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WO2005065453A1 - Combinaisons de principes actifs a proprietes insecticides et acaricides - Google Patents

Combinaisons de principes actifs a proprietes insecticides et acaricides Download PDF

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Publication number
WO2005065453A1
WO2005065453A1 PCT/EP2004/014711 EP2004014711W WO2005065453A1 WO 2005065453 A1 WO2005065453 A1 WO 2005065453A1 EP 2004014711 W EP2004014711 W EP 2004014711W WO 2005065453 A1 WO2005065453 A1 WO 2005065453A1
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WIPO (PCT)
Prior art keywords
alkyl
alkoxy
halogen
spp
optionally
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PCT/EP2004/014711
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German (de)
English (en)
Inventor
Thomas Bretschneider
Reiner Fischer
Heike Hungenberg
Ernst BRÜCK
Anton Kraus
Wolfgang Thielert
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of WO2005065453A1 publication Critical patent/WO2005065453A1/fr
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring

Definitions

  • the present invention relates to new active ingredient combinations which consist of known tetronic acid derivatives and are very well suited for controlling animal pests such as insects and undesirable acarids.
  • the tetronic acid derivatives of the formula (I) are known compounds which are known from or are included in the following publications (cf. EP-A-528 156, EP-A-0 647 637, WO 95/26 345, WO 96/20 196, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 98/05 638, WO 98/25 928, WO 99 / 16 748, WO 99/43 649, WO 99/48 869, WO 99/55 673, WO 01/23 354 and WO 01/74 770).
  • the effectiveness of these compounds is good, but in some cases the range of effectiveness leaves something to be desired with low application rates.
  • X represents C i -C 6 alkyl, halogen, C 1 -C 6 alkoxy or C 1 -C 6 haloalkyl
  • Y represents hydrogen, Ci-Cg-alkyl, halogen, Ci-Cg-alkoxy or C1-C3-haloalkyl, t,
  • Z represents C 1 -Cg-alkyl, halogen or C -Cg-alkoxy
  • n stands for a number from 0-3,
  • A represents hydrogen or a straight-chain or branched one which is optionally substituted by halogen C ⁇ -Cg-polyalkoxy-C2-Cg-alkyl or C 1 -C 1 o-alkylthio-C 2 -Cg-alkyl or for cycloalkyl with 3-8 ring atoms, which can be interrupted by oxygen and / or sulfur or for each optionally phenyl or phenyl-C 1 -C 6 -alkyl which is substituted by halogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy or nitro, B represents hydrogen, C i -Cg-alkyl or C i -Cg-alkoxy-C -C -alkyl
  • a and B together with the carbon atom to which they are attached a saturated or unsaturated, optionally interrupted by oxygen and / or sulfur and optionally by halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy, C ⁇ -C4-haloalkyl , C 1 -C 4 haloalkoxy, C] ⁇ C 4 alkylthio or optionally substituted phenyl substituted or optionally benzo-fused 3- to 8-membered ring,
  • Rl for in each case optionally substituted by halogen C [ -C20-II, C2-C20-alkylene, C 1 -Cg -alkoxy-C 2 -Cg-alkyl, C 1 -Cg-alkylthio-C2-Cg-alkyl, C 1 -Cg-Polyalkoxy ⁇ -Cg- alkyl or cycloalkyl with 3-8 Rmgatoms, which can be interrupted by oxygen and / or sulfur atoms, represents optionally by halogen, nitro, C ⁇ -Cg-alkyl, C ⁇ -Cg- Alkoxy, C ⁇ -Cg-haloalkyl, Ci-Cg-haloalkoxy-substituted phenyl; represents optionally substituted by halogen, Ci-Cg-alkyl, C ⁇ -Cg-alkoxy, Ci-Cg-haloalkyl, Ci-Cg-haloalkoxy-
  • R 2 represents in each case optionally substituted by halogen C ⁇ -C20-al yl, C2-C20 "alkenyl, -C-Cg-alkoxy-C2-Cg-alkyl, -C-Cg-polyalkoxy-C 2 -Cg-alkyl, is phenyl or benzyl -C -alkyl, Ci-Cg-alkoxy, C j -Cg- substituted haloalkyl, - [; represents in each case optionally substituted by halogen, nitro, C
  • R 3 is optionally substituted by halogen C 1 -C 6 -alkyl, for each optionally by C 1 -C 4 alkyl, halogen, C 1 -C 4 haloalkyl, C ] ; -C 4 alkoxy, C 1 -C 4 haloalkoxy, nitro or Cyano substituted phenyl or benzyl,
  • R4 and R 5 independently of one another each represent C - Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg-alkylamino, di- (C 1 -C 8 ) -alkylamino, Ci-Cg-alkylthio, optionally substituted by halogen, C2- C5-alkenylthio, C2-C5-alkali ylthio, C3-C7-cycloalkylthio, for each optionally by halogen, nitro, cyano, -C-C4-alkoxy, C [-C4-haloalkoxy, C ] -C4-alkylthio, C ⁇ - C4-haloalkylthio, -CC-C4-alkyl, C; [- C4-haloalkyl substituted phenyl, phenoxy or phenylthio,
  • R 6 and R 7 are, independently of one another, in each case optionally substituted by halogen-substituted C - CiQ-Al l, C3-Cg-alkenyl, -C-Cg-alkoxy-C ⁇ -Cg-alkyl, for phenyl optionally substituted by halogen, Ci-Cg-haloalkyl, C ⁇ -Cg-alkyl or Cj-Cg-alkoxy, for optionally substituted by halogen, C ⁇ -Cg-alkyl, Ci-Cg-haloalkyl or Ci - Cg-alkoxy substituted benzyl or together represent an optionally interrupted by oxygen or sulfur 5- to 6-membered ring, which is optionally substituted by Ci -Cg-alkyl can be,
  • At least one further tetronic acid derivative of the formula (I) are synergistically active and are suitable for controlling animal pests.
  • the compounds of the formula (I) can be present in different compositions as geometric and / or optical isomers or isomer mixtures, which can optionally be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and agents containing them are the subject of the present invention. However, for the sake of simplicity, the following always refers to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • X represents C 1 -C 4 -alkyl, chlorine, bromine, C 1 -C 4 -alkoxy or trifluoromethyl
