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EP1846398A1 - Alkinyl-oxypyrimidine used in the form of pesticides - Google Patents

Alkinyl-oxypyrimidine used in the form of pesticides

Info

Publication number
EP1846398A1
EP1846398A1 EP05821899A EP05821899A EP1846398A1 EP 1846398 A1 EP1846398 A1 EP 1846398A1 EP 05821899 A EP05821899 A EP 05821899A EP 05821899 A EP05821899 A EP 05821899A EP 1846398 A1 EP1846398 A1 EP 1846398A1
Authority
EP
European Patent Office
Prior art keywords
spp
substituted
chlorine
alkyl
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Withdrawn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
EP05821899A
Other languages
German (de)
French (fr)
Inventor
Thomas Bretschneider
Olga Malsam
Mark-Wilhelm Drewes
Christian Arnold
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 EP1846398A1 publication Critical patent/EP1846398A1/en
Withdrawn legal-status Critical Current

Links

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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present application relates to novel substituted pyrrolidines, processes for their preparation and their use in agents for combating animal pests, especially arthropods, in particular insects.
  • A is a single bond or O (oxygen), S (sulfur), NH, N (C 1 -C 4 -alkyl), a
  • R 1 represents optionally halogen-substituted, straight-chain or branched alkynyl having 2 to 10 carbon atoms
  • R 2 is hydrogen, amino, halogen or halogen-substituted, straight-chain or branched alkyl having 1 to 4 carbon atoms,
  • R 3 represents hydrogen, amino, halogen or optionally halogen-substituted, straight-chain or branched alkyl having 1 to 4 carbon atoms, and
  • R 4 is a monocyclic or bicyclic radical, optionally substituted by nitro, hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, by any given substituted by hydroxy, cyano or halogen substituted Ci-C 6 alkyl, Ci-C 6 alkyl carbonyl, C r C 6 alkoxy d-5 CSS-alkoxy-carbonyl, C r C 6 alkylthio, C r C 6 alkylsulfinyl, Q-Cs-alkylsulfonyl, C r C6-alkylamino, Ci-Ce-alkyl-aminocarbonyl, di- (Ci -C 6 alkyl) - amino, di (C r C 6 alkyl) amino-carbonyl or substituted heteroaromatic group having up to 9 carbon atoms and at least one heteroatom from the series N (nitrogen, 1 to 5 N
  • R 2 , R 3 and R 4 have the meanings given above and
  • X 1 is halogen or C 1 -C 4 -alkylsulfonyl
  • R 1 has the meaning given above
  • R 1 , R 2 and R 3 have the meanings given above and
  • X 2 is halogen or C 1 -C 4 -alkylsulfonyl
  • a and R 4 have the meanings given above
  • reaction auxiliaries if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents.
  • novel compounds of the formula (I) have pronounced biological properties and, in particular, for controlling animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forestry, in the protection of stored products and materials, and in the hygiene sector, are suitable.
  • the compounds of the invention are generally defined by the formula (I).
  • R 1 "preferably represents optionally substituted by fluorine, chlorine, bromine or iodine-substituted, straight-chain or branched alkynyl having 3 to 6 carbon atoms.
  • R 2 is preferably hydrogen, amino, fluorine, chlorine, bromine, iodine or fluorine- and / or chlorine-substituted, straight-chain or branched alkyl having 1 to 3 carbon atoms.
  • R 3 is preferably hydrogen, amino, fluorine, chlorine, bromine, iodine or optionally substituted by fluorine and / or chlorine, straight-chain or branched alkyl having 1 to 3 carbon atoms.
  • R 4 is preferably a monocyclic or bicyclic, optionally substituted by nitro, hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, each optionally substituted by hydroxy, cyano, fluoro, chloro or bromo Ci-C 5 alkyl, C t -CS-alkyl-carbonyl, Ci-C 5 alkoxy, Q-Cs-alkoxy-carbonyl, C r C 5 alkylthio, C r C 3 alkylsulfinyl, C r C 5 - Alkylsulfonyl ; Q-Cs-alkylamino, C 1 -C 5 - alkyl-aminocarbonyl, di- (Ci-C 5 alkyl) amino, di (C 1 -C 5 alkyl) amino-carbonyl or di- (Ci- C 5 alky
  • A is particularly preferably a single bond or O (oxygen), S (sulfur), NH, N (methyl) or methylene, ethane-1, l-diyl (ethylidene) or ethane-l, 2-diyl (dimethylene) ,
  • R 1 particularly preferably represents optionally substituted by fluorine, chlorine, bromine or iodine 2-propyn-1-yl, 2-butyn-1-yl, 3-butin-2-yl or 2-pentyne-1-yl.
  • R 2 particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl substituted by fluorine and / or chlorine.
  • R 3 particularly preferably represents hydrogen, fluorine, chlorine, bromine or optionally methyl substituted by fluorine and / or chlorine.
  • R 4 particularly preferably represents a monocyclic, optionally substituted by nitro, hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, in each case optionally substituted by hydroxy, cyano, fluorine or chlorine, methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl
  • R 1 most preferably represents 2-propyn-1-yl, 2-butyn-1-yl or 2-pentyne-1-yl.
  • R 2 very particularly preferably represents hydrogen.
  • R 3 very particularly preferably represents hydrogen, fluorine, chlorine or methyl.
  • R 4 very particularly preferably represents a monocyclic methyl, ethyl, n- or i-propyl optionally substituted by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, in each case by cyano, fluorine or chlorine.
  • the in the inventive process (a) for the preparation of the compounds of general formula (T) as starting materials to be used reactive pyrimidines are generally defined by the formula (H).
  • A, R 2 , R 3 and R 4 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of general formula (I) according to the invention as being preferred or particularly preferred for A R 2 , R 3 and R 4 have been given;
  • X 1 is preferably fluorine, chlorine, bromine, methylsulfonyl or ethylsulfonyl, in particular chlorine.
  • the starting materials of the general formula (H) are known and / or can be prepared by processes known per se (cf DE-4031798).
  • R 1 preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of general formula (I) according to the invention as being preferred or particularly preferred for R 1 .
  • the starting materials of formula (IH) are known organic synthetic chemicals.
  • the process according to the invention (b) for the preparation of the compounds of general formula (T) as starting materials to be used reactive pyrimidines are generally defined by the formula (TV).
  • R 1, R 2 and R 3 have preferably or in particular have those meanings which have as preferred or as particularly preferred above in connection with the description of the compounds of the general formula (I) for R 1, R 2 and R 3 have been given;
  • X 2 is preferably fluorine, chlorine, bromine, methylsulfonyl or ethylsulfonyl, in particular chlorine.
  • the starting materials of the formula (IV) are known and / or can be prepared by processes known per se (cf., WO-2002/024663).
  • a and R 4 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of general formula (I) according to the invention as being preferred or particularly preferred for A and R 4 have been.
  • reaction auxiliaries for carrying out the processes (a) and (b) according to the invention, it is possible to use all suitable inorganic or organic acid acceptors. These preferably include alkali metal and alkaline earth metal compounds and basic nitrogen compounds, in particular alkylamines.
  • alkali metal and alkaline earth metal compounds preferably include alkali metal and alkaline earth metal compounds and basic nitrogen compounds, in particular alkylamines.
  • alkylamines preferably include alkali metal and alkaline earth metal compounds and basic nitrogen compounds, in particular alkylamines.
  • hydrides, hydroxides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium, barium and cesium and further basic compounds such as amidiribases or guanidine bases such as 7-methyl-l, 5,7-triazabicyclo (4.4.
  • Lewis acids such as, for example, aluminum chloride, boric acid, boron trifluoride, trimethylstannane, zinc (II) -chloride, zinc (II) bromide, or compounds having similar properties can optionally also be used.
  • Suitable diluents for carrying out the processes (a) and (b) according to the invention are all solvents which are inert under the reaction conditions.
  • halogenated hydrocarbons especially chlorinated hydrocarbons such as tetrachlorethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene ; Alcohols such as methanol, ethanol, isopropanol, butanol; Ethers such as ethyl propyl ether, methyl tert-butyl ether, n-butyl ether, anisole, phenethol, cyclohexylmethyl ether, dimethyl ether, diethyl ether, dipropyl ether, diisoprop
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, one works at temperatures between -50 0 C and +150 0 C, preferably between -2O 0 C and +120 0 C.
  • the erf ⁇ ndungswashe process is generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally between 0.1 bar and 15 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction aid, optionally under a protective gas atmosphere (e.g., under nitrogen, argon or helium), and the reaction mixture is generally stirred for several hours at the required temperature.
  • a protective gas atmosphere e.g., under nitrogen, argon or helium
  • the active compounds of the formula (I) according to the invention are suitable for plant tolerance, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids and nematodes. which occur in agriculture, forests, gardens and recreational facilities, in supplies and materials, and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
  • Thysanoptera e.g. Herculothrips femoralis, Thrips tabaci, Thrips palmi, FranMiniella occidentalis.
  • Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
  • Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis Spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria me
  • Otiorrhynchus sulcatus 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.
  • Hymenoptera eg Diprion spp. From the order of Hymenoptera eg Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Diptera eg Aedes spp., Anopheles spp., Culex 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., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami
  • siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp.
  • arachnids e.g. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Pliyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.
  • Scorpio maurus Latrodectus mactans
  • Acarus siro Argas spp.
  • Ornithodoros spp. Dermanyssus gallinae
  • Eriophyes ribis Eriophyes ribis
  • Pliyllocoptruta oleivora Boophilus spp.
  • Boophilus spp. Rhipicephalus spp.
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
  • the plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
  • the compounds of the formula (I) according to the invention are distinguished in particular by a strong action against aphids, e.g. Aphis spp. and Myzus spp. out.
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides or as safeners for this purpose, or as microbicides, for example as fungicides, antimycotics or bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop 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 varieties which can or can not be protected by plant breeders' rights.
  • Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • Part of the crop also includes crops as well vegetative and generative growth material, for example cuttings, tubers, Rbizome, offshoots and seeds.
  • the erfmdungsconcee treatment of the plants and plant parts with the active ingredients is carried out directly or by affecting its environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, spreading, injecting and propagating material, in particular in seeds, further by single or multilayer coating.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, active substance-impregnated natural and synthetic substances and superfine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • 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.
  • Suitable solid carriers are:
  • ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules in question: eg broken and fractionated natural rocks such Calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks;
  • suitable emulsifiers and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates as well as protein hydrolysates; suitable
  • Adhesives such as carboxymethylcellulose, natural and synthetic powders, granules or latexes such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
  • Other additives may 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 zinc.
  • 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 zinc.
  • the formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
  • the active ingredient according to the invention can be present in its commercially available formulations as well as in the formulations prepared from these formulations in admixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematocides, fungicides, growth-regulating substances or herbicides.
  • active substances such as insecticides, attractants, sterilants, bactericides, acaricides, nematocides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric acid esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, microorganism-produced substances and the like.
  • Particularly favorable mixing partners are e.g. the following:
  • Copper salts and preparations such as Bordeaux mixture; Copper hydroxide; Copper naphthenates; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxides; mancopper; Oxine-copper.
  • Organotins for example azocyclotin, cyhexatin, fenbutatin oxides
  • METI's for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
  • Carboxamides for example flonicamide
  • Octopaminergic agonists for example Amitraz
  • Inhibitors of magnesium-stimulated ATPase for example propargite 20.
  • BDCAs for example N 2 - [l, l -dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N - [2-methyl-4- [l, 2,2,2-tetrafluoro-l- ( trifluoromethyl) ethyl] phenyl] -l, 2-benzenedicarboxamide (CAS Reg. No .: 272451-65-7)
  • Nereistoxin analogs for example thiocyclam hydrogen oxalate, thiosultap-sodium
  • the active compounds according to the invention can furthermore be employed as insecticides in their commercial formulations and in the forms of use prepared from these formulations in mixture with synergists.
  • Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
  • the active compounds according to the invention can furthermore, when used as insecticides, be present in their commercial formulations and in the forms of use prepared from these formulations in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
  • the application is done in a custom forms adapted to the application.
  • the active ingredient When used against hygiene and storage pests, the active ingredient is characterized by an excellent residual effect on wood and clay and by a good alkali stability on limed substrates.
  • plants and their parts can be treated.
  • wild-type or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the term "parts” or “parts of plants” or “plant parts” has been explained above.
  • Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
  • the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to Dryness or against water or soil salt content, increased flowering power, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects ,
  • transgenic genetically engineered
  • Plants or plant varieties include all plants that received genetic material through the genetic modification, which these plants particularly advantageous valuable
  • transgenic plants are the important crops, such as cereals (wheat, rice), corn, soy, potato,
  • Grapes with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape. As properties ("Traits”) are particularly emphasized the increased
  • Toxins produced by plants in particular those produced by the genetic material from Bacillus
  • Thuringiensis e.g., by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CrylEA, CryIIIB2,
  • SAR systemin
  • phytoalexins elicitors
  • resistance genes elicitors
  • resistance genes elicitors
  • resistance genes elicitors
  • resistance genes elicitors
  • resistance genes elicitors
  • resistance genes elicitors
  • resistance genes elicitors
  • resistance genes elicitors
  • resistance genes elicitors
  • resistance genes elicitors
  • resistance genes e.g., phosphinotricin (e.g.
  • herbicide-tolerant plants are sold. Examples of herbicide-tolerant plants are maize varieties,
  • Herbicide-resistant plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.
  • the plants listed can be treated particularly advantageously erf ⁇ ndungshack with the compounds of the general formula I or the active substance mixtures according to the invention.
  • the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants.
  • Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
  • the active compounds of the invention not only 'against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ectoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair pieces , Featherlings and fleas.
  • animal parasites ectoparasites
  • ticks such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair pieces , Featherlings and fleas.
  • These parasites include:
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
  • Nematocerina and Brachycerina e.g. Aedes i., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia i., 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., Glossina spp., Chrysomyia spppp
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, miscellaneous animals such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such.
  • farm animals such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, miscellaneous animals such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such.
  • enteral administration in the form of, for example, tablets, capsules, infusions, Drenchen, granules, pastes, BoIi, the feed-through process, suppositories
  • parenteral administration such as by Injections (intramuscular, subcutaneous
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • the compounds according to the invention exhibit a high insecticidal activity against insects which destroy industrial materials.
  • insects By way of example and preferably without limiting however, the following insects are mentioned:
  • Hymenoptera such as Sirex juvencus, Urocem's gigas, Urocerus gigas taignus, Urocerus augur;
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
  • Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally Dyes and pigments and other processing aids.
  • the insecticidal agents or concentrates used for the protection of wood and Hcreerkstoffen contain the active ingredient according to the invention in a concentration of 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.
  • the amount of agents or concentrates used depends on the nature and occurrence of the insects and on the medium.
  • the optimal amount used 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 ingredient, based on the material to be protected.
  • the solvent and / or diluent used is an organic-chemical solvent or solvent mixture and / or an oily or oily high-volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.
  • Organic chemical solvents which are preferably oily or oil-like ⁇ Lösurigsstoff having an evaporation number above 35 and a flashpoint above 3O 0 C, preferably above 45 ° v C, "inserted.
  • a low-volatile, water-insoluble, oily and oil-type solvents are appropriate mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene used.
  • Mineral oils having a boiling range of 170 to 220 0 C, white spirit having a boiling range of 170 to 22O 0 C, spindle oil with a boiling range of 250 to 350 0 C, petroleum and aromatics with a boiling range of 160 to 280 0 C, oil of turpentine and Like. For use.
  • the organic semi-volatile oily or oily solvents having an evaporation number above 35 and a flash point above 30 0 C, preferably above 45 0 C, can be partially replaced by light or medium volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 0 C, preferably above 45 ° C, and that the insecticide-fungicide mixture in this solvent mixture is soluble or emulsifiable.
  • a part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture replaced.
  • aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups are used, for example glycol ethers, esters or the like.
  • organic-chemical binders are the water-dilutable and / or soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils used in the organic-chemical solvents used, in particular binders consisting of or containing an acrylate resin, a vinyl resin, eg Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene cumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.
  • binders consisting of or containing an acrylate resin, a vinyl resin, eg Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene cumarone resin, silicone resin
  • the synthetic resin used as the binder may 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 repellents, odor correctors and inhibitors or corrosion scavengers and the like can be used.
  • Vt is according to the invention as organic-chemical binder at least one alkyd resin or modified alkyd resin and / or a drying vegetable oil in the middle or in the concentrate.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • the mentioned binder can be completely or partially replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. Preferably, they replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers are derived from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric 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, glycerol ethers or higher molecular weight glyco-ethers, glycerol esters and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric esters such as tributyl phosphate
  • adipic acid esters such as di (2-ethylhexyl) adipate
  • stearates such as butyl
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Particularly suitable solvents or diluents are also water, optionally in admixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved by large-scale impregnation, eg vacuum, double vacuum or printing process.
  • the ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
  • Particularly preferred admixing partners may be insecticides such as chlorpyriphos, phoxim, silafluofm, alphamethrin, cyfluthrin, cypermethrin, deltarnethrine, permethrih, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozide, triflumuron, clothianidin, spinosad, tefluthrin,
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluid, tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N octylisothiazolin-3-one. n.
  • the compounds according to the invention can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, wharfages and signal systems, which come into contact with seawater or brackish water.
  • sessile oligochaetes such as calcareous owls, as well as mussels and species of the group Ledamorpha (barnacles), such as various Lepas and scalpel species, or species of the group Balanomorpha (barnacles), such as Baianus or Pollicipes species, increases the frictional resistance of As a result of increased energy consumption and, moreover, frequent drydocking periods, the operating costs are significantly increased.
  • group Ledamorpha such as various Lepas and scalpel species
  • Balanomorpha such as Baianus or Pollicipes species
  • Ectocarpus sp. and Ceramium sp. is particularly the fouling by sessile Entomostraken groups, which are summarized under the name Cirripedia (cirripeds), particular importance.
  • heavy metals such as, for example, bis (trialkyltin) sulfides, tri-7-yl-tin tin laurate, tri-w-butyltin chloride, copper (I) oxide, triethyltin chloride, Tri-rc-butyl (2- phenyl-4-chlorophenoxy) -tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, manganese ethylene bis-carbamate, zinc dimethyldithiocarbamate, zinc ethylene bis-thiocarbamate, zinc and copper salts of 2-pyridinethiol-1 oxide, bisdimethyldithiocarbamoylzinc ethylene bis-thiocarbamate, zinc oxide, copper (I)
  • the ready-to-use antifouling paints may optionally contain other active substances, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Algicides such as 2- / tert-butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzothiazuron, oxyfiuorfen, quinoclamine and terbutryn;
  • Fungicides such as benzo [ ⁇ ] thiophenecarboxylic cyclohexylamide S, S-dioxide, dichlofluanid, fluoro folpet, 3- ⁇ d-2-propynyl-butylcarbamate, tolylfluanid and azoles such as azaconazoles, cyproconazoles, epoxyconazole'j hexaconazoles, metconazoles, propiconazoles and tebuconazoles;
  • Molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb, Fe-chelates,
  • antifouling agents such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol-1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2 , 4,6-Trichlorphenylmaleinimid.
