 6 alkynyIoxy-C C 8 alkyl, Ci-C ⁇ lkoxy-CrC ⁇ lk
  • phenoxy, heteroaryloxy or heterocyclyloxy or is C 2 -C 8 alkenyl substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or heterocyclyloxy, where these phenyl, heteroaryl and heterocyclyl radicals may be mono- or polysubstituted by halogen, C C 4 alkyl, C ⁇ -C 4 alkoxy, C C 4 haloalkyl, d-C 4 haloalkoxy, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 2 -C 4 haloalkenyl, C 2 -C 4 haloalkynyI, C 3 -C 6 cycloalkyl, C C 4 alkylthio, C C 4 alkylsulphinyl, C C alkylsulphonyl, d-dhaloalkylthio, d-C haloalkylsulphinyI,
  • R 6 is R 7 X 1 C(O)-C 1 -C 8 alkyl-, R 7 X 1 C(O)-C 2 -C 8 alkenyl or R ⁇ C ⁇ 0) I c ⁇ j c 8 alkylene]- _
  • Xi is oxygen, sulphur, a ⁇ or 8 ⁇ ;
  • 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 ⁇ -C 4 alkoxy-d-C 4 alkyl, C 3 -C 6 aIkenyloxy-C C 4 alkyl, C C 4 alkylthio- d-C 4 alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen, C C 4 alkyl or d-C 4 haloalkyl, benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, nitro, d-C 4 a!kyl or C C 4 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 18 alkyl, C 3 -C 18 alkenyl, C 3 -C 18 alkynyl, C 3 -C 6 cycloaIkyI, C C 8 haIoalkyl,
  • R 9 is C C 8 alkyl, substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or heterocyclyloxy, or C 2 -C 8 alkenyl, substituted by phenyl, heteroaryl, heterocyclyl, phenoxy, heteroaryloxy or heterocyclyloxy, where these phenyl, heteroaryl and heterocyclyl radicals may be mono- or polysubstituted by halogen, d-C 4 alkyl, d-C 4 alkoxy, C C 4 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, d-Cecycloalkyl, d-C alkylthio, C ⁇ -C 4 alkylsulphinyl, CrC 4 alkylsul
  • 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 if is 0,
  • R 9 is additionally hydrogen, d-C 8 aIkylcarbonyl or R 10 X 2 C(O)-; v ⁇ ⁇ L- ' R ⁇ T N — R-.-.O - N —
  • X 2 is oxygen, sulphur, 1 l or 11 ⁇ ;
  • Rio is hydrogen, d-C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 cycloalkyI, d-C 8 haIoalkyl, C 3 -C 8 haloalkenyl, d-C 4 alkoxy-C ⁇ -C 4 alkyl, C 3 -C 6 alkenyloxy-C C 4 alkyI, d,-C 4 alkylthio- d-C alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen, C C 4 alkyl or C ⁇ -C 4 haloalkyl, benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, C 1 -C 4 alkyl or d-C 4 haloalkyl; and Rn is hydrogen, d-C 8 alkyl or C 3 -C 8 alken
  • 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 independently of one another are 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 attached form a saturated or unsaturated heterocyclic ring which contains, as further heteroatoms, oxygen, nitrogen and/or sulphur and which may be substituted by halogen, d-C 3 alkyl, d-C 3 haloalkyl, d-
  • R 3 is R 9 S(O)nr or R ⁇ 2 R ⁇ 3 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, d-C 8 haloalkyl, C ⁇ -C 4 alkoxy-
  • C ⁇ -C alkyl C C 4 alkyIcarbonyl, d-C 4 haloalkylcarbonyl, benzyl, benzoyl or benzyl or benzoyl which is mono- to trisubstituted on the phenyl ring by halogen, d-C 4 alkyl or d-C 4 haloalkyl; or
  • R 3 is R ⁇ 4 C(O)- or R 15 X 3 C(O)-;
  • R 1 is hydrogen, fluorine, chlorine, d-C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 6 cycloaIkyl, d-C 8 haloalkyl, C 2 -C 8 haloalkenyl, C ⁇ -C 4 alkoxy-C C alkyl, C 3 -C6alkenyloxy-d-C 4 alkyI, d-C alky-thio-C C alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen,
  • X 3 is oxygen, sulphur, 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 haloalkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 haloalkynyl, C C 4 alkoxy-C C 4 alkyl, C 3 -C 6 alkenyloxy-d-C 4 alkyl, C ⁇ -C 4 alkylthio-C C 4 alkyl, CrCealkoxycarbonyl-d-Cealkyl, C 2 -C 6 alkenyloxycarbonyl- d-C 6 alkyl, C2-C 6 alkynyloxycarbonyl-C C 6 alkyl, C 1 -C6alkylthio-C(O)-C 1 -C 6 alkyl, C 2 -C 6 alkenylthio-C(O)-d-C 6 al
  • R 3 is B d-Cgalkyl, B C 2 -C 8 alkenyl, B C 2 -C 8 alkynyl, B Cg-Cecycloalkyl, B CrC 8 haloalkyl, B 1 -C 2 -C 8 haloalkenyl, BrCrC 4 alkoxy-d-C 4 alkyl or BrC dalkylthio-C dalkyl; Bi is hydrogen, cyano, hydroxyl, d-C 8 alkoxy, C 3 -C 8 alkenyloxy, R 7 X 3 C(O)-, CrC 4 aIkylcarbonyl or d-C 4 haloalkylcarbonyl; or
  • B 2 is nitro, cyano or R 7 X 3 C(O)-;
  • R 16 hydrogen, halogen, cyano or R 7 X 3 C(O)-; or
  • Q is a group Q2 or Q3
