WO1999061429A1 - Sulfonyl amino (thio)carbonyl triazolin (thi)ones comportant des substituants alcenyle - Google Patents

Sulfonyl amino (thio)carbonyl triazolin (thi)ones comportant des substituants alcenyle Download PDF

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Publication number
WO1999061429A1
WO1999061429A1 PCT/EP1999/003389 EP9903389W WO9961429A1 WO 1999061429 A1 WO1999061429 A1 WO 1999061429A1 EP 9903389 W EP9903389 W EP 9903389W WO 9961429 A1 WO9961429 A1 WO 9961429A1
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Prior art keywords
alkyl
fluorine
chlorine
alkoxy
optionally substituted
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PCT/EP1999/003389
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German (de)
English (en)
Inventor
Klaus-Helmut Müller
Klaus König
Ernst Rudolf Gesing
Rolf Kirsten
Joachim Kluth
Markus Dollinger
Mark Wilhelm Drewes
Ingo Wetcholowsky
Gerd Hänssler
Klaus Stenzel
Randy Allen Myers
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Bayer Aktiengesellschaft
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Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to AU41444/99A priority Critical patent/AU4144499A/en
Priority to CA002333068A priority patent/CA2333068A1/fr
Priority to BR9910667-1A priority patent/BR9910667A/pt
Priority to JP2000550835A priority patent/JP2002516316A/ja
Priority to KR1020007012670A priority patent/KR20010043551A/ko
Priority to EP99924995A priority patent/EP1082312A1/fr
Publication of WO1999061429A1 publication Critical patent/WO1999061429A1/fr
Priority to HK02101425.1A priority patent/HK1039936A1/zh

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • 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
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles

Definitions

  • the invention relates to new sulfonylamino (thio) carbonyltriazolin (thi) ones with alkenyl substituents, several processes and new intermediates for their preparation and their use as crop treatment agents, in particular as herbicides and as fungicides.
  • Ql represents oxygen or sulfur
  • Q ⁇ represents oxygen or sulfur.
  • R.1 for hydrogen, amino, alkylidene amino or for an optionally substituted radical from the series alkyl, alkenyl. Alkynyl. Alkoxy.
  • R2 represents optionally substituted alkenyl and
  • R ⁇ represents an optionally substituted radical from the series alkyl, aralkyl, aryl and heteroaryl.
  • Z represents halogen, alkoxy, aralkoxy or aryloxy
  • R 3 has the meaning given above
  • Z represents halogen, alkoxy, aralkoxy or aryloxy.
  • R J has the meaning given above and
  • X represents halogen
  • M represents an alkali metal or an alkaline earth metal equivalent.
  • R preferably represents hydrogen, amino, C for Cj-Cg-alkyl optionally substituted by fluorine, chlorine, bromine, cyano, C -C4-alkoxy, C [-C4-alkylcarbonyl or C ⁇ -C4-alkoxycarbonyl, for each optionally by fluorine, chlorine and / or bromine-substituted C 2 -Cg alkenyl or C -C -C alkynyl, for C 1 -Cg alkyloxy or C 2 -Cg alkenyloxy, for C j -Cg alkylamino optionally substituted by fluorine and / or chlorine, di- (-C-C4-alkyl) -amino or C-C4-alkyl-carbonylamino, for each optionally by fluorine, chlorine.
  • R 2 preferably represents Co-Cg-alkenyl optionally substituted by cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, Cj-C4-A_koxy or C ⁇ -C4-alkoxy-carbonyl.
  • R 3 preferably represents the grouping, where
  • R and R are the same or different and are hydrogen, fluorine, chlorine, bromine. Iodine. Nitro, C j-Cg-alkyl (which may be replaced by fluorine,
  • Chlorine Bromine, cyano, carboxyl, Cj-C4-alkoxycarbonyl, Cj-C4 alkyl amino-carbonyl, di- (C ⁇ -C4-alkyl) -amino-carbonyl, C [-C 4 alkoxy,
  • C 2 -C 6 alkynyl which is optionally substituted by fluorine, chlorine, bromine, cyano, C 1 -C 4 alkoxycarbonyl or phenyl
  • C1 -C4 alkoxy which is optionally substituted by fluorine , Chlorine, bromine, cyano, -C 4 -C 4 alkoxycarbonyl, C1 -C4 alkoxy, -C 4 -C 4 alkylthio, -C 4 -C 4 alkylsulfonyl, -C 4 -C 4 alkylsu_fonyl
  • C j -C ⁇ alkylthio which is optionally by fluorine, chlorine, bromine, cyano, -C -C4-alkoxycarbonyl, -C-C4-alkylthio, C ⁇ -C4-alkylsulfionyl or C 1 -C 4 alkyl sulfonyl is substituted
  • C -Cg alkenyloxy which 'ses- if by fluorine, chlorine, bromine, cyano or C -C 4 alkox carbonyl
  • R for C1-C4-alkyl (which may be replaced by fluorine, chlorine.
  • Cyano C1-C4 alkoxy, -C-C4-alkylthio, C ⁇ . -C4-alkyl-sulfinyl, C
  • C3-Cö-alkali yl (which is optionally substituted by fluorine, chlorine or bromine), C3-Cö-alkali yl, Cß-Cg-cycloalkyl, C3-Cö-cyclo-a_kyl-C ⁇ -C 2 alkyl, phenyl-C ⁇ -C 2 alkyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy or C] -C4-alkoxy-carbonyl), for
  • R ö for hydrogen, C ⁇ Cg-alkyl, C3-C 6 -cycloalkyl, C ⁇ Cg-
  • Alkylthio, -C-C4-alkylamino. C1 -C4- alkoxy amino, C 1 -C4- alkoxy -CC-C4-alkylamino or di- (C 1-C4-alkyD-am.no (which are optionally substituted by fluorine and / or chlorine), R and / or R furthermore for trimethylsilyl, thiazolinyl, l, 2,4-oxadiazol-5-yl, 3-methyl-l, 2,4-oxadiazol-5-yl, l, 3-dioxolan-2-yl, C. j -C4-alkyl-sulfonyloxy, di- (-C-C4-alkyl) -aminosulfonylamino or for the rest g -CH NR, where
  • Alkenyl or C3-Cg-alkynyl for optionally by fluorine, chlorine, bromine, Cj-C4-alkyl, C] -C4-alkoxy, trifluoromethyl,
  • Trifluoromethoxy or trifluoromethylthio substituted phenyl for optionally substituted by fluorine and / or chlorine Cj-Cg-alkoxy, C3-Cg-alkenyloxy, C3-C-alkynyloxy or
  • Benzyloxy for amino, C1-C4- alkylam.no, di- (-C-C4-alkyl) - amino. Phenylamino, -C-C4-alkyl-carbonylamino. C1-C4 alkoxy carbonylamino. C 4 -C 4 alkylsulfonylamino or phenylsulfonylamino which is optionally substituted by fluorine, chlorine, bromine or methyl.
  • R J is also preferred
  • R 10 represents hydrogen or C - C ⁇ - alkyl
  • R 11 and R 12 are the same or different and are hydrogen
  • C1-C4- alkyl (which is optionally substituted by fluorine and / or chlorine), C1 - C4-alkoxy (which is optionally substituted by fluorine and / or chlorine), carboxy, C 1 -C4-alkoxycarbonyl, dimethylaminocarbonyl, C ⁇ -C4-alkylsulfonyl or di- (C - C4-alkyl) -aminosulfonyl.
  • R J is also preferred
  • R and R are the same or different and represent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C 1 -C 4 -alkyl (which is optionally substituted by fluorine and / or chlorine) or C1-C4-alkoxy (which is optionally substituted by fluorine and /or
  • R J is also preferred wherein
  • R and R are the same or different and are hydrogen, fluorine, chlorine, bromine, nitro, cyano, C1-C4-alkyl (which is optionally substituted by fluorine and / or chlorine), C ⁇ - C4-alkoxy (which is optionally substituted by fluorine and / or chlorine is substituted), for C -C4 alkylthio.
  • R 3 is also preferred
  • R 17 and R 18 are the same or different and are hydrogen
  • R 3 is also preferred
  • R and R are the same or different and represent hydrogen
  • A stands for oxygen, sulfur or the grouping N-T, where
