EP1157012A1 - 1-aryl-1,3,5-triazin-4-thion-2,6-diones, leur preparation et leur utilisation en tant qu'herbicides - Google Patents

1-aryl-1,3,5-triazin-4-thion-2,6-diones, leur preparation et leur utilisation en tant qu'herbicides

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Publication number
EP1157012A1
EP1157012A1 EP00907538A EP00907538A EP1157012A1 EP 1157012 A1 EP1157012 A1 EP 1157012A1 EP 00907538 A EP00907538 A EP 00907538A EP 00907538 A EP00907538 A EP 00907538A EP 1157012 A1 EP1157012 A1 EP 1157012A1
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EP
European Patent Office
Prior art keywords
alkyl
alkoxy
methyl
carbonyl
hydrogen
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP00907538A
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German (de)
English (en)
Inventor
Olaf Menke
Ingo Sagasser
Gerhard Hamprecht
Robert Reinhard
Cyrill Zagar
Karl-Otto Westphalen
Martina Otten
Helmut Walter
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BASF SE
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BASF SE
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Publication of EP1157012A1 publication Critical patent/EP1157012A1/fr
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/38—Sulfur atoms
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the present invention relates to novel l-aryl-4-thiotriazines of the formula I.
  • R 1 is hydrogen, amino, C ⁇ -C 4 alkyl or C ⁇ -C4-haloalkyl, -
  • R 2 is hydrogen, amino, -CC 4 alkyl or C ! -C 4 haloalkyl; 0
  • R 3 is hydrogen or halogen
  • R 6 is hydrogen, halogen, -CC 6 alkyl, C 3 -C 6 alkenyl,
  • R 7 are hydrogen, C 6 -alkyl, C 6 haloalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 -alkynyl, (C ⁇ -C 6- alkoxy) carbonyl-C 6 alkyl or benzyl;
  • C 6 alkyl C 3 -C 6 cycloalkyl, C 3 -C 6 -cycloalkyl-C ⁇ -C 4 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 -alk- oxy-C ⁇ -C 6 alkyl, (C!
  • R 9 is hydrogen or C; L -C 6 alkyl
  • R 10 are hydrogen, C 6 alkyl or Ci-C ö -alkoxy, where the 2 last-mentioned radicals to carry one of the following substituents: Ci-C ß alkoxy, (C ⁇ -C 6 alkoxy) carbonyl or phenoxycarbonyl;
  • R 11 is hydrogen, -CC 6 alkyl or Ci-C ⁇ -haogenoalkyl
  • R 13 , R 14 independently of one another C] . -C 6 alkyl or together for a saturated 2- to 4-membered carbon - chain of substances which can carry a Ci-C ⁇ -alkyl radical;
  • R 15 is hydrogen, cyano, halogen or -CC 6 alkyl
  • R 20 , R 23 independently of one another are hydrogen, C 1 -C 6 -alkyl,
  • Ci-Ce-haloalkyl C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, where the latter 4 groups can each carry one or two of the following radicals: cyano, halogen, hydroxy, hydroxycarbonyl, Ci-C ⁇ -alkoxy , Ci-C ⁇ -alkylthio,
  • -N , -NH- or -N (-C -C 6 alkyl) -;
  • the invention also relates to the use of the compounds I as herbicides, herbicidal compositions which comprise the compounds I as active substances,
  • DE-A 40 00 624 describes specially substituted 1-phenyltriazines which are said to have a fungicidal action. A herbicidal effect is not mentioned. Thiotriazines are not mentioned.
  • EP-A 640 600 describes substituted 4-thiotriazines with herbicidal activity which have a 4-5 annulation in the phenyl substituent.
  • aryl-triazinetrione of the type of compounds I and their use as herbicides are aryl-triazinetrione of the type of compounds I and their use as herbicides.
  • a large number of aryltriazines and arylthiotriazines fall under the general formulas; However, individual compounds with a thioketone group in the triazine part are not mentioned in either publication.
  • arylthiotriazines of the formula I as defined above have a particularly good herbicidal action.
  • herbicidal compositions have been found which contain the compounds I and have a very good herbicidal action.
  • 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.
