Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
  • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
  • C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms

Definitions

• the invention relates to new 1,2,4-oxadiazole derivatives, several processes for their preparation and their use for controlling animal pests.
• Various substituted 1,2,4-oxadiazole derivatives have already become known as compounds used to combat parasitic protozoa (cf. EP 7 529, EP 8 356), as analgesics (GB 1 198 726) or as herbicides (JP 57 175 177) (cf. also the previous, but not published patent application DE-P 42 32 418 by the applicant).
• substituted 1,2,4-oxadiazole derivatives such as 5- (4-chlorophenyl) -3- [2- (2,4-dichlorophenyl) ethyl] -1,2,4-oxadiazole and 5 - (2,4-dichlorophenyl) -3- [2- (2,4-dichlorophenyl) ethyl] -1,2,4-oxadiazole (J. Heterocycl. Chem., 15 (8), 1373-8, 1978 ).
• their use for controlling animal pests is not known.
• New 1,2,4-oxadiazole derivatives of the formula (I) have now been found
• R 1 represents halogen, alkyl or alkoxy
• R 2 represents hydrogen, halogen, haloalkyl or haloalkoxy
• R 3 represents hydrogen or alkyl
• R 4 represents hydrogen or alkyl
• R 5 represents halogen, trialkylsilylalkyl, trialkylsilylalkoxy
• A represents oxygen, sulfur, SO, SO 2 , alkylene, alkyleneoxy, alkylene thio, oxyalkylene, oxyalkyleneoxy, alkyleneoxyalkylene, alkenediyl or alkynediyl, k represents a number 0 or 1,
• R 7 represents alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, optionally substituted cycloalkyl, optionally substituted phenyl or optionally substituted pyridyl, or
• R 5 represents optionally substituted cycloalkyl, where one or two CH 2 groups which are not directly linked to one another are replaced by oxygen and / or sulfur,
• R 6 represents hydrogen, halogen, alkyl, haloalkyl, alkoxy or haloalkoxy, m stands for a number 1, 2 or 3, n stands for a number 1, 2 or 3,
• X stands for O, S, SO, SO 2 CH 2 or for a group NR 8 , in which R 8 stands for hydrogen or alkyl and
• Y represents a nitrogen atom or the group CR 9 , wherein
• R 9 represents hydrogen, halogen or alkyl, with the exception of the compounds: 5- (4-chlorophenyl) -3- [2- (2,4-dichlorophenyl) ethyl] -1,2,4-oxadiazole and 5- (2,4- Dichlorophenyl) -3- [2- (2,4-dichlorophenyl) ethyl] -1,2,4-oxadiazole (see J Heterocycl Chem 15 (8), 1373-8, 1978) and 3- (4-tert-butyl -phenoxymethyl) -5- (2,6-difluorophenyl) -1,2,4-oxadiazole (see DE-P 42 32 418)
• the compounds of the formula (I) can exist as geometric and / or optical isomers or isomer mixtures of different compositions.
• the invention relates to both the pure isomers and the isomer mixtures
• R 1 , R 2 , m and Y have the meaning given above,
• R represents alkyl, preferably methyl or ethyl
• Z represents a suitable leaving group such as halogen, or b) compounds of the formula (VI)
• R 1 , R 2 , R 3 , R 4 , Y and m have the meaning given above and represent a suitable leaving group, with compounds of the formula (VIII)
• X, R 5 , R 6 and n have the meaning given above, in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.
• the new 1,2,4-oxadiazole derivatives of the formula (I) are very suitable for controlling animal pests. They are particularly characterized by their high effectiveness against arthropods and nematodes. Surprisingly, the new 1,2,4-oxadiazole derivatives of the formula (I) according to the invention show a considerably better activity against animal pests than the constitutionally similar previously known compounds.
• R 1 preferably represents fluorine, chlorine, bromine, C 1 -C 6 alkyl or C 1 -C 6 alkoxy.