  • R ⁇ 7 and R 18 independently of one another are hydrogen, fluorine, chlorine, bromine, hydroxyl, mercapto, amino, cyano, nitro, C C 8 alkyI, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 6 cycloalkyl, d-C 8 haloalkyl, C 2 -C 8 haloalkenyl, C 2 -C 8 haloalkynyl, d-C 4 alkoxy-d-C 4 alkyl, C 3 -C 6 alkenyloxy-CrC 4 alkyl, C 1 -C 4 alkylthio-C 1 -C 4 alkyl I phenyl, phenyl which is mono- to trisubstituted by halogen, C C 4 alkyl, C C 4 alkoxy, d-dhaloalkyl or C C 4 haloalkoxy, benzyl or benzyl which is mono
  • Q is a group Q4 (04),
  • G C(R 17 )-, -O-, -S(O) n -, -C(O)-, -C(S)-, and
  • Ri, R 2 , B and D have the meaning given above; or
  • Q is a group Q5
  • R 1 R 2 , A, B and D have the meaning given above, and the agronomically acceptable salts and stereoisomers of the compounds of the formula I.
  • alkyl groups occurring in the substituent definitions can be straight-chain 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. Methyl, ethyl, n-propyl, isopropyl and n-butyl are preferred.
  • Alkenyl, alkynyl and allenyl groups can likewise be straight-chain or branched, this also applying to the alkyl, alkenyl and alkynyl moiety of the hydroxyalkyl, cyanoalkyl, alkylcarbonyl, alkylcarbonylalkyl, alkoxycarbonyl, alkenyloxycarbonylalkyl, alkenyloxyalkyl, alkynyloxyalkyl, alkynylalkenyl, alkylthioalkyl, alkylthio-C(O)-alkyl, alkyl-S(O) n1 , alkylthioalkyl, alkoxyalkyl, alkoxyalkoxyalkyl, alkylamino, dialkylamino, alkylaminocarbonylalkyl, dialkylaminocarbonylalkyl, phenylalkyl, B alkyl, B alkenyl, B alkynyl, B
  • alkenyls which we have mentioned are 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 examples include 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 meaning iodine and, 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, and also the isomeric pentyloxy, hexyloxy, heptyloxy and octyloxy, preferably methoxy and ethoxy.
  • Alkenyloxy is, for example, allyloxy, methallyloxy and but-2-en-1 -yloxy.
  • Alkynyloxy is, for example, propargyloxy and 1 -methylpropargyloxy.
  • Haloalkyl can be alkyl groups which are mono- or polysubstituted, in particular mono- to trisubstituted, by halogen, halogen being specifically iodine and, in particular, fluorine, chlorine and bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2-chloroethyI, 2,2- dichloroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl.
  • halogen being specifically iodine and, in particular, fluorine, chlorine and bromine, for example fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2-fluoroethyl, 2,2-difluoroethy
  • Haloalkenyl can be alkenyl groups which are mono- or polysubstituted by halogen, halogen being specifically bromine, iodine and, in particular, fluorine and chlorine, for example 2- and 3-fluoropropenyl, 2- and 3-chloropropenyl, 2- and 3-bromopropenyl, 2,3,3-trifluoropropenyl, 2,3,3-trichloropropenyl, 4,4,4-trifluoro-but-2-en-1 -yl and 4,4,4-trichlorobut-2-en-1 -yl.
  • alkenyl radicals which are mono-, di- or trisubstituted by halogen, preference is given to those having a chain length of 3 or 4 carbon atoms.
  • the alkenyl groups can be substituted by halogen on saturated or unsaturated carbon atoms.
  • Haloalkynyl can be, for example, alkynyl groups which are mono- or polysubstituted by halogen, halogen being bromine, iodine and, in particular, fluorine and chlorine, for example 3-fluoropropynyl, 3-chloropropynyl, 3-bromopropynyl, 3,3,3-trifluoropropynyl and 4,4,4- trifluorobut-2-yn-1-yl.
  • halogen being bromine, iodine and, in particular, fluorine and chlorine
  • alkynyl radicals which are mono- or polysubstituted 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.
  • Haloalkenyloxy can be alkenyloxy groups which are mono- or polysubstituted by halogen, halogen being specifically bromine, iodine and, in particular, fluorine and chlorine, for example 2- and 3-fluoropropenyloxy, 2- and 3-chIoropropenyloxy, 2- and 3- bromopropenyloxy, 2,3,3-trifluoropropenyloxy, 2,3,3-trichloropropenyloxy, 4,4,4-trifluorobut- 2-en-1 -yloxy and 4,4,4-trichlorobut-2-en-1 -yloxy.
  • Alkylsulphonyl is, for example, methylsulphonyl, ethylsulphonyl, propylsulphonyl, isopropylsulphonyl, n-butylsulphonyl, isobutylsulphonyl, sec-butylsulphonyl, tert- butylsulphonyl, preferably methylsulphonyl and ethylsulphonyl.
