Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D213/72—Nitrogen atoms
  • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
  • C07D215/38—Nitrogen atoms
  • C07D215/42—Nitrogen atoms attached in position 4
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
  • C07D239/32—One oxygen, sulfur or nitrogen atom
  • C07D239/42—One nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
  • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
  • C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
  • C07D285/01—Five-membered rings
  • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
  • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
  • C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles

Definitions

• the invention relates to new substituted aminoheterocyclylamides, processes and intermediates for their preparation and their use for controlling animal pests and as fungicides.
• N-heterocyclylamides such as, for example, isothiazolyl, pyridyl, thiadiazolyl or pyrimidinyl amides
• insecticidal properties cf., for example, WO 95/31 448, DE-A-9 542 372; WO 93/04 580, WHERE
• R. or R 'N -v Q is where
• R 1 represents alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkoxy, alkylthio or optionally substituted cycloalkyl
• R 2 represents hydrogen, halogen, cyano, nitro, thiocyanato, alkoxycarbonyl, alkenyloxycarbonyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl or thiocarbamoyl or
• R 1 and R 2 together with the carbon atoms to which they are attached represent an optionally substituted 5- or 6-membered carbocyclic ring
• R 3 represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkenyloxycarbonyl, alkylsulfonyl, in each case optionally substituted arylcarbonyl, aryloxycarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,
• R 4 and R 5 independently of one another for hydrogen or for the radicals -COR 6 ,
• R 6 , R 7 and R 8 independently of one another are alkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl, alkylcarbonyloxyalkyl, alkoxycarbonylalkyl; Alkenyl, haloalkenyl; Alkynyl, haloalkynyl; each optionally substituted cycloalkyl, cycloalkylalkyl, cycloalkoxyalkyl or cycloalkylthioalkyl; each optionally substituted aryl, arylalkyl, aryloxyalkyl or arylthioalkyl or represent an optionally substituted heterocycle,
• X 1 and X 2 independently of one another represent halogen, nitro, cyano, alkyl, alkoxy or haloalkyl,
• n and n independently of one another represent 0, 1, 2 or 3,
• Y stands for optionally substituted alkylene, alkenylene or alkyleneoxy
• Halogen for F, Cl, Br, I in particular for F, Cl, Br and highlighted for F or Cl.
• R 4 " 1 stands for the meanings of R 4 , except hydrogen
• G represents a leaving group, e.g. for halogen (especially chlorine), imidazolyl, benzimidazolyl, 1,2,4-triazolyl, pyrazolyl or benzotriazolyl,
• Formula (I) provides a general definition of the substituted aminoheterocyclylamides according to the invention
• Het preferably represents the heterocycles
• R 1 preferably represents -C-alkyl, C -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine and bromine atoms, C 1 -C 4 -alkoxy-C 1 -C -alkyl, C ⁇ -C 4 -Alkylthio-C 1 -C4-alkyl, -C-C 4 -alkoxy, C 1 -C 4 -alkylthio or for optionally single to triple, identically or differently substituted by -CC alkyl or halogen substituted C ß -Cg
• Cycloalkyl R 2 preferably represents hydrogen, halogen, cyano, nitro, thiocyanato, C j -C 4 alkoxy carbonyl, C 2 -C alkenyloxy carbonyl, C 1 -C 4 alkyl thio, C 1 -C haloalkylthio with 1 to 5 identical or different halogen atom
• R 1 and R 2 together with the carbon atoms to which they are attached, preferably represent a carbocyclic 5- or 6-membered which is optionally monosubstituted to trisubstituted, identically or differently
• Halogen substituted C 3 -C 6 cycloalkyl R 5 independently of one another preferably represent hydrogen or the radicals -COR 6 , -COOR 7 or -SO 2 R 8 , where
• R 6 , R 7 and R 8 independently of one another, preferably represent C j -Cg-alkyl, C j - Cg-haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine, chlorine or bromine atoms, -C-C -alkoxy- C ⁇ -C 8 - alkyl, C 1 -C 4 -alkylthio-C 1 -C 8 alkyl, C 1 -C 4 alkylcarbonyloxy-C 1 -C 8 - alkyl, C ⁇ -C alkoxycarbonyl-C ⁇ -C 4 8 -alkyl; C 2 -C 8 alkenyl, C 2 -C 8 - haloalkenyl same to 5 with 1 or atoms different halogen such as fluorine or chlorine atoms; C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl having 1 to 5 identical or different halogen atoms
• Alkenyl, C 2 -C 4 haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, nitro or cyano, are suitable for each optionally substituted up to five times (preferably once to three times), substituted identically or differently in the ring Phenyl,
• Halogen, nitro, cyano, C -C - alkyl, C ⁇ -C - alkoxy, C 1 -C 4 alkylthio, C ⁇ -C 4 -Halogena_kyl, C j-C4-haloalkoxy and C ⁇ -C haloalkyl thio in question come.
