EP0000752B1 - Alpha-azolysulfide, -sulfoxide und -sulfone, deren Salze und Metallkomplexe, Verfahren zu ihrer Herstellung, sowie sie enthaltende Mittel zur Pilzbekämpfung - Google Patents

Alpha-azolysulfide, -sulfoxide und -sulfone, deren Salze und Metallkomplexe, Verfahren zu ihrer Herstellung, sowie sie enthaltende Mittel zur Pilzbekämpfung Download PDF

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Publication number
EP0000752B1
EP0000752B1 EP78100538A EP78100538A EP0000752B1 EP 0000752 B1 EP0000752 B1 EP 0000752B1 EP 78100538 A EP78100538 A EP 78100538A EP 78100538 A EP78100538 A EP 78100538A EP 0000752 B1 EP0000752 B1 EP 0000752B1
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EP
European Patent Office
Prior art keywords
sulfide
chlorophenyl
weight
triazol
parts
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.)
Expired
Application number
EP78100538A
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German (de)
English (en)
French (fr)
Other versions
EP0000752A3 (en
EP0000752A2 (de
Inventor
Hubert Dr. Sauter
Ernst-Heinrich Dr. Pommer
Bernd Dr. Zeeh
Costin Dr. Rentzea
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BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0000752A2 publication Critical patent/EP0000752A2/de
Publication of EP0000752A3 publication Critical patent/EP0000752A3/xx
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Publication of EP0000752B1 publication Critical patent/EP0000752B1/de
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • 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
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages

Definitions

  • the invention relates to new ⁇ -azolyl sulfides, ⁇ -azolyl sulfoxides and a-azolyl sulfones and their salts and metal complexes, processes for their preparation and agents for combating fungi containing them.
  • imidazole derivatives for example 1- [2,4-dichlorophenyl- ⁇ -allylethyl ether] imidazole (DE-OS 2063857)
  • the effect is not always satisfactory at low application rates and application concentrations.
  • the fungitoxic effect is often associated with a high level of phytotoxicity, so that the crops are also damaged in the concentrations required for combating rust fungi. For these reasons, they are not always suitable for use as crop protection agents for combating fungi and not for all types of plants.
  • R 1 means, for example, hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, n-hexyl, n-heptyl (3), methoxycarbonyl, phenyl, 4-nitrophenyl, 4-bromophenyl, 4-cyanophenyl , 2-methylphenyl, 4-t-butylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl, 4-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,6-dichlorophenyl, 3,4-dichlorophenyl, - Naphthyl.
  • R 2 means, for example, hydrogen, methyl, n-propyl.
  • R 3 means, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, n-pentyl, n-hexyl, allyl, propargyl, phenyl, 4-methoxyphenyl, 4-tolyl, 4-chlorophenyl, 3, 4-dichlorophenyl, 2,4-dichlorophenyl, 2,3,6-trichlorophenyl, benzyl, 3-trifluoromethylbenzyl, 4-chlorobenzyl, 4-bromobenzyl, 3,4-dichlorobenzyl, 2,4-dichlorobenzyl, 2,3,6- Trichlorobenzyl, 2-phenylethyl.
  • salts are the hydrochlorides, bromides, sulfates, nitrates, phosphates, oxalates or dodecylbenzenesulfonates.
  • the effectiveness of the salts is due to the cation, so that the choice of the anion is arbitrary.
  • a diluent such as methanol, ethanol, isopropanol, n-butanol, diethyl ether, tetrahydrofuran, dioxane, acetone, acetonitrile, dimethylformamide, dimethyl sulfoxide, chloroform, methylene chloride or toluene can be used.
  • Potassium permanganate, hydrogen peroxide or percarboxylic acids such as peracetic acid, perbenzoic acid or 3-chloroperbenzoic acid can be used as the oxidizing agent.
  • a diluent such as water, acetic acid, methanol, acetone, chloroform or methylene chloride can be used.
  • the metal salts of formula IV are well known, easily accessible compounds.
  • All water-miscible solvents are suitable for the preparation of the metal complexes of the formula II. These preferably include methanol, ethanol, isopropanol, acetone, tetrahydrofuran and dioxane. It is generally carried out at temperatures between 0 and 100 ° C, preferably between 10 and 35 ° C.
  • separation of the enantiomers or diastereomers is normally not required for use as fungicides or as an agent for regulating plant growth.
  • a solution of 6.0 g of 1-pentyl- [1- (1,2,4-triazol-1-yl) pentyl is added dropwise to the solution of 10.0 g of 85 percent 3-chloroperbenzoic acid in 140 ml of methyl chloride with stirring and ice-cooling - (1)] - sulfide. After the initial heating has subsided, the mixture is stirred for a further 2 days at 25 ° C. The mixture is then washed with sodium carbonate solution, sodium sulfite solution and water and the organic phase is dried. After concentration, a light yellow oil remains, from which 3.5 g of colorless crystals of mp 69 ° to 71 ° C. are obtained when rubbed with diisopropyl ether.
  • 82 g of tert-butyl - [(2-methylphenyl) chloromethyl] sulfide are added dropwise to the solution of 43.6 g of imidazole in 300 ml of acetone with stirring. After adding 88 g of finely powdered potassium carbonate, the mixture is heated under reflux for 5 hours. The undissolved constituents are then filtered off and the filtrate is concentrated. The residue mixed with 300 ml of water is extracted with 3 x 200 ml of methylene chloride. After washing with water, drying and concentrating, 69 g of a brownish oil remain from the combined organic phases, which are dissolved in 1 l of diisopropyl ether.
  • the colorless, insoluble residue of the hexane extractions consists of 27 g (12%) 2,4-dichlorobenzyl - [(2 ', 4'-dichlorophenyl) - (1,2,4-triazol-4-yl) methyl] sulfide from mp. 132-133 ° C.
  • a solution of 7.1 g of 85 percent 3-chloroperbenzoic acid in 70 is added dropwise to the solution of 9.7 g of tert-butyl - [(4-chlorophenyl) -1,2,4-triazolylmethyl] sulfide in 20 ml of methylene chloride while cooling with ice ml of methylene chloride.
  • the new a-azolyl sulfides, a-azolyl sulfoxides and a-azolyl sulfones and their salts show a considerably broader fungicidal activity and a superior plant tolerance than the known 1- [2,4-dichlorophenyl-ß-allylethyl ether] imidazole.
  • the new active ingredients can also be in the form of their salts, e.g. B. hydrochlorides, oxalates or nitrates can be used.
  • crop plants mean wheat, rye, barley, oats, rice, corn, apple tree, cucumber, beans, coffee, sugar cane, grapevine, strawberries and ornamental plants in horticulture.
  • the active compounds according to the invention are systemically active.
  • the systemic effectiveness of these agents is of particular interest in connection with the control of internal plant diseases, for. B. grain rust, powdery mildew.
  • the agents according to the invention can simultaneously suppress the growth of two or more of the fungi mentioned and are highly tolerated by plants.
  • the application rates required to control the phytopathogenic fungi are between 0.05 and 2 kg of active ingredient / ha of cultivated area.
  • the active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are manufactured in a known manner, e.g. B. by mixing the active ingredient with solvents and / or carriers, optionally using emulsifiers and dispersants, and in the case of using water as a diluent also other organic solvents as auxiliary solvents! can be used.
  • solvents such as aromatics (e.g. xylene, benzene), chlorinated armates (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g.
  • ⁇ ⁇
  • Carriers such as natural rock powder (e.g. kaolins, clays, talc, chalk) and synthetic rock powder (e.g. highly disperse silica, silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin, sulfite liquor and methyl cellulose.
  • Carriers such as natural rock powder (e.g. kaolins, clays, talc, chalk) and synthetic rock powder (e.g. highly disperse silica, silicates)
  • Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ether, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin, sulfite liquor and methyl
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the formulations or the ready-to-use preparations produced therefrom, such as solutions, emulsions, suspensions, powders, pastes or granules, are used in a known manner, for example by spraying, atomizing, dusting, scattering, pickling or pouring.
  • agents according to the invention can also be present in these use forms together with other active ingredients, e.g. B. herbicides, insecticides, growth regulators and fungicides or with fertilizers.
  • active ingredients e.g. B. herbicides, insecticides, growth regulators and fungicides or with fertilizers.
  • Leaves of »Firlbeck's Union « barley seedlings grown in pots are sprayed with aqueous emulsions of 80% (% by weight) active ingredient and 20% emulsifier and after the Drying the spray coating with oidia (spores) of the barley powdery mildew (Erysiphe graminis var. Hordei) dusted.
  • the test plants are then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80% relative humidity. After 10 days, the extent of the development of mildew is determined.
  • Leaves of »Jubilar « wheat seedlings grown in pots are artificially infected with spores of the wheat brown rust (Puccinia recondita) 24 hours before spraying and placed at 20 to 25 ° C in a water vapor-saturated chamber.
  • the plants are then sprayed with aqueous emulsions of 80% (weight percent) active ingredient and 20% emulsifier. After the spray coating has dried on, the test plants are placed in the greenhouse at temperatures between 20 and 22 ° C. and 75 to 80% relative atmospheric humidity. After 10 days, the extent of the rust fungus development is determined.
  • active ingredient 2 20 parts by weight of active ingredient 2 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene- ⁇ -sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill.
  • a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
  • active ingredient 1 40 parts by weight of active ingredient 1 are intimately mixed with 10 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 parts of water. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion which contains 0.04% by weight of active ingredient.
  • active ingredient 2 20 parts are intimately mixed with 2 parts of calcium salt of dodecylbenzenesulfonic acid, 8 parts of fatty alcohol polyglycol ether, 2 parts of sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil. A stable oily dispersion is obtained.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP78100538A 1977-08-05 1978-07-28 Alpha-azolysulfide, -sulfoxide und -sulfone, deren Salze und Metallkomplexe, Verfahren zu ihrer Herstellung, sowie sie enthaltende Mittel zur Pilzbekämpfung Expired EP0000752B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2735314 1977-08-05
DE19772735314 DE2735314A1 (de) 1977-08-05 1977-08-05 Alpha-azolylsulfide und deren derivate

