EP1218350A1 - Derives de 1-aryle-1,3-dihydro-imidazole-2-(thi)ones, fabrication, et utilisation en tant qu'herbicides ou pour la dessiccation/defoliation de plantes - Google Patents

Derives de 1-aryle-1,3-dihydro-imidazole-2-(thi)ones, fabrication, et utilisation en tant qu'herbicides ou pour la dessiccation/defoliation de plantes

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Publication number
EP1218350A1
EP1218350A1 EP00967704A EP00967704A EP1218350A1 EP 1218350 A1 EP1218350 A1 EP 1218350A1 EP 00967704 A EP00967704 A EP 00967704A EP 00967704 A EP00967704 A EP 00967704A EP 1218350 A1 EP1218350 A1 EP 1218350A1
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EP
European Patent Office
Prior art keywords
alkyl
alkoxy
carbonyl
haloalkyl
cyano
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EP00967704A
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German (de)
English (en)
Inventor
Olaf Menke
Robert Reinhard
Gerhard Hamprecht
Michael Puhl
Ingo Sagasser
Cyrill Zagar
Martina Otten
Karl-Otto Westphalen
Helmut Walter
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BASF SE
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BASF SE
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Publication of EP1218350A1 publication Critical patent/EP1218350A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/70—One oxygen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
    • 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 substituted 1-aryl-1,3-di-hydroimidazole-2 - (thi) ones of the formula I.
  • R 1 amino, -CC 6 alkyl or Ci-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-H 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
  • Ci-C ö -haloalkyl Ci-C ⁇ -haloalkoxy, C ⁇ -C 6 -haloalkylthio, C_-C 6 -alkylthio- (C ⁇ -C 6 -alkyl) carbonyl, (Ci-C ö -alkyl) iminooxycarbonyl, C ⁇ -C 6 -alkoxy- C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxyamino-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alk-oxy-Ci-C 6 -alkylamino-Ci -C 6 - alky1 .
  • Halogen nitro, cyano, hydroxy, C 3 -C 6 cycloalkyl, C ⁇ -C 6 alkoxy, C 3 -C 6 cycloalkyloxy, C 3 -C 6 "alkenyloxy, C 3 -C 6 alkynyloxy, C ⁇ -C6 -Alkoxy-C 6 -C 6 -alkoxy,
  • Z 1 , Z 2 , Z 3 , Z 4 independently of one another oxygen or sulfur;
  • R 8 , R 9 , R 8 ', R 9 ' independently of one another are hydrogen, cyano or
  • R 11 , R 11 ', R 11 "independently of one another are hydrogen, Ci-C ⁇ -alkyl, Ci-C ⁇ -haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 - Alkynyl, hydroxy -CC 6 alkyl, -C 6 alkoxy -C 6 alkyl, -C 6 alkylthio -CC 6 -alkyl, cyano -CC 6 -alkyl, (Ci -C ⁇ - alkyl) carbonyl -CC 6 -alkyl, (Ci-C ⁇ - alkoxy) carbonyl-Ci-C ⁇ -alkyl, (C ! -C 6 -alkoxy) carbonyl - C 2 -C 6 -alkenyl, (-C-C 6 alkyl) carbonyloxy-Ci-Ce-alkyl or
  • Phenyl-C 1 -C 6 -alkyl where the phenyl ring can, if desired, carry one to three substituents, each selected from the group consisting of cyano, nitro, halogen, C ⁇ -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy and (Ci-C ⁇ -alkoxy) carbonyl;
  • R 13 is hydrogen, hydroxy, -CC 6 -alkyl, C 3 -C 6 -cycloalkyl, -C-C 6 -alkoxy, (-C-C 6 -alkoxy) carbonyl-Ci-C ⁇ -alkoxy, C 3 -C 6 - Alkenyl or C 3 -C 6 alkenyloxy;
  • R 15 is hydrogen, cyano, Ci-C ⁇ -alkyl, C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C ⁇ -C6 alk - oxy-Ci-C ß- alkyl or (-C-C 6 alkoxy) carbonyl;
  • R 16 is hydrogen, hydroxy, Cx-C ⁇ alkyl, C 3 -C 6 alkenyl, C 3 -C 6 -
  • R 19 is hydrogen, cyano, halo, C ⁇ -C 6 -alkyl, C 6 haloalkyl, Ci-Ce-alkoxy, (C ⁇ -C6 alkyl) carbonyl or (C ⁇ -C6 alkoxy) - carbonyl;
  • R 20 is hydrogen, OR 29 , SR 29 , -C -C 6 alkyl, which can also carry one or two -C -C 6 alkoxy substituents, C 2 -C. 6 -alkenyl, C -C 6 -alkynyl, -C-C 6 -haloalkyl, C 3 -C 6 -cycloalkyl, C ⁇ -C 6 -alkylthio-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -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-C ⁇ -alkyl, C 2 -C 6 alkenyl, Ci-C ⁇ - Haloalkyl, -CC 6 alkoxy and (-C 6 -alkoxy) carbonyl;
  • R 21 is hydrogen, cyano, halogen, Ci-C ⁇ -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, -C-C 6 -alkoxy-C ⁇ -C 6 -alkyl, (-C ⁇ -C 6 - 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, C l -C 6 -alkyl, C 6 haloalkyl, C 3 -C 6 alkenyl, C ⁇ -C 6 -alkoxy and (C ⁇ -C 6 -alkoxy) carbonyl;
  • R 22 is hydrogen, cyano, halogen, Ci-C ⁇ - alkyl, Ci-C ⁇ -alkoxy,
  • R 23 is hydrogen, cyano, Ci-C ⁇ -alkyl or (-C-C 6 alkoxy) carbonyl;
  • R 25 , R 26 , R 27 , R 28 independently of one another
  • Ci-C ⁇ -alkyl C 3 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C6 cycloalkyl, Ci-C ⁇ -haloalkyl, C ⁇ -C 6 alkoxy-C ⁇ -C 6 alkyl , (-C 6 alkyl) carbonyl, (-C 6 alkoxy) carbonyl, (-C 6 alkoxy) - carbonyl -C 6 alkyl, (-C 6 alkoxy) carbonyl-C 2 -C 6 -alkenyl, where the alkenyl chain can additionally carry one to three halogen and / or cyano radicals, or -CC 6 alkylsulfonyl, (-C 6 -alkoxy) carbonyl -C -C 6 -alkyl- sulfonyl, phenyl or phenylsulfonyl, where the two phenyl rings can be unsubstituted
  • the invention also relates to herbicidal compositions and compositions for the desiccation / defoliation of plants which comprise the compounds I as active substances,
  • the object of the present invention was to provide new herbicidally active compounds which can be used to combat undesirable plants better than before.
