Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom

Definitions

• the present invention relates to thiophenes and polythiophenes of the formula I
• R 1 , R 2 and R 3 independently of one another are hydrogen and Ci-Ci ⁇ -alkylthio
• R 1 , R 2 and R 3 are not simultaneously hydrogen and where R 1 is not hydrogen if R 2 is methylthio and n is 0.
• the invention relates to processes for the preparation of these compounds, compositions comprising at least one thiophene or polythiophene of the formula I '
• R 1 , R 2 and R 3 independently of one another Hydrogen and Ci-Ci ⁇ -alkylthio
• the invention was based on new active substances suitable for pest control as a task.
• the introduction of the halogen substituent is generally carried out according to the method described by Taylor et al. described method (p. 1003) in the presence of N-bromosuccinimide or N-chlorosuccinimide.
• the reaction temperatures are usually 0 ° C to 50 ° C, preferably 10 ° C to 40 ° C.
• the halogenating agents can generally be used in equimolar amounts or in excess.
• Halogenated hydrocarbons such as methylene chloride and tetrachloroethane and protically polar solvents such as acetic acid are particularly suitable as solvents.
• the preparation and implementation of the Grignard compound is advantageously carried out in accordance with the method described by MacEachern et al. described method carried out.
• the reaction temperatures are usually 10 ° C to 60 ° C, preferably 20 ° C to 50 ° C.
• the amount of magnesium shavings or Magnesiu gries' is generally at least equimolar, but is usually used in an excess.
• Suitable solvents are in particular ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether and dioxane, particularly preferably diethyl ether and tert-butyl methyl ether.
• a halogenated thiophene is reacted with a disulfide in general at low temperatures in an aprotic solvent in the presence of an alkali metal organyl.
• the reaction temperatures are usually from -100 ° C to 0 ° C, preferably from -80 ° C to -40 ° C.
• the alkali metal organyls used are generally organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyllithium and phenyllithium. into consideration.
• the alkali metal organyls are generally used in an excess of 10 to 100 mol%, preferably 10 to 50 mol%, based on the halothiophene.
• Aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane and tetrahydrofu are used as solvents, particularly preferably ethers.
• the starting materials are generally reacted with one another at least in an equimolar amount. With a view to increasing the yield, however, it may be advantageous to use an excess of 10 mol% to 100 mol%, preferably 10 mol% to 50 mol%, in particular 10 mol%, of the disulfide. % to 20 mol% based on the amount of halogen thiophene.
• Ci-Cis-alkylthio especially Ci-Ce-alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio , 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1, 1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4- Methylpentylthio, 1, 1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,
• radicals R 3 it being possible for the radicals R 3 to be different if the value of n is> 1.
• radicals R 3 it being possible for the radicals R 3 to be different if the value of n is> 1.
• thiophenes and polythiophenes of the formula I ' are particularly preferred in which the substituents and the index have the following meaning:
• R 1 , R- and R 3 independently of one another
• radicals R 3 it being possible for the radicals R 3 to be different if the value of n is> 1.
• R 1 , R 2 and R 3 independently of one another are hydrogen and methyl thio
• the compounds of the formula I ' are suitable for effectively controlling pests from the class of the insects, arachnids and nematodes. They can be used as pesticides in crop protection and in the hygiene, supply protection and veterinary sectors.
• the harmful insects include from the order of the
• Butterflies for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneuraoneumoneidomoneirone, fumiferella, choristoneura fumiferellaidia unidirectional fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumiferella, choristoneura fumifeella, choristoneura fumiferida Diaphania nitidalis, Diatrae
• Pectinophora gossypiella Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scarbra, Plutella xylostella, Pseudoplusia includesoptera, Spyacoda lodipod, frotana, Scrobipalpulaotha, Diana , Tortrix viridana, Trichoplusia ni, Zeiraphera canadensis.
• Diaptera From the order of the two-winged species (Diptera), for example, Aedes aegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chryso ya hominivorax, Chrysomya macellaria, Contarinia sorghicola, Dylobaculexucaceacita, acylucia pacita, acylucia pacificaceae, Cylobaceapura brassicae, Fannia canicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Mushroom Domica, Lyi
• Thrips for example Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi, Thrips tabaci.
• From the order of the hymenoptera for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta.
• Heteroptera From the order of the bugs (Heteroptera), for example, Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratidularis, Parsma viralisea, Pira .