  • the antifouling agents used contain the erf ⁇ ndungswen active ingredient of the compounds of the invention in a concentration of 0.001 to 50 wt .-%, in particular from 0.01 to 20 wt .-%.
  • the antifouling agents of the invention further contain the usual ingredients, e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • Antifouling paints contain, in addition to the algicidal, fungicidal, molluscicidal and insecticidal active compounds according to the invention, in particular binders.
  • binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resin 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, drying oils, such as linseed oil, rosin esters or modified hard resins in combination with tar or bitumens, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins. , ,
  • paints also contain inorganic pigments, organic pigments or dyes which are preferably insoluble in seawater.
  • paints may contain materials such as rosin to allow for controlled release of the active ingredients.
  • the paints may further contain plasticizers, rheology modifiers, and other conventional ingredients. Also in self-polishing antifouling systems, the compounds of the invention or the above-mentioned mixtures can be incorporated.
  • the active compounds are also suitable for controlling animal pests, in particular of and mites, which occur in enclosed spaces, such as, for example, offices, vehicle cabins and the like. She. can fight these pests are used alone or in combination with other agents and excipients in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • 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, neonicotinoids, growth regulators or active compounds from other known classes of insecticides. It is used in aerosols, pressureless sprays, eg pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in straw baits or bait stations.
  • suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, neonicotinoids, growth regulators or active compounds from other known classes of insecticides. It is used in aerosols, pressureless sprays, eg pump and atomizer sprays, fog machines,
  • the mixture is partitioned between saturated ammonium chloride solution and methyl t-butyl ether, the organic phase is dried, concentrated under reduced pressure and further purified by column chromatography (silica gel RP-18, gradient acetonitrile-water).
  • the lambda-max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis), which are infested by all stages of the green pepper aphid (Myzus persicae), are sprayed with an active compound preparation of the desired concentration.
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Cotton leaves which are heavily infested with the cotton aphid (Aphis gossypii) 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.
  • Vessels are filled with all stages of the Green Peach aphid (Myzus persicae), by sucking on the preparation of active compound of the desired concentration is treated.
  • Green Peach aphid Myzus persicae
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • the active compound is mixed with the indicated amounts of solvent and the concentrate is diluted with stained water to the desired concentration.
  • the Myzus persicae is an active compound preparation of the desired concentration for. Recording provided.
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.

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Abstract

The invention relates to compounds of formula (i), wherein A, R1, R2, R3 and R4 have a significance given in the description, to methods, intermediate products and to the use thereof in pest control.

Description

ALKINYLOXYPYRIMIDINE ALS PESTIZIDE ALKINYLOXYPYRIMIDINE AS PESTICIDES
Die vorliegende Anmeldung betrifft neue substituierte Pyrrolidine, Verfahren zu ihrer Herstellung und ihre Verwendung in Mitteln zur Bekämpfung von tierischen Schädlingen, vor allem von Arthropoden, insbesondere von Insekten.The present application relates to novel substituted pyrrolidines, processes for their preparation and their use in agents for combating animal pests, especially arthropods, in particular insects.
Bestimmte substituierte Pyrimidine sind bereits als potentielle Insektizide bekannt geworden (vgl. WO-2002/024663, WO-2003/076415, WO-2004/085407, WO-2004/099160), haben jedoch aufgrund einer nicht immer zufriedenstellenden Wirkung bislang keine Bedeutung erlangt.Certain substituted pyrimidines have already become known as potential insecticides (see WO-2002/024663, WO-2003/076415, WO-2004/085407, WO-2004/099160), but have so far not gained importance due to a not always satisfactory effect ,
Bestimmte 4-Pyridyl-pyrimidine sind bereits als potentielle Fungizide bekannt geworden (vgl. DE- 4031798). Über eine Wirksamkeit dieser Verbindungen gegen tierische Schädlinge ist jedoch bisher nichts bekannt geworden.Certain 4-pyridyl-pyrimidines have already become known as potential fungicides (cf DE-4031798). However, as yet, nothing has become known about the effectiveness of these compounds against animal pests.
Es wurden nun neue substituierte Pyrimidine der Formel (I) gefunden,New substituted pyrimidines of the formula (I) have now been found
in welcherin which
A für eine Einfachbindung oder für O (Sauerstoff), S (Schwefel), NH, N(C1-C4-AIlCyI), eineA is a single bond or O (oxygen), S (sulfur), NH, N (C 1 -C 4 -alkyl), a
Carbonyl-Gruppierung (C=O) oder eine Oxyimino-gruppierung (C=N-O-R, wobei R für Wasserstoff oder Ci-C4-Alkyl steht) oder für gegebenenfalls durch Hydroxy oder Halogen substituiertes, geradkettiges oder verzweigtes Alkandiyl mit 1 bis 4 Kohlenstoffatomen steht,Carbonyl grouping (C = O) or an oxyimino group (C = NOR, wherein R is hydrogen or Ci-C 4 alkyl) or optionally substituted by hydroxy or halogen, straight or branched alkanediyl having 1 to 4 carbon atoms .
R1 für gegebenenfalls durch Halogen substituiertes, geradkettiges oder verzweigtes Alkinyl mit 2 bis 10 Kohlenstoffatomen steht,R 1 represents optionally halogen-substituted, straight-chain or branched alkynyl having 2 to 10 carbon atoms,
R2 für Wasserstoff, Amino, Halogen oder durch Halogen substituiertes, geradkettiges oder verzweigtes Alkyl mit 1 bis 4 Kohlenstoffatomen steht,R 2 is hydrogen, amino, halogen or halogen-substituted, straight-chain or branched alkyl having 1 to 4 carbon atoms,
R3 für Wasserstoff, Amino, Halogen oder gegebenenfalls durch Halogen substituiertes, geradkettiges oder verzweigtes Alkyl mit 1 bis 4 Kohlenstoffatomen steht, undR 3 represents hydrogen, amino, halogen or optionally halogen-substituted, straight-chain or branched alkyl having 1 to 4 carbon atoms, and
R4 für eine monocyclische oder bicyclische, gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, durch jeweils gegebenen- falls durch Hydroxy, Cyano oder Halogen substituiertes Ci-C6-Alkyl, Ci-C6-Alkyl- carbonyl, CrC6-Alkoxy5 d-Cß-Alkoxy-carbonyl, CrC6-Alkylthio, CrC6-Alkylsulfinyl, Q-Cs-Alkylsulfonyl, CrC6-Alkylamino, Ci-Ce-Alkyl-aminocarbonyl, Di-(Ci -C6-Alkyl)- amino, Di-(CrC6-Alkyl)-amino-carbonyl oder substituierte heteroaromatische Gruppierung mit bis zu 9 Kohlenstoffatomen und mindestens einem Heteroatom aus der Reihe N (Stickstoff, 1 bis 5 N-Atome), O (Sauerstoff, maximal 1 O-Atom), S (Schwefel, maximal 1 S-Atom) steht.R 4 is a monocyclic or bicyclic radical, optionally substituted by nitro, hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, by any given substituted by hydroxy, cyano or halogen substituted Ci-C 6 alkyl, Ci-C 6 alkyl carbonyl, C r C 6 alkoxy d-5 CSS-alkoxy-carbonyl, C r C 6 alkylthio, C r C 6 alkylsulfinyl, Q-Cs-alkylsulfonyl, C r C6-alkylamino, Ci-Ce-alkyl-aminocarbonyl, di- (Ci -C 6 alkyl) - amino, di (C r C 6 alkyl) amino-carbonyl or substituted heteroaromatic group having up to 9 carbon atoms and at least one heteroatom from the series N (nitrogen, 1 to 5 N atoms), O (oxygen, at most 1 O atom), S (sulfur, at most 1 S atom).
Weiter wurde gefunden, dass man die neuen substituierte Pyrimidine der Formel (I) erhält, wenn manIt has furthermore been found that the novel substituted pyrimidines of the formula (I) are obtained when
(a) reaktive Pyrimidine der Formel (H)(a) reactive pyrimidines of the formula (H)
in welcherin which
A, R2, R3 und R4 die oben angegebenen Bedeutungen haben undA, R 2 , R 3 and R 4 have the meanings given above and
X1 für Halogen oder Ci-C4-Alkylsulfonyl steht,X 1 is halogen or C 1 -C 4 -alkylsulfonyl,
mit Alkinolen der Formel (JH)with alkynols of the formula (JH)
(m)(M)
in welcherin which
R1 die oben angegebene Bedeutung hat,R 1 has the meaning given above,
- oder mit Alkalimetallsalzen hiervon -or with alkali metal salts thereof -
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt,if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,
oder wenn manor if you are
(b) reaktive Pyrimidine der Formel (IV) (b) reactive pyrimidines of the formula (IV)
in welcherin which
R1, R2 und R3 die oben angegebenen Bedeutungen haben undR 1 , R 2 and R 3 have the meanings given above and
X2 für Halogen oder CrC^Alkylsulfonyl steht,X 2 is halogen or C 1 -C 4 -alkylsulfonyl,
mit nucleophilen Verbindungen der Formel (V)with nucleophilic compounds of the formula (V)
A (V) A (V)
in welcherin which
A und R4 die oben angegebenen Bedeutungen habenA and R 4 have the meanings given above
- oder mit Alkalimetallsalzen hiervon -or with alkali metal salts thereof -
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt.if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents.
Schließlich wurde gefunden, dass die neuen Verbindungen der Formel (I) stark ausgeprägte biologische Eigenschaften haben und vor allem zur Bekämpfung von tierischen Schädlingen, insbesondere von Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in den Forsten, im Vorrats- und Materialschutz sowie im Hygienebereich vorkommen, geeignet sind.Finally, it has been found that the novel compounds of the formula (I) have pronounced biological properties and, in particular, for controlling animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forestry, in the protection of stored products and materials, and in the hygiene sector, are suitable.
Die erfindungsgemäßen Verbindungen sind durch die Formel (I) allgemein definiert.The compounds of the invention are generally defined by the formula (I).
Bevorzugte Substituenten bzw. Bereiche der in den oben und nachstehend aufgeführten Formeln vorkommenden Reste werden im Folgenden erläutert.Preferred substituents or ranges of the radicals occurring in the formulas listed above and below are explained below.
A steht bevorzugt für eine Einfachbindung oder für O (Sauerstoff), S (Schwefel), NH, N(Methyl), N(Ethyl), N(Propyl), eine Carbonyl-Gruppierung (C=O) oder eine Oxyimino- gruppierung (C=N-O-R, wobei R für Wasserstoff, Methyl oder Ethyl steht) oder für gegebenenfalls durch Hydroxy, Fluor oder Chlor substituiertes, geradkettiges oder verzweigtes Alkandiyl mit 1 bis 3 Kohlenstoffatomen. R1 steht "bevorzugt für gegebenenfalls durch Fluor, Chlor, Brom oder Iod substituiertes, geradkettiges oder verzweigtes Alkinyl mit 3 bis 6 Kohlenstoffatomen.A preferably represents a single bond or represents O (oxygen), S (sulfur), NH, N (methyl), N (ethyl), N (propyl), a carbonyl group (C =O) or an oxyimino group ( C = NOR, where R is hydrogen, methyl or ethyl) or optionally hydroxy-, fluorine- or chlorine-substituted, straight-chain or branched alkanediyl having 1 to 3 carbon atoms. R 1 "preferably represents optionally substituted by fluorine, chlorine, bromine or iodine-substituted, straight-chain or branched alkynyl having 3 to 6 carbon atoms.
R2 steht bevorzugt für Wasserstoff, Amino, Fluor, Chlor, Brom, Iod oder durch Fluor und/oder Chlor substituiertes, geradkettiges oder verzweigtes Alkyl mit 1 bis 3 Kohlenstoffatomen.R 2 is preferably hydrogen, amino, fluorine, chlorine, bromine, iodine or fluorine- and / or chlorine-substituted, straight-chain or branched alkyl having 1 to 3 carbon atoms.
R3 steht bevorzugt für Wasserstoff, Amino, Fluor, Chlor, Brom, Iod oder gegebenenfalls durch Fluor und/oder Chlor substituiertes, geradkettiges oder verzweigtes Alkyl mit 1 bis 3 Kohlenstoffatomen.R 3 is preferably hydrogen, amino, fluorine, chlorine, bromine, iodine or optionally substituted by fluorine and / or chlorine, straight-chain or branched alkyl having 1 to 3 carbon atoms.
R4 steht bevorzugt für eine monocyclische oder bicyclische, gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Iod, durch jeweils gegebenenfalls durch Hydroxy, Cyano, Fluor, Chlor oder Brom substituiertes Ci-C5-Alkyl, Ct-Cs-Alkyl-carbonyl, Ci-C5-Alkoxy, Q-Cs-Alkoxy-carbonyl, CrC5-Alkylthio, CrC3-Alkylsulfinyl, CrC5-Alkylsulfonyl; Q-Cs-Alkylamino, C1-C5- Alkyl-aminocarbonyl, Di-(Ci-C5-Alkyl)-amino, Di-(C1-C5-Alkyl)-amino-carbonyl oder Di- (Ci-C5-Alkyl)-amino-sulfonyl substituierte heteroaromatische Gruppierung mit bis zu 9 Kohlenstoffatomen und mindestens einem Heteroatom aus der Reihe N (Stickstoff, 1 bis 5 N-Atome), O (Sauerstoff, maximal 1 O-Atom), S (Schwefel, maximal 1 S-Atom).R 4 is preferably a monocyclic or bicyclic, optionally substituted by nitro, hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, each optionally substituted by hydroxy, cyano, fluoro, chloro or bromo Ci-C 5 alkyl, C t -CS-alkyl-carbonyl, Ci-C 5 alkoxy, Q-Cs-alkoxy-carbonyl, C r C 5 alkylthio, C r C 3 alkylsulfinyl, C r C 5 - Alkylsulfonyl ; Q-Cs-alkylamino, C 1 -C 5 - alkyl-aminocarbonyl, di- (Ci-C 5 alkyl) amino, di (C 1 -C 5 alkyl) amino-carbonyl or di- (Ci- C 5 alkyl) -amino-sulfonyl-substituted heteroaromatic grouping having up to 9 carbon atoms and at least one heteroatom from the series N (nitrogen, 1 to 5 N atoms), O (oxygen, at most 1 O atom), S (sulfur , maximum 1 S atom).
A steht besonders bevorzugt für eine Einfachbindung oder für O (Sauerstoff), S (Schwefel), NH, N(Methyl) oder für Methylen, Ethan-l,l-diyl (Ethyliden) oder Ethan-l,2-diyl (Dimethylen).A is particularly preferably a single bond or O (oxygen), S (sulfur), NH, N (methyl) or methylene, ethane-1, l-diyl (ethylidene) or ethane-l, 2-diyl (dimethylene) ,
R1 steht besonders bevorzugt für gegebenenfalls durch Fluor, Chlor, Brom oder Iod substituiertes 2-Propin-l-yl, 2-Butin-l-yl, 3-Butin-2-yl oder 2-Pentin-l-yl.R 1 particularly preferably represents optionally substituted by fluorine, chlorine, bromine or iodine 2-propyn-1-yl, 2-butyn-1-yl, 3-butin-2-yl or 2-pentyne-1-yl.
R2 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder durch Fluor und/oder Chlor substituiertes Methyl.R 2 particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl substituted by fluorine and / or chlorine.
R3 steht besonders bevorzugt für Wasserstoff, Fluor, Chlor, Brom oder gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl.R 3 particularly preferably represents hydrogen, fluorine, chlorine, bromine or optionally methyl substituted by fluorine and / or chlorine.
R4 steht besonders bevorzugt für eine monocyclische, gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Iod, durch jeweils gegebenenfalls durch Hydroxy, Cyano, Fluor oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Acetyl, Propionyl, n- oder i- Butyroyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, n-, i-, s- oder t-Butoxycarbonyl, Methylthio, Ethylthio, n- oder i- Propylthio, Methylsulfϊnyl, Ethylsulfmyl, Methylsulfonyl, Ethylsulfonyl, Methylamino, Ethylaπώio, n- oder i-Propylamino, n-, i-, s- oder t-Butylamino, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethylamino, Diethylamino, Dimethylamino carbonyl, Diethylaminocarbonyl, Dimethylaminosulfonyl oder Diethylaminosulfonyl substituierte heteroaromatische Gruppierung aus der Reihe Furyl, Thienyl, Pyrrolyl, Pyrazolyl, rmidazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Triazolyl, Pyridinyl, Pyrimidinyl, Pyrazinyl, Pyridazinyl, Triazinyl.R 4 particularly preferably represents a monocyclic, optionally substituted by nitro, hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, in each case optionally substituted by hydroxy, cyano, fluorine or chlorine, methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, methylamino, Ethylaπώio, n- or i-propylamino, n-, i-, s- or t-butylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylamino carbonyl, diethylaminocarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl-substituted heteroaromatic grouping of the Row furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl.
A steht ganz besonders bevorzugt für eine Einfachbindung oder für O (Sauerstoff), S (Schwefel), NH, N(Methyl) oder Methylen.A very particularly preferably represents a single bond or O (oxygen), S (sulfur), NH, N (methyl) or methylene.
R1 steht ganz besonders bevorzugt für 2-Propin-l-yl, 2-Butin-l-yl oder 2-Pentin-l-yl.R 1 most preferably represents 2-propyn-1-yl, 2-butyn-1-yl or 2-pentyne-1-yl.
R2 steht ganz besonders bevorzugt für Wasserstoff.R 2 very particularly preferably represents hydrogen.
R3 steht ganz besonders bevorzugt für Wasserstoff, Fluor, Chlor oder Methyl.R 3 very particularly preferably represents hydrogen, fluorine, chlorine or methyl.
R4 steht ganz besonders bevorzugt für eine monocyclische gegebenenfalls durch Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, durch jeweils gegebenenfalls durch Cyano, Fluor oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxy, Ethoxy, n- oder i- Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfmyl, Methylsulfonyl, Ethylsulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethylamino, Diethylamino, Di- methylaminocarbonyl oder Dimethylaminosulfonyl substituierte heteroaromatische Gruppierung aus der Reihe Furyl, Thienyl, Pyrrolyl, Pyrazolyl, Imidazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Triazolyl, Pyridinyl, Pyrimidinyl, Pyrazinyl, Pyridazinyl, Triazinyl.R 4 very particularly preferably represents a monocyclic methyl, ethyl, n- or i-propyl optionally substituted by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, in each case by cyano, fluorine or chlorine. , i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl or dimethylaminosulfonyl-substituted heteroaromatic grouping from the series Furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl.
Erfindungsgemäß bevorzugt werden die Verbindungen der Formel (I), bei welchen die Kombinationen der vorstehend als bevorzugt aufgeführten Bedeutungen vorliegen.Preference according to the invention is given to the compounds of the formula (I) in which the combinations of the meanings listed above are preferred.
Erfindungsgemäß besonders bevorzugt werden die Verbindungen der Formel (I), bei welchen die Kombinationen der vorstehend als besonders bevorzugt aufgeführten Bedeutungen vorliegen.Particular preference is given in accordance with the invention to the compounds of the formula (I) in which the combinations of the meanings listed above as being particularly preferred are present.