  • 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, and the ammonium ion, which if desired one to four C ⁇ -C 4 alkyl and / or a phenyl or benzyl substituent can carry, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, further phosphonium ions, sulfonium ions, preferably tri (-C 4 alkyl) sulfonium and sulfoxonium ions, preferably Tri (-C 4 alkyl) s
  • 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] . -C 4 -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 23 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 alkyl for: CH 3 , C 2 H 5 , n-propyl, CH (CH 3 ) 2 , n-butyl, CH (CH 3 ) -C 2 H 5 , 2-methylpropyl or C (CH 3 ) 3 , in particular for CH 3 , C 2 H 5 or CH (CH 3 ) 2 ;
  • C ⁇ -C 4 -haloalkyl a C ⁇ -4 alkyl C as mentioned above, the, chlorine, bromine and / or iodine is partially or fully substituted by fluorine, eg CH 2 F, CHF 2, CF 3, CHC1, Dichloromethyl, trichloroethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2 -Chlor-2,2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, C 2 F 5 , 2-fluoropropyl, 3-fluoropropyl, 2, 2-di
  • - Ci-C ⁇ - alkyl for: -C-C 4 alkyl as mentioned above, and for example n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl , 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpenyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl or l-ethyl-2-methylpropyl, in particular for CH 3 , C 2 H
  • C ⁇ -C 6 -haloalkyl as mentioned above C ⁇ -C6 alkyl which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg one of said at C ⁇ -C 4 haloalkyl radicals or 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, especially for chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2- Chloroethyl or 2,
  • Phenyl-Cx-C ö -alkyl for: e.g. 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;
  • (-CC 6 alkyl) carbonyl for: CO-CH 3 , CO-C 2 H 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, 1, 2-dimethylpropylcarbonyl, 2, 2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentyl carbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl,
  • -C-C 6 alkoxy for: for example OCH 3 , OC 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-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethyl-propoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2-dimethylbutoxy,
  • (-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-methylbutoxy- carbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dirnethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methyl - pentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl, 1, 2-dimethyl
  • (-C-C 6 -alkoxy) carbonyloxy for: methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methyl-propoxycarbonyloxy, 1, 1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy , 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 2, 2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy,
  • Cx-Ce-alkylthio for: SCH 3 , SC 2 H 5 , SCH 2 -C 2 H 5 , SCH (CH 3 ) 2 ' n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC (CH 3 ) 3 , n -Pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio , 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethyl
  • C ⁇ -C 6 -alkoxy-C ⁇ -C6-alkyl viewed by C ⁇ alkoxy - as mentioned above - substituted C ⁇ -C6 alkyl, that is CH 2 OCH 3, CH 2 -0C 2 H 5 for example, , 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) ropyl, 2- (ethoxy) propyl
  • Ci-C ⁇ -alkoxy- (Ci-C ⁇ -alkoxy) carbonyl for: (Ci-C ⁇ - alkoxy) carbonyl substituted by Ci-C ⁇ - alkoxy as mentioned above, for example for CO-OCH 2 -0CH 3 , CO -OCH 2 -0C 2 H 5 , C0-0CH 2 -OCH 2 -C 2 H 5 , CO-OCH 2 -OCH (CH 3 ) 2 , n-butoxymethoxycarbonyl, (1-methylpropoxy) methoxycarbonyl, CO-OCH 2 -OCH 2 -CH (CH 3 ) 2 , CO-OCH 2 -OC (CH 3 ) 3 , 2- (methoxy) ethoxycarbonyl, 2- (ethoxy) ethoxycarbonyl, 2- (n-propoxy) ethoxycarbonyl, 2- (l-methylethoxy) ethoxycarbonyl, 2- (n -Butoxy) e
  • C 3 -C 6 alkenyl for: for example 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