  • C3-C-cycloalkyl benzyl, phenyl (which may be replaced by fluorine, chlorine, bromine or nitro is substituted), C -C4-alkylcarbonyl, -C-C4-alkoxycarbonyl or di- (C -C4-alkyl) -aminocarbonyl.
  • R 3 is also preferred
  • R 21 and R 22 are the same or different and represent hydrogen, C
  • R represents hydrogen or C 1 -C 4 alkyl.
  • R 3 is also preferred
  • R 24 is hydrogen, C -C 4 alkyl. Benzyl. Pyridyl, quinolinyl or phenyl,
  • Chlorine is substituted), dioxolanyl or -CC-C4-alkoxycarbonyl, and
  • f R represents hydrogen, halogen or C 1 -C 4 alkyl.
  • the invention further preferably sodium, potassium, magnesium, calcium, ammonium, -C-C4 ⁇ alkyl ammonium.
  • R, R 2 and R 3 have the meanings preferably given above.
  • R stands in particular for fluorine, if appropriate. Chlorine, cyano, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, for propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine, chlorine or bromine, for methoxy, ethoxy, n- or i-propoxy or for Allyloxy. for methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, or for optionally by fluorine, chlorine. Bromine. Methyl or ethyl substituted cyclopropyl, R 2 stands in particular for ethenyl, propenyl or butenyl optionally substituted by cyano, fluorine, chlorine and / or bromine.
  • R 3 stands in particular for the rest
  • 2,2,2-trifluoro-ethoxy 1, 1, 2,2-tetrafluoro-ethoxy, 1, 1, 2,2,2-pentafluoro-ethoxy, 2-methoxy-ethoxy, cyclopropylmethoxy, methylthio, ethylthio, n- or i-propylthio, 2-fluoro-ethylthio, allyloxy, propargyloxy,
  • R represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy,
  • Trifluoromethoxy, methylthio or ethylthio Trifluoromethoxy, methylthio or ethylthio.
  • R 3 stands in particular for
  • R 10 represents hydrogen
  • R represents fluorine, chlorine, bromine, methyl, methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl, ethoxycarbonvl, methvlsulfonvl or dimethylaminosulfonyl
  • R stands for hydrogen
  • R J stands in particular for the rest
  • R for methyl, ethyl. is n- or i-propyl.
  • R 3 stands in particular for the rest
  • R 4 represents methyl, ethyl, n- or i-propyl, phenyl or pvridyl.
  • R ⁇ represents hydrogen, fluorine, chlorine or bromine, and
  • R 2 ⁇ represents fluorine, chlorine, bromine, methoxycarbonyl or ethoxycarbonyl.
  • radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, that is to say also between the specified ranges of preferred compounds.
  • Preferred compounds according to the invention are those of the formula (I) in which there is a combination of the meanings listed above as preferred.
  • those compounds of the formula r ⁇ ) are particularly preferred in which there is a combination of the meanings listed above as being particularly preferred.
  • hydrocarbon radicals mentioned in the radical definitions such as alkyl, alkenyl or alkynyl, also in combinations with heteroatoms. as in alkoxy.
  • Alkylthio or alkylamino even if this is not expressly stated, can be straight-chain or branched.
  • Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine. Chlorine or bromine, especially for fluorine or chlorine.
  • Formula (II) provides a general definition of the triazolin (thi) ones to be used as starting materials in processes (a), (c) and (d) for the preparation of compounds of the formula (I).
  • R 2 has the meaning given above
  • diluents e.g. Isopropanol or water
  • reaction auxiliary e.g. Sodium hydroxide
  • R and Ql have the meaning given above.
  • R 2 has the meaning given above and
  • Y stands for hydroxy, halogen or the grouping -O-CO-R-.
  • a diluent e.g. Sulfolane
  • a reaction auxiliary e.g. Sodium hydroxide
  • a stabilizer such as e.g. Hydroquinone. reacted at temperatures between 0 ° C and 100 ° C and worked up in the usual way (cf. the manufacturing examples).
  • Formula (I) sulfonyliso (thio) cyanates to be used as starting materials are generally defined by the formula (III).
  • Q 2 and R 3 preferably or in particular have those meanings. which have already been given above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for Q 2 and R 3 .
  • EP-A 7687 EP-A 13480.
  • EP-A 21641 EP-A 23141.
  • EP-A 30139 EP-A 35893, EP-A 44808, EP-A 44809, EP-A 48143.
  • (I) were indicated as preferred or as particularly preferred for Q, Q 2 , R and R 2 ;
  • Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.
  • Z represents halogen (especially chlorine), alkoxy (especially methoxy), aralkoxy (especially benzyloxy) or aryloxy (especially phenoxy).
  • an acid acceptor such as sodium or potassium hydride, sodium or potassium hydroxide, sodium or potassium t-butoxide
  • a diluent such as tetrahydrofuran or dimethoxvethane, or in a two-phase system of water and an organic solvent , such as methylene chloride or chloroform, at
  • Formula (V) provides a general definition of the sulfonic acid amides 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. US Pat. No. 4,127,405, US Pat. No. 4,169,719, US Pat. No. 4,37,1391, EP-A 7687, EP-A 13480, EP-A 21641, EP-A 23141, EP-A 23422, EP-A 30139, EP-A 35893, EP-A 44808, EP-A 44809, EP-A 48143, EP-A 51466, EP-A 64322, EP-A 70041, EP-A 173312).
  • Formula (VI) provides a general definition of the sulfonamide derivatives to be used as starting materials in process (c) according to the invention for the preparation of the compounds of the formula (I).
