Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
  • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
  • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
• • 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
  • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
  • C07C61/16—Unsaturated compounds
  • C07C61/40—Unsaturated compounds containing halogen
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
  • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D233/72—Two oxygen atoms, e.g. hydantoin
  • C07D233/74—Two oxygen atoms, e.g. hydantoin with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to other ring members
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D307/40—Radicals substituted by oxygen atoms
  • C07D307/42—Singly bound oxygen atoms

Definitions

• Pyrethroids are lipophilic synthethic compounds orginally derived from the active principle of pyrethrum. They show insecticidal properties, based on on a strong influence on the sodium channels in the nerve membranes of the insects.
• R 1 , R 2 can be halogen, CF 3 or CH 3 (see, e.g., EP-A 0638 543, EP-A 0 498 724, EP-A 0 779 269 or EP-A 0638 542).
• R represents: an alkyl radical containing 1 and 18 atoms of carbon; a benzyl radical optionally substituted by one or more radicals selected from the group consisting of alkyl radicals containing 1 to 4 carbon atoms, alkenyl radicals containing 2 to 6 carbon atoms, alkenyloxy radicals containing 2 to 6 carbon atoms, alkadienyl radicals containing 4 to 8 carbon atoms, the methylene dioxy radical and halogen atoms; either a group:
• substituent R. represents a hydrogen atom or a methyl radical and the substituent R 2 represents a monocyclic aryl or a -CH 2 -C ⁇ CH group; or a group:
• R 3 in which a represents a hydrogen atom or a methyl radical, R 3 retains the same meaning as previously, R'., and R' 2 identical or different, represent a hydrogen atom, a halogen atom, an alkyl radical containing 1 to 6 carbon atoms, an aryl radical containing 6 to 10 carbon atoms, an alkyloxycarbonyl group containing 2 to 5 carbon atoms, or a cyano group; or a group:
• B represents an oxygen or sulphur atom , -C(O)- or -CH 2 -,
• R 4 represents a hydrogen atom, a -C ⁇ N radical, a methyl radical, a CONH 2 radical, a
• R 5 represents a halogen atom or a methyl radical and n represents a number equal to 0,1 or 2; or a group:
• R 6 , R 7 , R 8 and R 9 represent a hydrogen atom, a chlorine atom, or a methyl radical and in which S/l symbolizes an aromatic cycle or an analogous dihydro or tetrahydro cycle; or a group:
• R 10 represents a hydrogen atom or a CH radical, preferably CH 3
• R 12 represents a -CH 2 - radical or an oxygen atom
• R u represents a thiazyl radical or a thiadiazyl whose bond with:
• R 12 can be located at any one of the available positions, R 12 being linked to Rlose by the carbon atom between the sulphur atom and a nitrogen atom; or a group:
• R 13 represents a hydrogen atom or a C ⁇ CH or CN radical
• a, b, c, d, e represent a hydrogen atom, a halogen atom, an alkyl, O-alkyl or S-alkyl radical containing up to 8 carbon atoms, saturated or insaturated, optionally substituted by one or more halogen atoms, a CN, NO 2 , NH 2 or OH radical, or R represents a radical:
• e and f represent a methyl, CH 2 F, CHF 2 or CF 3 radical; or R represents an aryl group containing 6 to 14 carbon atoms, optionally substituted by one or more OH, O-alkyl or alkyl groups containing 1 to 8 carbon atoms or by a CF 3 , OCF 3 or SCF 3 group; or R represents a pyridinyl, furanyl, thiophenyl oxazolyl or thiazolyl radical.
• R represents a radical:
• Y represents a hydrogen or halogen atom, a hydroxyl, NO 2 , CN or NH 2 , CH 2 OH or CH 2 OCH 3 radical, an alkyl, O-alkyl or S-alkyl radical containing up to 8 carbon atoms, optionally substituted by one or more halogen atoms, and/or optionally interrupted by one or more, preferably one or two, heteroatoms, preferably from the group consisting of O, S and N.
• a more particular subject of the invention is the compounds the preparation of which is given below in the experimental part and in particular the products of Examples 14, 27 and 43.
