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EP1311496A1 - Thioethers de fluoralcenyle et utilisation en tant que pesticides (iii) - Google Patents

Thioethers de fluoralcenyle et utilisation en tant que pesticides (iii)

Info

Publication number
EP1311496A1
EP1311496A1 EP01960436A EP01960436A EP1311496A1 EP 1311496 A1 EP1311496 A1 EP 1311496A1 EP 01960436 A EP01960436 A EP 01960436A EP 01960436 A EP01960436 A EP 01960436A EP 1311496 A1 EP1311496 A1 EP 1311496A1
Authority
EP
European Patent Office
Prior art keywords
spp
optionally
substituted
chlorine
fluorine
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.)
Withdrawn
Application number
EP01960436A
Other languages
German (de)
English (en)
Inventor
Udo Kraatz
Bernd Gallenkamp
Albrecht Marhold
Peter Wolfrum
Wolfram Andersch
Christoph Erdelen
Andreas Turberg
Olaf Hansen
Achim Harder
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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 CropScience AG filed Critical Bayer CropScience AG
Publication of EP1311496A1 publication Critical patent/EP1311496A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/36—Sulfur atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
    • 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
    • A01N43/74—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 one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D263/46—Sulfur atoms

Definitions

  • the present invention relates to new heterocyclic fluoroalkenyl thioethers, processes for their preparation and their use as pesticides.
  • X represents hydrogen, halogen or alkyl
  • n 3 to 10
  • n 0, 1 or 2
  • Y represents sulfur or oxygen
  • R 1 for halogen for each optionally substituted by halogen alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or alkylcarbonyl, for optionally substituted cycloalkyl, stands for optionally substituted aryl or for optionally substituted heterocyclyl and
  • R 2 for hydrogen, halogen, for in each case optionally substituted by halogen alkyl, alkoxy, alkylthio, alkenyl, alkenyloxy, alkenylthio or
  • Alkylcarbonyl stands for optionally substituted cycloalkyl, for optionally substituted aryl or for optionally substituted heterocyclyl,
  • X and m have the meaning given above and Shark represents halogen, preferably bromine or chlorine,
  • Formula (LT) can also be used in the form of their salts, preferably the alkali metal salts, such as in particular the sodium or potassium salts; and if necessary
  • oxidized with an oxidizing agent optionally in the presence of a diluent and optionally in the presence of a catalyst.
  • the new heterocyclic fluoroalkenyl thioethers of the formula (I) have highly pronounced biological properties and, above all, for controlling animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forestry, in the protection of stocks and materials, and occur in the hygiene sector, are suitable.
  • Formula (I) provides a general definition of the heterocyclic fluoroalkenyl thioethers according to the invention. Preferred substituents or ranges of the radicals listed in the formulas mentioned above and below are explained below:
  • X preferably represents hydrogen, fluorine, chlorine, bromine or -CC-alkyl.
  • n preferably represents integers from 3 to 8.
  • n is preferably 0 or 2.
  • Y preferably represents sulfur
  • R 1 preferably represents fluorine, chlorine, bromine, each optionally mono- or polysubstituted, identically or differently, by halogen-substituted C1-CJO-alkyl, Ci-Cto-alkoxy, Ci-Cxo-alkylthio, C 2 -C 10 alkenyl, C 2 -C 10 alkenyloxy, C2-C ⁇ r j - alkenylthio or C ⁇ -C 10 - alkylcarbonyl, for optionally single to triple, identically or differently substituted by C1-C4-alkyl, C3-C6-cycloalkyl, for optionally single up to five times, identical or different by halogen, nitro, cyano, thiocyanato, in each case optionally one or more times, identical or different C1-C4-alkyl substituted by halogen,
  • Heterocyclyl with 1 to 3 N, O or S atoms Heterocyclyl with 1 to 3 N, O or S atoms.
  • R 2 preferably represents hydrogen, fluorine, chlorine or bromine, each optionally mono- or polysubstituted, identically or differently, by C 1 -C 8 -alkyl, C 1 -C 10 - alkoxy, C 1 -C 0 -alkylthio, C2- Cio-alkenyl, C2-C ⁇ o-alkenylo y, C 2 -C ⁇ 0 -alkenylthio or C ⁇ -C 10 -alkylcarbonyl, for optionally monosubstituted to trisubstituted, identically or differently, by C 1 -C 4 -alkyl substituted by C 1 -C 4 -cycloalkyl, for if necessary up to five times, the same or different
  • Halogen, nitro, cyano, thiocyanato each optionally mono- or polysubstituted, identically or differently by halogen-substituted C1-C4-alkyl, -C-C4 ⁇ alkoxy or C1-C4-alkylthio-substituted phenyl, or for optionally up to five times, identical or different 5- or 6-membered heterocyclyl with 1 to 3 substituted by halogen, nitro, cyano, thiocyanato, in each case optionally singly or multiply, identically or differently by halogen-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy or C1-C4 alkylthio N, O or S atoms.
  • X particularly preferably represents hydrogen or fluorine.
  • n particularly preferably represents integers from 4 to 6.
  • n particularly preferably represents 0.
