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WO1996011188A1 - Sulfonylaminocarbonyltriazolinones comprenant des substituants lies par oxygene et soufre - Google Patents

Sulfonylaminocarbonyltriazolinones comprenant des substituants lies par oxygene et soufre Download PDF

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Publication number
WO1996011188A1
WO1996011188A1 PCT/EP1995/003768 EP9503768W WO9611188A1 WO 1996011188 A1 WO1996011188 A1 WO 1996011188A1 EP 9503768 W EP9503768 W EP 9503768W WO 9611188 A1 WO9611188 A1 WO 9611188A1
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Prior art keywords
fluorine
chlorine
alkyl
optionally substituted
alkoxy
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PCT/EP1995/003768
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German (de)
English (en)
Inventor
Klaus Helmut MÜLLER
Klaus König
Hans-Joachim Santel
Markus Dollinger
Klaus Stenzel
Original Assignee
Bayer Aktiengesellschaft
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Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to CA 2201596 priority Critical patent/CA2201596A1/fr
Priority to AU36526/95A priority patent/AU3652695A/en
Priority to JP8512286A priority patent/JPH10508298A/ja
Priority to EP95934107A priority patent/EP0784616A1/fr
Publication of WO1996011188A1 publication Critical patent/WO1996011188A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C337/00—Derivatives of thiocarbonic acids containing functional groups covered by groups C07C333/00 or C07C335/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
    • C07C337/02—Compounds containing any of the groups, e.g. thiocarbazates
    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
    • C07D249/12—Oxygen or sulfur atoms
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to new sulfonylaminocarbonyltriazolinones with substituents bonded via oxygen and sulfur, several ner drives and various new intermediates for their preparation and their use as herbicides and fungicides.
  • Oxygen and sulfur-bonded substituents are known (see the following "disclaimer"). However, the action of these previously known compounds is not satisfactory in all respects.
  • R 1 represents hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, aralkyl,
  • R 2 represents an optionally substituted radical from the series alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, aralkyl, aryl, and
  • R 3 represents an optionally substituted radical from the series alkyl, aralkyl, aryl, heteroaryl, and salts of compounds of the formula (I), where the compounds 4-methoxy-5-methylthio-2- (2-methoxycarbonyl -phenylsulfonyl-aminocarbonyl) -2,4-dihydro-3H-1,2,4-triazol-3-one, 4-ethoxy-5-ethylthio-2- [2- (N-methoxy) -methylaminosulfonyl-phenylsulfonyl-aminocarbonyl ] -2,4-dihydro-3H-1,2,4-triazol-3-one, 4-propoxy-5-allylthio-2- (2-methylphenylsulfonylaminocarbonyl) -2,4-dihydro-3H- 1,2,4-triazol-3-one, 4-methoxy-5-methylthio-2- (2-methoxycarbonylthien-3
  • n, R 1 and R 2 have the meaning given above and Z represents halogen, alkoxy, aralkoxy or aryloxy, with sulfonamides of the general formula (V)
  • R 3 has the meaning given above, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, or if
  • R 3 has the meaning given above and
  • Z represents halogen, alkoxy, aralkoxy or aryloxy, optionally in the presence of an acid acceptor and optionally in
  • R 3 has the meaning given above and
  • X represents halogen, and metal cyanates of the general formula (VIII) MOCN (VIII) in which
  • M represents an alkali metal or alkaline earth metal equivalent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and if appropriate the compounds of the formula (I) obtained by processes (a), (b), (c) or (d) converted into salts by conventional methods.
  • R 2 is propargyl
  • the new sulfonylaminocarbonyltriazolinones with substituents of the general formula (I) bonded via oxygen and sulfur are notable for strong herbicidal and fungicidal activity.
  • the new compounds of the formula (I) have a considerably stronger herbicidal action than structurally similar compounds which are representative of the prior art, such as e.g. the well-known 4-amino-5-methylthio-2- (2-trifluoromethoxy-phenylsulfonyl-aminocarbonyl) -2,4-dihydro-3H-1,2,4-triazol-3-one.