  • Haloalkylsulphonyl is, for example, fluoromethylsulphonyl. difluoromethylsulphonyl, trifluoromethylsulphonyl, chloromethylsulphonyl, trichloromethylsulphonyl, 2- fluoroethylsulphonyl, 2,2,2-trifluoroethylsulphonyl and 2,2,2-trichloroethylsulphonyl.
  • Alkylcarbonyl is in particular acetyl and propionyl.
  • Haloalkylcarbonyl is in particular 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.
  • Alkoxyalkyl is, for example, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, n- propoxymethyl, n-propoxyethyl, isopropoxymethyl and isopropoxyethyl.
  • Alkenyloxyalkyl is, for example, allyloxyalkyl, methallyloxyalkyl and but-2-en-1 -yloxyalkyl.
  • Alkynyloxyalkyl is, for example, propargyloxymethyl and 1-methylpropargyloxymethyl.
  • Haloalkynyloxyalkyl is, for example, 3-chloropropynyloxymethyl 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 which are suitable substituents are, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.
  • Cycloalkylalkyl and halocycloalkylalkyl are, for example, cyclopropylmethyl, dimethylcyclopropylmethyl, difluorocyclopropylmethyl, dichlorocyclopropylmethyl, dibromocyclopropylmethyl, 2,2,3,3-tetrafluorocyclobutylmethyl and 2,2-difluoro-3,3- dichlorocyclobutylmethyl.
  • the cycloalkyl-containing groups can furthermore be mono- or polysubstituted by further
  • C ⁇ -C 3 alkyl groups in particular by methyl groups, and also by halogen and d-C 3 haloalkyl.
  • cycloalkylcarbonyl radicals which are suitable substituents are, for example, cyclopropylcarbonyl, 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, can be present in substituted or unsubstituted form.
  • the substituents can then be in the ortho-, meta- and/or para-position.
  • Substituents are, for example, C C 4 alkyl, halogen or d-C 4 haloalkyl.
  • R 4 and R 5 together with the nitrogen atom to which they are attached form a saturated or unsaturated heterocyclic ring which may, as further heteroatoms, contain O, N or S means, for example, the following heterocycles:
  • heterocycles may additionally be substituted by halogen, d-C 3 - alkyl, d-C 3 -haloalkyl, C C 3 -alkoxy, d-C 4 -alkoxycarbonyl, C ⁇ -C 3 -a]ky ⁇ -S(O) n ⁇ -, nitro or cyano.
  • a heterocyclyl group (for example in the definition of R 6 , R 9 and R ⁇ 9 ) can either be aromatic, i.e. in the meaning of heteroaryl, for example pyridyl, pyrimidyl, pyrazinyl or pyridazinyl, or partially or fully saturated and contain from 1 to 4 nitrogen atoms and/or 1 or 2 oxygen atoms and/or 1 or 2 ⁇ 5 ⁇ lpt ⁇ r atoms.
  • Examples which may be mentioned are the 2- and 3-pyridyl groups, the 2- and 4-pyrimidyl groups, the 1- and 3-pyrazoIyl groups, the 1- and 2-furyI 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 groups, 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 ethylenedioxy-2-yl group, the propylenedioxy-2-yl group, the 1 ,3-oxathiazoI-2-yl group
  • Corresponding definitions can also be assigned to the substituents in composite definitioins, for example haloalkynyloxy, alkoxyalkoxy, alkoxycarbonylalkyl, haloalkylcarbonylalkyl, alkoxycarbonylhaloalkyl, cycloalkylcarbonylalkyl, alkenylaminocarbonylalkyl, alkenyloxycarbonylalkyl, phenylalkenyl, alkenylcarbonyl, alkynylcarbonyl, alkynyloxyalkyl, haloalkynyloxyalkyl, R 6 O-, R 4 NH-, R 4 R 5 N-, alkylthio-C(O)-alky), R 9 S(O) ⁇ 1 -, R 10 X 2 C(O)-, R ⁇ 0 X 2 C(O)-alkyl, Bralkyl, B alkenyl, B alkynyl, B
  • substituted d-C 8 alkylene chain is additionally substituted by phenyl on one of the 8 carbon atoms, where the phenyl ring may be mono- to trisubstituted by halogen, C r C 4 -alkyl or d- C -haloalkyl and the alkylene chain may be straight-chain or branched and may be, for example, methylene, ethylene, methylethylene, propylene, 1 -methylpropylene and butylene.
  • Typical ring systems for the groups Q2, Q3 and Q4 are, for example:
  • cyanoalkyl carboxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkenylcarbonyl, alkynylcarbonyl, alkynyloxycarbonylalkyl, haloalkylcarbonylalkyl, cycloalkylcarbonylalkyl and haloalkylcarbonyl
  • the cyano, carboxy or carbonyl carbon atom is not included in the respective lower and upper carbon number limits stated.
  • the invention also relates to salts which the compounds of the formula I may form, preferably 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 relates to the salts which the compounds of the formula I may form with amines, alkali metal and alkaline earth metal bases or quaternary ammonium bases.