  • R 1 particularly preferably represents fluorine or chlorine, each optionally mono- to quintuple, identically or differently, substituted by fluorine or chlorine -CC 6 alkyl, C r C 6 alkoxy, C 1 -C 6 -alkylthio, C 2 -C 6 -Alkenyl, C -Cg-alkenyloxy, C 2 -C6-alkenylthio or C 2 -C6 ⁇ alkylcarbonyl, for each optionally mono- or disubstituted, identically or differently, by cyclopropyl, cyclopentyl or cyclohexyl substituted by methyl, ethyl, n- or i-propyl , for optionally single to triple, identical or different by fluorine, chlorine, bromine, nitro, cyano, thiocyanato, each optionally single to fivefold, identical or different by fluorine or chlorine substituted C1-
  • C4-AU VI, -C-C4-alkoxy or C1-C4-alkylthio substituted phenyl or for each optionally monosubstituted to trisubstituted, identically or differently, by fluorine, chlorine, bromine, nitro, cyano, thiocyanato, in each case optionally monosubstituted to fivefold, identically or differently by C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or C r C 4 - alkylthio substituted furyl, thienyl, pyrazolyl, pyridinyl or pyrimidinyl.
  • R 2 particularly preferably represents hydrogen, fluorine or chlorine, each optionally mono- to fivefold, identically or differently substituted by fluorine or chlorine, C r C 6 alkyl, C r C 6 alkoxy, C 1 -C 6 alkylthio, C 2 -C 6 - alkenyl, C 2 -Cg alkenyloxy, C 2 -C ⁇ - alkenylthio or C -C 6 - alkylcarbonyl, for each optionally single or double, identical or different by methyl, ethyl, n- or i-propyl Substituted cyclopropyl, cyclopentyl or cyclohexyl, for optionally single to triple, identical or different by fluorine, chlorine, bromine, nitro, cyano, thiocyanato, in each case optionally single to fivefold, identical or different substituted by fluorine or chlorine Ci-C4-alkyl, C ⁇ -C 4 -alkoxy
  • n very particularly preferably stands for 4.
  • R 1 very particularly preferably represents chlorine, in each case optionally up to five times, the same or differently substituted by fluorine or chlorine
  • Methyl, ethyl, n- or i-propyl for methoxy or ethoxy, for methylthio or ethylthio, for ethenyl, propenyl, butenyl, pentenyl or hexenyl, for methylcarbonyl or ethylcarbonyl, or for phenyl which is optionally mono- or disubstituted, identically or differently, by fluorine, chlorine, nitro, cyano, thiocyanato, in each case optionally mono- to pentasubstituted by fluorine or chlorine, substituted by fluorine or chlorine, methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio.
  • R 2 very particularly preferably stands for hydrogen, for chlorine, for methyl, ethyl, n- or i-propyl, which is optionally mono- to pentasubstituted in the same or different manner by fluorine or chlorine, for methoxy or ethoxy, for methylthio or ethylthio, for ethenyl , Propenyl, butenyl,
  • Pentenyl or hexenyl for methylcarbonyl or ethylcarbonyl, or for optionally single or double, identical or different by fluorine, chlorine, nitro, cyano, thiocyanato, each optionally optionally up to five times, identical or different substituted by fluorine or chlorine, methyl, ethyl, methoxy, Ethoxy, methylthio or ethylthio substituted
  • R 1 most preferably represents chlorine, optionally mono- to trisubstituted by fluorine-substituted methyl or phenyl.
  • R 2 most preferably represents hydrogen, chlorine, optionally mono- to trisubstituted by fluorine-substituted methyl or phenyl.
  • hydrocarbon radicals such as alkyl - are also straight-chain or branched as far as possible, even in compounds with heteroatoms such as in alkoxy.
  • X represents hydrogen or fluorine
  • n 0, 1 or 2
  • Y represents sulfur or oxygen
  • R 1 and R 2 have one of the above definitions. If, for example, 2-mercapto-4-phenyl-l, 3-thiazole and 6,6,5-trifluorohex-5-enylbromide are used as starting materials, the course of the reaction of process (a) according to the invention can be represented by the following formula:
  • Formula (H) provides a general definition of the mercapto derivatives to be used as starting materials for carrying out process (a) according to the invention.
  • the mercapto derivatives of the formula (II) are largely known or commercially available and / or can be prepared in analogy to known processes (cf. e.g.
  • Formula (III) provides a general definition of the fluoroalkenyl halides to be used as starting materials in process (a) according to the invention.
  • the fluoroalkenyl halides of the formula (III) are known (see, for example, J. Chem. Soc. Perkin Trans. 2, 219 (1998); Tetrahedron Lett. 37, 5321 (1996); EP 0 334 796 or WO 95/4727) or commercially available.
  • Inert organic solvents are suitable as diluents for carrying out process (a) according to the invention.
  • diluents for carrying out process (a) according to the invention.
  • These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, anisole, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, 1,2-dichloroethane,
  • Chloroform, carbon tetrachloride Ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones such as acetone or butanone; Nitriles such as acetonitrile or propionitrile; Amides, such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethyl triamide; Esters such as ethyl acetate; Sulfoxides, such as dimethyl sulfoxide or sulfolane; but also alcohols, such as methanol, ethanol or isopropanol.