  • substituted 1-aryl-1,3-dihydro-imidazole-2 - (thi) ones 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 I are also suitable for the desiccation / defoliation of parts of plants, for which crop plants such as cotton, potato, rapeseed, sunflower, soybean or field beans, in particular cotton, are suitable.
  • crops plants such as cotton, potato, rapeseed, sunflower, soybean or field beans, in particular cotton
  • agents for the desiccation / defoliation of plants, methods for producing these agents and methods for the desiccation / defoliation of plants with 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 or desiccant / defoliant action of the compounds I.
  • 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 ammonium ion, if desired one to four C ⁇ -C 4 alkyl substituents and / or a phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C ⁇ -C 4 -alkyl) sulfonium and sulfoxonium
  • 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 represent collective terms for individual lists of the individual group members. All carbon chains, ie 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 haloalkyl for: a -CC 4 alkyl radical such as CH 3 , CH 5 / CH 2 -C 2 H 5 , CH (CH 3 ) 2 , nC 4 H 9 , CH (CH 3 ) -C 2 H 5 , CH 2 -CH (CH 3 ) and C (CH 3 ) 3 , in particular CH 3 , C 2 H 5 or CH (CH 3 ) 2 , which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine is, for example, CH 2 F, CHF 2 , CF 3 , CH 2 C1, CH (C1) 2 , C (C1) 3 , chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2, 2, 2-triflu
  • 2-fluoroethyl 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) - 2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or CF 2 -CF 2 -C 2 F 5 , especially for CH 2 F, CHF 2 , CF 3 , CH 2 C1, 2-fluoroethyl, 2-chloroethyl or 2, 2, 2-trifluoroethyl;
  • Ci-Ce-alkyl for: for example CH 3 , C 2 H 5 , CH -C 2 H 5 , CH (CH 3 ) 2 , nC 4 H 9 , CH (CH 3 ) -C 2 H 5 , CH 2 - CH (CH 3 ), C (CH 3 ) 3 , nC 5 Hn, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, nC 6 H ⁇ 3 , 1, 1- Dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2- Dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethyl butyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-tri
  • - Hydroxy-C ⁇ -C 6 -alkyl for: eg hydroxymethyl, 2-hydroxyeth-l-yl, 2-hydroxyprop-l-yl, 3-hydroxyprop-l-yl, l-hydroxyprop-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, l-hydroxy-2-methyl-prop-3-yl, 2-hydroxy-2-methyl-prop-3-yl or 2-hydroxymethyl-prop-2-yl, especially for 2-hydroxyethyl;
  • Cyano-C ⁇ -C 6 alkyl for: for example 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-
  • Phenyl-C 6 -C 6 alkyl for: for example benzyl, 1-phenylethyl, 2-phenylethyl, 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-phenylbut-2-yl, 1- (phenylmethyl) -eth-1-yl, 1- (phenylmethyl) -1- (methyl) -eth-l-yl or 1- (phenylmethyl) prop -1-yl, especially for benzyl or 2-phenylethyl;
  • Phenyl- (-CC 6 -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-phenylbut-1-ylcarbonyloxy, l-phenylbut-2-ylcarbonyloxy, 2-phenyl- but-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy, 4-phenyl-but-2-ylcarbonyloxy, 1- (phenylmethyl) -eth-1-ylcarbonyloxy, 1- (phenylmethyl) -1- (methyl)
  • Phenyl -C_ - C alkylsulfonyloxy for: e.g. benzenesulfonyloxy
  • (-C-C 6 alkyl) carbonyl for: C0-CH 3 , C0-CH 5 ,, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1, 1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1, 1-dimethylpropylcarbonyl,
  • Ci-C 6 alkyl carbonyl -C-C 6 alkyl for: Ci-C 6 alkyl substituted by (Ci-C 6 alkyl) carbonyl as mentioned above, for example for methylcarbonylmethyl;
  • (-C-C 6 -Halogenalkyl) carbonyl for: a (Ci-C ⁇ -alkyl) carbonyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoroacetyl, difluoroacetyl, trifluoroacetyl , Chloroacetyl, dichloroacetyl, trichloroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl,
  • (-C-C 6 alkyl) carbonyloxy for: acetyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1, 1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy - oxy , 1-Methylbutylcarbonyloxy, 2-Methylbutylcarbonyloxy, 3-Methylbutylcarbonyloxy, 1, 1-Dimethylpropylcarbonyloxy, 1, 2-Dimethylpropylcarbonyloxy, 2, 2-Dimethylpropylcarbonyloxy, 1-Ethylpropylcarbonyloxy, n-Hexylcarbonyloxy, 1-Methylpentyl-methylylylylcarbonyloxy -Methylpentylcarbonyloxy,
  • (-C-C 6 -Halogenalkyl) carbonyloxy for: a (Ci-C ⁇ -alkyl) - carbonyloxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 0-CO- CH 2 F, 0-CO-CHF 2 , 0-CO-CF 3 , 0-CO-CH 2 Cl, 0-CO-CH (Cl) 2 , 0-C0-C (Cl) 3 , chlorofluoroacetyloxy, dichlorofluoro- acetyloxy, chlorodifluoroacetyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2, 2-difluoroethylcarbonyloxy, 2, 2, 2-trifluoroethylcarbonyloxy, 2-
  • (-CC 6 alkyl) carbonyloxy -C 6 alkyl for: Ci (C 6 alkyl) carbonyloxy substituted by (-C 6 alkyl) as mentioned above, for example for methylcarbonyloxymethyl, ethylcarbonyloxymethyl,
  • (-CC 6 -haloalkyl) carbonylthio for: a (Ci-C ⁇ -alkyl) - carbonylthio radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example S-CO- CH 2 F, S-CO-CHF 2 , S-CO-CF 3 , S-C0-CH 2 C1,