Erfϊndungsgemäß ganz besonders bevorzugt werden die Verbindungen der Formel (I), bei welchen die Kombinationen der vorstehend als ganz besonders bevorzugt aufgeführten Bedeutungen vorliegen. In den oben und nachstehend aufgeführten Restedefinitionen sind Kohlenwasserstoffreste, wie Alkyl oder Alkinyl - auch in Verbindung mit Heteroatomen wie Alkoxy oder Alkinyloxy - soweit möglich jeweils geradkettig oder verzweigt.Very particular preference according to the invention is given to the compounds of the formula (I) in which the combinations of the meanings listed above as being very particularly preferred are present. In the radical definitions given above and below, hydrocarbon radicals, such as alkyl or alkynyl - also in combination with heteroatoms such as alkoxy or alkynyloxy - are each, if possible, straight-chain or branched.
Verwendet man beispielsweise 4-Chlor-5-fluor-6-(pyrazol-l-yl)-pyrimidin und 2-Propin-l-ol als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Herstellungsverfahren (a) durch das folgende Formelschema skizziert werden:If, for example, 4-chloro-5-fluoro-6- (pyrazol-1-yl) -pyrimidine and 2-propyn-1-ol are used as starting materials, the course of the reaction in preparation process (a) according to the invention can be outlined by the following formula scheme:
Verwendet man beispielsweise 4-Fluor-6-(2-butin-l-yl-oxy)-pyrimidin und hnidazol als Ausgangsstoffe, so kann der Reaktionsablauf beim erfindungsgemäßen Herstellungsverfahren (b) durch das folgende Formelschema skizziert werden:If, for example, 4-fluoro-6- (2-butyn-1-yl-oxy) -pyrimidine and hidazole are used as starting materials, the course of the reaction in the preparation process (b) according to the invention can be outlined by the following formula scheme:
Die beim erfϊndungsgemäßen Verfahren (a) zur Herstellung der Verbindungen der allgemeinen Formel (T) als Ausgangsstoffe zu verwendenden reaktiven Pyrimidine sind durch die Formel (H) allgemein definiert. In der Formel (II) haben A, R2, R3 und R4 vorzugsweise bzw. insbesondere diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfϊndungsgemäßen Verbindungen der allgemeinen Formel (I) als bevorzugt bzw. als besonders bevorzugt für A, R2, R3 und R4 angegeben worden sind; X1 steht vorzugsweise für Fluor, Chlor, Brom, Methylsulfonyl oder Ethylsulfonyl, insbesondere für Chlor.The in the inventive process (a) for the preparation of the compounds of general formula (T) as starting materials to be used reactive pyrimidines are generally defined by the formula (H). In the formula (II), A, R 2 , R 3 and R 4 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of general formula (I) according to the invention as being preferred or particularly preferred for A R 2 , R 3 and R 4 have been given; X 1 is preferably fluorine, chlorine, bromine, methylsulfonyl or ethylsulfonyl, in particular chlorine.
Die Ausgangsstoffe der allgemeinen Formel (H) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. DE-4031798).The starting materials of the general formula (H) are known and / or can be prepared by processes known per se (cf DE-4031798).
Die beim erfϊndungsgemäßen Verfahren (a) zur Herstellung der Verbindungen der allgemeinen Formel (I) weiter als Ausgangsstoffe zu verwendenden Alkinole sind durch die Formel (TS) allgemein definiert. In der Formel (IH) hat R1 vorzugsweise bzw. insbesondere diejenige Bedeutung, die bereits oben im Zusammenhang mit der Beschreibung der erfϊndungsgemäßen Verbindungen der allgemeinen Formel (I) als bevorzugt bzw. als besonders bevorzugt für R1 angegeben worden ist.The in the inventive process (a) for the preparation of the compounds of general formula (I) as starting materials to be used alkynols are generally defined by the formula (TS). In the formula (IH), R 1 preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of general formula (I) according to the invention as being preferred or particularly preferred for R 1 .
Die Ausgangsstoffe der Formel (IH) sind bekannte organische Synthesechemikalien. Die beim erfrndungsgemäßen Verfahren (b) zur Herstellung der Verbindungen der allgemeinen Formel (T) als Ausgangsstoffe zu verwendenden reaktiven Pyrimidine sind durch die Formel (TV) allgemein definiert. In der Formel (IV) haben R1, R2 und R3 vorzugsweise bzw. insbesondere diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) als bevorzugt bzw. als besonders bevorzugt für R1, R2 und R3 angegeben worden sind; X2 steht vorzugsweise für Fluor, Chlor, Brom, Methylsulfonyl oder Ethylsulfonyl, insbesondere für Chlor.The starting materials of formula (IH) are known organic synthetic chemicals. The process according to the invention (b) for the preparation of the compounds of general formula (T) as starting materials to be used reactive pyrimidines are generally defined by the formula (TV). In the formula (IV) R 1, R 2 and R 3 have preferably or in particular have those meanings which have as preferred or as particularly preferred above in connection with the description of the compounds of the general formula (I) for R 1, R 2 and R 3 have been given; X 2 is preferably fluorine, chlorine, bromine, methylsulfonyl or ethylsulfonyl, in particular chlorine.
Die Ausgangsstoffe der Formel (IV) sind bekannt und/oder können nach an sich bekannten Verfahren hergestellt werden (vgl. WO-2002/024663).The starting materials of the formula (IV) are known and / or can be prepared by processes known per se (cf., WO-2002/024663).
Die beim erfindungsgemäßen Verfahren (b) zur Herstellung der Verbindungen der allgemeinen Formel (I) weiter als Ausgangsstoffe zu verwendenden nucleophilen Verbindungen sind durch die Formel (V) allgemein definiert. In der Formel (V) haben A und R4 vorzugsweise bzw. insbesondere diejenigen Bedeutungen, die bereits oben im Zusammenhang mit der Beschreibung der er- fϊndungsgemäßen Verbindungen der allgemeinen Formel (I) als bevorzugt bzw. als besonders bevorzugt für A und R4 angegeben worden sind.The in process (b) for the preparation of the compounds of general formula (I) as starting materials to be used nucleophilic compounds are generally defined by the formula (V). In the formula (V), A and R 4 preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of general formula (I) according to the invention as being preferred or particularly preferred for A and R 4 have been.
Die erfindungsgemäßen Verfahren (a) und (b) zur Herstellung der Verbindungen der Formel (I) werden vorzugsweise unter Verwendung mehrerer Reaktionshilfmittel durchgeführt. Als Reaktionshilfsmittel zur Durchführung der erfindungsgemäßen Verfahren (a) und (b) können alle geeigneten anorganischen oder organischen Säureakzeptoren eingesetzt werden. Hierzu gehören vorzugsweise Alkalimetall- und Erdalkalimetallverbindungen sowie basische Stickstoffverbindungen, insbesondere Alkylamine. Beispielhaft seien dafür erwähnt die Hydride, Hydroxide, Oxide und Carbonate des Lithiums, Natriums, Kaliums, Magnesiums, Calciums, Bariums und Cäsiums, ferner weitere basische Verbindungen wie Amidiribasen oder Guanidinbasen wie 7- Methyl-l,5,7-triazabicyclo(4.4.0)-dec-5-en (MTBD), Diazabicyclo(4.3.0)nonen (DBN), Diazabi- cyclo(2.2.2)octan (DABCO), l,8-Diaza-bicyclo(5.4.0)undecen (DBU), Cyclohexyl-tetrabutyl- guanidin (CyTBG), Cyclohexyltetramethylguanidin (CyTMG), N,N,N,N-Tetramethyl-1,8- naphthalindiamin, Pentamethylpiperidin, tertiäre Amine wie Triethylamin, Trimethylamin, N- Ethyl-diisopropylamin, Tribenzylamin, Triisobutylamin, Tributylamin, Tribenzylamin, N,N-Dime- thyl-cyclohexylamin, N-Ethyl-dicyclohexylamin, Triamylamin, Trihexylamin, N,N-Dimethyl- anilin, N,N-Dimethyl-toluidin, N,N-Dimethyl-p-aminopyridin, N-Methyl-pyrrolidin, N-Methyl- piperidin, N-Methyl-imidazol, N-Methyl-pyrrol, N-Methyl-morpholin, N-Methyl-hexamethylen- imin, Pyridin, 4-Pyrrolidino-pyridin, 4-Dimethylamino-pyridin, Chinolin, α-Picolin, ß-Picolin, Isochinolin, Pyrimidin, Acridin, N,N,N',N'-Tetramethylendiamin, N,N,N',N'-Tetraethylendiamin, Chinoxalin, N-Propyl-diisopropylamin, N-Ethyl-diisopropylamin, NjN'-Dimethyl-cyclohexylamin, 2,6-Lutidin, 2,4-Lutidin oder Triethylendiamin. Als Reaktionshilfsmittel können gegebenenfalls auch sogenannte Lewis-Säuren, wie z.B. Aluminiumchlorid, Borsäure, Bortrifluorid, Trimethylstannan, Zink(]I)-αhlorid, Zink(II)-bromid, oder Verbindungen mit ähnlichen Eigenschaften eingesetzt werden.The processes (a) and (b) according to the invention for the preparation of the compounds of the formula (I) are preferably carried out using a plurality of reaction auxiliaries. As reaction auxiliaries for carrying out the processes (a) and (b) according to the invention, it is possible to use all suitable inorganic or organic acid acceptors. These preferably include alkali metal and alkaline earth metal compounds and basic nitrogen compounds, in particular alkylamines. By way of example, mention may be made of the hydrides, hydroxides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium, barium and cesium, and further basic compounds such as amidiribases or guanidine bases such as 7-methyl-l, 5,7-triazabicyclo (4.4. 0) -dec-5-ene (MTBD), diazabicyclo (4.3.0) nonene (DBN), diazabicyclo- (2.2.2) octane (DABCO), l, 8-diazabicyclo (5.4.0) undecene ( DBU), cyclohexyltetrabutylguanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), N, N, N, N-tetramethyl-1,8-naphthalenediamine, pentamethylpiperidine, tertiary amines such as triethylamine, trimethylamine, N-ethyl-diisopropylamine, tribenzylamine, Triisobutylamine, tributylamine, tribenzylamine, N, N-dimethylcyclohexylamine, N-ethyl-dicyclohexylamine, triamylamine, trihexylamine, N, N-dimethylaniline, N, N-dimethyl-toluidine, N, N-dimethyl-p- aminopyridine, N-methyl-pyrrolidine, N-methyl-piperidine, N-methyl-imidazole, N-methyl-pyrrole, N-methyl-morpholine, N-methyl-hexamethylene-imine, pyridine, 4-pyrrolidino-pyridine, 4- Dimeth ylamino-pyridine, quinoline, α-picoline, β-picoline, isoquinoline, pyrimidine, acridine, N, N, N ', N'-tetramethylenediamine, N, N, N', N'-tetraethylenediamine, quinoxaline, N-propyl diisopropylamine, N-ethyl-diisopropylamine, N j N'-dimethyl-cyclohexylamine, 2,6-lutidine, 2,4-lutidine or triethylenediamine. As reaction auxiliaries, so-called Lewis acids, such as, for example, aluminum chloride, boric acid, boron trifluoride, trimethylstannane, zinc (II) -chloride, zinc (II) bromide, or compounds having similar properties can optionally also be used.
Die erfindungsgemäßen Verfahren (a) und (b) zur Herstellung der Verbindungen der Formel (I) werden vorzugsweise unter Verwendung oder mehrerer Verdünnungsmittel durchgeführt. Als Verdünnungsmittel zur Durchführung der erfindungsgemäßen Verfahren (a) und (b) kommen alle unter den Reaktionsbedingungen inerten Lösungsmittel in Frage. Als Beispiele sind zu nennen: Halogenkohlenwasserstoffe, insbesondere Chlorkohlenwasserstoffe wie Tetrachlorethylen, Tetra- chlorethan, Dichlorpropan, Methylenchlorid, Dichlorbutan, Chloroform, Tetrachlorkohlenstoff, Trichlorethan, Trichlorethylen, Pentachlorethan, Difluorbenzol, 1,2-Dichlorethan, Chlorbenzol, Brombenzol, Dichlorbenzol, Chlortoluol, Trichlorbenzol; Alkohole wie Methanol, Ethanol, Isopropanol, Butanol; Ether wie Ethylpropylether, Methyl-tert-butylether, n-Butylether, Anisol, Phenethol, Cyclohexylmethylether, Dimethylether, Diethylether, Dipropylether, Diisopropylether, Di-n-propylether, Diisobutylether, Diisoamylether, Ethylenglycoldimethylether, Tetrahydrofuran, Dioxan, Dichlordiethylether und Polyether des Ethylenoxids und/oder Propylenoxids; Amine wie Trimethyl-, Triethyl-, Tripropyl-, Tributylamin, N-Methyl-morpholin, Pyridin und Tetramethylen- diamin, Nitrokohlenwasserstoffe wie Nitromethan, Nitroethan, Nitropropan, Nitrobenzol, Chlornitrobenzol, o-Nitrotoluol; Nitrile wie Acetonitril, Propionitril, Butyronitril, Isobutyronitril, Benzonitril, m-Chlorbenzonitril sowie Verbindungen wie Tetrahydrothiophenoxid und Dimethylsulfoxid, Tetramethylsulfoxid, Dipropylsulfoxid, Benzylmethylsulfoxid, Diisobutylsulf- oxid, Dibutylsulfoxid, Diisoamylsulfoxid; Sulfone wie Dimethyl-, Dieethyl-, Dipropyl-, Dibutyl-, Diphenyl-, Dihexyl-, Methylhexyl-, Ethylpropyl-, Ethylisobutyl- und Pentamethylensulfon; ali- phatische, cycloaliphatische oder aromatische Kohlenwasserstoffe, beispielsweise sogenannte White Spirits mit Komponenten mit Siedepunkten im Bereich beispielsweise von 400C bis 250°C, Cymol, Benzinfraktionen innerhalb eines Siedeintervalls von 700C bis 1900C, Cyclohexan, Methylcyclohexan, Petrolether, Ligroin, Octan, Benzol, Toluol, Chlorbenzol, Brombenzol, Nitrotoluol, Xylol; Ester wie Methyl-, Ethyl-, Butyl-, Isobutylacetat sowie Dimethyl-, Dibutyl-, Ethylencarbonat; Amide wie Hexamethylenphosphorsäuretriamid, Formamid, N-Methyl- formamid, N,N-Dimethyl-formamid, N,N-Dipropyl-formamid, N,N-Dibutyl-formamid, N-Methyl- pyrrolidin, N-Methyl-caprolactam, l,3-Dimethyl-3,4,5,6-tetrahydro-2(lH)pyrimidin, Octylpyrro- lidin, Octylcaprolactam, l,3-Dimethyl-2-imidazolindion, N-Formyl-piperidin, N,N'-1,4-Diformyl- piperazin; Ketone wie Aceton, Acetophenon, Methylethylketon, Methylbutylketon, Wasser.The processes (a) and (b) according to the invention for the preparation of the compounds of the formula (I) are preferably carried out using one or more diluents. Suitable diluents for carrying out the processes (a) and (b) according to the invention are all solvents which are inert under the reaction conditions. Examples include: halogenated hydrocarbons, especially chlorinated hydrocarbons such as tetrachlorethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene ; Alcohols such as methanol, ethanol, isopropanol, butanol; Ethers such as ethyl propyl ether, methyl tert-butyl ether, n-butyl ether, anisole, phenethol, cyclohexylmethyl ether, dimethyl ether, diethyl ether, dipropyl ether, diisopropyl ether, di-n-propyl ether, diisobutyl ether, diisoamyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, dichlorodiethyl ether and polyethers of ethylene oxide and or propylene oxide; Amines such as trimethyl, triethyl, tripropyl, tributylamine, N-methylmorpholine, pyridine and tetramethylenediamine, nitrohydrocarbons such as nitromethane, nitroethane, nitropropane, nitrobenzene, chloronitrobenzene, o-nitrotoluene; Nitriles such as acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile and also compounds such as tetrahydrothiophenoxide and dimethylsulfoxide, tetramethylsulfoxide, dipropylsulfoxide, benzylmethylsulfoxide, diisobutylsulfoxide, dibutylsulfoxide, diisoamylsulfoxide; Sulfones such as dimethyl, dieethyl, dipropyl, dibutyl, diphenyl, dihexyl, methylhexyl, ethylpropyl, ethylisobutyl and pentamethylene sulfone; ali- phatic, cycloaliphatic or aromatic hydrocarbons, for example so-called white spirits with components having boiling points in the range, for example from 40 0 C to 250 ° C, cymene, benzine fractions within a boiling range of 70 0 C to 190 0 C, cyclohexane, methylcyclohexane, petroleum ether, Ligroin, octane, benzene, toluene, chlorobenzene, bromobenzene, nitrotoluene, xylene; Esters such as methyl, ethyl, butyl, isobutyl acetate and dimethyl, dibutyl, ethylene carbonate; Amides such as hexamethylenephosphoric triamide, formamide, N-methylformamide, N, N-dimethylformamide, N, N-dipropylformamide, N, N-dibutylformamide, N-methylpyrrolidine, N-methyl-caprolactam, I, 3-Dimethyl-3,4,5,6-tetrahydro-2 (1H) pyrimidine, octylpyrrolidine, octylcaprolactam, 1,3-dimethyl-2-imidazolinedione, N-formyl-piperidine, N, N'-1,4 Diformylpiperazine; Ketones such as acetone, acetophenone, methyl ethyl ketone, methyl butyl ketone, water.
Die Reaktionstemperaturen können bei der Durchführung des erfindungsgemäßen Verfahrens in einem größeren Bereich variiert werden. Im Allgemeinen arbeitet man bei Temperaturen zwischen -500C und +1500C, vorzugsweise zwischen -2O0C und +1200C. Das erfϊndungsgemäße Verfahren wird im Allgemeinen unter Normaldruck durchgeführt. Es ist jedoch auch möglich, das erfindungsgemäße Verfahren unter erhöhtem oder vermindertem Druck - im Allgemeinen zwischen 0,1 bar und 15 bar - durchzuführen.The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, one works at temperatures between -50 0 C and +150 0 C, preferably between -2O 0 C and +120 0 C. The erfϊndungsgemäße process is generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally between 0.1 bar and 15 bar.
Zur Durchführung des erfindungsgemäßen Verfahrens werden die Ausgangsstoffe im Allgemeinen in angenähert äquimolaren Mengen eingesetzt. Es ist jedoch auch möglich, eine der Komponenten in einem größeren Überschuss zu verwenden. Die Umsetzung wird im Allgemeinen in einem geeigneten Verdünnungsmittel in Gegenwart eines Reaktionshilfsmittels, gegebenenfalls auch unter einer Schutzgas-Atmosphäre (z.B. unter Stickstoff, Argon oder Helium) durchgeführt und das Reaktionsgemisch wird im Allgemeinen mehrere Stunden bei der erforderlichen Temperatur gerührt. Die Aufarbeitung wird nach üblichen Methoden durchgeführt (vgl. die Herstellungsbeispiele).To carry out the process according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction aid, optionally under a protective gas atmosphere (e.g., under nitrogen, argon or helium), and the reaction mixture is generally stirred for several hours at the required temperature. The workup is carried out by customary methods (see the preparation examples).