  • C 2 -Cg alkenyl for: ethenyl or one of the radicals mentioned under C 3 - C ⁇ alkenyl, in particular for ethenyl or prop-2-en-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-l-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy ,, 1-methyl- but-l-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-
  • C 2 -C 6 alkenyloxy for: ethenyloxy or one of the radicals mentioned under C3-C6-alkenyloxy, in particular for ethenyloxy or prop-2-en-1-yloxy;
  • C 2 -C 6 alkenylthio for: ethenylthio, prop-1-en-l-ylthio, 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
  • C 3 -C 6 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-in
  • C 2 -C 6 alkynyl for: ethynyl or one of the radicals mentioned under C 3 - Q ⁇ , -alkynyl, in particular for ethynyl or prop -2-in-l-yl;
  • C 3 -C 6 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-yloxy, n-pent-1-in-3-yloxy , n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy, n-pent-2-yn-yl-oxy, n-pent-2-yn-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-1-in-3-yloxy
  • (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-pentene-1-yloxycarbonyl, n-pentene-2-yloxycarbonyl, n-pentene-3-yloxycarbonyl, n-pentene-4- yloxycarbonyl, 1-methyl-but-l-en-l-yloxycarbonyl, 2-
  • (C 3 -C 6 alkenyloxy) carbonyl -CC 6 alkyl for: by (C3-C6-alkenyloxy) carbonyl as mentioned above, preferably prop-2-en-1 -yloxycarbonyl, substituted Ci-C ⁇ Alkyl, for example prop-2 -en-1-yloxycarbonylmethyl;
  • (C 3 -C 6 alkynyloxy) carbonyl for: prop-1-in-l-yloxycarbonyl, prop-2-in-l-yloxycarbonyl, n-but-1-in-l-yloxycarbonyl, n-but-l- in-3-yloxycarbonyl, n-but-l-in-4-yloxycarbonyl, n-but-2-in-l-yloxycarbonyl, n-pent-1-in-l-yloxycarbonyl, n-pent-l-in- 3-yloxycarbonyl, n-pent-l-in-4-yloxycarbonyl, n-pent-l-in-5-yloxycarbonyl, n-pent-2-in-l-yloxycarbonyl, n-pent-2-in-4- yloxycarbonyl, n-pent-2-yn-5-yloxycarbonyl,
  • C 3 -C 6 cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • B cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1- (cyclopropyl) ethyl, 1- (cyclobutyl) ethyl, 1- (cyclopentyl) ethyl, 1- (cyclohexyl) ethyl, 2- (cyclopropyl) ethyl,
  • C 3 -C 6 cycloalkylthio for: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio.
  • 4- 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. Azetidin-1-yl, pyrrolidin-1-yl, isoxazolidin-2-yl, isothiazolidin-2-yl, oxazolidin-3-yl,
  • the variables preferably have the following meanings, individually or in combination:
  • R 1 is hydrogen, amino or methyl, especially methyl
  • R 2 is hydrogen, amino or methyl, especially methyl
  • R 3 is hydrogen or fluorine, in particular fluorine
  • R 4 cyano or halogen, in particular a) cyano; b) chlorine;
  • R 8 is hydrogen, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl,
  • R 8 ' is hydrogen, -CC 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl,
  • R 9 is hydrogen
  • R 11 is hydrogen
  • R 15 is hydrogen, halogen or -CC 6 alkyl, especially hydrogen, chlorine, bromine or methyl, particularly preferably chlorine;
  • R 20 C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, ⁇ -C 4 alkoxy-C ! -C 4 alkyl,
  • Ci -C 4 alkoxy- (C 1 -C 4 alkoxy) carbonylmethyl Ci -C 4 alkoxy- (C 1 -C 4 alkoxy) carbonylmethyl
  • C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl where the last 3 groups may carry one of the following radicals, respectively: C ⁇ -C6 alkoxy, (C ⁇ -C 6 -Alkoxy) carbonyl or (C 3 -C 6 -alkenyloxy) carbonyl.
  • the l-aryl-4-thiotriazines of the formula Ib are particularly preferred, in particular the compounds Ib.l to Ib.720, which differ from the corresponding compounds la.l to la.720 only in that R 2 is amino stands:
  • l-aryl-4-thiotriazines of the formula I can be obtained in various ways, in particular by one of the following processes:
  • the l-aryl-4-thiotriazines according to the invention are prepared by reacting aryl isocyanates with thioureas and subsequent cyclization.
  • the isocyanate is reacted with the thiourea in the presence of an activated carbon dioxide source.
  • an activated carbon dioxide source examples include carbodiimidazole, phosgene, diphosgene and triphosgene, and chloroformic acid esters.