  • (Ci-C ß- alkyl) carbamoyloxy for: methylcarbamoyloxy, ethylcarb- a oyloxy, n-propylcarbamoyloxy, 1-methylethylcarbamoyloxy, n-butylcarbamoyloxy, 1-methylpropylcarbamoyloxy, 2-methylpropylcarbamoyloxy, 1, 1-dimethylethylcarbamoyloxy carbamoyloxy, 1-methylbutylcarbamoyloxy, 2-methylbutylcarbamoyloxy, 3-methylbutylcarbamoyloxy, 1, 1-dimethylpropylcarbamoyloxy, 1, 2-dimethylpropylcarbamoyloxy, 2, 2-dimethylpropylcarbamoyloxy, 1-ethylloxamoyloxamyloxyamyloxyamyloxyamyloxyamyloxy
  • (-C 6 -Halogenalkyl) carbamoyloxy for: a (-C 6 alkyl) - carbamoyloxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloromethylcarbamoyloxy, dichloromethylcarba - moyloxy, Trichlormethylcarbamoyloxy, Fluormethylcarbamoyloxy, Difluormethylcarbamoyloxy, Trifluormethylcarbamoyloxy, Chlorfluormethylcarbamoyloxy, Dichlorfluormethylcarbamoyloxy, Chlordifluormethylcarbamoyloxy, 2-Fluorethylcarbamoyloxy, 2-Chlorethylcarbamoyloxy, 2-Bro ethylcarbamoyloxy, 2-iodoethyl carbamoyloxy, 2, 2-Difluore
  • Ci-Ce-alkoxy for: for example OCH 3 , 0C 2 H 5 , 0CH 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-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy , 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2 , 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,
  • 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 OCH 2 F, OCHF 2, OCF 3, 2 0CH C1, 0CH (C1), 0C (C1) 3 , chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2,2,2 Tri-fluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2, 2-dichloro-2-fluoroethoxy, 2, 2, 2-trichloroethoxy, 0C 2 F 5 , 2-fluoropropoxy, 3-fluoropropoxy,
  • Ci-C ⁇ -haloalkoxy for: a Ci-C ß -alkoxy radical as mentioned above, partially or completely by fluorine, chlorine,
  • Bromine and / or iodine is substituted, that is, 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 -CC-C 6 -alkoxy for: for example OCH 2 -OH, OCH (CH 3 ) -OH, OCH 2 -CH 2 -OH, OCH (C 2 H 5 ) -OH, OCH 2 -CH (CH 3 ) -OH, 3-hydroxyprop-l-yloxy, 1-hydroxybut-l-yloxy, 2-hydroxybut-l-yloxy, 3-hydroxybut-1-yloxy, 4-hydroxybut-l-yloxy, l- Hydroxybut-2-yloxy, 2-hydroxybut-2-yloxy, 3-hydroxybut-2-yloxy, 4-hydroxybut-2-yl - oxy, l- (CH 2 -OH) -eth-l-yloxy, 1- ( CH 2 -OH) -1- (CH 3 ) -eth-1-yloxy or 1- (CH 2 -OH) -prop-1-yloxy, in particular for OCH 2 -OH or OCH 2 -CH 2 -OH;
  • Cyano-C ⁇ -C 6 alkoxy for: for example OCH 2 -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-yloxy, 1-cyano-but-1-yloxy, 2-cyanobut-l-yloxy, 3-cyanobut-l-yloxy, 4-cyano-but-1-yloxy, l- Cyanobut-2-yloxy, 2-cyanobut-2-yloxy, 3-cyano-but-2-yloxy, 4-cyanobut-2-yloxy, 1- (CH 2 -CN) -eth-1-yloxy, l- ( CH 2 -CN) -l- (CH 3 ) -eth-l-yloxy or 1- (CH 2 -CN) prop-1-yloxy, in particular for OCH 2 -CN or OCH 2 -CH 2 -
  • Phenyl -C ⁇ -C 6 -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-yloxy, 3-phenylbut-l-yloxy, 4-phenylbut-l-yloxy, 1-phenylbut-2-yloxy, 2-phenylbut-2-yloxy, 3-phenylbut-2 -yloxy, 4-phenyl-but-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-C ⁇ - alkoxy for: for example heterocyclylmethoxy
  • Phenyl -C ⁇ -C 6 alkylthio for: eg benzylthio, 1-phenylethylthio, 2-phenylethylthio, 1-phenylprop-l-ylthio, 2-phenylprop-l-ylthio, 3-phenylprop-l-ylthio, 1-phenylbut -l-ylthio, 2-phenylbut-1-ylthio, 3-phenylbut-l-ylthio, 4-phenylbut-l-ylthio, l-phenylbut-2-ylthio, 2-phenylbut-2-ylthio, 3-phenylbut -2-yl-thio, 4-phenylbut-2-ylthio, 1- (phenylmethyl) -eth-1-ylthio, 1- (phenylmethyl) -1- (methyl) -eth-1-ylthio or 1- (phenylmethyl) prop-1-ylthio, especially for benzyl
  • - (-C-C 6 alkoxy) carbonyl for: for example 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-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1- Dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbon
  • (-C-C 6 -alkoxy) carbonyloxy for: O-CO-OCH 3 , 0-CO-OC 2 H 5 , 0-CO-OCH 2 -C 2 H 5 , 0-CO-OCH (CH 3 ) 2 , n-butoxycarbonyloxy, 1-methyl-propoxycarbonyloxy, 2-methylpropoxycarbonyloxy, O-CO-OC (CH 3 ) 3 , 0-CO-0 (nC 5 Hu), 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy , 2, 2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, O-CO-O (nC 6 H ⁇ 3 ), 1, 1-dimethylpropoxycarbonyloxy, 1, 2-dimethylpropoxycarbonyloxy, 1-methylpentoxycarbonyloxy, 2-methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy , 4-methylpentoxycarbonyloxy,
  • -C-C-haloalkylthio for: -C-C-alkylthio such as SCH 3 , SCH 5 ,
  • SCH 2 -C 2 H 5 SCH (CH 3 ) 2 , S (nC 4 H 9 ), SCH (CH 3 ) -C 2 H 5 , SCH 2 -CH (CH 3 ) 2 and SC (CH 3 ) 3 which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example for SCH 2 F, SCHF 2 , SCF 3 , SCH 2 C1, SCH (CD 2 , SC (C1) 3 , chlorodifluoromethylthio, bromine difluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2, 2, 2-trichloroethylthio, 2-chloro-2- fluoroethylthio, 2-chlor
  • Ci-C ⁇ -haloalkylthio for: -CC 6 -alkylthio as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example one of the under C ⁇ -C 4 -haloalkylthio called residues, or 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undeca- fluoropentylthio, 6-fluorohexylthio or 6-chlorohexylthio, especially for SCH 2 F, SCHF 2 , SCF 3 , SCH 2 C1, 2-fluoroethylthio, 2-chloroethylthio or 2, 2, 2-trifluoroethylthio;
  • -C-C-Haloalkylsulfinyl for: -C-C 4 alkylsulfinyl such as SO-CH 3 , SO-C 2 H5, SO-CH 2 -C 2 H 5 , SO-CH (CH 3 ) 2 , SO- (nC 4 H 9 ), SO-CH (CH 3 ) -C 2 H 5 , SO-CH 2 -CH (CH 3 ) 2 and SO-C (CH 3 ) 3 , partially or completely by fluorine, chlorine, bromine and / or Iodine is substituted, e.g.
