EP0663917A1 - Triazolinones substituees - Google Patents

Triazolinones substituees

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Publication number
EP0663917A1
EP0663917A1 EP93921909A EP93921909A EP0663917A1 EP 0663917 A1 EP0663917 A1 EP 0663917A1 EP 93921909 A EP93921909 A EP 93921909A EP 93921909 A EP93921909 A EP 93921909A EP 0663917 A1 EP0663917 A1 EP 0663917A1
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
straight
chain
branched
alkyl
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.)
Ceased
Application number
EP93921909A
Other languages
German (de)
English (en)
Inventor
Kurt Findeisen
Karl-Heinz Linker
Otto Schallner
Klaus-Helmut Müller
Klaus König
Hans-Joachim Santel
Robert R. Schmidt
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0663917A1 publication Critical patent/EP0663917A1/fr
Ceased legal-status Critical Current

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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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/12—Organo silicon halides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages

Definitions

  • the invention relates to new substituted triazolinones, several processes for their preparation and their use as herbicides. It is known that certain substituted triazolinones such as the compound 2-methyl-3-dimethylamino-l- [N- (2,2-dimethyl-1-propyl) aminocarbonyl] 1,2,4-triazolin-5-one have herbicidal properties (see, for example, EP 431 390).
  • R 1 , R 2 and R 3 each independently represent halogen, alkyl, alkenyl, alkynyl, alkoxy or optionally substituted arylalkyl, aryl or aryloxy,
  • A represents a doubly linked alkanediyl radical and ⁇ 1 represents oxygen or sulfur
  • R 4 for hydrogen, halogen, cyano, nitro, for optionally substituted
  • Alkyl for alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy,
  • Alkylthio, alkylsulfmyl, alkylsulfonyl, alkoxycarbonyl represents in each case optionally substituted cycloalkyl, aryl or aryloxy or for a radical of the formula
  • R 5 stands for hydrogen, cyano, for optionally substituted alkyl, for alkenyl, alkynyl, alkoxy, alkoxycarbonyl, aminocarbonyl, for amino, N-alkylamino, N, N-dialkylamino, alkylidenimino or for optionally substituted cycloalkyl, aryl or aryloxy,
  • R 6 for alkyl, alkoxy, alkylthio or for a radical of the formula
  • R 7 represents alkyl or cycloalkyl
  • R 8 and R 9 either independently of one another each represent hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl or each optionally substituted arylalkyl or aryl or together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle,
  • R 10 and R 1 1 either independently of one another in each case for alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl,
  • the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or isomer mixtures of different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.
  • R 1 , R 2 and R 3 each independently represent halogen, alkyl, alkenyl, alkynyl, alkoxy or optionally substituted arylalkyl, aryl or aryloxy,
  • A represents a double-linked alkanediyl radical and ⁇ 1 represents oxygen or sulfur,
  • R 4 for hydrogen, halogen, cyano, nitro, for optionally substituted alkyl, for alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkoxycarbonyl, for each ge optionally substituted cycloalkyl, aryl or aryloxy or represents a radical of the formula
  • R 5 stands for hydrogen, cyano, for optionally substituted alkyl, for alkenyl, alkynyl, alkoxy, alkoxycarbonyl, aminocarbonyl, for amino, N-alkylamino, N, N-dialkylamino, alkylidenimino or for optionally substituted cycloalkyl, aryl or aryloxy,
  • R 6 for alkyl, alkoxy, alkylthio or for a radical of the formula
  • R 7 represents alkyl or cycloalkyl
  • R 8 and R 9 either independently of one another each represent hydrogen, alkyl
  • R 10 and R 1 1 either independently of one another each represent alkyl, alkenyl,
  • X 2 represents oxygen or sulfur is obtained if a) 1-chloro (thio) carbonyltriazolinones of the formula (II),
  • R 1 , R 2 , R 3 and A have the meanings given above, if appropriate in Gregenwart, reacting a diluent and also in the presence of a reaction auxiliary, or if b) triazolinones of the formula (IV) which are unsubstituted in the 1-position,
  • R 1 , R 2 , R 3 , A and X 1 have the meanings given above, if appropriate in Gregenwart of a diluent and if appropriate in the presence of a reaction auxiliary.
  • the substituted triazolinones of the general formula (I) according to the invention show a considerably better herbicidal activity against problem weeds and, at the same time, significantly better tolerance to important crop plants in comparison to the substituted triazolinones known from the prior art, such as the compound 2-methyl-3- dimethylamino-1- [N- (2,2-dimethyl-1-propyl) aminocarbonyl] -1,2,4-triazolin-5-one, which are chemically and functionally obvious compounds.
  • Formula (I) provides a general definition of the substituted triazolinones according to the invention.
  • Compounds of formula (I) are preferred in which
  • Het stands for a heterocycle of the formula or
  • R 1 , R 2 and R 3 independently of one another each for fluorine, chlorine, bromine, iodine, for straight-chain or branched alkyl having 1 to 8 carbon atoms, for straight-chain or branched alkenyl with 2 to 8 carbon atoms, for straight-chain or branched alkynyl with 2 to 8 carbon atoms, stand for straight-chain or branched alkoxy with 1 to 8 carbon atoms or for arylalkyl, aryl or aryloxy with 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl part which are optionally mono- or polysubstituted in the same or different ways , the following being suitable as aryl substituents: Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalky
  • Alkoximinoalkyl each with 1 to 6 carbon atoms in the individual alkyl parts and optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms, phenyl, A stands for a double-linked alkanediyl radical with 1 to 8 carbon atoms and
  • X 1 represents oxygen or sulfur
  • R 4 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl, the following being suitable as substituents:
  • R 4 also for each straight-chain or branched alkenyl or alkynyl each having 2 to 8 carbon atoms, for each straight-chain or branched
  • Haloalkenyl or haloalkynyl each with 2 to 6 carbon atoms and 1 to 11 identical or different halogen atoms - in particular fluorine, chlorine, bromine and / or iodine or for straight-chain or branched alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkoxycarbonyl each with 1 to 8 carbon atoms in stands for the individual alkyl parts, furthermore stands for cycloalkyl with 3 to 8 carbon atoms optionally substituted once or several times, identically or differently by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, and also stands for optionally optionally single or multiple times,
  • the same or different substituted aryl or aryloxy each having 6 to 10 carbon atoms, the following being suitable as aryl substituents:
  • R 5 represents hydrogen, cyano, amino, aminocarbonyl or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl having 1 to 8 carbon atoms, where as
  • R 5 also represents straight-chain or branched alkenyl or alkynyl each having 2 to 8 carbon atoms, each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N, N-dialkylamino or alkylidenimino each having 1 to 8 carbon atoms in the individual alkyl parts, furthermore stands for cycloalkyl with 3 to 8 carbon atoms which is optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms, and additionally for aryl or aryloxy which is monosubstituted or
  • R 6 for each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 8 carbon atoms or for a radical of the formula
  • R 7 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or cycloalkyl having 3 to 8 carbon atoms
  • R 8 and R 9 are each independently of one another in each case for hydrogen, for straight-chain or branched alkyl having 1 to 8 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each with 2 to 8 carbon atoms, for cycloalkyl with 3 to 8 carbon atoms or for each optionally simple or arylalkyl or aryl which are substituted several times, identically or differently, each having 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl part, the following being suitable as aryl substituents: halogen, cyano, nitro, in each case straight-chain or branched alkyl, Alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen
  • R 1 1 either independently of one another in each case for straight-chain or branched alkyl having 1 to 8 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 2 to 8 carbon atoms, for straight-chain or branched haloalkyl having 1 to 6 Carbon atoms and 1 to 13 identical or different halogen atoms - especially fluorine, chlorine, bromine and / or iodine - for each straight-chain or branched haloalkenyl or haloalkynyl each with 2 to 6 carbon atoms and 1 to 1 1 identical or different halogen atoms - especially fluorine, chlorine , Bromine and / or iodine, for each straight-chain or branched
  • Alkoxyalkyl or alkoxy each with 1 to 8 carbon atoms in the individual alkyl parts, for cycloalkyl with 3 to 8 carbon atoms, for cycloalkylalkyl with 3 to 8 carbon atoms in the cycloalkyl part and 1 to 6 carbon atoms in the straight-chain or branched alkyl part, for each optionally one or more times the same or variously substituted
  • Aryl or arylalkyl each having 6 to 10 carbon atoms in the aryl part and optionally 1 to 6 carbon atoms in the straight-chain or branched alkyl part or for heteroaryl with 2 to 9 carbon atoms and 1 to 4 identical or different heteroatoms which are optionally mono- or polysubstituted identically or differently - in particular nitrogen ,
  • Oxygen and / or sulfur are available, aryl and heteroaryl substituents being suitable: Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 6 carbon atoms in the individual alkyl parts and optionally mono- or polysubstituted, identically or differently, by halogen and / or straight-chain or branched alkyl having 1 to 6 carbon atoms; or R 10 and R 1 1 together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which may or may not be mono- or polysubstituted, identically or
  • X 2 represents oxygen or sulfur.
  • Het stands for a heterocycle of the formula or
  • R 1 , R 2 and R 3 independently of one another each represent fluorine, chlorine, bromine, for straight-chain or branched alkyl having 1 to 6 carbon atoms, for straight-chain or branched alkenyl having 2 to 6 carbon atoms, for straight-chain or branched alkynyl having 2 to 6 carbon atoms , for straight-chain or branched alkoxy with 1 to 6 carbon atoms or for in each case optionally monosubstituted to trisubstituted, identically or differently substituted, phenylalkyl, phenyl or phenoxy with optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part, the following being suitable as phenyl substituents:
  • A represents a double-linked alkanediyl radical having 1 to 6 carbon atoms and
  • X 1 represents oxygen or sulfur
