WO1994004517A1 - Iodure de 1,2,4-dithiazolium et son utilisation comme parasiticide - Google Patents

Iodure de 1,2,4-dithiazolium et son utilisation comme parasiticide Download PDF

Info

Publication number
WO1994004517A1
WO1994004517A1 PCT/EP1993/002114 EP9302114W WO9404517A1 WO 1994004517 A1 WO1994004517 A1 WO 1994004517A1 EP 9302114 W EP9302114 W EP 9302114W WO 9404517 A1 WO9404517 A1 WO 9404517A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
chain
formula
carbon atoms
dithiazolium
Prior art date
Application number
PCT/EP1993/002114
Other languages
German (de)
English (en)
Inventor
Ulrich Heinemann
Heinz-Wilhelm Dehne
Christoph Erdelen
Ulrike Wachendorff-Neumann
Original Assignee
Bayer Aktiengesellschaft
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer Aktiengesellschaft filed Critical Bayer Aktiengesellschaft
Priority to KR1019950700591A priority Critical patent/KR950702973A/ko
Priority to JP6505847A priority patent/JPH08500581A/ja
Priority to EP94908167A priority patent/EP0655999A1/fr
Priority to AU49470/93A priority patent/AU4947093A/en
Priority to BR9306924A priority patent/BR9306924A/pt
Publication of WO1994004517A1 publication Critical patent/WO1994004517A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Definitions