  • -C 1 -C 4 haloalkylsulfonyl for: -C 1 -C 4 alkylsulfonyl such as S0 2 -CH 3 , SO 2 -C 2 H 5 , S0 2 -CH 2 -C 2 H 5 , S0 2 -CH (CH 3 ) 2 , S0 2 - (nC 4 H 9 ), S0 2 -CH (CH 3 ) -CH 5 , S0 2 -CH 2 -CH (CH 3 ) 2 and S0 2 -C (CH 3 ) 3 , which is partially or completely by Fluorine, chlorine, bromine and / or iodine is substituted, for example for S0 2 -CH 2 F, S0 2 -CHF 2 , S0 2 -CF 3 , S0 2 -CH 2 C1, S0 2 -CH (C1) 2 , S0 2 -C (C1) 3 , chlorodifluoromethylsulfony
  • 2-ethylbutylsulfonyloxy 1, 1, 2-trimethylpropylsulfonyloxy, 1,2, 2-trimethylpropylsulfonyloxy, 1-ethyl-l-methylpropyl - sulfonyloxy or l-ethyl-2-methylpropylsulfonyloxy, especially for methylsulfonyloxy;
  • Ci-C ⁇ -alkylsulfonyloxy for: Ci-C ⁇ -alkylsulfonyloxy as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example FCH 2 -S0 2 -0-, CHF 2 -S0 2 -0-, CF 3 -S0 2 -0-, ClCH 2 -S0 2 -0-, CH (Cl) 2 -S0 2 -0-, C (Cl) 3 -S0 2 -0-, chlorofluoromethyl-S0 2 -0-, dichlorofluoromethyl-S0 2 -0-, chlorodifluoromethyl-S0 2 -0-, 1-fluoroethyl-S0-0-, 2-fluoroethyl-S0 2 -0-, 2-chloroethyl-S0 2 - 0-, 2-bromoethyl-S0 2 -0-,
  • (C ⁇ -C 6 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, 4 Dimethylbutyl - aminocarbonyl, 1, 2-dimethylbutylaminocarbonyl, 1, 3-dimethylbutylaminocarbonyl, 2, 2-dimethylbutylaminocarbony
  • N- (1-methylethyl) aminocarbonyl N- (1-methylethyl) -N- (1-methylpropyl) aminocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) aminocarbonyl, N- (1 , 1-dimethylethyl) -N- (1-methylethyl) aminocarbonyl, N-butyl-N- (1-methylpropyl) aminocarbonyl, N-butyl-N- (2-methylpropyl) aminocarbonyl, N-butyl-N- (1, 1-dimethyl-ethyl) aminocarbonyl, N- (1-methylpropyl) -N- (2-methylpropyl) - aminocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) aminocarbonyl or N- ( 1, 1-dimethylethyl) -N- (2-methylpropyl) minocarbonyl, especially for C0-N (
  • (C ⁇ -C 6 -alkyl) iminooxycarbonyl for: methyliminooxycarbonyl, ethyliminooxycarbonyl, n-propyliminooxycarbonyl, 1-methyl-ethyliminooxycarbonyl, n-butyliminooxycarbonyl, 1-methylpropyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl, 1, 1-dimethyloxyinoylyl -Methylbutyliminooxycarbonyl, 2-Methylbutyliminooxycarbonyl, 3-Methylbutyliminooxycarbonyl, 1, 1-Dimethylpropyliminooxycarbonyl, 1, 2-Dirnethylpropyliminooxycarbonyl, 2, 2-Dimethyl - propyliminooxycarbonyl, 1-Ethylpropyliminooxyoxyylyl, 2-Methyloxycarbonyl, 2-Methyloxycarbonyl, 2-Meth
  • Ci-C ⁇ - alkyliminooxy for: methyliminooxy, ethyliminooxy, n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy, 2-methylpropyliminooxy, n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy, 2 -M pentyliminooxy, 3-methylpentyliminooxy or 4-methylpentyliminooxy, especially for methyliminooxy, ethyliminooxy or 1-methylethyliminooxy;
  • Ci-C ⁇ -alkoxy- (Ci-C ⁇ -alkyl) aminocarbonyl for: (Ci-C ⁇ -alkyl) - aminocarbonyl such as C0-NH-CH 3 , C0-NH-C 2 H 5 , C0-NH-CH- C 2 H 5 ,
  • - C 6 -C 6 alkoxyamino -C 6 C 6 alkyl for: for example 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 ,
  • -CC 6 alkoxy -CC 6 -alkylamino -C 6 -alkyl for: -C 6 -alkylamino -C 6 -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-CH3, ( 1-methylbutylamino) methyl, (2-methylbutylamino) methyl, (3-methylbutylamino) methyl, (2, 2-dimethylpropylamino) methyl, (1-ethylpropylamino)
  • Ci-C ⁇ alkoxyimino such as methoxyimino, ethoxyimino, 1-propoxyimino, 2-propoxyimino,
  • C 1 -C 6 -alkoxy-C 6 -C 6 -alkoxy for: C 1 -C 6 -alkoxy substituted as mentioned above -CC 6 -alkoxy, for example for OCH 2 -OCH 3 , OCH 2 -OC 2 H 5 , OCH 2 -0 (C 3 H 7 ), OCH 2 -OCH (CH 3 ) 2 , OCH 2 -0 (nC 4 H 9 ), OCH 2 -OCH (CH 3 ) -C 2 H 5 , 0CH 2 -OCH 2 -CH (CH 3 ), OCH 2 -OC (CH 3 ) 3 , 2- (methoxy) ethoxy, 2- (ethoxy) ethoxy, 2- (n-propoxy) ethoxy, 2- (1-methylethoxy) ethoxy, 2- (n-butoxy) ethoxy, 2- (l-methylpropoxy) ethoxy, 2- (2-methylpropoxy) ethoxy, 2- (1
  • (-C-C 6 -alkoxy) carbonyl-C ⁇ -C 6 -alkoxy for: Ci-C ⁇ - alkoxy substituted by (C ⁇ -C 6 -alkoxy) carbonyl as mentioned above, for example for OCH 2 -CO-OCH 3 , OCH 2 -CO-OC 2 H 5 , OCH 2 -CO-OCH 2 -C 2 H 5 , OCH -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) propoxy, 3- (ethoxycarbonyl) propoxy, 3- (n-propoxycarbonyl) propoxy, 3- (n-butoxycarbonyl) prop
  • (-C-C 6 alkoxy) carbonyl-C 6 -C 6 alkyl for: Ci-Ce alkyl substituted by (Ci-C ⁇ - alkoxy) carbonyl as mentioned above, for example for methoxycarbonylmethyl, ethoxycarbonylmethyl,
  • (C ⁇ -C 6 -alkoxy) carbonyl -C-COE-alkylsulfonyl for: by (Ci-C ⁇ alkoxy) carbonyl as mentioned above substituted C ⁇ -C 6 alkylsulfonyl, eg methoxycarbonylmethyl - sulfonyl, Ethoxycarbonylmethy1sulfonyl, 1 - ( Methoxycarbonyl) ethylsulfonyl, 2 - (methoxycarbonyl) ethylsulfonyl, 2- (ethoxycarbonyl) ethylsulfonyl, 3 - (methoxycarbonyl) propylsulfonyl, 4- (methoxycarbonyl) butylsulfonyl, 5- (methoxycarbonyl) pentylsulfonyl or 6- (methoxycarbonyl) hexylsulfonyl ;