  • alkali metal and alkaline earth metal hydroxides as salt formers, emphasis is given to the hydroxides of lithium, sodium, potassium, magnesium or calcium, in particular those of sodium or potassium.
  • amines which are suitable for ammonium salt formation include ammonia and also primary, secondary and tertiary d-C ⁇ 8 alkylamines, d-C 4 hydroxyaIky!amines and C 2 - dalkoxyalkylamines, for example methylamine, ethylamine, n-propylamine, isopropylamine, the four isomeric butylamine, n-amylamine, isoamylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, eth
  • Preferred quartemary ammonium bases suitable for salt formation correspond, for example, to the formula [N(R a R b R 0 a )]OH, in which R a , Rb, R c and R d independently of one another are C C 4 alkyl.
  • R a , Rb, R c and R d independently of one another are C C 4 alkyl.
  • Other suitable tetraalkylammonium bases with other anions can be obtained, for example, by anion exchange reactions.
  • salts of the compounds of the formula I having acidic hydrogen in particular the derivatives having carboxylic acid groups (for example carboxyl-substituted alkyl and alkylene groups (R 6 )), salts of the compounds of the formula I with basic groups are possible, too, in particular with basic pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl and imidazolyl rings (group Q3(ii)) or with amino groups, for example alkylamino and dialkylamino groups in the definition of R 2 or R 3 .
  • salts with inorganic and organic acids for example hydrohalic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid, and also sulphuric acid, phosphoric acid, nitric acid and organic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, citric acid, benzoic acid, oxalic acid, formic acid, benzenesulphonic acid, p-toluenesulphonic acid and methanesulphonic acid.
  • hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid
  • sulphuric acid such as acetic acid, trifluoroacetic acid, trichloroacetic acid, propionic acid, glycolic acid, thiocyanic acid, citric acid, benzoic acid, oxalic acid, formic acid, benz
  • R 6 is a branched alkyl, alkenyl, alkynyl, haloalkyl or alkoxyalkyl group
  • X is oxygen or sulphur
  • Q is a group Q1 (Q1 ),
  • R 2 is hydrogen, d-C 4 alkyl, d-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 independently of one another are d-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 attached form a saturated or unsaturate heterocyclic ring which contains, as further heteroatoms, oxygen, nitrogen or sulphur and which may be substituted by halogen, d-C 3 alkyl, C C 3 haloalkyl, d-C 3 alkoxy, d-dalkoxycarbonyl, C ⁇ -C 3 aIkyl-S(O) n1 -, nitro or cyano;
  • R 6 is hydrogen, C ⁇ -C 8 alkyl, C 3 -C 8 alkenyl, C 3 -C 8 alkynyl, C 3 -C 6 cycloalkyl, C C 8 haloalkyl, cyano-d-C 8 alkyl, C 3 -C 8 haloalkenyl, hydroxy-C C alkyl, d-C 4 alkoxy-d-C 4 alkyl,
  • R 6 is R 7 X 1 C(O)-C 1 -C 8 alkyl- or I ;
  • R 7 is hydrogen, 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, d-dalkoxy-d-dalkyl, C 3 -C 6 alkenyloxy-C C 4 alkyl, C ⁇ -C 4 alkyIthio- d-C 4 alkyl, phenyl, phenyl which is mono- to trisubstituted by halogen, d-C 4 alkyl or d-C 4 haloalkyl, benzyl or benzyl which is mono- to trisubstituted on the phenyl ring by halogen, d-C 4 alkyl or d-C haloalkyl; or
  • R 9 is C 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, C 1 -C 4 alkoxycarbonyl-d-C 4 alkyl, benzyloxycarbonyl-C ⁇ -C 4 alkyl, d-C 4 alkylthio-
  • C(O)-CrC 4 alkyl C3-C5alkenyloxycarbonyl-CrC 4 alkyl, d-C ⁇ lkylaminocarbonyl-d-dalkyl, di-(C ⁇ -C4alkyl-)aminocarbonyl-d-C 4 alkyl, C 3 -C 5 alkenylaminocarbonyl-d-C 4 alkyl,
  • R 9 is additionally hydrogen, C C 8 alkylcarbonyl, R 10 X 2 C(O)- or R 10 X 2 C(O)-C or -C 2 alkyl; or
  • R 19 is hydrogen, d-C ⁇ 2 alkyl, C C ⁇ haloalkyl, C 2 -C 12 alkenyl, C 2 -C ⁇ 2 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-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- (C 1 -C 4 alkyl)silyl-C 2 -C 4 alkenyl, cyano-C ⁇ C ⁇ alkyl, d-Cealkoxy-d-dalkyl,
  • Q is a group Q4 (Q4) or Q5
  • R 0 , n 0 , R 1 t X 1 f X 2 , R 8 , Rio, R12, R13, R ⁇ , R15, X3, Bi, B 2 , R 16 , R ⁇ 7 , R ⁇ 8 , n and G are as defined under formula I and A, B, D and R 2 are as defined above.
