EP1082009A1 - Fungicide mixtures based on triple oxime ether derivatives and insecticides - Google Patents

Fungicide mixtures based on triple oxime ether derivatives and insecticides

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Publication number
EP1082009A1
EP1082009A1 EP99910371A EP99910371A EP1082009A1 EP 1082009 A1 EP1082009 A1 EP 1082009A1 EP 99910371 A EP99910371 A EP 99910371A EP 99910371 A EP99910371 A EP 99910371A EP 1082009 A1 EP1082009 A1 EP 1082009A1
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EP
European Patent Office
Prior art keywords
alkyl
alkylamino
aryl
hetaryl
alkylaminocarbonyl
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
EP99910371A
Other languages
German (de)
French (fr)
Inventor
Klaus Schelberger
Thomas Grote
Hubert Sauter
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
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BASF SE
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BASF SE
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Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1082009A1 publication Critical patent/EP1082009A1/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton

Definitions

  • the present invention relates to mixtures for controlling harmful fungi and insects which
  • R ⁇ R independently of one another hydrogen or C] . -C alkyl
  • R 2 cyano, nitro, trifluoromethyl, halogen, -CC alkyl or -CC alkoxy;
  • n 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
  • R 3 hydrogen f, cyano, -CC alkyl, -C-C haloalkyl or C 3 -C 6 cycloalkyl;
  • R 4 , R 6 independently of one another hydrogen
  • Di-Ci-C ß alkylamino, Ci-C ö alkylaminocarbonyl, Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C 2 ⁇ C 6 - alkenyl, C 2 -C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C ( NOR 7 ) -A n -R 8 ;
  • Hydrogen C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, where the hydrocarbon radicals of these groups can be partially or completely halogenated or can carry one to three of the following radicals: cyano, nitro, hydroxy, Mercapto, amino, carboxyl, aminocarbonyl,
  • C 3 - C_ -Cycioalkyl C 3 -C 6 -cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino , Carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-C ⁇ -alkyl, Ci-C ö -haloalkyl, Ci-Ce-alkylsulfonyl, C ⁇ -C 6 alkyl sulfoxyl, C -C 6 cycloalkyl, C ⁇ -C 6 alkoxy , -CC 6 -haloalkoxy, -C-C 6 -alkoxycarbonyl, -C-C 6 -alkylthio, -C-C 6 - alkylamino, di-C ⁇ -C 6 -alkylamin
  • A stands for oxygen, sulfur or nitrogen and wherein the nitrogen carries hydrogen or -CC 6 alkyl
  • n 0 or 1
  • R 7 is hydrogen or Ci-C ß- alkyl
  • R 8 is hydrogen or -CC 6 alkyl
  • the object of the present invention was to provide mixtures which, on the one hand, have a good fungicidal action, in particular against fungal diseases in rice, and at the same time have a good insecticidal action. Since pests are usually found in large numbers in the climatic regions in which rice is grown, a combination of fungicidal and insecticidal activity is desirable.
  • EP-A 192.060 common name: Imidacloprid (trade name: Ad ire ®, Gaucho ®, Bayer.);
  • Acetamiprid (trade name: Mospilan, Nipon Soda)
  • IX CAS RN 111 988-49-9, common name: thiacloprid (development product from Bayer);
  • the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
  • isomer mixtures are obtained during the synthesis, however, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the influence of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
  • the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -OCH 3 or the -CH 3 group in relation to the -CO 2 R 1 group).