• bugs Heteroptera
• Acrosternum hilare Blissus leucopterus
• Cyrtopeltis notatus Dysdercus cingulatus
• Dysdercus intermedius Eurygaster integriceps
• Euchistus impictiventris Leptoglossus phyllopus
• Lygus lineolaris Lygus pratidularis
• Parsma viralisea Pira
• suckers for example, Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci,
• Brachycaudus cardui Brevicoryne brassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dyasphis radicola, Dysaulacorthum pseudosolani, E poasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Megodipononium, Macodipononiumia, Macrosiphoniumia, Macodipa bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphu maidis, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Trialeurodes vitarifoli, Vite.
• Orthoptera for example Acheta domestica, Blatta orientalis, Blattella germanica, Forficula auricularia,
• arachnids such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoenicis, Bryobia praetiosa, Dermacentor silvarum, shedelodi, iodine eroniophus, Iotetroniiuncus, Iotetranyius, Iotetronii Ixodes rubicundus, Ornithodorus moubata, Otobins megnini, Paratetranychus pilosus, Permanyssus gallinae, Phyllocaptrata oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Saccop
• Tetranychus kanzawai Tetranychus pacificus, Tetranychus telarius, Tetranychus urticae.
• root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycinae, Heterodera schatii, Hetrodera triflolii, stalks and leaves, e.g. Belonolaimus longicaudatus, Ditylenchus destructor, Ditylenchus dipsaci,
• root gall nematodes e.g. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, e.g. Globodera rostochiensis, Heterodera avenae, Heterodera glycinae, Heterodera schatii, Hetroder
• the active compounds can be sprayed as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oldispersions, pastes, dusts, scattering agents, granules hen, nebulizing, dusting, scattering or pouring can be used.
• the application forms depend entirely on the Uses; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
• mineral oil fractions of medium to high boiling point such as kerosene or diesel oil
• coal tar oils as well as oils of vegetable or animal origin
• aliphatic, cyclic and aromatic hydrocarbons e.g. Benzene, toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol.
• Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, old dispersions) by adding water.
• emulsions, pastes or old dispersions the substances as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
• concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
• Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
• III.10 parts by weight of compound no. 4 are dissolved in a mixture consisting of 90 parts by weight of xylene, 6 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid -N-monoethanolamide, 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 2 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil.
• Granules e.g. Coating, impregnation and homogeneous granules can be produced by binding the active ingredients to solid carriers.
• Solid carriers are e.g. Mineral soils, such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products, such as grain meal, tree bark, wood and nutshell meal, cellulose powder and other solid carrier substances.
• Mineral soils such as silica gel, silicas, silica gels, silicates, talc, kaolin, Attaclay, limestone, lime, chalk, bolus, loess, clay,
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90% by weight.
• the active substance concentrations in the ready-to-use preparations can be varied over a wide range.
• they are between 0.0001 and 10%, preferably between 0.01 and 1%.
• the active ingredients can also be used successfully in the fragrance
• Ultra-low-volume processes (ULV) are used, it being possible to apply formulations with more than 95% by weight of active ingredient or even the active ingredient without additives.
• the amount of active ingredient applied under field conditions is 0.2 to 10, preferably 0.5 to 2.0 kg / ha.
• Oils of various types, herbicides, fungicides, other pesticides, bactericides can be used as active ingredients, if appropriate also only immediately before use
• the active ingredients were:

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• 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)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

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Citations (3)

• 1993
  • 1993-01-14 CA CA002123324A patent/CA2123324A1/en not_active Abandoned
  • 1993-01-14 AU AU33494/93A patent/AU3349493A/en not_active Abandoned
  • 1993-01-14 HU HU9401351A patent/HUT67118A/hu unknown
  • 1993-01-14 CZ CZ941553A patent/CZ155394A3/cs unknown
  • 1993-01-14 JP JP5512139A patent/JPH07502998A/ja active Pending
  • 1993-01-14 WO PCT/EP1993/000060 patent/WO1993014079A1/de not_active Application Discontinuation
  • 1993-01-14 EP EP93902185A patent/EP0624158A1/de not_active Withdrawn
  • 1993-01-15 IL IL104408A patent/IL104408A0/xx unknown
  • 1993-01-20 MX MX9300282A patent/MX9300282A/es unknown
  • 1993-01-20 TW TW082100354A patent/TW229138B/zh active

Patent Citations (3)

Non-Patent Citations (2)

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