• suitable heterocycles on the ring nitrogen atom can optionally be substituted by a radical Z, where
• Alkylcarbonyl such as especially methylcarbonyl or ethylcarbonyl
• C 1 -C 4 alkyl such as especially methyl or ethyl
• halogen such as especially fluorine or chlorine
• C j - C 4 Haloalkyl such as in particular trifluoromethyl
• C 1 -C 4 - Alkoxy such as especially methoxy
• C 1 -C 4 -haloalkoxy such as in particular trifluoromethoxy
• Suitable heterocycles are to be understood as meaning nitrogen-containing heterocycles in which at least one ring nitrogen has no double bond and is therefore available for substitution.
• X 1 and X 2 independently of one another preferably represent fluorine, chlorine, bromine, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C -alkoxy or C r C 4 -haloalkyl having 1 to 5 identical or different halogen atoms, such as Fluorine or chlorine atoms.
• n and n independently of one another are preferably 0, 1 or 2.
• Y preferably represents C r C 6 -alkylene, C j -C 6 -hydroxyalkylene, -C-C 4 -alkoxy-
• halogen atoms such as fluorine or chlorine atoms
• Halogen preferably represents F, Cl, Br, I, in particular F, Cl, Br and particularly emphasized F and Cl.
• Het is particularly preferably one of the heterocycles
• R 1 particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH 2 C1, CH 2 Br, CHC1CH 3 ; Methoxy, ethoxy, methoxy methyl, ethoxymethyl, methylthiomethyl, methylthio or cyclopropyl
• R 2 particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, thiocyanato, methoxycarbonyl, ethoxycarbonyl, l-propoxycarbonyl, n-propoxycarbonyl, allyloxycarbonyl, methylthio, methylsulfinyl, methylsulfonyl or CSNH 2 , or
• R 1 and R 2 particularly preferably together with the carbon atoms to which they are attached, represent an optionally mono- or disubstituted, identically or differently substituted carbocyclic 5- or 6-ghed ⁇ gen ring, the substituents being fluorine, chlorine, Methyl, ethyl, methoxy, T ⁇ fluormethoxy, nitro and cyano come into question
• R 3 particularly preferably represents hydrogen, methyl, ethyl, n- or l-propyl, methoxymethyl, ethoxymethyl, n-propoxymethyl, n-butoxymethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, l-propoxycarbonyl, allyloxycarbonyl, methylsulfonyl, in each case optionally simply or phenylcarbonyl, phenoxycarbonyl or benzyl substituted twice, identically or differently in phenyl by fluorine, chlorine, methyl or trifluoromethyl, or for cyclopropyl
• R 4 and R 5 independently of one another particularly preferably represent hydrogen or the radicals -COR 6 , -COOR 7 or -SO 2 R 8 , where
• R 6 , R 7 and R 8 independently of one another particularly preferably represent Cj-
• Halogen atoms such as fluorine, chlorine or bromine atoms, C 1 -C 2 -alkoxy- C r C 4 -alkyl, C r C 2 -alkylth ⁇ o-C r C 4 -alkyl, C r C 4 -alkylcarbonyloxy-
• C alkyl suitable substituents being in each case halogen, C ⁇ -C4-alkyl, C j - C same -halogenoalkyl having 1 to 5 or different halogen atoms, such as fluorine or chlorine atoms, C ⁇ -C - alkoxy, C 2 -C j -Halogenalk - Oxy with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C -C4 alkenyl, C 2 -C 4 haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, nitro or cyano in question come, alkyl in each case optionally mono- to trisubstituted by identical or different in the ring substituted phenyl, phenyl-C 1 -C 2, phenoxy-C -C 2 - alkyl or phenylthio-C 1 -C 2 alkyl, substituents
• Alkylcarbonyl such as in particular methylcarbonyl or ethylcarbonyl, or for optionally single or double, identical or different by C ! -C 4 - alkyl, such as in particular methyl or ethyl, halogen, such as in particular fluorine or chlorine, C j - C 4 haloalkyl, such as in particular tnfluoromethyl, CC 4 -alkoxy, such as in particular methoxy, and C j -C 4 - Halogenalkoxy, such as, in particular, T ⁇ fluormethoxy substituted phenylsulfonyl
• X 1 and X 2 independently of one another particularly preferably represent fluorine, chlorine,
• n and n independently of one another are particularly preferably 0, 1 or 2, in particular 0 or 1
• Y particularly preferably represents one of the radicals -CH 2 -, -CH (CH 3 ) -,
• Het very particularly preferably represents one of the heterocycles
• R 1 very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl; CH 2 C1, CH 2 Br, methoxy, ethoxy, methylthio or cyclopropyl.
