Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
• • 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
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
  • A01N43/52—1,3-Diazoles; Hydrogenated 1,3-diazoles condensed with carbocyclic rings, e.g. benzimidazoles
• • 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
  • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
  • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
  • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
  • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
  • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
  • C07D235/08—Radicals containing only hydrogen and carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
  • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
  • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
  • C07D235/10—Radicals substituted by halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
  • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
  • C07D491/04—Ortho-condensed systems

Definitions

• the invention relates to new substituted berzimidazoles, several processes for their preparation and their use as pesticides.
• R 1 represents hydrogen, alkyl, haloalkyl, cycloalkyl or optionally substituted aryl,
• R 2 represents hydrogen, alkyl, haloalkyl, cycloalkyl or optionally substituted aryl,
• R 3 represents fluoroalkyl
• X 1 , X 2 , X 3 and X 4 independently of one another each represent hydrogen, halogen, cyano, nitro, each optionally substituted alkyl, Alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, for optionally substituted, annexed dioxyalkylene, for hydroxycarbonyl, alkylcarbonyl, alkoxycarbonyl, cycloalkyloxycarbonyl, for optionally substituted amino or aminocarbonyl or for optionally substituted aryl, aryloxy, arylthio, arylsulfonyl, arylsulfonyl, arylsulfonyl, Arylcarbonyl, aryloxycarbonyl, arylazo or aiyltoomethylsulfonyl, but at least one of the substituents X 1 , X 2 , ⁇ 3 and X 4 is different
• R 1 represents hydrogen, alkyl, haloalkyl, cycloalkyl or optionally substituted aryl
• R 2 represents hydrogen, alkyl, haloalkyl, cycloalkyl or optionally substituted aryl
• R 3 represents fluoroalkyl
• X 1 , X 2 , X 3 and X 4 independently of one another each for hydrogen, halogen, cyano, nitro, for each optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or cycloalkyl, for optionally substituted, fused-on dioxyalkylene, for hydroxycarbonyl, alkylcarbonyl ,, are alkoxycarbonyl cycloalkyloxycarbonyl for each case optionally substituted amino or aminocarbonyl, or represents in each case optionally substituted aryl, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylsulfonyloxy, arylcarbonyl, aryloxycarbonyl, arylazo or arylthiomethylsulphonyl, but where at least one of the substituents X 1, X 2, X 3 and
• the substituted benzimidazoles according to the invention are generally defined by the formula (I).
• Compounds of formula (I) are preferred in which
• R 3 represents straight-chain or branched fluoroalkyl having 1 to 8 carbon atoms and 1 to 17 fluorine atoms and X 1 , X 2 , X 3 and X 4 independently of one another each for hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, for straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 8 carbon atoms, for cycloalkyl having 3 to 8 carbon atoms, for each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 6 carbon atoms and 1 to 13 identical or different halogen atoms or for optionally single or multiple, identical or different, by halogen and / or straight-chain or branche
• Phenyl or naphthyl may be mentioned as aryl radicals.
• R 1 for hydrogen, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, for
• R 2 for hydrogen, for straight-chain or branched alkyl having 1 to 4 carbon atoms, for straight-chain or branched haloalkyl with 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms, for cycloalkyl with 3 to 6 carbon atoms or for optionally single to triple, the same or differently substituted phenyl, where the phenyl substituents mentioned in R 1 are suitable,
• R 3 represents straight-chain or branched fluoroalkyl having 1 to 4 carbon atoms and 1 to 9 fluorine atoms and X 1 , X 2 , X 3 and X 4 independently of one another each represent hydrogen, chlorine, bromine, cyano, nitro, in each case straight-chain or branched alkyl , Alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl each having 1 to 4 carbon atoms, for cycloalkyl having 3, 5 or 6 carbon atoms, for each straight-chain or branched haloalkyl, haloalkoxy, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl each having 1 to 3 carbon atoms and 1 to 7 the same or different halogen atoms or for optionally monosubstituted to tetrasubstituted, identical or different, by halogen and
• Formula (II) provides a general definition of the 1H-benzimidazoles required as starting materials for carrying out the process according to the invention.
• R 3 , X 1 , X 2 , X 3 and X 4 preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the compounds of the formula (I) according to the invention.
• the 1H-benzimidazoles of the formula (II) are known or can be obtained analogously to known processes (cf., for example, J. Amer. Chem. Soc. 75, 1292 [1953]; US 3,576,818).
• Formula (III) provides a general definition of the halogen sulfonamides required to carry out the process according to the invention as starting products.
• R 1 and R 2 preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.
• Hal is preferably fluorine, chlorine or bromine, especially chlorine or bromine.
• the compounds of the formula (III) are generally known compounds of organic chemistry or can be obtained in analogy to generally known processes.
• Inert organic solvents are suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform or carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or benzonitrile; Am
• the process according to the invention can also be carried out in a two-phase system, such as, for example, water / toluene or water / dichloromethane, if appropriate in the presence of a suitable phase transfer catalyst.
• a suitable phase transfer catalyst such as: tetrabutylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tributyl-methylphosphonium bromide, trimethyl-C 13 -C 15 -alkylammoniumchlorid, trimethyl-C 13 / C 15 -alkylammoniumbromid, dibenzyl dimethyl ammonium methyl sulfate, dimethyl-C12 / C 14- alkyl-benzylammonium chloride, dimethyl-C 12 / C 14 -alkyl-benzylammonium bromide, tetrabutyl ammonium hydroxide, triethylbenz
• reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between -70 ° C and + 200 ° C, preferably at temperatures between 0 ° C and 130 ° C.
• the process according to the invention is usually carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• reaction auxiliary generally 1.0 to 5.0 mol, preferably 1.0 to 2.5 mol, of halogenosulfonamides of the formula (HI) and, if appropriate, 0.01 are employed per mol of 1H-benzimidazole of the formula (II) to 5.0 moles, preferably 1.0 to 3.0 moles, of reaction auxiliary.
• the reaction is carried out, worked up and isolated by known processes (see also the preparation examples).
• the end products of the formula (I) are purified using customary methods, for example by column chromatography or by recrystallization.
• the characterization takes place with the help of the melting point or with non-crystallizing compounds - in particular with regioisomer mixtures - with the help of proton nuclear magnetic resonance spectroscopy ( 1 H-NMR).
• the active substances are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• animal pests preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• the pests mentioned above include:
• Diplopoda e.g. Blaniulus guttulatus