  • R 4 represents hydrogen, fluorine, chlorine, bromine, cyano, nitro or straight-chain or branched, optionally monosubstituted alkyl having 1 to 6 carbon atoms, the following being suitable as substituents:
  • R 4 also for each straight-chain or branched alkenyl or alkynyl each having 2 to 6 carbon atoms, for straight-chain or branched haloalkyl having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine, for each straight-chain or branched haloalkenyl or haloalkynyl each having 2 to 4 carbon atoms and 1 to 7 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine or for each straight-chain or branched alkoxy, alkylthio, alkylsulfonyl, alkylsulfonyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the individual Represents alkyl, furthermore represents cycloalkyl having 3 to 7 carbon atoms which is optionally monosubstituted to pentasubstituted identically or differently by chlorine, bro
  • R 5 represents hydrogen, cyano, amino, aminocarbonyl or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl having 1 to 6 carbon atoms, the following being suitable as substituents: fluorine, chlorine, bromine, hydroxy, cyano, amino , each straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each having 1 to 4 carbon atoms in the individual alkyl parts;
  • R 5 also for each straight-chain or branched alkenyl or alkynyl each having 2 to 6 carbon atoms, for each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N, N-dialkylamino or
  • Alkylidenimino each having 1 to 6 carbon atoms in the individual alkyl parts, is also optionally substituted by up to five times, identical or different, by chlorine, bromine, methyl and / or ethyl tes cycloalkyl having 3 to 7 carbon atoms, moreover in each case optionally phenyl or phenoxy which is monosubstituted to trisubstituted by identical or different substituents, the following being suitable as phenyl substituents:
  • R 6 for each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 6 carbon atoms or for a radical of the formula
  • R 7 represents straight-chain or branched alkyl having 1 to 6 carbon atoms or cycloalkyl having 3 to 7 carbon atoms
  • R 8 and R 9 are each independently of one another in each case for hydrogen, for straight-chain or branched alkyl having 1 to 6 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each having 2 to 6 carbon atoms, for cycloalkyl with 3 to 7 carbon atoms or for each optionally simple up to triple, identical or differently substituted phenylalkyl or phenyl with optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part, where the following are in each case possible as phenyl substituents:
  • Chlorine, and / or bromine for straight-chain or branched alkoxyalkyl or alkoxy each having 1 to 6 carbon atoms in the individual alkyl parts, for cycloalkyl with 3 to 7 carbon atoms, for cycloalkylalkyl with 3 to 7 carbon atoms in the cycloalkyl part and 1 to 4 carbon atoms in the straight-chain or branched alkyl part, for phenyl or phenylalkyl which is optionally monosubstituted to trisubstituted in the same or different manner and optionally having 1 to 4 carbon atoms in the straight-chain or branched alkyl part or for heteroaryl having 2 to 9 carbon atoms and monosubstituted or trisubstituted in the same or different ways and 1 to 3 identical or different heteroatoms, in particular nitrogen, oxygen and / or sulfur, where as aryl or.
  • Heteroaryl substituents are possible: Halogen, cyano, nitro, each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, each straight-chain or branched Alkoxycarbonyl or alkoximinoalkyl, each having 1 to 4 carbon atoms in the individual alkyl parts and optionally mono- to triple, identical or different, substituted by halogen and / or straight-chain or branched alkyl having 1 to 4 carbon atoms; or R 10 and R 11 together with the nitrogen atom to which they are attached represent a saturated five- to seven-membered heterocycle which is optionally monosubstituted to tetrasubstantially, identically or differently, by straight-chain or branched alkyl having 1
  • X 2 represents oxygen or sulfur.
  • Het stands for a heterocycle of the formula or
  • R 1 , R 2 and R 3 independently of one another each represent fluorine, chlorine, bromine, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for straight-chain or branched alkenyl having 2 to 4 carbon atoms, for straight-chain or branched alkynyl having 2 to 4 carbon atoms , for straight-chain or branched alkoxy with 1 to 4 carbon atoms or for phenylalkyl, phenyl or phenoxy which are optionally mono- or disubstituted, identically or differently, and optionally with 1 to 3 carbon atoms in the straight-chain or branched alkyl part, the following being suitable as phenyl substituents:
  • A represents a double-linked alkanediyl radical having 1 to 4 carbon atoms and
  • X 1 represents oxygen or sulfur
  • R 4 represents hydrogen, fluorine, chlorine, bromine, cyano, nitro or straight-chain or branched, optionally monosubstituted alkyl having 1 to 4 carbon atoms, the following being suitable as substituents:
  • R 4 also for each straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, for haloalkyl having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine, for each straight-chain or branched haloalkenyl or Haloalkynyl each with 2 to 3 carbon atoms and 1 to 5 identical or different halogen atoms - in particular fluorine, chlorine and / or bromine - or for straight-chain or branched alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl or alkoxycarbonyl each with 1 to 4 carbon atoms in the individual alkyl parts stands, also stands for cycloalkyl with 3 to 6 carbon atoms, also for each optionally single or double, identical or different substituted phenyl or phenoxy, where the following are suitable as phenyl substituent