  • Q 2 and R 3 preferably or in particular have those meanings which have already been given above in connection with the description of the compounds of the formula (I) as preferred or as particularly preferred for Q 2 and R 3 were;
  • Z preferably represents fluorine, chlorine, bromine, methoxy, ethoxy, benzyloxy or phenoxy, in particular methoxy or phenoxy.
  • the starting materials of the formula (VI) are known and or can be prepared by processes known per se.
  • Formula (VII) provides a general definition of the sulfonic acid halides to be used as starting materials in process (d) according to the invention for the preparation of the compounds of the 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 ;
  • X preferably represents fluorine. Chlorine or bromine, especially for chlorine.
  • the starting materials of the formula (VII) are known and / or can be prepared by processes known per se.
  • R. R 2 and Q have the meanings given above for formula (I) and A represents hydrogen or the group -CQ 2 -Z, wherein
  • 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.
  • diluents Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons such as
  • reaction auxiliaries or as acid acceptors in the processes (a), (b), (c) and (d) according to the invention it is possible to use all acid binders which can customarily be used for such reactions.
  • Alkali metal hydroxides such as sodium and potassium hydroxide are preferred.
  • Alkaline earth metal hydroxides such as calcium hydroxide.
  • Alkali carbonates and alko-olates such as sodium and potassium carbonate, sodium and potassium tert-butoxide, and also basic nitrogen compounds such as trimethylamine, triethylamine.
  • DBN 1,5-diazabicyclo [4,3,0] non-5-ene
  • DBU 1,8-diazabicyclo - [5.4.0] -undec
  • 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 0 ° C and + 80 ° C.
  • Processes (a), (b), (c) and (d) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to work under increased or reduced pressure.
  • 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 in the processes (a), (b), (c) and (d) according to the invention is in each case carried out by customary methods (cf. the preparation examples).
  • 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, such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding a suitable base.
  • a suitable solvent such as, for example, 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, herbicides and especially as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up 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 e.g. can be used in the following plants:
  • Dicot weeds of the genus Sinapis. Lepidium. Galium. Stellaria. Matricaria.
  • 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 pastures and for selective weed control in annual crops.
  • the compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops both in the pre-emergence and in the post-emergence process.
  • the active compounds according to the invention also have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
  • the active ingredients are suitable in suitable concentrations for use as fungicides and / or bactericides.
  • Fungicidal agents in crop protection are used to control plasmidiophoromycetes, oomycetes and chytridiomycetes. Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Bactericidal agents are used in plant protection to combat Pseudomonadaeae, Rhizobiaceae. Enterobacteriaceae. Corynebacteriaceae and Streptomycetaceae used.
  • Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae;
  • Pseudomonas species such as Pseudomonas syringae pv. Lachrymans;
  • Erwinia species such as, for example, Erwinia amylovora;
  • Pyfhium species such as, for example, Pythium ultimum
  • Phytophthora species such as Phytophthora infestans
  • Pseudoperonospora species such as Pseudoperonospora humuli or
  • Plasmopara species such as, for example, Plasmopara viticola
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae:
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as Sphaerotheca fuliginea:
  • Podosphaera species such as Podosphaera leucotricha:
  • Venturia species such as Venturia inaequalis
  • Pyrenophora species such as Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera. Syn: Helminthosporium); Cochliobolus species, such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendiculatus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Botrytis species such as, for example, Botrytis cinerea
  • Septoria species such as, for example, Septoria nodorum
  • Leptosphaeria species such as, for example, Leptosphaeria nodorum;
  • Cercospora species such as, for example, Cercospora canescens
  • Alternaria species such as, for example, Alternaria brassicae;
  • Pseudocercosporella species such as, for example, Pseudocercosporella he ⁇ otrichoides.
  • the fact that the active compounds are well tolerated by plants in the concentrations required to combat plant diseases permits treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.
  • the active compounds according to the invention can be used with good success to combat diseases in fruit and vegetable production, for example against Podosphaera species, and to combat rice diseases, for example Pyricularia oryzae (protective and systemic).
