WO1997006153A1 - Derives de 4-alkyl-1,3-oxa(thia)zoline, leur preparation et leur utilisation pour detruire des animaux parasites - Google Patents

Derives de 4-alkyl-1,3-oxa(thia)zoline, leur preparation et leur utilisation pour detruire des animaux parasites Download PDF

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Publication number
WO1997006153A1
WO1997006153A1 PCT/EP1996/003242 EP9603242W WO9706153A1 WO 1997006153 A1 WO1997006153 A1 WO 1997006153A1 EP 9603242 W EP9603242 W EP 9603242W WO 9706153 A1 WO9706153 A1 WO 9706153A1
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Prior art keywords
alkyl
formula
optionally
alkoxy
substituted
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PCT/EP1996/003242
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German (de)
English (en)
Inventor
Graham Holmwood
Johannes Kanellakopulos
Gerd Kleefeld
Christoph Erdelen
Ulrike Wachendorff-Neumann
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Bayer Aktiengesellschaft
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Priority to AU66589/96A priority Critical patent/AU6658996A/en
Publication of WO1997006153A1 publication Critical patent/WO1997006153A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3

Definitions

  • the invention relates to new 4-alkyl-1,3-oxa (thia) zoline derivatives, several processes 5 for their preparation and their use for controlling animal
  • Alk represents C 1 -C 2 alkyl
  • A represents in each case optionally substituted phenyl, pyridyl, thienyl or pyrazolyl,
  • B represents in each case optionally substituted phenyl, pyridyl or thienyl 0 and
  • Z represents oxygen or sulfur
  • the compounds of the formula (I) can be in the form of geometric and / or optical isomers or isomer mixtures of different compositions.
  • the invention relates both to the 5 pure isomers and to the isomer mixtures Furthermore, it was found that the new 4-alkyl-1,3-oxa (thia) zoline derivatives of the formula (I) are obtained if
  • Alk and B have the meaning given above,
  • Alk, A and B have the meaning given above, with a dehydrating agent, optionally in the presence of a diluent;
  • Alk, A and B have the meaning given above and
  • X represents halogen, alkylsulfonyloxy or optionally substituted
  • Alk, A and B have the meaning given above,
  • the compounds according to the invention are generally defined by the formula (I).
  • Alk is preferably methyl or ethyl.
  • A is preferably optionally up to five times, identical or different, by halogen, C ] -C 6 alkyl, C r C 6 alkoxy, C j -C 8 alkylthio, C r C 6 haloalkyl, C j -C 8 Haloalkoxy, C j -C 8 haloalkylthio, nitro or cyano substituted phenyl,
  • halogen optionally monosubstituted to trisubstituted by identical or different halogen, C r C 4 alkyl, C r C 4 alkoxy, C r C 4 haloalkyl, C, - ⁇ - halogenoalkyl alkoxy or cyano substituted pyridyl,
  • B is preferably optionally up to five times, identical or different, by halogen, C j -C ⁇ alkyl, C j -C ⁇ alkoxy, C j -C alkyl thio, C ] -C 4 haloalkyl, C j -C 8 haloalkoxy, C j -C 8 haloalkyl thio, - (OC 2 H 4 ) 1 .
  • Z preferably represents oxygen or sulfur.
  • Alk particularly preferably represents methyl.
  • B particularly preferably represents optionally one to three times, identical or different from F, Cl, Br, C j -C ⁇ alkyl, C j -C ] 2 alkoxy, C j -C, -, - alkylthio, simple to seven times , same or different by F and / or
  • Z particularly preferably represents oxygen or sulfur.
  • hydrocarbon radicals mentioned above in the definition of the compounds according to the invention are in each case straight-chain or branched as far as possible, even in conjunction with heteroatoms such as alkoxy.
  • Preferred compounds according to the invention are also substances of the formula (IA)
  • R 1 represents H, F, Cl or Br
  • R represents the general, preferred and particularly preferred phenyl substituents mentioned above under A,
  • n 0, 1 or 2
  • R represents the general, preferred and particularly preferred phenyl substituents mentioned above under B,
  • R 4 represents the general, preferred and particularly preferred phenyl substituents mentioned above under A,
  • n stands for the numbers 0, 1 or 2 and
  • Another preferred group of compounds of the formula (I) are those of the formula (LB)
  • R 5 represents halogen, C r C 4 alkyl, C r C 4 haloalkyl, C r C 4 alkoxy or C r C 4 haloalkoxy
  • alk and B preferably or particularly preferably have those meanings which have already been mentioned above in connection with the description of the Bonds of the formula (I) have been indicated as preferred or particularly preferred for these substituents
  • amino alcohols of the formula (II) are known and / or can be prepared by processes known per se, for example by using suitable amino acids with reducing agents, such as sodium borohydride in the presence of a diluent, such as tetrahydrofuran, at temperatures between -
  • amino acids required as precursors are known and / or can be prepared by processes known per se, for example by using corresponding hydantoins in the presence of bases, if appropriate with
  • hydantoins required as precursors are known and / or can be prepared from the corresponding ketones using processes known per se (cf. eg Chemical Abstract 86, 29495 and the preparation examples).
  • the carboxylic acids also required as starting materials for carrying out process (a) according to the invention are generally defined by the formula (III).
  • formula (III) A preferably or particularly preferably has those meanings which have already been mentioned above in connection with the description of the compounds of formula (I) have been indicated as preferred or particularly preferred for this substituent
  • the carboxylic acids of formula (III) are known organic synthetic chemicals
