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WO2009156090A2 - Dérivés sulfurés de 1-azinyl-pyrazole utilisés en tant qu'insecticides - Google Patents

Dérivés sulfurés de 1-azinyl-pyrazole utilisés en tant qu'insecticides Download PDF

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Publication number
WO2009156090A2
WO2009156090A2 PCT/EP2009/004391 EP2009004391W WO2009156090A2 WO 2009156090 A2 WO2009156090 A2 WO 2009156090A2 EP 2009004391 W EP2009004391 W EP 2009004391W WO 2009156090 A2 WO2009156090 A2 WO 2009156090A2
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alkyl
haloalkyl
spp
alkoxy
general formula
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German (de)
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WO2009156090A3 (fr
Inventor
Hans-Georg Schwarz
Thomas Schenke
Achim Hense
Robert Velten
Simon MAECHLING
Stefan Werner
Eva-Maria Franken
Ulrich Görgens
Peter Lümmen
Ulrich Ebbinghaus-Kintscher
Arnd Voerste
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Bayer CropScience AG
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Bayer CropScience AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Definitions

  • the present invention relates to sulfur-derivatized 1-azinylpyrazoles, their use as insecticides and / or parasiticides, and processes for their preparation.
  • Another object of the present invention are various intermediates which are passed through in the preparation of the sulfur-derivatized 1-azinylpyrazoles invention.
  • Another object of the present invention are finally agents which contain such Azinylpyrazole.
  • DE 197 51 943 A1 relates to 1-methyl-5-alkylsulfonyl, 1-methyl-5-alkylsulfinyl and 1-methyl-5-alkylthio-substituted pyrazolylpyrazoles, processes for their preparation and their use as herbicides.
  • 5-amino-1-methyl-3- (methylsulfanyl) -1H-pyrazole-4-carbonitrile is passed through as an intermediate.
  • no insecticidal activity of this intermediate is disclosed.
  • EP 1 829 867 A1 generically discloses pharmaceutically active sulfur derivatized 1-azinylpyrazoles.
  • the object of the present invention is therefore to provide alternative insecticides and / or parasiticides which show an improved action or a broadened spectrum of action in comparison with the active compounds known from the prior art.
  • the problem is solved by special sulfur-derivatized 1-azinylpyrazoles.
  • the present invention therefore provides sulfur-derivatized 1-azinylpyrazoles of the general formula (I) or their N-oxides,
  • a 1 and A 2 are nitrogen or CR 3 ;
  • B is alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl,
  • R 1 and R 2 are each independently hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxyalkyl, alkylcarbonyl, haloalkylcarbonyl, cycloalkyl, cycloalkylalkyl, alkylsulfonyl, alkenyl, alkynyl, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, alkoxycarbonylalkyl; Phenalkyl which may optionally be monosubstituted or polysubstituted by identical or different substituents on the aromatic group by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; Heterocyclylalkyl which may optionally be mono- or polysubstituted by identical or different substituents on the heterocycle by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; Heteroaryl
  • R 4 and R 5 are each independently alkyl or together bridging alkylidene
  • R 6 is hydrogen or alkyl
  • X is phenyl, 2-pyridyl or 3-pyridyl, each substituted by one or more identical or different substituents selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenoxy, alkynyloxy, Cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, alkylsulfmyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, carboxamide, dialkylcarboxamide, trialkyl kylsilyl, nitro, amino, alkylamino, dialkylamino
  • Y is -S-, -S (O) -, -SO 2 -, or one of the following groupings
  • the compounds of the general formula (I) according to the invention have very good insecticidal and parasiticidal properties and can be used in crop protection, veterinary hygiene and material protection for controlling undesired pests, such as insects, endo- or ectoparasites.
  • the invention also relates to all stereoisomers which are encompassed by formula (I) and mixtures thereof.
  • stereoisomers such as enantiomers, diastereomers, Z and E isomers are all of the formula (I) and can be obtained by conventional methods from mixtures of stereoisomers or by stereoselective reactions in combination with the use of stereochemically pure starting materials are produced.
  • Compounds of the general formula (I) optionally consist of a mixture of the respective enantiomers which are chiral on the sulfur function,
  • Racemic mixtures for example of optically active sulfoxides of the general formula (I), can be separated by known processes. Such racemate resolution methods are in
  • Eligible e.g. Adduct formation with an optically active auxiliary reagent, separation of the diastereomeric adducts into the corresponding diastereomers, e.g. by crystallization, chromatography, especially column chromatography and
  • optically active acid is e.g. Camphorsulfonic acid, camphoric acid, bromocamphorsulfonic acid, quinic acid, tartaric acid, dibenzoyltartaric acid and other analogous acids
  • optically active bases are e.g. Quinine, cinchonine, quinidine, brucine, 1-phenylethylamine and other analogous bases in question.
  • the crystallizations are then usually carried out in aqueous or aqueous-organic solvents, wherein the diastereomer with the lower solubility, if appropriate after inoculation, first fails.
  • the one enantiomer of the compound of formula (I) is then released from the precipitated salt or the other from the crystals by acidification or with base.
  • racemates can be separated chromatographically with chiral stationary phases. Enantiomer separations of this type can be carried out from mg to the 100 kg range with preparative HPLC systems in single or continuous operation.
  • the compounds of the invention are generally defined by the formula (I).
  • Preferred, particularly preferred and very particularly preferred radical definitions of the above and below-mentioned formulas are given below. These definitions apply equally to the end products of general formula (I) as well as to all intermediates.
  • a 1 is preferably nitrogen and A 2 is preferably CH or CR 3 .
  • a 1 is preferably CH or CR 3 and A 2 is CH or CR 3 , where in the case of several radicals R 3, the radicals R 3 may each be identical or different.
  • a 1 is preferably C-R 3 and A 2 is preferably nitrogen.