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions. Powder. Dusts, pastes, soluble powders, granules, suspension emulsion concentrates. Active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene. or alkyl naphthalenes.
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes.
  • Chloroethylene 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.
  • Methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone strongly polar
  • Solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are: for example ammonium salts and natural rock powders such as kaolins, clays, talc. Chalk, quartz. Attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: eg broken and fractionated natural rocks such as calcite,
  • emulsifying and / or foaming agents are possible: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters.
  • polyoxyethylene fatty alcohol such as polyoxyethylene fatty alcohol
  • Ether e.g. Alkylaryl polyglycol ether. Alkyl sulfonates. Alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite leaching and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments can be used. 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 compound, 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 are suitable for the mixtures, for example
  • Acetochlor Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne.
  • Amidochlor amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone,
  • Benzofenap Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim. Butylates.
  • Cafenstrole caloxydim, carbetamide.
  • Carfentrazone (-ethyl), Chlomethoxvfen, Chloramben, Chloridazon, Chlorimuron (-ethyl). Chloronitrofen, chlorosulfuron. Chlortoluron, Cin- methylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop,
  • Clopyralid Clopyrasulfuron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamuron. Cycloxydim, cyhalofop (-butyl), 2.4-D. 2.4-DB, 2,4-DP, desmedipham, dialates, dicamba, diclofop (-methyl), diclosulam, diethyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate. Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine.
  • Fluoroglycofen (ethyl), flupoxam. Flupropacil. Flu ⁇ yrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flu ⁇ rimidol, Flurtamone, Fluothiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (- isopropyl , Halosafen. Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr,
  • Pentoxazone Phenmedipham, Piperophos, Pretilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulftiron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuron- (ethyl), Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-methyl), Pyrithiobac (- sodium), Quinchlorac. Quinmerac.
  • the active compounds as such in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions. Powders, pastes and granules can be used. They are used in the usual way, e.g. by pouring. Splash, spray. Scatter.
  • 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 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • N, N-dimethyl-benzene-1,2-disulfonamide are taken up in 30 ml of toluene and at room temperature (approx. 20 ° C) with 1.52 g (10 mmol) of 1,8-diaza- bicyclo- [5,4,0] -undec-7-ene (DBU) added.
  • DBU 1,8-diaza- bicyclo- [5,4,0] -undec-7-ene
  • the isomer composition of the end product (I) obtained is given in percent (%) (determined from the respective iH-NMR spectrum).
  • the indication means
  • trans / cis 72:28 for the active substance concerned an isomer composition of 72% trans and 28% cis isomer.
  • the product solidifies (melting point: 94 ° C); it consists of 81.5% of the trans isomer and 18.5% of the cis isomer.
  • the isomer mixture can be omitted Recrystallize about twice the amount of ethyl acetate and then provides about 130 g of pure trans isomer (II-1) with a melting point of 112 ° C.
  • a mixture of 178 g (2.0 mol) of 4-methyl-semicarbazide, 10 g of hydroquinone and 250 ml of sulfolane is mixed with 339 g (2.0 mol) of methacrylic anhydride while cooling with ice; the reaction mixture is kept for a further 15 minutes at room temperature (approx.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amounts of active ingredient are applied per unit area.
  • the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 1000 l of water / ha.
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Active ingredient according to effortWeiBaumGalin- Portu- Stel- Manufacturing sample no. amount (g zen wool soga laca laria ai./ha)
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Test plants which have a height of 5-15 cm are sprayed with the active substance preparation, so that the desired amounts of active substance are applied per unit area.
  • the concentration of the spray liquor is chosen so that in
  • the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
  • Emulsifier 3 parts 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.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%
  • Emulsifier 0.06 part by weight of alkylaryl polyglycol ether #
  • Emulsifier 0.06 part by weight of alkylaryl polyglycol ether
  • Evaluation is carried out 4 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%
  • Active ingredient Application rate of effectiveness Active ingredient in g / ha in%