Die erfindungsgemäßen Wirkstoffe der Formel (I) eignen sich bei guter Pflanzenverträglichkeit, günstiger Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen, zur Steigerung der Ernteerträge, Verbesserung der Qualität des Erntegutes und zur Bekämpfung von tierischen Schädlingen, insbesondere Insekten, Spinnentieren und Nematoden, die in der Landwirtschaft, in Forsten, in Gärten und Freizeiteinrichtungen, im Vorratsund Materialschutz sowie auf dem Hygienesektor vorkommen. Sie können vorzugsweise als Pflanzenschutzmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Zu den oben erwähnten Schädlingen gehören:The active compounds of the formula (I) according to the invention are suitable for plant tolerance, favorable warm-blooded toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids and nematodes. which occur in agriculture, forests, gardens and recreational facilities, in supplies and materials, and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development. The above mentioned pests include:
Aus der Ordnung der Isopoda z.B. Oniscus asellus, Armadillidium vulgäre, Porcellio scaber.From the order of isopods e.g. Oniscus asellus, Armadillidium vulgaris, Porcellio scaber.
Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus.From the order of diplopoda e.g. Blaniulus guttulatus.
Aus der Ordnung der Chilopoda z.B. Geophilus carpophagus, Scutigera spp..From the order of Chilopoda e.g. Geophilus carpophagus, Scutigera spp ..
Aus der Ordnung der Symphyla z.B. Scutigerella immaculata.From the order of Symphyla e.g. Scutigerella immaculata.
Aus der Ordnung der Thysanura z.B. Lepisma saccharina.From the order of Thysanura e.g. Lepisma saccharina.
Aus der Ordnung der Collembola z.B. Onychiurus armatus.From the order of Collembola e.g. Onychiurus armatus.
Aus der Ordnung der Orthoptera z.B. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.From the order of Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
Aus der Ordnung der Blattaria z.B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.From the order of the Blattaria e.g. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.
Aus der Ordnung der Dermaptera z.B. Forficula auricularia. Aus der Ordnung der Isoptera z.B. Reticulitermes spp.From the order of the Dermaptera eg Forficula auricularia. From the order of the Isoptera eg Reticulitermes spp.
Aus der Ordnung der Phthiraptera z.B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.From the order of Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
Aus der Ordnung der Thysanoptera z.B. Hercinothrips femoralis, Thrips tabaci, Thrips palmi, FranMiniella occidentalis.From the order of Thysanoptera e.g. Herculothrips femoralis, Thrips tabaci, Thrips palmi, FranMiniella occidentalis.
Aus der Ordnung der Heteroptera z.B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.From the order of Heteroptera, e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
Aus der Ordnung der Homoptera z.B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macro- siphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.From the order of Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum Padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
Aus der Ordnung der Lepidoptera z.B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofrnannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.From the order of Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis Spp., Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofrnannophila pseudospretella, Cacoecia podana, Capua reticulana Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus spp., Oulema oryzae.
Aus der Ordnung der Coleoptera z.B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varive- stis, Atomaria spp., Oryzaepbilus surinamensis, 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., Tenebrio molitor, Agriotes spp., Cono- derus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.From the order of Coleoptera e.g. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varvestis, Atomaria spp., Oryzaepbilus surinamensis, 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. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
Aus der Ordnung der Hymenoptera z.B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. Aus der Ordnung der Diptera z.B. Aedes spp., Anopheles spp., Culex 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., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.From the order of Hymenoptera eg Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of Diptera eg Aedes spp., Anopheles spp., Culex 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., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp ,
Aus der Ordnung der Siphonaptera z.B. Xenopsylla cheopis, Ceratophyllus spp.From the order of siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp.
Aus der Klasse der Arachnida z.B. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Pliyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.From the class of arachnids, e.g. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Pliyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp. Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
Zu den pflanzenparasitären Nematoden gehören z.B. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.The plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
Die erfindungsgemäßen Verbindungen der Formel (I) zeichnen sich insbesondere durch starke Wirkung gegen Blattläuse, z.B. Aphis spp. und Myzus spp. aus.The compounds of the formula (I) according to the invention are distinguished in particular by a strong action against aphids, e.g. Aphis spp. and Myzus spp. out.
Die erfindungsgemäßen Verbindungen können gegebenenfalls in bestimmten Konzentrationen bzw. Aufwandmengen auch als Herbizide oder als Safener hierfür, oder als Mikrobizide, beispielsweise als Fungizide, Antimykotika oder Bakterizide verwendet werden. Sie lassen sich gegebenenfalls auch als Zwischen- oder Vorprodukte für die Synthese weiterer Wirkstoffe einsetzen.If appropriate, the compounds according to the invention can also be used in certain concentrations or application rates as herbicides or as safeners for this purpose, or as microbicides, for example as fungicides, antimycotics or bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
Erfindungsgemäß können alle Pflanzen und Pflanzenteile behandelt werden. Unter Pflanzen werden hierbei alle Pflanzen und Pflanzenpopulationen verstanden, wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen (einschließlich natürlich vorkommender Kulturpflanzen). Kulturpflanzen können Pflanzen sein, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden öder Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten. Unter Pflanzenteilen sollen alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Sproß, Blatt, Blüte und Wurzel verstanden werden, wobei beispielhaft Blätter, Nadeln, Stengel, Stämme, Blüten, Fruchtkörper, Früchte und Samen sowie Wurzeln, Knollen und Rhizome aufgeführt werden. Zu den Pflanzenteilen gehört auch Erntegut sowie vegetatives und generatives Veπnehrungsmaterial, beispielsweise Stecklinge, Knollen, Rbizome, Ableger und Samen.According to the invention, all plants and parts of plants can be treated. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop 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 varieties which can or can not be protected by plant breeders' rights. Plant parts are to be understood as meaning all aboveground and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes. Part of the crop also includes crops as well vegetative and generative growth material, for example cuttings, tubers, Rbizome, offshoots and seeds.
Die erfmdungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, Sprühen, Verdampfen, Vernebeln, Streuen, Aufstreichen, Injizieren und bei Vermehrungsmaterial, insbesondere bei Samen, weiterhin durch ein- oder mehrschichtiges Umhüllen.The erfmdungsgemäße treatment of the plants and plant parts with the active ingredients is carried out directly or by affecting its environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, spreading, injecting and propagating material, in particular in seeds, further by single or multilayer coating.
Die Wirkstoffe können in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, Granulate, Suspensions-Emulsions-Konzentrate, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen.The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, active substance-impregnated natural and synthetic substances and superfine encapsulations in polymeric substances.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermischen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln.These formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen in Frage: Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid und Dimethylsulfoxid, sowie Wasser.In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
Als feste Trägerstoffe kommen in Frage:Suitable solid carriers are:
z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, als feste Trägerstoffe für Granulate kommen in Frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokosnußschalen, Maiskolben und Tabakstengeln; als Emulgier- und/oder schaumerzeugende Mittel kommen in Frage: z.B. nicht- ionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäure-Ester, Polyoxyethylen- Fettalkohol-Ether, z.B. Alkylaryl-polyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Einweißhydrolysate; als Dispergiermittel kommen in Frage: z.B. Lignin-Sulfitablaugen und Methylcellulose.For example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules in question: eg broken and fractionated natural rocks such Calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates as well as protein hydrolysates; suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulvrige, körnige oder latexförmige Polymere verwendet werden, wie Gurnmi- arabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.Adhesives such as carboxymethylcellulose, natural and synthetic powders, granules or latexes such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations. Other additives may be mineral and vegetable oils.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.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 zinc.
Die Formulierungen enthalten im allgemeinen ∑rwischen 0,1 und 95 Gew.-% Wirkstoff, vorzugsweise zwischen 0,5 und 90 %.The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
Der erfindungsgemäße Wirkstoff kann in seinen handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien, Bakteriziden, Akariziden, Nematoziden, Fungiziden, wachstumsregulierenden Stoffen oder Herbiziden vorliegen. Zu den Insektiziden zählen beispielsweise Phosphorsäureester, Carbamate, Carbonsäureester, chlorierte Kohlenwasserstoffe, Phenylharnstoffe, durch Mikroorganismen hergestellte Stoffe u.a.The active ingredient according to the invention can be present in its commercially available formulations as well as in the formulations prepared from these formulations in admixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematocides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphoric acid esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, microorganism-produced substances and the like.
Besonders günstige Mischpartner sind z.B. die folgenden:Particularly favorable mixing partners are e.g. the following:
Fungizide:fungicides:
2-Phenylphenol; δ-Hydroxyquinoline sulfate; Acibenzolar-S-methyl; Aldimorph; Amidoflumet; Ampropylfos; Ampropylfos-potassium; Andoprim; Anilazine; Azaconazole; Azoxystrobin; Benalaxyl; Benodanil; Benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; Bilanafos; Binapacryl; Biphenyl; Bitertanol; Blasticidin-S; Bromuconazole; Bupirimate; Buthiobate; Butylamine; Calcium polysulfide; Capsimycin; Captafol; Captan; Carbendazim; Carboxin; Carpropamid; Carvone; Chinomethionat; Chlobenthiazone; Chlorfenazole; Chloroneb; Chlorothalonil; Chlozolinate; Clozylacon; Cyazofamid; Cyflufenamid; Cymoxanil; Cypro- conazole; Cyprodinil; Cyprofuram; Dagger G; Debacarb; Dichlofluanid; Dichlone; Dichlorophen; Diclocymet; Diclomezine; Dicloran; Diethofencarb; Difenoconazole; Diflurnetorirn; Dimethirimol; Dimethomorph; Dimoxystrobin; Diniconazole; Diniconazole-M; Dinocap; Diphenylamine; Dipyrithione; Ditalimfos; Dithianon; Dodine; Drazoxolon; Edifenphos; Epoxiconazole; Ethaboxam; Ethirimol; Etridiazole; Famoxadone; Fenamidone; Fenapanil; Fenarimol; Fenbuconazole; Fenfuram; Fenhexamid; Fenitropan; Fenoxanil; Fenpiclonil; Fenpropidin; Fenpropimorph; Ferbam; Fluazinam; Flubenzimine; Fludioxonil; Flumetover; Flumorph; Fluoromide; Fluoxastrobin; Fluquinconazole; Flurprimidol; Flusilazole; Flusulfamide; Flutolanil; Flutriafol; Folpet; Fosetyl-Al; Fosetyl-sodium; Fuberidazole; Furalaxyl; Furametpyr; Furcarbanil; Furmecyclox; Guazatine; Hexachlorobenzene; Hexaconazole; Hymexazol; Imazalil; Itnibenconazole; Iminoctadine triacetate; Iminoctadine tris(albesüate); Iodocarb; Ipconazole; Iprobenfos; Iprodione; Iprovalicarb; Irumamycin; Isoprothiolane; Isovaledione; Kasugamycin; Kresoxim-methyl; Mancozeb; Maneb; Meferimzone; Mepanipyrim; Mepronil; Metalaxyl; Metalaxyl-M; Metconazole; Methasulfocarb; Methfuroxam; Metiram; Metominostrobin; Metsulfovax; Mildiomycin; Myclobutanil; Myclozolin; Natamycin; Nicobifen; Nitrothal- isopropyl; Noviflumuron; Nuarimol; Ofurace; Orysastrobin; Oxadixyl; Oxolinic acid; Oxpoconazole; Oxycarboxin; Oxyfenthiin; Paclobutrazol; Pefurazoate; Penconazole; Pencycuron; Phosdiphen; Phthalide; Picoxystrobin; Piperalin; Polyoxins; Polyoxorim; Probenazole; Prochloraz; Procymidone; Propamocarb; Propanosine-sodium; Propiconazole; Propineb; Proquinazid; Prothioconazole; Pyraclostrobin; Pyrazophos; Pyrifenox; Pyrimethanil; Pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; Quinoxyfen; Quintozene; Simeconazole; SpiroxamiBe; Sulfur; Tebuconazole; Tecloftalam; Tecnazene; Tetcyclacis; Tetraconazole; Thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl; Tbiram; Tioxymid; Tolclofos-rαethyl; Tolylfluanid; Triadimefon; Triadimenol; Triazbutil; Triazoxide; Tricyclamide; Tricyclazole; Tridemorph; Trifloxystrobin; Triflumizole; Triforine; Triticonazole; Uniconazole; Validamycin A; Vinclozolin; Zineb; Ziram; Zoxamide; (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]- ethyl]-3-methyl- 2-[(methylsulfonyl)amino]-butanamide; l-(l-naphthalenyl)-lH-pyrrole-2,5-dione; 2,3,5,6-tetracmoro-4-(methylsulfonyl)-pyridine; 2-amino-4-methyl-N-plienyl-5-thiazolecarbox- amide; 2-chloro-N-(2,3-dihydro-l,l,3-trimethyl-lH-inden-4-yl)-3-pyridincarboxamide; 3,4,5-tri- chloro-2,6-pyridinedicarbonitrile; Actinovate; cis-l-(4-chlorophenyl)-2-(lH-l,2,4-triazole-l-yl)- cycloheptanol; methyl l-(2,3-dihydro-2,2-dimethyl-lH-iiiden-l-yl)-lH-iinidazole-5-carboxylate; monopotassium carbonate; N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide; N-butyl-8-(l,l- dimethylethyl)-l-oxaspiro[4.5]decan-3-amine; Sodium tetrathiocarbonate;2-phenylphenol; δ-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin; benalaxyl; Benodanil; benomyl; Benthiavalicarb-isopropyl; Benzamacril; Benzamacril-isobutyl; bilanafos; binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate; Buthiobate; butylamine; Calcium polysulfides; capsimycin; captafol; captan; carbendazim; carboxin; carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; Cyproconazole; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen; diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole; Diflurnetorirn; dimethirimol; dimethomorph; dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines; Dipyrithione; Ditalimfos; dithianon; dodine; Drazoxolon; edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole; famoxadone; fenamidone; Fenapanil; fenarimol; Fenbuconazole; fenfuram; fenhexamid; Fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph; ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; flumorph; fluoromides; fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil; flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil; Furmecyclox; guazatine; Hexachlorobenzene; hexaconazole; hymexazol; imazalil; Itnibenconazole; Iminoctadine triacetate; Iminoctadine tris (algesüate); iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb; Irumamycin; isoprothiolane; Isovaledione; kasugamycin; Kresoxim-methyl; mancozeb; maneb; Meferimzone; mepanipyrim; mepronil; metalaxyl; Metalaxyl-M; metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin; Metsulfovax; mildiomycin; myclobutanil; myclozoline; natamycin; nicobifen; Nitrothal isopropyl; Noviflumuron; nuarimol; ofurace; orysastrobin; oxadixyl; Oxolinic acid; Oxpoconazole; oxycarboxin; Oxyfenthiin; paclobutrazol; Pefurazoate; penconazole; pencycuron; phosdiphen; phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz; procymidone; propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid; prothioconazole; pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; SpiroxamiBe; Sulfur; tebuconazole; tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen; Thifluzamide; Thiophanate-methyl; Tbiram; Tioxymid; Tolclofos-rαethyl; tolylfluanid; triadimefon; triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin; Zineb; ziram; zoxamide; (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] - butanamide; l- (l-naphthalenyl) -lH-pyrrole-2,5-dione; 2,3,5,6-tetracmoro-4- (methylsulfonyl) -pyridine; 2-amino-4-methyl-N-plienyl-5-thiazolecarboxamides; 2-chloro-N- (2,3-dihydro-l, l, 3-trimethyl-lH-inden-4-yl) -3-pyridinecarboxamides; 3,4,5-trichloro-2,6-pyridinedicarbonitrile; Actinovate; cis-1- (4-chlorophenyl) -2- (1H-l, 2,4-triazole-1-yl) -cycloheptanol; methyl 1- (2,3-dihydro-2,2-dimethyl-1H-iiidene-1-yl) -1H-imidazole-5-carboxylate; monopotassium carbonate; N- (6-methoxy-3-pyridinyl) -cyclopropanecarboxamide; N-butyl-8- (1,1-dimethylethyl) -1-oxaspiro [4.5] decane-3-amine; Sodium tetrathiocarbonate;
sowie Kupfersalze und -Zubereitungen, wie Bordeaux mixture; Copper hydroxide; Copper naphthenate; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxide; Mancopper; Oxine- copper.and copper salts and preparations, such as Bordeaux mixture; Copper hydroxide; Copper naphthenates; Copper oxychloride; Copper sulfate; Cufraneb; Cuprous oxides; mancopper; Oxine-copper.