• the subject of the invention is also a preparation process characterized in that an acid of formula (II):
• R is preferably the remainder of an alcohol used in the pyrethroid series, or a functional derivative of this alcohol, and in this way, the sought compound of formula (I) is obtained.
• the functional derivative of the acid is preferably an acid chloride.
• an acid of formula (II) is reacted with the alcohol of formula (III)
• the operation is preferably carried out in the presence of diclohexylcarbodiimide.
• R and R 2 represent a hydrogen atom or an alkyl radical containing up to 8 carbon atoms.
• the products of formula (A) are known products described in EP-A 0 050 354.
• the compounds of formula (I) are suitable for controlling animal pests, especially insects, arachnids, helminths and molluscs, and very particularly preferably for controlling insects and arachnids, which are encountered in the hygiene sector, in animal breeding, in forestry, in the protection of stored products and materials, and in agriculture. They are active against normally sensitive and resistant species and against all or certain stages of development.
• the abovementioned pests include:
• Acarina for example, Acarus siro, Argas spp., Omithodoros spp.,
• Rhipicephalus spp. Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,
• Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Eotetranychus spp., Oligonychus spp. and Eutetranychus spp..
• Symphyla for example, Scutigerella immaculata.
• Thysanura for example, Lepisma saccharina.
• Orthoptera for example, Blatta orientalis, Periplaneta americana,
• From the order of the Heteroptera for example, Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus and Triatoma spp..
• From the order of the Homoptera for example, Aleurodes brassicae, Bemisia tabaci, T aleurodes vaporariorum, Aphis spp., Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelus bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax
• Psylloides chrysocephala Epilachna varivestis, Atomaria spp., Oryzaephilus sunnamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma,
• 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 and Lissorhoptus spp..
• Hymenoptera From the order of the Hymenoptera, for example, Diprion spp., Hoplocampa spp.,
• Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hypobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus,
• Oscinella frit Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae and
• helminths for example, Haemonchus, Trichostrongulus
• Gastropoda for example, Deroceras spp., Arion spp., Lymnaea spp., Galba spp., Succinea spp., Biomphalaria spp., Bulinus spp. and Oncomelania spp..
• the plant-parasitic nematodes which can be controlled in accordance with the invention include, for example, the root-parasitic soil nematodes such as those of the genera Meloidogyne (root knot eelworms, such as Meloidogyne incognita, Meloidogyne hapla and Meloidogyne javanica), Heterodera and Globodera (cyst-forming nematodes, such as Globodera rostochiensis, Globodera pallida, Heterodera trifolii) and of the genera Radopholus (such as Radopholus similis), Pratylenchus (such as Pratylenchus neglectus, Pratylenchus penetrans and Pratylenchus curvitatus), Tylenchulus (such as Tylenchulus semipenetrans), Tylenchorhynchus (such as Tylenchorhynchus dubius and Tylenchorhy
• the compounds according to the invention can also be used to control the nematode genera Ditylenchus (stem parasites, such as Ditylenchus dipsaci and Ditylenchus destructor), Aphelenchoides (leaf nematodes, such as Aphelenchoides ritzemabosi) and Anguina (leaf-gall nematodes, such as Anguina tritici).
• the invention also relates to compositions, especially insecticidal and acaricidal compositions, which comprise the compounds of the formula (I) in addition to suitable formulation auxiliaries.
• compositions according to the invention comprise the active compounds of the formula (I) in general in a proportion of from 0.001 % to 95% by weight.
• WP wettable powders
• EC emulsifiable concentrates
• SC oil- or water-based dispersions
• SE suspoemulsions
• DP dusting agents
• WP wettable powders
• EC emulsifiable concentrates
• SC oil- or water-based dispersions
• SE suspoemulsions
• DP dusting agents
• WG water- dispersible granules
• ULV ULV formulations, microcapsules, waxes or baits.
• Wettable powders are preparations, uniformly dispersible in water, which contain, beside the active compound and in addition to a diluent or inert material, wetting agents, for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, alkyl- or alkylphenolsulfonates, and dispersing agents, for example sodium ligninsulfonate or sodium 2,2'-dinaphthylmethane-6,6'-disulfonate.
• wetting agents for example polyethoxylated alkylphenols, polyethoxylated fatty alcohols, alkyl- or alkylphenolsulfonates
• dispersing agents for example sodium ligninsulfonate or sodium 2,2'-dinaphthylmethane-6,6'-disulfonate.
