EP0915887A1 - N-isothiazolyl-(thio)amides substitues - Google Patents

N-isothiazolyl-(thio)amides substitues

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Publication number
EP0915887A1
EP0915887A1 EP97936642A EP97936642A EP0915887A1 EP 0915887 A1 EP0915887 A1 EP 0915887A1 EP 97936642 A EP97936642 A EP 97936642A EP 97936642 A EP97936642 A EP 97936642A EP 0915887 A1 EP0915887 A1 EP 0915887A1
Authority
EP
European Patent Office
Prior art keywords
fluorine
alkyl
substituted
atoms
chlorine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP97936642A
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German (de)
English (en)
Inventor
Markus Heil
Thomas Bretschneider
Gerd Kleefeld
Christoph Erdelen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
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Bayer AG
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Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of EP0915887A1 publication Critical patent/EP0915887A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides

Definitions

  • the present invention relates to new N-isothiazolyl (thio) amides, several processes for their preparation and their use for controlling animal pests.
  • N-isothiazolylamide derivatives have insecticidal properties (cf. e.g. EP-A 0 623 282 and WO-A 95/31448).
  • Het represents an optionally substituted heterocycle
  • R represents hydrogen, alkyl, haloalkyl, alkoxyalkyl, alkylcarbonyl, alkylsulfonyl, in each case optionally substituted arylcarbonyl, arylsulfonyl or arylalkyl or optionally substituted cycloalkyl,
  • X represents oxygen or sulfur
  • Y for optionally substituted alkylene, alkenylene, alkyleneoxy or
  • A represents optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl or an optionally substituted heterocycle
  • Alk stands for alkyl or the group MO-CO-CH -, -, where M stands for an alkali metal (such as sodium or potassium),
  • the new substituted N-isothiazolyl- (thio) amides of the formula (I) are very good for combating animal pests, in particular insects, arachnids and nematodes, which are used in agriculture, in forestry, in the protection of stocks and materials as well as in the hygiene sector are suitable.
  • Het represents an optionally mono- to trisubstituted, identically or differently substituted 5- or 6-membered heterocycle having 1 or 2 heteroatoms, such as N, S and O atoms, the substituents being
  • R preferably represents hydrogen, C * -C 4 -alkyl C, -C 4 -haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C 4 -alkoxy-C r C -alkyl, C , -C 4 alkyl carbonyl,
  • C, -C 4 -Alkylsulfonyl each optionally monosubstituted to trisubstituted, identically or differently, phenylcarbonyl, phenylsulfonyl or benzyl, the substituents in each case being halogen, nitro, cyano, C * -C 4 -alkyl, C * -C *, - Haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and
  • X preferably represents oxygen or sulfur
  • Y preferably represents C, -C 6 -alkylene, C, -C 6 -hydroxyalkylene, C, -C 4 -alkoxy-
  • C - C 6 -alkylene C j -C ⁇ alkylcarbonyloxy-C Cs-alkylene, cyano-C r C 6 -alkylene, C r C 4 -halogenated alkylene with 1 to 5 identical or different halogen atoms, such as fluorine and Chlorine atoms; optionally one to three times, identical or different substituted by fluorine, chlorine or methyl
  • A is preferred
  • halogen nitro, cyano, thiocarbamoyl, C r C 4 alkyl, C r C 4 - haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C ] -C 4 -alkoxy, C, -C 4 -alkoxy- C, -C 4 -alkyl, C, -C 4 -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C r C 4 - alkylthio, C r C 4 haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C r C 4 -
  • Halogen atoms such as fluorine and chlorine atoms, C, -C 4 -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms and C, -C 4 -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and Chlorine atoms, and one optionally present in the heterocycle
  • NH group can be substituted for the hydrogen atom by C, -C 6 alkyl, C, -C 6 alkylcarbonyl or phenylsulfonyl, which in turn may optionally be substituted by C- -C 6 alkyl, halogen, C, -C 4 haloalkyl 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms, C, -C 4 alkoxy or C, -C 4 -
  • Halogenalkoxy is substituted with 1 to 5 identical or different halogen atoms, such as fluorine or chlorine atoms,
  • Chlorine atoms C, -C 4 -alkoxy-C * -C 4 -alkyl, C * -C 4 -alkoxy,, -C 4 - haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C j - C 4 -Alkylth ⁇ o, C * -C 4 - haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C 4 -alkylsulfinyl, C r C 4 -
  • R 1 for hydrogen, C, -C 8 alkyl, C, -C 4 haloalkyl with 1 to