  • R 5 represents hydrogen, cyano, amino, aminocarbonyl or straight-chain or branched, optionally mono- or polysubstituted, identically or differently substituted alkyl having 1 to 4 carbon atoms, the following being suitable as substituents: fluorine, chlorine, bromine, hydroxy, cyano, amino , in each case straight-chain or branched alkoxy, alkylthio, N-alkylamino or N, N-dialkylamino, each having 1 to 3 carbon atoms in the individual alkyl parts;
  • R 5 also for each straight-chain or branched alkenyl or alkynyl each having 2 to 4 carbon atoms, for each straight-chain or branched alkoxy, alkoxycarbonyl, N-alkylamino, N, N-dialkylamino or
  • Alkylidenimino each having 1 to 4 carbon atoms in the individual alkyl parts also stands for cycloalkyl with 3 to 6 carbon atoms, and also stands for phenyl or phenoxy which is monosubstituted or disubstituted in the same way or differently, the following being suitable in each case as phenyl substituents: Fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, methylthio, ethylthio, trifluoromethyl, difluoromethyl, trifluoromethoxy, difluoromethoxy, trifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, methoximinomethyl, me
  • R 6 for each straight-chain or branched alkyl, alkoxy or alkylthio each having 1 to 4 carbon atoms or for a radical of the formula
  • R 7 represents straight-chain or branched alkyl having 1 to 4 carbon atoms or cycloalkyl having 3 to 6 carbon atoms
  • R 8 and R 9 are each independently of one another in each case for hydrogen, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for each straight-chain or branched alkenyl or alkynyl each with 2 to 4 carbon atoms, for cycloalkyl with 3 to 6 carbon atoms or for each optionally simple or phenylalkyl or phenyl which are substituted twice, identically or differently and optionally have 1 to 3 carbon atoms in the straight-chain or branched alkyl part, where the following are in each case possible as phenyl substituents:
  • Alkoxyalkyl or alkoxy each with 1 to 4 carbon atoms in the individual alkyl parts, for cycloalkyl with 3 to 6 carbon atoms, for cycloalkylalkyl with 3 to 6 carbon atoms in the cycloalkyl part and 1 or 2 carbon atoms in the alkyl part, each optionally mono- or disubstituted, identically or differently substituted Phenyl or phenylalkyl with optionally 1 to 3 carbon atoms in the straight-chain or branched alkyl part or for optionally mono- or disubstituted, identically or differently substituted heteroaryl with 2 to 5 carbon atoms and 1 to 3 identical or different heteroatoms - in particular nitrogen, oxygen and / or sulfur, where aryl or heteroaryl substituents are suitable:
  • X 2 represents oxygen or sulfur.
  • substituted triazolinones of the general formula (I) may be mentioned individually:
  • Formula (II) provides a general definition of the 1-chloro (thio) carbonyltriazolinones required as starting materials for carrying out process (a) according to the invention.
  • Het and ⁇ l preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the compounds of the formula (I) according to the invention.
  • the 1-chloro (thio) carbonyltriazolinones of the formula (II) are known (see, for example, EP 431 390; EP 283 876; EP 298 371).
  • Formula (III) provides a general definition of the amines which are further required as starting materials for carrying out process (a) according to the invention.
  • R 1 , R 2 , R 3 and A preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the compounds of the formula (I) according to the invention.
  • the amines of the formula (III) are known or can be obtained analogously to known processes (cf., for example, J. Amer. Chem. Soc, 73 3867 [1951]; Synth. Commun., 18, (16-17) 1975-1978 ).
  • Formula (IV) provides a general definition of the triazolinones which are unsubstituted in the 1-position to carry out process (b) according to the invention.
  • Het preferably represents those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
  • Formula (V) provides a general definition of the iso (thio) cyanates required to carry out process (b) according to the invention.
  • R 1 , R 2 , R 3 , A and X 1 preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
  • the iso (thio) cyanates of the formula (V) are known or can be obtained analogously to known processes (cf., for example, Zh. Obshch. Khim. 38, 1179-1185 [1968]; Zh. Obshch. Khim. 37, 1383-1385 [1967]; J. Org. Chem. 49, 2688-2691 [1984]).
  • Inert organic solvents are suitable as diluents for carrying out process (a) according to the invention.
  • aliphatic, alicyclic or aromatic optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as
  • Process (a) according to the invention is preferably carried out in the presence of a suitable reaction auxiliary.
  • All conventional inorganic or organic bases are suitable as such. These include, for example, alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide or also ammonium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbonate, alkali metal or alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate, and also ammonium acetate or ammonium acetate Trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicyclound
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and + 150 ° C, preferably at temperatures between + 10 ° C and + 80 ° C.