  • Halogen fluorine, chlorine, bromine and iodine
  • Alkyl straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, e.g. Ci-C ⁇ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbucyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl,
  • Haloalkyl straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl , Trif luormethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodif luormethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2, 2, 2-trif luorethyl, 2-chloro-2-f luorethyl, 2-chloro-2, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
  • Cycloalkyl monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyi and cyclohexyl;
  • Alkenyl straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl
  • Alkynyl straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl 2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-3
  • Heterocyclyl or heterocyclyloxy, heterocyclyl thio and heterocycliclamino three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or (Heterocyclyloxy) via an oxygen atom or (Heterocyclylthio) via a sulfur atom or (Heterocyclylamino) via a nitrogen atom are bound to the structure, such as, for example, 2-tecrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydr 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4 -isoxazolidinyl, 5 -isoxazolidinyl, 3 -isothiazolidinyl, 4-isothiazolidinyl,
  • Aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl aromatic mono- or polycyclic hydrocarbon radicals which directly or (aryloxy) via an oxygen atom (-0-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) are bonded to the skeleton via a sulfonyl group (-SO 2 -), for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;
  • Hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl aromatic mono- or polycyclic radicals which in addition to carbon ring members additionally one to four Nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which directly or (hetaryloxy) via an oxygen atom (-0-) or (hetarylthio) a sulfur atom (-S-), (Hetarylcarbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a sulfonyl group (-S0 2 -) are bound to the skeleton, for example
  • 5-membered heteroaryl containing one to three nitrogen atoms 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-triazol-3-yl and 1, 3, 4-triazol-2- yl;
  • 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and may contain a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-o
  • 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen atom. or may contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1, 3-diene-1, 4-diyl group;
  • 5-membered heteroaryl bound via nitrogen containing one to four nitrogen atoms, or benzo-condensed 5-membered heteroaryl bound via nitrogen, holding one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or one nitrogen and one adjacent one
  • Carbon ring member can be bridged by a buta-1, 3-diene-1, 4-diyl group, these rings being bonded to the device via one of the nitrogen ring members;
  • 6-membered heteroaryl containing one to three or one to four nitrogen atoms 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3, 5-triazin-2-yl, 1, 2, 4-triazin-3-yl and 1,2,4, 5-tetrazin-3 -yl;
  • 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1, 3 -diene-1, 4 -diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
  • Hetarylamino aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are bonded to the structure via a nitrogen atom.
  • R 1 is methyl.
  • R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 .
  • R 3 is CF 3 .
  • R 5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, optionally subst.
  • Aryl or hetaryl is.
  • R 5 for optionally subst.
  • Aryl or hetaryl is.
  • R 5 for optionally subst.
  • R 5 for optionally subst. Furyl, thienyl or pyrrolyl. Furthermore, compounds I are preferred in which R 5 for optionally subst. Oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.
  • R 5 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
  • R 5 is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy, amino, aminocarbonyl, aminothiocarbonyl, halogen, C ⁇ -C -alkyl, C ⁇ - C -haloalkyl, -C-C alkoxy, C ⁇ -C-haloalkoxy, C 1 -C -alkylamino, di-C ⁇ -C - alkylamino, C 1 -C -alkylsulfonyl, C ⁇ -C -alkoxycarbonyl, C ⁇ -C -alkyl- aminocarbonyl or Di-C ⁇ -C-alkylaminocarbonyl.
  • R 4 represents hydrogen, -CC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl .
  • R 4 is C 1 -C 6 -alkyl.
  • the compounds I contained in the mixtures according to the invention are distinguished by an outstanding action against a broad spectrum of phytopathogenic fungi, in particular against fungi from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes.
  • the compounds of the formulas II to IX are used to control animal pests from the class of the insects, arachnids and nematodes. They can be used in crop protection as well as in the hygiene, storage protection and veterinary sectors to control animal pests. They are particularly suitable for controlling the following animal pests:
  • Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula abso- luta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Trumocampidia nia, Thaumocampia- nia, Thaumocampia- poira phera canadensis,
  • Beetles (Coleoptera), e.g. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bru, Bruchus pis Byctiscus betulae, Cassida nebu- losa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc- tata, Diabrotica virgifera, Epilachna varivestis, Epitrix hir- tipennis, Eutinobothrus brasi
  • Two-winged e.g. Aedes aegypti, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macella- ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, fan- nia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia cuprina, Luc
  • Phorbia antiqua Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula ole-racea and Tipula paludosa,
  • Thrips e.g. Frankliniella fusca, Frankiiniella occidentalis, Franklinielia tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
  • Dermatoptera e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,
  • Heteroptera e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara quadrantulais, Pyanma viridula, Pies
  • Plant suckers e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce-rosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiaodumeodona Maconia phiumisodumophone, Macrosia diaumodis, Macrosia diumusumica, Macrosia diodiahumacophus, Macrosia diumusi Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharici
  • Termites e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis,
  • Straight wing aircraft e.g. Acheta domestica, Blatta orien- talis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melano- plus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguini-pes, Melanoplus spretus, Schomannacana america, Nomadascocata americana Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus,
  • Arachnoid such as arachnids (Acarina), e.g. Amblyomma america- num, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoeni-eis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalundxnobinium, Hyalommxxusodusunc me- gnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllo- coptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabieus, Tetranychus Tinnabarinus tawchy
  • Nematodes such as root-bile nematodes, eg Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolius, longica- lodum, undelongeluityu, stock- and leafelenchia dipsaci, Heliocotylenchus mul- ticinetus, Longidorus elongatus, Radopholus similis, Rotylen- chus robustus, Trichodorus primitivus, Tylenchorhynchus clay- toni, Tylenchorhynchus dubius, Pratylenchus neglectus, Praty- lenchusususatati curatusi, Praty- lenchus
  • the mixtures according to the invention can particularly preferably be used to control plant diseases and insect pests in rice.