  • halogen atoms such as fluorine and chlorine atoms, for optionally mono- or polysubstituted, identically or differently, C 3 -C 7 -cycloalkyl substituted by halogen or C r C 4 -alkyl or for optionally single to triple, identical or different substituted
  • Phenyl, where 4 alkoxy, suitable substituents are halogen, C r C 4 alkyl or C, -C into question,
  • R "and R " 1 are the same or different and are hydrogen or C, -C 4 alkyl
  • R 5 for C * -C 6 alkyl or for optionally single to triple, identical or different, by halogen, Nitro, cyano, thiocarbamoyl, C, -C 4 alkyl, C r C 4 - haloalkyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C
  • Halogen atoms such as fluorine and chlorine atoms, C, -C 4 -alkylthio, C r C 4 -haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C r C 4 -alkylth ⁇ o-C r C 4 -alkyl , C, -C 4 -
  • R 6 and R 7 are the same or different and are hydrogen, C, -C 6 -alkyl or phenyl which is monosubstituted to trisubstituted by identical or different means
  • halogen atoms such as fluorine and
  • Q particularly preferably stands for one of the groupings
  • Z 1 , Z 2 and Z ' are the same or different and represent hydrogen, chlorine, bromine, nitro, methyl, ethyl, n- or i-propyl, n-, I-, s- or t-butyl, CH 2 F, CHF 2 , CF 3 , CH 2 C1, CH 2 Br, CHCICH, methoxy, ethoxy, methoxymethyl or ethoxymethyl
  • R particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl
  • X particularly preferably represents oxygen or sulfur
  • Y particularly preferably represents one of the groups
  • A is particularly preferred (1) for optionally mono- to trisubstituted, identically or differently substituted phenyl, suitable substituents being halogen, nitro, cyano, C, -C 12 alkyl, C, -C ] 2 haloalkyl having 1 to 5 identical or different Halogen atoms, such as fluorine and chlorine atoms, C * -C 4 alkoxy, C * -C 4 haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C 4 alkylthio, C, -C 4 -Halogenalkylth ⁇ o with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C 2 -C 4 alkenyl, C 2 -C 4 haloalkenyl with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, the groupings
  • halogen nitro, cyano, thiocarbamoyl, C r C 4 alkyl, C, -C 4 - haloalkyl having 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C * - C 4 -alkoxy, C * -C, -alkoxy- C, -C 4 -alkyl, C ] -C 4 -haloalkoxy with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C - C - alkylthio, C ] -C 4 haloalkylthio with 1 to 5 identical or different halogen atoms, such as fluorine and chlorine atoms, C, -C 4 -
  • CF 3 -CHF ,, -CH 2 CF 3 , -CH 2 -CF, -CHF 2> -CH (CF 3 ) -CH 3 , -OCF 3 , -OCHF 2 , -OCH 2 CF 3 , -O- CH 2 -CF 2 -CF 3 , -OCH 2 -CF 2 -CHF 2 , -O-CH (CF 3 ) -CH 3 ; -SCF 3 ; and in each case optionally mono- or disubstituted, identically or differently substituted phenyl, phenoxy or phenylthio, suitable substituents
  • R 1 for hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for optionally up to five times, identically or differently, C 3 - substituted by fluorine, chlorine, bromine or methyl C 7 -cycloalkyl or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy or ethoxy being suitable as substituents, R 2 and R 3 are identical or different and represent hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,
  • R 4 for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for optionally one to five times (preferably one to three times), the same or different by fluorine, chlorine, bromine or methyl substituted C 3 -
  • R 3 represents C * -C 4 alkyl or benzyl which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents
  • R and R are the same or different and represent hydrogen, C, -C 4 alkyl or phenyl which may be monosubstituted to trisubstituted identically or differently, the substituents being fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, trifluoromethyl , Methoxy or trifluoromethoxy come into question
  • Z 1 and 7? are identical or different and represent hydrogen, chlorine, bromine, nitro, methyl, ethyl, methoxy or ethoxy
  • R very particularly preferably represents hydrogen, methyl, ethyl, methoxymethyl, ethoxymethyl, methylcarbonyl, phenylcarbonyl or methylsulfonyl
  • X very particularly preferably represents oxygen or sulfur
  • R 1 represents hydrogen, methyl or ethyl
  • R 2 and R 3 are the same or different and represent hydrogen or methyl
  • R 4 represents methyl or ethyl
  • R 5 represents methyl, ethyl, n- or l-propoyl, n-, 1-, s- or t-butyl or benzyl which is optionally monosubstituted to trisubstituted identically or differently in the ring, fluorine, chlorine, bromine being the substituents , Nitro, cyano, methyl, ethyl, methoxy or ethoxy come into question
  • Preferred compounds according to the invention are substances of the formulas (IA) to