• Chilopoda e.g. Geophilus carpophagus, Scutigera spec .
• Symphyla e.g. Scutigerella immaculata
• 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;
• Dermaptera e.g. Auricular forficula
• anoplura e.g. Phylloxera vastatrix, Pemphigus spp., Pediculus humanus corporis, Haematopinus spp., Linognathus spp .;
• Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci;
• Heteroptera e.g. Eurigaster 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, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphasceusi.
• Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Doralis fabae, Doralis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Phorodoniphasceusi.
• Nephotettix cincticeps Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp.,
• the active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites and endoparasites) such as shield ticks, leather ticks, Mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings, fleas and endoparasitic worms.
• animal parasites ectoparasites and endoparasites
• ectoparasites and endoparasites such as shield ticks, leather ticks, Mite mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, featherlings, fleas and endoparasitic worms.
• Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
• 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 tin can be used.
• 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 tin can be used.
• the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with other active compounds, such as insecticides, attractants, sterilants, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
• Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, etc.
• 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 we tion 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 ingredient concentration of the use forms can be from 0.0000001 to 95 percent by weight of active ingredient, preferably between 0.0001 and 1 percent by weight.
• the application takes place in a customary manner adapted to the application forms.
• the active ingredients When used against hygiene pests and pests of stored products, the active ingredients are distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
• the active compounds which can be used according to the invention are also suitable for controlling insects, mites, ticks, etc. in the field of animal husbandry and cattle breeding, better results, e.g. higher milk yields, higher weight, more beautiful animal fur, longer lifespan etc. can be achieved.
• the active ingredients which can be used according to the invention are used in this field in a known manner, for example by oral use in the form of tablets, capsules, drinkers or granules, by dermal or external use in the form of, for example, dipping (dipping), spraying (spraying), pouring on (pour-on or spot-on) and powdering, as well as by parenteral use in the form of, for example, injection and also by the "feed-through” method.
• use as a shaped body (collar, ear tag) is also possible.
• Example 1 The preparation and use of the active compounds according to the invention can be seen from the examples below. Production examples: Example 1:
• X represents hydrogen, fluorine, chlorine or bromine
• R 1 and R 4 may be the same or different from one another and each is hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halogen C 1 -C 6 alkyl, C 6 -C 10 aryl , COOH, CN, NCO, COO-C 1 -C 6 -alkyl, NH-C 1 -C 6 -alkyl, N (C 1 -C 6 -alkyl) 2 ,
• R 1 to R 4 have the meaning given above and
• R 5 for a protecting group
• R 1 to R 4 , R 5 and X have the meaning given above, splitting off the protective group R 5 from the intermediate of the above formula, reacting the OH compound thus obtainable with a base and thus 1,3-benzo-dioxoles of the above formula receives.
• R 1 , R 4 and X have the meaning given above. From these can be obtained by alkylation benzimidazole derivatives which are in the nitrogen atom with a
• R 1 for CF 3 , OCF 3 , SCF 3 , SO 2 -C 1 -C 6 alkyl which can be straight-chain or branched and can be completely or partially substituted by fluorine, N (CF 3 ) 2 , a phenyl or phenoxy radical CF 3 or CN in the 4-position and optionally further substituents, 1,1,2,3,3,3-hexafluoropropoxy, 1,1,2-trifluoro-2-chloroethoxy, 1,1,2,2-tetrafluoroethoxy , 1,1,2-trifluoro-2-chloro-ethylthio or 1,1,2,3,3,3-hexafluoropropylthio, regardless of which R 2 is F, Cl, Br, CN, CH 3 , OCF 3 , SO 2 -C 1 -C 6 - alkyl, which can be straight-chain or branched and can be completely or partially substituted by fluorine, COO-C 1 - C 6 alkyl,
• R 3 represents hydrogen, COCH 3 or COCF 3 , where R 1 and R 2 together can represent an -O-CFCl-CFCl-O radical, with the exception of those in EP-A 251 013 and EP-A 487 Compounds described 286 can be obtained by using a benzene derivative of the formula
• R 1 has the meaning given
• nitraniline can be used, for example of the formula
• R 1 has the meaning given above. react with a chlorinating or brominating agent, so insert a chlorine or bromine atom in the meta position to the nitro group and then reduce the nitro group.
• R 1 is a donor group in the 4-position to the two amino groups
• R 2 is an acceptor group, for example COO-C 1 -C 6 -alkyl, CN, CF 3 or SO 2 -C 1 -C 6 - Represents alkyl and R 3 is not hydrogen, for example, a benzene derivative of the formula
• the fluoroalkyl (en) group-containing o-phenylenediamines, in which R 3 is hydrogen, can first be converted into 2-trifluoromethylbenzimidazoles of the formula using trifluoroacetic acid
• R 4 represents hydrogen, alkyl, alkoxy or optionally substituted aryl
• R 5 for hydroxy, cyano or for optionally substituted alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, alkylthio, amino, aminocarbonyl, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, dialkoxyphosphonyl, (hetero) aryl, (hetero) arylcarbonyl, (hetero) Aryloxycarbonyl, (hetero) arylcarbonyloxy or (hetero) A ⁇ ylaminocarbonylaminocarbonyloxy stands and
• a means a suitable leaving group. Leaving groups are known to the person skilled in the art and are, for example, halogen, alkyl (alkoxy, aryl) sulfonyloxy, hydroxy or alkoxy. Examples
• Example 2b Analogously to example 1, 1,2-bis (1,1,2,3,3,3-hexafluoropropoxy) benzene was used to obtain the
• 3-trifluoromethyl-4-methoxy-acetanilide was initially 3-trifluoromethyl-4-methoxy-6-nitro-acetanilide (melting point 143-144 ° C.) and from it 3-trifluoromethyl-4-methoxy-6-amino -acetanilide (melting point 164-165 ° C).
• 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.
• the kill is determined in percent. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
• the following compound of the preparation examples shows superior activity over the prior art: 1, 7, 10, 11, 12, 13, 15, 17, 18 and 26.
• Example D Psoroptes ovis test:
• Emulsifier 35 parts by weight of nonylphenol polyglycol ether To produce a suitable preparation of active compound, 3 parts by weight of active compound are mixed with 7 parts of the solvent-emulsifier mixture mentioned above and the emulsion concentrate thus obtained is diluted with water to the desired concentration.
• Emulsifier 35 parts by weight of nonylphenol polyglycol ether To produce a suitable preparation of active compound, 3 parts by weight of active compound are mixed with 7 parts of the solvent-emulsifier mixture mentioned above and the emulsion concentrate thus obtained is diluted with water to the desired concentration.
• Emulsifier 35 parts by weight of nonylphenol polyglycol ether To produce a suitable preparation of active compound, 3 parts by weight of active compound are mixed with 7 parts of the solvent-emulsifier mixture mentioned above and the emulsion concentrate thus obtained is diluted with water to the desired concentration.