  • Preferred compounds of the formula I are characterized in that n 0 is 0.
  • Preferred compounds of the formula I are those in which Q is a group Q4, in particular Q4(v).
  • Particularly preferred compounds of the formula I are those in which Q is a group Q1 , R 2 is chlorine and R 3 is R 6 O-.
  • the compounds of the formula I can be prepared by processes known per se, for example that described in WO 99/55693, by converting, for example, an iso(thio)cyanate of the forrhula II
  • R 0 and n 0 have the meaning given under formula I and Hal is halogen, in particular chlorine, bromine or iodine, in an inert organic solvent such as an ether, for example tetrahydrofuran (THF), at temperatures of from -10° to 30°C, preferably from 0° to 20°C, into the compound of the formula IV which, according to variant a), is expediently treated in a suitable solvent, such as an aromatic hydrocarbon, for example toluene or the isomeric xylenes, or an ether, for example tetrahydrofuran, with a (thio)carbonylating agent, for example (thio)phosgene of the formula Ha
  • a suitable solvent such as an aromatic hydrocarbon, for example toluene or the isomeric xylenes, or an ether, for example tetrahydrofuran, with a (thio)carbonylating agent, for example (thio)phosgene of the formula Ha
  • the radicals Q, X, Y, R 0 and n 0 are as defined above, which is subsequently, in inert organic solvents such as aromatic hydrocarbons, for example toluene or the isomeric xylenes, and with gentle heating to temperatures of from 40° to 80°C, preferably from 50° to 70°C, treated with imidazole, or the compound of the formula IV, according to variant b), expediently in a suitable solvent such as an aromatic hydrocarbon, for example toluene or the isomeric xylenes, or in ether, for example tetrahydrofuran, is treated with a (thio)carbonylating agent, for example (thio)phosgene of the formula I la
  • CI 2 C(Y) (lla) in which Y is as defined above, for example as a 20% (thio)phosgene solution in toluene, and in the presence of an excess of base (for example 3 molar equivalents, based on the compound (IV)).
  • reaction scheme 1 The process for preparing compounds of the formula I is illustrated in reaction scheme 1. Reaction scheme 1
  • solvent e.g. toluene, 0°-20°C
  • base e.g. triethylamine
  • the compounds of the formula II to be used in reaction scheme 1 are either known or can easily be prepared from the corresponding aniline derivatives, analogously to standard methods for the preparation of iso(thio)cyanates.
  • the compounds of the formula IV in reaction scheme 1 are novel. These compounds of the formula IV, in which R 0 , n 0 , X and Q are as defined under formula I, are important intermediates for the synthesis of the compounds of the formula I.
  • the invention also relates to these compounds.
  • aprotic inert organic 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.
  • hydrocarbons such as benzene, toluene, xylene or cyclohexane
  • chlorinated hydrocarbons such as dichloromethane, trichloromethane, tetrachloromethane or chlorobenzene
  • ethers such as diethyl
  • reaction temperatures are advantageously 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, in particular, 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.
  • the compounds of the formula I can be isolated in the customary manner by concentrating and/or by evaporating the solvent and purified by recrystallization 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 the formula I can be employed as herbicides as such, i.e. as obtained from synthesis. However, they are preferably processed in the customary manner together with the auxiliaries conventionally used in the art of formulation, for example to give emulsifiable concentrates, directly sprayable or dilutable solutions, dilute emulsions, wettable powders, soluble powders, dusts, granules or microcapsules.
  • auxiliaries conventionally used in the art of formulation, for example to give 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 application methods such as spraying, atomizing, dusting, wetting, scattering or pouring, as well as the type of composition, are chosen to suit the intended aims and the prevailing