  • Ethers such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether
  • Ketones such as acetone or butanone
  • Nitriles such as acetonitrile or propion
  • Process (a) according to the invention can, if appropriate, be carried out in the presence of a basic reaction auxiliary.
  • All conventional inorganic or organic bases are suitable as such. These include, for example, alkali metal and alkaline earth metal hydroxides, such as sodium hydroxide, potassium hydroxide or calcium hydroxide, alkali metal carbonates or hydrogen carbonates, such as sodium carbonate, potassium carbonate, cesium carbonate or sodium hydrogen carbonate, and also tertiary amines, such as triethylamine, N, N-dimethylaniline, pyridine, N, N - Dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicycloundecene (DBU).
  • alkali metal and alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide or calcium hydroxide
  • alkali metal carbonates or hydrogen carbonates such as sodium carbonate, potassium carbonate, ces
  • reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C and + 200 ° C, preferably at temperatures between + 20 ° C and + 140 ° C.
  • reaction products 0.3 to 3.0 mol, preferably a slight excess, of fluoroalkenyl halide of the formula (III) and, if appropriate, 0.5 to 2, are generally employed per mol of mercapto derivative of the formula (IT) , 0 moles, preferably 0.5 to 1.0 mole of reaction auxiliary.
  • the reaction, working up and isolation of the reaction products is carried out according to generally customary methods.
  • Suitable oxidizing agents for carrying out process (b) according to the invention are all customary oxidizing agents which can be used for sulfur oxidation.
  • Hydrogen peroxide, organic and inorganic peracids such as, for example, peracetic acid, m-chloroperbenzoic acid, p-nitroperbenzoic acid, magnesium peroxiphthalic acid, potassium peroximonosulfate or are particularly suitable
  • Inert organic solvents are also suitable as diluents for carrying out process (b) according to the invention.
  • Hydrocarbons such as gasoline, benzene, toluene, hexane or petroleum ether, are preferably used; chlorinated hydrocarbons, such as dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride or chlorobenzene; Ethers such as diethyl ether, dioxane or tetrahydrofuran; Carboxylic acids, such as formic acid, acetic acid or propionic acid, or dipolar aprotic solvents, such as acetonitrile, acetone, ethyl acetate or dimethylformamide; optionally also in aqueous solutions.
  • process (b) according to the invention can be carried out in the presence of a suitable catalyst.
  • a suitable catalyst All metal salt catalysts customarily used for such sulfur oxidations are suitable as such. Examples include ammonium molybdate and sodium tungstate.
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between -20 ° C and + 120 ° C, preferably at temperatures between 0 ° C and + 100 ° C.
  • 0.8 to 1.2 mol, preferably equimolar amounts, of oxidizing agent are generally used per mole of compound of the formula (Ia) if one wishes to interrupt the oxidation of the sulfur at the sulfoxide stage. For the oxidation to the sulfone one starts per mole
  • Compound of formula (Ia) generally 1.8 to 3.0 mol, preferably double molar amounts of oxidizing agent.
  • the implementation, processing and isolation of the end products is carried out using customary methods.
  • the active substances are suitable for controlling animal pests, especially insects, Arachnids and nematodes found in agriculture, in forests, in the protection of Vonats and materials, and in the hygiene sector. They can preferably be used as pesticides. 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 e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera for example Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera for example Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentahs.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Anthonomus spp. Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Agrebri molitor, Tenebrio molitor. Conoderas spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tabanus spp.
  • Tannia spp. Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp ..
  • Plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Tripusichpp. Spp., Xiphinema spp.
  • the compounds according to the invention can be used with particularly good success for combating nematodes which damage plants, such as, for example, against Meloidogyne incognita larvae; for combating plant-damaging insects, such as, for example, against the peach aphid (Myzus persicae) and the larvae of the horseradish beetle (Phaedon cochleariae); as well as to combat harmful plants
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungal agents and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and undesirable wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • plants and their parts can be treated according to the invention.
  • wild or by conventional organic breeding methods such as crossing or Protoplast fusion obtained plant species and plant varieties and their parts treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetic modified organisms) and their parts are treated.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant cultivars are understood to mean plants with new properties ("traits") which are produced both by conventional breeding, by mutagenesis or by recombinant DNA
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering performance , easier harvesting, acceleration of ripeness, higher crop yields, higher quality and or higher nutritional value of the harvested products, higher storability and / or workability of the harvested products possible, which go beyond the expected effects.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased
  • Tolerance to high or low temperatures increased tolerance to Dryness or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the harvested products.
  • Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicidal active ingredients.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), CryIA (c), CryllA,
  • Bt plants CryllLA, CryflTB2, Cry9c Cry2Ab, Cry3Bb and CryLF as well as their combinations
  • the properties (“traits”) also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
  • SAR systemic acquired resistance
  • the properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example “PAT” gene).
  • Bt plants are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • YIELD GARD® e.g. corn, cotton, soy
  • KnockOut® e.g. corn
  • StarLink® e.g. corn
  • Bollgard® Cotton
  • Nucotn® cotton
  • NewLeaf® NewLeaf®
  • Plants are maize varieties, cotton varieties and soy varieties that are among the Trade names Roundup Ready® (tolerance against glyphosate eg maize, cotton, soy), Liberty Link® (tolerance against phosphinotricin, eg rape), LMI® (tolerance against imidazolinones) and STS® (tolerance against sulfonylureas eg maize).