  • Y represents hydrogen, -CC 4 -alkyl, chlorine, bromine, C ⁇ -C4-alkoxy or -C-C 2 haloalkyl
  • Z represents C 1 -C 4 -alkyl, chlorine, bromine or C -C 4 -alkoxy
  • n 0 or 1
  • a and B together with the carbon atom to which they are attached form a saturated 5- to 6-membered ring which is optionally monosubstituted by C [-C4-alkyl or C; [- C4-alkoxy,
  • Rl for each optionally monosubstituted to trisubstituted by fluorine or chlorine, C 12 -C 12 alkyl, C 2 -C 12 alkenyl, C 1 -C 4 alkoxy-C 1 -C 2 -alkyl, or cycloalkyl having 3-6 ring atoms, that can be interrupted by 1 to 2 oxygen atoms, represents phenyl which is optionally simply substituted by fluorine, chlorine, bromine, nitro, C 1-4 alkyl, C 1-4 Al oxy, trifluoromethyl or trifluoromethoxy;
  • R 2 is in each case optionally substituted by halogen C 1 -C 6 -alkyl or C2-C; [ g-alkenyl, -C-Cg-alkoxy-C2-Cg-alkyl,
  • phenyl or benzyl optionally substituted by halogen, nitro, C 1 -C 4 -Al yl, C ] _-C4-Alko y or C 1 -C 4 -haloalkyl.
  • Active ingredient combinations are particularly preferred, the tetronic acid derivatives of the formulas (1-1) and (1-2) (1-1) (I-2)
  • the active ingredient combinations can also contain other fungicidal, acaricidal or insecticidal active components.
  • the active compounds are present in the active compound combinations according to the invention in certain weight ratios, the synergistic effect is particularly evident.
  • the weight ratios of the active ingredients in the active ingredient combinations can be varied within a relatively wide range.
  • the combinations according to the invention contain active compounds of the formula (I) in the preferred and particularly preferred mixing ratios given below.
  • the preferred mixing ratio is 10: 1 to 1:10.
  • the particularly preferred mixing ratio is 5: 1 to 1.5;
  • the mixing ratios are based on weight ratios. The relationship is to be understood as active ingredient 1 of formula (I) and active ingredient 2 of formula (I).
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
  • the active ingredient combinations can also contain other fungicidal, acaricidal or insecticidal active mixing partners.
  • the active compound combinations according to the invention in combination with good plant tolerance and favorable mammalian toxicity and good environmental compatibility for controlling animal pests, preferably arthropods and nematodes, in particular insects and * arachnids, encountered in agriculture, animal health, in forests, in gardens and leisure facilities, stored products and Material protection as well as in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • animal pests preferably arthropods and nematodes, in particular insects and * arachnids, encountered in agriculture, animal health, in forests, in gardens and leisure facilities, stored products and Material protection as well as in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanura e.g. Lepisma saccharina.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp.
  • Linognathus spp. Trichodectes spp., Damalinia spp. From the order of the Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci, Thrips palmi,
  • Homoptera for example Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.
  • Pemphigus spp . Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae s, Pseudococcuspp.
  • Otiorrhynchus sulcatus Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Scorpio maurus Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus sppus, Hemitars. Brevipalpus spp.
  • 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., Bursaph.
  • the active compound combinations according to the invention are particularly suitable for controlling “biting” pests. These include in particular the following pests:
  • the active compound combinations according to the invention are furthermore particularly suitable for controlling “sucking” pests. These include in particular the following pests:
  • From the order of the Homoptera for example 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, Laodetellapiaelapiaelapiaelapiaelapiaelapiaelapiaelapia, Lecanium corn lugens, Aonidiella aurantii, Aspidiotus hederae
  • the active compound combinations according to the invention are distinguished in particular by an excellent action against caterpillars, beetle larvae, spider mites, aphids and leaf miners.
  • the active substance combinations according to the invention 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 very fine encapsulations in polymeric substances , ,
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents and / or solid carriers
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules are possible: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; Possible emulsifiers and / or foam-generating agents are: for example nonionogenic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates,
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention can onnulleiteren in commercial f "and present in the prepared from these formulations, application forms as a mixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators or herbicides.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators or herbicides.