• R 2 very particularly preferably represents hydrogen, chlorine, bromine, cyano, nitro, methoxycarbonyl, ethoxycarbonyl, methylthio, methylsulfinyl or methylsulfonyl; or
• R 1 and R 2 very particularly preferably, together with the carbon atoms to which they are attached, represent a 6-membered carbocyclic ring which may be mono- or disubstituted, identically or differently, by fluorine, chlorine, methyl, nitro or cyano.
• R 3 very particularly preferably represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, methoxycarbonyl, ethoxycarbonyl, i-propoxycarbonyl, allyloxycarbonyl or phenoxycarbonyl.
• R 4 and R 5 independently of one another very particularly preferably represent hydrogen or the radicals -COR 6 , -COOR 7 or -SO 2 R 8 , where
• R 6 , R 7 and R 8 independently of one another very particularly preferably represent methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-pentyl, 2,2-dimethylpropyl , n-hexyl, n-heptyl, n-octyl; for 2-propenyl, 1-propenyl, 2-propynyl, for chloromethyl, 2-chloroethyl, trifluoromethyl, 2,2,2-trifluoroethyl; for methoxymethyl, methoxyethyl, ethoxymethyl, for each optionally one to three times, identical or different by methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy,
• X 1 and X 2 independently of one another very particularly preferably represent fluorine, chlorine, cyano, methyl or trifluoromethyl
• n and n independently of one another very particularly preferably represent 0 or 1, in particular 0
• Y very particularly preferably stands for -CH 2 -, -CH (CH 3 ) - or -CH 2 O-, in particular for -CH 2 - or -CH (CH 3 ) -
• one of the substituents R 4 or R 5 is hydrogen.
• Preferred groups of compounds according to the invention are in each case the substances of the formulas (IA) to (ID):
• R 1 , R 2 , R 3 , R 4 , R 5 , X 1 , X 2 , Y, m and n represent the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
• Preferred groups of compounds according to the invention are also in each case the substances of the formulas (IA-1) to (IA-8), (IB-1) to (IB-8), (IC-1) to (IC-8) and (ID -1) to (ID-8):
• R 1 , R 2 , R 3 , R 6 , R 7 and R 8 stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
• R 1 , R 2 , R 3 , R 6 , R 7 and R 8 stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
• R 1 , R 3 , R 6 , R 7 and R 8 stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
• R 1 , R 3 , R 6 , R 7 and R 8 stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings.
• hydrocarbon radicals such as alkyl or alkenyl - also in connection with heteroatoms such as alkoxy or alkylthio - are in each case straight-chain or branched as far as possible
• alkyleneoxy or -CH 2 O- is to be understood such that R 4 in formula (I) is linked to the oxygen of the alkyleneoxy or -CH 2 O radical
• R 4 as listed below:
• nitro derivatives of the formula (II) required as starting materials for carrying out the process (a) according to the invention are largely known (cf., for example, WO 95/31 448, DE-A-195 42 372, WO 93/04 580, WO 95 / 18 795 and WO 97/26 251) and / or by the processes specified there
• amino derivatives of the formula (1-1) required as starting materials for carrying out process (b) according to the invention are compounds according to the invention
• the compounds of the formula (III) which are also to be used as starting materials in process (b) according to the invention are generally known compounds of organic chemistry and / or can be obtained by generally known and customary processes
• the amino heterocycles of the formula (IV) required as starting materials for carrying out process (c) according to the invention are largely known (cf., for example, WO 95/31 448, DE-A-95 42 372, DE-A-22 49 162, WO 93 / 19 054, WO 94/21 617, J Med Chem 1989. 32, 1970-77, J Prakt Chem 1989. 331, 369-74, Tetrahedron 1971. 2581, J Org Chem 1952. 547, J Het Chem 1970. 81, J Org Chem 1981.
• R 4 " 1 , R 5 , X 1 , X 2 , Y, m and n have the meaning given above,
• the acid derivatives of the formula (VI) are also new. They are obtained by known or obtainable in a customary manner (see, for example, US
• X 1 , X 2 , Y, m and n have the meaning given above,
• R 5 " 1 represents the meanings of R 5 , except hydrogen
• the process (a) described above for the preparation of the compounds (I) is optionally carried out in the presence of a diluent.
• Alcohols such as methanol and ethanol, and mixtures of alcohols with water can preferably be used
• the reducing agent is generally used in excess
• reaction temperatures can be varied within a wide range in process (a) described above. In general, temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 100 ° C.
• Halogenated aliphatic or aromatic hydrocarbons, ethers or nitriles such as cyclohexane, toluene, chlorobenzene, chloroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile are preferably usable
• All customary proton acceptors can be used as bases.
• Alkali or alkaline earth metal hydroxides, alkali or alkaline earth metal carbonates or hydrogen carbonates or nitrogen bases are preferably usable.
• DABCO diazabicyclooctane
• DBN diazabicyclonones
• DBU diazabicycloundecene
• reaction temperatures can be varied within a wide range in the processes (a) and (b) described. In general, temperatures between -40 ° C and + 200 ° C, preferably between 0 ° C and 100 ° C.
• the end products are worked up and isolated in a generally known 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 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 e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of the Diplopoda e.g. Blaniulus guttulatus.
• Chilopoda for example, Geophilus carpophagus and Scutigera spec.
• Symphyla for example, Scutigerella immaculata.
• Thysanura for example Lepisma saccharina.
• Collembola for example Onychiurus armatus.
• anoplura e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
• Mallophaga e.g. Trichodectes spp., Damalinea spp.
• 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, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix,
• Pemphigus spp. Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopa- losiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettixcincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, spp Pseudococcus. , Psylla spp. From the order of the Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius,
• Hymenoptera e.g. Dip ⁇ on spp, Hoplocampa spp, Lasius spp, Monomo ⁇ um pharaonis, Vespa spp From the order of the Diptera e.g.
• Plant parasitic nematodes include, for example, Pratylenchus spp, Radopholus simihs, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp, Globodera spp, Meloidogyne spp, Aphelenchoides spp, Longidorus spp, X ⁇ hinema spp, Tnchchod
• the compounds of the formula (I) according to the invention are notable in particular for a high insecticide and aka ⁇ zide effect
• insects such as, for example, against the horseradish leaf beetle larvae (Phaedon cochlea ⁇ ae), the green rice leafhopper (Nephotettix cinct ⁇ ceps) and the caterpillars of the owl butterfly (Spodoptera frugiperda) or for combating plant-damaging ones
• mites for example 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.
• formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• extenders that is to say liquid solvents and / or solid carriers
• surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can also be used as auxiliary solvents.
• auxiliary solvents e.g. organic solvents
• aromatics such as xylene, toluene, or alkylnaphthalenes
• chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
• aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as
• Possible solid carriers are: e.g. Ammonium salts and natural rock flours, such as kaolins, clays, talc,
• Chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as highly disperse silica, 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 inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks;
• suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene Fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
• Possible dispersing agents are, for example, lignin sul
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
• the active 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.
• Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
• Fungicides are particularly favorable mixed partners:
• Pe Pe
• penconazole pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, proconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, Quintozen (PCNB), sulfur and sulfur preparations,
• Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamid, tricyclazole, tridemorph, triflorolizol, triflorolizol, triflorolizole,
• Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin,
• Insecticides / acaricides / nematicides Abamectin, AC 303 630, Acephat, Acrinathrin, Alanycarb, Aldicarb, Alphamethrin,
• Amitraz Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin,
• Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenprox, Fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb, HCH, Heptenophos, Hexaflumuron, Hexythiazox,
• Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron,
• Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetroion, Pyradaphophone, Pyrada phylophone Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos,
• 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 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 and storage pests, the active ingredient is characterized by an excellent residual effect 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 pests, but also in the veterinary sector against deep parasites (ectoparasites) such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair warmer, feather nooks and fleas
• deep parasites ectoparasites
• tick ticks leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair warmer, feather nooks and fleas
• ectoparasites such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair warmer, feather nooks and fleas
• Anoplurida for example Haematopinus spp, Lmognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp
• Nematoce ⁇ na and Brachycenna e.g. Aedes spp, Anopheles spp, Culex spp, Simu um spp, Eusimu um spp, Phlebotomus spp, Lutzomyia spp., Culicoides spp, Chrysops spp, Hybomitra spp, Tabylotus spp, Atylotus spp , Haematopota spp, Phihpomyia spp., Braula spp, Musca spp, Hydrotaea spp, Stomoxys spp, Haematobia spp, Morelha spp, Fannia spp, Glossina spp, Calliphora spp, Luci a spp, Chrysomyia spp, Wohlfahrtia spp, Sarestrophaga s
• Actinedida Prostigmata
• Acaridida e.g. 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,
• 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, drinks, 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
• the active compounds of the formula (I) can be formulated (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 Apply up to 10,000-fold dilution or use it as a chemical bath
• Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
• Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucihegus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
• 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.
• active ingredients as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or
• Pastes can be applied.
• 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, if appropriate, color - substances and pigments as well as 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 the 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 wt .-% of the active ingredient, based on the material to be protected
• the organic chemical solvents used are preferably oily or oil-like 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 alkyl benzene, are used as such volatile, water-insoluble, oily and oil-like solvents
• Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range are advantageous from 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and the like
• Evaporation rate 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 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.
• the known organic-chemical binders are the water-thinnable and / or synthetic resins soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, e.g. polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin.
• binders consisting of or containing an acrylate resin, a vinyl resin, e.g. polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumar
• 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-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 organic chemical binder.
• binder mentioned can be replaced by a fixative (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 glycol or high molecular weight glycerol oleate, glycerol oleate, glycerol oleate, and glycerol oleate - ether, glycerol ester and p-toluenesulfonic acid ester
• 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 preservation is achieved by 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.
• the additional admixing partners are preferably the insecticides and fungicides mentioned in WO 94/29 268.
• the compounds mentioned in this document are an integral part of the present application.
• insecticides such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, per- methrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron and triflumuron, and fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, Tebucon - Azoles, Cyproconazole, Metconazole, Imazalil, Dichlorfluanid, Tolylfluanid, 3-Iodo-2-propynyl-butylcarbamate, N-Octyl-isothiazolin-3-one and 4,5-Dichlor-N-octylisothiazo-lin-3-one
• the active compounds according to the invention also have a strong microbicidal action and can be used practically to combat unwanted microorganisms.
• the active ingredients are suitable for use as crop protection agents, in particular as fungicides.
• Fungicidal agents in crop protection are used to combat plasmidiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes
• Bactericidal agents are used in crop protection to combat Pseudomonadaeae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
• Some pathogens of fungal and bacterial diseases that fall under the generic names listed above may be mentioned as examples, but not by way of limitation:
• Xanthomonas species such as, for example, Xanthomonas campestris pv. Oryzae
• Pseudomonas species such as, for example, Pseudomonas syringae pv. Lachrymans
• Erwinia species such as, for example, Erwinia amylovora;
• Pythium species such as, for example, Pythium ultimum
• Phytophthora species such as, for example, Phytophthora infestans
• Pseudoperonospora species such as, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis;
• Plasmopara species such as, for example, Plasmopara viticola
• Bremia species such as, for example, Bremia lactucae
• Peronospora species such as, for example, Peronospora pisi or P. brassicae;
• Erysiphe species such as, for example, Erysiphe graminis
• Sphaerotheca species such as, for example, Sphaerotheca Sleepiginea
• Podosphaera species such as, for example, Podosphaera leucotricha
• Venturia species such as, for example, Venturia inaequalis
• Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
• Cochliobolus species such as, for example, Cochliobolus sativus
• Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
• Uromyces species such as, for example, Uromyces appendiculatus
• Puccinia species such as, for example, Puccinia recondita
• Sclerotinia species such as, for example, Sclerotinia sclerotiorum
• Tilletia species such as, for example, Tilletia caries
• Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
• Pellicularia species such as, for example, Pellicularia sasakii;
• Pyricularia species such as, for example, Pyricularia oryzae
• Fusarium species such as, for example, Fusarium culmorum
• Botrytis species such as, for example, Botrytis cinerea
• Septoria species such as, for example, Septoria nodorum
• Leptosphaeria species such as, for example, Leptosphaeria nodorum;
• Cercospora species such as, for example, Cercospora canescens; Alternaria species, such as, for example, Alternaria brassicae, Pseudocercosporella species, such as, for example, Pseudocercosporella herpotrichoides.