• R 2 preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 6 haloalkyl or C 1 -C 6 haloalkoxy.
• R 3 preferably represents hydrogen or C 1 -C 4 alkyl.
• R 4 preferably represents hydrogen or C 1 -C 4 alkyl.
• R 5 preferably represents fluorine, chlorine, bromine, tri- (C 1 -C 8 -) - alkyl-silyl- (C 1 -C 6 -) - alkyl or tri- (C 1 -C 8 -) - alkyl- silyl- (C 1 -C 6 -) alkoxy;
• Oxygen and / or sulfur are replaced, optionally phenyl which is monosubstituted to five times the same or different or optionally pyridyl which is monosubstituted or trisubstituted in the same way or differently, the following being mentioned as cycloalkyl, phenyl or pyridyl substituents:
• benzyliminooxymethyl optionally substituted by C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl and / or halogen,
• R 5 preferably represents optionally substituted C 3 -C 10 cycloalkyl, one or two CH 2 groups which are not directly linked to one another being replaced by oxygen and / or sulfur and the substituents mentioned for R for cycloalkyl are suitable.
• R 6 preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy or C 1 -C 8 haloalkoxy.
• m preferably represents a number 1, 2 or 3.
• n preferably represents a number 1, 2 or 3.
• X preferably represents O, S, SO, SO 2 , CH 2 or the group NH or N-CH 3 .
• Y preferably represents nitrogen or the group -CR 9 , in which
• R 9 represents hydrogen, fluorine, chlorine, bromine or C 1 -C 6 alkyl.
• R 1 particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 alkyl or C 1 -C 4 alkoxy.
• R 2 particularly preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -haloalkyl or C 1 -C 4 -haloalkoxy.
• R 3 particularly preferably represents hydrogen or methyl.
• R 4 particularly preferably represents hydrogen or methyl.
• R 5 particularly preferably represents fluorine, chlorine, bromine, trimethylsilylmethyl, trimethylsilylmethoxy, dimethylethylsilylmethyl, dimethylethylsilylmethoxy, butyl dimethylsilylmethyl, butyldimethylsilylmethoxy
• A represents oxygen, sulfur, SO, SO 2 or for C 1 -C 4 alkylene, C 1 -C 4 alkyleneoxy, C 1 -C 4 alkyl thio , C 1 -C 4 -oxyalkylene, C 1 -C 4 -oxyalkyleneoxy, C 1 -C 4 -alkyleneoxy-C 1 -C 4 -alkylene, especially for -CH 2 -, -CH 2 CH 2 -, -CH ( CH 3 ) -, -CH 2 CH 2 CH 2 -, -CH (CH 3 ) CH 2 -, -C (CH 3 ) 2 -, -CH 2 CH 2 CH 2 CH 2 -, -CH (CH 3 ) CH 2 CH 2 -, -CH (CH 3 ) CH 2 CH 2 -, -CH 2 CH (CH 3 ) CH 2 -, -CH 2 O-, -CH 2 CH 2 O-, -CH (CH 3 ) O-, -CH (CH
• k represents a number 0 or 1 and
• R 7 represents in each case optionally monosubstituted or polysubstituted by fluorine and / or chlorine C 1 -C 20 alkyl, C 2 -C 20 alkenyl or C 2 - C 20 alkynyl is, in particular in each case optionally monosubstituted or polysubstituted by fluorine and / or chlorine-substituted ethyl, n-propyl,
• R 5 particularly preferably represents optionally substituted C 3 -C 8 cycloalkyl, one or two CH 2 groups which are not linked to one another being replaced by oxygen and / or sulfur and the substituents mentioned for R 7 are suitable
• R 6 is particularly preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 6 - alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy or C 1 -C 6 haloalkoxy
• m particularly preferably represents a number 1, 2 or 3
• n particularly preferably represents a number 1 or 2
• X particularly preferably represents O, S, SO, SO 2 , CH 2 or the group NH or N-CH 3
• Y particularly preferably represents a nitrogen atom or the group -CR 9 .