• Emulsifiable concentrates are prepared by dissolving the active compound in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons, with addition of one or more emulsifiers.
• organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons.
• emulsifiers the following can be used, for example: calcium salts of alkylarylsulfonates, such as Ca dodecylbenzenesulfonate, or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.
• alkylarylsulfonates such as Ca dodecylbenzenesulfonate
• nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide/ethylene oxide condensation products, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters
• Dusting agents are obtained by grinding the active compound with finely divided solid substances, for example talc, natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
• Granules can be prepared either by atomizing the active compound onto adsorptive, granulated inert material or by applying active compound concentrates onto the surface of carriers such as sand or kaolinites, or of granulated inert material, by means of adhesives, for example polyvinyl alcohol or sodium polyacrylate, or alternatively mineral oils.
• Suitable active compounds can also be granulated in the fashion conventional for the preparation of fertilizer granules, if desired as a mixture with fertilizers.
• the concentration of active compound is generally from approximately 10 to 90% by weight, the remainder to 100% by weight being composed of customary formulation components. In the case of emulsifiable concentrates, the concentration of active compound may generally be from approximately 5 to 80% by weight.
• Formulations in dust form generally comprise from 5 to 20% by weight of active compound, sprayable solutions from about 2 to 20% by weight. In the case of granules, the content of active compound depends partly on whether the active compound is in liquid or solid form and on which granulation auxiliaries, fillers, etc. are being used.
• the above mentioned formulations of active compound comprise, if appropriate, the adhesives, wetting agents, dispersants, emulsifiers, penetrants, solvents, fillers or carriers which are customary in each case.
• the concentrates which are in the commercially customary form, are if appropriate diluted in the customary manner for their use, for example using water in the case of wettable powders, emulsifiable concentrates, dispersions and some microgranules. Dust and granule preparations, and also sprayable solutions, are normally not diluted any further with other inert substances before being used.
• the application rate required varies with the external conditions, such as temperature and humidity among others. It can fluctuate within wide limits, for example between 0.0005 and 10.0 kg/ha or more of active compound, but is preferably between 0.001 and 5 kg/ha.
• the active compounds according to the invention may be present in their commercially customary formulations, and in the application forms prepared from these formulations, as mixtures with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth regulators or herbicides.
• the pesticides include, for example, phosphoric esters, carbamates, carboxylates, formamidines, tin compounds, compounds prepared by microorganisms, inter alia.
• Preferred co-components for mixtures are 1. from the group of the phosphorus compounds acephate, azamethiphos, azinphosethyl, azinphosmethyl, bromophos, bromophos- ethyl, cadusafos (F-67825), chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, demeton, demeton-S-methyl, demeton-S- methylsulphone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, EPN, ethion, ethoprophos, etrimfos, famphur, fenamiphos, fenit
• alanylcarb (OK-135), aldicarb, 2-sec-butylphenyl methylcarbamate (BPMC), carbaryl, carbofuran, carbosulfan, cloethocarb, benfuracarb, ethiofencarb, furathiocarb, HCN- 801 , isoprocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, l-methylthio(ethylideneamino) N-methyl-N- (morpholinothio)carbamate (UC 51717), triazamate; 3.
• BPMC 2-sec-butylphenyl methylcarbamate
• active compounds of which many are described in The Pesticide Manual (Editor: Clive Tomlin), 11th edition (1997), Crop Protection Publications/ISBN 1-90-901396-11-8 795.
• the content of active compound in the use forms prepared from the commercial formulations can vary within wide limits, and the concentration of active compound in the use forms can be from 0.0001 up to 95 % by weight of active compound, preferably between 1 and 50 % by weight.
• Application is effected in a conventional fashion, matched to the use forms.
• the content of the active compound in the use forms prepared from the commercial formulations may be from 0.00000001 to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
• the compounds of formula (I) have useful properties which allow their use preferred for combating parasites. It can, for example, be used for combating parasites of vegetation, parasites of premises and parasites in humans and animals.
• the products of the invention can be used to combat parasitic insects, nematodes and acarien parasites of vegetation and animals.