• the active compounds according to the invention can, when used as fungicides as such, in
• the seeds of the plants can also be treated.
• Application forms can be varied over a wide range: they are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight
• amounts of active ingredient are generally from 0.001 to
• active ingredient concentrations 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, are required at the site of action.
• logP decimal logarithm of the n-octanol / water distribution coefficient, determined by HPLC analysis on reversed phase with H 2 O / CH 3 CN Table B
• Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.
• the death rate is determined in%. 100% means that all cicadas have been killed, 0% means that no cicadas have been killed
• the compounds of the preparation examples Al, A-2, A-4, A-5, A-6, A-9 and Al 1 each achieve a death rate of 100% at an exemplary active ingredient concentration of 0.1% 6 days
• Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with horseradish leaf beetle larvae (Phaedon cochlea ⁇ ae) while the leaves are still moist
• the death rate is determined in%. 100% means that all the beetle larvae have been killed, 0% means that no beetle larvae have been killed
• the compounds of preparation examples Al, A-2, A-4, A-5, A-6, A-7, A-8, A-9, A-10 and Al 1 for example, produce an active compound concentration of 0.1% each a mortality of 100% after 7 days
• 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 death rate is determined in%. 100% means that all the caterpillars have been killed, 0% means that none of the caterpillars have been killed
• the compounds of preparation examples Al, A-2, A-4, A-5, A-6, A-7, A-8, A-9, A-10 and Al 1 for example, produce an active compound concentration of 0.1% each a mortality of 100% after 7 days
• the effect is determined in%. 100% means that all spider mites have been killed, 0% means that none of the spider mites have been killed
• the compound according to preparation example A-10 causes a death of 95% and the compound according to preparation example A-1 1 causes a death rate of 100%, in each case after 7 days
• test tubes About 20 Lucilia cuprina larvae are placed in a test tube which contains approx. 1 cm ⁇ horse meat and 0.5 ml of the active ingredient preparation to be tested. The effectiveness of the active ingredient preparation is determined after 24 hours and 48 hours.
• the test tubes are placed in beakers with a sand-covered bottom transferred After another 2 days, the test tubes are removed and the dolls are paid out
• 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 have hatched normally
• the compounds of preparation examples A-9 and A-10 for example, each show a 100% action at an exemplary active ingredient concentration of 100 ⁇ g.
• the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred to dishes and stored in an air-conditioned room. The effect is determined by the inhibition of egg laying. 100% means that no tick has laid

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Plural Heterocyclic Compounds (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Quinoline Compounds (AREA)
• Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
• Pyridine Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

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Citations (9)

• 1997
  • 1997-06-26 DE DE19727162A patent/DE19727162A1/de not_active Withdrawn
• 1998
  • 1998-06-15 CN CN98806614A patent/CN1261356A/zh active Pending
  • 1998-06-15 KR KR1019997011685A patent/KR20010013673A/ko not_active Application Discontinuation
  • 1998-06-15 EP EP98930804A patent/EP0991631A1/de not_active Withdrawn
  • 1998-06-15 AU AU81111/98A patent/AU8111198A/en not_active Abandoned
  • 1998-06-15 TR TR1999/03230T patent/TR199903230T2/xx unknown
  • 1998-06-15 ID IDW991658A patent/ID24079A/id unknown
  • 1998-06-15 WO PCT/EP1998/003592 patent/WO1999000375A1/de not_active Application Discontinuation
  • 1998-06-15 BR BR9810941-3A patent/BR9810941A/pt not_active Application Discontinuation
  • 1998-06-15 JP JP50524999A patent/JP2002512632A/ja active Pending

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