  • the invention preferably relates to compounds of the formula (I) in which n represents the numbers 0, 1 or 2, R 1 is hydrogen, optionally by fluorine, chlorine, bromine, cyano, C 1 -C 4 -alkoxy, C 1 -C 4 alkylcarbonyl or C 1 -C 4 alkoxycarbonyl substituted C 1 - C 6 alkyl, each for C 2 -C 6 alkenyl or C 2 - optionally substituted by fluorine, chlorine and / or bromine C 6 -alkynyl, for C 3 -C 6 -cycloalkyl or in each case optionally substituted by fluorine, chlorine, bromine and / or C 1 -C 4 -alkyl
  • C 5 -C 6 cycloalkenyl or for each optionally by fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 alkyl, trifluoromethyl, C 1 -C 4 alkoxy and / or C 1 -C 4 alkoxy carbonyl-substituted phenyl or phenyl-C 1 -C 3 -alkyl
  • R 2 is optionally fluorine, chlorine, bromine cyano, C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 - Alkylthio or C 1 -C 4 alkoxy-carbonyl substituted C 1 -C 6 alkyl, each for C 2 -C 6 alkenyl or C 2 -C 6 alkynyl optionally substituted by fluorine, chlorine and / or bromine, for each is optionally substituted by fluorine, chlorine, bromine and / or C 1 -C 4
  • R 4 and R 5 are identical or different and are hydrogen, fluorine, chlorine, bromine, iodine, nitro, C 1 -C 6 -alkyl (which may be replaced by fluorine,
  • R 6 for C 1 -C 4 alkyl (which may be replaced by fluorine, chlorine,
  • R 4 and / or R 5 furthermore for phenyl or phenoxy, for C 1 -C 4 alkylcarbonylamino, C 1 -C 4 alkoxycarbonylamino, C 1 -C 4 alkylaminocarbonylamino, di- (C 1 - C 4 alkyl) amino carbonylamino, or for the radical -CO-R 8 , where
  • R 10 is hydrogen or C 1 -C 4 alkyl
  • R 1 1 and R 12 are the same or different and are hydrogen, fluorine, chlorine,
  • R 3 represents the rest
  • R 13 and R 14 are the same or different and are hydrogen, fluorine, chlorine,
  • R 3 represents the rest.
  • R 1 5 and R 16 are the same or different and are hydrogen, fluorine,
  • Farther R 3 represents the rest,
  • R 1 7 and R 18 are the same or different and are hydrogen, fluorine,
  • R 3 represents the rest
  • R 19 and R 20 are the same or different and are hydrogen, fluorine, chlorine, bromine, cyano, nitro, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine), C 1 -C 4 -alkoxy (which is optionally substituted by fluorine and / or chlorine), C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl or C 1 -C 4 -alkylsulfonyl (which is optionally substituted by fluorine and / or chlorine), Di - (C 1 -C 4 -alkyl) -aminosulfonyl, C 1 -C 4 -alkoxy-carbonyl or dimethylaminocarbonyl, and
  • A stands for oxygen, sulfur or the grouping NZ, where Z stands for hydrogen, C 1 -C 4 -alkyl (which may be replaced by fluorine,
  • Chlorine, bromine or cyano is substituted), C 3 -C 6 cycloalkyl, benzyl, phenyl (which may be replaced by fluorine, chlorine, bromine or nitro is substituted), C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl or di- (C 1 -C 4 alkyl) aminocarbonyl;
  • R 3 represents the rest
  • R 21 and R 22 are identical or different and represent hydrogen, C 1 - C 4 alkyl, halogen, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 alkoxy or C 1 - C 4 haloalkoxy stand,
  • Y 1 represents sulfur or the grouping NR 23 , where
  • R 23 represents hydrogen or C 1 -C 4 alkyl
  • R 3 represents the rest
  • R 24 represents hydrogen, C 1 -C 4 alkyl, benzyl, pyndyl, quinolinyl or phenyl
  • R 25 represents hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl (which is optionally substituted by fluorine and / or chlorine is), C 1 -C 4 alkoxy
  • R 26 represents hydrogen, halogen or C 1 -C 4 alkyl, and furthermore R 3 stands for one of the groupings listed below,
  • the invention further preferably relates to sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 alkyl ammonium, di (C 1 -C 4 alkyl) ammonium,