  • the invention relates to new 1,2,4-dithiazolium iodides, a process for their preparation, their use in pesticides and new starting compounds.
  • R 1 represents alkyl or aryl
  • R 2 stands for Alkvl or R- and R- together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle which may optionally contain further heteroatoms,
  • the compounds of the formula (I) can optionally be present as geometric and / or optical isomers or isomer mixtures of different compositions. Both the pure isomers and the isomer mixtures are claimed according to the invention.
  • R stands for alkyl or aryl
  • R 2 represents alkyl
  • R and R 2 together with the nitrogen atom to which they are attached represent an optionally substituted heterocycle which may optionally contain further heteroatoms,
  • R represents alkyl
  • Rl and R 2 have the meaning given above
  • the 1,2,4-dithiazolium iodides of the general formula (I) according to the invention have a considerably better pesticidal activity compared to the dithiazolethiones known from the prior art, such as, for example, the compound 3-dimethylamino-1, 2,4-dithiazol-5-thione, which are chemically and functionally obvious compounds.
  • Formula (I) provides a general definition of the 1,2,4-dithiazolium iodides according to the invention. Compounds of formula (I) are preferred in which
  • R stands for straight-chain or branched alkyl with 1 to 8 carbon atoms or for aryl with 6 to 10 carbon atoms which is optionally mono- or polysubstituted, identically or differently, the following being suitable as substituents:
  • R 2 represents straight-chain or branched alkyl having 1 to 8 carbon atoms or
  • Rl and R 2 together with the nitrogen atom to which they are attached represent an optionally mono- or polysubstituted, identically or differently substituted, saturated five- to seven-membered heterocycle, which may contain further heteroatoms - in particular nitrogen, oxygen or sulfur - may contain, where the following are suitable as substituents: halogen, in each case straight-chain or branched alkyl or alkoxy each having 1 to 4 carbon atoms, each straight-chain or branched haloalkyl or haloalkoxy each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms.
  • Rl represents straight-chain or branched alkyl having 1 to 6 carbon atoms or phenyl which is monosubstituted to trisubstituted by identical or different substituents, the following being suitable in each case: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy,
  • R and R 2 together with the nitrogen atom to which they are attached represent an optionally mono- to tetrasubstituted, identically or differently substituted, saturated five- to seven-membered heterocycle which may optionally contain a further heteroatom - in particular nitrogen, oxygen or sulfur , where the following are suitable as substituents: halogen or in each case straight-chain or branched alkyl or alkoxy each having 1 to 4 carbon atoms.
  • R stands for straight-chain or branched alkyl having 1 to 4 carbon atoms or for phenyl which is monosubstituted or disubstituted, identically or differently, where the following are suitable as substituents: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, trifluoromethyl, difluoromethyl, trifluoromethoxy or difluoromethoxy and
  • R 2 represents straight-chain or branched alkyl having 1 to 4 carbon atoms or
  • R and R 2 together with the nitrogen atom to which they are attached represent an optionally mono- or disubstituted pyrrolidinyl, piperidinyl, perhydroazepinyl or morpholinyl radical, the substituents in each case being: chlorine, methyl, ethyl, methoxy or ethoxy.
  • N- [5-methylthio-3H-1,2,4-dithiazol-3-ylidene] -N-methyl-methaniminium iodide and 2,6-dimethylmorpholine are used as starting materials, represent the course of the reaction of the process according to the invention using the following formula:
  • Formula (II) provides a general definition of the 3-alkylthio-1,2,4-dithiazolium iodides required as starting materials for carrying out the process according to the invention.
  • R preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.
  • a dipolar, aprotic diluent such as acetonitrile at temperatures between 20 C and 120 C.
  • Alkyl iodides of the formula (V) are generally known compounds of organic chemistry.
  • Inert organic solvents are suitable as diluents for carrying out the process according to the invention.
  • These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 C and 140 C, preferably at temperatures between 20 C and 80 C.
  • the process according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
  • the end products of the formula (I) are also purified using customary methods, for example by column chromatography or by recrystallization.
  • the characterization is carried out using the melting point or, in the case of non-crystallizing compounds, using proton nuclear magnetic resonance spectroscopy (H-NMR).
  • the active substances are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda for example Oniscus asellus, Armadillidium vulgare, Porcellio scaber; from the order of the Diplopoda, for example, Blaniulus guttulatus; from the order of the Chilopoda, for example Geophilus carpophagus, Scutigera spec; from the order of the Symphyla, for example Scutigerella immaculata; from the order of the Thysanura, for example Lepisma saccharina; from the order of the Collembola, for example Onychiurus armatus; from the order of the Orthoptera, for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria; from the order of the Dermaptera, for example for
  • Rhopalosiphum padi Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp., Psylla from the order of the Lepidoptera, for example Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Agriotellisella, Bucculisella.
  • Feltia spp. Earias insula- na, Heliothis spp., Laphygma exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyraustaestia kubiau, Eraas mellonella, Tineola bisselliella, Tinea pelhonella, Hofinannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana; from the order of the Coleoptera, for example Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hy
  • Hymenoptera From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp .; from the order of the Diptera, for example Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis
  • Ceratophyllus spp . from the order of the Arachnida, for example Scorpio maurus, Latrodectus mactans; from the order of the Acarina, for example Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp.
  • Psoroptes spp. Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tet ⁇ ranychus spp ..
  • the active compounds according to the invention are notable for high insecticidal and acaricidal activity. They can be used with particularly good success for combating plant-damaging insects, for example against the larvae of the green rice leafhopper (Nephotettix cincticeps) or against the larvae of the horseradish beetle (Phaedon cochleariae) or against the green peach aphid (Myzus persicae) or against the tobacco bud caterpillar (Heliothis virescens) or against the caterpillars of the cockroach (Plutella maculipennis) or against the common spider mite (Tetranychus urticae).
  • insect-damaging insects for example against the larvae of the green rice leafhopper (Nephotettix cincticeps) or against the larvae of the horseradish beetle (Phaedon cochleariae) or against the green peach aphid (Myzus persicae) or
