WO2000026194A1 - Nouveaux 1-aryl-4-thiouraciles - Google Patents

Nouveaux 1-aryl-4-thiouraciles Download PDF

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WO2000026194A1
WO2000026194A1 PCT/EP1999/008266 EP9908266W WO0026194A1 WO 2000026194 A1 WO2000026194 A1 WO 2000026194A1 EP 9908266 W EP9908266 W EP 9908266W WO 0026194 A1 WO0026194 A1 WO 0026194A1
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alkyl
alkoxy
carbonyl
methyl
halogen
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PCT/EP1999/008266
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German (de)
English (en)
Inventor
Olaf Menke
Gerhard Hamprecht
Robert Reinhard
Peter Schäfer
Cyrill Zagar
Karl-Otto Westphalen
Martina Otten
Helmut Walter
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Basf Aktiengesellschaft
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Priority to CA002349386A priority Critical patent/CA2349386A1/fr
Priority to EP99955917A priority patent/EP1127053A1/fr
Priority to JP2000579583A priority patent/JP2002528532A/ja
Publication of WO2000026194A1 publication Critical patent/WO2000026194A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/56—One oxygen atom and one sulfur atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to novel l-aryl-4-thiouracils of the formula I.
  • R 1 is hydrogen, amino or Ci-C ⁇ alkyl
  • R 2 is hydrogen, halogen, -CC alkyl or -C-haloalkyl
  • R 3 is hydrogen, halogen, Ci-C ⁇ alkyl or halomethyl
  • R 4 is hydrogen or halogen
  • R 5 cyano, halogen, -CO-NH 2 , -CS-NH 2 or -OC (R 8 , R 9 ) -CO-0 (-C-C 6 alkyl);
  • R 6 together with R 5 is a radical -N (R 7 ) -CZ 1 -C (R 8 ', R 9 ') -0- which is bonded to R 5 via the oxygen, or
  • phenyl, phenoxy or phenylsulfonyl group which may be unsubstituted or bear one to three substituents, in each case selected from the group consisting of halogen, nitro, cyano, C 1 -C 6 -alkyl,
  • Ci-C ⁇ -haloalkyl Ci-Cg-alkoxy and (C ⁇ -C 6 -alkoxy) carbonyl
  • Z 1 , Z 2 , Z 3 , Z 4 independently of one another oxygen or sulfur;
  • Ci-C ß- alkyl Ci-Cg-haloalkyl, C 3 -C 6 cycloalkyl, C 3 -Ce alkenyl, C 3 -C 6 alkynyl, hydroxy-C ⁇ -C 6 alkyl, Ci -C ⁇ -alkoxy-Ci-Ce-alkyl, C; ⁇ .
  • phenyl ring can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy and (C 1 -C 6 alkoxy) ) carbon
  • R 13 is hydrogen, hydroxyl, -CC 6 -alkyl, C 3 -C 6 -cycloalkyl, -C-C 6 -alkoxy, (Ci -Ce -alkoxy) carbonyl -Cx -C 6 -alkoxy, C 3 -C 6 - Alkenyl or C 3 -C 6 alkenyloxy;
  • R 14 , R 14 ', R 14 "independently of one another - hydrogen, halogen,
  • Phenyl- (Ci-Cg-alkyl) sulfonyloxy where the phenyl rings of the latter 10 residues may be unsubstituted or in turn may carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-C ⁇ - alkyl, Ci -C ⁇ haloalkyl,
  • R 15 is hydrogen, cyano, Ci-C ⁇ - alkyl, Ci-C ⁇ -haloalkyl,
  • R 16 is hydrogen, hydroxy, Ci-Cg-alkyl, C 3 -C ⁇ - alkenyl,
  • R 19 is hydrogen, cyano, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, (Ci-Cg-alkyl) carbonyl or (Ci-Cg-alkoxy) carbonyl;
  • R 20 is hydrogen, OR 29 , SR 29 , Ci-Cg-alkyl, which can also carry one or two Ci-Cg-alkoxy substituents, C 2 -Cg-alkenyl, C -Cg-alkynyl, Ci-Cg-haloalkyl, C 3 -Cg-cycloalkyl, Ci-C ⁇ -alkylthio-Ci-C ⁇ -alkyl, Ci-Cg-alkyliminooxy, -N (R 25 ) R 26 or phenyl, which may be unsubstituted or carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci-Cg-alkyl, C 2 -C ⁇ - alkenyl, Ci-Cg-haloalkyl, Ci-C ⁇ -alkoxy and (C ⁇ ⁇ Cg-alkoxy) carbonyl;
  • R 21 is hydrogen, cyano, halogen, Ci-C ⁇ - alkyl, C 3 -C ⁇ - alkenyl, C 3 -C 6 -alkynyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, (Ci-C ⁇ - alkyl ) - carbonyl, (Ci-C ⁇ -alkoxy) carbonyl, -N (R 25 ) R 26 or phenyl, which in turn can carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, Ci C ⁇ alkyl, Ci-C ⁇ haloalkyl, C 3 -C ⁇ alkenyl, Ci-C ⁇ alkoxy and (Ci-Cg-alkoxy) carbonyl;
  • R 22 is hydrogen, cyano, halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy,
  • Ci-Cg-haloalkyl (Ci-C ⁇ - alkyl) carbonyl or (Ci-Cg-alkoxy) carbonyl;
  • R 23 is hydrogen, cyano, Ci-Cg-alkyl or (Ci-Cg-alkoxy) carbonyl;
  • R 24 , R 29 independently of one another are hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, C -Cg-alkenyl or C -C ⁇ - alkynyl, where the latter 4 groups can each carry one or two of the following radicals: cyano , Halogen, hydroxy, hydroxycarbonyl, Ci-C ⁇ - alkoxy, Ci-Cg-alkyl-thio, (Ci-C ⁇ - alkyl) carbonyl, (C ⁇ ⁇ Cg-alkoxy) carbonyl, (Ci-Cg-alkyl) carbonyloxy, (C -Cg alkenyloxy) carbonyl or one bonded to the nitrogen atom via a carbonyl bridge those 3- to 7-membered azaheterocycle which, in addition to carbon ring members, may also contain an oxygen or sulfur atom as the ring member; or (Ci-Cg-alkyl) carbonyl, (Ci-Cg-
  • Ci -Cg alkyl aminocarbonyl Ci -Cg alkyloximino Ci -Cg alkyl, C 3 -Cg cycloalkyl,
  • R 25 , R 26 , R 27 , R 28 independently of one another are hydrogen, Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 2 -Cg-alkynyl,
  • Ci-C ⁇ haloalkyl -C-Cg-alkoxy-C ⁇ -Cg-alkyl, (Ci-Cg-alkyl) carbonyl, (Ci-Cg-alkoxy) carbonyl, (Ci-Cg- Alkoxy) - carbonyl-C -Cg-alkyl, (Ci-Cg-alkoxy) carbonyl-C 2 -Cg-alkenyl, where the alkenyl chain can additionally carry one to three halogen and / or cyano radicals, or Ci-Cg- Alkylsulfonyl, (Ci-C ⁇ - alkoxy) carbonyl-Ci-Cg-alkyl-sulfonyl, phenyl or phenylsulfonyl, where the two phenyl rings can be unsubstituted or in turn can carry one to three substituents, each selected from the group
  • Ci-Cg-haloalkyl C 3 -Cg-alkenyl, Ci-Cg-alkoxy and (Ci-Cg-alkoxy) carbonyl, or R 25 and R 26 and / or R 27 and R 28 together with the respective common nitrogen atom for a saturated or unsaturated 4- to 7-membered azaheterocycle, which besides
  • the invention also relates to the use of the compounds I as herbicides, herbicidal compositions which contain the compounds I as active substances,
  • the object of the present invention was therefore to provide new herbicidally active 1-aryluracils which can be used to combat undesirable plants better than before.