• a particular subject of the invention is the use of the compounds of formula (I) to combat parasites of vegetation, parasites of premises and parasites of warm-blooded animals.
• the active compounds according to the invention of the formula (I) are thus suitable for controlling endo- and ectoparasites in the veterinary sector or in the sector of animal husbandry.
• the active compounds according to the invention are in this case applied in a known fashion, such as by oral application in the form of, for example, tablets, capsules, potions or granules, by dermal application in the form of, for example, dipping, spraying, pouring-on and spotting-on and powdering, and also by parenteral application in the form of, for example, injection.
• novel compounds, according to the invention, of the formula (I) can accordingly also be employed particularly advantageously in livestock husbandry (for example cattle, sheep, pigs and poultry such as chickens, geese etc.).
• livestock husbandry for example cattle, sheep, pigs and poultry such as chickens, geese etc.
• the novel compounds if appropriate in suitable formulations (cf. above) and if appropriate with the drinking water or feed, are administered orally to the animals. Since excretion in the droppings occurs in an effective fashion, the development of insects in the animal droppings can be prevented very simply in this fashion.
• the dosages and formulations suitable in each case are particularly dependent on the type and stage of development of the productive animals and also on the degree of infestation, and can easily be determined and fixed by conventional methods.
• the novel compounds can be employed, for example, in dosages of 0.01 to 1 mg/kg of body weight.
• the compounds according to the invention are also suitable for use in technical fields, for example as wood preservatives, as preservatives in paints, in cooling lubricants for metalworking, or as preservatives in drilling and cutting oils.
• the products of formula (I) can also be used preferably to combat insects and other parasites of the soil, for example, coleoptera such as Diabrotica, click beetles, and cockchafer grubs, myriapoda such as 'greenhouse' centipedes and millipedes, and diptera such as gall midges and lepidoptera such as owlet moths.
• coleoptera such as Diabrotica
• click beetles click beetles
• cockchafer grubs myriapoda
• myriapoda such as 'greenhouse' centipedes and millipedes
• diptera such as gall midges and lepidoptera such as owlet moths.
• the products of the invention present an excellent shock effect.
• the products of formula (I) can also be preferably used to combat insects in premises, in particular to combat flies, mosquitoes and cockroaches, particularly Blatella germanica and Periplanta americana.
• the products of formula (I) are also photostable and are less toxic for mammals.
• the products of formula (I) can also be used to combat vegetable acarien and nematode parasites.
• the compounds of formula (I) can also be used to combat acarien parasites of animals, to combat, for example, ticks and notably ticks of the Boophilus species, those of the Hyalomnia species, those of the Amblyomnia species and those of the Rhipicephalus species or to combat all sorts of mange and notably sarcoptic mange, psoroptic mange and chorioptic mange.
• a subject of the invention is also a composition for combatting parasites of warm-blooded animals, parasites of premises and vegetation, comprising one or more, preferably 1 to 3, of the products of formula (I) defined below and in particular the products of formula (I) of Examples 14, 27 and 43.
• the subject of the invention is particularly an insecticide composition
• an insecticide composition comprising one or more of the products defined below as active ingredient.
• These compositions are prepared according to the usual processes of the agrochemical industry or the veterinary industry or the industry for products intended for animal fodder.
• compositions intended for agricultural use and for use in premises can optionally have added to them one or more other pesticide agents preferably from the group listed above.
• these compositions can be presented in the form of powders, granules, suspensions, emulsions, solutions, aerosol solutions, combustible strips, baits or other preparations usually employed for the use of this type of compound.
• these compositions comprise, in general, a vehicle and/or a non-ionic surfactant, ensuring, moreover, a uniform dispersion of the constitutive substances of the mixture.
• the vehicle used can be a liquid, such as water, alcohol, hydrocarbons or other organic solvents, a mineral, animal or vegetable oil, a powder such as talc, clays, silicates, kieselguhr or a combustible solid.
• the insecticide compositions according to invention comprise preferably 0.001 % to
• compositions according to the invention are used in the form of fumigant compositions and in the form of a solvent-based or water-based aerosol.
• compositions according to the invention can then advantageously comprise, for the non-active part, a combustible insecticide coil, or also an incombustible fibrous substrate.