  • process (a) To carry out process (a) according to the invention, generally 1.0 to 5.0 mol, preferably 1.0 to 2 mol, of amine of the formula (III) and, if appropriate, are used per mol of 1-chloro (thio) carbonyltriazolinone of the formula (II) 1.0 to 5.0 mol, preferably 1.0 to 2 mol, of base as reaction auxiliary.
  • the reaction is carried out, worked up and isolated by known processes (see, for example, EP 283 876 or the preparation examples).
  • Inert organic solvents are suitable as diluents for carrying out process (b) according to the invention.
  • the solvents listed in the description of the implementation of process (a) according to the invention are preferably used.
  • process (b) according to the invention can be carried out in the presence of a suitable basic reaction auxiliary.
  • a suitable basic reaction auxiliary such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, pyridine, piperidine, N-methylpiperidine, N, N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU) are preferably used.
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicycloundecene
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between 0 ° C and + 150 ° C, preferably at temperatures between + 40 ° C and + 120 ° C.
  • Process (b) according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • reaction is carried out, worked up and isolated by known processes (see, for example, EP 283 876 or the preparation examples).
  • the end products of the formula (I) are purified using customary methods, for example by column chromatography or by recrystallization.
  • the characterization is carried out using the melting point or, in the case of non-crystallizing compounds, using proton nuclear magnetic resonance spectroscopy (! H-NMR).
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers become. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can be used, for example, in the following plants:
  • the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.
  • the compounds are suitable for total weed control, for example on industrial and rail tracks and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops for example forest, ornamental wood, fruit, wine, Zi trus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annual crops.
  • the active compounds according to the invention can be used with particularly good success for controlling monocotyledonous and dicotyledon weeds in monocotyledon crops such as, for example, maize.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active ingredient-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • auxiliary solvents include aromatics, such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes, or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide or dimethyl sulfoxide, and water.
  • aromatics such as xylene, toluene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes
  • Solid carrier materials are suitable: for example ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates;
  • Solid carriers for granules are suitable: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks;
  • Possible emulsifying and / or foaming agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl s
  • Adhesives such as carboxymethyl cellulose, natural and synthetic, powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0, 1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides for combating weeds, finished formulations or tank mixes being possible.
  • herbicides are suitable for the mixtures, for example anilides, such as, for example, diflufenican and propanil; Aryl carboxylic acids, such as dichloropicolinic acid, dicamba or picloram; Aryloxyalkanoic acids such as 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones such as chloridazon and norflurazon; Carbamates such as chlorpropham, desmedipham, phenmedipham and propham; Chloroacetanilides such as alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propach
  • a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying; Spray, sprinkle.
  • the active compounds according to the invention can be applied both before and after emergence of the plants.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. Generally lie gene the application rates between 0.01 and 10 kg of active ingredient per hectare of soil, preferably between 0.05 and 5 kg per hectare.
  • precipitated triethylamine hydrochloride is filtered off, the filtrate is concentrated in vacuo, the residue is taken up in 150 ml of dichloromethane, washed three times with 50 ml of water each time, dried over sodium sulfate and again concentrated in vacuo. The residue is recrystallized from cyclohexane.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Seeds of the test plants are sown in normal soil and watered with the active compound preparation after 24 hours.
  • the amount of water per unit area is expediently kept constant.
  • the concentration of active substance in the preparation is irrelevant, the only decisive factor is the amount of active substance applied per unit area.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compound according to Preparation Example 3 shows a clear superiority in effectiveness as well as a considerably improved crop selectivity compared to the prior art.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
  • Test plants which have a height of 5 to 15 cm are sprayed with the active compound preparation in such a way that the desired amounts of active compound are applied per unit area. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • the compound according to Preparation Example 3 shows a clear superiority in effectiveness as well as an improved crop selectivity compared to the prior art.