  • R, Z 1 and Z 2 stand for the abovementioned general, preferred, particularly preferred and very particularly preferred meanings and
  • X 1 , X 2 , X 3 , X 4 and X 5 stand for the substituents mentioned above under A in general, preferably, particularly preferably and very particularly preferably for the phenyl or phenoxy radical and
  • X -1, X v 2 ", X" 1 and X can also each represent hydrogen
  • Another preferred group of compounds are those of the formulas (IA) to (ID), in which the phenoxy radical is para to the NR-CO-CH 2 or NR-CS-CH 2 group, among these compounds those are particularly preferred in which the substituents X 1 , X 2 , X 3 and X 4 are hydrogen
  • 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
  • Table 2 contains compounds of the general formula (I), in which
  • Table 3 contains compounds of the general formula (I), in which
  • Table 4 contains compounds of the general formula (I), in which
  • Table 5 contains compounds of the general formula (I), in which
  • Table 6 contains compounds of the general formula (I), in which
  • Table 7 contains compounds of the general formula (1), in which
  • Table 8 contains compounds of the general formula (I), in which
  • Table 9 contains compounds of the general formula (I), in which
  • reaction sequence can be represented by the following reaction scheme
  • aminoisothiazoles of the formula (II) to be used as starting materials in processes (a) and (c) according to the invention are known (cf., for example, GB 1568377, J Chem Res Synop 1989. 29, DE-A 2713573, Can J Chem 1973 (51 ), 1742 or JP 05070469) and / or can be produced by known methods (cf. e.g. the above-mentioned references)
  • Het has the meaning given above, first reacted with hydrogen sulfide in the presence of a base, such as pyridine or t ⁇ ethylamine,
  • an oxidizing agent such as, for example, H-.O-, bromine or sodium hypochlorite
  • the acid halides of the formula (III) which are also to be used as starting materials in process (a) according to the invention are generally known compounds of organic chemistry.
  • shark preferably represents chlorine or bromine
  • dithioesters of the formula (IV) which are also to be used as starting materials in process (c) according to the invention are known (cf. for example tetrahedron)
  • Alk preferably represents methyl
  • Suitable diluents for carrying out process (a) according to the invention are, if appropriate, halogenated aliphatic or aromatic hydrocarbons, ethers or nitols, such as, for example, cyclohexane, toluene, chlorine. benzene, choroform, dichloromethane, dichloroethane, dioxane, tetrahydrofuran, diethyl ether or acetonitrile.
  • Alkali or alkaline earth metal hydroxides, alkali or alkaline earth metal carbonates or bicarbonates or nitrogen bases are preferably usable.
  • Examples include sodium hydroxide, calcium hydroxide, potassium carbonate, sodium hydrogen carbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclonones (DBN) and diazabicycloundecene (DBU).
  • reaction temperatures can be varied within a wide range in process (a). In general, temperatures between -40 ° C and + 200 ° C, preferably between 0 ° C and 100 ° C.
  • aminoisothiazoles of the formula (II) in the form of their hydrohalides, such as, in particular, as hydrochlorides.
  • Preferred sulfurization agents when carrying out process (b) according to the invention are: phosphorus pentasulfide or Lawesson®
  • Suitable diluents for carrying out process (b) according to the invention are preferably hydrocarbons, such as toluene, xylene, tetralin, hexane or cyclohexane.
  • reaction temperatures can be varied within a substantial range when carrying out process (b) according to the invention. In general, temperatures between 0 ° C and 200 ° C, preferably between 20 ° C and 150 ° C.
  • temperatures between 0 ° C and 200 ° C, preferably between 20 ° C and 150 ° C.
  • sulfurizing agent When carrying out process (b) according to the invention, between 1 and 3 mol, preferably between 1 and 2 mol, of sulfurizing agent are generally employed per mol of compound of the formula (Ia).
  • Working up is carried out by customary methods
  • Halogenated aliphatic or aromatic hydrocarbons such as methylene chloride, dichloroethane, cyclohexane, toluene or chlorobenzene, can preferably be used
  • reaction temperatures can be carried out when carrying out the inventive reaction temperatures.
  • Process (c) can be varied over a wide range. In general, temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 120 ° C.
  • the active ingredients are suitable for good plant tolerance and favorable warm-blood toxicity to control animal pests, especially insects, arachnids and nematodes, which are used in agriculture, in forests, in
  • Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber
  • Symphyla e.g. Scutigerella immaculata
  • Thysanura e.g. Lepisma saccharina
  • From the order of the Collembola for example Onychiurus armatus
  • From the order of the Orthoptera for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
  • From the order of the Dermaptera for example, Forficula auricularia.
  • From the order of the Isoptera for example Reticulitermes spp ..
  • Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
  • Heteroptera e.g. Eurygaster spp., Dysdercus intermedius
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum,
  • Leptinotarsa decemlineata Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatordimidhmpphppm, spp. , Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp.,
  • Niptus hololeucus Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Diptera e.g. Aedes spp., Anopheles spp., Culex spp.
  • Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp.
  • Dermanyssus gallinae Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonaia 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.,
  • the compounds of the formula (I) according to the invention are notable in particular for outstanding insecticidal activity.
  • 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 and preferably 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 foaming agents
  • organic solvents can, for example, also be used as auxiliary solvents.
  • Liquid solvents are essentially aromatics, such as xylene, toluene, or alkylnaphthanes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methylsobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water
  • Solid carrier materials are, for example, ammonium salts and natural rock powders, such as kaolins, alumina talc, chalk, quartz, attapulgite, montmole lumps or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, and solid carrier materials for granules are possible, for example broken and fractionated natural rocks such as calcite, marble, pumice, sepio th, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, as emulsifying and / or foam-generating agents are possible
  • B non-ionic and anionic emulsifiers such as polyoxyethyl en-
  • Fatty acid esters are, for example, lignin sulfite waste liquors 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 also natural phosphides, such as cephalins and lecithins and synthetic phosphophides, can be used.
  • Other additives can be mineral and vegetable oils Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as Ahza ⁇ n, azo and metal phthalocyanine, are used, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc become
  • the formulations generally contain between 0.1 and 95% by weight
  • Active ingredient preferably between 0.5 and 90%
  • the active substance according to the invention can, 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, stonlants, bactericides, acaecides, nematicides, fungicides, regulate growth
  • other active substances such as insecticides, attractants, stonlants, bactericides, acaecides, nematicides, fungicides, regulate growth
  • Insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and the like
  • copper preparations such as: copper hydroxide, copper naphthenate,
  • Mancopper Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metsulfovax, Myclobutanil,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen,
  • Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, tecloftalam, copper sulfate and other copper preparations
  • Fenamiphos Fenazaquin, Fenbutatinoxid, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipronil, Fluazinam, Flucycloxuron, Flucythrinat, Flufenoxuron, Flufenothionx, Fhrionophon, Fufionophon, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fufion, Fuf
  • Imidacloprid Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin, Lambda-cyhalothrin, Lufenuron,
  • Parathion A Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet,
  • the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight
  • the application takes place in a customary manner adapted to the application forms
  • the active 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 product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas.
  • animal parasites ectoparasites
  • tick ticks leather ticks
  • rough mites rough mites
  • running mites running mites
  • flies stinging and licking
  • parasitic fly larvae lice, hair lice, Featherlings and fleas.