  • the invention further relates in a fourth embodiment to compounds of the formula (I) or to compounds according to one of the first to third embodiments in which the radical B is
  • C, -C 6 alkyl Haio-C 1 -C 6 alkyl, C r C 6 alkoxy-C 6 alkyl, Ci-C6 - alkoxycarbonyl-C, -C 6 alkyl , C 2 -C 6 alkenyl; C 2 -C 6 alkynyl, tri (C 1 -C 4 alkyl) silyl C 1 -C 6 alkyl; Phenyl-Ci-C ö alkyl which on the aromatic ring may optionally be singly or multiply substituted identically or differently by fluorine, chlorine, bromine, iodine, methyl, trifluoromethyl or methodological xy; and 2-pyridyl-C, -C 6 -alkyl;
  • the invention relates to compounds of the formula (I) or to compounds according to one of the first to fourth embodiments in which the radicals R 1 and R 2 are each independently of one another
  • halogen particularly preferably represents halogen, C) -C 6 -alkyl, C r C 6 -haloalkyl, QC 6 -alkoxy and C 1 -C 6 -haloalkoxy;
  • Ci-C 6 alkyl very particularly preferably represents halogen, Ci-C 6 alkyl, C 1 -C 6 -HaIOaIlCyI and C 1 -C 6 -alkoxy group;
  • the invention in a seventh embodiment relates to compounds of the formula (I) or to compounds according to one of the first to sixth embodiments in which the radical X is preferably phenyl, 2-pyridyl or 3-pyridyl, which in each case may optionally be mono- or polysubstituted by identical or different substituents, by one or more substituents selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy , COOH, nitro, amino, alkylamino, dialkylamino, wherein vicinal alkyl, haloalkyl, alkoxy and / or haloalkoxy groups together with the carbon atoms to which they are attached can form a five- to six-membered cyclic system containing from 0 to 2 oxygen atoms contains, and whose alkyl moiety may optionally be substituted by one or more fluorine atoms, is;
  • phenyl which may optionally be mono- or polysubstituted or differently substituted by one or more substituents selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, COOH, nitro, amino, alkylamino , Dialkylamino, wherein vicinal alkyl, haloalkyl, alkoxy and / or haloalkoxy together with the carbon atoms to which they are attached, can form a five- to six-membered cyclic system containing 0 to 2 oxygen atoms, and its alkyl moiety optionally with a or more than one fluorine atom may be substituted;
  • phenyl which is monosubstituted or polysubstituted by at least one substituent selected from the group consisting of halogen, C 1 -C 6 haloalkyl and C 1 -C 6 alkoxy, vicinal alkyl, haloalkyl, alkoxy and or haloalkoxy groups together with the carbon atoms to which they are attached can form a five- to six-membered cyclic system which contains 0 to 2 oxygen atoms and whose alkyl moiety may optionally be substituted by one or more fluorine atoms;
  • the invention relates to compounds of the formula (I) or to compounds according to one of the first to eighth embodiments of the radical n
  • the radical B is alkyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, haloalkyl, alkoxyalkyl, cyanoalkyl, alkylthioalkyl Alkylsulfinylalkyl, alkylsulfonylalkyl, aminoalkyl, alkylcarbonylalkyl, alkoxycarbonylalkyl, alkenyl and alkynyl, each of which may optionally be mono- or polysubstituted by identical or different substituents by halogen, alkyl, haloalkyl, alkoxy, nitro or cyano; Phenalkyl which may optionally be monosubstituted or polysubstituted by identical or different substituents on the aromatic group by halogen, alkyl, haloal
  • radical B This excludes from the definition of the compounds of the general formula (I) in particular the compounds which, as radical B, have a carbonylalkylamino radical and an alkylamino radical.
  • radical B Preferred, particularly preferred, very particularly preferred and special meanings for the radical B correspond to the above definitions.
  • the meanings of the remaining radicals or substituents of the general formula (I) can correspond to the general, preferred, particularly preferred, very particularly preferred and special meanings.
  • substituents may be halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenoxy, alkynoxy, cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, alkylsulfanyl, haloalkyl sulfanyl, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, carboxamide, dialkylcarboxamide, trialkylsilyl, nitro, amino
  • halogens in particular fluorine, chlorine, bromine or iodine
  • Haloalkyl such as CF 3
  • Alkoxy such as OCH 3
  • compounds in which vicinal alkyl, haloalkyl, alkoxy and / or haloalkoxy groups together with the carbon atoms to which they are attached form a five- to six-membered cyclic system containing from 0 to 2 oxygen atoms and its alkyl moiety, if appropriate may be substituted with one or more fluorine atoms.
  • the meanings of the other radicals or substituents of the general formula (I) may correspond to the general, preferred, particularly preferred, very particularly preferred and special meanings.
  • compounds of the general formula (I), in particular compounds according to the abovementioned embodiments, in which the radical A 1 is CR 3 and the radical A 2 is N is included.
  • the meanings of the remaining radicals or substituents of the general formula (I) may correspond to the general, preferred, particularly preferred, very particularly preferred and special meanings.
  • Preferred, particularly preferred, very particularly preferred and especially are compounds which in each case carry the substituents mentioned under preferred, particularly preferred, very particularly preferred and particularly preferred.
  • halogen means fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • Halogen substituted radicals e.g. Haloalkyl
  • Halogen substituted radicals are halogenated once or several times up to the maximum possible number of substituents.
  • the halogen atoms may be the same or different.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl, alkenyl or alkynyl may also be used in conjunction with heteroatoms, e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • Alkyl means a straight-chain or branched open-chain hydrocarbon radical.
  • alkyl (Ci-Ci 2) -alkyl, particularly preferably (Ci-Cg) -alkyl, in particular (Ci-Ce) -alkyl, in particular (C r C 4) alkyl, comprising.
  • alkyl radicals in assembled radicals, for example, alkoxy, haloalkyl, and are, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, Hexyl and 1,3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1,4-dimethylpentyl.