  • the herbicide-resistant plants include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention.
  • the preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants.
  • Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying,
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is liquid solvents and / or solid
  • Carriers optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
  • Possible solid carriers are: e.g. Ammonium salts and natural rock flours, such as kaolins, clays,
  • Talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
  • non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: e.g. Lignin sulfate leachate 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 phospho- lipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferocyan 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% by weight of active compound, preferably between 0.5 and 90%.
  • the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, 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.
  • Aldimorph ampropylfos, ampropylfos potassium, andoprim, anilazine, azaconazole, azoxystrobin, benalaxyl, benodanil, benomyl, benzamacril, benzamacrylic isobutyl, bialaphos,
  • Famoxadone Fenapanil, fenarimol, fenbuconazole, Fen
  • Fen assumes that the following abbreviations: Fena is a tensile strength at the end of the tensile strength at the end of the tensile strength at the end of the tensile strength at the end of the tensile strength at the end of the tensile strength at the end of the tensulfa ⁇ iid, flutolanil, flutriafol, folpet, fosetyl-Alrriinium, Fosetyl sodium, fthalide, fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole, furconazole-cis,
  • copper preparations such as: copper hydroxide, copper phthalate, copper oxychloride, copper sulfate, copper oxide, oxine-copper and Bordeaux mixture, Mancopper, Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl,
  • Metconazole Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin, Nickel-dimethyldithiocarbamate, Nitrothal-isopropyl, Nuarimol, Ofurace, Oxadixyl, Oxamocarb, Oxoliniciminol, Pylobenzolimidolacid, Oxyoboxiloximolin, Oxyobenzolimidolacid, Oxyocidoximidolacid, Oxyacidoximolin, Oxyacid Oximidolimid, Oxyacid Oximidolimid, Oxyacid Oximicolin, Oxyacid Oximidolacid, Oxyacid Oximidolacid, Oxyacid Oximidocimine, Oxyacid Oximidolacin, Oxyacid Oximidolacid, Oxyacid Oximicolin, Oxyacid Oximine, Oxyacid Oximate
  • Thicyofen Thifluzamide, Thiophanate-methyl, Thiram, Tioxymid, Tolclofos-methyl,
  • Tridemorph triflumizole, triforin, triticonazole, uniconazole,
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxinon, Fluthrinoxin, Fluutinoxin, Fluutinoxin , Fubfenprox, Furathiocarb,
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • 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 that increase the effectiveness of the active ingredients 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 ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • Active ingredient characterized by an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates.
  • the active compounds according to the invention act not only against plant, hygiene and Vonat pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • Ischnocerina e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp ..
  • Nematocerina and Brachycerina for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp.
  • Atylotus spp. Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..
  • Amblyomma spp. Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Vanoa spp ..
  • the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are agricultural animals, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • arthropods are agricultural animals, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • the agents according to the invention are suitable for combating pathogenic endoparasites which occur in humans and in animal husbandry and animal breeding in farm animals, breeding, zoo, laboratory, experimental and hobby animals. They are against all or individual stages of development of the pests and against resistant and normally sensitive species are effective.
  • pathogenic endoparasites include cestodes, trematodes, nematodes, acantocephals in particular:
  • Cyclophyllidea for example: Mesocestoides spp., Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosomsa spp., Thysaniezia spp., Avitelellina spp., Stilesia spp., Cittotaenia spp., Andyella spp., Bertella spp spp., Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipyhdium spp., Joyeuxiella spp.,
  • Paramphistomum spp. Calicophoron spp., Cotylophoron spp., Gigantocotyle spp Fischoederius spp., Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosmogonimus spp., Dicrocoytrium sppema. Paragonimus spp., Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp. Metorchis spp., Heterophyes spp., Metagonimus spp .. From the order of the Enoplida, for example: Trichuris spp., CapiUaria spp., Trichomosoides spp., Trichinella spp ..
  • Stronylus spp. Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cyhcostephanus sppabia, spp., Oesost. , Stephanurus spp., Ancylostoma spp., Uncinaria spp., Bunostomum spp.,
  • Globocephalus spp. Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Spicocaulus spp. Parelaphostrongylus spp., Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp.,
  • Aelurostrongylus spp. Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Marshallagia spp., Cooperia spp., Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostom ..
  • Oxyurida From the order of the Oxyurida, for example: Oxyuris spp., Enterobius spp., Passalurus spp.,
  • Ascaridia for example: Ascaris spp., Toxascaris spp., Toxocara spp., Parascaris spp., Anisakis spp., Ascaridia spp ..
  • Spirurida for example: Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., Dracunculus spp ..
  • Filariida for example: Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp., Brugia spp., Wuchereria spp., Onchocerca spp ..
  • Livestock and breeding animals include mammals such as Cattle, horses, sheep, pigs, goats, camels, water buffalos, donkeys, rabbits, fallow deer, reindeer, fur animals such as Mink, chinchilla, raccoon, birds such as Chickens, geese, turkeys,
  • Ducks, ostriches, fresh and saltwater fish such as Trout, carp, eels, reptiles, insects such as Honey bee and silkworm.
  • Laboratory and experimental animals include mice, rats, guinea pigs, golden hamsters, dogs and cats.