  • -C 6 -Alkylthio -C ⁇ -C 6 -alkyl for: -C-C 6 -Alkylthio as above-substituted C ⁇ -C 6 alkyl, for example for CH 2 -SCH 3 , CH 2 -SC 2 H 5 , CH 2 -SCH 2 -C 2 H 5 , CH 2 -SCH (CH 3 ) 2 , n-butylthiomethyl, CH 2 -SCH (CH 3 ) -C 2 H 5 , CH 2 -SCH 2 -CH ( CH 3 ) 2 , CH 2 -SC (CH 3 ) 3 , 2- (SCH 3 ) ethyl, 2- (SC 2 H 5 ) ethyl, 2- (SCH 2 -C 2 H 5 ) ethyl, 2- [SCH (CH 3 ) 2 ] ethyl, 2- (n-butylthio) ethyl, 2- [SCH (CH 3 ) -C 2 H 5
  • C 1 -C 6 -alkylthio-C 1 -C 6 -alkoxy for: C 1 -C 6 -alkylthio substituted with C 1 -C 6 -alkoxy as mentioned above, for example for OCH 2 -SCH 3 , OCH 2 -SC 2 H 5 , OCH 2 -SCH 2 -C 2 H5, OCH 2 -SCH (CH 3 ) 2 , OCH 2 -S (nC 4 H 9 ), OCH 2 -SCH (CH 3 ) -C 2 H 5 , OCH 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 ] ethoxy, 2- (n-butylthio) ethoxy,
  • Ci-C ⁇ -alkylthio as mentioned above, preferably SCH 3 or SC 2 H 5 , substituted (C_-C 6 alkyl) carbonyl , e.g.
  • - C 3 -C 6 alkenyl for: for example prop-2-en-1-yl, n-buten-4-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2 -en-l-yl, 2-butene-l-yl, n-pent-en-3-yl, n-penten-4-yl, 1-methyl-but-2-en-l-yl, 2-methyl -but-2-en-l-yl, 3-methyl-but-2-en-l-yl, l-methyl-but-3-en-l-yl,
  • C 3 -C 6 alkenyloxy for: prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n -Butene-3-yloxy, 1-methyl-prop-1-en-1-yloxy, 2-methyl-prop-1-en-1-yloxy, 1-methyl-prop-2-en-1-yloxy, 2 -Methyl-prop-2-en-1-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methyl-but -l-en-l-yloxy, 2-methyl-but-1-en-l-yloxy, 3-methyl-but-l-en-l-yloxy, l-methyl-but-2-en-en-
  • C 3 -C 6 haloalkenyloxy for: C3-C6 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-trichloroallyloxy, 2, 3-dichlorobut-2-enyloxy, 2-bromoallyloxy, 3-bromoallyloxy, 2, 3-dibromoallyloxy, 3, 3-dibromoallyloxy, 2, 3, 3-tribromoallyloxy or 2, 3-dibromobut-2-enyloxy, especially for 2-chloroallyloxy or 3, 3-dichloroallyloxy;
  • Phenyl-C 3 -C 6 -alkenyloxy for: for example 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, in particular for 3-phenylallyloxy;
  • Heterocyclyl -C 3 -C 6 -alkenyloxy for: e.g. 3-heterocyclyl-allyl-oxy, 4-heterocyclyl-but-2-enyloxy, 4-heterocyclyl-but-3-enyl-oxy or 5-heterocyclyl-pent-4- enyloxy, preferably 3-heterocyclic allyloxy or 4-heterocyclyl-but-2-enyloxy, in particular for 3-heterocyclyl allyloxy;
  • C 2 -C 6 alkenylthio for: ethenylthio, prop-1-en-l-yl hio, prop-2-en-l-ylthio, 1-methylethenylthio, n-buten-1-ylthio, n-buten-2- ylthio, n-buten-3-ylthio, 1-methyl-prop-l-en-l-yl-thio, 2-methyl-prop-l-en-l-ylthio, l-methyl-prop-2-en- l-yl-thio, 2-methyl-prop-2-en-l-ylthio, n-penten-1-ylthio, n-penten-2-ylthio, n-penten-3-ylthio, n-penten-4- ylthio, 1-methyl-but-l-en-l-ylthio, 2-methyl-but-l-en-l-ylthio, 3-methyl-but-l-en-l-y
  • Heterocyclyl-C3-C6-alkynyloxy for: e.g. 3- (heterocyclyl) prop-2-in-l-yloxy, 4- (heterocyclyl) but-2-in-l-yloxy, 3- (heterocyclyl) 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 6 -alkynylthio, in particular for ethynylthio or prop-2-ynthio;
  • (C 3 ⁇ C 6 alkenyloxy) carbonyl for: prop-1-en-l-yloxycarbonyl, prop-2-en-l-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-buten-2- yloxycarbonyl, n-butene-3-yloxycarbonyl, 1-methyl-prop-l-en-l-yloxycarbonyl, 2-methyl-prop-1-en-l-yloxycarbonyl, l-methyl-prop-2-en-l- yloxycarbonyl, 2-methyl-prop-2-en-l-yloxycarbonyl, n-penten-1-yloxycarbonyl, n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n-penten-4-yloxycarbonyl, 1- Methyl-but-l-en-l-yloxycarbonyl, 2-methyl-
  • (C 3 -C 6 -Alkenyloxy) carbonyl-Ci-C ⁇ -alkyl for: substituted by (C 3 -C 6 -alkenyloxy) carbonyl as mentioned above, preferably prop-2-en-1-yl -oxycarbonyl -C 6 alkyl, for example prop-2-en-1-yl -oxycarbonyl -methyl;
  • (C 2 -C 6 alkenyl) carbonyloxy for: ethenylcarbonyloxy, prop-1-en-1-ylcarbonyloxy, prop-2-en-l-ylcarbonyloxy, 1-methylethenylcarbonyloxy, n-buten-1-ylcarbonyloxy, n-butene- 2-ylcarbonyloxy, n-buten-3-ylcarbonyloxy, 1-methyl-prop-l-en-l-ylcarbonyloxy, 2-methyl-prop-l-en-l-ylcarbonyloxy, l-methyl-prop-2-en- l-yl-carbonyloxy, 2-methyl-prop-2-en-l-ylcarbonyloxy, n-pentene-1-ylcarbonyloxy, n-pentene-2-ylcarbonyloxy, n-pentene-3-yl-carbonyloxy, n-pentene 4-ylcarbonyloxy, 1-methyl-but-l-en-
  • (C 2 -C 6 alkenyl) carbonylthio for: ethenylcarbonylthio, prop-1-en-l-ylcarbonylthio, prop-2-en-l-ylcarbonylthio, 1-methylethenylcarbonylthio, n-buten-1-ylcarbonylthio, n- Buten-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-penten-4-yl-carbony
  • (C 2 -C 6 alkynyl) carbonyloxy for: ethynylcarbonyloxy, prop-1-in-1-ylcarbonyloxy, prop-2-in-1-ylcarbonyloxy, n-but-1-in-l-ylcarbonyloxy, n- But-l-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-yl - carbonyloxy, n-pent-2-in-4-ylcarbonyloxy, n-pent-2-in-5-ylcarbonyloxy, n-