  • the l-aryl-4-thiouracils of the formula I defined at the outset were found. Furthermore, herbicidal compositions have been found which contain the compounds I and have a very good herbicidal action. In addition, processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as mixtures of enantiomers or diastereomers.
  • E / Z isomers may also be possible.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • Agriculturally useful salts include, in particular, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I. So come as cations in particular the ions of the alkali metals, preferably sodium and potassium, the alkaline earth metals, preferably calcium, magnesium and barium, and the transition metals, preferably manganese, copper, zinc and iron, as well as the airanonium ion, if desired one to four C ⁇ -C-alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (-C-alkyl) sulfonium and sulfoxonium ions, preferably tri ( -CC al
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of -C-alkanoic acids, preferably formate, acetate, propionate and butyrate.
  • organic molecule parts mentioned in the definition of R 1 to R 3 , R 5 to R 29 and on phenyl, cycloalkyl and heterocyclyl rings are collective terms for individual lists of the individual group members. All carbon chains, that is to say all (optionally substituted) alkyl -, Alkenyl or alkynyl parts can be straight-chain or branched.
  • Halogenated substituents preferably carry one to five identical or different halogen atoms.
  • Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
  • -C-C 4 alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, CH (CH 3 ) -CH 5 , 2-methylpropyl or C (CH 3 ) 3 , in particular for CH 3 , C 2 H 5 or CH (CH 3 ) 2 ;
  • C 1 -C 6 -haloalkyl for: a C 1 -C 4 -alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example CHF, CHF, CF 3 , CH 2 C1, dichloromethyl, trichloromethyl , Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2 , 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, CF 5 , 2-fluoropropyl, 3-fluoropropy
  • Ci-Cg-alkyl for: -CC 4 -alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1st , 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl,
  • Ci-Cg-haloalkyl for: Ci-Cg-alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for example, one of the radicals mentioned under C 1 -C 4 -haloalkyl or for 5- Fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6, 6, 6-trichloro-l-hexyl or dodecafluorohexyl, in particular for chloromethyl, fluoromethyl, difluoromethyl, Trifluoromethyl, 2-fluoroethyl,
  • Hydroxy-Ci-C -alkyl for: e.g. Hydroxymethyl, 2-hydroxyeth-1-yl, 2-hydroxy-prop-l-yl, 3-hydroxy-prop-l-yl, 1-hydroxy-prop-2-yl, 2-hydroxy-but-l-yl, 3-hydroxy-but-l-yl, 4-hydroxy-but-l-yl, l-hydroxy-but-2-yl, l-hydroxy-but-3-yl, 2-hydroxy-but-3-yl, 1-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methyl-prop-3-yl or 2-hydroxymethyl-prop-2-yl, in particular for 2-hydroxyethyl;
  • Cyano-Ci-Cg-alkyl for: e.g. Cyanomethyl, 1-cyanoeth-l-yl,
  • 2-cyanoeth-l-yl 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyano-prop-1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l-yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l- Cyanobut-3-yl, 2-cyano-but-3-yl, l-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2- methyl-prop-3-yl or 2-cyanomethyl-prop-2-yl, especially for cyanomethyl or 2-cyanoethyl;
  • Phenyl-Ci-C ⁇ - alkyl for: e.g. benzyl, 1-phenylethyl, 2-phenyl-ethyl, 1-phenylprop-l-yl, 2-phenylprop-l-yl, 3-phenylprop-1-yl, 1-phenylbut -l-yl, 2-phenylbut-l-yl, 3-phenylbut-l-yl, 4-phenylbut-l-yl, l-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2 -yl, 4-phenylb t-2-yl, l- (phenylmethyl) -eth-1-yl, l- (phenylmethyl) -l- (methyl) -eth-l-yl or 1- (phenylmethyl) - prop-1-yl, especially for benzyl or 2-phenylethyl;
  • Phenyl- (Ci-Cg-alkyl) carbonyloxy for: e.g. benzylcarbonyloxy, 1-phenylethylcarbonyloxy, 2-phenylethylcarbonyloxy, 1-phenylprop-1-ylcarbonyloxy, 2-phenylprop-l-ylcarbonyloxy, 3-phenylprop-1-ylcarbonyloxy , 1-phenylbut-l-ylcarbonyloxy, 2-phenylbut-1-ylcarbonyloxy, 3-phenylbut-l-ylcarbonyloxy, 4-phenyl- but-1-ylcarbonyloxy, l-phenylbut-2-ylcarbonyloxy, 2-phenylbut-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy, 4-phenylbut-2-ylcarbonyloxy, 1- (phenylmethyl) -eth- 1-ylcarbonyloxy, 1- (phenylmethyl) -1- (methyl)
  • Phenyl-Ci-Cg-alkylsulfonyloxy for: e.g. Benzylsulfonyloxy, 1-phenylethylsulfonyloxy, 2-phenylethylsulfonyloxy, 1-pheny1-prop-1-ylsulfonyloxy, 2-phenylprop-l-ylsulfonyloxy, 3-phenylprop-1-ylsulfonyloxy, 1-phenylbut-l-ylsulfonyloxy, 2-phenyl but-1-ylsulfonyloxy, 3-phenylbut-l-ylsulfonyloxy, 4-phenyl-but-1-ylsulfonyloxy, l-phenylbut-2-ylsulfonyloxy, 2-phenylbut-2-ylsulfonyloxy, 3-phenylbut-2-ylsulfonyloxy, 4-phenyl-but-2
  • - (Ci-Cg-alkyl) carbonyl for: for example CO-CH 3 , CO-C 2 H 5 , CO-CH 2 -C 2 H 5 ,
  • Ci-C-alkyl carbonyl -Ci-Cg-alkyl for: Ci-C-alkyl substituted by (Ci-Cg-alkyl) carbonyl as mentioned above, e.g. for methylcarbonylmethyl;
  • - (Ci-Cg-haloalkyl) carbonyl for: a (Ci-Cg-alkyl) carbonyl radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyl, dichloroacetyl, trichloroacetyl , Fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2, 2, 2-trif carbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2, 2-difluor
  • (C ⁇ ⁇ Cg-alkyl) carbonyloxy for: acetyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1, 1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1, 1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2, 2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentyl-methylpentoxycarbonyloxy Methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1, 1-dimethylbuty
  • (Ci-Cg-haloalkyl) carbonyloxy for: a (Ci-Cg-alkyl) carbonyloxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy , Fluoroacetyloxy, difluoroacetyloxy, trifluoroacetyloxy, chlorofluoroacetyloxy, dichlorofluoroacetyloxy, chlorodifluoroacetyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2, 2-difluoroethylcarbonyl.