  • the invention relates in particular to compounds of the formula (I) in which n represents the numbers 0, 1 or 2,
  • R 1 for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, for each optionally substituted by fluorine, chlorine or bromine Propenyl, butenyl, propynyl or butynyl, each optionally with fluorine, chlorine, bromine,
  • R 2 for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine, cyano, methoxy, ethoxy, methylthio or ethylthio, for each optionally by fluorine, Chlorine or bromine-substituted propenyl, butenyl, propynyl, butynyl or allenyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclo- butylmethyl, cyclopentylmethyl or cyclohexylmethyl or phenyl or benzyl optionally substituted by fluorine, chlorine, bromine, cyano, methyl, trifluoromethyl or methoxy,
  • R 3 represents the rest
  • R 4 for fluorine, chlorine, bromine, methyl, ethyl, propyl, trifluoromethyl, butoxy,
  • R 3 represents the rest
  • R 10 represents hydrogen
  • R 1 1 represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, methylsulfonyl or dimethylaminosulfonyl and R 12 represents hydrogen;
  • R 3 represents the rest
  • R represents C 1 -C 4 alkyl
  • R 3 represents the rest
  • R 24 stands for C 1 -C 3 alkyl, phenyl or pyridyl
  • R 25 stands for hydrogen, fluorine, chlorine or bromine
  • R 26 stands for fluorine, chlorine, bromine or C 1 -C 3 alkoxycarbonyl, with the exception of the connections excluded by disclaimer above.
  • hydrocarbon radicals mentioned in the radical definitions such as alkyl, alkenyl or alkynyl, also in combinations with heteroatoms, such as in alkoxy, alkylthio or alkylamino, are straight-chain or branched, even if this is not expressly stated.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
  • Formula (II) provides a general definition of the triazolinones to be used as starting materials in processes (a), (c) and (d) for the preparation of compounds of the formula (I).
  • n, R 1 and R 2 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for n, R 1 and R 2 were specified.
  • R 2 has the meaning given above and
  • X represents halogen or the group -O-SO 2 -OR 2 , optionally in the presence of an acid acceptor, such as potassium hydroxide, potassium t-butoxide or potassium carbonate, and optionally in the presence of a diluent, such as methanol or ethanol, at temperatures between 0 ° C and 100 ° C and optionally subsequently oxidized in a conventional manner to corresponding sulfoxides or sulfones (see. The preparation examples).
  • R 1 preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 1 .
  • the preferred metal salts of the compounds of formula (IX) are the alkali metal salts and alkaline earth metal salts, in particular the sodium, potassium, magnesium and
  • the mercapto-triazolinones of the general formula (IX) - and their meta salts - are not yet known from the literature; as new substances, they are also the subject of the present application.
  • the new mercaptotriazolinones of the formula (IX) are obtained when using semicarbazide
  • Y represents halogen, imidazolyl, alkoxy, aralkoxy or aryloxy, optionally in the presence of a reaction auxiliary, e.g. Potassium carbonate, and optionally in the presence of a diluent, e.g. Methanol or ethanol, at temperatures between 20 ° C and 150 ° C (see. The manufacturing examples).
  • a reaction auxiliary e.g. Potassium carbonate
  • a diluent e.g. Methanol or ethanol
  • R 1 preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 1 ;
  • Y preferably represents fluorine, chlorine, bromine, iodine, methoxy, ethoxy,
  • the semicarbazide derivatives of the general formula (XI) are not yet known from the literature; as new substances, they are also the subject of the present application.