  • the insecticides include, for example organophosphate , Carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
  • the active compound combinations according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active substance combinations are notable for an excellent residual action on wood and clay and for good stability to alkali on limed substrates.
  • the active compound combinations according to the invention act not only against plant pests, hygiene pests and pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tortoise ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice and hair lice , Featherlings and fleas.
  • animal parasites ectoparasites
  • parasites include:
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota ., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Calliphora spp., Glossina spp.,
  • Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • Actinedida Prostigmata
  • Acaridida Acaridida
  • 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 compound combinations according to the invention are also suitable for combating arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • arthropods e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice.
  • the active compound combinations according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing , powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.
  • enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories
  • parenteral administration for example
  • the active compound combinations can be formulated (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10,000 - Apply a thinner or use it as a chemical bath.
  • insects may be mentioned by way of example and preferably, but without limitation: beetles such as
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • non-living materials such as preferably plastics, adhesives, glues, papers and cartons, leather, wood, wood processing products and paints.
  • the material to be protected from insect infestation is very particularly preferably wood and wood processing products.
  • Wood and wood processing products that can be protected by the agent according to the invention or mixtures containing it are to be understood as examples:
  • the active substance combinations 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 ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellants, optionally siccatives and UV stabilizers and, if appropriate Dyes and pigments and other processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimum amount of use can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and Like. Used.
  • the organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C. can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture is also a Evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the mixture is soluble or emulsifiable in this solvent mixture.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical agents are synthetic resins which are known to be water-dilutable and / or soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone 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, e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, diocyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate or glycerol ether higher molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, diocyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • stearates such as butyl ste
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved through large-scale impregnation processes, e.g. Vacuum, double vacuum or pressure process.
  • the active compound combinations according to the invention can be used to protect objects, in particular hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • Ledamorpha such as various types of Lepas and Scalpellum
  • Balanomorpha (barnacles) such as Baianus or Pollicipes species
  • heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-7 ⁇ -butyltin laurate, tri-ft-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, Antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-72-butyltin fluoride, manganese ethylene bisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinethiol-l-oxide, bisdimamethyldihydiamethyldihydiamethyldihydiamethyldihydiamethyldihydiamethyldihydiamethyld
  • the ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Algicides such as 2-tgrt.-butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and ter-butryn;
  • Fungicides such as benzo [ ⁇ ] thiophenecarboxylic acid cyclohexylamide-S, S-dioxide, dichlofluanide, fluorofolpet, 3-iodo-2-propynyl butyl carbamate, tolyl fluanide and azoles such as
  • conventional antifouling agents such as 4,5-dichloro-2
  • the antifouling agents used contain the active compound combinations according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.
  • the antifouling agents according to the invention furthermore contain the usual constituents as described, for example, in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, ' Park Ridge, 1973.
  • antifouling paints contain, in particular, agents.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile Rubbers, drying oils, such as linseed oil, resin esters or modified Hard resins in combination with tar or bitumen, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in sea water. Paints may also contain materials, such as rosin, to enable controlled release of the active ingredients.