  • monohaloalkyl such as CH 2 CH 2 Cl, CH 2 CH 2 F, CHClCH 3 , CHFCH 3 , CH 2 Cl, CH 2 F
  • Perhaloalkyl such as CC
  • Alkenyl furthermore denotes a straight-chain or branched open-chain hydrocarbon radical having at least one double bond.
  • alkenyl (C 2 -Ci 2 ) -
  • Alkenyl particularly preferably (C 2 -C 8 ) -alkenyl, in particular (C 2 -C 6 ) -alkenyl, especially (C 2 -C 4 ) -
  • Alkenyl includes.
  • suitable alkenyl radicals are 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulated double bonds, such as, for example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2 , 3-Pentatrienyl.
  • radical alkenyl are vinyl, which may optionally be substituted by further alkyl radicals, for example prop-1-en-1-yl, but-1-en-1-yl; Allyl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, 1-methyl-but-3-ene 1-yl and 1-methylbut-2-en-1-yl, 2-methylprop-1-en-1-yl, 1-methylprop-1-en-1-yl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, butyric 3-en-1-yl, 1-methylbut-3-en-1-yl or 1-methylbut-2-en-1-yl, pentenyl, 2-methylpentenyl and hexenyl.
  • alkyl radicals for example prop-1-en-1-yl, but-1-en-1-yl; Allyl, 1-methyl-prop-2-en-1-yl, 2-methyl-
  • Alkynyl furthermore denotes a straight-chain or branched open-chain hydrocarbon radical having at least one triple bond. Optionally, one or more double bonds may be present.
  • Corresponding examples are ethynyl, propargyl, 1-methylprop-2-yn-1-yl, 2-butynyl, 2-pentynyl, 1,3-butatrienyl or 3-penten-1-yn-1-yl or 2-yl Hexynyl, preferably propargyl, but-2-yn-1-yl, but-3-yn-1-yl or 1-methyl-but-3-yn-1-yl.
  • Alkylidene e.g. B. in the form (Ci-C 10 ) alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • Cycloalkyl means a carbocyclic saturated ring system preferably having 3 to 8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • substituents wherein substituents having a double bond on the cycloalkyl, z.
  • alkylidene group such as methyl iden, are included.
  • polycyclic aliphatic systems are also included, such as, for example, bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentane-1 -yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2. l] hept-2-yl (norbornyl), adamantan-1-yl and adamantan-2-yl.
  • spirocyclic aliphatic systems are also included, for example spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [ 2.3] hex-5-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system having preferably 4 to 8 C atoms, for example 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl, z.
  • an alkylidene group such as methylidene, are included.
  • Aryl is a mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • aryl In the case of substituted or unsubstituted aryl, there are also more cyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the binding site is on the aromatic system.
  • aryl is also encompassed by the term "optionally substituted phenyl”.
  • heterocyclyl or heterocyclic ring When the heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • heterocyclyl In the case of optionally substituted heterocyclyl, more cyclic systems are also included, such as, for example, 8-azabicyclo [3.2.1] octanyl or 1-azabicyclo [2.2.1] heptyl.
  • spirocyclic systems are also included, such as, for example, 1-oxa-5-azaspiro [2.3] hexyl.
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group consisting of N , O, and S, but not two oxygen atoms should be directly adjacent.
  • heteroaryl is understood to mean systems as defined above under “heterocyclyl” but which are heteroaromatic, ie. H. represent a fully unsaturated aromatic heterocyclic compound.
  • substituted by one or more radicals means, independently of one another, one or more identical or different radicals, it being possible for two or more radicals to form one or more rings on one cycle as main body.
  • Substituted radicals such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, are, for example, a substituted radical derived from the unsubstituted radical, where the substituents for example one or more, preferably 1, 2 or 3, radicals from the group consisting of halogen, alkoxy, alkylthio, hydroxyl, amino, nitro, carboxy or a group equivalent to the carboxy group, cyano, isocyanato, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, Mono- and dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and dialkylamino, trialkylsilyl and optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heterocycly
  • substituents in addition to the said saturated hydrocarbon-containing radicals corresponding unsaturated aliphatic and aromatic radicals such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenyloxycarbonyl, alkynyloxycarbonyl , Alkenylcarbonyl, alkynylcarbonyl, mono- and dialkenylaminocarbonyl, mono- and dialkynylaminocarbonyl, mono- and dialkenylamino, mono- and dialkynylamino, trialkenylsilyl, trialkynylsilyl, optionally substituted cycloalkenyl, optionally substituted cycloalkynyl, phenyl, phenoxy, etc., included.
  • substituted cyclic radicals having a-liphatischen portions in the ring and cyclic systems are also having such substituents which are bonded to a double bond on the ring, z. B. with an alkylidene group such as methyl iden or ethylidene or an oxo group, imino group or substituted imino group are substituted.
  • radicals form one or more rings
  • these may be carbocyclic, heterocyclic, saturated, partially saturated, unsaturated, for example also aromatic and, where appropriate, further substituted.
  • the annelated rings are preferably 5- or 6-membered rings, particularly preferred are benzo-fused rings.
  • first substituent level may, if they contain carbon-containing moieties, optionally further substituted there (“second substituent level”), for example by one of the substituents as defined for the first substituent , Corresponding further substituent levels are possible.
  • substituted radical includes only one or two substituent levels.
  • Preferred substituents for the substituent levels are, for example, amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, carboxy, carbonamide, SF 5 , aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, monoalkylamino, dialkyl amino, N- Alkanoylamino, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio, cycloalkylthio, alkenylthio, cycloalkene nylthio, al
  • the compounds of the general formula (I) can be obtained, if appropriate, by addition of a suitable inorganic or organic acid, for example mineral acids, in particular HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or, for example, organic acids, in particular carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or, for example, sulfonic acids, in particular p-toluenesulfonic acid, to a basic group, such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • a suitable inorganic or organic acid for example mineral acids, in particular HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • organic acids in particular carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or
  • Suitable substituents which are in deprotonated form e.g. Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups.