  • the active compounds according to the invention have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
  • the active ingredients are therefore also suitable for use as fungicides.
  • Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Plasmopara species, such as, for example, Plasmopara viticola; Peronospora species, such as, for example, Peronospora pisi or Peronospora brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca Sportsiginea;
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or Pyrenophora graminea
  • Drechslera (Conidial form: Drechslera, synonym: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus (conidial form: Drechs ⁇ lera, synonym: Helminthosporium); Uromyces species, such as, for example, Uromyces appendiculatus;
  • Puccinia species such as, for example, Puccinia recondita
  • 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 herpotrichoides.
  • the active compounds according to the invention can be particularly successful in combating diseases in fruit and vegetable cultivation, such as, for example, against the pathogen causing tomato brown rot (Phytophthora infestans) or against the pathogen causing apple scab (Venturia inaequalis) or against the pathogen causing mildew on vines (Uncinula necator) or for combating rice diseases, such as, for example, against the pathogen causing the rice stain disease (Pyricularia oryzae).
  • diseases in fruit and vegetable cultivation such as, for example, against the pathogen causing tomato brown rot (Phytophthora infestans) or against the pathogen causing apple scab (Venturia inaequalis) or against the pathogen causing mildew on vines (Uncinula necator)
  • rice diseases such as, for example, against the pathogen causing the rice stain disease (Pyricularia oryzae).
  • the active substances can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations in po - Lymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., and ULV cold and warm mist formulations.
  • the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, very fine encapsulations in po - Lymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., and ULV cold and warm mist formulations.
  • formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, ie liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
  • extenders ie liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can, for example, also be used as auxiliary solvents.
  • flavors such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, 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;
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide;
  • Solid carrier materials are suitable: for example natural rock powder, such as kaolins
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and tin are used.
  • 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 tin are 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 be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide limits when used as insecticides.
  • the active ingredient concentration of the use forms can be from 0.0000001 to 95 Weight percent active ingredient, preferably between 0.0001 and 1 weight percent.
  • the application takes place in a customary manner adapted to the application forms.
  • the active compounds according to the invention can likewise be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and also in mixtures with fertilizers and growth regulators.
  • the active compounds When used as fungicides, the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, atomizing, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients by the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself. The seeds of the plants can also be treated.
  • the active compound concentrations when used as fungicides in the use forms can be varied within a substantial range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight. %.
  • seed treatment when used as fungicides, amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
  • active substance concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
  • 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 and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Soybean shoots (Glycine max) are treated by dipping into the active ingredient preparation of the desired concentration and populated with the tobacco bud caterpillar (Heliothis virescens) while the leaves are still moist.
  • the kill is determined in percent. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • 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 and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish beetle larvae (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in percent. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
  • 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 and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cabbage cockroach (Plutella maculipennis) while the leaves are still moist.
  • the kill is determined in percent. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • 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 and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentrations.
  • Bean plants Phaseolus vulgaris which are heavily infested with all stages of development of the common spider mite (Tetranychus urticae) are immersed in a preparation of active compound of the desired concentration.
  • the kill is determined in percent. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • 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 and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Cabbage leaves (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill is determined in percent. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Active ingredients Active ingredient concentration in% in concentration after 6 days
  • 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 and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with larvae of the green rice leafhopper (Nephotettix cicticeps) while the seedlings are still moist.
  • the kill is determined in percent. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
  • Active ingredients Active ingredient concentration in% in concentration after 6 days
  • Active ingredients Active ingredient concentration in% in concentration after 6 days
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
  • a 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 an incubation cabin at 20 ° C. and a relative humidity of approx. 100%.
  • Evaluation is carried out 3 days after the inoculation.
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
  • a 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 23 ° C to 24 ° C and a relative humidity of approx. 75%.
  • Evaluation is carried out 14 days after the inoculation.
  • the control should be carried out at an active ingredient concentration of 10 ppm
  • Emulsifier 0.3 part by weight of alkyl aryl polyglycol ether
  • a 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 atmospheric humidity of approx. 70%.
  • Evaluation is carried out 12 days after the inoculation.
  • the compound according to preparation example 2 at an active substance concentration of 5 ppm shows a clear superiority in effectiveness compared to the prior art.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (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)