  • the pets include dogs and cats.
  • the application can be prophylactic as well as therapeutic.
  • the active ingredients are used directly or in the form of suitable preparations enterally, parenterally, dermally, nasally, by treating the environment or with the aid of shaped articles containing active ingredients, e.g. Strips, plates, ribbons, collars, ear tags, limb straps, marking devices.
  • the enteral application of the active ingredients takes place, for example, orally in the form of powder, tablets, capsules, pastes, drinkers, granules, orally administrable solutions, suspensions and emulsions, boluses, medicated feed or drinking water.
  • the dermal application takes place, for example, in the form of dipping (dipping), spraying (spraying) or pouring on (pour-on and spot-on).
  • Parenteral use happens for example in the form of injection (intramuscular, subcutaneous, intravenous, intraperitoneal) or by implants.
  • Suitable preparations are:
  • Solutions such as injection solutions, oral solutions, concentrates for oral administration after dilution, solutions for use on the skin or in body cavities, pour-on formulations, gels;
  • Emulsions and suspensions for oral or dermal use and for injection are Emulsions and suspensions for oral or dermal use and for injection; semi-solid preparations;
  • Solid preparations such as powders, premixes or concentrates, granules, pellets, tablets, boluses, capsules; Aerosols and inhalants, molded articles containing active ingredients.
  • Injection solutions are administered intravenously, intramuscularly and subcutaneously.
  • Injection solutions are prepared by dissolving the active ingredient in a suitable solvent and possibly adding additives such as solubilizers, acids, bases, buffer salts, antioxidants, preservatives.
  • additives such as solubilizers, acids, bases, buffer salts, antioxidants, preservatives.
  • the solutions are sterile filtered and filled.
  • solvents physiologically compatible solvents such as water, alcohols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, and mixtures thereof.
  • the active compounds can also be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.
  • solubilizers solvents which promote the dissolution of the active ingredient in the main solvent or prevent its precipitation. Examples are polyvinyl pyrrolidone, polyoxyethylated castor oil, polyoxyethylated sorbitan esters.
  • Preservatives are: benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid ester, n-butanol.
  • Oral solutions are applied directly. Concentrates are used orally after prior dilution to the application concentration. Oral solutions and
  • Concentrates are prepared as described above for the injection solutions, whereby sterile work can be dispensed with.
  • Solutions for use on the skin are dripped on, spread on, rubbed in, sprayed on or sprayed on. These solutions are prepared as described above for the injection solutions.
  • Thickeners are: inorganic thickeners such as bentonites, colloidal silica, aluminum monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and metacrylates.
  • Gels are applied to or spread on the skin or placed in body cavities. Gels are produced by adding enough thickening agent to solutions which have been prepared as described for the injection solutions to give a clear mass with an ointment-like consistency.
  • the thickeners specified above are used as thickeners.
  • solvents water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerin, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol, mono-butyl glycol, mono Acetone, methyl ethyl ketone, aromatic and or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetide, N-methylpynolidone, 2,2-dimethyl-4-oxy-methylene-l, 3-dioxolane.
  • aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol
  • esters such as ethyl acetate, butyl acetate
  • benzyl benzoate ethers
  • Dyes are all dyes approved for use on animals, which can be dissolved or suspended.
  • Absorbing substances are e.g. DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols.
  • spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils, fatty acid esters, triglycerides, fatty alcohols.
  • Antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid,
  • Light stabilizers are e.g. Novantisol acid.
  • Adhesives are e.g. Cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.
  • Emulsions can be used orally, dermally or as injections.
  • Emulsions are either water in oil or oil in water. They are produced by dissolving the active ingredient either in the hydrophobic or in the hydrophilic phase and homogenizing it with the solvent of the other phase with the aid of suitable emulsifiers and, if necessary, other auxiliaries such as dyes, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-increasing substances ,
  • hydrophobic phase paraffin oils, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic / capric acid biglyceride, triglyceride mixture with vegetable fatty acids of chain length C 8 to 12, or other natural fatty acids, partial glyceride mixtures of specially selected saturated or unsaturated, possibly also hydroxyl-containing fatty acids, mono- and diglycerides of Cs / Cio fatty acids.
  • Fatty acid esters such as ethyl stearate, di-n-butyryl adipate, lauric acid hexyl ester, dipropylene glycol pelargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C 16 -C 18 , isopropyl myristate, isopropyl palmitate, caprylic / capric acid esters of saturated fatty alcohol chain length C 12 -C 1 8, oleyl oleate, decyl oleate, ethyl oleate, lactic acid ethyl ester, waxy fatty acid ester such as artificial duck preen gland oil, dibutyl phthalate, diisopropyl adipate, related to the latter inter alia Estergemische
  • Fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol.
  • Fatty acids such as Oleic acid and its mixtures.
  • hydrophilic phase The following can be mentioned as the hydrophilic phase:
  • nonionic surfactants for example polyoxyethylated castor oil, polyoxyethylene sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;
  • ampholytic surfactants such as di-Na-N-lauryl- ⁇ -iminodipropionate or lecithin;
  • anionic surfactants such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono dialkyl polyglycol ether morphophosphate monoemanolamine salt;
  • cationic surfactants such as cetyltrimethylammonium chloride.