  • the present compounds of the general formula (I) can be prepared by the following processes, the compounds of the general formula (I)
  • ⁇ BB aryl, hetaryl
  • a 1 , A 2 , B, X, R 3 and n have the meanings given above and LG stands for any leaving group.
  • the present invention therefore also relates to a process for the preparation of the compounds of general formula (I) by the following reaction
  • R 1 and R 2 are hydrogen, R 3 , X, Y, B and n are as defined above.
  • the educt used for this reaction is recovered according to the reaction scheme shown above.
  • the leaving group LG is not particularly limited and may be, for example, a halogen, an alkylsulfonyl, an alkylsulfinyl, an alkylsulfanyl or nitro.
  • ketene S, S-dithioacetals of the general formula (IV), (IV-A) or (IV-B) are first reacted with hydrazine hydrate in a suitable solvent.
  • the resulting aminopyrazoles of general formula (V) are then reacted with azinyl derivatives of general formula (VI) containing a suitable leaving group "LG" such as halogens, alkylsulfonates, arylsulfonates, alkylsulfonyls, alkylsulfinyls, alkylsulfanyls or nitro.
  • LG suitable leaving group
  • a further subject of the present invention are the intermediates of the general formula (IV) in this synthesis.
  • G 1 , G 2 and G 3 are selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenoxy, alkynoxy, cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, Alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, carboxamide, dialkylcarboxamide, trialkylsilyl, nitro, amino, alkylamino, dialkylamino, alkylsulfonylamino, dialkylsulf
  • G 1 , G 2 and G 3 are each independently selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, COOH nitro, amino, alkylamino, dialkylamino, vicinal alkyl, Haloalkyl, alkoxy and / or Haloalko- xy phenomenon together with the carbon atoms to which they are attached, can form a five- to six-membered cyclic system containing 0 to 2 oxygen atoms, and the alkyl moiety may be optionally substituted with one or more fluorine atoms ,
  • G 1, G 2 and G 3 are each independently selected from the group consisting of halogen, Ci.C ö -haloalkyl and Ci-C 6 -alkoxy, where vicinal alkyl, haloalkyl, alkoxy and / or haloalkoxy groups together with the carbon atoms to which they are attached can form a five- to six-membered cyclic system which contains 0 to 2 oxygen atoms, and whose alkyl moiety may optionally be substituted by one or more fluorine atoms.
  • G 1 , G 2 and G 3 each independently of one another, selected from the group consisting of fluorine, chlorine, bromine, iodine, CF 3 , CH 3 O, OCH 2 O, OCH 2 CH 2 and OCF 2 O.
  • X has one of the following meanings:
  • the present invention furthermore relates to the intermediates of the general formula (IV-A) in this synthesis.
  • G 1 , G 2 and G 3 are selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenoxy, alkynoxy, cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, Alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, carboxamide, dialkylcarboxamide, trialkylsilyl, nitro, amino, alkylamino, dialkylamino, alkylsulfonylamino, dialkylsulf
  • G 1 , G 2 and G 3 are each independently selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, COOH nitro, amino, alkylamino, dialkylamino, vicinal alkyl, Haloalkyl, alkoxy and / or Haloalko- xy phenomenon together with the carbon atoms to which they are attached, can form a five- to six-membered cyclic system containing 0 to 2 oxygen atoms, and the alkyl moiety may be optionally substituted with one or more fluorine atoms ,
  • G 1 , G 2 and G 3 each independently of one another, selected from the group consisting of halogen, C 1 -C 6 -haloalkyl and C 1 -C 6 -alkoxy, where vicinal alkyl, haloalkyl, alkoxy and / or haloalkoxy groups together with the carbon atoms to which they are attached can form a five- to six-membered cyclic system containing 0 to 2 oxygen atoms, and whose alkyl moiety may be optionally substituted with one or more fluorine atoms.
  • G 1 , G 2 and G 3 each independently of one another, selected from the group consisting of fluorine, chlorine, bromine, iodine, CF 3 , CH 3 O, OCH 2 O, OCH 2 CH 2 and OCF 2 O.
  • X has one of the following meanings:
  • G 1 , G 2 and G 3 are selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenoxy, alkynoxy, cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, Alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, carboxamide, dialkylcarboxamide, trialkylsilyl, nitro, amino, alkylamino, dialkylamino, alkylsulfonylamino, dialkylsulf
  • G 1 , G 2 and G 3 are each independently selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, COOH, nitro, amino, alkylamino, dialkylamino, vicinal alkyl , Haloalkyl, alkoxy and / or Haloalko- xy phenomenon together with the carbon atoms to which they are attached, can form a five- to six-membered cyclic system containing 0 to 2 oxygen atoms, and its alkyl moiety optionally substituted with one or more fluorine atoms can.
  • G 1 , G 2 and G 3 each independently, selected from the group consisting of halogen, Ci.C ⁇ -haloalkyl and Ci-C 6 alkoxy, wherein vicinal alkyl, haloalkyl, alkoxy and / or Haloalkoxy groups together with the carbon atoms to which they are attached can form a five- to six-membered cyclic system containing 0 to 2 oxygen atoms. contains atoms, and whose alkyl moiety may optionally be substituted with one or more fluorine atoms.
  • G 1 , G 2 and G 3 each independently of one another, selected from the group consisting of fluorine, chlorine, bromine, iodine, CF 3 , CH 3 O, OCH 2 O, OCH 2 CH 2 and OCF 2 O.
  • X has one of the following meanings:
  • R, R, A, A, B, X, R and n have the meanings given above.
  • corresponding thioethers of the general formula (IA) are reacted with one mole of a suitable oxidizing agent, for example with H 2 O 2 , sodium periodate, tert-butyl hypochlorite, calcium hypochlorite Ca (OCl) 2 , sodium chlorite NaClO 2 , sodium hypochlorite NaOCl, peracids or O 2 and catalytic cerium ammonium nitrate.