Bakterizide:bactericides:
Bronopol, Dichlorophen, Nitrapyrin, Nickel-Dimethyldithiocarbamat, Kasugamycin, Octhilinon, Furancarbonsäure, Oxytetracyclin, Probenazol, Streptomycin, Tecloftalam, Kupfersulfat und andere Kupfer-Zubereitungen. Insektizide / Akarϊzide / Nematϊzide:Bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations. Insecticides / Acarϊzide / Nematϊzide:
1. Acetylcholinesterase (AChE) Inhibitoren1. Acetylcholinesterase (AChE) inhibitors
1.1 Carbamate, zum Beispiel1.1 carbamates, for example
Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Dimetilan, Ethiofencarb, Fenobucarb, Fenothiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Trimethacarb, XMC, Xylylcarb TriazamateAlanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb, metam-sodium, methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Trimethacarb, XMC, Xylylcarb Triazamate
1.2 Organophosphate, zum Beispiel1.2 Organophosphates, for example
Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl/-ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthion, Dichlor- vos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fos- methilan, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl/-ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl/- ethyl), Profenofos, Propaphos, Propetamphos, Prothiofosä Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, Vamidothion 2. Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-BlockerAcephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromophos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl / -ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methyl sulphone, Dialifos, Diazinon, Dichlofenthione, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilane, Fosthiazate, Heptenophos, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl O-salicylates, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate , Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl / -ethyl), Profenofos, Propaphos, Propetamphos, Prothiofos a Pr othoate, pyraclofos, pyridaphenthion, pyridathion, quinalphos, sebufos, sulfotep, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometone, triazophos, triclorfone, vamidothion 2. Sodium Channel Modulators / Voltage-Dependent Sodium Channel Blockers
2.1 Pyrethroide, zum Beispiel2.1 Pyrethroids, for example
Acrinathrin, Allethrin (d-cis-trans, d-trans), Beta-Cyfluthrin, Bifenthrin, Bioallethrin, Bioallethriα-S-cyclopentyl-isomer, Bioethanomethrin, Biopermethrin, Bioresmethrin, Chlovaporthrin, Cis-Cypermethrin, Cis-Resmethrin, Cis- Permethrin, Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, Deltamethrin, Empenthrin (lR-isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fenvalerate, Flubrocythrinate, Flucythrinate, Flufenprox, Flumethrin, Fluvalinate,Acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethri-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin , Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, Deltamethrin, Empenthrin (IR-isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fenvalerate, Flubrocythrinate, Flucythrinate , Flufenprox, flumethrin, fluvalinate,
Fubfenprox, Gamma-Cyhalothrin, Imiprothrin, Kadethrin, Lambda- Cyhalothrin, Metofluthrin, Permethrin (eis-, trans-), Phenothrin (lR-trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmetlirin, Resmethrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetramethrin (-1R- isomer), Tralomethrin, Transfluthrin, ZXI 8901, Pyrethrins (pyrethrum) DDTFubfenprox, gamma-cyhalothrin, imiprothrin, kadethrin, lambda-cyhalothrin, metofluthrin, permethrin (cis-, trans-), phenothrin (IR trans isomer), prallethrin, profuthrin, protrifenbutene, pyresmetlirine, resmethrin, RU 15525, silafluofen, tau- Fluvalinates, tefluthrin, terallethrin, tetramethrin (-1R isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum) DDT
2.2 Oxadiazine, zum Beispiel Indoxacarb2.2 Oxadiazines, for example indoxacarb
3. Acetylcholin-Rezeptor-Agonisten/- Antagonisten3. Acetylcholine receptor agonists / antagonists
3.1 Chloronicotinyle, zum Beispiel3.1 Chloronicotinyls, for example
Acetarπiprid, Clothianidin, Dinotefuran, Imidacloprid, Nitenpyram, Nithiazine,Acetarπipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazines,
Thiacloprid,thiacloprid,
Thiamethoxamthiamethoxam
3.2 Nicotine, Bensultap, Cartap3.2 Nicotine, Bensultap, Cartap
4. Acetylcholin-Rezeptor-Modulatoren4. Acetylcholine receptor modulators
4.1 Spiαosyne, zum Beispiel Spinosad4.1 Spinosar, for example spinosad
5. GABA-gesteuerte Chlorid-Kanal- Antagonisten5. GABA-directed chloride channel antagonists
5.1 Cyclodiene Organochlorine, zum Beispiel5.1 Cyclodienes Organochlorines, for example
Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH, Heptachlor, Lindane, Methoxychlor 5.2 Fiprole, zum BeispielCamphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor 5.2 Fiprole, for example
Acetoprole, Ethiprole, Fipronil, VaniliproleAcetoprole, ethiprole, fipronil, vaniliprole
6. Chlorid-Kanal-Aktivatoren6. Chloride Channel Activators
6.1 Mectine, zum Beispiel6.1 Mectins, for example
Avermectin, Emamectin, Emamectin-benzoate, Ivermectin, MilbemycinAvermectin, emamectin, emamectin benzoate, ivermectin, milbemycin
7. Juvenilhormon-Mimetika, zum Beispiel7. Juvenile hormone mimetics, for example
Diofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, TripreneDiofenolan, Epofenonane, Fenoxycarb, Hydroprene, Kinoprene, Methoprene, Pyriproxifen, Triprene
8. Ecdysonagonisten/disruptoren8. ecdysonagonists / disruptors
8.1 Diacylhydrazine, zum Beispiel8.1 Diacylhydrazines, for example
Chromafenozide, Halofenozide, Methoxyfenozide, TebufenozideChromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide
9. Inhibitoren der Chitinbiosynthese9. Inhibitors of chitin biosynthesis
9.1 Benzoylharnstoffe, zum Beispiel9.1 Benzoylureas, for example
Bistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron, TriflumuronBistrifluron, Chlofluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penflurone, Teflubenzuron, Triflumuron
9.2 Buprofezin9.2 Buprofezin
9.3 Cyromazine9.3 Cyromazine
10. Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren10. Inhibitors of oxidative phosphorylation, ATP disruptors
10.1 Diafenthiuron10.1 Diafenthiuron
10.2 Organotine, zum Beispiel Azocyclotin, Cyhexatin, Fenbutatin-oxide10.2 Organotins, for example azocyclotin, cyhexatin, fenbutatin oxides
11. Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Protongradienten11. Decoupling of oxidative phosphorylation by interruption of the H proton gradient
11.1 Pyrrole, zum Beispiel Chlorfenapyr ' 11.1 Pyrroles, for example Chlorfenapyr '
11.2 Dinitrophenole, zum Beispiel Binapacyrl, Dinobuton, Dinocap, DNOC 12. Seite-I-Elektxonentransportinhibitoren11.2 Dinitrophenols, for example binapacyrl, dinobutone, dinocap, DNOC 12. Side-I Electron Transport Inhibitors
12.1 METI's, zum Beispiel Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad12.1 METI's, for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad
12.2 Hydramethylnon12.2 Hydramethylnone
12.3 Dicofol12.3 Dicofol
13. Seite-II-Elektronentransportinhibitoren13. Side II Electron Transport Inhibitors
RotenoneRotenone
14. Seite-m-Elektronentransportinhibitoren14. Side-m Electron Transport Inhibitors
Acequinocyl, FluaciypyrimAcequinocyl, Fluaciypyrim
15. Mikrobielle Disruptoren der Insektendarmmembran15. Microbial disruptors of insect intestinal membrane
Bacillus thurmgiensis-StämmeBacillus thurmgiensis strains
16. Inhibitoren der Fettsynthese16. Inhibitors of fat synthesis
16.1 Tetronsäuren, zum Beispiel16.1 Tetronic acids, for example
Spirodiclofen, SpiromesifenSpirodiclofen, spiromesifen
16.2 Tetramsäuren, zum Beispiel16.2 Tetramic acids, for example
3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-l-azaspiro[4.5]dec-3-en-4-yl ethyl carbonate (alias: Carbonic acid, 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-l- azaspiro[4.5]dec-3-en-4-yl ethyl ester, CAS-Reg.-No.: 382608-10-8) and Carbonic acid, cis-3 -(2,5 -dimethylphenyl)-8-methoxy-2-oxo- 1 -azaspiro [4.5] dec-3 -en-4-yl ethyl ester (CAS-Reg.-No.: 203313-25-1)3- (2,5-Dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl carbonate (also known as: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS Reg. No .: 382608-10-8) and carbonic acid, cis-3 - ( 2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3 -en-4-yl ethyl ester (CAS Reg. No .: 203313-25-1)
17. Carboxamide, zum Beispiel Flonicamid17. Carboxamides, for example flonicamide
18. Oktopaminerge Agonisten, zum B eispiel Amitraz18. Octopaminergic agonists, for example Amitraz
19. Inhibitoren der Magnesium-stimulierten ATPase, zum B eispiel Propargite 20. BDCAs, zum Beispiel N2-[l,l-Dimethyl-2-(methylsulfonyl)ethyl]-3-iodo-Nl-[2-methyl-4- [l,2,2,2-tetrafluoro-l-(trifluoromethyl)ethyl]phenyl]-l,2-benzenedicarboxamide (CAS- Reg.-No.: 272451-65-7)19. Inhibitors of magnesium-stimulated ATPase, for example propargite 20. BDCAs, for example N 2 - [l, l -dimethyl-2- (methylsulfonyl) ethyl] -3-iodo-N - [2-methyl-4- [l, 2,2,2-tetrafluoro-l- ( trifluoromethyl) ethyl] phenyl] -l, 2-benzenedicarboxamide (CAS Reg. No .: 272451-65-7)
21. Nereistoxin-Analoge, zum B eispiel Thiocyclam hydrogen Oxalate, Thiosultap-sodium21. Nereistoxin analogs, for example thiocyclam hydrogen oxalate, thiosultap-sodium
22. Biologika, Hormone oder Pheromone, zum Beispiel22. Biologics, hormones or pheromones, for example
Azadirachtin, Bacillus spec, Beauveria spec, Codlemone, Metarrhizium spec, Paecilomyces spec, Thuringiensin, Verticillium spec.Azadirachtin, bacillus spec, beauveria spec, codlemone, metarrhicon spec, paecilomyces spec, thuringiensin, verticillium spec.
23. Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen23. Active substances with unknown or non-specific mechanisms of action
23.1 Begasungsmittel, zum Beispiel23.1 fumigants, for example
Aluminium phosphide, Methyl bromide, Sulfuryl fluorideAluminum phosphides, methyl bromides, sulfuryl fluorides
23.2 Selektive Fraßhemmer, zum Beispiel23.2 Selective feed inhibitors, for example
Cryolite, Flonicamid, PymetrozineCryolites, flonicamid, pymetrozines
23.3 Milbenwachstumsinhibitoren, zum Beispiel23.3 mite growth inhibitors, for example
Clofentezine, Etoxazole, HexythiazoxClofentezine, etoxazole, hexythiazox
23.4 Amidoflumet, Benclothiaz, Benzoximate, Bifenazate, Bromopropylate, Buprofezin, Chino- methionat, Chlordimeform, Chlorobenzilate, Chloropicrin, Clothiazoben, Cycloprene, Cyflumetofen, Dicyclanil, Fenoxacrim, Fentrifanil, Flubendiamide, Flubenzimine, FIu- fenerim, Flutenzin, Gossyplure, Hydramethylnone, Japonilure, Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene,Verbutin23.4 Amidoflumet, benclothiazole, benzoximate, bifenazate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzilate, chloropicrin, clothiazoben, cycloprene, cyflumetofen, dicyclanil, fenoxacrim, fentrifanil, flubendiamide, flubenzimine, flufenerim, flotenzin, gossyplaine, hydramethylnone, japonilure , Metoxadiazone, Petroleum, Piperonyl butoxide, Potassium oleate, Pyrafluprole, Pyridalyl, Pyriprole, Sulfluramid, Tetradifon, Tetrasul, Triarathene, Verbutin
sowie Präparate, welche insektizid wirksame Pflanzenextrakte, Nematoden, Pilze oder Viren enthalten.and preparations containing insecticidal plant extracts, nematodes, fungi or viruses.
Auch eine Mischung mit anderen bekannten Wirkstoffen, wie Herbiziden, Düngemitteln, Wachstumsregulatoren, Safenern oder Semiochemicals ist möglich.A mixture with other known active substances, such as herbicides, fertilizers, growth regulators, safeners or semiochemicals is possible.
Die erfindungsgemäßen Wirkstoffe können ferner beim Einsatz als Insektizide in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit Synergisten vorliegen. Synergisten sind Verbindungen, durch die die Wirkung der Wirkstoffe gesteigert wird, ohne daß der zugesetzte Synergist selbst aktiv wirksam sein muß.The active compounds according to the invention can furthermore be employed as insecticides in their commercial formulations and in the forms of use prepared from these formulations in mixture with synergists. Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
Die erfϊndungsgemäßen Wirkstoffe können ferner beim Einsatz als Insektizide in ihren handelsüblichen Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischungen mit Hemmstoffen vorliegen, die einen Abbau des Wirkstoffes nach Anwendung in der Umgebung der Pflanze, auf der Oberfläche von Pflanzenteilen oder in pflanzlichen Geweben vermindern.The active compounds according to the invention can furthermore, when used as insecticides, be present in their commercial formulations and in the forms of use prepared from these formulations in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
Der Wirkstoffgehalt der aus den handelsüblichen Formulierungen bereiteten Anwendungsformen kann in weiten Bereichen variieren. Die Wirkstoffkonzentration der Anwendungsformen kann von 0,0000001 bis zu 95 Gew.~% Wirkstoff, vorzugsweise zwischen 0,0001 und 1 Gew.-% liegen.The active substance content of the application forms prepared from the commercial formulations can vary within wide ranges. The active ingredient concentration of the use forms may be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
Die Anwendung geschieht in einer den Anwendungsformen angepaßten üblichen Weise.The application is done in a custom forms adapted to the application.
Bei der Anwendung gegen Hygiene- und Vorratsschädlinge zeichnet sich der Wirkstoff durch eine hervorragende Residualwirkung auf Holz und Ton sowie durch eine gute Alkalistabilität auf gekalkten Unterlagen aus.When used against hygiene and storage pests, the active ingredient is characterized by an excellent residual effect on wood and clay and by a good alkali stability on limed substrates.
Wie bereits oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden. In einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetic Modified Organisms) und deren Teile behandelt. Der Begriff "Teile" bzw. "Teile von Pflanzen" oder "Pflanzenteile" wurde oben erläutert.As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated. The term "parts" or "parts of plants" or "plant parts" has been explained above.
Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Bio- und Genotypen sein.It is particularly preferred according to the invention to treat plants of the respective commercially available or in use plant cultivars. Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
Je nach Pflanzenarten bzw. Pflanzensorten, deren Standort und Wachstumsbedingungen (Böden, Klima, Vegetationsperiode, Ernährung) können durch die erfindungsgemäße Behandlung auch überadditive ("synergistische") Effekte auftreten. So sind beispielsweise erniedrigte Aufwandmengen und/oder Erweiterungen des Wirkungsspektrums und/oder eine Verstärkung der Wirkung der erfindungsgemäß verwendbaren Stoffe und Mittel, besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen.Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also give rise to superadditive ("synergistic") effects. Thus, for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to Dryness or against water or soil salt content, increased flowering power, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the actual expected effects ,
Zu den bevorzugten erfϊndungsgemäß zu behandelnden transgenen (gentechnologisch erhaltenen)Among the preferred transgenic (genetically engineered) to be treated according to the invention
Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvollePlants or plant varieties include all plants that received genetic material through the genetic modification, which these plants particularly advantageous valuable
Eigenschaften ("Traits") verleiht. Beispiele für solche Eigenschaften sind besseresProperties ("traits"). Examples of such properties are better
Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhtePlant growth, increased tolerance to high or low temperatures, increased
Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit derTolerance against dryness or against water or soil salt content, increased flowering power, easier harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability
Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüberHarvested products. Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as opposed to
Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhteInsects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased
Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel,Tolerance of the plants against certain herbicidal active substances. Examples of transgenic plants are the important crops, such as cereals (wheat, rice), corn, soy, potato,
Baumwolle, Tabak, Raps sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten undCotton, tobacco, oilseed rape as well as fruit plants (with the fruits apples, pears, citrus fruits and
Weintrauben) erwähnt, wobei Mais, Soja, Kartoffel, Baumwolle, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften ("Traits") werden besonders hervorgehoben die erhöhteGrapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape. As properties ("Traits") are particularly emphasized the increased
Abwehr der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken durch in denDefend the plants against insects, arachnids, nematodes and snails in the
Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus BacillusToxins produced by plants, in particular those produced by the genetic material from Bacillus
Thuringiensis (z.B. durch die Gene CryΙA(a), CryIA(b), CryΙA(c), CryllA, CrylEA, CryIIIB2,Thuringiensis (e.g., by the genes CryΙA (a), CryIA (b), CryΙA (c), CryllA, CrylEA, CryIIIB2,
Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werdenCry9c Cry2Ab, Cry3Bb and CrylF and their combinations) in the plants
(im folgenden "Bt Pflanzen"). Als Eigenschaften ("Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte(in the following "Bt plants"). As traits, the increased defense of plants against fungi, bacteria and viruses by systemic acquired are also particularly emphasized
Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften ("Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirkstoffen, beispielsweise Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B.Resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits that are further emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (e.g.
"PAT"-Gen). Die jeweils die gewünschten Eigenschaften ("Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für "Bt"PAT" gene). The genes which confer the desired properties ("traits") can also occur in combinations with one another in the transgenic plants. As examples of "Bt
Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YIELD GARD® (z.B. Mais, Baumwolle, Soja), KnockOut® (z.B.Plants "are said to be maize, cotton, soya and potato varieties sold under the trade names YIELD GARD® (e.g., corn, cotton, soy), KnockOut® (e.g.
Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle) und NewLeaf®Corn), StarLink® (e.g., corn), Bollgard® (cotton), Nucotn® (cotton), and NewLeaf®
(Kartoffel) vertrieben werden. Als Beispiele für Herbizid-tolerante Pflanzen seien Maissorten,(Potato) are sold. Examples of herbicide-tolerant plants are maize varieties,
Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready®Cottons and soybean varieties, known under the trade names Roundup Ready®
(Toleranz gegen Glyphosate z.B. Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinotricin, z.B. Raps), IMI® (Toleranz gegen Imidazolinone) und STS® (Toleranz gegen Sulfonylharnstoffe z.B. Mais) vertrieben werden. Als Herbizid resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfield® vertriebenen Sorten (z.B. Mais) erwähnt. Selbstverständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften ("Traits").(Tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to Phosphinotricin, eg rapeseed), IMI® (tolerance to imidazolinone) and STS® (tolerance to sulfonylureas eg corn). Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to future or future marketed plant varieties with these or future developed genetic traits.
Die aufgeführten Pflanzen können besonders vorteilhaft erfϊndungsgemäß mit den Verbindungen der allgemeinen Formel I bzw. den erfindungsgemäßen Wirkstoffmischungen behandelt werden. Die bei den Wirkstoffen bzw. Mischungen oben angegebenen Vorzugsbereiche gelten auch für die Behandlung dieser Pflanzen. Besonders hervorgehoben sei die Pflanzenbehandlung mit den im vorliegenden Text speziell aufgeführten Verbindungen bzw. Mischungen.The plants listed can be treated particularly advantageously erfϊndungsgemäß with the compounds of the general formula I or the active substance mixtures according to the invention. The preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants. Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
Die erfindungsgemäßen Wirkstoffe wirken nicht nur 'gegen Pflanzen-, Hygiene- und Vorratsschädlinge, sondern auch auf dem veterinärmedizinischen Sektor gegen tierische Parasiten (Ektoparasiten) wie Schildzecken, Lederzecken, Räudemilben, Laufmilben, Fliegen (stechend und leckend), parasitierende Fliegenlarven, Läuse, Haarlinge, Federlinge und Flöhe.The active compounds of the invention not only 'against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ectoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair pieces , Featherlings and fleas.
Zu diesen Parasiten gehören:These parasites include:
Aus der Ordnung der Anoplurida z.B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.From the order of the Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
Aus der Ordnung der Mallophagida und den Unterordnungen Amblycerina sowie Ischnocerina z.B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.From the order of Mallophagida and suborders Amblycerina and Ischnocerina, for example. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
s der Ordnung Diptera und den Unterordnungen Nematocerina sowie Brachycerina z.B. Aedes i., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia i., 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 S sDptp)..., L Liinpoonptteennaa S sDpΌp..,. M Meelloonphhaageπuss s stprap..s of the order Diptera and the suborders Nematocerina and Brachycerina e.g. Aedes i., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia i., 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 s sptpt) ..., L Liinpoonptteennaa S sDpΌp ..,. M Meelloonphhaageπuss s stprap ..
Aus der Ordnung der Siphonapterida z.B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.From the order of siphonapterida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
Aus der Ordnung der Heteropterida z.B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. Aus der Ordnung der Blattarida z.B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.From the order of the Heteropterida eg Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. From the order Blattarida eg Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.
Aus der Unterklasse der Acari (Acarina) und den Ordnungen der Meta- sowie Mesostigmata z.B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.From the subclass of Acari (Acarina) and the orders of Meta and Mesostigmata e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp ., Sternostoma spp., Varroa spp.
Aus der Ordnung der Actinedida (Prostigmata) und Acaridida (Astigmata) z.B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.From the order of Actinedida (Prostigmata) and Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
Die erfindungsgemäßen Wirkstoffe der Formel (I) eignen sich auch zur Bekämpfung von Arthropoden, die landwirtschaftliche Nutztiere, wie z.B. Rinder, Schafe, Ziegen, Pferde, Schweine, Esel, Kamele, Büffel, Kaninchen, Hühner, Puten, Enten, Gänse, Bienen, sonstige^Haustiere wie z.B. Hunde, Katzen, Stubenvögel, Aquarienfische sowie sogenannte Versuchstiere, wie z.B.The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, miscellaneous animals such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such.
Hamster, Meerschweinchen, Ratten und Mäuse befallen. Durch die Bekämpfung dieser Arthropoden sollen Todesfälle und Leistungsminderungen (bei Fleisch, Milch, Wolle, Häuten,Hamsters, guinea pigs, rats and mice. By controlling these arthropods deaths and reductions in performance (meat, milk, wool, skins,
Eiern, Honig usw.) vermindert werden, so daß durch den Einsatz der erfindungsgemäßen Wirkstoffe eine wirtschaftlichere und einfachere Tierhaltung möglich ist.Eggs, honey, etc.) are reduced, so that a more economical and easier animal husbandry is possible by the use of the active compounds according to the invention.