• a heating apparatus such as an electric heater.
• the inert support can be, for example, composed of Pyrethrum marc, Tabu powder (or Machilus Thumbergii leaf powder),
• Pyrethrum stem powder cedar leaf powder, sawdust (such as pine sawdust), starch and coconut shell powder.
• the dose of active ingredient can then be, for example, 0.03 to 1% by weight.
• the dose of active ingredient can then be, for example, 0.03 to 95% by weight.
• compositions according to the invention for use in premises can also be obtained by preparing a sprayable oil based on the active ingredient, this oil soaking a lamp wick and then being set alight.
• concentration of active ingredient incorporated in the oil is, preferably, 0.03 to 95% by weight.
• Another subject of the invention coves acaricidal and nematicidal compositions comprising at least one of the products of formula (I) defined below as active ingredient.
• insecticide compositions according to the invention can optionally have one or more other pesticide agents added to them.
• the acaricide and nematicide compositions can be presented in particular in the form of powder, granules, suspensions, emulsions, solutions.
• wettable powders are preferably used, for foliar spraying, comprising
• liquids for foliar spraying comprising 1 to
• liquids for soil treatment comprising 300 to 500 g/l of active ingredient are preferably used.
• acaricide and nematicide compounds according to the invention are used, preferably, at doses comprised between 1 and 100 g of active ingredient per hectare.
• the products of the invention are in particular used to combat lice as a preventative or curative and to combat mange.
• the products of the invention can be administered by external route, by spraying, by shampooing, by bathing or painting on.
• the product of the invention for veterinary use can also be administered by painting the spine according to the "pour-on" method.
• products of the invention can also be used as biocides or as growth regulators.
• a subject of the invention is the combinations endowed with insecticide, acaricide or nematicide activity, characterized in that they comprise as active ingredient, on the one hand at least one of the compounds of the general formula (I) and on the other hand, at least one of the pyrethrinoid esters chosen from the group constituted by the esters of allethrone, of 3,4,5,6-tetrahydrophthal-imidomethyl alcohol, of 5-benzyl-3-furyl methyl alcohol, of 3-phenoxybenzyl alcohols and of alpha-cyano-3-phenoxybenzyl alcohol with chrysanthemic acids, by the esters of 5-benzyl-3-furyl methyl alcohol with
• the compounds of the formula (I) can also be employed for controlling pests in crops of known or still to be developed plants which are modified by genetic engineering.
• the transgenic plants generally have particularly advantageous properties, for example by resistance toward certain crop protection agents, resistance toward plant diseases or causative organisms of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses.
• Other particular properties concern, for example, the harvest with respect to amount, quality, storage stability, composition and specific ingredients.
• transgenic plants having increased starch content or a modified quality of the starch, or those having a different fatty acid composition of the harvested goods are known.
• cereals such as wheat, barley, rye, oats, millet, rice, maniok and maize or else in crops of sugar beet, cotton, soya, rapeseed, potato, tomato, pea and other vegetable species.
• the invention therefore also provides the use of compounds of the formula (I) for controlling harmful organisms in transgenic crop plants.
• Stage B [IR-cis(Z)] 2,2-dimethyl-3-(2-fluoro-3-methoxy-3-oxo-1 -propenyl) cyclopropane carboxylate of (1 ,1 -dimethyl) ethyl
• the reaction medium was diluted with ethyl acetate and washed with water, with an aqueous solution of sodium acid carbonate, with a 0.5 N solution of hydrochloric acid and with water. After drying, filtering and concentrating 21.61 g of sought product was obtained.
• the temperature was returned to -60°C followed by pouring into a 2N solution of hydrochloric acid. 600 cm 3 of ethyl acetate was added followed by saturation with sodium chloride.
• the reaction medium was decanted and extracted with ethyl acetate, followed by washing, drying, filtering and concentrating at 40°C under reduced pressure.
• the residue was chromatographied on silica eluting with a heptane - ethyl acetate mixture, followed by washing with water, with a saturated solution of sodium acid carbonate and with salt water.
• the product obtained was dried, filtered, concentrated, chromatographied on silica eluting with a heptane - ethyl acetate mixture (7-3). In this way 12.38 g of sought product was obtained.