  • a suitable oxidizing agent for example with H 2 O 2 , sodium periodate, tert-butyl hypochlorite, calcium hypochlorite Ca (OCl) 2 , sodium chlorite NaClO 2 , sodium hypochlorite NaOCl, peracids or O 2 and catalytic cerium ammonium nitrate.
  • a suitable oxidizing agent for example with H 2 O 2 , sodium periodate, tert-butyl hypochlorite, calcium hypochlorite Ca (OCl) 2 ,
  • a 1 , A 2 , B, X, R 3 , R 6 and n have the meanings given above.
  • A, A, B, X, Y, R, R, R and n have the meanings given above.
  • the free NH 2 group of the compounds (IA) - (IF) is prepared by the generally known processes for basic alkylation or acylation with the corresponding alkylation. or acylating reagents (XI) and (Xu) reacted.
  • A, A, B, X, Y, R, R, R and n have the meanings given above.
  • the present invention therefore also relates to a process for the preparation of the compounds of general formula (I) by the following reaction:
  • A, A, B, X, Y, R, R, R and n have the meanings given above.
  • a 1 , A 2 , B, X, R 3 and n have the meanings given above and LG stands for any leaving group.
  • G 1 , G 2 and G 3 are selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl, alkenoxy, alkynoxy, cycloalkylalkoxy, haloalkoxy, haloalkoxyalkyl, alkylsulfanyl, haloalkylsulfanyl, Alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, alkylcarbonyl, alkoxycarbonyl, alkoxycarbonylalkyl, carboxyl, carboxamide, dialkylcarboxamide, trialkylsilyl, nitro, amino, alkylamino, dialkylamino, alkylsulfonylamino, dialkylsulf
  • G 1 , G 2 and G 3 are each independently selected from the group consisting of halogen, alkyl, haloalkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, COOH, nitro, amino, alkylamino, dialkylamino, vicinal alkyl , Haloalkyl, alkoxy and / or Haloalko- xy phenomenon together with the carbon atoms to which they are attached, can form a five- to six-membered cyclic system containing 0 to 2 oxygen atoms, and its alkyl moiety optionally with one or more fluorine atoms may be substituted.
  • G 1 , G 2 and G 3 each independently, selected from the group consisting of halogen, Ci.C 6 -haloalkyl and C 1 -C 6 -Akoxy, where vicinal alkyl, haloalkyl, alkoxy and or haloalkoxy groups together with the carbon atoms to which they are attached can form a five- to six-membered cyclic system which contains 0 to 2 oxygen atoms, and whose alkyl moiety may optionally be substituted by one or more fluorine atoms.
  • G 1 , G 2 and G 3 each independently of one another, selected from the group consisting of fluorine, chlorine, bromine, iodine, CF 3 , CH 3 O, OCH 2 O, OCH 2 CH 2 and OCF 2 O.
  • X has one of the following meanings:
  • the active compounds according to the invention are suitable for plant tolerance, favorable warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs which are found in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Anoplura e.g. Damalinia spp., Haematopinus spp., Ligognathus spp., Pediculus spp., Trichodectes spp.
  • arachnids e.g. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp.
  • Eriophyes spp. Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphago- tarsonemus latus, Psoroptes spp., Rhipicephalus spp , Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
  • Naupactus xanthographus Naptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleareae, Phyllophaga spp., Popillia japonica, Premnotrypes spp.
  • Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
  • helminths e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nemat
  • protozoa such as Eimeria
  • Eimeria protozoa
  • Doralis spp. Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp ., Laodelph ax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Lepidoptera From the order of Lepidoptera, for example Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Caceacia podana, Capua reticulana, Carpocapsa pomonella, Cheimatobia brumata, Chilo spp.
  • Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
  • siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanoptera e.g. Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Thysanura e.g. Lepisma saccharina.
  • the plant parasitic nematodes include e.g. Anguina spp., Aphelenchoides spp., Belonoclampus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotary Lenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipetnetrans, Xiphinema spp.
  • Anguina spp. Aphelenchoides spp., Belonoclampus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera
  • the compounds according to the invention may also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including agents against viroids) or as Agents against MLO (mycoplasma-like-organism) and RLO (Rickettsia-like-organism) can be used. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, active ingredient impregnated synthetic materials, fertilizers and micro-encapsulants in polymeric materials.
  • These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. The preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquor, seed dressing), such as certain technical properties and / or specific biological properties.
  • Typical auxiliaries are: extenders, solvents and carriers.
  • polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), Esters (including fats and oils) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, and water.
  • Suitable solid carriers are:
  • ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules in question: eg broken and fractionated natural rocks such Calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks;
  • suitable emulsifiers and / or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol Ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable
  • oligo- or polymers for example starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with, for example, (poly) alcohols or (poly) amines. It is also possible to use liginine and its sulfonic acid derivatives, simple and modified celluloses, aromatic and / or aliphatic sulfonic acids and also adducts thereof with formaldehyde.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-type polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • 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.
  • 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.
  • additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents which improve the chemical and / or physical stability, may furthermore be present.
  • the formulations generally contain between 0.01 and 98% by weight of active ingredient, preferably between 0.5 and 90%.
  • the active ingredient according to the invention can be present in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
  • Particularly favorable mixing partners are, for example, the following: fungicides:
  • inhibitors of nucleic acid synthesis such as benalaxyl, benalaxyl-M, bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M, ofurace, oxadixyl and oxolic acid.
  • Mitosis and cell division inhibitors such as benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fuberidazole, pencycuron, thiabendazole, thiophanate, thiophanate-methyl and zoxamide.