Die Anwendung der erfindungsgemäßen Wirkstoffe geschieht im Veterinärsektor in bekannter Weise durch enteräle Verabreichung in Form von beispielsweise Tabletten, Kapseln, Tränken, Drenchen, Granulaten, Pasten, BoIi, des feed-through- Verfahrens, von Zäpfchen, durch parenterale Verabreichung, wie zum Beispiel durch Injektionen (intramuskulär, . subcutan, intravenös, intraperitonal u.a.), Implantate, durch nasale Applikation, durch dermale Anwendung in Form beispielsweise des Tauchens oder Badens (Dippen), Sprühens (Spray), Aufgießens (Pour-on und Spot-on), des Waschens, des Einpuderns sowie mit Hilfe von wirkstoffhaltigen Formkörpern, wie Halsbändern, Ohrmarken, Schwanzmarken, Gliedmaßenbändern, Halftern, Markierungsvorrichtungen usw.The application of the active compounds according to the invention in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, Drenchen, granules, pastes, BoIi, the feed-through process, suppositories, by parenteral administration, such as by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, dipping or bathing (dipping), spraying, pouring on and spot-on, Washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, marking devices, etc.
Bei der Anwendung für Vieh, Geflügel, Haustiere etc. kann man die Wirkstoffe der Formel (I) als Formulierungen (beispielsweise Pulver, Emulsionen, fließfähige Mittel), die die Wirkstoffe in einer Menge von 1 bis 80 Gew.-% enthalten, direkt oder nach 100 bis 10 000-facher Verdünnung anwenden oder sie als chemisches Bad verwenden.In the application for livestock, poultry, pets, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.
Außerdem wurde gefunden, daß die erfindungsgemäßen Verbindungen eine hohe insektizide Wirkung gegen Insekten zeigen, die technische Materialien zerstören.. Beispielhaft und vorzugsweise - ohne jedoch zu limitieren - seien die folgenden Insekten genannt:In addition, it has been found that the compounds according to the invention exhibit a high insecticidal activity against insects which destroy industrial materials. By way of example and preferably without limiting however, the following insects are mentioned:
Käfer wie Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus;Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus;
Hautflügler wie Sirex juvencus, Urocems gigas, Urocerus gigas taignus, Urocerus augur;Hymenoptera such as Sirex juvencus, Urocem's gigas, Urocerus gigas taignus, Urocerus augur;
Termiten wie Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
Borstenschwänze wie Lepisma saccharina.Bristle tails like Lepisma saccharina.
Unter technischen Materialien sind im vorliegenden Zusammenhang nicht-lebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartonέf, Leder, Holz, Holzverar^eitungsprodukte und Anstrichmittel.Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
" \ Ganz besonders bevorzugt handelt es sich bei dem vor Insektenbefall zu schützenden Material um "It is very particularly preferable for the material to be protected from insect infestation
Holz und Holzverarbeitungsprodukte.Wood and woodwork products.
Unter Holz und Holzverarbeitungsprodukten, welche durch das erfϊndungsgemäße Mittel bzw. dieses enthaltende Mischungen geschützt werden kann, ist beispielhaft zu verstehen:By wood and woodworking products, which can be protected by the erfϊndungsgemäße means or mixtures containing it, is to be understood as an example:
Bauholz, Holzbalken, Eisenbahnschwellen, Brückenteile, Bootsstege, Holzfahrzeuge, Kisten, Paletten, Container, Telefonmasten, Holzverkleidungen, Holzfenster und -türen, Sperrholz, Spanplatten, Tischlerarbeiten oder Holzprodukte, die ganz allgemein beim Hausbau oder in der Bautischlerei Verwendung finden.Timber, wooden beams, railway sleepers, bridge parts, boat jetties, wooden vehicles, crates, pallets, containers, telephone poles, wooden cladding, wooden windows and doors, plywood, chipboard, carpentry or wood products, which are generally used in home construction or joinery.
Die Wirkstoffe können als solche, in Form von Konzentraten oder allgemein üblichen Formulierungen wie Pulver, Granulate, Lösungen, Suspensionen, Emulsionen oder Pasten angewendet werden.The active compounds can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
Die genannten Formulierungen können in an sich bekannter Weise hergestellt werden, z.B. durch Vermischen der Wirkstoffe mit mindestens einem Lösungs- bzw. Verdünnungsmittel, Emulgator, Dispergier- und/oder Binde- oder Fixiermittel, Wasser-Repellent, gegebenenfalls Sikkative und UV-Stabilisatoren und gegebenenfalls Farbstoffen und Pigmenten sowie weiteren Verarbeitungshilfsmitteln. Die zum Schutz von Holz und Hblzwerkstoffen verwendeten insektiziden Mittel oder Konzentrate enthalten den erfindungsgemäßen Wirkstoff in einer Konzentration von 0,0001 bis 95 Gew.-%, insbesondere 0,001 bis 60 Gew.-%.The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally Dyes and pigments and other processing aids. The insecticidal agents or concentrates used for the protection of wood and Hbzwerkstoffen contain the active ingredient according to the invention in a concentration of 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.
Die Menge der eingesetzten Mittel bzw. Konzentrate ist von der Art und dem Vorkommen der Insekten und von dem Medium abhängig. Die optimale Einsatzmenge kann bei der Anwendung jeweils durch Testreihen ermittelt werden. Im allgemeinen ist es jedoch ausreichend 0,0001 bis 20 Gew.-%, vorzugsweise 0,001 bis 10 Gew.-%, des Wirkstoffs, bezogen auf das zu schützende Material, einzusetzen.The amount of agents or concentrates used depends on the nature and occurrence of the insects and on the medium. The optimal amount used 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 ingredient, based on the material to be protected.
Als Lösungs- und/oder Verdünnungsmittel dient ein organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/oder ein öliges oder ölartiges schwer flüchtiges organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/oder ein polares organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch und/oder Wasser und gegebenenfalls einen Emulgator und/oder Netzmittel.The solvent and / or diluent used is an organic-chemical solvent or solvent mixture and / or an oily or oily high-volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.
Als organisch-chemische Lösungsmittel werden vorzugsweise ölige oder ölartige^Lösurigsmittel mit einer Verdunstungszahl über 35 und einem Flammpunkt oberhalb 3O0C, vorzugsweise oberhalb 45°vC, "eingesetzt. Als derartige schwerflüchtige, wasserunlösliche, ölige und ölartige Lösungsmittel " werden entsprechende Mineralöle oder deren Aromatenfraktionen oder mineralölhaltige Lösungsmittelgemische, vorzugsweise Testbenzin, Petroleum und/oder Alkylbenzol verwendet.Organic chemical solvents which are preferably oily or oil-like ^ Lösurigsmittel having an evaporation number above 35 and a flashpoint above 3O 0 C, preferably above 45 ° v C, "inserted. As such a low-volatile, water-insoluble, oily and oil-type solvents" are appropriate mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene used.
Vorteilhaft gelangen Mineralöle mit einem Siedebereich von 170 bis 2200C, Testbenzin mit einem Siedebereich von 170 bis 22O0C, Spindelöl mit einem Siedebereich von 250 bis 3500C, Petroleum bzw. Aromaten vom Siedebereich von 160 bis 2800C, Terpentinöl und dgl. zum Einsatz.Mineral oils having a boiling range of 170 to 220 0 C, white spirit having a boiling range of 170 to 22O 0 C, spindle oil with a boiling range of 250 to 350 0 C, petroleum and aromatics with a boiling range of 160 to 280 0 C, oil of turpentine and Like. For use.
In einer bevorzugten Ausführungsform werden flüssige aliphatische Kohlenwasserstoffe mit einem Siedebereich von 180 bis 21O0C oder hochsiedende Gemische von aromatischen und aliphatischen Kohlenwasserstoffen mit einem Siedebereich von 180 bis 2200C und/oder Spindeöl und/oder Monochlornaphthalin, vorzugsweise α-Monochlornaphthalin, verwendet.In a preferred embodiment, liquid aliphatic hydrocarbons having a boiling range from 180 to 21O 0 C or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 220 0 C and / or spindle oil and / or monochloronaphthalene, preferably α-monochloronaphthalene used.
Die organischen schwerflüchtigen öligen oder ölartigen Lösungsmittel mit einer Verdunstungszahl über 35 und einem Flammpunkt oberhalb 3O0C, vorzugsweise oberhalb 450C, können teilweise durch leicht oder mittelflüchtige organisch-chemische Lösungsmittel ersetzt werden, mit der Maßgabe, daß das Lösungsmittelgemisch ebenfalls eine Verdunstungszahl über 35 und einen Flammpunkt oberhalb 300C, vorzugsweise oberhalb 45°C, aufweist und daß das Insektizid- Fungizid-Gemisch in diesem Lösungsmittelgemisch löslich oder emulgierbar ist.The organic semi-volatile oily or oily solvents having an evaporation number above 35 and a flash point above 30 0 C, preferably above 45 0 C, can be partially replaced by light or medium volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 0 C, preferably above 45 ° C, and that the insecticide-fungicide mixture in this solvent mixture is soluble or emulsifiable.
Nach einer bevorzugten Ausführungsform wird ein Teil des organisch-chemischen Lösungsmittel oder Lösungsmittelgemisches oder ein aliphatisches polares organisch-chemisches Lösungsmittel oder Lösungsmittelgemisch ersetzt. Vorzugsweise gelangen Hydroxyl- und/oder Ester- und/oder Ethergruppen enthaltende aliphatische organisch-chemische Lösungsmittel wie beispielsweise Glycolether, Ester oder dgl. zur Anwendung.According to a preferred embodiment, a part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture replaced. Preferably, aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups are used, for example glycol ethers, esters or the like.
Als organisch-chemische Bindemittel werden im Rahmen der vorliegenden Erfindung die an sich bekannten wasserverdünnbaren und/oder in den eingesetzten organisch-chemischen Lösungsmitteln löslichen oder dispergier- bzw. emulgierbaren Kunstharze und/oder bindende trocknende Öle, insbesondere Bindemittel bestehend aus oder enthaltend ein Acrylatharz, ein Vinylharz, z.B. Polyvinylacetat, Polyesterharz, Polykondensations- oder Polyadditionsharz, Polyurethanharz, Alkydharz bzw. modifiziertes Alkydharz, Phenolharz, Kohlenwasserstoffharz wie Inden-Cumaronharz, Siliconharz, trocknende pflanzliche und/oder trocknende Öle und/oder physikalisch trocknende Bindemittel auf der Basis eines Natur- und/oder Kunstharzes verwendet.In the context of the present invention, organic-chemical binders are the water-dilutable and / or soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils used in the organic-chemical solvents used, in particular binders consisting of or containing an acrylate resin, a vinyl resin, eg Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene cumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.
Das als Bindemittel verwendete Kunstharz kann in Form einer Emulsion, Dispersion oder Lösung, eingesetzt werden. Als Bindemittel können auch Bitumen oder bituminöse Substanzen bis zu 10 Gew.-%, verwendet werden. Zusätzlich können an sich bekannte Farbstoffe, Pigmente, wasserabweisende Mittel, Geruchskorrigentien und Inhibitoren bzw. Korrosionsscftutzmittel und dgl. eingesetzt werden.The synthetic resin used as the binder may 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 repellents, odor correctors and inhibitors or corrosion scavengers and the like can be used.
Bevor .zugt is Vt gemäß der Erfindung als organisch-chemische Bindemittel mindestens ein Alkydharz bzw. modifiziertes Alkydharz und/oder ein trocknendes pflanzliches Öl im Mittel oder im Konzentrat enthalten. Bevorzugt werden gemäß der Erfindung Alkydharze mit einem Ölgehalt von mehr als 45 Gew.-%, vorzugsweise 50 bis 68 Gew.-%, verwendet.Before. Vt is according to the invention as organic-chemical binder at least one alkyd resin or modified alkyd resin and / or a drying vegetable oil in the middle or in the concentrate. Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
Das erwähnte Bindemittel kann ganz oder teilweise durch ein Fixierungsmittel(gemisch) oder ein Weichmacher(gemisch) ersetzt werden. Diese Zusätze sollen einer Verflüchtigung der Wirkstoffe sowie einer Kristallisation bzw. Ausfällem vorbeugen. Vorzugsweise ersetzen sie 0,01 bis 30 % des Bindemittels (bezogen auf 100 % des eingesetzten Bindemittels).The mentioned binder can be completely or partially replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. Preferably, they replace 0.01 to 30% of the binder (based on 100% of the binder used).
Die Weichmacher stammen aus den chemischen Klassen der Phthalsäureester wie Dibutyl-, Dioctyl- oder Benzylbutylphthalat, Phosphorsäureester wie Tributylphosphat, Adipinsäureester wie Di-(2-ethylhexyl)-adipat, Stearate wie Butylstearat oder Amylstearat, Oleate wie Butyloleat, Glycerinether oder höhermolekulare Glykoiether, Glycerinester sowie p-Toluolsulfonsäureester.The plasticizers are derived from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric 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, glycerol ethers or higher molecular weight glyco-ethers, glycerol esters and p-toluenesulfonic acid ester.
Fixierungsmittel basieren chemisch auf Polyvinylalkylethern wie z.B. Polyvinylmethylether oder Ketonen wie Benzophenon, Ethylenbenzophenon.Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
Als Lösungs- bzw. Verdünnungsmittel kommt insbesondere auch Wasser in Frage, gegebenenfalls in Mischung mit einem oder mehreren der oben genannten organisch-chemischen Lösungs- bzw. Verdünnungsmittel, Emulgatoren und Dispergatoren. Ein besonders effektiver Holzschutz wird durch großtechnische Imprägnierverfahren, z.B. Vakuum, Doppelvakuum oder Druckverfahren, erzielt.Particularly suitable solvents or diluents are also water, optionally in admixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants. A particularly effective wood protection is achieved by large-scale impregnation, eg vacuum, double vacuum or printing process.
Die anwendungsfertigen Mittel können gegebenenfalls noch weitere Insektizide und gegebenenfalls noch ein oder mehrere Fungizide enthalten.The ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
Als zusätzliche Zumischpartner kommen vorzugsweise die in der WO 94/29 268 genannten Insektizide und Fungizide in Frage. Die in diesem Dokument genannten Verbindungen sind ausdrücklicher Bestandteil der vorliegenden Anmeldung.As additional Zumischpartner preferably come in WO 94/29 268 mentioned insecticides and fungicides in question. The compounds mentioned in this document form an integral part of the present application.
Als ganz besonders bevorzugte Zumischpartner können Insektizide, wie Chlorpyriphos, Phoxim, Silafluofm, Alphamethrin, Cyfluthrin, Cypermethrin, Deltarnethrin, Permethrih, Imidäcloprid, NI- 25, Flufenoxuron, Hexaflumuron, Transfluthrin, Thiacloprid, Methoxyfenozide ,Triflumuron, Clothianidin, Spinosad, Tefluthrin,Particularly preferred admixing partners may be insecticides such as chlorpyriphos, phoxim, silafluofm, alphamethrin, cyfluthrin, cypermethrin, deltarnethrine, permethrih, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozide, triflumuron, clothianidin, spinosad, tefluthrin,
sowie Fungizide wie Epoxyconazole, Hexaconazole, Azaconazole, Propiconazole, Tebuconazole, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-Iod-2-propinyl- butylcarbamat, N-Octyl-isothiazolin-3-on und 4,5-Dichlor-N-octylisothiazolin-3-on, sein. n.and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluid, tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N octylisothiazolin-3-one. n.
Zugleich körnen die erfϊndungsgemäßen Verbindungen zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, eingesetzt werden.At the same time, the compounds according to the invention can be used to protect against the growth of objects, in particular hulls, sieves, nets, structures, wharfages and signal systems, which come into contact with seawater or brackish water.
Bewuchs durch sessile Oligochaeten, wie Kalkrölirenwüπner sowie durch Muscheln und Arten der Gruppe Ledamorpha (Entenmuscheln), wie verschiedene Lepas- und Scalpellum-Arten, oder durch Arten der Gruppe Balanomorpha (Seepocken), wie Baianus- oder Pollicipes-Species, erhöht den Reibungswiderstand von Schiffen und führt in der Folge durch erhöhten Energieverbrauch und darüber hinaus durch häufige Trockendockaufenthalte zu einer deutlichen Steigerung der Betriebskosten.The growth of sessile oligochaetes, such as calcareous owls, as well as mussels and species of the group Ledamorpha (barnacles), such as various Lepas and scalpel species, or species of the group Balanomorpha (barnacles), such as Baianus or Pollicipes species, increases the frictional resistance of As a result of increased energy consumption and, moreover, frequent drydocking periods, the operating costs are significantly increased.
Neben dem Bewuchs durch Algen, beispielsweise Ectocarpus sp. und Ceramium sp., kommt insbesondere dem Bewuchs durch sessile Entomostraken-Gruppen, welche unter dem Namen Cirripedia (Rankenflußkrebse) zusammengefaßt werden, besondere Bedeutung zu.In addition to the vegetation by algae, for example Ectocarpus sp. and Ceramium sp., is particularly the fouling by sessile Entomostraken groups, which are summarized under the name Cirripedia (cirripeds), particular importance.
Es wurde nun überraschenderweise gefunden, daß die erfmdungsgemäßen Verbindungen allein oder in Kombination mit anderen Wirkstoffen, eine hervorragende Antifouling (Antibewuchs)- Wirkung aufweisen.It has now surprisingly been found that the compounds according to the invention, alone or in combination with other active ingredients, have an outstanding antifouling (anti-fouling) action.
Durch Einsatz von erfϊndungsgemäßen Verbindungen allein oder in Kombination mit anderen Wirkstoffen, kann auf den Einsatz von Schwermetallen wie z.B. in Bis(trialkylzinn)-sulfiden, Tri- 7j-butylzinnlaurat, Tri-w-butylzinnchlorid, Kupfer(I)-oxid, Triethylzinnchlorid, Tri-rc-butyl(2- phenyl-4-chlorphenoxy)-zinn, Tributylzinnoxid, Molybdändisulfid, Antimonoxid, polymerem Butyltitanat, Phenyl-(bispyridin)-wismutchlorid, Tri-n-butylzinnfiuorid, Manganethylenbisthio- carbamat, Zinkdimethyldithiocarbamat, Zinkethylenbisthiocarbamat, Zink- und Kupfersalze von 2- Pyridinthiol-1-oxid, Bisdimethyldithiocarbamoylzinkethylenbisthiocarbamat, Zinkoxid, Kupfer(I)- ethylen-bisdithiocarbamat, Kupferthiocyanat, Kupfemaphthenat und Tributylzinnhalogeniden verzichtet werden oder die Konzentration dieser Verbindungen entscheidend reduziert werden.By using compounds according to the invention, alone or in combination with other active substances, it is possible to use heavy metals such as, for example, bis (trialkyltin) sulfides, tri-7-yl-tin tin laurate, tri-w-butyltin chloride, copper (I) oxide, triethyltin chloride, Tri-rc-butyl (2- phenyl-4-chlorophenoxy) -tin, tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, manganese ethylene bis-carbamate, zinc dimethyldithiocarbamate, zinc ethylene bis-thiocarbamate, zinc and copper salts of 2-pyridinethiol-1 oxide, bisdimethyldithiocarbamoylzinc ethylene bis-thiocarbamate, zinc oxide, copper (I) ethylene bisdithiocarbamate, copper thiocyanate, copper naphthenate and tributyltin halides, or the concentration of these compounds can be decisively reduced.