  • Formula (IV) provides a general definition of the amide alcohols required as starting materials for carrying out processes (b) and (d) according to the invention.
  • alk, A and B preferably or particularly preferably have those meanings which: already in connection with the description of the compounds of formula (I) have been given as preferred or particularly preferred for these substituents.
  • the amide alcohols of the formula (IV) are known and / or can be prepared by processes known per se.
  • the amide alcohols of the formula (IV) are obtained, for example, if one derives from the carboxylic acids of the formula (III)
  • an acid binder such as e.g. Triethylamine, pyridine, potassium carbonate, sodium hydroxide or potassium t-butoxide
  • a diluent such as e.g. Toluene, chlorobenzene, acetone or acetonitrile
  • Formula (V) provides a general definition of the amide derivatives required as starting materials for carrying out process (c) according to the invention.
  • alk, A and B preferably or particularly preferably have those meanings which are preferred or particularly preferred for these in connection with the description of the compounds of formula (I)
  • X preferably represents fluorine, chlorine, bromine, iodine, C 1 -C 4 -alkylsulfonyloxy, phenylsulfonyloxy or tolylsulfonyloxy, in particular chlorine, bromine, methylsulfonyloxy or tolylsulfonyloxy.
  • the amide derivatives of the formula (V) are known and / or can be prepared by processes known per se.
  • the amide derivatives of the formula (V) are obtained, for example, by reacting corresponding amide alcohols of the formula (IV) with halogenating agents, such as e.g. Thionyl chloride, phosphorus tribromide, phosphorus trichloride or phosphorus (V) chloride, optionally in the presence of a diluent or with sulfonylating agents, such as e.g. Methanesulfonic acid chloride or p-toluenesulfonic acid chloride, optionally in the presence of a diluent and a base.
  • halogenating agents such as e.g. Thionyl chloride, phosphorus tribromide, phosphorus trichloride or phosphorus (V) chloride
  • sulfonylating agents such as e.g. Methanesulfonic acid chloride or p-toluenesulfonic acid chloride, optionally in the presence of
  • Aromatic for example, come as a diluent in the halogenation
  • Hydrocarbons such as benzene, toluene, xylene, and halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and Dichloroethane in question
  • halogenating agent can be used in up to a five-fold excess
  • the reaction temperature in the halogenation can be varied within a substantial range.
  • the reaction is generally carried out between 0 ° C. and the boiling point of the diluent
  • Suitable diluents for sulfonation are, in addition to those described above as being suitable for the halogenation reaction, for example ethers such as diethyl ether or tetrahydrofuran
  • Organic bases such as triethylamine, N, N-dimethylamine, pyridine and 4-N, N-dimethylaminopyne are preferably used as the base in the sulfonation
  • the sulfonation agent is generally used in at least equimolar amounts
  • Processes (a) and (b) according to the invention are carried out using a dehydrating agent.
  • the dehydrating agents customary in organic chemistry can be used.
  • sulfuric acid polyphosphoric acid (PPS), phosphorus (V) oxide, di- Cyclohexylcarbodnmid (DCC), phosphorus (V) -sulf ⁇ d and the system T ⁇ phenylphosphin / T ⁇ ethylamin / Tetrachlormethan
  • Suitable diluents for carrying out processes (a) to (d) according to the invention are the customary organic solvents.
  • Aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, are preferably usable.
  • reaction temperatures can be varied within a substantial range when carrying out process (a) according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably at temperatures between 10 ° C and 100 ° C.
  • Process (a) according to the invention is generally carried out under normal pressure. However, it is also possible to work under elevated or reduced pressure - generally between 0.1 bar and 10 bar
  • the respectively required starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components used in each case in a larger excess.
  • the reactions are generally carried out in a suitable diluent is carried out in the presence of a dehydrating agent, and the reaction mixture is stirred for several hours at the required temperature.
  • Working up is carried out in the processes according to the invention in each case by customary methods
  • nitriles can also be used instead of the carboxylic acids of the formula (III), in which case a catalyst, such as zinc (II) chloride, is preferably used instead of a water-removing agent is used
  • reaction temperatures can be varied within a substantial range. In general, temperatures between -20 ° C. and + 150 ° C., preferably at temperatures between 0 ° C. and 100 ° C.
  • Process (b) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • 1 to 20 mol, preferably 1 to 5 mol, of dehydrating agent are generally employed per mole of amide alcohol of the formula (IV).
  • the amide alcohol of the formula (IV) is placed in a diluent and the dehydrating agent is then metered in.
  • the reaction mixture is stirred at the required temperature until the reaction has ended and then worked up in the customary manner
  • Process (c) according to the invention is carried out in the presence of a base.
  • All customary inorganic or organic bases come into consideration.
  • reaction temperatures can be varied within a substantial range. In general, temperatures between -20 ° C. and + 150 ° C., preferably at temperatures between 0 ° C. and 100 ° C.
  • Process (c) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar
  • process (c) 1 to 3 mol, preferably 1.0 to 1.5 mol, of a base are generally employed per mol of amide devat of the formula (V)