  • auxiliaries that may be mentioned are: viscosity-increasing and emulsion-stabilizing substances such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpynolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycoloids, waxes Silicic acid or mixtures of the listed substances.
  • viscosity-increasing and emulsion-stabilizing substances such as carboxymethyl cellulose, methyl cellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpynolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycoloids, waxes Silicic acid or mixtures of the listed substances.
  • Suspensions can be used orally, dermally or as an injection. They are produced by placing the substance in a carrier liquid, if necessary
  • auxiliaries such as wetting agents, dyes, absorption-promoting substances, preservatives, antioxidants, light stabilizers suspended.
  • the surfactants specified above may be mentioned as wetting agents (dispersants).
  • Semi-solid preparations can be administered orally or dermally. They differ from the suspensions and emulsions described above only in their higher viscosity.
  • the material is mixed with suitable carriers, if appropriate with the addition of auxiliaries, and brought into the desired shape.
  • Inorganic and organic substances serve as such. Inorganic substances are e.g.
  • Table salt carbonates such as calcium carbonate, hydrogen carbonates, aluminum oxides, silicas, clays, precipitated or colloidal silicon dioxide, phosphates.
  • Organic substances are e.g. Sugar, cellulose, food and animal feed such as milk powder, animal meal, cereal flour and meal, starches.
  • Excipients are preservatives, antioxidants, dyes, which have already been listed above.
  • auxiliaries are lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decay promoting substances such as starch or cross-linked polyvinylpynolidone, binders such as e.g. Starch, gelatin or linear polyvinylpynolidone as well as dry binders such as microcrystalline cellulose.
  • lubricants and lubricants such as Magnesium stearate, stearic acid, talc, bentonite, decay promoting substances such as starch or cross-linked polyvinylpynolidone, binders such as e.g. Starch, gelatin or linear polyvinylpynolidone as well as dry binders such as microcrystalline cellulose.
  • the active ingredients can also be present in the preparations as a mixture with synergists or with other active ingredients which act against pathogenic endoparasites.
  • Such materials are e.g. L-2,3,5,6-Tehahydro-6-phenyl-imidazothiazole,
  • Benzimidazole carbamates, pyrantel. Ready-to-use preparations contain the active ingredients in concentrations of 10 ppm - 20 percent by weight, preferably 0.1-10 percent by weight.
  • Preparations which are diluted before use contain the active substances in concentrations of 0.5-90% by weight, preferably from 5 to 50% by weight.
  • compositions generally maintain a weight ratio of praziquantel or epsiprantel to depsipeptide, such as 1 to 1 to 10, preferably 1 to 1 to 2, very particularly preferably 1 to 1.
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Lyctus pubescens Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus.
  • Kalotermes flavicolhs Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitennes lucifugus, Mastotennes darwiniensis, Zootermopsis nevadensis, Coptotennes fonnosanus.
  • Bristle tails such as Lepisma saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the material to be protected against insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • Lumber wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles,
  • the active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active ingredients with at least one solution or
  • Diluents Diluents, emulsifiers, dispersants and / or binders or fixatives, Water repellants, optionally desiccants and UV stabilizers and optionally dyes and pigments as well as other processing aids.
  • insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active substance according to the invention in a concentration of
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
  • An organic-chemical solvent or solvent mixture and / or an oily or oil-like low-volatility organic-chemical solvent or solvent mixture and or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier are used as solvents and / or diluents and / or wetting agents.
  • the organic chemical solvents used are preferably oily or oily ones
  • Solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, are used.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or locker oil and / or monochlomaphthalene, preferably ⁇ -monochlomaphthalene, are used.
  • the organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and has a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
  • Solvent or solvent mixture replaced by a polar organic chemical solvent or solvent mixture.
  • Organochemical solvents containing hydroxyl and / or ester and / or ether groups such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic water-borne synthetic resins and / or binding drying oils, in particular binders consisting of or containing an acrylate resin are known as water-thinnable and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used
  • Vinyl resin for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as Inden-Curnaron resin, silicone resin, drying vegetable and / or squatting oils and / or physically drying binders based on a natural and / or synthetic resin used.
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, vegetable correctives and inhibitors or anti-corrosion agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins having an oil content of more than 45% by weight, preferably 50 to, are preferred according to the invention
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the materials and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycerol or glycerol ether - Kolether, glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chlorpyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, methoxyphenurophen, thiaphenoxidur,
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro - octylisothiazolin-3-one.
  • the compounds according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • heavy metals such as e.g. in bis (trialkyltin) sulfides, tri - "- butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, triethyltin chloride, tri -" - butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide , Antimony oxide, polymeric butyl titanate, phenyl (bispyridine) - bismuth chloride, tri - «- butyltin fluoride, manganese ethylene bisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinethiol-1-oxide, bisdimethyldihidyldihamidoxydiaminodiaminodisulfide, bisd
  • the ready-to-use antifouling paints can optionally contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Algicides like 2-tert-butylarrnO ⁇ -4-cyclopropylammo-6-methyltMo-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;
  • Benzo [b] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanid, fluorofolpet, 3-iodo-2-propynyl-butylcarbamate, tolylfluanid and azoles such as
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.