  • the compounds I and at least one of the compounds II to XI can be applied simultaneously, that is jointly or separately, or in succession, the sequence in the case of separate application generally not having any effect on the control success.
  • the application rates of the mixtures according to the invention, especially for agricultural crop areas, are from 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.5 to 3.0 kg / ha, depending on the type of effect desired.
  • the application rates for the compounds I are 0.01 to 2.5 kg / ha, preferably 0.05 to 2.5 kg / ha, in particular 0.1 to 1.0 kg / ha.
  • application rates of mixture of 0.001 to 250 g / kg of seed preferably 0.01 to 100 g / kg, in particular 0.01 to 50 g / kg, are generally used.
  • the mixtures according to the invention can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-strength aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules and by spraying, atomizing, dusting, scattering or pouring can be applied.
  • the form of application depends on the intended use; in any case, it should ensure that the mixture according to the invention is as fine and uniform as possible.
  • the formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as diluent, other organic solvents can also be used as auxiliary solvents.
  • auxiliaries solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g.
  • Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates)
  • Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
  • alkali, alkaline earth, ammonium salts of aromatic sulfonic acids e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as from
  • Powder sprinklers and dusts can be prepared by mixing or jointly grinding the compounds I and at least one of the compounds II to XI or the mixture of the compounds I and at least one of the compounds II to XI with a solid carrier.
  • Granules e.g. coated granules, impregnated granules or homogeneous granules
  • a solid carrier usually produced by binding the active ingredient or ingredients to a solid carrier.
  • Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, serve, for example, as fillers or solid carriers.
  • ground plastics, as well as fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I and at least one of the compounds II to XI or the mixture of the compounds I and at least one of the compounds II to XI.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR or HPLC spectrum).
  • the use of the compounds I and at least one of the compounds II to XI, the mixtures or the corresponding formulations takes place in such a way that the harmful fungi, their habitat or the plants, seeds, soils, surfaces, materials or spaces to be kept free of them with a fungicidally effective amount of the mixture, or of the compounds I and at least one of the compounds II to XI treated separately.
  • the application can take place before or after the infestation by the harmful fungi.
  • IV An aqueous dispersion of 20 parts by weight of the active ingredients, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide 1 mole of castor oil;
  • V a mixture of 80 parts by weight of the active ingredients, 3 parts by weight of the sodium salt of diisobutylnaphthalene-1-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powder Silica gel; a spray mixture is obtained by finely distributing the mixture in water;
  • IX a stable oily dispersion of 20 parts by weight of the active ingredients, 2 parts by weight of the calcium salt of dodecylbenzene sulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether,
  • the active ingredients are prepared separately or together as a 10% emulsion in a mixture of 63% by weight cyclohexanone and 27% by weight emulsifier and diluted with water in accordance with the desired concentration.
  • ⁇ corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in%
  • ß corresponds to the fungal attack of the untreated (control) plants in%
  • Leaves of "Tai-Nong 67" rice seedlings grown in pots were sprayed to runoff point with aqueous active compound preparation which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were then placed in climatic chambers at 22-24 ° C and 95-99% relative humidity for 6 days. The extent of the development of the infestation on the leaves was then determined visually.

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

Abstract

The invention relates to a) phenylacetic acid derivatives of formula (I) in which the substituents and the index have the meanings cited in the description, and to the salts thereof, and to b) at least one compound of formulas (II) to (XI) in a synergistically effective quantity.

Description

Fungizide Mischungen auf der Basis von Tripeloximetherderivaten und InsektizidenFungicidal mixtures based on triple oxime ether derivatives and insecticides
Beschreibungdescription
Die vorliegende Erfindung betrifft Mischungen zur Bekämpfung von Schadpilzen und Insekten, dieThe present invention relates to mixtures for controlling harmful fungi and insects which
a) Phenylessigsäurederivate der Formel Ia) Phenylacetic acid derivatives of the formula I.
in der die Substituenten und der Index die folgende Bedeutung haben :in which the substituents and the index have the following meaning:
X NOCH3, CHOCH3 oder CHCH3 ;X STILL 3 , CHOCH 3 or CHCH 3 ;
Sauerstoff oder NR;Oxygen or NR;
R^R unabhängig voneinander Wasserstoff oder C].-C -Alkyl;R ^ R independently of one another hydrogen or C] . -C alkyl;
R2 Cyano, Nitro, Trifluormethyl , Halogen, Cι-C -Alkyl oder Cι-C -Alkoxy;R 2 cyano, nitro, trifluoromethyl, halogen, -CC alkyl or -CC alkoxy;
m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht;m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstof f , Cyano , Cι-C -Alkyl , Cι_-C -Halogenalkyl oder C3-C6-Cycloalkyl ;R 3 hydrogen f, cyano, -CC alkyl, -C-C haloalkyl or C 3 -C 6 cycloalkyl;
R4 , R6 unabhängig voneinander Wasserstof f ,R 4 , R 6 independently of one another hydrogen,
Cι-Cιo-Alkyl, C3-C6-Cycloalkyl, C2-C10-Alkenyl, C -Cιo-Alkinyl, Cι-Cι0-Alkylcarbonyl , C2-Cι0-Alkenyl - carbonyl, C3-Cχo-Alkinylcarbonyl oder Cι-Cιo-Alkyl- sulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgen- den Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl , Aminothio- carbonyl, Halogen, Cι-C6-Alkyl, Cι-C6-Halogenalkyl, Cι-C6-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl, Cι-C6-Alkoxy, Cι-C6-Halogenalkoxy, Cι-C6-Alkoxycarbonyl, Cι-C6-Alkyl- thio, Cι-C6-Alkylamino, Di-Ci-Cö-alkylamino, Ci-Cö-Alkylaminocarbonyl , Di-Cι-C6-alkylaminocarbonyl , Ci-Cδ-Alkylaminothiocarbonyl, Di-Ci-Cö-alkylaminothio- carbonyl, C2-C6-Alkenyl, C2-C6-Alkenyloxy, C3-C6-Cyclo- alkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Hetero- cyclyloxy, Benzyl , Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy und Hetarylthio, wobei die cycli- schen Gruppen ihrerseits partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy,Cι-Cιo-alkyl, C 3 -C 6 cycloalkyl, C 2 -C 10 alkenyl, C -Cιo alkynyl, Cι-Cι 0 -alkylcarbonyl, C 2 -Cι 0 -alkenyl - carbonyl, C3-Cχo-alkynylcarbonyl or -CC-alkyl sulfonyl, where these residues can be partially or completely halogenated or one to three of the following can carry the groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, Aminothio- carbonyl, halo, Cι-C 6 -alkyl, C 6 haloalkyl, Cι-C 6 alkylsulfonyl, Cι-C 6 alkylsulfoxyl, Cι-C 6 -alkoxy, C 6 haloalkoxy, Cι-C6 alkoxycarbonyl, Cι-C 6 -alkylthio, Cι-C 6 alkylamino, di-Ci-COE-alkylamino, Ci- Cö-alkylaminocarbonyl, di-Cι-C 6 -alkylaminocarbonyl, Ci-Cδ-alkylaminothiocarbonyl, di-Ci-Cö-alkylaminothio-carbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, C 3 -C 6 -Cycloalkyl, C 3 -C 6 -cycloalkyloxy, heterocyclyl, heterocyclicoxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy and hetarylthio, where the cyclic groups can in turn be partially or completely halogenated or one can carry up to three of the following groups: cyano, nitro, hydroxy,
Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothio- carbonyl, Halogen, Ci-Cö-Alkyl, Cx-Cg-Halogenalkyl, Ci-Cθ-Alkylsulfonyl, Ci-Cβ-Alkylsulfoxyl, C3-C6-Cyclo- alkyl, Cι-C6-Alkoxy, Cι-C6-Halogenalkoxy, Cι-C6-Alkyl- oxycarbonyl, Ci-Cδ-Alkylthio, Ci-Cg-Alkylamino,Mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cö-alkyl, Cx-Cg-haloalkyl, Ci-Cθ-alkylsulfonyl, Ci-Cβ-alkylsulfoxyl, C 3 -C 6 cycloalkyl, Cι- C 6 -alkoxy, -C-C 6 -haloalkoxy, -C-C 6 -alkyl-oxycarbonyl, Ci-C δ -alkylthio, Ci-Cg-alkylamino,
Di-Ci-Cß-Alkylamino , Ci-Cö-Alkylaminocarbonyl , Di-Ci-Cg-Alkylaminocarbonyl , Ci-Cg-Alkylaminothio- carbonyl, Di-Ci-Cg-Alkylaminothiocarbonyl , C2~C6- Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio oder C(=NOR7) -An-R8;Di-Ci-C ß alkylamino, Ci-C ö alkylaminocarbonyl, Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C 2 ~ C 6 - alkenyl, C 2 -C6-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio or C (= NOR 7 ) -A n -R 8 ;
Aryl, Arylcarbonyl, Arylsulfonyl , Hetaryl, Hetaryl - carbonyl oder Hetarylsulfonyl , wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl , Halogen, Ci-Cß-Alkyl, Cι-C6-Halogenalkyl, Ci-Cβ-Alkylcarbonyl , Cι-C6-Alkyl- sulfonyl, Cι-C6-Alkylsulfoxyl , C3-C6-Cycloalkyl ,Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these residues can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen , C ß -alkyl, C 6 haloalkyl, Ci-Cβ alkyl-carbonyl, Cι-C6 alkyl sulfonyl, Cι-C 6 alkylsulfoxyl, C 3 -C 6 cycloalkyl,
Cι-C6~Alkoxy, Cι-C6-Halogenalkoxy, Ci-Cö-Alkyloxy- carbonyl, Ci-Cß-Alkylthio, Ci-Cβ-Alkylamino, Di-Ci-Cδ- Alkylamino, Ci-Cg-Alkylaminocarbonyl, Di-Ci-Cg-Alkyl- aminocarbonyl , Ci-Cg-Alkylaminothiocarbonyl , Di-Ci-Cδ- Alkylaminothiocarbonyl, C2-C6-Alkenyl , C2-C6-Alkenyl- oxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl, Hetaryloxy oder C (=NOR7 ) -An-R8;Cι-C ~ 6 alkoxy, Cι-C 6 haloalkoxy, Ci-C ö alkyloxy- carbonyl, Ci-CSS-alkylthio, Ci-Cβ alkylamino, di-Ci-Cδ- alkylamino, Ci-Cg-alkylaminocarbonyl, di -Ci-Cg-alkyl aminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-C δ - alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl , Hetaryloxy or C (= NOR 7 ) -A n -R 8 ;
Wasserstoff, Cι-C6-Alkyl, C2-C6-Alkenyl, C2-C6-Alkinyl , wobei die Kohlenwasserstoffreste dieser Gruppen partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl,Hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, where the hydrocarbon radicals of these groups can be partially or completely halogenated or can carry one to three of the following radicals: cyano, nitro, hydroxy, Mercapto, amino, carboxyl, aminocarbonyl,
Aminothiocarbonyl , Halogen, Cι-C6-Alkylaminocarbonyl, Di-Cι-C6-alkylaminocarbonyl , Cι-C6-Alkylaminothio- carbonyl, Di-Ci-Cβ-alkylaminothiocarbonyl, Ci-Cö-Alkyl- sulfonyl, Cι-C6-Alkylsulfoxyl, Cι-C6-Alkoxy, Cι-C6- Halogenalkoxy, Cι-C6-Alkoxycarbonyl , Cι-C6-Alkylthio,Aminothiocarbonyl, halogen, Cι-C6 alkylaminocarbonyl, di-Cι-C 6 alkylaminocarbonyl, Cι-C 6 -Alkylaminothio- carbonyl, di-Ci-Cβ-alkylaminothiocarbonyl, C ö alkyl sulfonyl, Cι-C 6 -Alkylsulfoxyl, -CC 6 alkoxy, -C- 6 - haloalkoxy, -C- 6 alkoxycarbonyl, -C- 6 alkylthio,
Cι-C6-Alkylamino, Di-Cι-C6-alkylamino, C2-C6-Alkenyloxy, C3-C6-Cycloalkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Heterocyclyloxy, Aryl, Aryloxy, Aryl-Cx- -alkoxy, Arylthio, Aryl-Cι-C -alkylthio, Hetaryl, Hetaryloxy, Hetaryl-Cι-C4-alkoxy, Hetarylthio, Hetaryl-Cι-C4-alkyl- thio, wobei die cyclischen Reste ihrerseits partiell oder vollständig halogeniert sein können und/oder ein bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Ci-Cβ-Alkyl,C 1 -C 6 alkylamino, di-C 1 -C 6 alkylamino, C 2 -C 6 alkenyloxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl Cx -alkoxy, arylthio, aryl-Cι-C -alkylthio, hetaryl, hetaryloxy, hetaryl-Cι-C4-alkoxy, hetarylthio, hetaryl-Cι-C 4 -alkylthio, where the cyclic radicals in turn may be partially or fully halogenated can be and / or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-Cβ-alkyl,
Cι-C6-Halogenalkyl, Cι-C6-Alkylsulfonyl, Ci-Cδ-Alkyl- sulfoxyl, C3C6-Cycloalkyl, Cι-C6-Alkoxy, Cι-C6-Halogen- alkoxy, Ci-Cδ-Alkoxycarbonyl, Ci-Cβ-Alkylthio, Cι-C6- Alkylamino, Di-Ci-Cβ-alkylamino, Ci-Cβ-Alkylamino- carbonyl, Di-Ci-Cg-alkylaminocarbonyl , Ci-Cδ-Alkyl- aminothiocarbonyl , Di-Cι-C6-alkylaminothiocarbonyl, C2-C6-Alkenyl , C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio und C(=NOR7) -An-R8;Cι-C 6 haloalkyl, Cι-C 6 alkylsulfonyl, Ci-C δ alkyl- sulfoxyl, C 3 C 6 cycloalkyl, Cι-C 6 -alkoxy, halo-C 6 alkoxy, Ci-Cδ- Alkoxycarbonyl, Ci-Cβ-alkylthio, Cι-C 6 - alkylamino, di-Ci-Cβ-alkylamino, Ci-Cβ-alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-C δ -alkyl- aminothiocarbonyl, di- Cι-C 6 -alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NOR 7 ) -A n -R 8 ;
C3 - C_ -Cycioalkyl, C3 -C6 -Cycloalkenyl, Heterocyclyl, Aryl, Hetaryl, wobei die cyclischen Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cβ-Alkyl, Ci-Cö-Halogenalkyl, Ci-Ce-Alkylsulfonyl, Cι-C6-Alkyl- sulfoxyl, C -C6-Cycloalkyl , Cι-C6-Alkoxy, Cι-C6-Halogen- alkoxy, Cι-C6-Alkoxycarbonyl , Cι-C6-Alkylthio, Cι-C6- Alkylamino, Di-Cι-C6-alkylamino, Cι-C6-Alkylamino- carbonyl, Di-Ci-Cg-alkylaminocarbonyl, Cι-C6-Alkyl- aminothiocarbonyl , Di-Ci-Cg-alkylaminothiocarbonyl , C2-C6-Alkenyl, C2-C6-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl und Hetaryloxy;C 3 - C_ -Cycioalkyl, C 3 -C 6 -cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino , Carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cβ-alkyl, Ci-C ö -haloalkyl, Ci-Ce-alkylsulfonyl, Cι-C 6 alkyl sulfoxyl, C -C 6 cycloalkyl, Cι-C 6 alkoxy , -CC 6 -haloalkoxy, -C-C 6 -alkoxycarbonyl, -C-C 6 -alkylthio, -C-C 6 - alkylamino, di-Cι-C 6 -alkylamino, Cι-C 6 -alkylamino-carbonyl, Di -Ci-Cg-alkylaminocarbonyl, -C-C 6 alkyl aminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and Hetaryloxy;
wobei A für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Cι-C6-Alkyl trägt;in which A stands for oxygen, sulfur or nitrogen and wherein the nitrogen carries hydrogen or -CC 6 alkyl;
n 0 oder 1 bedeutet;n represents 0 or 1;
R7 Wasserstoff oder Ci-Cß-Alkyl bedeutet undR 7 is hydrogen or Ci-C ß- alkyl and
R8 Wasserstoff oder Cι-C6-Alkyl bedeutet,R 8 is hydrogen or -CC 6 alkyl,
sowie deren Salze,and their salts,
undand
b) mindestens einem Insektizid ausgewählt aus Insektiziden der Formeln II bis XIb) at least one insecticide selected from insecticides of the formulas II to XI
.N.N
0 ι ι + 0 ι ι +
Der vorliegenden Erfindung lag die Aufgabe zugrunde, Mischungen zur Verfügung zu stellen, die einerseits eine gute fungizide Wir- kung, insbesondere gegen Pilzerkrankungen in Reis und gleichzeitig eine gute insektizide Wirkung zeigen. Da in den klimatischen Regionen in denen Reis angebaut wird, auch Schadinsekten in der Regel in großer Zahl vorkommen, ist eine Kombination von fungizider und insektizider Wirkung wünschenswert.The object of the present invention was to provide mixtures which, on the one hand, have a good fungicidal action, in particular against fungal diseases in rice, and at the same time have a good insecticidal action. Since pests are usually found in large numbers in the climatic regions in which rice is grown, a combination of fungicidal and insecticidal activity is desirable.
Diese Aufgabe wird erfindungsgemäß durch die Mischungen gemäß Anspruch 1 gelöst.This object is achieved according to the invention by the mixtures according to claim 1.
Die Verbindungen der Formel I sowie deren Herstellung sind an sich bekannt und in der Literatur beschrieben (WO 97/15,552) .The compounds of formula I and their preparation are known per se and are described in the literature (WO 97/15,552).
Die Insektizide der Formeln II bis IX sind ebenfalls bekannt und in der Literatur beschrieben. Darüber hinaus sind sie unter den nachfolgend in Klammern genannten Handelsnamen kommerziell erhältlich:The insecticides of formulas II to IX are also known and are described in the literature. They are also commercially available under the trade names below in brackets:
II: EP-A 192,060, Common name: Imidacloprid (Handelsname: Ad ire®, Gaucho®, Fa. Bayer) ;II: EP-A 192.060, common name: Imidacloprid (trade name: Ad ire ®, Gaucho ®, Bayer.);
III: Common name: Acetamiprid (Handelsname: Mospilan , Fa. Nip- pon Soda)III: Common name: Acetamiprid (trade name: Mospilan, Nipon Soda)
IV: CAS RN 120738-89-8, Common name: Nitenpyram (Handelsname: Bestgard®, Fa. Takeda Chemicals) ; V: Colliot et al., Proc. Br. Conf . Dis. 1992, 1, 29, Common name: Fipronil (Handelsname: Regent , Fa. Rhone-Poulenc) ;IV: CAS RN 120738-89-8, common name: nitenpyram (trade name: Bestgard ®, from Takeda Chemicals.); V: Colliot et al., Proc. Br. Conf. Dis. 1992, 1, 29, common name: Fipronil (trade name: Regent, Rhone-Poulenc);
VI: US 3,474,170; US 3,474,171 und DE-C 1,493,646; Common name: C Caarrbboofuran (Handelsname Curaterr®, Fa. Bayer; Furadan®, Fa FMC) ;VI: US 3,474,170; US 3,474,171 and DE-C 1,493,646; Common name: C Caarrbboofuran (trade name Curaterr ®, Bayer; Furadan ®, from FMC.);
VII: Proc. Br. Crop Prot. Conf., 1979, Vol. 2, 557, Common name: Carbosulfan (Handelsname: Marshall®, Fa. FMC) ;VII: Proc. .... Br Crop Prot Conf, 1979, Vol 2, 557, common name: carbosulfan (trade name: Marshall ®, from FMC.);
VIII: FR-A 2,489,329; Proc. Int. Congr. Plant Prot. lOth, 1983, 2, 360, Common name: Benfuracarb (Handelsname: Oncol®, Fa. Otsuka; Furacon®, Fa. Siapa Chem.);VIII: FR-A 2,489,329; Proc. Int. Congr. . Plant Prot Loth, 1983, 2, 360, common name: benfuracarb (trade name:; Furacon ®, Fa Siapa Chem Oncol ®, from Otsuka...);
IX: CAS RN 111 988-49-9, Common name: Thiacloprid (Entwicklungsprodukt der Fa. Bayer);IX: CAS RN 111 988-49-9, common name: thiacloprid (development product from Bayer);
X: Proc. of the 1998 Brighton Conference "Pests and Diseases" ,X: Proc. of the 1998 Brighton Conference "Pests and Diseases",
Vol. 1, S. 21-26 (MTI 446, Fa. Mitsui);Vol. 1, pp. 21-26 (MTI 446, Mitsui);
XI: Proc. of the Brighton Conference on Pests and Diseases,XI: Proc. of the Brighton Conference on Pests and Diseases,
Vol. 1, S. 27-36 (CGA 293 343, Fa. Novartis) .Vol. 1, pp. 27-36 (CGA 293 343, Novartis).