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Dentistry (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Plural Heterocyclic Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Applications Claiming Priority (3)

Publications (1)

Family

ID=6472321

Family Applications (1)

Country Status (10)

Families Citing this family (16)

Family Cites Families (14)

• 1992
  • 1992-11-06 DE DE4237597A patent/DE4237597A1/de not_active Withdrawn
• 1993
  • 1993-10-25 AU AU53378/94A patent/AU5337894A/en not_active Abandoned
  • 1993-10-25 US US08/424,256 patent/US5585395A/en not_active Expired - Fee Related
  • 1993-10-25 CA CA002148605A patent/CA2148605A1/en not_active Abandoned
  • 1993-10-25 BR BR9307393A patent/BR9307393A/pt not_active IP Right Cessation
  • 1993-10-25 HU HU9501330A patent/HU217906B/hu not_active IP Right Cessation
  • 1993-10-25 WO PCT/EP1993/002947 patent/WO1994011350A1/de not_active Application Discontinuation
  • 1993-10-25 JP JP6511644A patent/JPH08502983A/ja active Pending
  • 1993-10-25 EP EP93923546A patent/EP0667862A1/de not_active Withdrawn
  • 1993-10-25 KR KR1019950701763A patent/KR100298002B1/ko not_active IP Right Cessation

Non-Patent Citations (1)

Also Published As

Similar Documents

Legal Events