  • the amide derivative of the formula (V) and a base are mixed in a suitable diluent; the mixture is stirred at the required temperature until the reaction has ended and then worked up in the customary manner.
  • Process (d) according to the invention is carried out using a thienylating agent.
  • a thienylating agent suitable as such.
  • reaction temperatures can be varied within a substantial range when carrying out process (d) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably at temperatures between 0 ° C and 100 ° C.
  • Process (d) according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure - generally between 0.1 bar and 10 bar.
  • the amide alcohol of the formula (IV) is initially introduced into a diluent and the thienylating agent is then metered in.
  • the reaction mixture is then stirred at the appropriate reaction temperature until the end of the reaction and then worked up in the customary manner.
  • the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as crop protection agents. They are against normal sible and resistant species and effective against all or individual stages of development.
  • the pests mentioned above include:
  • Thysanura e.g. Lepisma saccharina.
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • 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, Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatataidella, piotifidella, aiotaparella, aiotaparella, pod , Psylla spp
  • Cheimatobia brumata Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp, Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp, Earioaulppa, Spariasodia spp, Heliodia spp.
  • Anthrenus spp Attagenus spp, Lyctus spp, Mehgethes aeneus, Ptinus spp, Niptus hololeucus, Gibbium psylloides, Tribolium spp, Tenebrio molitor, Agriotes spp, Conoderus spp, Melolontha melolontha, Amphimallon solstitica, Costelytra zealand
  • Hymenoptera From the order of the Hymenoptera, for example Diprion spp, Hoplocampa spp, Lasius spp, Monomorium pharaonis, Vespa spp
  • Acarina e.g. 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., Chorioptes spp. , Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus
  • Plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp.,
  • the compounds of the formula (I) according to the invention are notable in particular for outstanding insecticidal and acaricidal activity
  • insects and mites can be used with particularly good success for combating plant-damaging insects and mites, such as, for example, against larvae of the green rice leafhopper (Nephotettix cincticeps) or against the common spider mite (Tetranychus urticae)
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, loose powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulation in polymeric substances
  • 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
  • Agents ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents, for example, as liquid solvents essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, Alcohols, such as butanol or glycol, and their ethers and esters,
  • Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Solid carrier materials that come into question are, for example, 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 carrier materials for granules in question: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as 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 foam-generating agents are possible: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl
  • 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, and further additives can be mineral and vegetable oils his
  • Dyes such as inorganic pigments, for example 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 substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
  • Fungicides 2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ', 6'-dibromo-2-methyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxanilide; 2,6-dichloroN- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2-phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- ⁇ 2- [6- (2-cyano-phenoxy) pyrimidin-4-yloxy] phenyl ⁇ -3-methoxyacrylate; Methyl (E) methoximino [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ampropylfos,
  • Bacillus thuringiensis Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bifenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin,
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Fluufenprox
  • Fonophos Formothion, Fosthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron, Hexythiazox,
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Iver ⁇ mectin, Lambda-cyhalothrin, Lufenuron, Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos,
  • Methamidophos Methidathion, Methiocarb, Methomyl, Metolcarb, Milbemectin, Monocrotophos, Moxidectin, Naled, NC 184, NI 25, Nitenpyram, Omethoat, Oxamyl, Oxydemethon M, Oxydeprofos, Parathion A, Parathion M, Permethron, Phathoatophin, Phenthoat ,
  • Tebufenozid Tebufenpyrad
  • Tebupirimphos Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thio ⁇ methon, Thionazin, Thuringiensin, Tralomenhroniazonium, Tronomenophoniazonium Triaromoshroniazonium Triaromenhroniazonium Triaromenhroniazonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Triaromoshronizonium Tri
  • 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 through which the action of the active ingredients is increased 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 ingredient When used against hygiene pests and pests of stored products, the active ingredient is distinguished by an excellent residual action on wood and clay and by a good alkali stability on limed substrates.
  • 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) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, such as 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 By fighting these arthropods, deaths and reduced performance (in meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.