Die anwendungsfertigen Antifoulingfarben können gegebenenfalls noch andere Wirkstoffe, vorzugsweise Algizide, Fungizide, Herbizide, Molluskizide bzw. andere Antifouling-Wirkstoffe enthalten.The ready-to-use antifouling paints may optionally contain other active substances, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
Als Kombinationspartner für die erfindungsgemäßen Antifouling-Mittel eignen sich vorzugsweise:Suitable combination partners for the antifouling agents according to the invention are preferably:
Algizide wie 2-/ert.-Butylamino-4-cyclopropylamino-6-methylthio-l,3,5-triazin, Dichlorophen, Diuron, Endothal, Fentinacetat, Isoproturon, Methabenzthiazuron, Oxyfiuorfen, Quinoclamine und Terbutryn;Algicides such as 2- / tert-butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzothiazuron, oxyfiuorfen, quinoclamine and terbutryn;
Fungizide wie Benzo[έ]thiophencarbonsäurecyclohexylamid-S,S-dioxid, Dichlofluanid, Fluor- folpet, 3-ϊδd-2-propinyl-butylcarbamat, Tolylfluanid und Azole wie Azaconazole, Cyproconazole, Epoxyconazole'j Hexaconazole, Metconazole, Propiconazole und Tebuconazole;Fungicides such as benzo [έ] thiophenecarboxylic cyclohexylamide S, S-dioxide, dichlofluanid, fluoro folpet, 3-δd-2-propynyl-butylcarbamate, tolylfluanid and azoles such as azaconazoles, cyproconazoles, epoxyconazole'j hexaconazoles, metconazoles, propiconazoles and tebuconazoles;
Molluskizide wie Fentinacetat, Metaldehyd, Methiocarb, Niclosamid, Thiodicarb und Trimethacarb, Fe-chelate,Molluscicides such as fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb, Fe-chelates,
oder herkömmliche Antifouling-Wirkstoffe wie 4,5-Dichlor-2-octyl-4-isothiazolin-3-on, Diiod- methylparatrylsulfon, 2-(N,N-Dimethylthiocarbamoylthio)-5-nitrothiazyl, Kalium-, Kupfer-, Natrium- und Zinksalze von 2-Pyridinthiol-l-oxid, Pyridin-triphenylboran, Tetrabutyldistannoxan, 2,3,5, 6-Tetrachlor-4-(methylsulfonyl)-pyridin, 2,4,5,6-Tetrachloroisophthalonitril, Tetramethyl- thiuramdisulfid und 2,4,6-Trichlorphenylmaleinimid.or conventional antifouling agents such as 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulfone, 2- (N, N-dimethylthiocarbamoylthio) -5-nitrothiazyl, potassium, copper, sodium and zinc salts of 2-pyridinethiol-1-oxide, pyridine-triphenylborane, tetrabutyldistannoxane, 2,3,5,6-tetrachloro-4- (methylsulfonyl) -pyridine, 2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide and 2 , 4,6-Trichlorphenylmaleinimid.
Die verwendeten Antifouling-Mittel enthalten die erfϊndungsgemäßen Wirkstoff der erfindungsgemäßen Verbindungen in einer Konzentration von 0,001 bis 50 Gew.-%, insbesondere von 0,01 bis 20 Gew.-%.The antifouling agents used contain the erfϊndungsgemäßen active ingredient of the compounds of the invention in a concentration of 0.001 to 50 wt .-%, in particular from 0.01 to 20 wt .-%.
Die erfϊndungsgemäßen Antifouling-Mittel enthalten desweiteren die üblichen Bestandteile wie z.B. in Ungerer, Chem. Ind. 1985, 37, 730-732 und Williams, Antifouling Marine Coatings, Noyes, ParkRidge, 1973 beschrieben.The antifouling agents of the invention further contain the usual ingredients, e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
Antifouling-Anstrichmittel enthalten neben den algiziden, fungiziden, molluskiziden und erfindungsgemäßen insektiziden Wirkstoffen insbesondere Bindemittel. Beispiele für anerkannte Bindemittel sind Polyvinylchlorid in einem Lösungsmittelsystem, chlorierter Kautschuk in einem Lösungsmittelsystem, Acrylhärze in einem Lösungsmittelsystem insbesondere in einem wäßrigen System, Vinylchlorid/Vinylacetat-Copolymersysteme in Form wäßriger Dispersionen oder in Form von organischen Lösungsmittelsystemen, Buta- dien/Styrol/Acrylnitril-Kautschuke, trocknende Öle, wie Leinsamenöl, Harzester oder modifizierte Hartharze in Kombination mit Teer oder Bitumina, Asphalt sowie Epoxyverbindungen, geringe Mengen Chlorkautschuk, chloriertes Polypropylen und Vinylharze. . .Antifouling paints contain, in addition to the algicidal, fungicidal, molluscicidal and insecticidal active compounds according to the invention, in particular binders. Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resin 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, drying oils, such as linseed oil, rosin esters or modified hard resins in combination with tar or bitumens, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins. , ,
Gegebenenfalls enthalten Anstrichmittel auch anorganische Pigmente, organische Pigmente oder Farbstoffe, welche vorzugsweise in Seewasser unlöslich sind. Ferner können Anstrichmittel Materialien, wie Kolophonium enthalten, um eine gesteuerte Freisetzung der Wirkstoffe zu ermöglichen. Die Anstriche können ferner Weichmacher, die Theologischen Eigenschaften beeinflussende Modifizierungsmittel sowie andere herkömmliche Bestandteile enthalten. Auch in Self-Polishing-Antifouling-Systemen können die erfindungsgemäßen Verbindungen oder die oben genannten Mischungen eingearbeitet werden.Optionally, paints also contain inorganic pigments, organic pigments or dyes which are preferably insoluble in seawater. Further, paints may contain materials such as rosin to allow for controlled release of the active ingredients. The paints may further contain plasticizers, rheology modifiers, and other conventional ingredients. Also in self-polishing antifouling systems, the compounds of the invention or the above-mentioned mixtures can be incorporated.
Die Wirkstoffe eignen sich auch zur Bekämpfung von tierischen Schädlingen, insbesondere von und Milben, die in geschlossenen Räumen, wie beispielsweise Büros, Fahrzeugkabinen u.a. vorkommen. Sie. können zur Bekämpfung dieser Schädlinge allein oder in Kombination mit anderen Wirk- und Hilfsstoffen in Haushaltsinsektizid-Produkten verwendet werden. Sie sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam. Zu diesen Schädlingen gehören:The active compounds are also suitable for controlling animal pests, in particular of and mites, which occur in enclosed spaces, such as, for example, offices, vehicle cabins and the like. She. can fight these pests are used alone or in combination with other agents and excipients in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
Aus der Ordnung der Scorpionidea z.B. Buthus occitanus.From the order of Scorpionidea e.g. Buthus occitanus.
Aus der Ordnung der Acarina z.B. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.From the order of Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
Aus der Ordnung der Araneae z.B. Aviculariidae, Araneidae.From the order of the Araneae e.g. Aviculariidae, Araneidae.
Aus der Ordnung der Opiliones z.B. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.From the order of Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
Aus der Ordnung der Isopoda z.B. Oniscus asellus, Porcellio scaber.From the order of isopods e.g. Oniscus asellus, Porcellio scaber.
Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus, Polydesmus spp..From the order of diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
Aus der Ordnung der Chilopoda z.B. Geophilus spp.. Aus der Ordnung der Zygentoma z.B. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.From the order of Chilopoda eg Geophilus spp .. From the order of Zygentoma eg Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
Aus der Ordnung der Blattaria z.B. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.From the order of the Blattaria e.g. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
Aus der Ordnung der Saltatoria z.B. Acheta domesticus.From the order of Saltatoria e.g. Acheta domesticus.
Aus der Ordnung der Dermaptera z.B. Forficula auricularia.From the order of the Dermaptera e.g. Forficula auricularia.
Aus der Ordnung der Isoptera z.B. Kalotermes spp., Reticulitermes spp.From the order of Isoptera e.g. Kalotermes spp., Reticulitermes spp.
Aus der Ordnung der Psocoptera z.B. Lepinatus spp., Liposcelis spp.From the order of Psocoptera e.g. Lepinatus spp., Liposcelis spp.
Aus der Ordnung der Coleoptera z.B. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dbminica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.From the order of Coleoptera e.g. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dbminica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
Aus der Öjdnung der Diptera z.B. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles sppft, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans, Tipula paludosa.From the statement of the Diptera, e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys calcitrans , Tipula paludosa.
Aus der Ordnung der Lepidoptera z.B. Achroia grisella, Galleria mellonella, Plodia inteφunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.From the order of Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inteφunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
Aus der Ordnung der Siphonaptera z.B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.From the order of siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
Aus der Ordnung der Hymenoptera z.B. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.From the order of Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
Aus der Ordnung der Anoplura z.B. Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.From the order of the Anoplura e.g. Pediculus humanus capitis, Pediculus humanus corporis, Phthirus pubis.
Aus der Ordnung der Heteroptera z.B. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.From the order of Heteroptera, e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
Die Anwendung im Bereich der Haushaltsinsektizide erfolgt allein oder in Kombination mit anderen geeigneten Wirkstoffen wie Phosphorsäureestera, Carbamaten, Pyrethroiden, Neo- nicotinoiden, Wachstumsregulatoren oder Wirkstoffen aus anderen bekannten Insektizidklassen. Die Anwendung erfolgt in Aerosolen, drucklosen Sprühmitteln, z.B. Pump- und Zerstäubersprays, Nebelautomaten, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen. 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, neonicotinoids, growth regulators or active compounds from other known classes of insecticides. It is used in aerosols, pressureless sprays, eg pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in straw baits or bait stations.
Herstellungsbeispiele:Preparation Examples:
Beispiel 1example 1
0.305 g (7.63 mmol) Natriumhydrid (60% in Öl) werden bei Raumtemperatur (200C) in 35 ml Tetrahydrofiiran vorgelegt, eine Lösung von 0.36 g (5.09 mmol) 2-Butin-l-ol in 15 ml Tetrahydrofuran wird tropfenweise dazu gegeben und die Mischung wird 30 Minuten gerührt. Anschließend wird unter Eisbadkühlung eine Lösung von 1.0 g 4-Chlor-6-(3-thienyl)-pvrirnidin in 10 ml Tetrahydrofuran zugetropft und die Mischung wird 12 Stunden nachgerührt. Zur Aufarbeitung wird zwischen gesättigter Ammoniumchloridlösung und Methyl-t-butylether verteilt, die organische Phase getrocknet, unter vermindertem Druck eingeengt und säulenchromato- graphisch weiter aufgereinigt (Kieselgel RP-18, Gradient Acetonitril-Wasser).0.305 g (7.63 mmol) of sodium hydride (60% in oil) are introduced at room temperature (20 0 C) in 35 ml Tetrahydrofiiran, a solution of 0.36 g (5:09 mmol) of 2-butyn-l-ol in 15 ml of tetrahydrofuran is added dropwise thereto and the mixture is stirred for 30 minutes. Subsequently, a solution of 1.0 g of 4-chloro-6- (3-thienyl) -pvrirnidin in 10 ml of tetrahydrofuran is added dropwise with ice bath cooling and the mixture is stirred for 12 hours. For working up, the mixture is partitioned between saturated ammonium chloride solution and methyl t-butyl ether, the organic phase is dried, concentrated under reduced pressure and further purified by column chromatography (silica gel RP-18, gradient acetonitrile-water).
Man erhält 0.5 g (40 % der Theorie) 4-(2-Butin-l-yl-oxy)-6-(3-thienyl)-pyrimidin0.5 g (40% of theory) of 4- (2-butyn-1-yl-oxy) -6- (3-thienyl) -pyrimidine is obtained
log P 2.84log P 2.84
Beispiel 2:Example 2:
0.50 g (2.738 mmol) 4-Chlor-6-(2-butin-l-yl-oxy)-pyrimidin, 0.381 g (2.738 mmol) 4-Chlor- pyrazol-hydrochlorid und 1.963 g (6.024 mmol) Cäsiumcarbonat werden 12 Stunden in Acetonitril unter Rückfluss erhitzt. Zur Aufarbeitung wird 2wischen wässriger Citronen- säurelösung und Dichlormethan verteilt, die organische Phase getrocknet, unter vermindertem Druck eingeengt und säulenchromatographisch weiter aufgereinigt (zuerst Kieselgel, Gradient Cyclohexan-Essigester, anschliessend Kieselgel RP-18, Gradient Acetonitril-Wasser).0.50 g (2.738 mmol) of 4-chloro-6- (2-butyn-1-yl-oxy) -pyrimidine, 0.381 g (2.738 mmol) of 4-chloro-pyrazole hydrochloride and 1963 g (6.024 mmol) of cesium carbonate are allowed to react for 12 hours heated under reflux in acetonitrile. For working up, it is partitioned between aqueous citric acid solution and dichloromethane, the organic phase is dried, concentrated under reduced pressure and further purified by column chromatography (first silica gel, gradient cyclohexane-ethyl acetate, then silica gel RP-18, gradient acetonitrile-water).
Man erhält 0.369 g (54 % der Theorie) 4-Butinyloxy-6-(4-Chlor-pyrazol-l-yl)-pyrimidinThis gives 0.369 g (54% of theory) of 4-butynyloxy-6- (4-chloro-pyrazol-1-yl) -pyrimidine
logP 3.65logP 3.65
Analog zu den Beispielen 1 und 2 sowie entsprechend der allgemeinen Beschreibung der erfindungsgemäßen Herstellungsverfahren können beispielsweise auch die in der nachstehenden Tabelle 1 aufgeführten Verbindungen der Formel (I) hergestellt werden. Analogously to Examples 1 and 2 and according to the general description of the preparation process according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below.
Tabelle 1: Beispiele für die Verbindungen der Formel (I)Table 1: Examples of the compounds of the formula (I)
Die Bestimmung der in der Tabelle angegebenen logP-Werte erfolgte gemäß EEC-Directive 79/831 Annex V.A8 durch HPLC (High' Performance Liquid Chromatography) an einer Phasenumkehrsäule (C 18). Temperatur: 43°C.The determination indicated in the table logP values was performed according EEC Directive 79/831 Annex V.A8 by HPLC (High 'Performance Liquid Chromatography) on a reversed-phase column (C 18). Temperature: 43 ° C.
(a) Eluenten für die Bestimmung im sauren Bereich (pH 2,3): 0,1 % wässrige Phosphorsäure, Acetonitril; linearer Gradient von 10% Acetonitril bis 90 % Acetonitril - entsprechende Messergebnisse sind in Tabelle 1 mit a) markiert.(a) Eluents for acidic determination (pH 2.3): 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with a).
(b) Eluenten für die Bestimmung im neutralen Bereich (pH 7,5): 0,01-molare wässrige Phosphatpuffer-Lösung, Acetonitril; linearer Gradient von 10 % Acetonitril bis 90 % Acetonitril - entsprechende Messergebnisse sind in Tabelle 1 mit b) markiert. Die Eichung erfolgte mit unverzweigten Alkan-2-onen (mit 3 bis 16 Kohlenstoffatomen), deren logP-Werte bekannt sind (Bestimmung der logP-Werte anhand der Retentionszeiten durch lineare Interpolation zwischen zwei aufeinanderfolgenden Alkanonen).(b) Eluents for neutral determination (pH 7.5): 0.01 M aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with b). The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms), whose logP values are known (determination of the logP values by means of the retention times by linear interpolation between two consecutive alkanones).
Die lambda-max-Werte wurden an Hand der UV-Spektren von 200 nm bis 400 nm in den Maxima der chromatögraphischen Signale ermittelt. The lambda-max values were determined on the basis of the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.
Ausgangsstoffe der Formel (H):Starting materials of the formula (H):
Beispiel TII-I)Example TII-I)
1.49 g (10 mmol) 4,6-Dichlor-pyrimidin werden in 50 ml 1,2-Dimethoxy-ethan vorgelegt, unter Argon 1.54 g (12 mmol) 3-Thiophen-boronsäure und 0,69g (0.6 mmol) Tetrakis-(triphenyl- phosphin)palladium(O) dazu gegeben, die Mischung 15 Minuten gerührt, 50 ml 20%ige Natriumcarbonatlösung zugesetzt und die Mischung 4 Stunden bei 800C gerührt. Zur Aufarbeitung wird zwischen Citronensäurelösung und Dichlormethan verteilt, die organische Phase getrocknet und das Lösungsmittel unter vermindertem Druck sorgfältig abdestilliert.1.49 g (10 mmol) of 4,6-dichloropyrimidine are initially charged in 50 ml of 1,2-dimethoxyethane, 1.54 g (12 mmol) of 3-thiopheneboronic acid and 0.69 g (0.6 mmol) of tetrakis (under argon) triphenylphosphine) palladium (O) was added thereto, the mixture was stirred for 15 minutes, 50 ml of 20% strength sodium carbonate solution were added and the mixture was stirred at 80 ° C. for 4 hours. For workup, the mixture is partitioned between citric acid solution and dichloromethane, the organic phase is dried and the solvent is carefully distilled off under reduced pressure.
Man erhält 2.1 g (94 % der Theorie) 4-Chlor-6-(3-thienyl)-pyrimidinThis gives 2.1 g (94% of theory) of 4-chloro-6- (3-thienyl) -pyrimidine
logP 2.31 logP 2.31
Anwendungsbeispiele:Application examples:
Beispiel AExample A
Myzus-Test ( MYZUPE Spritzbehandlung)Myzus test (MYZUPE spray treatment)
Lösungsmittel: 78 Gewichtsteile Aceton 1,5 Gewichtsteile DimethylformamidSolvent: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide
Emulgator: 0,5 Gewichtsteile AlkylarylpolyglykoletherEmulsifier: 0.5 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Chinakohlblattscheiben (Brassica pekinensis), die von allen Stadien der Grünen Pfϊrsichblattlaus (Myzus persicae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt.Chinese cabbage leaf discs (Brassica pekinensis), which are infested by all stages of the green pepper aphid (Myzus persicae), are sprayed with an active compound preparation of the desired concentration.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden.After the desired time, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele gute Wirksamkeit: siehe TabelleIn this test, z. B. the following compounds of the preparation examples good activity: see table
Beispiel BExample B
Aphis gossypii -Test (APHIGO)Aphis gossypii test (APHIGO)
Lösungsmittel: 7 Gewichtsteile DimethylformamidSolvent: 7 parts by weight of dimethylformamide
Emulgator: . 2 Gewichtsteile AlkylarylpolyglykoletherEmulsifier:. 2 parts by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Baumwollblätter (Gossypium hirsutum), die stark von der Baumwollblattlaus (Aphis gossypii) befallen sind, werden durch Tauchen in die Wirkstoffzubereitung der gewünschten Konzentration behandelt.Cotton leaves (Gossypium hirsutum) which are heavily infested with the cotton aphid (Aphis gossypii) are treated by being dipped into the preparation of active compound of the desired concentration.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden.After the desired time the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigt z. B. die folgende Verbindung der Herstellungsbeispiele gute Wirksamkeit: siehe TabelleIn this test, z. B. the following compound of the preparation examples good activity: see table
Beispiel C Example C
Myzus-Test; oral (MYZUPE O)Myzus test; oral (MYZUPE O)
Lösungsmittel: 80 Gewichtsteile AcetonSolvent: 80 parts by weight of acetone
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and the concentrate is diluted with water to the desired concentration.