• R 9 represents hydrogen, fluorine, chlorine, bromine or C 1 -C 6 alkyl
• R 3 represents hydrogen or methyl
• X represents CH 2 , O, S, SO or SO 2
• R 5 has the meaning given above.
• the compounds are in each case: 5- (4-chlorophenyl) -3- [2- (2,4-dichlorophenyl) ethyl] -1,2,4-oxadiazole, (2,4-dichlorophenyl) -3- [2 - (2,4-dichlorophenyl) ethyl] -1,2,4-oxadiazole and 3- (4-tert-butylphenoxymethyl) -5- (2,6-difluorophenyl) -1,2,4-oxadiazole excluded .
• alkyl radicals are also straight-chain or branched, if possible, in conjunction with heteroatoms, such as, for example, in alkoxy or alkylthio.
• n 2 the radicals R 6 can be the same or different.
• m> 1 the radicals R can be the same or different.
• the radical definitions can be combined as desired, that is, also between the preferred and particularly preferred ranges.
• Compounds are preferred of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , Y, m and n have the meanings mentioned as preferred.
• Formula (II) provides a general definition of the amidoximes required as starting materials for carrying out process a) according to the invention.
• X, R 3 , R 4 , R 5 , R 6 and n preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
• R 3 , R 4 , R 5 , R 6 and n have the meaning given above, with hydroxylamine or one of its salts, such as hydroxylamine hydrochloride, optionally in the presence of a base such as sodium carbonate and in the presence of a diluent.
• hydroxylamine or one of its salts such as hydroxylamine hydrochloride
• a base such as sodium carbonate
• a diluent by means of, for example, ethanol at temperatures between 0 ° C. and 150 ° C., preferably between 20 ° C. and 100 ° C.
• the compounds of the formula (IX) are known and / or can be prepared in a simple manner by known processes.
• the compounds of formula (IX) are obtained, for example, by e.g. corresponding phenols or anilines in
• a base such as sodium carbonate, hydride or hydroxide and in the presence of a diluent such as e.g. Acetone with a substituted acetonitrile such as e.g. Reacts chloroacetonitrile (cf. the preparation examples).
• a diluent such as e.g. Acetone with a substituted acetonitrile such as e.g. Reacts chloroacetonitrile
• the carboxylic acid orthoesters also to be used as starting materials for carrying out process a) according to the invention are generally of the formula
• the formulas (IV) and (V) generally define the carboxylic acid derivatives which are suitable for carrying out process a) according to the invention.
• R 1 , R 2 , Y and m have the meaning which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
• Z has the meaning of a suitable leaving group such as halogen or alkoxy.
• the carboxylic acid orthoesters of the formula (III) and the carboxylic acid derivatives of the formulas (IV) and (V) are generally known compounds of organic chemistry.
• the compounds of the formulas (II) and (III) are preferably reacted in the presence of an acid catalyst.
• the mineral acids preferably include hydrohalic acids such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid as well as sulfuric acid, phosphoric acid, phosphorous acid, nitric acid and the Lewis acids preferably include aluminum (III) chloride, boron trifluoride or its etherate, titanium (IV) chloride, Tin (IV) chloride.
• the following Lewis acids are particularly preferably used
• the process a) is generally carried out in such a way that compounds of the formula (II) are combined with an excess of compounds of the formula (III) and in the presence of an acidic one
• the catalyst is heated.
• Compound (III) is also a diluent.
• the reaction takes about 1 to 4 hours.
• the reaction is carried out at temperatures between + 20 ° C and + 200 ° C, preferably between + 100 ° C and + 155 ° C at the pressure which arises when heated to the required reaction temperature under the reaction conditions
• the compounds of the formulas (II) are reacted with the compounds of the formulas (IV) or (V), preferably in the presence of a base.