  • 2-chloro-2-fluoroethylcarbonyloxy 2-chloro-2, 2-difluoroethylcarbonyloxy, 2, 2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, pentafluoroethylcarbonyloxy, 2-fluoropropylcarbonyloxy, 3- Fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy, 2, 3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3, 3, 3- Trifluoropropylcarbonyloxy, 3, 3, 3-trichloropropylcarbonyloxy, 2,2,3,3, 3-pentafluoropropylcarbonyloxy
  • (C -C ⁇ alkyl) carbonylthio for acetylthio, ethylcarbonylthio, n-propylcarbonylthio, 1-methylethylcarbonylthio, n-butylcarbonylthio, 1-methylpropylcarbonylthio, 2-methylpropylcarbonylthio, 1, 1-dimethylethylcarbonylthio, n-pentylcarbonylthio, n-pentylcarbonylthio 2-methylbutylcarbonylthio, 3-methylbutylcarbonylthio, 1, 1-dimethylpropylcarbonylthio, 1, 2-dimethylpropylcarbonylthio, 2, 2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio, n-hexylcarbonylthio, 1-methylpentylcarbonylthio - carbonylthio, 3-methylpentylcarbonylthi
  • (Ci-C ⁇ -haloalkyl) carbonylthio for: a (Ci-Cg-alkyl) carbonylthio radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetylthio, dichloroacetylthio, Trichloroacetylthio, fluoroacetylthio, difluoroacetylthio, tri- fluoroacetylthio, chlorofluoroacetylthio, dichlorofluoroacetylthio, chlorodifluoroacetylthio, 2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-bromoethylcarbonylthio, 2-iodo-ethylcarbonylthio, 2, 2-difluoroethylcarbonylthio, 2,2,2-tri-
  • (Ci-Cg-alkyl) carbamoyloxy for: methylcarbamoyloxy, ethylcarbamoyloxy, n-propylcarbamoyloxy, 1-methylethylcarbamoyloxy, n-butylcarbamoyloxy, 1-methylpropylcarbamoyloxy, 2-methylpropylcarbamoyloxy, 1, 1-dimethylethyl-pamoyloxy, pentamoyloxy, 1-Methylbutylcarbamoyloxy, 2-Methylbutylcarbamoyloxy, 3-Methylbutylcarbamoyloxy, 1, 1-Dirnethylpropylcarbamoyloxy, 1, 2-Dimethylpropylcarbamoyloxy, 2, 2-Dirnethylpropyl-carbamoyloxy, 1-Ethylpropylcarbamoyla
  • (Ci-Cg-haloalkyl) carbamoyloxy for: a (Ci-Cg-alkyl) -carbamoyloxy radical as mentioned above which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethylcarbamoyloxy, dichloromethylcarbamoyloxy , Trichloromethyl carbamoyloxy, fluoromethyl carbamoyloxy, difluoromethyl carbamoyloxy, trifluoromethyl carbamoyloxy, chlorofluoromethyl carbamoyloxy, dichlorofluoromethyl carbamoyloxy, chlorodifluoromethyl carbamoyloxy, • 2-fluoroethyl carbamoyloxy, 2-chloroethylcarbamoyloxy, 2-bromoethylcarbamoyloxy, 2-iodoethylcarbamoyloxy, 2,
  • Ci-Cg-alkoxy for: for example OCH 3 , 0C 2 H 5 , OCH 2 -C 2 H 5 , OCH (CH 3 ) 2 , n-butoxy, OCH (CH 3 ) -C 2 H 5 , OCH 2 -CH (CH 3 ) 2 , OC (CH 3 ) 3 , n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylb toxy, 1, 1-dirnethyl-propoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethyl-propoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dirnethylb toxy,
  • C ⁇ -C for 4 -haloalkoxy a C ⁇ -C 4 alkoxy as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, ie, for example chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, Difluormeth- oxy, Trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2- Chloro-2,2-difluoroethoxy, 2,2-di-chloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy
  • Ci-Cg-haloalkoxy for: a Ci-Cg-alkoxy radical as mentioned above, partially or completely by fluorine, chlorine,
  • Bromine and / or iodine is substituted, for example one of the radicals mentioned under C 1 -C 4 -haloalkoxy or for 5 -fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5 Iodine-l-pentoxy,
  • Hydroxy-Ci-Cg -alkoxy for: e.g. OCH 2 -OH, OCH (CH 3 ) -OH,
  • Cyano-Ci-Cg-alkoxy for: e.g. OCH-CN, OCH (CH 3 ) -CN, OCH 2 -CH 2 -CN, OCH (C 2 H 5 ) -OH, OCH 2 -CH (CH 3 ) -CN , 3-cyanoprop-l-yl-oxy, 1-cyanobut-l-yloxy, 2-cyanobut-l-yloxy, 3-cyanobut-l-yl-oxy, 4-cyanobut-l-yloxy, l-cyanobut-2 -yloxy, 2-cyanobut-2-yloxy, 3-cyanobut-2-yloxy, 4-cyanobut-2-yloxy, 1- (CH 2 -CN) -eth- 1-yloxy, 1- (CH 2 - CN) -1- (CH 3 ) -eth-1-yloxy or 1- (CH 2 -CN) prop-1-yloxy, in particular for OCH 2 -CN or OCH-CH 2 -CN
  • Phenyl-Ci-Cg-alkoxy for: e.g. Benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylprop-l-yloxy, 2-phenylprop-l-yloxy, 3-phenylprop-l-yloxy, 1-phenylbut-l-yloxy, 2-phenylbut-l-yl- oxy, 3-phenylb tl-yloxy, 4-phenylbut-l-yloxy, 1-phenylbut-2-yloxy, 2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy , 1- (benzyl) -eth-1-yloxy, 1- (benzyl) -1- (methyl) -eth-1-yloxy or 1- (benzyl) -prop-1-yloxy, especially for benzyloxy or 2-phenylethoxy ;
  • Heterocyclyl-Ci-Cg-alkoxy for: e.g. heterocyclylmethoxy, 1- (heterocyclyl) ethoxy, 2- (heterocyclyl) ethoxy, l- (heterocyclicl) prop-l-yloxy, 2- (heterocyclyl) prop-1-yloxy, 3- (heterocyclyl) prop-1-yloxy, 1- (heterocyclyl) but-1-yloxy, 2- (heterocyclyl) but-l-yloxy, 3- (heterocyclyl) but-1-yloxy, 4- (heterocyclyl ) but-1-yloxy, 1- (heterocyclyl) but-2-yloxy, 2- (heterocyclyl) but-2-yloxy, 3- (heterocyclyl) but-2-yloxy, 4- (hetero- cyclyl) but-2-yloxy, 1- (heterocyclylmethyl) -
  • Phenyl-Ci-Cg-alkylthio for: e.g. Benzylthio, 1-phenylethy1-thio, 2-phenylethylthio, 1-phenylprop-l-ylthio, 2-phenylprop-1-ylthio, 3-phenylprop-l-ylthio, 1-phenylbut-l-ylthio, 2-phenylbut- l-ylthio, 3-phenylbut-l-ylthio, 4-phenylbut-l-ylthio, l-phenylbut-2-ylthio, 2-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 4-phenylbut- 2-ylthio, 1- (phenylmethyl) -eth-1-ylthio, 1- (phenylmethyl) -1- (methyl) -eth-1-ylthio or 1- (phenylmethyl) prop-1-ylthio, especially for benzy
  • (Ci-Cg-alkoxy) carbonyl for: e.g. CO-OCH 3 , CO-OC 2 H 5 , CO-CH 2 -C 2 H 5 , CO-OCH (CH 3 ) 2 , n-butoxycarbonyl, CO-OCH ( CH 3 ) -C 2 H 5 , CO-OCH 2 -CH (CH 3 ) 2 , CO-OC (CH 3 ) 3 , n-pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylb toxycarbonyl , 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1 -Dimethylbutoxycarbonyl, 1, 2-