  • Nematocerina and Brachycerina for example Aedes spp., Anopheles spp., Culex spp., Simulium spp, Eusimulium spp., Phlebotomus spp., Lutzomyia spp, Culicoides spp., Chrysops spp., Hybomitraus spp., Atylotan spp., Atylotan 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
  • Mesostigmata e.g. Argas spp, Ornithodorus spp, Otobius spp, Ixodes spp, Amblyomma spp, Boophilus spp, Dermacentor spp, Haemophysahs spp, Hyalomma spp, Rhipicephalus spp, Dermanyssus spp, Rail etia spp, Sternonyssoma spp, Sternonyssoma spp, Sternonyssoma spp.
  • the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are agricultural animals such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees , other pets such as dogs, cats, house bird, aquarium fish and so-called experimental animals such as hamsters,
  • arthropods which are agricultural animals such as, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees , other pets such as dogs, cats, house bird, aquarium fish and so-called experimental animals such as hamsters,
  • 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 help of shaped bodies containing active ingredients, such as collars , Ear tags, tail tags, ghedma bands, holsters, marking devices, etc
  • 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
  • insects may be mentioned by way of example and preferably, but without limitation
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes 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,
  • 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, e.g. 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 further 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 from 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 ol-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 alkylbenzene, are used as such slightly 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 of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil are advantageous and the like for use
  • liquid aliphatic hydrocarbons with a boiling range from 180 to 210 ° C. or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C. and / or spindeol and / or monochlomaphthalene, preferably ⁇ -monochloronaphthalene, are used.
  • organic semi-volatile oily or oil-like 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.
  • the known organic-chemical binders are synthetic resins which are known to be water-thinnable and / or soluble or dispersible or dispersible or emulsifiable in the organic-chemical solvents used, and / or binding drying oils, in particular binders consisting of or containing an acrylic resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances of up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, odorants tien and inhibitors or corrosion protection agents and the like are 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.
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to volatilize the active ingredients and to crystallize or prevent falling 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 t ⁇ butyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleatolecies such as butyl oleate or glycerol - Kolether, 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 ethyl enbenzophenone
  • 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 by large-scale impregnation processes, eg vacuum, double vacuum or printing processes
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides
  • Possible additional admixing partners are preferably the insecticides and fungicides mentioned in WO 94/29 268.
  • the compounds mentioned in this document are an express component of the present application
  • Insecticides such as chlorpyphos, phoxim, silafluofin, alphamethrin, cypermethrin, deltamethin, permethrin, imidacloprid, hexaflumuron, triflizolez, as well as fazonazole, are as very particularly preferred Tebuconazole, cyproconazole, metconazole, imazalil, dichlorfluanid, tolylfluanid,
  • reaction mixture is taken up in water / ethyl acetate and the organic phase is washed several times with 10% strength sodium hydroxide solution and concentration gives a viscous residue which is purified by chromatography on silica gel with methylene chloride / ethyl acetate (20 l) as the eluent
  • 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 cochleariae) 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
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and with caterpillars of the owl butterfly
  • 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
  • Rice seedlings (Oryza sativa) are treated with T in the active ingredient preparation of the desired concentration and with larvae of the green rice leafhopper
  • the death rate is determined in%. 100% means that all cicadas have been killed, 0% means that no cicadas have been killed