• Suitable bases are all customary acid acceptors.
• Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), are preferably used.
• Alkaline earth metal oxides such as magnesium and calcium oxide
• alkali and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate
• reaction of the compounds of formula (II) with the compounds of formulas (IV) or (V) are generally carried out in the presence of a diluent
• Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralm
• Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralm
• hydrocarbons can furthermore be used, furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, and also ketones, such as ketones, such as Acetone and methyl isopropyl ketone
• furthermore ethers such as diethyl ether, tetrahydrofuran and dioxane
• carboxylic acid esters such as ethyl acetate
• strongly polar solvents such as dimethyl sulfoxide and sulfolane. If the hydrolysis stability of the acid halide permits, the reaction can also be carried out in the presence of water.
• the process a) is generally carried out in such a way that compounds of the formula (II) with an equimolar amount or an excess of the compound of the formula (IV) or (V ) in the presence of a diluent and in the presence of an at least equimolar amount of base at temperatures between -20 ° C and 150 ° C, preferably between 0 ° C and 100 ° C until the reaction is complete.
• reaction mixture When the reaction is complete, the reaction mixture is cooled, concentrated in vacuo, the remaining residue is taken up in an organic solvent and worked up in a manner known per se.
• the products obtained can be purified in the usual way by recrystallization, vacuum distillation or column chromatography (cf. also the preparation examples).
• the cyclization of the compounds of formula (VI) is preferably carried out using diluents and, if appropriate, in the presence of a reaction auxiliary.
• Suitable diluents for carrying out process b) according to the invention are all inert organic solvents.
• halogenohydrocarbons in particular chlorohydrocarbons, such as tetrachlorethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene; Alcohols such as methanol, ethanol, isopropanol,
• Butanol Ethers such as ethyl propyl ether, methyl tert-butyl ether, n-butyl ether, di-n-butyl ether, di-isobutyl ether, di-iso-amyl ether, di-isopropyl ether, anisole, phenol, cyclohexyl methyl ether, diethyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, Dichlorodiethyl ether, nitrocarbon hydrogens such as nitromethane, nitroethane, nitrobenzene, chloronitrobenzene, o-nitrotoluene; Nitriles such as acetonitrile, butyronitrile, Isobutyronitrile, benzonitrile, m-chlorobenzonitrile; aliphatic, cycloaliphatic or aromatic hydrocarbons such as heptane, hex
• Carboxylic acids such as acetic acid, propionic acid, butyric acid. Mixtures of the solvents and diluents mentioned are also suitable.
• Carboxylic acids such as acetic acid or aromatic hydrocarbons such as toluene and xylene are preferred. All suitable dehydration reagents can be used as reaction aids, such as, for example, dicyclohexylcarbodiimide [DCC] (see, for example, F. Eloy Schwier. Chem. Forsch. 4 (1965) p. 807).
• DCC dicyclohexylcarbodiimide
• Process b) is generally carried out by heating compounds of the formula (VI) in a suitable diluent, if appropriate in the presence of a suitable reaction auxiliary.
• the reaction time is approx. 1 to 10
• the reaction is carried out at temperatures between + 20 ° C and + 200 ° C, preferably between + 70 ° C and + 170 ° C. It is preferable to work at the pressure which is established under the reaction conditions when heated to the required reaction temperature. When the reaction is complete, the reaction mixture is cooled, the whole
• reaction mixture was concentrated, taken up in an organic solvent and worked up in a manner known per se.
• the products obtained can be purified in the usual way by recrystallization, vacuum distillation or column chromatography (cf. also the preparation examples).
• process c) is used to prepare the new 1,2,4-oxadiazole derivatives of the formula (I) as the compound of the formula (VII), 3-chloromethyl-5- (2,6-difluorophenyl) -1,2,4 oxadiazole and as a compound of formula (VIII) 4- (4-trifluoromethylphenoxy) phenol, the process can be represented by the following reaction scheme:
• Formula (VII) provides a general definition of the 3,5-disubstituted 1,2,4-oxadiazoles required as starting materials for carrying out process c) according to the invention.