  • the paints may also contain plasticizers, modifiers that affect the rheological properties, and other conventional ingredients.
  • the compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.
  • the active ingredient combinations are also suitable for combating animal pests, in particular insects, arachnids and mites, which live in closed rooms, such as apartments, factory halls, offices, vehicle cabins, etc. occurrence. They can be used to control these pests 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 oubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Isopoda e.g. Oniscus asellus, Porcellio scaber.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp.
  • From the order of the Zygentoma for example Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • From the order of the Blattaria for example Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasiusniger ⁇ Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • plants and plant parts can be treated.
  • Plants are understood here to mean 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 cultivars which can or cannot be protected by plant breeders' rights.
  • Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes be listed.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by coating in one or more layers.
  • all plants and their parts can be treated.
  • wild plant species or plant species and their parts obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • the treatment according to the invention can also cause superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and / or widening of the activity spectrum and / or one Enhance the effect the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products possible, which go beyond the effects that are actually to be expected.
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better Plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or Workability of the harvested products Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or Viruses and an increased tolerance of the plants to certain herbicidal agents.
  • transgenic plants are the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, tobacco, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton, tobacco and rapeseed are highlighted.
  • the traits are particularly emphasized as the increased defense of the plants against insects, arachnids, nematodes and snails by toxins which arise in the plants, in particular those which are caused by the genetic material from Baceurus Thuringiensis (e.g.
  • Bt plants The increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties (“traits”).
  • SAR systemic acquired resistance
  • systemin phytoalexins
  • elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties (“traits”).
  • traits are also particularly emphasized the increased tolerance of the plants to certain herbicidal active ingredients, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (for example "PAT” gene).
  • the genes conferring the desired properties (“traits”) can in each case also occur in combinations with one another in the transgenic plants.
  • “Bt plants” are corn varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YTELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g.
  • herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are marketed under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, e.g. rapeseed), IMI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas such as maize).
  • the herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (eg maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").
  • the plants listed can be treated particularly advantageously according to the invention with the active compound mixtures according to the invention.
  • the preferred ranges given for the mixtures above also apply to the treatment of these plants. Plant treatment with the mixtures specifically listed in this text should be particularly emphasized.
  • Insecticides and acaricides always have a synergistic effect if the effect of the active ingredient combinations is greater than the sum of the effects of the individually applied active ingredients.
  • X means the degree of destruction, expressed in% of the untreated control, when the active compound A is used in an application rate of m g / ha or in a concentration of m ppm,
  • Y means the degree of destruction, expressed in% of the untreated control, when the active compound B is used in an application rate of ng / ha or in a concentration of n ppm
  • E means the degree of destruction, expressed in% of the untreated control, when active ingredients A and B are used in application rates of m and ng / ha or in a concentration of m and n ppm
  • the combination is superadditive in its killing, ie there is a synergistic effect.
  • the degree of kill actually observed must be greater than the value for the expected degree of kill (E) derived from the above formula.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound one part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the preparation of active ingredient of the desired concentration and populated with caterpillars of the cabbage cockroach (Plutella xylostella, sensitive stem) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • the determined kill rates are calculated using the Colby formula (see sheet 1).