  • Process (C)) according to the invention and processes (A>) and (B)) for the preparation of the compounds of the formula (I) are preferably carried out in the presence of a suitable reaction auxiliary.
  • 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
  • -butanolate also basic organic nitrogen compounds, for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, di-cyclohexylamine, 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-dimethylanimopyridine, 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-
  • Process (C>) according to the invention and processes (A)) and (B)) for the preparation of the compound of the formula (I) are preferably carried out in the presence of a diluent.
  • a diluent The usual organic solvents are generally suitable as diluents.
  • These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, for example pentane, hexane, heptane, petrol 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.
  • aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons for example pentane, hexane, heptane, petrol ether, ligroin, gasoline, benzene, toluene, xylene
  • TAME methyl tert. - 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 hexamethyl-phosphoric acid triamide
  • Esters such as methyl acetate, ethyl ester, n
  • Alkanols such as methanol, ethanol, n-propanol, isopropanol, n-, iso-, sec- and tert.
  • Butanol Glycol ethers such as ethylene glycol monomethyl ether, monoethyl ether, diethylene glycol monomethyl ether and monoethyl ether; their mixtures with water or pure water.
  • 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 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.
  • Atmospheric pressure or under the autogenous pressure of the respective reaction mixture it is also possible to ren under increased or reduced pressure - generally at
  • 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 l-aryl-4-thiotriazines I can be prepared by one of the synthesis methods mentioned above. For economic or procedural reasons, however, it may be more expedient to produce some compounds I from similar l-aryl-4-thiotriazines - which differ, however, in particular in the meaning of the radicals R 5 - in a manner known per se, for example by hydrolysis Esterification
  • the l-aryl-4-thiotriazines I can be used in the preparation as
  • 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 suitable: Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var.
  • 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, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, and also high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Atomizing, dusting, scattering or pouring can be used.
  • the application forms depend on the purposes; in any case, they should be as possible ensure the finest distribution of the active ingredients 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-thiotriazines 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.
  • 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 octadecanoien 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, tributylphenyl
  • 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 , Urea 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 , Urea and vegetable products such as flour, tree bark, wood and
  • 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).
  • Dispersion containing 0.02% by weight of the active ingredient.
  • 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 including growing unwanted plants or the uncovered
  • 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-thiotriazines I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • Table 3 lists further l-aryl-4-thiotriazines of the formula I which were prepared or can be prepared in an analogous manner:
  • the aqueous phase was adjusted to pH 10 with sodium hydroxide solution.
  • Precursor 8ß 3- (3-amino-4-chloro-6-fluoro-2-methoxy-phenyl) -1, 3-dimethyl-6-thi-oxo [1,3,5] triazinan-2, 4-dione
  • 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 covers until the plants had grown. This cover causes the test plants to germinate evenly, unless this was affected 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 post-emergence treatment costs were 125, 62.5, 7.81 and 3.91 g / ha a.S. (active substance).
  • 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.
  • the plants used in the greenhouse experiments are composed of the following types:
  • the active ingredient no. 39 showed a significantly better herbicidal action against Abutilon theophrasti, Chenopodium album, Ipomoea species, Solanum nigrum and Veronica species in the post-emergence process than the comparative compound B

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  • Chemical & Material Sciences (AREA)
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Abstract

Nouvelles 1-aryl-4-thiotriazines de formule (I) dans laquelle R<1> représente H, NH2, alkyle C1-C4, halogénoalkyle C1-C4; R<2> représente H, NH2, alkyle C1-C4, halogénoalkyle C1-C4; R<3> représente H, halogène; R<4> représente CN, halogène; Y représente azote, le groupe méthine ou, avec R<5>, un pont >C-O-C(R<6>)=N-; R<5> représente (1) hydrogène, hydroxy, mercapto, nitro, halogène, alkyle C1-C6, halogénoalkyle C1-C6, (2) alcoxy C1-C6, alkylthio C1-C6, cycloalcoxy C3-C6, cycloalkylthio C3-C6, alcényloxy C2-C6, alcénylethio C2-C6, alcynyloxy C2-C6 ou alcynylthio C2-C6, chacun de ces 8 restes pouvant porter, si nécessaire, l'un des substituants suivants: halogène, cyano, -CO-R<8>, -CO-OR<8> ou -CO-N(R<8>)-R<9>, (3) -CO-R<11>, -C(R<11>)(OR<13>)(OR<14>), -C(R<11>)=C(R<15>)-CO-R<16>, -CH(R<11>)-CH(R<15>)-CO-R<16>, -CO-OR<20>, -C(R<10>)=N-OR<7>, -N(R<21>)-R<22> ou -CO-N(R<21>)-R<22>; R<6> représente H, halogène, 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 éventuellement substitués, ainsi que leurs sels et énoléthers, procédé de préparation des nouveaux composés de formule (I) et leur utilisation en tant qu'herbicides.