  • compositions, preparations or products which comprise the active ingredient of the formula I or at least one active ingredient of the formula I and, as a rule, one or more solid or liquid formulation auxiliaries are prepared in the known manner, for example by intimately mixing and/or grinding the active ingredients together with the formulation auxiliaries, for example solvents or solid carriers.
  • formulation auxiliaries for example solvents or solid carriers.
  • surface-active compounds surfactants
  • solvents and solid carriers are indicated for example in WO 97/34485 on page 6.
  • Suitable surface-active compounds are, depending on the nature of the active ingredient of the formula I to be formulated, nonionic, cationic and/or anionic surfactants and surfactant mixtures which have good emulsifying, dispersing and wetting properties.
  • suitable anionic, nonionic and cationic surfactants are enumerated, for example, in WO 97/34485 on pages 7 and 8.
  • the herbicidal formulations comprise 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of herbicide, 1 to 99.9% by weight, in particular 5 to 99.8% by weight, of a solid or liquid formulation auxiliary and 0 to 25% by weight, in particular 0.1 to 25% by weight, of a surfactant.
  • concentrated compositions are more preferred as commercially available goods, the end consumer uses, as a rule, dilute compositions.
  • the compositions can also comprise further additives such as stabilizers, for example epoxidized or non-epoxidized vegetable oils (epoxidized coconut oil, rapeseed oil or soya oil), antifoams, e.g. silicone oil, preservatives, viscosity regulators, binders, tackifiers and fertilizers or other active ingredients.
  • the active ingredients of the formula I are applied to the plant or its environment at rates of 0.001 to 4 kg/ha, in particular 0.005 to 2 kg/ha.
  • the dosage required for the desired action can be determined by experiments. It depends on the type of the action, the developmental stage of the crop plant and of the weed, and on the application (location, timing, method) and can, owing to these parameters, vary within wide limits.
  • the compounds of the formula I are distinguished by herbicidal and growth-inhibitory properties which allow them to be employed in crops of useful plants, in particular in cereals, cotton, soya, sugar beet, sugar cane, plantation crops, rapeseed, maize and rice and for the non-selective control of weeds.
  • Crops are also to be understood as including those which have been rendered tolerant to herbicides or classes of herbicides by means of conventional plant-breeding or genetic-engineering methods.
  • the weeds to be controlled may be both mono- and dicotyledonous weeds such as 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, Abutilon, Si
  • the active compounds of the formula 1 according to the invention can also be used in mixtures with known herbicides as coherbicides for the control of weeds, for example as finished formulations or as tank mix.
  • Suitable mixing partners for the active compounds of the formula I are, for example, the following coherbicides:
  • 0.10 g of the compound (5) is initially charged in 4 ml of a mixture of xylene isomers, and 0.06 g of imidazole is then added.
  • the reaction mixture is heated to 60°C and stirred at this temperature for 3 hours.
  • the reaction mixture is then poured into dilute hydrochloric acid and extracted twice with ethyl acetate.
  • the combined organic phases are washed twice with brine, dried over sodium sulphate and concentrated under water pump vacuum.
  • the crude product is triturated with hexane/ethyl acetate, filtered off using a nutsche filter, washed with hexane and then dried under reduced pressure.
  • Test plants Setaria (Set), Panicum (Pan), Digitaria (Digi), Sida, Abutilon (Abu), Xanthium (Xanth), Amaranthus (Ama), Chenopodium (Chen), Veronica (Ver).
  • Monocotyledonous and dicotyledonous test plants are grown in standard soil in pots.
  • the test substances are sprayed at optimum dosage (500 I of water/ha) as an aqueous suspension (prepared from a wettable powder (Example F3, b) according to WO 97/34485) or emulsion (prepared from an emulsion concentrate (Example F1 , c) according to WO 97/34485).
  • Test plants Setaria (Set), Panicum (Pan), Digitaria (Digi), Sida, Abutilon (Abu), Xanthium (Xanth), Amaranthus (Ama), Chenopodium (Chen).