  • C 3 -C 6 alkynyloxy -CC-C6-alkyl for: by C 3 -C 6 -alkynyloxy as mentioned above, preferably propargyloxy, but-l-in-3-yl-oxy, but-l-in-4 -yloxy or but-2-yn-l-yloxy, substituted -CC 6 alkyl, for example for propargyloxymethyl or 2-propargyloxyethyl;
  • C3-C 6 cycloalkyl of: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • C 3 -C 6 cycloalkyloxy for: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy;
  • C 3 -C 6 cycloalkylthio for: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio, •
  • C 3 -C 6 cycloalkylcarbonyloxy for: cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or cyclohexylcarbonyloxy
  • C 3 -C 6 cycloalkylsulfonyloxy for: cyclopropylsulfonyloxy, cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy
  • cyclopent-1-enyloxy 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 are:
  • Examples of unsaturated heterocycles are: dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1,3-oxazolin-2-yl.
  • 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, 1,2,4-oxadiazol-5-yl and 1, 3, 4-oxadiazol-2-yl, thiadiazolyl such as 1, 2, 4-thiadiazol-3-yl,
  • All phenyl, carbocyclic and heteroyclic rings are preferably unsubstituted or bear a substituent.
  • R 1 is hydrogen, amino or methyl, especially methyl
  • C ⁇ -C4 haloalkylthio C I -C ⁇ "alkylsulfinyl, halo-C 1 -C 4 alkylsulfinyl, Ci-C ö alkylsulfonyl or C 1 -C 4 haloalkyl - sulfonyl, in particular C ⁇ -C4-haloalkoxy or C 3. -C 4 haloalkyl - thio; b) C 1 -C 4 haloalkyl or branched C 3 -C 6 alkyl;
  • 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 4 a hydrogen; b) fluorine or chlorine, especially fluorine;
  • R 5 cyano or halogen, in particular a) cyano; b) chlorine;
  • R 6 together with R 5 on the one hand a radical -N (R 7 ) -CO-C (R 8 ', R 9 ') -0- which is bonded to R 5 via the oxygen;
  • Halogen nitro, cyano, hydroxy, C 3 -C 6 cycloalkyl, C ⁇ -C 6 alkoxy, C 3 -C 6 cycloalkoxy, C 3 -C 6 ⁇ alkenyloxy,
  • -C ⁇ CC (R 14 ) N-OR 1: I , - C (Z 3 R 17 ) (ZR 18 ) - OR 24 , -C (Z 3 R 17 ) (Z 4 R 18 ) -SR 24 , -C (Z 3 R 17 ) (Z 4 R 18 ) -N (R 25 ) R 26 or -CO-N (R 25 ) -R 26 ;
  • Ci-C ⁇ alkoxy C 2 -C 6 alkenyloxy or C 2 -Ce alkynyloxy, each of these 3 radicals optionally being able to carry one to three substituents, each selected from the group consisting of halogen, -C-C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, -C-C 6 -alkylsulfonyl, -CO-R 12 , -CO-OR 12 ,
  • R 25 and R 26 independently of one another are hydrogen, -CC 6 -alkyl, C 3 -C 6 -alkenyl, C 2 -C 6 -alkynyl,
  • substituted 1-aryl-1,3-dihydro-imidazole-2- (thi) ones of the formulas Ib to Ig are particularly preferred, in particular
  • R 30 represents Ci-C ⁇ -alkyl or C ⁇ -C 4 haloalkyl
  • L 1 stands for a common leaving group such as halide
  • an inert solvent / diluent for example in a hydrocarbon such as n-hexane and toluene, a halogenated hydrocarbon such as dichloromethane, an ether such as diethyl ether, tetrahydrofuran and dioxane, or in an aprotic solvent such as acetonitrile, dimethylformamide and dimethyl sulfoxide , It is also possible to work in a 2-phase system from one of the solvents and water mentioned above, in which case the addition of a customary phase transfer catalyst is recommended.
  • a hydrocarbon such as n-hexane and toluene
  • a halogenated hydrocarbon such as dichloromethane
  • an ether such as diethyl ether
  • tetrahydrofuran and dioxane or in an aprotic solvent such as acetonitrile, dimethylformamide and dimethyl sulfoxide
  • inorganic bases e.g. Alkali or alkaline earth metal carbonates such as sodium carbonate, alkali or alkaline earth metal hydroxides such as sodium hydroxide, alkali metal hydrides such as sodium hydride, as well as organic bases, e.g. tertiary amines such as triethylamine and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) can be considered.
  • inorganic bases e.g. Alkali or alkaline earth metal carbonates such as sodium carbonate
  • alkali or alkaline earth metal hydroxides such as sodium hydroxide
  • alkali metal hydrides such as sodium hydride
  • organic bases e.g. tertiary amines such as triethylamine and 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU)
  • the reaction temperature is generally between the melting point and the boiling point of the reaction mixture, preferably from 0 to 100 ° C.
  • base and alkylating agent are used in approximately equimolar amounts, based on the amount of III. In order to obtain the product of value in the highest possible yield, however, it may also be advantageous to use base and / or alkylating agent in excess, up to about five times the molar amount, based on the amount of III.