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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 sulfonyl amino (thio)carbony ltriazolin (thi)ones comportant des substituants alcényle, correspondant à la formule (I), dans laquelle: Q1 représente oxygène ou soufre; Q2 représente oxygène ou soufre; R1 représente hydrogène, amino, alkylidénamino ou bien un reste, éventuellement substitué, du groupe alkyle, alcényle, alkynyle, alcoxy, alcényloxy, alkylamino, dialkylamino, alcanoylamino, cycloalkyle, cycloalkylalkyle, cycloalkylamino, aryle et arylalkyle; R2 représente alcényle éventuellement substitué; et R3 représente un reste, éventuellement substitué, du groupe alkyle, aralkyle, aryle et hétéroaryle. L'invention concerne également des sels desdits composés de formule (I), ainsi qu'un procédé et de nouveaux produits intermédiaires pour la production desdits composés de formule (I), et l'utilisation de ceux-ci comme herbicides et/ou fongicides.
PCT/EP1999/003389 1998-05-23 1999-05-17 Sulfonyl amino (thio)carbonyl triazolin (thi)ones comportant des substituants alcenyle WO1999061429A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU41444/99A AU4144499A (en) 1998-05-23 1999-05-17 Sulfonyl amino (thio)carbonyl triazoline (thi)ons having alkenyl substituents
CA002333068A CA2333068A1 (fr) 1998-05-23 1999-05-17 Sulfonyl amino (thio)carbonyl triazolin (thi)ones comportant des substituants alcenyle
BR9910667-1A BR9910667A (pt) 1998-05-23 1999-05-17 Sulfonilamino(tio)carbonil triazolin(ti)ona com substituintes alquenila
JP2000550835A JP2002516316A (ja) 1998-05-23 1999-05-17 アルケニル置換基を有するスルホニルアミノ（チオ）カルボニルトリアゾリン（チ）オン類
KR1020007012670A KR20010043551A (ko) 1998-05-23 1999-05-17 알케닐 치환체를 갖는 설포닐 아미노 (티오)카보닐트리아졸린 (티)온
EP99924995A EP1082312A1 (fr) 1998-05-23 1999-05-17 Sulfonyl amino (thio)carbonyl triazolin (thi)ones comportant des substituants alcenyle
HK02101425.1A HK1039936A1 (zh) 1998-05-23 2002-02-25 具有鏈烯基取代基的磺酰基氨基(硫代)羰基三唑啉(硫)酮