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Composés représentés par la formule (I), dans laquelle R0 représente alkyle C1-C4; n0 est zéro ou de 1 à 8; X et Y représentent indépendamment oxygène ou soufre et Q représente un groupe Q1 (Q1), Q2 (Q2), Q3 (Q3), Q4 (Q4), ou Q5 (Q5), dans lesquelles R1 représente hydrogène, fluor, chlore, brome ou méthyle; R2 représente hydrogène, alkyle C1-C4, haloalkyle C1-C4, halogène, R6O-, nitro, amino, cyano, H2NC(O)-, H2NC(S)-, HOC(O)-, HC(O)- ou R9S(O)n1; et n1 est 0, 1 ou 2 et les substituants R3, R6, R9, A, B, D, E et G sont tels que définis dans la revendication 1, ces composés pouvant être utilisés avantageusement en tant qu"herbicides.
PCT/EP2001/010917 2000-09-22 2001-09-20 Nouveaux herbicides WO2002024704A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2001289902A AU2001289902A1 (en) 2000-09-22 2001-09-20 Novel herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1857/00 2000-09-22
CH18572000 2000-09-22

Publications (1)

Publication Number Publication Date
WO2002024704A1 true WO2002024704A1 (fr) 2002-03-28

Family

ID=4566539

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2001/010917 WO2002024704A1 (fr) 2000-09-22 2001-09-20 Nouveaux herbicides

Country Status (3)

Country Link
AR (1) AR030779A1 (fr)
AU (1) AU2001289902A1 (fr)
WO (1) WO2002024704A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009044777A1 (fr) * 2007-10-02 2009-04-09 Research Foundation Itsuu Laboratory Dérivé d'oxazolidinone avec hétérocycle à 7 chaînons
WO2010102758A3 (fr) * 2009-03-11 2011-01-20 Bayer Cropscience Ag Cétoénols à substitution halogénoalkylméthylèneoxy-phényle
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides
WO2016039404A1 (fr) * 2014-09-12 2016-03-17 公益財団法人相模中央化学研究所 Dérivé de la pyrazolinone, son procédé de fabrication et herbicide le contenant en tant que principe actif