Gefäße werden mit allen Stadien der Grünen Pfirsichblattlaus (Myzus persicae) besetzt, durch saugen an der Wirkstoffzubereitung der gewünschten Konzentration wird behandelt.Vessels are filled with all stages of the Green Peach aphid (Myzus persicae), by sucking on the preparation of active compound of the desired concentration is treated.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden.After the desired time, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Test zeigt z. B. die folgende Verbindung der Herstellungsbeispiele gute Wirksamkeit: siehe TabelleIn this test, z. B. the following compound of the preparation examples good activity: see table
Beispiel DExample D
Myzus persicae (MYZUPE U)Myzus persicae (MYZUPE U)
Lösungsmittel: 1 % N-methylpyrolidon (NMP) 1 % DiacetonalkoholSolvent: 1% N-methylpyrolidone (NMP) 1% diacetone alcohol
Farbstoff: Brillantsulfoflavin zum Anfärben des WassersDye: Brillantsulfoflavin for staining the water
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man den Wirkstoff mit den angegebenen Mengen Lösungsmittel und verdünnt das Konzentrat mit angefärbtem Wasser auf die gewünschte Konzentration.To produce a suitable preparation of active compound, the active compound is mixed with the indicated amounts of solvent and the concentrate is diluted with stained water to the desired concentration.
Den Myzus persicae wird eine Wirkstoffzubereitung der gewünschten Konzentration zur. Aufnahme zur Verfügung gestellt.The Myzus persicae is an active compound preparation of the desired concentration for. Recording provided.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Blattläuse abgetötet wurden; 0 % bedeutet, dass keine Blattläuse abgetötet wurden.After the desired time, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
Bei diesem Cest zeigen z. B. die folgenden Verbindungen der Herstellungsbeispiele gute Wirksamkeit:In this cest z. B. the following compounds of the preparation examples good activity:

Claims

Patentansprüche claims
1. Verbindungen der Formel (I),1. Compounds of the formula (I)
in welcher in which
A für eine Einfachbindung oder für O (Sauerstoff), S (Schwefel), NH, N(Ci-C4- Alkyl), eine Carbonyl-Gruppierung (C=O) oder eine Oxyimino-gruppierung (C=N- O-R, wobei R für Wasserstoff oder Ci-C4-AIlCyI steht) oder für gegebenenfalls durch Hydroxy oder Halogen substituiertes, geradkettiges oder verzweigtes Alkandiyl mit 1 bis 4 Kohlenstoffatomen steht,A represents a single bond or O (oxygen), S (sulfur), NH, N (Ci-C 4 - alkyl), a carbonyl moiety (C = O) or oximino moiety (C = N-OR, wherein R is hydrogen or C 1 -C 4 -alkyl) or represents optionally hydroxyl- or halogen-substituted, straight-chain or branched alkanediyl having 1 to 4 carbon atoms,
R1 für gegebenenfalls durch Halogen substituiertes, geradkettiges oder verzweigtes Alkinyl mit 2 bis 10 Kohlenstoffatomen steht,R 1 represents optionally halogen-substituted, straight-chain or branched alkynyl having 2 to 10 carbon atoms,
R2 für Wasserstoff, Amino, Halogen oder durch Halogen substituiertes, geradkettiges oder verzweigtes Alkyl mit 1 bis 4 Kohlenstoffatomen steht,R 2 is hydrogen, amino, halogen or halogen-substituted, straight-chain or branched alkyl having 1 to 4 carbon atoms,
R3 für" Wasserstoff, Amino, Halogen oder gegebenenfalls durch Halogen substituiertes, geradkettiges oder verzweigtes Alkyl mit 1 bis 4 Kohlenstoffatomen steht, undR 3 represents " hydrogen, amino, halogen or optionally halogen-substituted, straight-chain or branched alkyl having 1 to 4 carbon atoms, and
R4 für eine monocyclische oder bicyclische, gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Halogen, durch jeweils gegebenenfalls durch Hydroxy, Cyano oder Halogen substituiertes Ci-C6- Alkyl, Ci-C6-Alkyl-carbonyl, Ci-C6-Alkoxy, Ci-C6-Alkoxy-carbonyl, Ci-C6- Alkylthio, Q-Cö-Alkylsulfinyl, Ci-C6-Alkylsulfonyl, Q-Ce-Alkylamino, C1-C6- Alkyl-aminocarbonyl, Di-(CrC6-Alkyl)-amino, Di-(CrC6-Alkyl)-amino-carbonyl oder Di-(Ci-C6-Alkyl)-amino-sulfonyl substituierte heteroaromatische Gruppierung mit bis zu 9 Kohlenstoffatomen und mindestens einem Heteroatom aus der Reihe N (Stickstoff, 1 bis 5 N-Atome), O (Sauerstoff, maximal 1 O-Atom), S (Schwefel, maximal 1 S-Atom) steht. R 4 is a monocyclic or bicyclic, optionally substituted by nitro, hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, in each case optionally substituted by hydroxy, cyano or halogen-substituted Ci-C 6 - alkyl, Ci-C 6 - alkyl-carbonyl, Ci-C 6 alkoxy, Ci-C 6 alkoxy-carbonyl, Ci-C 6 - alkylthio, QC ö alkylsulfinyl, Ci-C6 alkylsulfonyl, Q-Ce-alkylamino, C 1 -C 6 - Alkyl-aminocarbonyl, di- (C r C 6 alkyl) amino, di- (C r C 6 alkyl) -aminocarbonyl or di (Ci-C 6 alkyl) -amino-sulfonyl substituted heteroaromatic grouping with up to 9 carbon atoms and at least one heteroatom from the series N (nitrogen, 1 to 5 N atoms), O (oxygen, at most 1 O atom), S (sulfur, at most 1 S atom).
2. Verbindungen der Jbormel (1) gemäti Anspruch i, dadurcn gekennzeichnet, dass2. Compounds of Jbormel (1) according to claim i, dadurcn characterized in that
A für eine Einfachbindung oder für O (Sauerstoff), S (Schwefel), NH, N(Methyl), N(Ethyl), N(Propyl), eine Carbonyl-Gruppierung (C=O) oder eine Oxyirnino- gruppierung (C=N-O-R, wobei R für Wasserstoff, Methyl oder Ethyl steht) oder für gegebenenfalls durch Hydroxy, Fluor oder Chlor substituiertes, geradkettiges oder verzweigtes Alkandiyl mit 1 bis 3 Kohlenstoffatomen steht,A stands for a single bond or for O (oxygen), S (sulfur), NH, N (methyl), N (ethyl), N (propyl), a carbonyl group (C = O) or an oxyirnino group (C = NOR, where R is hydrogen, methyl or ethyl) or represents optionally hydroxyl, fluorine or chlorine-substituted, straight-chain or branched alkanediyl having 1 to 3 carbon atoms,
R1 für gegebenenfalls durch Fluor, Chlor, Brom oder Iod substituiertes, geradkettiges oder verzweigtes Alkinyl mit 3 bis 6 Kohlenstoffatomen steht,R 1 is optionally substituted by fluorine, chlorine, bromine or iodine, straight-chain or branched alkynyl having 3 to 6 carbon atoms,
R2 für Wasserstoff, Amino, Fluor, Chlor, Brom, Iod oder durch Fluor und/oder Chlor substituiertes, geradkettiges oder verzweigtes Alkyl mit 1 bis 3 Kohlenstoffatomen steht,R 2 is hydrogen, amino, fluorine, chlorine, bromine, iodine or fluorine- and / or chlorine-substituted, straight-chain or branched alkyl having 1 to 3 carbon atoms,
R3 für Wasserstoff, Amino, Fluor, Chlor, Brom, Iod oder gegebenenfalls durch Fluor und/oder Chlor substituiertes, geradkettiges oder verzweigtes Alkyl mit 1 bis 3 Kohlenstoffatomen steht,R 3 is hydrogen, amino, fluorine, chlorine, bromine, iodine or optionally fluorine- and / or chlorine-substituted, straight-chain or branched alkyl having 1 to 3 carbon atoms,
R4K für eine monocyclische oder bicyclische, gegebenenfalls durch Nitro, Hydroxy, 'ϊ- Mercapto, Amino, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Iod, durch jeweils gegebenenfalls durch Hydroxy, Cyano, Fluor, Chlor oder Brom substituiertes Ci-C5-Alkyl, Ci-C5-Alkyl-carbonyl, Ci-C5-Alkoxy, Ci-C5- Alk'oxy-carbonyl, CrC5-Alkylthio, Q-Cs-Alkylsulfinyl, CrC5-Alkylsulfonyl, Q- C5-Alkylamino, CrCs-Alkyl-aminocarbonyl, Di-(C i-C5-Alkyl)-amino, Di-(Ci-C5- Alkyl)-amino-carbonyl oder Di-(Ci -C5-Alkyl)-amino-sulfonyl substituierte heteroaromatische Gruppierung mit bis zu 9 Kohlenstoffatomen und mindestens einem Heteroatom aus der Reihe N (Stickstoff, 1 bis 5 N-Atome), O (Sauerstoff, maximal 1 O-Atom), S (Schwefel, maximal 1 S-Atom) steht.R 4 K is a monocyclic or bicyclic, optionally substituted by nitro, hydroxy, ' ϊ-mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluoro, chloro, bromo, iodo, each optionally substituted by hydroxy, cyano, fluoro, chloro or bromine-substituted Ci-C 5 alkyl, Ci-C 5 alkyl-carbonyl, Ci-C 5 alkoxy, C 5 - Alk 'oxy-carbonyl, C r C 5 alkylthio, Q-Cs-alkylsulfinyl, C r C 5 alkylsulfonyl, Q-C 5 alkylamino, CRCS-alkyl-aminocarbonyl, di- (C iC 5 alkyl) amino, di (Ci-C 5 - alkyl) amino-carbonyl or di- (C C 5 alkyl) -amino-sulfonyl-substituted heteroaromatic grouping having up to 9 carbon atoms and at least one heteroatom from the series N (nitrogen, 1 to 5 N atoms), O (oxygen, at most 1 O atom), S ( Sulfur, a maximum of 1 S atom).
3. Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeiclinet, dass3. Compounds of formula (I) according to claim 1, characterized gekennzeiclinet that
A für eine Einfachbindung oder für O (Sauerstoff), S (Schwefel), NH, N(Methyl) oder für Methylen, Ethan-l,l-diyl (Ethyliden) oder Ethan-l,2-diyl (Dimethylen) steht,A is a single bond or O (oxygen), S (sulfur), NH, N (methyl) or methylene, ethane-1, l-diyl (ethylidene) or ethane-l, 2-diyl (dimethylene),
R1 für gegebenenfalls durch Fluor, Chlor, Brom oder Iod substituiertes 2-Propin-l-yl, 2-Butin-l-yl, 3-Butin-2-yl oder 2-Pentin-l-yl steht,R 1 is optionally substituted by fluorine, chlorine, bromine or iodine substituted 2-propyn-l-yl, 2-butyn-1-yl, 3-butyn-2-yl or 2-pentin-l-yl,
R2 für Wasserstoff, Fluor, Chlor, Brom oder durch Fluor und/oder Chlor substituiertes Methyl steht, R3 für Wasserstoff, Fluor, Chlor, Brom oder gegebenenfalls durch Fluor und/oder Chlor substituiertes Methyl steht,R 2 is hydrogen, fluorine, chlorine, bromine or methyl substituted by fluorine and / or chlorine, R 3 is hydrogen, fluorine, chlorine, bromine or methyl optionally substituted by fluorine and / or chlorine,
R4 für eine monocyclische, gegebenenfalls durch Nitro, Hydroxy, Mercapto, Amino, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, Iod, durch jeweils gegebenenfalls durch Hydroxy, Cyano, Fluor oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t-Butyl, Acetyl, Propionyl, n- oder i- Butyroyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxy- carbonyl, n- oder i-Propoxycarbonyl, n-, i-, s- oder t-Butoxycarbonyl, Methylthio, Ethylthio, n- oder- i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, n-,:i-, s- oder t- Butylamino, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylamino- carbonyl, Dimethylamino, Diethylamino,Dimethylaminocarbonyl, Diethylamino- carbonyl, Dimethylaminosulfonyl oder Diethylaminosulfonyl substituierte heteroaromatische Gruppierung aus der Reihe Furyl, Thienyl, Pyrrolyl, Pyrazolyl, Imidazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadia- zolyl, Triazolyl, Pyridinyl, Pyrimidinyl, Pyrazinyl, Pyridazinyl, Triazinyl steht.R 4 is a monocyclic, optionally substituted by nitro, hydroxy, mercapto, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, each optionally substituted by hydroxy, cyano, fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i Propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, : i-, s- or t-butylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl-substituted heteroaromatic grouping from the series furyl, thienyl, pyrrolyl, pyrazolyl , Imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazoly 1, oxadiazolyl, thiadiazolyl, triazolyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl.
4. Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet, dass4. Compounds of formula (I) according to claim 1, characterized in that
A für eine Einfachbindung oder für O (Sauerstoff), S (Schwefel), NH, N(Methyl) oder Methylen steht,A is a single bond or O (oxygen), S (sulfur), NH, N (methyl) or methylene,
R1 für 2-Propin-l-yl, 2-Butin-l-yl oder 2-Pentin-l-yl steht,R 1 is 2-propyn-1-yl, 2-butyn-1-yl or 2-pentyne-1-yl,
R2 für Wasserstoff steht,R 2 is hydrogen,
R3 für Wasserstoff, Fluor, Chlor oder Methyl steht,R 3 is hydrogen, fluorine, chlorine or methyl,
R4 für eine monocyclische gegebenenfalls durch Nitro, Cyano, Carboxy, Carbamoyl, Thiocarbamoyl, Fluor, Chlor, Brom, durch jeweils gegebenenfalls durch Cyano, Fluor oder Chlor substituiertes Methyl, Ethyl, n- oder i-Propyl, n-, i-, s- oder t- Butyl, Acetyl, Propionyl, n- oder i-Butyroyl, Methoxy, Ethoxy, n- oder i-Propoxy, Methoxycarbonyl, Ethoxycarbonyl, n- oder i-Propoxycarbonyl, Methylthio, Ethylthio, n- oder i-Propylthio, Methylsulfinyl, Ethylsulfinyl, Methylsulfonyl, Ethylsulfonyl, Methylamino, Ethylamino, n- oder i-Propylamino, Methylaminocarbonyl, Ethylaminocarbonyl, n- oder i-Propylaminocarbonyl, Dimethylamino, Diethylamino, Dimethylaminocarbonyl oder Dimethylaminosulfonyl substituierte heteroaromatische Gruppierung aus der Reihe Furyl, Thienyl, Pyrrolyl, Pyrazolyl, Imidazolyl, Oxazolyl, Isoxazolyl, Thiazolyl, Isothiazolyl, Oxadiazolyl, Thiadiazolyl, Triazolyl, Pyridinyl, Pyrimidinyl, Pyrazinyl, JPyridazinyl, Triazinyl steht.R 4 is a monocyclic optionally substituted by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, in each case optionally substituted by cyano, fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio , Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino, diethylamino, dimethylaminocarbonyl or dimethylaminosulfonyl-substituted heteroaromatic grouping from the series furyl, thienyl, pyrrolyl, Pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, Thiadiazolyl, triazolyl, pyridinyl, pyrimidinyl, pyrazinyl, JPyridazinyl, triazinyl.
5. Verfahren zum Herstellen von Verbindungen der Formel (I) gemäß Anspruch 1, dadurch gekennzeichnet,5. A process for preparing compounds of the formula (I) according to claim 1, characterized in that
a) dass man reaktive Pyrimidine der Formel (It)a) that reactive pyrimidines of the formula (It)
in welcherin which
X1 für Halogen oder Q-C^Alkylsulfonyl steht,X 1 is halogen or Q C 1-4 alkylsulfonyl,
mit Alkinolen der Formel (HI)with alkynols of the formula (HI)
- oder mit Alkalimetallsalzen hiervon gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls . in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt, oder- or with alkali metal salts thereof, optionally in the presence of one or more reaction auxiliaries and optionally. in the presence of one or more diluents, or
b) dass man reaktive Pyrimidine der Formel (IV)b) that reactive pyrimidines of the formula (IV)
in welcherin which
X2 für Halogen oder C1-C4-Alkylsulfonyl steht,X 2 is halogen or C 1 -C 4 -alkylsulfonyl,
mit nucleophilen Verbindungen der Formel (V) H-Λ-R4 A (V)with nucleophilic compounds of the formula (V) H - R4 A (V)
- oder mit Alkalimetallsalzen hiervon -or with alkali metal salts thereof -
gegebenenfalls in Gegenwart eines oder mehrerer Reaktionshilfsmittel und gegebenenfalls in Gegenwart eines oder mehrerer Verdünnungsmittel umsetzt.if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents.
6. Mittel, gekennzeichnet durch einen Gehalt von mindestens einer Verbindung der Formel (I) gemäß Anspruch 1 und üblichen Streckmitteln und/oder oberflächenaktiven Substanzen.6. agent, characterized by a content of at least one compound of formula (I) according to claim 1 and conventional extenders and / or surface-active substances.
7. Verfahren zum Bekämpfen von Schädlingen, dadurch gekennzeichnet, dass man eine Verbindung der Formel (I) gemäß Anspruch 1 oder ein Mittel gemäß Anspruch 6 auf die Schädlinge und/oder ihren Lebensraum einwirken lässt.7. A method for controlling pests, which comprises allowing a compound of formula (I) according to claim 1 or an agent according to claim 6 to act on the pests and / or their habitat.
8. Verwendung von Verbindungen der Formel (I) gemäß Anspruch 1 oder von »Mitteln gemäß Anspruch 6 zum Bekämpfen von Schädlingen. 8. Use of compounds of the formula (I) according to claim 1 or of »agents according to claim 6 for combating pests.
EP05821899A 2005-01-05 2005-12-24 Alkinyl-oxypyrimidine used in the form of pesticides Withdrawn EP1846398A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102005000747A DE102005000747A1 (en) 2005-01-05 2005-01-05 Substituted pyrimidines
PCT/EP2005/014033 WO2006072426A1 (en) 2005-01-05 2005-12-24 Alkinyl-oxypyrimidine used in the form of pesticides

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WO2010045377A2 (en) * 2008-10-14 2010-04-22 University Of Tennessee Research Foundation, The Pyrimidine non-classical cannabinoid compounds and related methods of use
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JP2012102089A (en) * 2010-10-15 2012-05-31 Sumitomo Chemical Co Ltd Pyrimidine compound and use thereof for harmful organism control
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DE102005000747A1 (en) 2006-07-13
KR20070098901A (en) 2007-10-05
CN101137649A (en) 2008-03-05
BRPI0519578A2 (en) 2009-02-17
US20090005403A1 (en) 2009-01-01
JP2008526793A (en) 2008-07-24

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