• reaction medium was taken to I20°C, maintained under agitation for 30 minutes and the temperature returned to 20°C. Dilution was carried out with 250 cm 3 of isopropyl ether followed by washing with water, drying, filtering and concentrating. 11 g of sought product was obtained.
• DMAP and 454 mg of DCC are added at 0°C to a solution containing 379 mg of acid and 588 mg of the alcohol to be esterified and 20 cm 3 of methylene chloride.
• the temperature is allowed to rise to 20°C and agitation is carried out for 1 hour 30 minutes followed by filtering, diluting and washing with a 0.5N solution of hydrochloric acid. Decanting is carried out followed by drying, filtering, concentrating and taking up in toluene at 20°C.
• 0.5 g of tosyl alcohol is added followed by taking the reaction medium to 120°C and returning it to 20°C when the gas evolution is finished.
• Dilution is carried out with ethyl acetate followed by washing with sodium acid carbonate, drying, filtering and concencentrating.
• a product is obtained which is chromatographed on silica, eluting with a heptane-ethyl acetate mixture (80-20).
• the impure product resulting from the first chromatography was chromatographed again eluting with a heptane-isopropyl mixture (95-5) and in this way 2.09 g of sought product was obtained. Thus a total of 12 g of sought product was obtained.
• reaction medium was agitated for 30 minutes at 0°C, the temperature was allowed to rise to 20°C and agitation was carried out overnight. Concentration was carried out followed by taking up in toluene and returning the temperature to 40°C.
• the solution obtained was added to a solution which was prepared as follows: a mixture of 250 cm 3 of THF and 70 cm 3 of methanol was cooled down to -70°C and 12 g of sodium borohydride was added. Agitation was carried out for 1 hour at -70°C. The temperature was allowed to rise to -35°C, then returned to -50°C and the reaction medium was poured into a 2N solution of HCI. Agitation was carried out for 10 minutes followed by saturation with sodium chloride, extraction with ethyl acetate, washing with sodium acid carbonate, drying, filtering and concentrating. The product obtained was chromatographed eluting with a heptane-ethyl acetate mixture (7-3). In this way 26.37 g of sought product was obtained.
• the protocol used was the same as the protocol of the activity test for Musca domestica.
• Aerosols were prepared which had the following formulations. The quantities indicated were quantities by weight.
• the tests were carried out in a windtunnel.
• the active ingredient was diluted to 0.003 % w/v in an 80 % OPD / 20 acetone mixture.
• Controls i.e., sprayed with the carrier liquid alone) were inserted at the beginning of the test, and twice at the end.
• the compounds according to the invention are significantly more effective against Blattela than Imiprothrin.

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Citations (4)

• 1997
  • 1997-12-22 FR FR9716243A patent/FR2772759B1/fr not_active Expired - Fee Related
• 1998
  • 1998-12-10 BR BR9814368-9A patent/BR9814368A/pt not_active IP Right Cessation
  • 1998-12-10 JP JP2000525364A patent/JP2001526251A/ja active Pending
  • 1998-12-10 WO PCT/EP1998/008053 patent/WO1999032426A1/en not_active Application Discontinuation
  • 1998-12-10 CN CN98813234A patent/CN1284055A/zh active Pending
  • 1998-12-10 AU AU21602/99A patent/AU2160299A/en not_active Abandoned
  • 1998-12-10 AP APAP/P/2000/001870A patent/AP2000001870A0/en unknown
  • 1998-12-10 NZ NZ505270A patent/NZ505270A/xx unknown
  • 1998-12-10 EP EP98965806A patent/EP1042272A1/en not_active Withdrawn
  • 1998-12-10 ID IDW20001185A patent/ID26251A/id unknown
  • 1998-12-10 KR KR1020007006941A patent/KR20010033455A/ko not_active Application Discontinuation
  • 1998-12-10 TR TR2000/01974T patent/TR200001974T2/xx unknown
  • 1998-12-18 AR ARP980106518A patent/AR016438A1/es not_active Application Discontinuation
  • 1998-12-21 ZA ZA9811707A patent/ZA9811707B/xx unknown
• 2000
  • 2000-06-22 OA OA1200000186A patent/OA11434A/en unknown

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