  • Suitable halogenating agents are, for example, fluorine, chlorine, bromine, diethylaminosulfur trifluoride (DAST), N-chlorosuccinimide, N-bromosuccinimide, sulfuryl chloride, thionyl chloride, phosgene, phosphorus trichloride, phosphorus oxychloride, phosphorus tribromide and phosphorus oxybromide.
  • DAST diethylaminosulfur trifluoride
  • an inert solvent / diluent e.g. in a hydrocarbon such as n-hexane and toluene, a halogenated hydrocarbon such as dichloromethane, an ether such as diethyl ether, tetrahydrofuran and dioxane, an alcohol such as methanol and ethanol, a lower carboxylic acid such as acetic acid, or in an aprotic solvent such as acetonitrile.
  • a hydrocarbon such as n-hexane and toluene
  • a halogenated hydrocarbon such as dichloromethane
  • an ether such as diethyl ether, tetrahydrofuran and dioxane
  • an alcohol such as methanol and ethanol
  • a lower carboxylic acid such as acetic acid
  • aprotic solvent such as acetonitrile
  • the reaction temperature is generally between the melting point and the boiling point of the reaction mixture, preferably from 0 to 100 ° C.
  • the reaction is particularly successful when V bears an electron-withdrawing group ortho or para to the fluorine atom.
  • V a fluoroaromatic which can be converted into V can also be used.
  • the usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids. 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.
  • 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
  • butoxide also basic organic nitrogen compounds, for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N -Dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2, 4-dimethyl, 2, 6-dimethyl, 3, 4-dimethyl and 3, 5-dimethylpyridine, 5 -Ethyl-2-methylpyridine, 4-dimethylaminopyridine, N-methylpiperidine, 1, 4-diazabicyclo [2, 2, 2] octane (DABCO), 1, 5-Diazabicyclo [4,3,0] non-5-ene (DBN) or 1,8-diazabicyclo [5, 4, 0] -undec-7-ene (DBU).
  • 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) ) or carbon tetrachloride, dialkyl ethers such as diethyl ether, diisopropyl ether, methyl tert-butyl ether (MTBE), ethyl tert-butyl
  • TAME ethyl tert. - pentyl ether
  • THF tetrahydrofuran
  • 1,4-dioxane 1,4-dioxane
  • ethylene glycol di-methyl 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,
  • 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, in particular 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 elevated or reduced pressure - generally at 0.1 to 10 bar.
  • the starting compounds IIla / IIIb of process A> can be prepared in a manner known per se, e.g.
  • the intermediate XI can be isolated, especially when working without a base.
  • reaction auxiliaries diluents, reaction temperature and quantitative ratios
  • the information given above for processes A> and B> applies.
  • the l-arylimidazolidin-2, 4-diones II can be aminated or alkylated in a manner known per se:
  • aminating agents are Chloramine or 0- (2, 4-dinitrophenyl) hydroxylamine into consideration.
  • alkylating agents e.g. Alkyl halides, alkyl sulfates, alkyl mesylates and alkyl tosylates are suitable.
  • reaction auxiliaries diluents, reaction temperature and quantitative ratios
  • the information given above for processes A> and B> applies.
  • the l-arylimidazolidin-2, 4 -dione lilac can be converted into the corresponding l-aryl-2-thioxo-imidazolidin-4-one Illb by means of sulfurization:
  • 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 aromatic hydrocarbon such as toluene and the xylenes
  • an ether such as diethyl ether, 1, 2-dimethoxyethane and tetrahydrofuran
  • organic amine such as pyridine
  • Phosphorus (V) sulfide and 2,4-bis (4-methoxyphenyl) -1,3,4,4-di-thiadiphosphetane-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.
  • R 2 C 1 - C 4 haloalkyl or branched C 3 -C 6 alkyl
  • XIV L 4 stands for usual leaving groups, for example C 1 -C 4 alkyl or benzyl.
  • L 5 and L 6 stand for usual leaving groups, for example for C ⁇ -C 6 alkyl
  • the substituted 1-aryl-1,3-dihydro-imidazole -2 - (thi) one I can be prepared by one of the synthesis methods mentioned above.
  • 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, distributing the residue in a mixture of water and a suitable organic solvent and working up the organic phase towards the product.
  • the substituted 1-aryl-l, 3-dihydro-imidazole-2 - (thi) one I can be obtained in the preparation as isomer mixtures, but if desired by the usual methods such as crystallization or chromatography, also on an optically active adsorbate , can be separated into the pure isomers. 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.
  • a base of the corresponding cation preferably an alkali metal hydroxide or hydride
  • 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:
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • substituted 1-aryl-1, 3 -dihydroimidazole-2 - (thi) one I and their agriculturally useful salts are also suitable for the desiccation and / or defoliation of plants.
  • desiccants are particularly suitable for drying out the above-ground parts of crops such as potatoes, rapeseed, sunflower and soybeans. This enables a fully mechanical harvesting of these important crops.
  • the waste promoted by the use of active compounds of the formula I according to the invention and their agriculturally useful salts is based on the formation of separating tissue between the fruit or leaf and shoot part of the plants.
  • Cotton defoliation is of particular economic interest because it makes harvesting easier. At the same time, the shortening of the time interval in which the individual plants mature leads to an increased quality of the harvested fiber material.
  • the compounds I or the compositions comprising them can be sprayed, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules. Nebulizing, dusting, scattering or pouring be applied.
  • 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.
  • inert auxiliaries mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore 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.
  • mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils as well as oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffins, tetrahydronaphthalene, alkylated n
  • Aqueous use forms can be made from emulsion concentrates,
  • Suspensions, pastes, wettable powders or water-dispersible granules can be prepared by adding water.
  • wetting agents, adhesives, dispersants or emulsifiers n
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols as well as of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives Formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylpheny
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, 5 chalks, boluses, 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 flour, tree bark, wood and nutshell flour, cellulose powder or other 10 solid carriers.
  • mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, 5 chalks, boluses, 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 flour, tree bark, wood
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations contain about 0.001 to 15 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • V. 3 parts by weight of active ingredient No. Ib.22 are mixed with 97 parts by weight of finely divided kaolin. In this way, a dusting agent is obtained which contains 3% by weight of the active ingredient.
  • Wettol ® EM 31 nonionic emulsifier based on ethoxylated castor oil; BASF AG.
  • 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, if possible, while the active ingredients are applied to the leaves underneath growing unwanted plants 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.
  • substituted 1-aryl-1,3-di-hydroimidazole-2 - (thi) one I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • Example 1 4-chloro-3- [4-chloro-2-fluoro-5- (prop-2-vinyloxy) phenyl] -5- (difluoromethylthio) -1-methyl -1, 3-dihydro-imidazole-2 -one
  • 1- [4-chloro-2-fluoro-5- (prop-2-ynyloxy) phenyl] -4- (difluoromethylthio) -3-methyl-1,3-dihydro-imidazole-2 -one in 30 ml of toluene was added at about 0-5 ° C a solution of 0.22 ml of sulfuryl chloride in 5 ml of toluene.