• Y, R 1 , R 2, R 3, R 4 and m preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
• Z stands for a suitable leaving group such as halogen, alkylsulfonyloxy or arylsulfonyloxy such as chlorine, bromine, methanesulfonyloxy or toluenesulfonyloxy.
• reaction of the compounds of formula (VII) with the compounds of formula (VIII) is preferably carried out in the presence of diluents and in the presence of a basic reaction auxiliary.
• Suitable diluents for carrying out process c) according to the invention are all inert organic solvents, as have already been mentioned in process b).
• acid binders such as amines, in particular tertiary amines, as well as alkali and alkaline earth compounds can be used as basic reaction auxiliaries.
• Examples include the hydrides, hydroxides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium, as well as further basic compounds such as trimethylamine, tribenzylamine, triisopropylamine, tri-butylamine, tribenzylamine, tricyclohexylamine, triamylamine, trihexylamine, N, N-dimethyl-aniline, N, N-dimethyl-toluidine, N, N-dimethyl-p-aminopyridine, N-methyl-pyrrolidine, N-methylpiperidine, N-methyl-imidazole, N-methyl-pyrrole, N-methyl morpholine, N-methyl-hexamethyleneimine, pyridine, quinoline, ⁇ -picoline, ß-picoline, isoquinoline, pyrimidine, acridine, N, N, N ', N'-tetra-methylenediamine, N, N, N'N'-tetra -
• Process c) is generally carried out by combining compounds of the formula (VII) with a slight excess of compounds of the formula (VIII), if appropriate in the presence of a diluent, and heating in the presence of a basic reaction auxiliary.
• the reaction time is about 5 to 30 hours.
• the reaction is carried out at temperatures between + 20 ° C and + 200 ° C, preferably between + 70 ° C and + 170 ° C. It is preferable to work at the pressure which is established under the reaction conditions when heated to the required reaction temperature.
• reaction mixture When the reaction is complete, the reaction mixture is cooled, the entire reaction mixture is filtered and concentrated in vacuo, the crude product which remains is worked up in a manner known per se.
• the products obtained can be purified in the customary manner by recrystallization, vacuum distillation or preferably by column chromatography (cf. also the preparation examples).
• the sulfur-bearing group can be oxidized.
• the oxidation can be carried out by customary methods using suitable oxidizing agents, such as peroxides (eg H 2 O 2 ), permanganate, perbenzoic acid, or using a mixture of potassium peroxomonosulphate, 2 KHSO 5 , KHSO 4 , and a solvent or solvent mixture (eg water, acetic acid, methanol ) are oxidized (see AR Katritzky, CW Rees in Comprehensive Heterocyclic Chemistry, Pergamon Press, Oxford, New York, 1984, Vol. 3, p. 96; DJ Brown et al. Chem. Soc. (C), 1971, p . 256)
• suitable oxidizing agents such as peroxides (eg H 2 O 2 ), permanganate, perbenzoic acid, or using a mixture of potassium peroxomonosulphate, 2 KHSO 5 , KHSO 4 , and a solvent or solvent mixture (e
• the oxidation can also be started or accelerated using catalysts.
• the active substances are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and 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, which occur in agriculture, in forests, in the protection of stored goods and materials and 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.
• Thysanura for example Lepisma saccharina.
• Collembola for example Onychiurus armatus.
• Orthoptera for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
• Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
• Heteroptera e.g. Eurygaster spp.
• Dysdercus intermedius Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
• Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphasis, spp.
• Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphasis,
• Nephotettix cincticeps Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp. Psylla spp.
• Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
• pellionella Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
• Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
• Plant parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp
• the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, natural and synthetic substances impregnated with active substances, and very fine encapsulations in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc., as well as ULV cold and warm mist forms
• formulations are prepared in a known manner, for example 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
• organic substances can also be used.