Publications (3)

Publication Number Publication Date
EP0000752A2 EP0000752A2 (de) 1979-02-21
EP0000752A3 EP0000752A3 (en) 1979-04-04
EP0000752B1 true EP0000752B1 (de) 1981-01-14

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ID=6015701

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100538A Expired EP0000752B1 (de) 1977-08-05 1978-07-28 Alpha-azolysulfide, -sulfoxide und -sulfone, deren Salze und Metallkomplexe, Verfahren zu ihrer Herstellung, sowie sie enthaltende Mittel zur Pilzbekämpfung

Country Status (14)

Country Link
EP (1) EP0000752B1 (fi)
JP (1) JPS5430174A (fi)
AT (1) AT360279B (fi)
CA (1) CA1112647A (fi)
CS (1) CS200238B2 (fi)
DD (1) DD137525A5 (fi)
DE (2) DE2735314A1 (fi)
DK (1) DK145597C (fi)
FI (1) FI64360C (fi)
HU (1) HU180205B (fi)
IL (1) IL55241A (fi)
IT (1) IT1107959B (fi)
PL (1) PL107615B1 (fi)
SU (1) SU795436A3 (fi)

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005754A1 (de) * 1978-05-19 1979-12-12 BASF Aktiengesellschaft Mittel und Verfahren zur Regulierung des Pflanzenwachstums
EP0056860A1 (de) * 1981-01-08 1982-08-04 BASF Aktiengesellschaft Substituierte Azolyl-glykolsulfonate, diese enthaltende Fungizide und Verfahren zu ihrer Herstellung
EP0091219A2 (en) * 1982-04-01 1983-10-12 Schering Agrochemicals Limited Heterocyclic fungicidal and growth regulant compounds, and compositions containing them
EP0098243A1 (de) * 1982-06-25 1984-01-11 Ciba-Geigy Ag Neue Säure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Mikroorganismen
EP0107392A1 (en) * 1982-10-09 1984-05-02 Pfizer Limited Triazole antifungal agents
EP0140571A1 (en) * 1983-09-30 1985-05-08 Schering Agrochemicals Limited Diazole and triazole compounds
US4636514A (en) * 1982-08-13 1987-01-13 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes
US4701463A (en) * 1982-08-13 1987-10-20 The Dow Chemical Company Pyridyl (pyridyloxy or pyriolylthio) azolomethanes
US4701207A (en) * 1982-08-13 1987-10-20 The Dow Chemical Company Phenyl (phenoxy or phenylthio) azolomethanes
US4716174A (en) * 1982-08-13 1987-12-29 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4717734A (en) * 1982-08-13 1988-01-05 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4717732A (en) * 1982-08-13 1988-01-05 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4717733A (en) * 1982-08-13 1988-01-05 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4720502A (en) * 1982-08-13 1988-01-19 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4728657A (en) * 1982-08-13 1988-03-01 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes
US4731372A (en) * 1982-08-13 1988-03-15 The Dow Chemical Company Aryl(aryloxy or arylthio) azolomethanes, and their use as pesticides
US4767752A (en) * 1985-03-18 1988-08-30 S.D.S. Biotech K.K. Imidazolyl or triazolyl substituted propionate derivative and nonmedical fungicide containing the same
FR2677983A1 (fr) * 1991-06-24 1992-12-24 Oreal Composes alkylthiopoly(ethylimidazolium), procede de preparation et leur utilisation comme agents biocides.
CN100562516C (zh) * 2001-12-27 2009-11-25 第一制药株式会社 β-淀粉样蛋白产生和分泌的抑制剂