Abstract

Nouvel iodure de 1,2,4-dithiazolium de formule (I) dans laquelle R1 et R2 ont les significations données dans la description. L'invention concerne en outre un procédé de fabrication de ce produit et son utilisation comme parasiticide et comme nouveau composé de départ. Les nouveaux composés de formule (I) peuvent être fabriqués selon des procédés connus, par exemple à partir d'iodures de 3-alkylthio-1,2,4-dithiazolium appropriés avec des amines appropriées. Les iodures de 3-alkylthio-1,2,4-dithiazolium utilisés sont également nouveaux et peuvent être préparés à partir de 3-diméthylamino-1,2,4-dithiazoline-5-thione et d'iodures d'alkyle.
PCT/EP1993/002114 1992-08-21 1993-08-09 Iodure de 1,2,4-dithiazolium et son utilisation comme parasiticide WO1994004517A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1019950700591A KR950702973A (ko) 1992-08-21 1993-08-09 1,2,4-디티아졸륨 요오다이드 및 농약으로서의 그의 용도(1,2,4-Dithiazolium iodides and their use as pesticides)
JP6505847A JPH08500581A (ja) 1992-08-21 1993-08-09 １，２，４−ジチアゾリウムヨーダイド及びその有害生物防除剤としての利用
EP94908167A EP0655999A1 (fr) 1992-08-21 1993-08-09 Iodure de 1,2,4-dithiazolium et son utilisation comme parasiticide
AU49470/93A AU4947093A (en) 1992-08-21 1993-08-09 1,2,4-dithiazolium iodides and their use as pesticides
BR9306924A BR9306924A (pt) 1992-08-21 1993-08-09 Derivados de 1,3-oxazolidina pirdil-substituídos oidetos de 1,2,4-ditioz lio de novos compostos de partida

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEP4227751.5 1992-08-21
DE4227751A DE4227751A1 (de) 1992-08-21 1992-08-21 1,2,4-Dithiazolium-iodide und neue Ausgangsverbindungen

Publications (1)

Publication Number Publication Date
WO1994004517A1 true WO1994004517A1 (fr) 1994-03-03

Family

ID=6466089

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/002114 WO1994004517A1 (fr) 1992-08-21 1993-08-09 Iodure de 1,2,4-dithiazolium et son utilisation comme parasiticide

Country Status (9)

Country Link
EP (1) EP0655999A1 (fr)
JP (1) JPH08500581A (fr)
KR (1) KR950702973A (fr)
AU (1) AU4947093A (fr)
BR (1) BR9306924A (fr)
DE (1) DE4227751A1 (fr)
HU (1) HUT71980A (fr)
RU (1) RU95109103A (fr)
WO (1) WO1994004517A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0629401A1 (fr) * 1993-06-18 1994-12-21 Bayer Ag Utilisation de sels de 1,2,4-dithiazolium comme agents chimiothérapeutiques, en particulier comme inhibiteurs de TNF, et nouveaux sels de dithiazolium
WO2023147571A3 (fr) * 2022-01-31 2023-09-14 University Of Mississippi Agents sélectifs ciblant mycobacterium tuberculosis

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE202015102174U1 (de) 2015-04-30 2016-08-03 Gebr. Schmidt Fabrik für Feinmechanik GmbH & Co. KG Nachfüllsystem für einen ein Fluid aufnehmenden Behälter

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3944670A (en) * 1972-11-08 1976-03-16 E. I. Du Pont De Nemours And Company Pesticidal dithiazolium salts

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3944670A (en) * 1972-11-08 1976-03-16 E. I. Du Pont De Nemours And Company Pesticidal dithiazolium salts

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 93, no. 15, 13 October 1980, Columbus, Ohio, US; abstract no. 144738q, page 242; *
J.E. OLIVER ET AL.: "Imino-1,2,4-dithiazoles. I. Alkylation", JOURNAL OF ORGANIC CHEMISTRY, vol. 39, no. 15, 26 July 1974 (1974-07-26), WASHINGTON US, pages 2225 - 2228 *
J.E. OLIVER ET AL.: "Insect Chemosterilants. 1,2,4-Dithiazolium Salts and Related Compounds as Additives to Housefly Diet", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 21, no. 5, 1973, WASHINGTON US, pages 753 - 755 *
J.E. OLIVER ET AL.: "Insect Chemosterilants. 11. Substituted 3,5-Diamino-1,2,4-dithiazolium Salts and Related Compounds", JOURNAL OF MEDICINAL CHEMISTRY, vol. 15, no. 3, 1972, WASHINGTON US, pages 315 - 320 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0629401A1 (fr) * 1993-06-18 1994-12-21 Bayer Ag Utilisation de sels de 1,2,4-dithiazolium comme agents chimiothérapeutiques, en particulier comme inhibiteurs de TNF, et nouveaux sels de dithiazolium
US5502066A (en) * 1993-06-18 1996-03-26 Bayer Aktiengesellschaft 1,2,4-dithiazolium salts as chemotherapeutics
WO2023147571A3 (fr) * 2022-01-31 2023-09-14 University Of Mississippi Agents sélectifs ciblant mycobacterium tuberculosis