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0210137A2 (fr) * 1985-07-24 1987-01-28 Ciba-Geigy Ag Composés triazolo condensés
WO1995027698A1 (fr) * 1994-04-08 1995-10-19 E.I. Du Pont De Nemours And Company Herbicides a base d'imides bicycliques et tricycliques
WO2000001700A1 (fr) * 1998-07-03 2000-01-13 Basf Aktiengesellschaft Procede de preparation de triazols anneles et nouveaux triazols anneles et leur utilisation

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0210137A2 (fr) * 1985-07-24 1987-01-28 Ciba-Geigy Ag Composés triazolo condensés
WO1995027698A1 (fr) * 1994-04-08 1995-10-19 E.I. Du Pont De Nemours And Company Herbicides a base d'imides bicycliques et tricycliques
WO2000001700A1 (fr) * 1998-07-03 2000-01-13 Basf Aktiengesellschaft Procede de preparation de triazols anneles et nouveaux triazols anneles et leur utilisation

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009044777A1 (fr) * 2007-10-02 2009-04-09 Research Foundation Itsuu Laboratory Dérivé d'oxazolidinone avec hétérocycle à 7 chaînons
EP2233484A3 (fr) * 2007-10-02 2012-04-04 Research Foundation Itsuu Laboratory Dérivés de oxazolidone ayant un cycle hétérocyclique à sept membre
US8530646B2 (en) 2007-10-02 2013-09-10 Research Foundation Itsuu Laboratory Oxazolidinone derivative having 7-membered hetero ring
WO2010102758A3 (fr) * 2009-03-11 2011-01-20 Bayer Cropscience Ag Cétoénols à substitution halogénoalkylméthylèneoxy-phényle
JP2012520242A (ja) * 2009-03-11 2012-09-06 バイエル・クロップサイエンス・アーゲー ハロゲンアルキルメチレンオキシフェニル置換ケトエノール類
US8518985B2 (en) 2009-03-11 2013-08-27 Bayer Cropscience Ag Haloalkylmethyleneoxyphenyl-substituted ketoenols
US9045390B2 (en) 2009-03-11 2015-06-02 Bayer Cropscience Ag Haloalkylmethyleneoxyphenyl-substituted ketoenols
EA024266B1 (ru) * 2009-03-11 2016-09-30 Байер Интеллектуэль Проперти Гмбх Кетоенолы, замещенные галоидалкилметиленоксифенилом, и их применение
WO2012041789A1 (fr) 2010-10-01 2012-04-05 Basf Se Benzoxazinones herbicides
WO2016039404A1 (fr) * 2014-09-12 2016-03-17 公益財団法人相模中央化学研究所 Dérivé de la pyrazolinone, son procédé de fabrication et herbicide le contenant en tant que principe actif

Also Published As

Publication number Publication date
AU2001289902A1 (en) 2002-04-02
AR030779A1 (es) 2003-09-03

Similar Documents

Publication Publication Date Title
RU2251268C9 (ru) Гербицидная композиция, способ избирательной борьбы с сорными и травянистыми растениями
RU2246492C2 (ru) Промежуточные соединения для получения производных 3-гидрокси-4-арил-5-оксопиразолина с гербицидным действием
AU738222B2 (en) N-pyridonyl herbicides
RU2269537C2 (ru) Фенилзамещенные гетероциклические 1,3-кетоенолы, способ их получения, гербицидное средство на их основе и способ борьбы с ростом нежелательной растительности
WO2004035564A1 (fr) Derives de pyridine utiles comme herbicides
WO2004035563A1 (fr) Derives de 3-heterocyclylpyridine utilises comme herbicides
US20050090399A1 (en) Phenyl substituted heterocyclic compounds useful as herbicides
US20040242456A1 (en) Herbicidal n-alkysulfonamino derivatives
AU762586B2 (en) Herbicidal composition
US20020055639A1 (en) Pyrazole derivatives as herbicides
US6369002B1 (en) N-heteroaryl-substituted pyridine derivatives and their use as herbicides
US6380134B1 (en) N-pyridyl herbicide compounds
WO2002024704A1 (fr) Nouveaux herbicides
AU9344198A (en) Benzothiophene derivates as herbicides
WO2002024709A2 (fr) Nouveaux herbicides
WO1999059990A1 (fr) Derives pyridil-pyrazole, leur procede de preparation, et leur utilisation en tant qu'herbicides

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PH PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP