Classifications

• • 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
  • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
• • 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
  • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
• • 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
  • C07D263/14—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 with radicals substituted by oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
  • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
  • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

• the present invention relates to new 2- (2-methylphenyl) oxazolines, processes and intermediates for their preparation and their use for controlling animal pests.
• A stands for - (CH 2 ) p - (CR 1 R 2 ) q - (CH 2 ) r -R, where
• R 1 and R 2 independently of one another represent hydrogen or alkyl, p, q and r independently of one another represent 0, 1, 2 or 3, at least one index not equal to 0, and
• R for cyano represents an optionally substituted, saturated, partially saturated or unsaturated 5- or 6-membered heterocycle, or one of the following radicals:
• R 3 represents hydrogen, alkyl, haloalkyl, alkenyl, haloalkenyl, optionally substituted cycloalkyl or optionally substituted aryl,
• R 4 represents hydrogen, alkyl, alkenyl, haloalkyl, haloalkenyl, optionally substituted arylalkyl or in each case optionally substituted cycloalkyl or cycloalkylalkyl,
• R 5 and R 6 independently of one another are hydrogen, alkyl, alkoxy,
• R 3 and R 4 have the meaning given above, or
• R 5 and R 6 together represent a 5- or 6-membered alkylene chain which optionally contains an oxygen atom
• R 7 and R 8 are independently alkyl
• R 9 represents -OR 4 , -NR 3 R 4 or -N (R 3 ) -COOR 4 ,
• R 3 and R 4 have the meaning given above, and
• R 10 , R 11 and R 12 are independently alkyl or
• R 16 stands, wo ⁇ n
• R 16 represents alkyl, alkoxy, alkenyl, alkenyloxy, or in each case optionally substituted cycloalkyl, cycloalkyloxy or cycloalkylalkyloxy, for in each case optionally substituted phenyl or naphthyl or for NR 17 R 18 ,
• R 17 represents hydrogen or alkyl
• R 18 stands for alkyl, haloalkyl, for optionally substituted cycloalkyl or cycloalkylalkyl or for optionally substituted phenyl or phenylalkyl.
• the biphenyl ether oxazolines of the formula (I) can also be obtained as optical and / or geometric isomers, depending on the substituents.
• the present invention relates to both the isomer mixtures and the pure isomers.
• M represents a leaving group
• leaving group M are preferably halogen, such as chlorine or in particular
• Alkylsulfonyloxy such as especially methylsulfonyloxy
• optionally substituted arylsulfonyloxy such as, in particular, phenylsulfonyloxy, p-chlorophenylsulfonyloxy or tolylsulfonyloxy.
• All common inorganic and organic bases can be used as the base.
• bases include tertiary amines such as triethylamine, DBN, DBU, DABCO, alkali and alkaline earth metal hydroxides such as e.g. Sodium hydroxide, potassium hydroxide and calcium hydroxide as well as alkali and alkaline earth carbonates such as e.g. Sodium carbonate or potassium carbonate.
• Phase transfer catalysts can be used as catalysts.
• Examples include quaternary ammonium salts such as tetraoctylammonium bromide and benzyltriethylammonium chloride.
• Halogenated, aromatic or aliphatic hydrocarbons, ketones, nitriles and amides may preferably be used. Examples include toluene, acetone, acetonitrile, dimethylformamide and dimethylacetamide.
• the reaction temperature can be varied within a wide range. In general, temperatures between -20 ° C and 100 ° C, preferably between 0 ° C and 60 ° C.
• the reaction is generally carried out under normal pressure.
• the compounds of formula (II) and the compounds of formula (III) are generally used in approximately equimolar amounts. However, an excess of the compounds of the formula (III) can also be used.
• the processing is carried out according to generally accepted methods.
• Insects, arachnids and nematodes which are used in agriculture, in forests, in
• the compounds according to the invention are generally defined by the formula (I).
• A is preferably C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 3 -C 12 -alkenyl, C 3 -C 12 -alkynyl, optionally by halogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl ,
• A also preferably represents (CH 2 ) p - (CR 1 R 2 ) q - (CH 2 ) r -R,
• R 1 and R 2 are independently hydrogen or C 1-4 alkyl and
• p, q and r independently of one another represent 0, 1, 2 or 3, at least one index not equal to 0 and the sum of the indices not greater than 5.
• R preferably represents cyano; for one optionally by halogen, C1-C4-
• R 3 for hydrogen, -CC 6 - alkyl, -C 4 -haloalkyl, C -C 6 - alkenyl, C2-C6-haloalkenyl; optionally substituted one or more times, identically or differently by C1-C4-alkyl, halogen or C ⁇ -C4-halogenoalkyl-substituted C3-Cg-cycloalkyl, or for optionally single to five times, in particular single to triple, identical or different by halogen, C ⁇ -C4-alkyl, C1-C4- alkoxy, -C -C4-alkylthio, C ⁇ -C4-haloalkyl, C ⁇ -C4-haloalkoxy, Cj-C4-haloalkylthio, di (C] -C4) alkylamino, C ⁇ -C4- Alkyl carbonylamino, -C4-alkylcarbonyl -CC-C4-al
• R 4 for hydrogen, Ci-Cg-alkyl, C ⁇ -C 6 haloalkyl, C 2 -C 6 - alkenyl,
• C2-C6 haloalkenyl in each case optionally singly or multiply, identically or differently, C1-C4-alkyl, halogen or C1-C4-haloalkyl substituted C3-C6-cycloalkyl or C3-C5-cycloalkyl-C 1 -C 4 -alkyl, or for optionally single to five times, in particular single to triple, identical or different by halogen, C 4 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 4 -C 4 haloalkyl, C 4 -C 4 haloalkoxy, C 1 -C 4 haloalkylthio, Di (Ci-C4) alkylamino, cyano, nitro, -COOR 13 or -CONR 14 R 15 substituted C - or C ⁇ -aryl-Ci-Cö-alkyl,
• R 5 and R 6 independently of one another for hydrogen, C] -C4- alkyl, C1-C4-
• C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkyl-C 1 -C 4 -alkyl represents in each case optionally substituted once to five times, in particular mono- to trisubstituted by identical or different substituents from halogen, C1-C4 alkyl, C1-C4- alkoxy, -C-C4-alkylthio, C ⁇ -C 4 -haloalkyl, C1-C4-haloalkoxy, C ⁇ -C4-haloalkylthio, di (C ⁇ -C4) alky_amino, cyano, nitro, -COOR 13 or -CONR 14th R 15 is substituted phenyl or phenyl -CC-C4-alkyl, or is -OR 4 or -NR 3 R 4 ,
• R 5 and R 6 together represent - (CH 2 ) 5-, - (CH) 6- or - (CH 2 ) 2-O- (CH 2 ) 2-;
• R 7 and R 8 are independently C1-C4-alkyl
• R 9 represents -OR 4 , -NR 3 R 4 or -N (R 3 ) -COOR 4 ,
• R 10 , R 11 and R 12 independently of one another are C1-C4-alkyl.
• R 13 preferably represents hydrogen, C1-C4-alkyl, -C-C4-haloalkyl; C 3 -C 6 -
• R 14 and R 15 independently of one another preferably represent hydrogen, C
• R 14 and R 15 together represent - (CH 2 ) 5-, - (CH 2 ) 6- or - (CH 2 ) 2-O- (CH 2 ) 2-
• A also preferably represents COR 16 , wherein
• R 17 preferably represents hydrogen or C 1 -C 12 alkyl.
• R 18 is preferably C 1 -C 12 -alkyl, C ⁇ haloalkyl, or represents in each case optionally halogen, C ⁇ -C4-alkyl, O j ⁇ haloalkyl or C 2 -C 4 -halogenoalkenyl-substituted C 3 -C ⁇ o -Cycloalkyl or C 3 -C 10 -cycloalkyl-C Cg-alkyl or for each optionally optionally up to four times, identical or different by halogen, Ci-C ⁇ alkyl, C C ⁇ -haloalkyl, substituted phenyl or phenyl-C j -Cg alkyl.
• Halogen preferably represents F, Cl, Br, I in particular F, Cl and Br.
• C 3 -C 6 -cycloalkyl-C r C 4 -alkyl represents optionally halogen-substituted C 4 -C 6 cycloalkenylmethyl, represents optionally halogen-substituted C 4 -C 6 cycloalkenyl, for phenyl-C Cg- substituted, in each case, once or twice, identically or differently, by nitro, halogen, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -alkalkoxy alkyl (especially benzyl), naphthylmethyl, tetrahydronaphthylmethyl, pyridyl, furanyl, thiazolyl, oxazolyl or isoxazolyl-C 1 -C 3 -alkyl.
• A also particularly preferably represents (CH 2 ) p - (CR 1 R 2 ) q - (CH 2 ) r -R,
• R 1 and R 2 independently of one another represent hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl and
• p, q and r independently of one another represent 0, 1, 2 or 3, at least one index not equal to 0 and the sum of the indices not greater than 5, in particular not greater than 3.
• R particularly preferably represents cyano; for one of the following heterocycles
• R 3 is hydrogen; Methyl, ethyl, n- or i-propyl, the isomeric butyls, the isomeric pentyls, the isomeric hexyls; C ⁇ -C2 haloalkyl with 1 to 5 identical or different halogen atoms, such as F and Cl atoms, C3-C6-alkenyl, C3-Cg-haloalkenyl with 1 to 5 identical or different halogen atoms, such as F and Cl atoms; in each case optionally mono- to trisubstituted by identical or different fluorine, chlorine, methyl, ethyl, n- or i-propyl, or C j -C 2 haloalkyl having 1 to 5 identical or different halogen atoms, such as F and Cl atoms substituted cyclopropyl, Cyclopentyl or cyclohexyl, or for optionally single or double, identical or different by
• R 9 represents -OR 4 , -NR 3 R 4 or -N (R 3 ) -COOR 4 .
• R 4 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; C 1 -C 2 haloalkyl with
• halogen atoms such as F and Cl atoms; allyl optionally substituted one or more times by fluorine and / or chlorine; each optionally single to triple, identical or different, by fluorine, chlorine, methyl, ethyl, n- or i-propyl or C j -C ⁇ haloalkyl with 1 up to 5 identical or different halogen atoms, such as F and Cl atoms, substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyl-C 1 -C 2 alkyl, cyclopentyl-C 1 -C alkyl or cyclohexyl-C ⁇ -C 2 alkyl, or for each optionally single or double, identical or different by fluorine, chlorine, methyl, ethyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethyl
• R 13 particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl; Cj-C2-haloalkyl with 1 to 5 identical or different halogen atoms, such as F and Cl atoms; Allyl, butenyl, propargyl, butinyl, or for optionally single or double, the same or different
• R 14 and R 15 independently of one another particularly preferably represent hydrogen, C 1 -C alkyl, allyl, phenyl or benzyl.
• R 18 particularly preferably stands for or for phenyl or benzyl which is optionally monosubstituted or disubstituted, identically or differently, by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, Cj-04 -haloalkyl or C 1 -C -haloalkoxy.
• Halogen particularly preferably represents F, Cl, Br, in particular F and Cl.
• A also very particularly preferably represents (CH 2 ) p - (CR 1 R 2 ) q - (CH 2 ) r -R, where
• R 1 and R 2 independently of one another represent hydrogen, methyl or ethyl
• p, q and r independently of one another represent 0, 1, 2 or 3, where at least one index is not equal to 0 and the sum of the indices is not greater than 3.
• R very particularly preferably represents cyano; for one of the following heterocycles
• R 3 is hydrogen; Methyl, ethyl, n- or i-propyl, the isomeric butyls, the isomeric pentyls, the isomeric hexyls; C ⁇ -C2-haloalkyl with 1 to 5 identical or different halogen atoms, such as F and Cl atoms, C3-C6 alkenyl, C3-C5-haloalkenyl with 1 to 5 identical or different halogen atoms, such as F and Cl atoms; each optionally mono- to triple, identical or different by fluorine, chlorine, methyl, ethyl, n- or i-propyl or C ⁇ -C2-haloalkyl with 1 to 5 identical or different halogen atoms, such as F and Cl atoms, substituted cyclopropyl, cyclopentyl or cyclohexyl, or for optionally single or double, identical or different by fluorine, chlorine, methyl, e
• R 9 stands for -OR 4 .
• R 4 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; C 1 -C 2 haloalkyl having 1 to 5 identical or different halogen atoms, such as F and Cl atoms; allyl optionally substituted one or more times by fluorine and / or chlorine; in each case, if necessary, one to three times, the same or different by fluorine, chlorine, Methyl, ethyl, n- or i-propyl or C 1 -C 2 haloalkyl with 1 to 5 identical or different halogen atoms, such as F and Cl atoms, substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyl-C 1 -C 2 -alkyl, cyclopentyl-C ⁇ -C ⁇ alkyl or cyclohexyl
• R 13 very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl; C ⁇ -C2-haloalkyl with 1 to 5 identical or different halogen atoms, such as F and Cl atoms or for optionally single or double, identical or different by fluorine, chlorine, methyl, ethyl, methoxy, ethoxy substituted phenyl.
• R 14 and R 15 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, phenyl or benzyl.
• R 16 is methyl, ethyl, propyl; for methoxy, ethoxy, propoxy, butoxy; for cyclopropyl, cyclohexyl; for cyclohexyloxy; for phenyl, 2-chlorophenyl, 3-chlorophenyl, 2,6-difluorophenyl, 2-
• Trifluoromethoxyphenyl 4-trifluoromethoxyphenyl; 2,4-dichlorophenyl;
• R 18 very particularly preferably represents methyl, ethyl or phenyl which is optionally monosubstituted by chlorine.
• Halogen very particularly preferably represents F and Cl.
• a particularly preferred group of compounds are those of the formula (I) in which A stands for optionally substituted arylalkyl, in particular for optionally up to four times, identically or differently by nitro, halogen, C 1 -C 12 -
• Halogen represents F, Cl and Br.
• hydrocarbon radicals such as alkyl or alkenyl - also in compounds with heteroatoms such as alkoxy or alkylthio - are in each case straight-chain or branched as far as possible. If, for example, 2- (2-methylphenyl) -4- (4'-hydroxibiphenyl-4-yl) -1, 3-oxazoline and 4-trifluoromethylbenzylbromide are used as starting materials for carrying out the process according to the invention, the reaction can be carried out by the following Formula scheme are reproduced:
• Alk represents C r C 6 alkyl (especially methyl or ethyl),
• R 16 has the meaning given above
• an acidic catalyst such as sulfuric acid, acetic acid, aluminum chloride or hydrogen fluoride and optionally in the presence of a diluent such as methylene chloride or acetonitrile at temperatures between -10 ° C and 80 ° C
• R 16 has the meaning given above
• Cyclization and saponification can be carried out as a one-pot reaction or in separate steps.
• the compounds of formula (IV) are new. They can be prepared by known methods from 2-methylbenzamide and the corresponding haloacetaldehyde derivatives using the following formula (see, for example, EP-0 594 179).
• a base such as triethylamine or sodium hydroxide solution
• a diluent such as methylene chloride
• a base for example sodium hydroxide solution
• a phase transfer catalyst for example ammonium compounds
• a diluent for example dimethylformamide
• 2-Methylbenzoyl chloride of the formula (VII) has long been known and is easily accessible, for example from 2-methylbenzoic acid.
• the amino alcohol of the formula (VIII) is not yet known and can be obtained, for example, analogously to steps E) and F) of the process described below.
• acetyl chloride in the presence of a diluent such as e.g. Methylene chloride or dichloroethane and in the presence of one for the catalysis of
• A has the meanings given above, optionally chlorinated or brominated in the presence of a diluent such as methylene chloride or carbon tetrachloride at temperatures between -10 ° C and 25 ° C;
• a diluent such as methylene chloride or carbon tetrachloride at temperatures between -10 ° C and 25 ° C;
• a salt of formic acid e.g. Sodium formate
• a diluent optionally in a mixture with water, e.g. Ethanol / water and optionally in the presence of a phase transfer catalyst, e.g. reacting quaternary ammonium salts at temperatures between 50 ° C and 150 ° C;
• A has the meanings given above, with O-methylhydroxylamine, optionally in the form of a salt, for example the hydrochloride, in the presence of a diluent, for example alcohols or ethers, and if appropriate in the presence of a base, for example sodium acetate, at temperatures between 0 ° C and 60 ° C;
• a salt for example the hydrochloride
• a base for example sodium acetate
• a reducing agent e.g. Sodium boranate
• an acid e.g. Trifluoroacetic acid and optionally in the presence of a
• Diluents e.g. Converts tetrahydrofuran at temperatures between 0 ° C and 120 ° C;
• a base e.g. Triethylamine
• a diluent e.g. Tetrahydrofuran at temperatures between 0 ° C and 100 ° C;
• a chlorinating agent e.g. Thionyl chloride
• a diluent e.g. Toluene at temperatures between 20 ° C and 100 ° C and
• A has the meanings given above, in the presence of a base, such as sodium hydroxide solution; if appropriate in the presence of a phase transfer catalyst, such as, for example, ammonium compounds and, if appropriate, in the presence of a diluent, such as, for example, dimethylformamide, at temperatures between 0.degree. C. and 100.degree
• the starting material of the formula (XI) has long been known.