  • (Ci-C ⁇ -alkoxy) carbonyloxy for: methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylprooxycarbonyloxy, 1, 1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy , 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 2, 2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1, 1-dimethylpropoxycarbonyloxy, 1, 2-dimethylpropoxycarbonyloxyoxy, 1-methylpentoxy -Methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy, 1, 1-dimethylbutoxycarbonyloxy, 1, 2-dimethylbutoxy
  • (Ci-Cg -alkoxy) carbonylthio for: methoxycarbonylthio, ethoxycarbonylthio, n-propoxycarbonylthio, 1-methylethoxycarbonylthio, n-butoxycarbonylthio, 1-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio, 1, 1-dimethylthoxycarbonylthio, n-propoxycarbonylthio Methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio, 3-methylbutoxycarbonylthio, 2, 2-dimethylpropoxycarbonylthio, 1-ethylpropoxycarbonylthio, n-hexoxycarbonylthio, 1, 1-dimethylpropoxycarbonylthio, 1, 2-dimethylpropoxycarbonylthioyl, 1-2 Methyl-pentoxycarbonylthio, 3-methylpentoxycarbonylthio, 4-methyl-pentoxycarbonylthio, 1, 1-d
  • Ci-Cg-alkylthio for: SCH 3 , SC 2 H 5 , SCH 2 -CH 5 , SCH (CH 3 ), n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC (CH 3 ) 3 , n-pentylthio, 1-Methylb tylthio, 2-Methylbutylthio, 3-Methylbutylthio, 2, 2-Dimethylpropylthio, 1-Ethylpropylthio, n-Hexylthio, 1, 1-Dimethylpropylthio, 1, 2-Dirnethylpropylthio, 1-Methylpentylthio, 2-Methylpentylthio -Methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio,
  • Ci-Cg-haloalkylthio for: Ci-Cg-alkylthio as mentioned above, partially or completely by fluorine, chlorine,
  • Bromine and / or iodine is substituted, for example for SCHF 2 , SCF 3 , chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2, 2, 2 -Trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2, 2-di-fluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, SC 2 F 5 , 2- Fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloro propylthio, 2-bromopropylthio, 3-bromoprop
  • Ci-Cg-alkylsulfinyl for: S0-CH 3 , SO-C 2 Hs, n-propylsulfinyl, 1-methylethylsulfinyl, nB tylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, n-pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 1-methylp
  • Ci-Cg-alkylsulfonyl for: S0 2 -CH 3 , S0 2 -C 2 H 5 , n-propylsulfonyl, S0 2 -CH (CH 3 ) 2 , n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, S0 2 - C (CH 3 ) 3 , n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dirnethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyls, hexylsulfonyl, 1-ethylsulfonyl, 1-ethylsulfonyls , 1-methylpent
  • C -C 6 haloalkylsulfonyloxy for: Ci-C ⁇ - alkylsulfonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example ClCH 2 -S0 2 -0-, CH (Cl) 2 -S0 2 -0-, C (CD 3 -S0 2 -0-, FCH 2 -S0 2 -0-, CHF 2 -S0 2 -0-, CF 3 -S0-0-, chlorofluoromethyl-S0 2 - 0-, dichlorofluoromethyl-S0-0-, chlorodifluoromethyl-S0 2 -0-, 1-fluoroethyl- S0 2 -0-, 2-fluoroethyl-S0 2 -0-, 2-chloroethyl-S0 2 -0-, 2-bromoethyl-S0 2 -0-, 2-iodo-
  • (Ci-C ⁇ alkyl) aminocarbonyl for: (C 1 -C 4 alkyl) aminocarbonyl as mentioned above and, for example, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethylnetyl butyl 1, 3-dimethylbutylaminocarbonyl, 2, 2-dimethylbutylaminocarbonyl, 2, 3-diethylbutylamino
  • Di (Ci-C ⁇ -alkyl) aminocarbonyl for: for example N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-dipropylaminocarbonyl,
  • N-butyl-N-methylaminocarbonyl N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dirnethy1ethyl) -N-methylaminocarbonyl, N -Ethyl-N-propylaminocarbonyl, N-ethyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N- (1-methylpropyl) - aminocarbonyl, N-ethyl-N- (2nd -methylpropyl) aminocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) aminocarbonyl, N- (1-methyl-ethyl) -N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methyl
  • (Ci -C ⁇ - alkyl) iminooxycarbonyl for: methyliminooxycarbonyl, ethyliminooxycarbonyl, n-propyliminooxycarbonyl, 1-methyl-ethyliminooxycarbonyl, n-butyliminooxycarbonyl, 1-methyl-propyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl, 1, 1-dimethyloxycarbonyl, pentane 1-methylbutyliminooxycarbonyl, 2-methylbutyliminooxycarbonyl, 3-methylbutyliminooxycarbonyl, 1, 1-dirnethylpropyliminooxycarbonyl, 1, 2-dirnethylpropyliminooxycarbonyl, 2, 2-dimethylpropyliminooxycarbonyl, 1-ethylpropyliminooxyoxyylyl, 3-methylyloxy-methyloxycarbonyl, 3 Methylpentyliminooxycarbonyl, 4-methyl
  • Ci-C ⁇ - alkylidene aminoxy for: acetylidene aminoxy, 1-propylidene aminoxy, 2-propylidene aminoxy, 1-butylidene aminoxy, 2-tylidene aminoxy or 2-hexylidene aminoxy, in particular for acetylidene aminoxy or 2-propylidene aminoxy;
  • Ci-Cg-alkyliminooxy for: methyliminooxy, ethyliminooxy, n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy, 2-methylpropyliminooxy, n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy, 2-methylpentyloxy -Methylpentyliminooxy or 4 -Methylpentyl - iminooxy, especially for methyliminooxy, ethyliminooxy or 1 -Methylethyliminooxy;
  • Ci-Cg-alkoxy- (Ci-Cg-alkyl) aminocarbonyl for: (Ci-Cg-alkyl) - aminocarbonyl such as CO-NH-CH 3 , CO-NH-CHs, CO-NH-CH 2 -C 2 H 5 , CO-NH-CH (CH 3 ).
  • Ci-C ⁇ -alkoxyamino-Ci-C ⁇ -alkyl for: e.g. CH 2 -NH-OCH 3 , CH 2 -NH-OC 2 H 5 , CH 2 -NH-OCH 2 -C 2 H 5 , CH 2 - NH-OCH (CH 3 ) 2 , CH 2 -NH-OCH 2 -CH 2 -C 2 H 5 , CH 2 -NH-OCH (CH 3 ) -C 2 H 5 ,
  • Ci-C ⁇ -alkoxy-Ci-C ⁇ -alkylamino-Ci-C ⁇ -alkyl for: Ci-C ⁇ -alkylamino-Ci-C ⁇ -alkyl such as CH 2 -NH-CH 3 , CH 2 -NH -C 2 H 5 , CH 2 -NH-CH 2 -C 2 H 5 , CH 2 -NH-CH (CH 3 ) 2 , CH 2 -NH- (CH 2 ) 3 -CH 3 , CH 2 -NH- CH (CH 3 ) -C 2 H 5 , CH 2 -NH-CH 2 -CH (CH 3 ) 2 , CH 2 -NH-C (CH 3 ) 3 , CH 2 -NH- (CH 2 ) 4 -CH 3 ,
  • Ci-Cg-alkyloximino such as methoxyimino, ethoxyi ino, 1-propoxyimino, 2-propoxyimino, 1-methylethoxyimino, n-butoxyimino, sec.-butoxyimino, tert.