EP00907538A 1999-02-23 2000-02-10 1-aryl-1,3,5-triazin-4-thion-2,6-diones, leur preparation et leur utilisation en tant qu'herbicides Withdrawn EP1157012A1 (fr)

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DE19907649 1999-02-23
DE19907649 1999-02-23
PCT/EP2000/001072 WO2000050409A1 (fr) 1999-02-23 2000-02-10 1-aryl-1,3,5-triazin-4-thion-2,6-diones, leur preparation et leur utilisation en tant qu'herbicides

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BR (1) BR0008435A (fr)
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NO (1) NO20014050L (fr)
NZ (1) NZ513917A (fr)
PL (1) PL350853A1 (fr)
SK (1) SK11792001A3 (fr)
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US6613718B2 (en) 2001-10-01 2003-09-02 Ishihara Sangyo Kaisha, Ltd. Aryl ether derivatives and processes for their preparation and herbicidal and desiccant compositions containing them
US7429035B2 (en) * 2005-09-29 2008-09-30 Wprwmdm, L.L.C. Equipment handling apparatus
EP3034528B1 (fr) * 2014-12-19 2017-06-21 Evonik Degussa GmbH Systèmes de co-réticulation pour feuilles d'encapsulage comprenant des combinaisons d'urée
CN112745305A (zh) * 2019-10-29 2021-05-04 沈阳中化农药化工研发有限公司 一种三嗪酮类化合物及其用途
CA3160070A1 (fr) * 2019-11-07 2021-05-14 Qingdao Kingagroot Chemical Compound Co., Ltd. Compose aromatique contenant de l'isoxazoline substitue, procede de preparation correspondant, composition herbicide et utilisation associee
BR112022013644A2 (pt) 2020-01-11 2022-09-13 Qingdao Kingagroot Chemical Compound Co Ltd Composto iminoaril substituído por derivado de ácido carboxílico, método de preparação, composição herbicida e uso dos mesmos
CN113402510B (zh) 2020-01-16 2023-04-28 青岛清原化合物有限公司 一种稠环取代的芳香类化合物及其制备方法、除草组合物和应用
CN113831299B (zh) * 2020-06-23 2023-12-01 沈阳中化农药化工研发有限公司 苯甲酸酯类化合物及其应用
CN113831298B (zh) * 2020-06-23 2023-12-01 沈阳中化农药化工研发有限公司 光活性羧酸酯类化合物及其应用
WO2021259224A1 (fr) 2020-06-23 2021-12-30 沈阳中化农药化工研发有限公司 Composé triazine benzoate et son application
WO2023117670A1 (fr) 2021-12-22 2023-06-29 Syngenta Crop Protection Ag Composés herbicides de type triazine

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CA2364660A1 (fr) 2000-08-31
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SK11792001A3 (sk) 2002-01-07
BR0008435A (pt) 2002-01-15
JP2002537387A (ja) 2002-11-05
US6602825B1 (en) 2003-08-05
BG105921A (en) 2002-06-28
AU2909400A (en) 2000-09-14
NZ513917A (en) 2001-09-28
HUP0200030A3 (en) 2003-01-28
WO2000050409A1 (fr) 2000-08-31
NO20014050L (no) 2001-08-22
CN1341105A (zh) 2002-03-20
KR20010108246A (ko) 2001-12-07
ZA200107802B (en) 2002-09-23
CZ20013015A3 (cs) 2002-07-17
PL350853A1 (en) 2003-02-10
NO20014050D0 (no) 2001-08-20
IL144741A0 (en) 2002-06-30
HUP0200030A2 (hu) 2002-05-29

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