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0061835B1 (en) * 1981-03-18 1989-02-01 Imperial Chemical Industries Plc Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
DK348883A (da) * 1982-08-13 1984-02-14 Dow Chemical Co Aryl(aryloxy eller arylthio)azolomethaner, deres fremstilling og anvendelse
US4937250A (en) * 1988-03-07 1990-06-26 Ciba-Geigy Corporation Alpha-heterocycle substituted tolunitriles
US4978672A (en) * 1986-03-07 1990-12-18 Ciba-Geigy Corporation Alpha-heterocyclc substituted tolunitriles
US4749713A (en) * 1986-03-07 1988-06-07 Ciba-Geigy Corporation Alpha-heterocycle substituted tolunitriles
GB0108592D0 (en) * 2001-04-05 2001-05-23 Merck Sharp & Dohme Therapeutic agents
AU2004251987C1 (en) 2003-06-30 2010-11-18 Daiichi Sankyo Company, Limited Heterocyclic methyl sulfone derivative
US7314875B2 (en) * 2004-04-13 2008-01-01 Cephalon, Inc. Tricyclic aromatic and bis-phenyl sulfinyl derivatives

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0005754A1 (de) * 1978-05-19 1979-12-12 BASF Aktiengesellschaft Mittel und Verfahren zur Regulierung des Pflanzenwachstums
EP0056860A1 (de) * 1981-01-08 1982-08-04 BASF Aktiengesellschaft Substituierte Azolyl-glykolsulfonate, diese enthaltende Fungizide und Verfahren zu ihrer Herstellung
EP0091219A3 (en) * 1982-04-01 1984-06-27 Fbc Limited Heterocyclic fungicidal and growth regulant compounds, and compositions containing them
EP0091219A2 (en) * 1982-04-01 1983-10-12 Schering Agrochemicals Limited Heterocyclic fungicidal and growth regulant compounds, and compositions containing them
EP0098243A1 (de) * 1982-06-25 1984-01-11 Ciba-Geigy Ag Neue Säure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung von Mikroorganismen
US4716174A (en) * 1982-08-13 1987-12-29 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4717732A (en) * 1982-08-13 1988-01-05 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4636514A (en) * 1982-08-13 1987-01-13 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes
US4701463A (en) * 1982-08-13 1987-10-20 The Dow Chemical Company Pyridyl (pyridyloxy or pyriolylthio) azolomethanes
US4701207A (en) * 1982-08-13 1987-10-20 The Dow Chemical Company Phenyl (phenoxy or phenylthio) azolomethanes
US4731372A (en) * 1982-08-13 1988-03-15 The Dow Chemical Company Aryl(aryloxy or arylthio) azolomethanes, and their use as pesticides
US4717734A (en) * 1982-08-13 1988-01-05 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4728657A (en) * 1982-08-13 1988-03-01 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes
US4717733A (en) * 1982-08-13 1988-01-05 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
US4720502A (en) * 1982-08-13 1988-01-19 The Dow Chemical Company Aryl(aryloxy or arylthio)azolomethanes and their use as pesticides
EP0107392A1 (en) * 1982-10-09 1984-05-02 Pfizer Limited Triazole antifungal agents
EP0140571A1 (en) * 1983-09-30 1985-05-08 Schering Agrochemicals Limited Diazole and triazole compounds
US4767752A (en) * 1985-03-18 1988-08-30 S.D.S. Biotech K.K. Imidazolyl or triazolyl substituted propionate derivative and nonmedical fungicide containing the same
FR2677983A1 (fr) * 1991-06-24 1992-12-24 Oreal Composes alkylthiopoly(ethylimidazolium), procede de preparation et leur utilisation comme agents biocides.
EP0520873A1 (fr) * 1991-06-24 1992-12-30 L'oreal Composés alkylthiopoly(éthylimidazolium), procédé de préparation et leur utilisation comme agents biocides
CN100562516C (zh) * 2001-12-27 2009-11-25 第一制药株式会社 β-淀粉样蛋白产生和分泌的抑制剂

Also Published As

Publication number Publication date
JPS5430174A (en) 1979-03-06
EP0000752A3 (en) 1979-04-04
IL55241A (en) 1982-01-31
DK145597C (da) 1983-08-15
IT7850557A0 (it) 1978-08-01
PL107615B1 (pl) 1980-02-29
FI64360B (fi) 1983-07-29
DK145597B (da) 1982-12-20
IT1107959B (it) 1985-12-02
HU180205B (en) 1983-02-28
IL55241A0 (en) 1978-09-29
EP0000752A2 (de) 1979-02-21
PL208828A1 (pl) 1979-05-21
AT360279B (de) 1980-12-29
SU795436A3 (ru) 1981-01-07
DK345678A (da) 1979-02-06
CS200238B2 (en) 1980-08-29
DD137525A5 (de) 1979-09-12
FI782403A (fi) 1979-02-06
CA1112647A (en) 1981-11-17
FI64360C (fi) 1983-11-10
DE2860325D1 (en) 1981-03-12
ATA568678A (de) 1980-05-15
DE2735314A1 (de) 1979-02-22

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