  • inhibitors of respiration such as diflumetorim as an inhibitor at complex I of the respiratory chain; Bixafen, boscalid, carboxin, fenfuram, flutolanil, fluopyram, furametpyr, furmecyclox, isopyrazam (mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-epimeric racemate 1RS, 4SR, 9SR), isopyrazam (syn epimeric racemate 1RS, 4SR, 9RS), isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), isopyrazam (syn-epimeric enantiomer 1S, 4R, 9S), isopyrazam (anti-epimeric racemate 1RS, 4SR, 9SR), isopyrazam (anti-epimeric racemate 1RS, 4SR, 9SR), isopyrazam (anti-epimeric racemate 1RS, 4SR,
  • decouplers such as binapacryl, dinocap, fluazinam and meptyldinocap.
  • inhibitors of ATP production such as, for example, fentin acetate, fentin chloride, fentin hydroxide and silthiofam.
  • inhibitors of amino acid and protein biosynthesis such as andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim and pyrimethanil.
  • signal transduction inhibitors such as fenpiclonil, fludioxonil and quinoxyfen.
  • Inhibitors of lipid and membrane synthesis such as biphenyl, chlozolinate, edifenphos, etridiazole, iodocarb, Iprobenfos, iprodione, isoprothiolane, procymidone, propamocarb, propamocarb hydrochloride, pyrazophos, tolclofos-methyl and vinclozolin.
  • inhibitors of ergosterol biosynthesis such as aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, Dodemorph, Dodemo ⁇ h Acetate, Epoxiconazole, Etaconazole, Fenarimol, Fenbuconazole, Fenhexamid, Fenpropidin, Fenpropimo ⁇ h, Fluquinconazole, Flurprimidol, Flusilazole, Flutriafol, Furconazole, Furconazole Cis, Hexaconazole, Imazalil, Imazalil Sulfate, Imibenconazole, Ipconazole, Metconazole, Myclobutanil, Naftifine, Nuarimol, Oxpoconazole, Paclobutrazol, Pefurazoate, Penconazole, Pipera
  • inhibitors of cell wall synthesis such as Benthiavalicarb, Dimethomo ⁇ h, Flumo ⁇ h, Iprovalicarb, Mandipropamid, Polyoxins, Polyoxorim, Prothiocarb, Validamycin A and valefenalate.
  • inhibitors of melanin biosynthesis such as, for example, caryropamide, diclocymet, fenoxanil, fthalide, pyroquilone and tricyclazole.
  • resistance inducers such as acibenzolar-S-methyl, probenazole and tiadinil.
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamates, Trimethacarb, XMC and xylylcarb; or
  • AChE Acetylcholinesterase
  • Organophosphates eg acephates, azamethiphos, azinphos (-methyl, -ethyl), cadusafos, chiorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl), coumaphos, cyanophos, demeton-s-methyl, diazinon, dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulphon, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Isofenphos, Isopropyl O- (methoxyaminothio-phosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Ometho
  • GABA-regulated chloride channel antagonists such as organochlorines, eg, chlordane and endosulfan (alpha); or fiproles (phenylpyrazoles), for example ethiprole, fipronil, pyrroliprole and pyriprole.
  • sodium channel modulators / voltage-dependent sodium channel blockers such as, for example, pyrethroids, eg acrinathrin, allethrin (d-cis-trans, d-trans), bifenthrin, bioallethrin, bioalbhrine-S-cyclopentenyl, Bioresmethrin, cycloprothrin, cyfluthrin (beta), cyhalothrin (gamma, lambda), cypermethrin (alpha, beta, theta, zeta), cyphenothrin [(IR) trans-lsome], deltamethrin, dimefluthrin , Empenthrin [(5 1 Z) - (IA) -IsOmCrC], esfenvalerates, etofenprox, fenpropathrin, fenvalerates, flucythrinates, flumethrin,
  • nicotinergic acetylcholine receptor agonists such as neonicotinoids, e.g. Acetamidipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; or nicotine.
  • Allosteric acetylcholine receptor modulators such as spinosyns, e.g. Spinetoram and spinosad.
  • chloride channel activators such as avermectins / milbemycins, e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone analogs e.g. Hydroprene, kinoprene, methoprene; or fenoxycarb; Pyritexyfen.
  • agents with unknown or non-specific mechanisms of action such as
  • Fumigant e.g. Methyl bromide and other alkyl halides; or chloropicrin; Sulfuryl fluoride; Borax; Tartar emetic.
  • mite growth inhibitors e.g. Clofentezine, diflovidazine, hexythiazox, etoxazole.
  • Microbial disruptors of insect intestinal membrane such as Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, and BT plant proteins, eg Cryl Ab, Cry 1 Ac, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Abl.
  • insect intestinal membrane such as Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, and BT plant proteins, eg Cryl Ab, Cry
  • inhibitors of oxidative phosphorylation, ATP disruptors such as diafenthiourone; or organotin compounds, eg azocyclotine, cyhexatin, fenbutatin oxide; or propriety; Tetradifon.
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap (hydrochloride), thiocylam, and thiosultap (sodium).
  • inhibitors of chitin biosynthesis type 0, such as benzoylureas, e.g. Bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • benzoylureas e.g. Bistrifluron, chlorofluorazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Moulting agents such as Cyromazine.
  • Diacylhydrazines e.g. Chromafenozide, Halofenozide, Methoxyfenozide and Tebufenozide.
  • Octopaminergic agonists such as amitraz.
  • side-III electron transport inhibitors / side II electron transport inhibitors such as, for example, hydramethylnone; acequinocyl; fluacrypyrim; or Cyflumetofen and Cyenopyrafen.
  • Electron transport inhibitors such as side-I electron transport inhibitors, from the group of METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebfenpyrad, Tolfenpyrad; or Rotenone (Denis).
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebfenpyrad, Tolfenpyrad; or Rotenone (Denis).
  • (23) inhibitors of acetyl-CoA carboxylase such as tetronic acid derivatives, e.g. Spidrodiclofen and spiromesifen; or tetramic acid derivatives, e.g. Spirotetramat.
  • side FV electron transport inhibitors such as phosphenes, e.g. Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide; or cyanide.
  • Ryanodine receptor effectors such as diamides, eg chlorantraniliprole (rynaxypyr), cyantraniliprole (cyazypyr) and flubendiamide.