  • the antifouling agents according to the invention furthermore contain the usual constituents, e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams,
  • antifouling Marine Coatings Noyes, Park Ridge, 1973.
  • antifouling paints contain in particular binders.
  • binders examples include polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / Acrylonitrile rubbers, squatting
  • Oils such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic
  • Paints may also contain materials such as rosin to enable controlled release of the active ingredients.
  • the paints may also contain plasticizers, modifiers affecting theological properties, and other conventional ingredients. Also in self-polishing antifouling
  • the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins and others. occurrence.
  • Acarina for example Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Omithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
  • Psocoptera for example Lepinatus spp., Liposcelis spp.
  • Coleptera for example Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselhella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fiiliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • the application in the field of household insecticides is carried out alone or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, growth regulators or active ingredients from other known classes of insecticides. They are used in aerosols, unpressurized sprays, e.g. pump and atomizer sprays, automatic fog machines, foggers, foams, gels, vaporizer products with vaporizer plates made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energy-free or passive evaporation systems, moth papers , Moth bags and moth angels, as granules or dusts, in lures or bait stations.
  • suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, growth regulators or active ingredients from other known classes of insecticides. They are used in aerosols, unpressurized sprays, e.g. pump and atomizer sprays, automatic fog machines, fogger
  • logP values were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (gradient method, acetonitrile / 0.1% aqueous phosphoric acid).
  • Solvent 30 parts by weight of dimethylformamide or 4 parts by weight of acetone
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active substance is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larva suspension and lettuce seeds.
  • the lettuce seeds germinate and the plants develop.
  • the galls develop at the roots.
  • the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% effect means that the number of galls on the treated plants corresponds to that of the untreated control.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active substance preparation 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • 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%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • the compound of preparation example 6 shows a kill of 95% after 6 days.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the preparation of the desired concentration and populated with larvae of the horseradish beetle (Phaedon cochleariae) while the leaves are still moist.
  • the kill is determined in%. 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
  • Bean plants Phaseolus vulgaris
  • Tetranychus urticae which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Test animals adult sucked females
  • the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The pulp control takes place after 7 days on the storage of fertile eggs. Eggs, whose fertility is not visible from the outside, are kept in glass tubes until larvae hatch in the climatic chamber. An effect of 100% means that no tick has laid fertile eggs.
  • Test animals adults of Ctenocephalides felis
  • a suitable active ingredient solution is prepared from 20 mg of active ingredient with 1 ml of DMSO. 15 ⁇ l of this formulation are added to 3 ml of citrated bovine blood and stirred.
  • Fleas can be absorbed through the parafilm membrane. While the blood is being heated to 37 ° C, a temperature of 25 ° C is set in the area of the flea chambers. Controls are mixed with the same volume of DMSO without the addition of a compound. Triple determinations are carried out.
  • Example G In this test, at an exemplary active substance concentration of 100 ppm, the compound of preparation example 4, for example, shows a kill of 100%.
  • Example G In this test, at an exemplary active substance concentration of 100 ppm, the compound of preparation example 4, for example, shows a kill of 100%.
  • Test animals Lucilia cuprina larvae
  • test tube which contains approx. 1 cm 3 horse meat and 0.5 ml of the pulp preparation to be tested.
  • the effectiveness of the active substance preparation is determined after 24 and 48 hours.
  • the test tubes are transferred to beakers with a sand-covered bottom. After a further 2 days, the test tubes are removed and the dolls are counted.
  • the effect of the active substance preparation is assessed according to the number of flies hatched after 1.5 times the development time of an untreated control. 100% means that no flies have hatched; 0% means that all flies hatched normally.
  • the compound of preparation example 8 shows a kill of 100%.
  • Nipposhongylus brasiliensis worms are isolated from the small intestine of female Wistar rats and collected in aqueous 0.9% NaCl containing 20 ⁇ g / ml sisomycin and 2 ⁇ g / ml canesten.
  • the incubation of both worm groups (male / female sex) is carried out in 1.0 ml medium, which is used for the determination of the acetylcholinesterase activity.
  • the incubation conditions and the determination of the enzyme activity were described in Martin et al., Pesticide Science (1996) 48, 343-349.
  • the compounds are dissolved in the specified solvent (10 mg to 0.5 ml) and to the desired one
  • the vitality of the worms is characterized by the activity of acetylcholinesterase, which the worms actively secreted into the incubation medium.
  • the classification of acetylcholinesterase activity follows the work of
  • Test animals Trichinella spiralis larvae
  • Trichinella spiralis larvae are isolated from the skeletal muscles and muscles below the skin of SPF / CFW1 mice and collected in aqueous 0.9% NaCl containing 20 ⁇ g / ml sisomycin. 20 larvae in 2 ml of a
  • test compound 10 mg are dissolved in 0.5 ml of the specified solvent and enough of the solution obtained is added to the incubation medium such that the desired concentration is reached.
  • the controls contain only the solvent.
  • the experiment is ended after an incubation period of 5 days at a temperature of 19 ° C.
  • the anthelmintic activity of a substance is divided into 4 levels. 0 means no, 1 weak, 2 good and 3 full activity ( ⁇ 50%, 50 - 75%,> 75%, 100% of the larvae dead).