Also Published As

Publication number Publication date
DE4227751A1 (de) 1994-02-24
KR950702973A (ko) 1995-08-23
EP0655999A1 (fr) 1995-06-07
BR9306924A (pt) 1999-01-12
RU95109103A (ru) 1996-12-20
AU4947093A (en) 1994-03-15
HU9500523D0 (en) 1995-04-28
HUT71980A (en) 1996-03-28
JPH08500581A (ja) 1996-01-23

Similar Documents

Publication Publication Date Title
EP0300218A1 (fr) Utilization de 1,4-naphthochinones substituées comme acaricide et fongicide
EP0416365B1 (fr) Dérivés d'anilide carbocyclique
US5510364A (en) 2-cyanobenzimidazoles and their use, and new precursors
EP0591806A1 (fr) 2-arylpyrroles substitués
DE3605002A1 (de) Phosphorsaeureester
DE4327596A1 (de) 3-Methoxy-2-phenyl-acrylsäuremethylester
EP0546387B1 (fr) Oximetheramides substitués
EP0189043B1 (fr) Furazans substitués
WO1994004517A1 (fr) Iodure de 1,2,4-dithiazolium et son utilisation comme parasiticide
EP0069881A1 (fr) Esters s-azolyl-methyl-d'acides di(tri) thiophosphoriques, leur procédé de préparation et leur utilisation comme pesticides
EP0361185B1 (fr) Dérivés de pyrimidines substitués en position 2 par un radical halogénomethylthio.
DE2815290A1 (de) Neue diarylamine, verfahren zu ihrer herstellung und ihre verwendung
DE4303658A1 (de) Substituierte Tetrahydropyridazincarboxamide
EP0579908B1 (fr) Dérivés de pyridyle, procédé pour leur préparation et leur utilisation comme pesticide
EP0572440B1 (fr) Pyridylpyrimidines substituees, leur preparation et leur utilisation, ainsi que nouveaux intermediaires
EP0316734B1 (fr) Furazannyl urées
EP0258631A2 (fr) Alkoxyiminoalkylamides
EP0532918A1 (fr) Pyrazolines substitués comme pesticides
EP0658562A1 (fr) Dérivés d'acide phosphorique pesticides
EP0410172A2 (fr) Dérivés de 2-halogéno-3-phénoxy-1,4-naphtoquinone
EP0507142A2 (fr) Esteramides d'acides O-halocyclobutyl-S-alkyl-(di) thiophosphorique, procédé pour les préparer et leur utilisation comme pesticides
WO1995015968A1 (fr) Derives d'acide phosphonique utilises comme pesticides
EP0167019A1 (fr) Dérivés diaryl-éthylaminés
EP0201032A2 (fr) N-halogéno-alcoylsulfényl(thio) carbamates
EP0185257A1 (fr) Esters d'acide oxamique carbamylé contenant de l'azole, procédé pour leur préparation et leur utilisation comme produits de protection pour plantes

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BR BY CA CZ HU JP KR KZ NZ RU SK UA US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 1994908167

Country of ref document: EP

ENP Entry into the national phase

Ref country code: US

Ref document number: 1995 387754

Date of ref document: 19950215

Kind code of ref document: A

Format of ref document f/p: F

WWP Wipo information: published in national office

Ref document number: 1994908167

Country of ref document: EP

NENP Non-entry into the national phase

Ref country code: CA

WWW Wipo information: withdrawn in national office

Ref document number: 1994908167

Country of ref document: EP