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19823131.8 1998-05-23
DE19823131A DE19823131A1 (de) 1998-05-23 1998-05-23 Sulfonylamino(thio)carbonyltriazolin(thi)one mit Alkenyl-Substituenten

Publications (1)

Publication Number Publication Date
WO1999061429A1 true WO1999061429A1 (fr) 1999-12-02

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Country Status (9)

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EP (1) EP1082312A1 (fr)
JP (1) JP2002516316A (fr)
KR (1) KR20010043551A (fr)
CN (1) CN1311783A (fr)
AU (1) AU4144499A (fr)
CA (1) CA2333068A1 (fr)
DE (1) DE19823131A1 (fr)
HK (1) HK1039936A1 (fr)
WO (1) WO1999061429A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6660677B1 (en) 1997-03-10 2003-12-09 Eastman Chemical Company Supported group 8-10 transition metal olefin polymerization catalysts
US6822062B2 (en) 1997-03-10 2004-11-23 Eastman Chemical Company Supported group 8-10 transition metal olefin polymerization catalysts
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
CN103130731A (zh) * 2013-03-06 2013-06-05 陕西科技大学 一种制备4-氨基-5-芳基-1,2,4-三唑-3-硫酮的方法
US11279686B2 (en) 2016-02-03 2022-03-22 Rigel Pharmaceuticals, Inc. Nrf2 activating compounds and uses thereof

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1717228A1 (fr) * 2005-04-28 2006-11-02 Bayer CropScience GmbH Dérivés de sulfonylamino(thio)carbonyl comme herbicides et regulateurs de la croissance végétale
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 (6)

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US4400517A (en) * 1976-11-17 1983-08-23 Montedison S.P.A. Phosphoric esters derived from 1,2,4-triazole having an insecticidal, nematocidal and acaricidal action, and their preparation
EP0341489A1 (fr) * 1988-05-09 1989-11-15 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0422469A2 (fr) * 1989-10-12 1991-04-17 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0507171A1 (fr) * 1991-04-04 1992-10-07 Bayer Ag Sulfonylaminocarbonyltriazolinones avec des substituants liés par l'oxygène
EP0617025A1 (fr) * 1993-03-24 1994-09-28 Nippon Paint Co., Ltd. Dérivés du triazole, intermédiaires pour leur préparation, et leur procédé de préparation
DE19502579A1 (de) * 1995-01-27 1996-08-01 Bayer Ag Sulfonylamino(thio)carbonyl-triazolin(thi)one

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4400517A (en) * 1976-11-17 1983-08-23 Montedison S.P.A. Phosphoric esters derived from 1,2,4-triazole having an insecticidal, nematocidal and acaricidal action, and their preparation
EP0341489A1 (fr) * 1988-05-09 1989-11-15 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0422469A2 (fr) * 1989-10-12 1991-04-17 Bayer Ag Sulfonylaminocarbonyltriazolinones
EP0507171A1 (fr) * 1991-04-04 1992-10-07 Bayer Ag Sulfonylaminocarbonyltriazolinones avec des substituants liés par l'oxygène
EP0617025A1 (fr) * 1993-03-24 1994-09-28 Nippon Paint Co., Ltd. Dérivés du triazole, intermédiaires pour leur préparation, et leur procédé de préparation
DE19502579A1 (de) * 1995-01-27 1996-08-01 Bayer Ag Sulfonylamino(thio)carbonyl-triazolin(thi)one
WO1996022982A1 (fr) * 1995-01-27 1996-08-01 Bayer Aktiengesellschaft Derives sulfonylamino(thio)carbonyl-1,2,4-triazoline(thi)ones, leur preparation et leur utilisation comme herbicides

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6660677B1 (en) 1997-03-10 2003-12-09 Eastman Chemical Company Supported group 8-10 transition metal olefin polymerization catalysts
US6822062B2 (en) 1997-03-10 2004-11-23 Eastman Chemical Company Supported group 8-10 transition metal olefin polymerization catalysts
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
CN103130731A (zh) * 2013-03-06 2013-06-05 陕西科技大学 一种制备4-氨基-5-芳基-1,2,4-三唑-3-硫酮的方法
US11279686B2 (en) 2016-02-03 2022-03-22 Rigel Pharmaceuticals, Inc. Nrf2 activating compounds and uses thereof

Also Published As

Publication number Publication date
CA2333068A1 (fr) 1999-12-02
HK1039936A1 (zh) 2002-05-17
EP1082312A1 (fr) 2001-03-14
JP2002516316A (ja) 2002-06-04
KR20010043551A (ko) 2001-05-25
DE19823131A1 (de) 1999-11-25
CN1311783A (zh) 2001-09-05
AU4144499A (en) 1999-12-13

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