  • Ci-Cg-Alkoxy-Ci-C ⁇ - alkyl for: Ci-C ⁇ - alkoxy - as mentioned above - substituted Ci-Cg-alkyl, e.g. for CH 2 -OCH 3 , CH 2 -OCH 5 , n- Propoxymethyl, CH 2 -OCH (CH 3 ) 2 , n-butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, CH 2 -OC (CH 3 ) 3 , 2- (methoxy) ethyl, 2 - (Ethoxy) ethyl, 2- (n-propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (n-butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy ) ethyl, 2- (1,1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2-
  • Ci-C ⁇ - alkoxy-Ci-C ⁇ - alkoxy for: Ci-Cg-alkoxy substituted by Ci-Cg-alkoxy as mentioned above, for example for OCH 2 -OCH 3 , OCH 2 -OC 2 H 5 , n-propoxymethoxy, OCH 2 -OCH (CH 3 ) 2 , n-butoxymethoxy, (1-methylpropoxy) methoxy, (2-methylprooxy) methoxy, OCH -OC (CH 3 ) 3 , 2- (methoxy) ethoxy, 2- (ethoxy) ethoxy, 2- (n-propoxy) ethoxy, 2- (l-methylethoxy) ethoxy, 2- (n-butoxy) ethoxy, 2- (1-methylpropoxy) ethoxy, 2- (2- Methylpropoxy) ethoxy, 2- (1, 1-dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) prop
  • (Ci-C ⁇ - alkyl) carbonyl-Ci-Cg-alkoxy for: Ci-Cg-alkoxy substituted by (Ci-C ⁇ - alkyl) carbonyl as mentioned above, for example for OCH 2 -CO-CH 3 , OCH 2 -CO-C 2 H 5 , OCH 2 -CO-CH 2 -C 2 H 5 ,
  • Ci-Cg-alkoxy carbonyl-Ci-Cg-alkoxy for: Ci-Cg-alkoxy substituted by (Ci-Cg-alkoxy) carbonyl as mentioned above, e.g. for OCH 2 -CO-OCH 3 , 0CH 2 -CO-OC 2 H 5 , 0CH -CO-OCH 2 -C 2 H 5 , OCH 2 -CO-OCH (CH 3 ) 2 , n-butoxycarbonyl-methoxy, 1- (methoxycarbonyl) ethoxy, 2- ( Methoxycarbonyl) ethoxy, 2- (ethoxycarbonyl) ethoxy, 2- (n-propoxycarbonyl) ethoxy, 2- (n-butoxycarbonyl) ethoxy, 3- (methoxycarbonyl) ropoxy, 3- (ethoxycarbonyl) propoxy, 3 - (n-Propoxycarbonyl) propoxy, 3- (n-but
  • Ci-Cg-alkoxy carbonyl-Ci-Cg-alkyl for: Ci-Cg-alkyl substituted by (Ci-Cg-alkoxy) carbonyl as mentioned above, e.g. for methoxycarbonylmethyl, ethoxycarbonylmethyl, 1 - (methoxycarbonyl) ethyl, 2 - (methoxycarbonyl) ethyl,
  • Ci-Cg-alkoxy carbonyl as substituted Ci-Cg-alkylsulfonyl as mentioned above, e.g. for methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl, 1- (methoxycarbonyl) ethylsulfonyl, 2- (methoxycarbonyl) ethylsulfonyl, 2- (ethoxycarbonyl) ethylsulfonyl, 3 - (methoxycarbonyl) propylsulfonyl,
  • Ci-Cg-alkylthio-Ci-C ⁇ alkoxy viewed by Ci-Cg-alkylthio as mentioned above substituted C ⁇ alkoxy, eg for 0CH 2 -SCH 3, -SC 2 H 5 0CH 2, 2 0CH -SCH 2 -C 2 H 5 , 0CH 2 - SCH (CH 3 ) 2 , n-butylthiomethoxy, 0CH 2 -SCH (CH 3 ) -CH 5 , 0CH 2 -SCH 2 -CH (CH 3 ) 2 , OCH 2 -SC (CH 3 ) 3 , 2- (SCH 3 ) ethoxy, 2- (SC 2 H 5 ) ethoxy, 2- (SCH 2 -C 2 H 5 ) - ethoxy, 2- [SCH (CH 3 ) 2 1 ethoxy, 2- (n-butylthio) ethoxy, 2- [SCH (CH 3 ) -C 2 H 5 ] ethoxy
  • Ci-Cg-alkylthio- (Ci-Cg-alkyl) carbonyl for: by C ⁇ ⁇ Cg-alkyl- thio as mentioned above, preferably SCH 3 or SC 2 Hs, substituted (Ci-Cg-alkyl) carbonyl, so for example for methyl - thiomethylcarbonyl, ethylthiomethylcarbonyl, 1- (methylthio) ethylcarbonyl, 2 - (methylthio) ethylcarbonyl, 3 - (methylthio) propylcarbonyl, 4 - (methylthio) butylcarbonyl, 5 (methylthio) pentylcarbonyl or 6 - (methylthio) hexylcarbonyl, especially for CO-CH 2 -SCH 3 or CO-CH (CH 3 ) -SCH 3 ;
  • Di (Ci-Cg-alkyl) amino-Ci-Cg-alkoxy by di- (Ci-C ⁇ - alkyl) - amino such as N (CH 3 ) 2 , N (C 2 Hs) 2 , N, N-dipropylamino , N, N-di- (1-methylethyl) mino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl) amino, N [ C (CH 3 ) 3 ], N-ethyl-N-methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N - (1-methylpropyl) amino, N-methyl-N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N-methylamin
  • OCH 2 -N (CH 3 ) 2 OCH 2 -N (C 2 H 5 ) 2 , OCH (CH 3 ) -N (CH 3 ) 2 , 2- (dimethylamino) ethoxy, OCH (CH 3 ) -N (C 2 H 5 ) 2 , 3 - (dimethylamino) propoxy, 4 - (dimethylamino) butoxy, 5- (dimethylamino) pentoxy or 6- (dimethylamino) hexoxy, especially for OCH 2 -N (CH 3 ) 2 or OCH (CH 3 ) -N (CH 3 ) 2 ;
  • C 3 -C ⁇ - alkenyl for: eg prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2- en-l-yl, 2-butene-1-yl, n-penten-3-yl, n-penten-4-yl, l-methyl-but-2-en-l-yl, 2-methyl-but- 2-en-l-yl, 3-methyl-but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but-3-en-1-yl, 1, l-dimethyl-prop-2-en-l-yl, 1, 2-dimethyl-prop-2-en-1-yl, l-ethyl- prop-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-1-yl, n
  • C 2 -Cg alkenyl for: ethenyl or one of the radicals mentioned under C 3 -Cg alkenyl, in particular for ethenyl or prop-2-en-yl;
  • C 3 -Cg alkenyloxy for: prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n- Buten-3-yloxy, 1-methyl-prop-l-en-l-yloxy, 2-methyl-prop-1-en-l-yloxy, l-methyl-prop-2-en-l-yloxy, 2- Methyl-prop-2-en-l-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methyl-but- 1-en-l-yl-oxy, 2-methyl-but-l-en-l-yloxy, 3-methyl-but-l-en-l-yloxy, l-methyl-but-2-en-l- yloxy, 2-methyl-but-2-en-l
  • C 2 -Cg alkenyloxy for: ethenyloxy or one of the radicals mentioned under C 3 -Cg alkenyloxy, in particular for ethenyloxy or prop-2-en-l-yloxy;
  • C 3 -Cg haloalkenyloxy for: C -C alkenyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example 2-chloroallyloxy, 3-chloroallyloxy, 2, 3-dichloroallyloxy, 3, 3-dichloroallyloxy, 2, 3, 3-trichlorallyloxy, 2, 3-dichlorobut-2-enyloxy, 2-bromo-allyloxy, 3-bromoallyloxy, 2, 3-dibrornallyloxy, 3,3-dibromo-allyloxy, 2, 3, 3-tribromoallyloxy or 2,3-dibromobut-2-enyloxy, in particular for 2-chloroallyloxy or 3,3-dichloroallyloxy;
  • Phenyl-C 3 -Cg-alkenyloxy for: eg 3-phenyl-allyloxy, 4-phenyl-but-2-enyloxy, 4-phenyl-but-3-enyloxy or 5-phenyl-pent-4-enyloxy, preferably 3 -Phenylallyloxy or 4-phenyl-but-2-enyloxy, especially for 3 -phenylallyloxy;