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne de nouvelles combinaisons de principes actifs à base de dérivés déterminés d'acide tétronique de formule (I), qui présentent de très bonnes propriétés insecticides et acaricides.
PCT/EP2004/014711 2004-01-07 2004-12-24 Combinaisons de principes actifs a proprietes insecticides et acaricides Ceased WO2005065453A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200410001112 DE102004001112A1 (de) 2004-01-07 2004-01-07 Wirkstoffkombinationen mit insektizide und akariziden Eigenschaften
DE102004001112.5 2004-01-07

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WO2005065453A1 true WO2005065453A1 (fr) 2005-07-21

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Cited By (4)

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WO2009118026A1 (fr) * 2008-03-27 2009-10-01 Bayer Cropscience Ag Utilisation de dérivés d'acide tétronique pour lutter contre les insectes et les tétranyques par arrosage, application au goutte-à-goutte ou immersion
WO2011089071A2 (fr) 2010-01-22 2011-07-28 Bayer Cropscience Ag Combinaisons de principes actifs acaricides et/ou insecticides
CN103651363A (zh) * 2012-09-06 2014-03-26 陕西美邦农药有限公司 一种含螺甲螨酯与沙蚕毒素类的杀虫组合物
CN104082300A (zh) * 2014-06-19 2014-10-08 广东中迅农科股份有限公司 一种含有吡丙醚和螺螨酯的杀虫杀螨组合物

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102013101573A1 (de) 2013-02-18 2014-08-21 Emitec France S.A.S Verfahren zum Beheizen einer Fördervorrichtung

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WO2001024634A1 (fr) * 1999-10-07 2001-04-12 Bayer Aktiengesellschaft Combinaisons d'agents actifs presentant des proprietes acaricides et insecticides
WO2001033966A2 (fr) * 1999-11-09 2001-05-17 Bayer Aktiengesellschaft Combinaison de substances actives a proprietes insecticides et acaricides
WO2001060158A1 (fr) * 2000-02-18 2001-08-23 Bayer Aktiengesellschaft Combinaisons de principes actifs aux proprietes insecticides et acaricides
WO2001070027A2 (fr) * 2000-03-21 2001-09-27 Bayer Aktiengesellschaft Combinaisons de substances actives a proprietes insecticides et acaricides
WO2001072125A2 (fr) * 2000-03-28 2001-10-04 Bayer Aktiengesellschaft Combinaisons de principes actifs ayant des proprietes insecticides et acaricides
WO2001076369A2 (fr) * 2000-04-11 2001-10-18 Bayer Cropscience Ag Combinaisons de substances actives a proprietes insecticides et acaricides

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WO2001024634A1 (fr) * 1999-10-07 2001-04-12 Bayer Aktiengesellschaft Combinaisons d'agents actifs presentant des proprietes acaricides et insecticides
WO2001033966A2 (fr) * 1999-11-09 2001-05-17 Bayer Aktiengesellschaft Combinaison de substances actives a proprietes insecticides et acaricides
WO2001060158A1 (fr) * 2000-02-18 2001-08-23 Bayer Aktiengesellschaft Combinaisons de principes actifs aux proprietes insecticides et acaricides
WO2001070027A2 (fr) * 2000-03-21 2001-09-27 Bayer Aktiengesellschaft Combinaisons de substances actives a proprietes insecticides et acaricides
WO2001072125A2 (fr) * 2000-03-28 2001-10-04 Bayer Aktiengesellschaft Combinaisons de principes actifs ayant des proprietes insecticides et acaricides
WO2001076369A2 (fr) * 2000-04-11 2001-10-18 Bayer Cropscience Ag Combinaisons de substances actives a proprietes insecticides et acaricides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009118026A1 (fr) * 2008-03-27 2009-10-01 Bayer Cropscience Ag Utilisation de dérivés d'acide tétronique pour lutter contre les insectes et les tétranyques par arrosage, application au goutte-à-goutte ou immersion
WO2011089071A2 (fr) 2010-01-22 2011-07-28 Bayer Cropscience Ag Combinaisons de principes actifs acaricides et/ou insecticides
US8722072B2 (en) 2010-01-22 2014-05-13 Bayer Intellectual Property Gmbh Acaricidal and/or insecticidal active ingredient combinations
CN103651363A (zh) * 2012-09-06 2014-03-26 陕西美邦农药有限公司 一种含螺甲螨酯与沙蚕毒素类的杀虫组合物
CN103651363B (zh) * 2012-09-06 2015-04-15 陕西美邦农药有限公司 一种含螺甲螨酯与沙蚕毒素类的杀虫组合物
CN104082300A (zh) * 2014-06-19 2014-10-08 广东中迅农科股份有限公司 一种含有吡丙醚和螺螨酯的杀虫杀螨组合物
CN104082300B (zh) * 2014-06-19 2017-02-15 广东中迅农科股份有限公司 一种含有吡丙醚和螺螨酯的杀虫杀螨组合物

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