• Amide derivatives of formula (IV) with compounds of formula (XII) in the presence of an acid catalyst e.g. Hydrogen fluoride, boron trifluoride or aluminum chloride and in the presence of a diluent such as e.g. Reacts methylene chloride or acetonitrile at temperatures between 0 ° C and 80 ° C.
• an acid catalyst e.g. Hydrogen fluoride, boron trifluoride or aluminum chloride
• a diluent such as e.g. Reacts methylene chloride or acetonitrile at temperatures between 0 ° C and 80 ° C.
• the active ingredients are suitable for combating animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forests, in stock and
• Material protection and in the hygiene sector can preferably be used as pesticides. 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 for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
• Diplopoda for example, Blaniulus guttulatus.
• Thysanura e.g. Lepisma saccharina.
• Orthoptera e.g. 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.
• Phylloc spp. Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella,
• Tineola bisselliella Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura glamiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
• Anthrenus spp. Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, CosticaLontra- solstitialis .
• Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
• Chrysomyia spp. Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Os- cinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
• 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. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
• Plant-parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp ..
• the compounds of the formula (I) according to the invention are notable in particular for outstanding insecticidal and acaricidal activity.
• Plant-damaging insects such as, for example, against the horseradish leaf beetle larvae (Phaedon cochleariae), the green rice leafhopper (Nephotettix cincticeps), the caterpillars of the owl butterfly (Spodoptera frugiperda) and the peach aphids (Mycus persicae) Control of plant-damaging mites, such as against the common spider mite (Tetranychus urticae).
• plant-damaging insects such as, for example, against the horseradish leaf beetle larvae (Phaedon cochleariae), the green rice leafhopper (Nephotettix cincticeps), the caterpillars of the owl butterfly (Spodoptera frugiperda) and the peach aphids (Mycus persicae) Control of plant-damaging mites, such as 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, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers Fabrics.
• These 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, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can also be used as auxiliary solvents.
• auxiliary solvents e.g. organic solvents
• aromatics such as xylene, toluene, or alkylnaphthalenes
• chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
• aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
• Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• alcohols such as butanol or glycol and their ethers and esters
• ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
• strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• Possible solid carriers are: e.g. 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 silicic acid, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic 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 sulfite liquor and methyl cellulose.
• 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 phospho- lipids such as cephalins and lecithins and synthetic phospholipids.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90% and preferably in addition to extenders and / or surface-active agents.
• the active compound according to the invention can be mixed with other active compounds, such as insecticides, attractants, sterilants, bactericides,
• Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
• Amitraz Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringiensis, Bendiocarb, Ben portionsacarb, Bensultap, Betacyfluthrin, Bifenthrin,
• Cadusafos Carbaryl, Carbofran, Carbophenothion, Carbosulfan, Cartap, CGA 157
• Cyanophos cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, cypermethrin, cyromazine,
• Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb,
• Fenoxycarb Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb,
• Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
• Tebufenozid Tebufenpyrad
• Tebupirimphos Teflubenzuron
• Tefluthrin Temephos
• Terbam Terbufos
• Tetrachlorvinphos Thiafenox, Thiodicarb, Thiofanox, Thio-methon, Thionazine, Thuringiensin, Tralomenethriazonium, Triaromenhriazonium, Triaromenhriazonium, Triaromenhriazonium
• 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 connections through which the
• the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
• Application forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
• the application takes place in a customary manner adapted to the application forms.
• the active ingredient is distinguished by an excellent residual action on wood and clay as well as a good stability to alkali 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.
• Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp ..
• Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp.,
• Atylotus spp. Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp ., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp ..
• Siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp ..
• Panstrongylus spp .. From the order of the Blattarida, for example Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp ..
• Amblyomma spp. Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp ..
• Acarapis spp. Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodterol spp ., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp ..
• the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By fighting these arthropods, deaths and
• 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, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the 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 In
• Formula (I) as formulations for example powders, emulsions, flowable agents
• formulations for example powders, emulsions, flowable agents
• active compounds in an amount of 1 to 80% by weight, directly or after
• insects may be mentioned by way of example and preferably, but without limitation:
• Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucihegus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
• 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 joinery.
• the active substances 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 repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and other processing aids.
• the insecticidal compositions or concentrates used for protecting wood and timber products comprise the active ingredient "according to the invention in a concentration of 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.