  • C 3 -C ⁇ alkynyl for: prop-1-in-l-yl, prop-2-in-l-yl, n-but-1-in-l-yl, n-but-l-in-3 -yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3-yl , n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl, n Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-l-yl , n-hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-
  • - C -C ⁇ alkynyl for: ethynyl or one of the radicals mentioned under C 3 -C 6 -alkynyl, in particular for ethynyl or prop-2-yn-1-yl;
  • C 3 -Cg alkynyloxy for: prop-1-in-l-yloxy, prop-2-in-l-yloxy, n-but-1-in-l-yloxy, n-but-l-in-3- yloxy, n-but-l-in-4-yloxy, n-but-2-in-l-yloxy, n-pent-1-in-l-yloxy, n-pent-l-in-3-yloxy, n-pent-l-in-4-yloxy, n-pent-l-in-5-yloxy, n-pent-2-in-l-yl-oxy, n-pent-2-in-4-yloxy, n-pent-2-in-5-yloxy, 3-methyl-but-l-in-3-yloxy, 3-methyl-but-l-in-4-yloxy, n-hex-1-in-l- yl-oxy, n-hex-l-in-3-y
  • C 2 -Cg alkynyloxy for: ethynyloxy or one of the radicals mentioned under C 3 -Cg alkynyloxy, in particular for ethynyloxy or prop-2-yn-l-yloxy;
  • Phenyl-C 3 -Cg-alkynyloxy for: e.g. 3-phenylprop-2-in-1-yloxy, 4-phenylbut-2-in-1-yloxy, 3-phenylbut-3-in-2-yloxy, 5-phenyl pent-3-in-1-yloxy or 6-phenylhex-4-in-1-yloxy, in particular for 3-phenylprop-2-in-1-yloxy or 3-phenylbut-3-in-2-yloxy;
  • Heterocyclyl-C 3 -Cg-alkynyloxy for: e.g. 3- (heterocyclyl) prop- 2-in-l-yloxy, 4- (heterocyclyl) but-2-in-l-yloxy, 3- (heterocyclic) but- 3-in-2-yloxy, 5- (heterocyclyl) pent-3-in-l-yloxy or 6- (heterocyclyl) hex-4-in-l-yloxy, especially for 3- (heterocyclyl) prop-2-in -l-yloxy or 3- (heterocyclyl) but-3-in-2-yloxy;
  • C -C ⁇ alkynylthio for: ethynylthio or one of the radicals mentioned under C 3 -C ⁇ alkynylthio, in particular for ethynylthio or prop-2-yn-l-ylthio;
  • (C 3 -C ⁇ - alkenyloxy) carbonyl for: prop-1-en-l-yloxycarbonyl, prop-2-en-l-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-butene-2- yloxycarbonyl, n-butene-3-yloxycarbonyl, 1-methyl-prop-l-en-l-yloxycarbonyl, 2-methyl-prop-1-en-l-yloxycarbonyl, 1-methyl-prop-2-en-l- yloxycarbonyl, 2-methyl-prop-2-en-l-yloxycarbonyl, n-pentene-1-yloxycarbonyl, n-pentene-2-yloxycarbonyl, n-pentene-3-yloxycarbonyl, n-pentene-4- yloxycarbonyl, 1-methyl-but-l-en-l-yloxycarbonyl,
  • (C 3 -Cg-Alkenyloxy) carbonyl-Ci-Cg-alkyl for: by (C 3 -Cg-Alkenyloxy) carbonyl as mentioned above, preferably - Prop-2-en-l-yl-oxycarbonyl, substituted Ci-C ⁇ - alkyl, for example prop-2-en-1-yl-oxycarbonyl -methyl;
  • (C 2 -C ⁇ - alkenyl) carbonyloxy for: ethenylcarbonyloxy, prop-1-en-l-ylcarbonyloxy, prop-2-en-l-ylcarbonyloxy, 1-methyl-ethenylcarbonyloxy, n-buten-1-ylcarbonyloxy, n- Buten-2-ylcarbonyloxy, n-buten-3-ylcarbonyloxy, 1-methyl-prop-l-en-1-ylcarbonyloxy, 2-methyl-prop-1-en-l-ylcarbonyloxy, l-methyl-prop- 2-en-l-ylcarbonyloxy, 2-methyl-prop-2-en-l-yl-carbonyloxy, n-penten-1-ylcarbonyloxy, n-penten-2-ylcarbonyl-oxy, n-penten-3-ylcarbonyloxy, n-penten-4-ylcarbonyloxy,
  • (C -C ⁇ - alkenyl) carbonylthio for: ethenylcarbonylthio, prop-1-en-l-ylcarbonylthio, prop-2-en-l-ylcarbonylthio, 1-methylethenylcarbonylthio, n-buten-1-ylcarbonylthio, n-butene -2-yl-carbonylthio, n-buten-3-ylcarbonylthio, 1-methyl-prop-l-en-1-ylcarbonylthio, 2-methyl-prop-l-en-l-ylcarbonylthio, l-methyl-prop-2 -en-l-ylcarbonylthio, 2-methyl-prop-2-en-l-yl-carbonylthio, n-penten-1-ylcarbonylthio, n-penten-2-yl-carbonylthio, n-penten-3-ylcarbonylthio, n -Pentene
  • (C 2 -C 6 alkynyl) carbonyloxy for: ethynylcarbonyloxy, prop-1-in-1-ylcarbonyloxy, prop-2-in-1-ylcarbonyloxy, n-but-1-in-1-ylcarbonyloxy, n-but-1 -in-3-ylcarbonyloxy, n-but-l-in-4-ylcarbonyloxy, n-but-2-in-l-ylcarbonyloxy, n-pent-1-in-l-ylcarbonyloxy, n-pent-l-in -3-ylcarbonyloxy, n-pent-l-in-4-ylcarbonyloxy, n-pent-l-in-5-ylcarbonyloxy, n-pent-2-in-l-ylcarbonyloxy, n-pent-2-in-4 -ylcarbonyloxy, n-pent-2-in-5-ylcarbonyloxy, n-p
  • C 3 -Cg alkynylsulfonyloxy for: prop-1-in-l-ylsulfonyloxy, prop-2-in-l-ylsulfonyloxy, n-but-1-in-1-ylsulfonyloxy, n-but-l-in-3- ylsulfonyloxy, n-but-l-in-4-ylsulfonyloxy, n-but-2-in-l-ylsulfonyloxy, n-pent-1-in-l-ylsulfonyloxy, n-pent-l-in-3-ylsulfonyloxy, n-pent-l-in-4-ylsulfonyloxy, n-pent-l-in-5-ylsulfonyloxy, n-pent-2-in-1-ylsulfonyloxy, n-pent-2-in-4-ylsulfon
  • (Ci-Cg-alkoxy) carbonyl -C -Cg alkenyl for: C 2 -Cg alkenyl substituted by (Ci-Cg-alkoxy) carbonyl as mentioned above, for example for methoxycarbonyl-prop-2 -en- 1 -yl;
  • Ci-Cg-alkenyloxy for: C 3 -Cg -alkenyloxy substituted by Ci-Cg-alkoxy as mentioned above, for example for methylprop-2-en-l-yloxy;
  • C 3 -Cg-alkenyloxy-C ⁇ -Cg-alkyl for: by C 3 -Cg-alkenyloxy as mentioned above, preferably allyloxy, 2-methyl-prop-2-en-l-yloxy, but-l-en-3- yloxy, but-l-en-4-yloxy or but-2-en-l-yloxy-substituted Ci-Cg-alkyl, for example for allyloxymethyl, 2-allyloxyethyl or but-l-en-4-yloxymethyl;
  • C 3 -C alkynyloxy ⁇ -C ⁇ -C alkyl ⁇ viewed by C 3 -C 6 alkynyloxy as mentioned above, preferably propargyloxy, but-l-yn-3-yl-oxy, but-l-yn-4 -yloxy or but-2-yn-l-yloxy, substituted Ci-C ⁇ alkyl, for example for propargyloxymethyl or 2-propargyloxyethyl;
  • C -C 6 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • C 3 -Cg cycloalkyloxy for: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy;
  • C 3 -Cg cycloalkylthio for: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio;
  • C 3 -Cg cycloalkylcarbonyloxy for: cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or cyclohexylcarbonyloxy;
  • C 3 -Cg cycloalkylsulfonyloxy for: cyclopropylsulfonyloxy, cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy;
  • C 5 -C 7 cycloalkenyloxy for: cyclopent-1-enyloxy, cyclopent-2-enyloxy, cyclopent-3-enyloxy, cyclohex-1-enyloxy, cyclohex-2-enyloxy, cyclohex-3-enyloxy, cyclohept-1 - enyloxy. Cyclohept-2-enyloxy, Cyclohept-3-enyloxy or Cyclohept -4-enyloxy.