• Solvents are used as auxiliary solvents.
• Aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons such as are essentially suitable as liquid solvents Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
• Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers are possible:
• 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: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g.
• nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
• Possible dispersants are: e.g. Lignin liquor and methyl cellulose.
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and also 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, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes
• Substances and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
• the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from the formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
• Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
• Chlorfenvinphos Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cyanophos. Demeton
• Buprofezin chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexafiumuron, pyriproxifen, tebufenozide, teflubenzuron, triflumuron,
• the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
• Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.
• the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
• the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
• the application takes place in a customary manner adapted to the application forms.
• the active compounds according to the invention act not only against plant, hygiene and stored product pests, but also in the veterinary sector against animal parasites (ectoparasites and endoparasites) such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings, fleas and endoparasitic worms.
• animal parasites ectoparasites and endoparasites
• tick ticks such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings, fleas and endoparasitic worms.
• tick ticks such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings, fleas and endoparasitic worms
• the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are agricultural animals, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and Infest mice.
• arthropods are agricultural animals, such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and Infest mice.
• the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitonal, 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 aid of shaped articles containing active ingredients, such as necklaces, 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 by
• Emulsifier 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted to the desired concentrations with water containing emulsifier.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted to the desired concentrations with water containing emulsifier.
• Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and with horseradish leaf beetle larvae
• the kill is determined in%. 100% means that all beetle larvae have been killed, 0% means that no beetle larvae have been killed.
• the compound according to Preparation Example I-6 with an exemplary active ingredient concentration of 0.1%, shows a degree of killing of 100% after 7 days.
• Example C Panonychus test
• Emulsifier 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted to the desired concentrations with water containing emulsifier.
• the kill is determined in%. 100% means that all spider mites have been killed, 0% means that no spider mites have been killed.
• the compounds of preparation examples I-1, I-2, I-4 and I-5 show a degree of destruction of at least 95% after 7 days at an exemplary active ingredient concentration of 0.02%.
• Test animals adult Musca domestica, trunk Reichswald (OP, SP,
• the effectiveness of the active substance preparation is determined. 100% means that all flies have been killed, 0% means that no flies have been killed.
• the compound according to preparation example (VII-1) shows a degree of destruction of 100% at an exemplary active ingredient concentration of 1000 ppm.
• Example E
• Emulsifier 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
• Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cabbage cockroach (Plutella maculipennis) 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 compound according to preparation example I-3 with an exemplary active ingredient concentration of 0.1% after 7 days has a degree of destruction of 100%.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Agronomy & Crop Science (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
• Plural Heterocyclic Compounds (AREA)

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• 1994
  • 1994-01-17 DE DE4401108A patent/DE4401108A1/de not_active Withdrawn
• 1995
  • 1995-01-04 EP EP95906295A patent/EP0740663A1/de not_active Withdrawn
  • 1995-01-04 AU AU14550/95A patent/AU696288B2/en not_active Ceased
  • 1995-01-04 US US08/669,482 patent/US5985904A/en not_active Expired - Fee Related
  • 1995-01-04 MX MX9602806A patent/MX9602806A/es unknown
  • 1995-01-04 CN CN95191257A patent/CN1059672C/zh not_active Expired - Fee Related
  • 1995-01-04 CA CA002181184A patent/CA2181184A1/en not_active Abandoned
  • 1995-01-04 HU HU9601935A patent/HU220161B/hu not_active IP Right Cessation
  • 1995-01-04 BR BR9506515A patent/BR9506515A/pt not_active IP Right Cessation
  • 1995-01-04 WO PCT/EP1995/000024 patent/WO1995019353A1/de not_active Application Discontinuation
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  • 1995-01-10 TR TR00021/95A patent/TR28098A/xx unknown
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• 1996
  • 1996-07-12 NO NO962952A patent/NO307254B1/no not_active IP Right Cessation
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