  • 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, such as 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 help of molded 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 such as Example by
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • insects may be mentioned by way of example and preferably, but without limitation:
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwinisis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • technical materials are to be understood as non-living materials, such as preferably plastics, adhesives, glues, papers and cartons, leather, wood and wood processing products and paints
  • the material to be protected against insect infestation is very particularly preferably wood and wood processing products
  • Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it, are to be understood as examples - timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors , Plywood, chipboard, carpentry or wood products that are used in general in house construction or in carpentry
  • the active compounds can be used as such, in the form of concentrates or generally customary formulations, such as powders, granules, solutions, suspensions, emulsions or pastes
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellants, optionally desiccants and UV stabilizers and if necessary dyes and pigments and other processing aids
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound 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 can be determined in each case by use of test series. In general, however, it is sufficient 0.0001 to 20% by weight. %, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected
  • An organic-chemical solvent or solvent mixture and / or an oily or oil-like heavy substance serves as the solvent and / or diluent volatile organic chemical solvent or solvent mixture and / or a polar organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent
  • oily or oily solvents preference is given to using oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • mineral oils or theirs are used as such volatile, water-insoluble, oily and oily solvents
  • Mineral oils with a boiling range of 170 to 220 ° C., test gasoline with a boiling range of 170 to 220 ° C., spindle oils with a boiling range of 250 to 350 ° C., petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and the like are used
  • the organic, slightly volatile 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 likewise has an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C., and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture
  • part of the organic-chemical solvent or solvent mixture is replaced by an aliphatic polar organic-chemical solvent or solvent mixture.
  • Aliphatic organic-chemical solvents containing hydroxyl and / or ester and / or ether groups are preferably used Glycol ether, ester or the like for use
  • the known organic-chemical binders are the water-dilutable synthetic resins and / or synthetic resins which are 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, for example 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.
  • 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 having 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, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycerol or glycerol ether - Kolether, glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as 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 industrial impregnation processes, e.g. Vacuum, double vacuum or pressure processes.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the ones mentioned in this document are preferably suitable as additional admixing partners.
  • Very particularly preferred admixing partners are insecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumurazole, as well as fungazazole, eponazole, epoxazolone, epoxazole, and epungazolone, as well as fungonazole, eponazole, eponazole, and epungazolone, as well as fungazazole, epazazole, as well as fungonazole, such as epazazole, as well as Fungazazole, like,
  • Tebuconazole Cyproconazole e, Metconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-Iodo-2-propynyl-butylcarbamate, N-Octyl-isothiazolin-3-one and 4,5-Dichlor-N-Octyl-isothiazolin-3-one.
  • the residue is taken up in 280 ml of 20% potassium hydroxide solution, stirred for 4 hours at room temperature and extracted three times with methylene chloride.
  • the combined organic phases are washed with water, dried over sodium sulfate and concentrated.
  • the residue is dissolved in toluene, acidified with concentrated hydrochloric acid and stirred vigorously.
  • the solid is filtered off with suction, suspended in water / methylene chloride and made basic with dilute sodium hydroxide solution.
  • the organic phase is separated off, dried over sodium sulfate and concentrated.
  • a mixture of 4-tert-butylacetophenone, 70 g (0.73 mol) ammonium carbonate and 20 g (0.31 mol) potassium cyanide in 200 ml n-propanol and 150 ml water is heated in an autoclave at 80 ° C. for 16 hours, then cooled and stirred with 1.5 l of water. The resulting solid is filtered off, washed with 1.5 l of warm water and dried.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 1 part by weight of alkylaryl polyglycol ether
  • 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.
  • Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with larvae of the green rice leafhopper Nephotettix cincticeps while the seedlings are still moist.
  • the kill is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
  • the compound according to Preparation Example 1 shows a kill of 100% after 6 days.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • 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 emulsifier-containing water.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.