  • 3- to 7-membered azaheterocycles which in addition to carbon ring members may also contain an oxygen or sulfur atom as a ring member, are e.g.
  • saturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are:
  • unsaturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are:
  • heteroaromatics the 5- and 6-membered ones are preferred, e.g.
  • Furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as
  • 2-oxazolyl 4-oxazolyl and 5-oxazolyl
  • thiazolyl such as 2-thiazolyl
  • 4-thiazolyl and 5-thiazolyl imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1, 2, 4-oxadiazol-3-yl,
  • the variables preferably have the following meanings, in each case individually or in combination:
  • R 1 is hydrogen, amino or methyl, especially methyl
  • R 2 is hydrogen, halogen or methyl
  • R 3 is hydrogen, halogen or methyl, in particular a) hydrogen or halogen, particularly preferably hydrogen; b) hydrogen or methyl, particularly preferably methyl; c) halogen or methyl, particularly preferably halogen;
  • R 5 cyano or halogen, in particular a) cyano; b) chlorine;
  • R 6 on the one hand, together with R 5, a radical -N (R 7 ) -CO-C (R 8 ', R 9 ') -0- bonded to R 5 via oxygen;
  • Ci-Cg-alkoxy Ci-C-alkylthio, C 3 -Cg-cycloalkoxy, C 3 -Cg-cycloalkylthio, C 2 -Cg-alkenyloxy, C 2 -Cg-alkenylthio, C 2 -Cg-alkynyloxy, C 2 -Cg-alkynylthio, (Ci-Cg-alkyl) - carbonyloxy, (Ci-Cg-alkyl) carbonylthio, (C -C ⁇ - alkoxy) - carbonyloxy, (C 2 -Cg-alkenyl) carbonyloxy, (C 2 - Cg-alkenyl) - carbonylthio, (C 2 -Cg-alkynyl) carbonyloxy, (C 2 -Cg-alkynyl) - carbonylthio, Ci-Cg-alkylsulfonyloxy or Ci-
  • Halogen, nitro, cyano, hydroxyl, C 3 -Cg-cycloalkyl, Ci-Cg-alkoxy, C 3 -Cg-cycloalkoxy, C -Cg-alkenyloxy, C 3 -Cg-alkynyloxy, C ⁇ -Cg-alkoxy-C ⁇ -Cg -alkoxy, Ci-Cg-alkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg-alkyl - sulfonyl, Ci-C ⁇ -alkylidenaminoxy, oxo, N-0R 11 , the phenyl, phenoxy or phenylsulfonyl group, which are unsubstituted or can carry one to three substituents each selected from the group consisting of halogen, nitro, cyano, Ci-C ⁇ -alkyl, C ⁇ haloalkyl, C ⁇ -C 6 -al
  • R 6 in particular 2) Ci-Cg-alkoxy, C -Cg-alkenyloxy or C-Cg-alkynyloxy, where each of the latter 3 radicals can optionally carry one to three substituents, each selected from the group consisting of halogen, Ci-Cg- Alkoxy, C 3 -C ⁇ - alkenyloxy, C 3 -Cg-alkynyloxy, Ci-Cg-alkylsulfonyl, -CO-R 12 , -CO-OR 12 , -CO-N (R 12 ) R 13 , -N (R 12 ) -R 13 and
  • -C (R 14 ) N-OR 1: L ; 3) -CO-R 15, -C (NR ") -R l5, -C (R 15) (OR 17) (OR 18),
  • R 8 , R 9 , R 8 ', R 9 ' hydrogen.
  • the l-aryl-4-thiouracils of the formula I can be obtained in various ways, in particular by one of the following processes:
  • the sulfurization is usually carried out in an inert solvent or diluent, for example in an aromatic hydrocarbon such as toluene and the xylenes, in an ether such as diethyl ether, 1, 2-dimethoxyethane and tetrahydrofuran, or in an organic amine such as pyridine.
  • an inert solvent or diluent for example in an aromatic hydrocarbon such as toluene and the xylenes, in an ether such as diethyl ether, 1, 2-dimethoxyethane and tetrahydrofuran, or in an organic amine such as pyridine.
  • Phosphorus (V) sulfide and 2,4-bis (4-methoxyphenyl) -1,3,4,4-dithiadiphosphetane-2,4-dithione are particularly suitable as the sulfurization reagent.
  • the reaction temperature is normally 20 to 200 ° C, preferably 40 ° C to the boiling point of the reaction mixture.
  • the preliminary products II are known from WO 97/05117 or can be produced in an analogous manner by one of the processes described there.
  • the reaction is particularly successful when IV carries an electron-withdrawing group ortho or para to the fluorine atom.
  • a fluoroaromatic which can be converted into IV can also be used.
  • L 1 , L 2 , L 3 each represent customary hydroxyl protective groups such as methyl, ethyl, methylsulfonyl, benzyl and trimethylsilyl.
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, for example sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium -, potassium or calcium carbonate, sodium, Potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n- or iso-propanolate, n-, iso-, sec- or tert-butoxide; also basic organic nitrogen compounds, for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexy
  • the processes (B)) and (C)) according to the invention for the preparation of the compound of the formula (I) are preferably carried out in the presence of a diluent.
  • a diluent is generally suitable as diluents. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, for example pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane (chloroform) Tetrachloromethane, dialkyl ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether (MTBE), ethyl tert-butyl ether,
  • TAME pentyl ether
  • THF tetrahydrofuran
  • 1,4-dioxane 1,4-dioxane
  • ethylene glycol dimethyl ether ethylene glycol diethyl ether, diethylene glycol dimethyl ether and diethyl ether
  • Dialkyl ketones such as acetone, butanone (methyl ethyl ketone), methyl isopropyl ketone and methyl isobutyl ketone
  • Nitriles such as acetonitrile, propionitrile, butyronitrile and benzonitrile
  • Amides such as N, N-dimethylformamide (DMF), N, N-dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone and hexamethylphosphoric acid triamide
  • Esters such as methyl acetate, ethyl ester, n-propyl ester, isopropyl ester, n
  • reaction temperatures can be varied within a substantial range when carrying out processes (B)) and (C)). In general, temperatures from 0 to 200 ° C, preferably at 10 to 150 ° C, especially at 20 ° C to the boiling point of the respective reaction mixture.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess, for example up to twice the molar amount of the other component. In process A), for example, it is advisable to use the sulfurization reagent in excess.
  • the processes (A>), (B)) and (C)) are advantageously carried out at atmospheric pressure or under the autogenous pressure of the respective reaction mixture. However, it is also possible to carry out the processes under increased or reduced pressure - generally at 0.1 to 10 bar.