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  • Life Sciences & Earth Sciences (AREA)
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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Environmental Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne de nouveaux thioéthers de fluoralcényle hétérocycliques de la formule (I) dans laquelle X est hydrogène, halogène, ou alkyle ; m est un entier de 3 à 10 ; n est 0, 1 ou 2 ; Y est soufre ou oxygène; R<1> est halogène, ou alkyle, alkoxy, alkylthio, alcényle, alcényloxy, alcénylthio ou alkylcarbonyle éventuellement substitués par halogène, ou cycloalkyle éventuellement substitué, ou aryle ou hétérocyclyle éventuellement substitués ; et R<2> est hydrogène, halogène, ou alkyle, alkoxy, alkylthio, alcényle, alcényloxy, alcénylthio ou alkylcarbonyle éventuellement substitués par halogène, ou cycloalkyle éventuellement substitué, ou aryle ou hétérocyclyle éventuellement substitués, les compositions dans lesquelles R<1> = alkyle, Y = oxygène et X = hydrogène étant exclues selon l'invention. L'invention concerne également des procédés de fabrication de ces composés ainsi que leur utilisation en tant que pesticides.
EP01960436A 2000-07-13 2001-07-02 Thioethers de fluoralcenyle et utilisation en tant que pesticides (iii) Withdrawn EP1311496A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE10034132A DE10034132A1 (de) 2000-07-13 2000-07-13 Heterocyclische Fluoralkenylthioether (lll)
DE10034132 2000-07-13
PCT/EP2001/007520 WO2002006257A1 (fr) 2000-07-13 2001-07-02 Thioethers de fluoralcenyle et utilisation en tant que pesticides (iii)

Publications (1)

Publication Number Publication Date
EP1311496A1 true EP1311496A1 (fr) 2003-05-21

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US (1) US20040106658A1 (fr)
EP (1) EP1311496A1 (fr)
JP (1) JP2004504310A (fr)
AU (1) AU2001281928A1 (fr)
DE (1) DE10034132A1 (fr)
WO (1) WO2002006257A1 (fr)
ZA (1) ZA200300275B (fr)

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DE10221119A1 (de) * 2002-05-13 2003-12-04 Bayer Cropscience Ag Verfahren zur Herstellung von substituierten Trifluorethylenen
DE10221120A1 (de) * 2002-05-13 2003-11-27 Bayer Cropscience Ag Verfahren zur Herstellung von substituierten Trifluorethylenen
DE10229776A1 (de) 2002-07-03 2004-01-22 Bayer Cropscience Ag Verfahren zum Herstellen von heterocyclischen Fluoralkenylsulfonen
KR20200112816A (ko) * 2017-12-20 2020-10-05 피아이 인더스트리스 엘티디. 불소알킬 화합물의 제조와 사용방법
WO2020095161A1 (fr) 2018-11-05 2020-05-14 Pi Industries Ltd. Composés nitrones et leur utilisation
WO2021024253A1 (fr) * 2019-08-04 2021-02-11 Yeda Research And Development Co. Ltd. Procédé de préparation de fluensulfone
AR121893A1 (es) * 2020-04-22 2022-07-20 Sumitomo Chemical Co Compuesto de fenilo y método para controlar enfermedades vegetales

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Publication number Priority date Publication date Assignee Title
US3914251A (en) * 1971-12-08 1975-10-21 Stauffer Chemical Co Certain trifluorobutenyl compounds and their utility as nematocides
DE2344134A1 (de) * 1973-09-01 1975-03-13 Bayer Ag Kohlensaeurederivate des 2-mercapto-4,5dichlor-thiazols, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
HU204022B (en) * 1985-06-20 1991-11-28 Fmc Corp Nematocidal compositions comprising polyhalogen alkene derivatives and process for producing polyhalogen alkene derivatives
DE58904307D1 (de) * 1988-03-19 1993-06-17 Hoechst Ag Verfahren zur herstellung von ungesaettigten halogenierten kohlenwasserstoffen.
DE69430667T2 (de) * 1993-08-05 2003-02-06 Syngenta Ltd., Haslemere Verfahren zur herstellung von fluoralkenylthio heterozyclische derivate
IL112721A0 (en) * 1994-03-10 1995-05-26 Zeneca Ltd Azole derivatives
GB2293380A (en) * 1994-09-22 1996-03-27 Zeneca Ltd Pesticidal heterocyclic and phenyl compounds
WO1999052874A1 (fr) * 1998-04-10 1999-10-21 Ube Industries, Ltd. Derives difluoroalcene, procede de production associe, et agent de lutte contre les ravageurs dans l'agriculture et l'horticulture
JP2001019685A (ja) * 1999-07-06 2001-01-23 Nippon Bayer Agrochem Co Ltd 殺センチュウ性トリフルオロブテン類
DE10034130A1 (de) * 2000-07-13 2002-01-24 Bayer Ag Heterocyclische Fluoralkenylthioether (lV)

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See references of WO0206257A1 *

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ZA200300275B (en) 2004-01-30
US20040106658A1 (en) 2004-06-03
AU2001281928A1 (en) 2002-01-30
DE10034132A1 (de) 2002-01-24
WO2002006257A1 (fr) 2002-01-24
JP2004504310A (ja) 2004-02-12

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