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

L'invention concerne de nouveaux N-isothiazolyl-(thio)amides de la formule (I) dans laquelle Q désigne le groupement (a), Het désignant un hétérocycle éventuellement substitué, et R, X, Y et A on la signification donnée dans la description. L'invention concerne en outre plusieurs procédés permettant de les préparer et leur utilisation pour lutter contre les parasites animaux.
EP97936642A 1996-07-31 1997-07-18 N-isothiazolyl-(thio)amides substitues Withdrawn EP0915887A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19630814A DE19630814A1 (de) 1996-07-31 1996-07-31 Substituierte N-Isothiazolyl-(thio)amide
DE19630814 1996-07-31
PCT/EP1997/003858 WO1998005670A1 (fr) 1996-07-31 1997-07-18 N-isothiazolyl-(thio)amides substitues

Publications (1)

Publication Number Publication Date
EP0915887A1 true EP0915887A1 (fr) 1999-05-19

Family

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Application Number Title Priority Date Filing Date
EP97936642A Withdrawn EP0915887A1 (fr) 1996-07-31 1997-07-18 N-isothiazolyl-(thio)amides substitues

Country Status (9)

Country Link
EP (1) EP0915887A1 (fr)
JP (1) JP2000515530A (fr)
KR (1) KR20000029574A (fr)
CN (1) CN1232464A (fr)
AU (1) AU3940397A (fr)
BR (1) BR9710897A (fr)
DE (1) DE19630814A1 (fr)
IL (1) IL128098A0 (fr)
WO (1) WO1998005670A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19846008A1 (de) 1998-10-06 2000-04-13 Bayer Ag Phenylessigsäure-heterocyclylamide
GB0002041D0 (en) * 2000-01-28 2000-03-22 Zeneca Ltd Chemical compounds
GB0002036D0 (en) * 2000-01-28 2000-03-22 Zeneca Ltd Chemical compounds
GB0002040D0 (en) * 2000-01-28 2000-03-22 Zeneca Ltd Chemical compounds
PE20010830A1 (es) 2000-01-28 2001-09-06 Syngenta Ltd Derivados de azol insecticidas o fungicidas y composiciones que los comprenden
GB0002029D0 (en) * 2000-01-28 2000-03-22 Zeneca Ltd Chemical compounds
GB0012806D0 (en) * 2000-05-25 2000-07-19 Zeneca Ltd Chemical compounds
CN109061155B (zh) * 2018-09-21 2021-05-11 中国烟草总公司郑州烟草研究院 一种检测甲霜灵的试纸条及其制备方法和应用

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3562285A (en) * 1968-03-06 1971-02-09 American Cyanamid Co Ethyl 3-(n-substituted-amino)-4h-pyrrolo (3,4-c)isothiazole-5(6h)-carboxylates
DE2248231A1 (de) * 1972-10-02 1974-04-11 Basf Ag 3-aminoisothiazolo eckige klammer auf 3,4-d eckige klammer zu pyrimidine
DE2713573A1 (de) * 1977-03-28 1978-10-05 Basf Ag 4,5-disubstituierte thiazole und verfahren zu ihrer herstellung
GB1568377A (en) * 1977-03-31 1980-05-29 Ici Ltd 3-aminothieno isothiazoles and processes for their production
EP0623282A1 (fr) * 1993-05-05 1994-11-09 Shell Internationale Researchmaatschappij B.V. Procédés et composés pesticides
JPH10503171A (ja) * 1994-05-17 1998-03-24 ダウエランコ Ｎ−（５−イソチアゾリル）アミド有害生物防除剤

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9805670A1 *

Also Published As

Publication number Publication date
KR20000029574A (ko) 2000-05-25
JP2000515530A (ja) 2000-11-21
AU3940397A (en) 1998-02-25
CN1232464A (zh) 1999-10-20
BR9710897A (pt) 1999-08-17
DE19630814A1 (de) 1998-02-05
IL128098A0 (en) 1999-11-30
WO1998005670A1 (fr) 1998-02-12

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