  • the new semicarbazide derivatives of the formula (XI) are obtained if semicarbazides of the general formula (XII)
  • X 1 -CS-Y in which Y has the meaning given above and X 1 represents halogen, if appropriate in the presence of an acid acceptor, such as, for example, triethylamine, and if appropriate in the presence of a diluent, such as, for example, methylene chloride, at temperatures between 0 ° C. and 100 ° C. (cf. the preparation examples).
  • an acid acceptor such as, for example, triethylamine
  • a diluent such as, for example, methylene chloride
  • the precursors of the formula (XIII) are known synthetic chemicals.
  • Formula (X) provides a general definition of the alkylating agents required for the preparation of the starting materials of the formula (II).
  • R 2 preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 2 ;
  • X preferably represents fluorine, chlorine, bromine or iodine, in particular chlorine, bromine or iodine.
  • the compounds of formula (X) are known synthetic chemicals.
  • Formula (III) provides a general definition of the sulfonyl isocyanates to be used as starting materials in process (a) according to the invention for the preparation of compounds of the formula (I).
  • R 3 preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R 3 .
  • the starting materials of the formula (III) are known and / or can be prepared by processes known per se (cf. US-P 4127405, US-P 4169719, US-P 4371391, EP-A 7687, EP-A 13480, EP- A 21641, EP-A 23141, EP-A 23422, EP ⁇
  • Formula (IV) provides a general definition of the triazolinone derivatives to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (I).
  • n, R 1 and R 2 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for n, R 1 and R 2 were specified;
  • Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy, phenoxy, halogen or nitro-phenoxy, in particular methoxy, phenoxy or 4-nitro-phenoxy.
  • Z has the meaning given above and Z 1 represents halogen, alkoxy, aralkoxy or aryloxy, optionally in the presence of an acid acceptor, such as potassium t-butoxide, and optionally in the presence of a diluent, such as tetrahydrofuran or dimethoxyethane, at temperatures between 0 ° C and 100 ° C.
  • an acid acceptor such as potassium t-butoxide
  • a diluent such as tetrahydrofuran or dimethoxyethane
  • Formula (V) provides a general definition of the sulfonamides to be used as starting materials in process (b) according to the invention for the preparation of the compounds of the general formula (I).
  • R 3 preferably or in particular has the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R 3 .
  • the starting materials of the formula (V) are known and / or can be prepared by processes known per se (cf.
  • Formula (I) sulfonic acid amide derivatives to be used as starting materials are generally defined by the formula (VI).
  • R 3 preferably or in particular has the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R 3 ;
  • Z preferably represents fluorine, chlorine, bromine,
  • Methoxy, ethoxy, benzyloxy or phenoxy especially for methoxy or phenoxy.
  • the starting materials of the formula (VI) are known and / or can be prepared by processes known per se.
  • R 3 preferably or in particular has the meaning which has already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for R 3 ;
  • X preferably represents fluorine, chlorine or bromine, especially chlorine.
  • the starting materials of the formula (VII) are known and / or can be prepared by processes known per se.
  • Processes (a), (b), (c) and (d) according to the invention for the preparation of the new compounds of the formula (I) are preferably carried out using diluents. Practically all inert organic solvents can be used as diluents.
  • These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and Dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methyl ethyl, methyl isopropyl and methyl isobutyl ketone, esters such as methyl acetate and ethyl ester, nitriles such as, for example Acetonitrile and propionitrile, amides such as e.g. Dimethylformamide, dimethyl
  • all acid binders which can customarily be used for such reactions can be used as reaction auxiliaries or as acid acceptors.