  • the resulting product of value was extracted from the aqueous phase with five times 70 ml of ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The crude product was purified by stirring with 20 ml of diisopropyl ether and then filtering off the undissolved product of value. Yield: 1 g; Mp .: 102-104 ° C.
  • 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 treatment was 31.3 and 15.6 g / ha aS (active substance).
  • the plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C. 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.
  • the plants used in the greenhouse experiments are composed of the following types:
  • the young cotton plants were dripping wet with aqueous preparations of the sheet-treated active ingredients (with an addition of 0.15 wt .-% of the fatty alcohol alkoxylate Plurafac LF ® 700 1), based on the spray mixture).
  • the amount of water applied was around 1000 l / ha. After 13 days, the number of leaves dropped and the degree of defoliation in% were determined. No leaf fall occurred in the untreated control plants.

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  • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des 1-aryle-1,3-dihydro-imidazole-(thi)ones de la formule (I) et leurs sels avec R1 = NH2, C1-C6-alkyle, C1-C6-halogénure d'alkyle; R2 = OH, SH, C¿1?-C6-alkoxy, C1-C4-alkylthio, C1-C4-halogénure d'alkylthio, C1-C6-alkylsulfinyle, C1-C4-halogénure d'alkylsulfinyle, C1-C6-alkylsulfonyle, C1-C4-halogénure d'alkylsulfonyle, C1-C4-halogénure d'alkyle ou C1-C6-alkyle; R?3¿ = H, halogène, C¿1?-C6-alkyle, halogénure de méthyle; R?4¿ = H, halogène; R5 = CN, halogène, -CO-NH¿2?, -CS-NH2, -OC(R?8,R9¿)-CO-O(C¿1?-C6-alkyle); Y = N, CH, ou un pont avec R?6¿ ⊃C-O-C(R10)=N-, ⊃C-S-C(R10)=N-, ou ⊃C-N=C(R?10)-O-; R6+R5¿ = est un reste lié à R5 par l'oxygène -N(R7)-(C(O/S)-C(R8', R9')-O-, ou 1) OH, SH, CN, NO¿2?, C1-C6-alkyle, C1-C6-halogénure d'alkyle, C1-C6-halogénure d'alkoxy, C1-C6-halogénure d'alkylthio, C1-C6-alkylthio-(C1-C6-alkyle)carbonyle, (C1-C6-alkyle)iminooxycarbonyle, C1-C6-alkoxy-C1-C6-alkyle, C1-C6-alkoxyamino-C1-C6-alkyle, C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyle, 2) éventuellement subst. C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkyloxy, C3-C6-cycloalkylthio, C2-C6-alcényloxy, C2-C6-alcénylthio, C2-C6-alkinyloxy, C2-C6-alkinylthio, (C1-C6-alkyle)carbonyloxy, (C1-C6-alkyle)carbonylthio, (C1-C6-alkoxy)carbonyloxy, (C2-C6-alcényle)carbonyloxy, (C2-C6-alcényle)carbonythio, (C2-C6-alkinyle)carbonyloxy, (C2-C6-alkinyle)carbonylthio, C1-C6-alkylsulfonyloxy, ou C1-C6-alkylsulfonyle, 3) 28 autres restes; R?7¿ = H, éventuellement subst. C¿1?-C6-alkyle, C3-C6-alcényle, C3-C6-alkinyle, C1-C6-alkoxy, C3-C6-alcényloxy, C3-C6-alkinyloxy, C3-C6-cycloalkyle ou C3-C6-cycloalkyloxy; R?8, R9, R8', R9'¿ = H, CN, C¿1?-C6-alkyle; R?10¿ = H, halogène, éventuellement subst. C¿1?-C6-alkyle, C3-C6-alcényle, C3-C6-alkinyle, C1-C6-alkoxy, C3-C6-alcényloxy, C3-C6-alkinyloxy, C3-C6-cycloalkyle ou C3-C6-cycloalkyloxy. Ces composés peuvent être utilisés en tant qu'herbicides ou pour la dessiccation/défoliation de plantes.
EP00967704A 1999-10-01 2000-09-19 Derives de 1-aryle-1,3-dihydro-imidazole-2-(thi)ones, fabrication, et utilisation en tant qu'herbicides ou pour la dessiccation/defoliation de plantes Withdrawn EP1218350A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19947189 1999-10-01
DE19947189 1999-10-01
PCT/EP2000/009152 WO2001025216A1 (fr) 1999-10-01 2000-09-19 Derives de 1-aryle-1,3-dihydro-imidazole-2-(thi)ones, fabrication, et utilisation en tant qu'herbicides ou pour la dessiccation/defoliation de plantes

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Publication number Priority date Publication date Assignee Title
US3494932A (en) * 1967-06-26 1970-02-10 American Cyanamid Co Aminoalkyl substituted aryl hydantoins
GB1337269A (en) * 1970-01-05 1973-11-14 Exxon Research Engineering Co Phosphorus and thiophosphorus acid ester derivatives of substituted hydantoins
EP0011693A1 (fr) * 1978-10-03 1980-06-11 Ciba-Geigy Ag N-hétérocycles N-substitués par trifluorométhane-sulfonylaminophényle, leur préparation, compositions les contenant et leur utilisation pour la régulation de la croissance des plantes
US4473393A (en) * 1982-08-06 1984-09-25 Buffalo Color Corporation Pesticidal thiohydantoin compositions
US4464387A (en) * 1982-08-06 1984-08-07 Buffalo Color Corp. Insecticidal phenyl hydantoin compounds
CN85106905A (zh) * 1985-08-08 1987-02-04 Fmc公司 含有1-芳基-δ2-1，2，4，-三唑啉-5-酮类的除草剂及其制备方法
DE3832348A1 (de) * 1988-03-10 1989-09-28 Bayer Ag Substituierte benzoxazinone, mehrere verfahren sowie neue zwischenprodukte zu ihrer herstellung sowie ihre herbizide verwendung
DE3839480A1 (de) * 1988-11-23 1990-05-31 Bayer Ag N-aryl-stickstoffheterocyclen, verfahren sowie neue zwischenprodukte zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwuchsregulatoren
DE4414568A1 (de) * 1994-04-27 1995-11-02 Bayer Ag Heterocyclylbenzonitrile

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0125216A1 *

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CA2387706A1 (fr) 2001-04-12

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