  • the respective reaction mixtures are generally worked up by methods known per se, for example by diluting the reaction solution with water and then isolating the product by means of filtration, crystallization or solvent extraction, or by removing the solvent, and distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase on the product.
  • the l-aryl-4-thiouracile I can be prepared by one of the synthesis methods mentioned above.
  • the l-aryl-4-thiouracils I can be obtained in the preparation as isomer mixtures, which, however, can, if desired, be separated into the pure isomers by the customary methods such as crystallization or chromatography, including on an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting products.
  • Agricultural salts of the compounds I can be formed by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reaction with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • Salts of I can also be prepared in a conventional manner by salting the corresponding alkali metal salt, as can ammonium, phosphonium, sulfonium and sulfoxonium salts using ammonia, phosphonium, sulfonium or sulfoxonium hydroxides.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, maize, soybeans and cotton, they work against weeds and grass weeds without causing any significant damage to crops. This effect occurs especially at low application rates.
  • the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarle, Seeale Solanum tuberosum, Sorghum bicolor (S. vulgäre), Theobroma cacao, Tri- folium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea ays.
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions of medium to high boiling point such as
  • Kerosene and diesel oil also coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • Paraffins etrahydronaphthalene
  • alkylated naphthalenes and their derivatives alkylated benzenes and their derivatives
  • alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol
  • ketones such as cyclohexanone
  • strongly polar solvents e.g.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the l-aryl-4-thiouracile I as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols and of fatty alcohol glycol ether, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl poly
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coating, impregnation and homogeneous granules 15 can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate , Ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied within a wide range.
  • the formulations contain about 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are in a purity of
  • the active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.
  • the l-aryl-4-thiouracile I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
  • test plants For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the application rate for the post-emergence application was only 31.3 and 15.6 g / ha a.s.
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • Table 2 shows the superior herbicidal activity of the compound No. Ib.3 in comparison to the comparative compound A known from WO 97/05117 (Example 3 there)

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Abstract

L'invention concerne de nouveaux 1-aryl-4-thiouraciles de formule (I), leur sels/énoléther, servant d'herbicides. Dans la formule, R<1> = H, NH2, alkyle C1-C6; R<2> = H, halogène, alkyle C1-C4, halogénure d'alkyle C1-C4; R<3> = H, halogène, alkyle C1-C6, halogénure de méthyle; R<4> = H, halogène; R<5> = CN, halogène, -CO-NH2, -CS-NH2, -OC(R<8>,R<9>)-CO-O(alkyle C1-C6); Y = N, CH ou conjointement avec R<6> représentent un pont >C-O-C(R<10>)=N-; R<6> conjointement avec R<5> = un radical -N(R<7>)-C(O/S)-C(R<8'>,R<9'>)-O- lié à R<5> par l'intermédiaire de l'oxygène, ou 1) H, OH, SH, CN, NO2, halogène, alkyle C1-C6, halogénure d'alkyle C1-C6, halogénure d'alcoxy C1-C6, halogénure d'alkylthio C1-C6, alkylthio C1-C6(C1-C6-alkyl)carbonyle, (alkyl C1-C6)imino-oxycarbonyle, alcoxy C1-C6 alkyle C1-C6, alcoxyamino C1-C6 alkyle C1-C6, alcoxy C1-C6 alkylamino C1-C6 alkyle C1-C6, 2) l'un des radicaux suivants éventuellement substitués: alcoxy C1-C6, alkylthio C1-C6, cycloalcoxy C3-C6, cycloalkylthio C3-C6, alcényloxy C2-C6, alcénylthio C2-C6, alcynyloxy C2-C6, alcynylthio C2-C6, (alkyl C1-C6)carbonyloxy, (alkyl C1-C6)carbonylthio, (alcoxy C1-C6)carbonyloxy, (alcényl C2-C6)carbonyloxy, (alcényl C2-C6)carbonylthio, (alcynyl C2-C6)carbonyloxy, (alcynyl C2-C6)carbonylthio, alkyl C1-C6 sulfonyloxy ou alkyl C1-C6 sulfonyl, 3) 28 autres radicaux; R<7> = H, l'un des radicaux suivants éventuellement substitués: alkyle C1-C6, alcényl C3-C6, alcynyl C3-C6, alcoxy C1-C6, alcényl C3-C6 oxy, alcynyl C3-C6 oxy, cycloalkyle C3-C6 ou cycloalcoxy C3-C6; R<8>, R<9>, R<8'>, R<9'> = H, CN, alkyle C1-C6; R<10> = H, halogène, l'un des radicaux suivants éventuellement substitués : alkyle C1-C6, alcényle C3-C6, alcynyle C3-C6, alcoxy C1-C6, alcényloxy C3-C6, alcynyloxy C3-C6, cycloalkyle C3-C6 ou cycloalcoxy C3-C6.
PCT/EP1999/008266 1998-11-02 1999-10-29 Nouveaux 1-aryl-4-thiouraciles WO2000026194A1 (fr)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014202505A1 (fr) 2013-06-20 2014-12-24 Bayer Cropscience Ag Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
WO2014202510A1 (fr) 2013-06-20 2014-12-24 Bayer Cropscience Ag Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
WO2015004028A1 (fr) 2013-07-08 2015-01-15 Bayer Cropscience Ag Dérivés de sulfures et sulfoxydes d'aryles hexacycliques à liaison c‑n utilisés comme pesticides
WO2016091857A1 (fr) 2014-12-11 2016-06-16 Bayer Cropscience Aktiengesellschaft Dérivés de sulfure d'aryle et d'oxyde arylsulfonique à liaison c-n, à cinq chaînons, utilisés comme pesticides

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996008477A1 (fr) * 1994-09-15 1996-03-21 Uniroyal Chemical Company, Inc. 3-arylthionouraciles utilises comme herbicides, defoliants et deshydratants
DE19508590A1 (de) * 1995-03-13 1996-09-19 Basf Ag 3-Aryluracile und Zwischenprodukte zu deren Herstellung
WO1998042681A1 (fr) * 1997-03-25 1998-10-01 Basf Aktiengesellschaft Nouveaux derives herbicides d'acide hydroximique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996008477A1 (fr) * 1994-09-15 1996-03-21 Uniroyal Chemical Company, Inc. 3-arylthionouraciles utilises comme herbicides, defoliants et deshydratants
DE19508590A1 (de) * 1995-03-13 1996-09-19 Basf Ag 3-Aryluracile und Zwischenprodukte zu deren Herstellung
WO1998042681A1 (fr) * 1997-03-25 1998-10-01 Basf Aktiengesellschaft Nouveaux derives herbicides d'acide hydroximique

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014202505A1 (fr) 2013-06-20 2014-12-24 Bayer Cropscience Ag Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
WO2014202510A1 (fr) 2013-06-20 2014-12-24 Bayer Cropscience Ag Dérivés d'arylsulfure et d'arylsulfoxyde utilisés comme acaricides et insecticides
WO2015004028A1 (fr) 2013-07-08 2015-01-15 Bayer Cropscience Ag Dérivés de sulfures et sulfoxydes d'aryles hexacycliques à liaison c‑n utilisés comme pesticides
CN105517995A (zh) * 2013-07-08 2016-04-20 拜耳作物科学股份公司 作为杀虫剂的六元c-n键合的芳基硫化物和芳基硫氧化物衍生物
CN105517995B (zh) * 2013-07-08 2018-10-02 拜耳作物科学股份公司 作为农药的六元c-n键合的芳基硫化物和芳基硫氧化物衍生物
WO2016091857A1 (fr) 2014-12-11 2016-06-16 Bayer Cropscience Aktiengesellschaft Dérivés de sulfure d'aryle et d'oxyde arylsulfonique à liaison c-n, à cinq chaînons, utilisés comme pesticides

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