  • Alkali metal hydroxides such as e.g. Sodium and potassium hydroxide, alkaline earth metal hydroxides such as e.g. Calcium hydroxide, alkali carbonates and alcoholates such as sodium and potassium carbonate,
  • Sodium and potassium tert-butoxide also basic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N-dimethylbenzylamine, N, N-dimethyl-aniline, pyridine, 2 , 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 2-ethyl, 4-ethyl and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo [4,3,0] -non-5-ene (DBN), 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU) and 1,4-diazabicyclo [2,2, 2] octane (DABCO).
  • basic nitrogen compounds such as trimethylamine, trieth
  • reaction temperatures can be varied within a wide range in processes (a), (b), (c) and (d). In general, temperatures between -20 ° C and + 100 ° C, preferably at temperatures between
  • the starting materials required in each case are generally used in approximately equimolar amounts. However, it is also possible to use a larger excess of one of the components used in each case.
  • the reactions are generally carried out in a suitable diluent in the presence of an acid acceptor, and the reaction mixture is stirred for several hours at the temperature required in each case. Working up takes place in the method according to the invention
  • salts can be prepared from the compounds of the general formula (I) according to the invention.
  • Such salts are obtained in a simple manner by customary salt formation methods, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base.
  • a suitable solvent e.g. Methylene chloride, acetone, tert-butyl methyl ether or toluene
  • the salts can then be isolated - if appropriate after prolonged stirring - by concentration or suction.
  • the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the compounds for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of dicotyledon weeds in monocotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active compounds of the formula (I) according to the invention also show interesting fungicidal activity against phytopathogenic fungi, in particular against
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, natural and synthetic substances impregnated with active substances, and very fine encapsulations in polymeric substances
  • Formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally 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.
  • Liquid solvents are essentially suitable.
  • Aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone,
  • Solid carrier materials that come into question are, 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, and solid carrier materials for granules are suitable "eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, come as emulsifiers and / or foam-producing agents in question: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sul
  • 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
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
  • known herbicides for example anilides, such as e.g. Diflufenican and Propanil; Aryl carboxylic acids, e.g. Dichloropicolinic acid, dicamba and picloram; Aryloxyalkanoic acids, e.g. 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, e.g.
  • Linuron and metambazthiazuron Hydroxylamines such as alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; Imidazolinones such as imazethapyr, imazamethabenz, imazapyr and imazaquin; Nitriles such as bromoxynil, dichlobenil and ioxynil; Oxyacetamides such as mefenacet; Sulfonylureas, such as amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, Met- sulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuronmethyl, triasulfuron and tribenuron-methyl; Thiol carbamates such as butylates, cycloates, dialallates, EPTC, es
  • 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, spraying,
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 10 g and 10 kg of active ingredient per hectare of soil, preferably between 50 g and 5 kg per ha.
  • Example 62 The compound listed in Table 1 as Example 62 can be produced, for example, as follows:
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, mix 1
  • Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 2000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 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. After 24 hours, the active ingredient preparation is poured onto the floor. 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. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Emulsifier 0.3 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at 20 ° C. and a relative humidity of approx. 70%.
  • Evaluation is carried out 12 days after the inoculation.
  • the compounds according to Preparation Examples 1, 4, 5 and 6 show an efficiency of 100% at an active ingredient concentration of 10 ppm.

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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

De nouvelles sulfonylaminocarbonyltriazolinones avec des substituants liés par oxygène et soufre répondent à la formule (I), dans laquelle n vaut 0, 1 ou 2; R1 désigne hydrogène ou un reste, le cas échéant substitué, du groupe comprenant alkyle, alcényle, alkinyle, cycloalkyle, cycloalcényle, aryle, aralkyle; R2 désigne un reste, le cas échéant substitué, du groupe comprenant alkyle, alcényle, alkinyle, cycloalkyle, cycloalcényle, cycloalkylalkyle, aralkyle, aryle; et R3 désigne un reste, le cas échéant substitué, du groupe comprenant alkyle, aralkyle, aryle, hétéroaryle. Certains composés nouveaux répondant à la formule (I) mais déjà décrits dans EP-A 431291 sont exclus. L'invention concerne également les sels de ces nouveaux composés répondant à la formule (I), plusieurs procédés et divers produits intermédiaires nouveaux utilisés pour la préparation de ces nouveaux composés, ainsi que leur utilisation, le cas échéant sous forme de sels, comme herbicides et fongicides.