  • Other drugs with unknown mechanism of action such as Azadirachtin, Amidofiumet, Benzoximate, Bifenazate, Chinomethionat, Cryolite, Dicofol, Flufenerim, Pyridalyl and Pyrifluquinazone; or the following known effective compounds
  • the active compounds according to the invention can furthermore be present when used as insecticides in their commercial formulations as well as in the formulations prepared from these formulations in admixture with synergists.
  • Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
  • the active compounds according to the invention may furthermore, when used as insecticides in their commercial formulations and in the forms of use prepared from these formulations, be present in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
  • the application is done in a custom forms adapted to the application.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including plant varieties that are protectable or unprotectable by plant variety rights.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • Treatment methods eg by dipping, spraying, evaporating, misting, spreading, spreading painting, injecting and propagating material, in particular seed, by single or multi-layer coating.
  • plants and their parts can be treated.
  • wild species or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant varieties and their parts are treated.
  • transgenic plants and plant cultivars obtained by genetic engineering if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • the terms "parts” or “parts of plants” or “plant parts” have been explained above.
  • Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
  • the treatment according to the invention may also result in superadditive (“synergistic”) effects.
  • superadditive for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents usable in the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering power , facilitated harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of the harvested products, which go beyond the actual expected effects.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased defense of the plant against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as increased tolerance of the plants to certain herbicidal active substances.
  • transgenic plants are the important crops, such as cereals (wheat, rice), maize, soya, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, rapeseed, and fruit plants (with the fruits apples, pears, Citrus fruits and grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape.
  • Traits which are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins which are formed in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (cf.
  • Bt plants are produced in the plants (hereinafter "Bt plants”. Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
  • SAR systemic acquired resistance
  • PAT phosphinotricin
  • genes which confer the desired properties can also occur in combinations with one another in the transgenic plants.
  • “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, eg rapeseed
  • IMI® tolerance against imidazolinone
  • STS® tolerance to sulfonylureas eg corn
  • Clearfield® varieties eg corn
  • the listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active substance mixtures according to the invention.
  • the preferred ranges given above for the active compounds or mixtures also apply to the Treatment of these plants. Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
  • the compounds of the present invention can be used to control a variety of pests including, for example, noxious sucking insects, biting insects and other plant parasitic pests, storage pests, pests that destroy industrial materials and use and control pests including parasites in the animal health field for example their extinction and eradication.
  • the present invention thus also includes a method of controlling pests.
  • the active substances according to the present invention act against animal parasites, in particular ectoparasites or endoparasites.
  • the term endoparasites includes in particular helminths such as cestodes, nematodes or trematodes, and protozoa such as kozzidia.
  • Ectoparasites are typically and preferably arthropods, especially insects such as flies (stinging and licking), parasitic fly larvae, lice, hair-pieces, feathers, fleas and the like; or acarids such as ticks, for example ticks or leather ticks, or mites such as mange mites, mites, feather mites and the like.
  • These parasites include:
  • Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phytus spp., Solenopotes spp .; specific examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotes capillatus;
  • Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; specific examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi;
  • Nematocerina and Brachycerina eg Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp , Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp.
  • rophilus spp. Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp .; specific examples are: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia omata
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsyl Ia spp., Ceratophyllus spp .; specific examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis;
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • Omithonyssus spp. the original genus of the multiple ticks
  • Omithonyssus spp. Pneumonyssus spp.
  • Raillietia spp. Pneumonyssus spp.
  • Sternostoma spp. Varroa spp.
  • Acarapis spp . specific examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophillus annulatus), Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypti cumulus, Hyalomma marginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricin
  • 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., Hypodectes spp., Pteroli- spp.
  • the active compounds according to the invention are also suitable for controlling arthropods, helminths and protozoa which infest animals.
  • the animals include farm animals such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees.
  • farm animals such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees.
  • the animals also include domestic animals - also referred to as pets - such as pets. Dogs, cats, caged birds, aquarium fish and so-called experimental animals such. Hamsters, guinea pigs, rats and mice.
  • control of the parasites can also help to prevent the transmission of infectious substances.
  • control means that the active substances act by controlling the occurrence of the parasite reduce the animal infected with such parasites to harmless levels. More specifically, as used herein, “control” means that the agent kills the subject parasite, inhibits its growth, or inhibits its proliferation.
  • the active compounds according to the invention when used for the treatment of animals, can be used directly.
  • they are used as pharmaceutical compositions which may contain pharmaceutically acceptable excipients and / or adjuvants known in the art.
  • the active ingredients may be shampoo or suitable, in aerosols or pressureless sprays , eg Pump sprays and atomizer sprays, applicable, formulated formulations.
  • the active compounds according to the invention can be used as formulations (for example powders, wettable powders, WPs), emulsions, emulsifiable concentrates (EC), flowable agents, homogeneous Solutions and suspension concentrates [suspension concentrates, "SC"]) containing the active ingredients in an amount of 1 to 80 wt .-%, directly or after dilution (eg 100- to 10,000facher dilution) apply or use them as a chemical bath.
  • formulations for example powders, wettable powders, WPs), emulsions, emulsifiable concentrates (EC), flowable agents, homogeneous Solutions and suspension concentrates [suspension concentrates, "SC”]
  • the active compounds according to the invention can be used in combination with suitable synergists or other active substances such as, for example, acaricides, insecticides, anthelmintics, antiprotozoal agents.
  • the compounds according to the invention show a high insecticidal activity against insects which destroy industrial materials.
  • insects By way of example and preferably without limiting however, the following insects are mentioned:
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zooter- mopsis nevadensis, Coptotermes formosanus;
  • Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
  • the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water.
  • the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • the active compounds are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, which are used in closed rooms, such as apartments, factory buildings, offices, vehicle cabins u.a. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Scorpionidea eg Buthus occitanus.
  • Acarina for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus galinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in scattered edema or bait stations.