• the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active compound, based on the material to be protected.
• organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility 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 agents.
• the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
• Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
• Mineral oils with a boiling range of 170 to 220 ° C, test gasoline with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C are advantageous.
• Turpentine oil and the like are advantageous.
• organic low-volatility oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 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, such as, for example, glycol ethers, esters or the like, are preferably used.
• the organic-chemical binders used are the water-thinnable 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 , e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as inden-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin used.
• binders consisting of or containing an acrylate resin, a vinyl resin , e.g. Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as inden
• 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, in itself Known dyes, pigments, water-repellent agents, odor correctors and inhibitors or anticorrosive agents and the like can be used.
• At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
• Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
• the binder mentioned can be wholly or partly by a fixing agent.
• mixture or a plasticizer (mixture) can be replaced.
• 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 originate 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 ether or higher molecular glycol glycerol ether , 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
• stearates such as butyl stearate or am
• Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, 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 process.
• the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
• the insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
• the compounds mentioned in this document are an integral part of the present application.
• Insecticides such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumazole, as well as fungonazole, as well as fungonazole, as well as fungonazole, as well as Fungazazole, as well as Fungazazole, like Fungazazole Tebuconazoles, cyproconazoles, metconazoles, imazalil, dichlorfluanide, tolylfluanid, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octylisothiazol-in-3-one .
• 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.
• Soybean shoots (Glycine max) are treated by dipping into the active ingredient preparation of the desired concentration and populated with caterpillars of the cotton capsule worm (Heliothis armigera) 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 compounds according to Examples 1-1, 1-2 and 1-6 at an exemplary active compound concentration of 0.1% caused 100% killing 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 with water to the desired concentration.
• Soybean shoots (Glycine max) are treated by immersing them in the active ingredient preparation of the desired concentration and populating them with Heliothis virescens caterpillars 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 compounds according to Examples 1-1, 1-2 and 1-6 at an exemplary active compound concentration of 0.1% caused 100% killing after 6 days.
• Solvent 3 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 concentrations.
• the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
• the compound according to Example 1-6 with an exemplary active compound concentration of 0.1%, caused 100% destruction after 7 days.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
• the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
• the compounds according to Examples 1-1, 1-2, 1-6, 1-7 and 1-9 at an exemplary active ingredient concentration of 0.1% caused 100% killing after 7 days.
• 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.
• Cabbage leaves (Brassica oleracea) are treated by dipping into the preparation of active compound of the desired concentration and populated with caterpillars of the cockroach (Plutella xylostella) 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 compounds according to Examples 1-1, 1-2 and 1-6 at an exemplary active ingredient concentration of 0.1% caused 100% killing after 7 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 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 owl butterfly (Spodoptera exigua) 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.
• 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.
• 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 owl butterfly (Spodoptera frugiperda) 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 compounds according to Examples II, 1-2, 1-3, 1-4, 1-5, 1-6, 1-8 and 1-9 caused a kill at an exemplary active compound concentration of 0.1% from 100% after 7 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 water containing emulsifier.
• the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
• 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 water containing emulsifier.
• the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
• the compounds according to Examples 1-2, 1-3, 1-4, 1-7, 1-8 and 1-9 at an exemplary active ingredient concentration of 0.1% caused 100% killing after 7 days .
• Test animals Lucilia cuprina larvae
• test tubes are removed for 2 days and the dolls are counted.
• the effect of the preparation of active substance is assessed according to the number of flies hatched after 1.5 times the development time of an untreated control. 100% means that no flies have hatched; 0% means that all flies hatched normally.

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

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• 1997
  • 1997-07-01 DE DE19727889A patent/DE19727889A1/de not_active Withdrawn
• 1998
  • 1998-06-18 JP JP50623599A patent/JP2002507217A/ja active Pending
  • 1998-06-18 KR KR1019997011965A patent/KR20010013942A/ko not_active Application Discontinuation
  • 1998-06-18 EP EP98939517A patent/EP0993451A1/de not_active Withdrawn
  • 1998-06-18 BR BR9810958-8A patent/BR9810958A/pt not_active Application Discontinuation
  • 1998-06-18 WO PCT/EP1998/003731 patent/WO1999001443A1/de not_active Application Discontinuation
  • 1998-06-18 AU AU88003/98A patent/AU8800398A/en not_active Abandoned
  • 1998-06-30 AR ARP980103179A patent/AR013156A1/es unknown

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