PCT/EP1995/003768 1994-10-05 1995-09-22 Sulfonylaminocarbonyltriazolinones comprenant des substituants lies par oxygene et soufre WO1996011188A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA 2201596 CA2201596A1 (fr) 1994-10-05 1995-09-22 Sulfonylaminocarbonyltriazolinones comprenant des substituants lies par oxygene et soufre
AU36526/95A AU3652695A (en) 1994-10-05 1995-09-22 Sulfonylaminocarbonyltriazolinones with substituents bound by oxygen and sulphur
JP8512286A JPH10508298A (ja) 1994-10-05 1995-09-22 酸素及び硫黄を介して結合される置換基を有するスルホニルアミノカルボニルトリアゾリノン類
EP95934107A EP0784616A1 (fr) 1994-10-05 1995-09-22 Sulfonylaminocarbonyltriazolinones comprenant des substituants lies par oxygene et soufre

Applications Claiming Priority (2)

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DEP4435547.5 1994-10-05
DE19944435547 DE4435547A1 (de) 1994-10-05 1994-10-05 Sulfonylaminocarbonyltriazolinone mit über Sauerstoff und Schwefel gebundenen Substituenten

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JP (1) JPH10508298A (fr)
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WO (1) WO1996011188A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997003056A1 (fr) * 1995-07-11 1997-01-30 Bayer Aktiengesellschaft Composes de sulfonylamino(thio)carbonyle herbicides
WO1997046540A1 (fr) * 1996-05-30 1997-12-11 Bayer Aktiengesellschaft Composes de sulfonylamino(thio)carbonyle substitues et leur utilisation comme herbicides
US6297192B1 (en) 1998-01-24 2001-10-02 Bayer Aktiengesellschaft Selective herbicides based on N-aryl-triazoline(thi)ons and N-arlysulfonylamino(thio)carbonyl-triazoline(thi)ons
US6316386B1 (en) 1996-09-23 2001-11-13 Bayer Aktiengesellschaft Selective herbicides based on arylsulphonylaminocarbonyltriazolinones
US6869968B1 (en) 1996-03-21 2005-03-22 Allmirall Prodesfarma S.A. 2-(3H)-oxazolone derivatives and their use as COX-2 inhibitors
US7115543B2 (en) 2000-06-30 2006-10-03 Bayer Cropscience Ag Aryl sulfonyl amino carbonyl triazole based selective herbicides
USRE39607E1 (en) 1995-07-11 2007-05-01 Bayer Aktiengesellschaft Herbicidal sulphonylamino(thio) carbonyl compounds
EP2371823A1 (fr) 2010-04-01 2011-10-05 Bayer CropScience AG Phényl-sulfonylamino-(thio)carbonyltriazolinones substitués par cyclopropyle, leur préparation et leur utilisation comme herbicides et régulateurs de la croissance des plantes

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19525974A1 (de) * 1995-07-17 1997-01-23 Bayer Ag Substituierte Arylsulfonylamino(thio)carbonyltriazolin(thi)one
CN110734433B (zh) * 2018-07-19 2020-09-11 东莞市东阳光农药研发有限公司 三氮唑化合物及其在农业中的应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0341489A1 (fr) * 1988-05-09 1989-11-15 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0422469A2 (fr) * 1989-10-12 1991-04-17 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0431291A2 (fr) * 1989-11-03 1991-06-12 Bayer Ag Sulfonylaminocarbonyl-triazolinones comportant des substituants attachés par du soufre