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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 de nouvelles triazolinones substituées de formule générale (I) dans laquelle Het représente un hétérocycle de formule (a) ou (b) et R?1, R2, R3, A, X1, R4, R5, R6, R7 et X2¿ ont les significations données dans la description, plusieurs procédés pour leur production, et leur utilisation comme herbicides.
EP93921909A 1992-10-12 1993-10-04 Triazolinones substituees Ceased EP0663917A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE4234306 1992-10-12
DE4234306A DE4234306A1 (de) 1992-10-12 1992-10-12 Substituierte Triazolinone
PCT/EP1993/002705 WO1994009012A1 (fr) 1992-10-12 1993-10-04 Triazolinones substituees

Publications (1)

Publication Number Publication Date
EP0663917A1 true EP0663917A1 (fr) 1995-07-26

Family

ID=6470232

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93921909A Ceased EP0663917A1 (fr) 1992-10-12 1993-10-04 Triazolinones substituees

Country Status (8)

Country Link
EP (1) EP0663917A1 (fr)
JP (1) JPH08505837A (fr)
AU (1) AU664780B2 (fr)
BR (1) BR9307225A (fr)
CA (1) CA2146661A1 (fr)
DE (1) DE4234306A1 (fr)
RU (1) RU95113591A (fr)
WO (1) WO1994009012A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6071806B2 (ja) * 2013-08-27 2017-02-01 四国化成工業株式会社 アゾールシラン化合物、該化合物の合成方法及びその利用
US9688704B2 (en) 2013-07-02 2017-06-27 Shikoku Chemicals Corporation Azole silane compound, surface treatment solution, surface treatment method, and use thereof
JP6071780B2 (ja) * 2013-07-02 2017-02-01 四国化成工業株式会社 アゾールシラン化合物、該化合物の合成方法及びその利用

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3723246A1 (de) * 1987-07-14 1989-01-26 Lentia Gmbh Neue thienyl-azolylmethyl-silane
DE4109671A1 (de) * 1991-03-23 1992-09-24 Bayer Ag Substituierte triazolinone
JP2823614B2 (ja) * 1989-12-15 1998-11-11 株式会社日立製作所 階調表示方式および液晶表示装置

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9409012A1 *

Also Published As

Publication number Publication date
CA2146661A1 (fr) 1994-04-28
AU664780B2 (en) 1995-11-30
DE4234306A1 (de) 1994-04-14
RU95113591A (ru) 1996-12-27
JPH08505837A (ja) 1996-06-25
AU5110693A (en) 1994-05-09
BR9307225A (pt) 1999-05-11
WO1994009012A1 (fr) 1994-04-28

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