  • Pump and atomizer sprays misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in scattered edema or bait stations.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperd®).
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Bean leaf discs Phaseolus vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Chinese cabbage leaf discs (Brassica pekinensis), which are infested by all stages of the green pepper aphid (Myzus persicae), are sprayed with an active compound preparation of the desired concentration.
  • Vessels are filled with sand, drug solution, Meloidogyne j / icogM / ta-egg larvae suspension and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal activity is determined by means of bile formation in%. 100% means that no bile was found; 0% means that the number of bile on the treated plants corresponds to that of the untreated control.
  • Boophilus microplus test (BOOPMI injection)
  • active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
  • the drug solution is injected into the abdomen (Boophilus microplus), the animals are transferred into trays and stored in an air-conditioned room. The effect control takes place on storage of fertile eggs.
  • active compound For the preparation of a suitable preparation of active compound, 2 parts by weight of active compound are mixed with the stated amount of solvent. Part of the concentrate is diluted with citrated bovine blood and the desired concentration is produced.
  • fasting adult fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom.
  • a metal cylinder is placed on the chamber, the underside of which is sealed with parafilm.
  • the cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane.
  • Vessels containing horsemeat treated with the preparation of active compound of the desired concentration are infested with Lucilia cuprina larvae.
  • Vessels containing a sponge treated with the preparation of active compound of the desired concentration are mated with Musca domestica adults.

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

Abstract

La présente invention concerne des dérivés sulfurés de 1-azinyl-pyrazole, leur utilisation en tant qu'insecticides et/ou parasiticides, et un procédé pour les préparer. L'invention concerne également différents produits intermédiaires qui interviennent dans la préparation des dérivés sulfurés de 1-azinyl-pyrazole de l'invention. L'invention a finalement pour objet des agents contenant de tels azinyl-pyrazoles.
PCT/EP2009/004391 2008-06-26 2009-06-18 Dérivés sulfurés de 1-azinyl-pyrazole utilisés en tant qu'insecticides Ceased WO2009156090A2 (fr)

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EP08159069 2008-06-26

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AR (1) AR072673A1 (fr)
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120190687A1 (en) * 2009-05-29 2012-07-26 Bayer Cropscience Ag Pyrazinylpyrazoles
WO2013164295A1 (fr) 2012-05-04 2013-11-07 Basf Se Composés contenant du pyrazole substitué et leur utilisation comme pesticides
US9556141B2 (en) 2011-11-21 2017-01-31 Basf Se Process for preparing N-substituted 1H-pyrazole-5-carboxylate compounds and derivatives thereof
WO2021151976A1 (fr) * 2020-01-31 2021-08-05 Bayer Aktiengesellschaft Dérivés de l'acide [(1,4,5-trisubstitué-1h-pyrazol-3-yl)sulfanyl]acétique, leurs sels et leur utilisation comme ingrédients herbicides
WO2024121263A1 (fr) 2022-12-09 2024-06-13 Syngenta Crop Protection Ag Composé insecticide à base de dérivés de pyrazole
WO2024121264A1 (fr) 2022-12-09 2024-06-13 Syngenta Crop Protection Ag Composé insecticide à base de dérivés de pyrazole
WO2024121261A1 (fr) 2022-12-09 2024-06-13 Syngenta Crop Protection Ag Composé insecticide à base de dérivés de pyrazole
WO2024121262A1 (fr) 2022-12-09 2024-06-13 Syngenta Crop Protection Ag Composé insecticide à base de dérivés de pyrazole

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102499218B (zh) * 2011-10-21 2014-04-09 福建农林大学 农药毒理实验预处理装置及方法

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DE3763409D1 (de) * 1986-02-19 1990-08-02 Duphar Int Res Thio-verbindungen und ihre wirkung als fungizide.
DE4405207A1 (de) * 1994-02-18 1995-08-24 Bayer Ag N-Pyrazolylaniline und N-Pyrazolylaminopyridine
JPH08208620A (ja) * 1995-02-03 1996-08-13 Takeda Chem Ind Ltd アミノピラゾール誘導体、その製造法および用途
WO2001007413A1 (fr) * 1999-07-22 2001-02-01 3-Dimensional Pharmaceuticals, Inc. 1-aryle-3-thioalkyle pyrazoles, leur synthese et leur utilisation comme insecticides

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20120190687A1 (en) * 2009-05-29 2012-07-26 Bayer Cropscience Ag Pyrazinylpyrazoles
US9556141B2 (en) 2011-11-21 2017-01-31 Basf Se Process for preparing N-substituted 1H-pyrazole-5-carboxylate compounds and derivatives thereof
WO2013164295A1 (fr) 2012-05-04 2013-11-07 Basf Se Composés contenant du pyrazole substitué et leur utilisation comme pesticides
US9174967B2 (en) 2012-05-04 2015-11-03 Basf Se Substituted pyrazole-containing compounds and their use as pesticides
WO2021151976A1 (fr) * 2020-01-31 2021-08-05 Bayer Aktiengesellschaft Dérivés de l'acide [(1,4,5-trisubstitué-1h-pyrazol-3-yl)sulfanyl]acétique, leurs sels et leur utilisation comme ingrédients herbicides
WO2024121263A1 (fr) 2022-12-09 2024-06-13 Syngenta Crop Protection Ag Composé insecticide à base de dérivés de pyrazole
WO2024121264A1 (fr) 2022-12-09 2024-06-13 Syngenta Crop Protection Ag Composé insecticide à base de dérivés de pyrazole
WO2024121261A1 (fr) 2022-12-09 2024-06-13 Syngenta Crop Protection Ag Composé insecticide à base de dérivés de pyrazole
WO2024121262A1 (fr) 2022-12-09 2024-06-13 Syngenta Crop Protection Ag Composé insecticide à base de dérivés de pyrazole

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WO2009156090A3 (fr) 2010-04-08
AR072673A1 (es) 2010-09-15

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