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

Abstract

Ces dérivés nouveaux de 4-alkyl-1,3-oxa(thia)zoline répondent à la formule (I), dans laquelle alk désigne alkyle C1-C2; A désigne phényle, pyridyle, thiényle ou pyrazolyle le cas échéant substitués; B désigne phényle, pyridyle ou thiényle le cas échéant substitués; et Z désigne oxygène ou soufre. L'invention concerne également le procédé de préparation de ces dérivés et leur utilisation pour détruire des animaux parasites.
PCT/EP1996/003242 1995-08-04 1996-07-23 Derives de 4-alkyl-1,3-oxa(thia)zoline, leur preparation et leur utilisation pour detruire des animaux parasites WO1997006153A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU66589/96A AU6658996A (en) 1995-08-04 1996-07-23 4-alkyl-1,3-oxa(thia)zoline derivatives, their preparation and use for controlling animal pests

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19528778.9 1995-08-04
DE1995128778 DE19528778A1 (de) 1995-08-04 1995-08-04 4-Alkyl-1,3-oxa(thia)zolin-Derivate

Publications (1)

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WO1997006153A1 true WO1997006153A1 (fr) 1997-02-20

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DE (1) DE19528778A1 (fr)
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6265350B1 (en) 1998-06-16 2001-07-24 Hoechst Schering Agrevo Gmbh 1,3-oxazoline and 1,3-thiazoline derivatives, their preparation, and their use as pesticides

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0345775A1 (fr) * 1988-06-09 1989-12-13 Yashima Chemical Industrial Co., Ltd. Dérivé d'oxazoline ou de thiazoline
EP0432661A2 (fr) * 1989-12-09 1991-06-19 Yashima Chemical Industrial Co., Ltd. Dérivés de phenyl-2-oxazoline ou thiazoline substituée en 2 procédé, pour leur préparation et insecticides et acaricides les contenant
WO1995004726A1 (fr) * 1993-08-04 1995-02-16 E.I. Du Pont De Nemours And Company Oxazolines et thiazolines arthropodicides
EP0645085A1 (fr) * 1992-06-12 1995-03-29 Yashima Chemical Industrial Co., Ltd. Acaricide

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0345775A1 (fr) * 1988-06-09 1989-12-13 Yashima Chemical Industrial Co., Ltd. Dérivé d'oxazoline ou de thiazoline
EP0432661A2 (fr) * 1989-12-09 1991-06-19 Yashima Chemical Industrial Co., Ltd. Dérivés de phenyl-2-oxazoline ou thiazoline substituée en 2 procédé, pour leur préparation et insecticides et acaricides les contenant
EP0645085A1 (fr) * 1992-06-12 1995-03-29 Yashima Chemical Industrial Co., Ltd. Acaricide
WO1995004726A1 (fr) * 1993-08-04 1995-02-16 E.I. Du Pont De Nemours And Company Oxazolines et thiazolines arthropodicides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6265350B1 (en) 1998-06-16 2001-07-24 Hoechst Schering Agrevo Gmbh 1,3-oxazoline and 1,3-thiazoline derivatives, their preparation, and their use as pesticides
US6670307B2 (en) 1998-06-16 2003-12-30 Hoechst Schering Agrevo Gmbh 1,3-oxazoline and 1,3-thiazoline derivatives, their preparation, and their use as pesticides

Also Published As

Publication number Publication date
DE19528778A1 (de) 1997-02-06
AU6658996A (en) 1997-03-05

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