EP0534266A1 (fr) * 1991-09-25 1993-03-31 Bayer Ag Sulfonylaminocarbonyltriazolones ayant deux substituants liés à l'intermédiaire d'un oxygène

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0341489A1 (fr) * 1988-05-09 1989-11-15 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0422469A2 (fr) * 1989-10-12 1991-04-17 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0431291A2 (fr) * 1989-11-03 1991-06-12 Bayer Ag Sulfonylaminocarbonyl-triazolinones comportant des substituants attachés par du soufre
EP0534266A1 (fr) * 1991-09-25 1993-03-31 Bayer Ag Sulfonylaminocarbonyltriazolones ayant deux substituants liés à l'intermédiaire d'un oxygène

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6525211B1 (en) 1995-07-11 2003-02-25 Bayer Aktiengesellschaft Herbicidal sulphonylamino(thio)carbonyl compounds
USRE39607E1 (en) 1995-07-11 2007-05-01 Bayer Aktiengesellschaft Herbicidal sulphonylamino(thio) carbonyl compounds
US6251831B1 (en) 1995-07-11 2001-06-26 Bayer Aktiengesellschaft Herbicidal sulphonylamino(thio)carbonyl compounds
EP1344771A1 (fr) * 1995-07-11 2003-09-17 Bayer CropScience AG Dérivés d'acide 2-alkoxy-phénylsulfonique comme intermédiaires pour des composés de sulfonylamino(thio)carbonyle herbicides
WO1997003056A1 (fr) * 1995-07-11 1997-01-30 Bayer Aktiengesellschaft Composes de sulfonylamino(thio)carbonyle herbicides
US6869968B1 (en) 1996-03-21 2005-03-22 Allmirall Prodesfarma S.A. 2-(3H)-oxazolone derivatives and their use as COX-2 inhibitors
JP2000514408A (ja) * 1996-05-30 2000-10-31 バイエル・アクチエンゲゼルシヤフト 置換されたスルホニルアミノ（チオ）カルボニル化合物及びその除草剤としての使用
US6677277B1 (en) 1996-05-30 2004-01-13 Bayer Aktiengesellschaft Substituted sulphonyl amino(thio)carbonyl compounds and their use as herbicides
WO1997046540A1 (fr) * 1996-05-30 1997-12-11 Bayer Aktiengesellschaft Composes de sulfonylamino(thio)carbonyle substitues et leur utilisation comme herbicides
US6316386B1 (en) 1996-09-23 2001-11-13 Bayer Aktiengesellschaft Selective herbicides based on arylsulphonylaminocarbonyltriazolinones
US6297192B1 (en) 1998-01-24 2001-10-02 Bayer Aktiengesellschaft Selective herbicides based on N-aryl-triazoline(thi)ons and N-arlysulfonylamino(thio)carbonyl-triazoline(thi)ons
US7115543B2 (en) 2000-06-30 2006-10-03 Bayer Cropscience Ag Aryl sulfonyl amino carbonyl triazole based selective herbicides
EP2371823A1 (fr) 2010-04-01 2011-10-05 Bayer CropScience AG Phényl-sulfonylamino-(thio)carbonyltriazolinones substitués par cyclopropyle, leur préparation et leur utilisation comme herbicides et régulateurs de la croissance des plantes
WO2011120926A1 (fr) 2010-04-01 2011-10-06 Bayer Cropscience Ag Dérivés d'acide 4-cyclopropyl-2-[(5-oxo-4,5-dihydro-1,2,4-triazol-1-yl)-(thio)carbonyl-aminosulfonyl]-benzoïque, procédé de préparation de ces dérivés et utilisation comme herbicides et régulateurs de la croissance des végétaux

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AU3652695A (en) 1996-05-02
DE4435547A1 (de) 1996-04-11
CN1168668A (zh) 1997-12-24
EP0784616A1 (fr) 1997-07-23
JPH10508298A (ja) 1998-08-18

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