Die Verbindungen I können bei der Herstellung aufgrund ihrer C=C und C=N Doppelbindungen als E/Z-Isomerengemische anfallen, die z.B. durch Kristallisation oder Chromatographie in üblicher Weise in die Einzelverbindungen getrennt werden können.Due to their C = C and C = N double bonds, the compounds I can be produced as E / Z isomer mixtures which, for example, can be separated into the individual compounds by crystallization or chromatography in the usual way.
Sofern bei der Synthese Isomerengemische anfallen, ist im all- gemeinen jedoch eine Trennung nicht unbedingt erforderlich, da sich die einzelnen Isomere teilweise während der Aufbereitung für die Anwendung oder bei der Anwendung (z.B. unter Licht-, Säureoder Baseneinwirkung) ineinander umwandeln können. Entsprechende Umwandlungen können auch nach der Anwendung, beispielsweise bei der Behandlung von Pflanzen in der behandelten Pflanze oder im zu bekämpfenden Schadpilz oder tierischen Schädling erfolgen.If isomer mixtures are obtained during the synthesis, however, a separation is generally not absolutely necessary, since the individual isomers can partially convert into one another during preparation for use or during use (e.g. under the influence of light, acid or base). Corresponding conversions can also take place after use, for example in the treatment of plants in the treated plant or in the harmful fungus or animal pest to be controlled.
In Bezug auf die C=X Doppelbindung werden hinsichtlich ihrer Wirksamkeit die E-Isomere der Verbindungen I bevorzugt (Konfigu- ration bezogen auf die -OCH3 bzw. die -CH3 -Gruppe im Verhältnis zur -CO2R1 Gruppe) .With regard to the C = X double bond, the E isomers of the compounds I are preferred in terms of their activity (configuration based on the -OCH 3 or the -CH 3 group in relation to the -CO 2 R 1 group).
In Bezug auf die -C (R3) =NOCH2- Doppelbindung werden hinsichtlich ihrer Wirksamkeit die cis-Isomere der Verbindungen I bevorzugt (Konfiguration bezogen auf den Rest R3 im Verhältnis zur -OCH2- Gruppe) . Bei der eingangs angegebenen Definitionen der Verbindungen I wurden Sammelbegriffe verwendet, die allgemein repräsentativ für die folgenden Gruppen stehen:With regard to the -C (R 3 ) = NOCH 2 double bond, the cis isomers of the compounds I are preferred in terms of their activity (configuration based on the radical R 3 in relation to the -OCH 2 group). In the definitions of the compounds I given at the outset, collective terms were used which are generally representative of the following groups:
Halogen: Fluor, Chlor, Brom und Jod;Halogen: fluorine, chlorine, bromine and iodine;
Alkyl: geradkettige oder verzweigte Alkylgruppen mit 1 bis 4, 6 oder 10 Kohlenstoffatomen, z.B. Ci-Cβ-Alkyl wie Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1-Methyl-propyl, 2-Methylpropyl, 1, 1-Dimethylethyl, Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2 , 2-Di-methylpropyl, 1-Ethylpropyl, Hexyl, 1, 1-Dimethylpropyl, 1, 2-Dimethylpropyl , 1-Methylpentyl , 2-Methyl - pentyl, 3-Methylpentyl, 4-Methylpentyl , 1 , 1-Dimethylbutyl , 1, 2-Dimethylbutyl, 1 , 3-Dimethylbutyl , 2 , 2-Dimethylbucyl, 2,3-Dimethylbutyl, 3 , 3-Dimethylbutyl , 1-Ethylbutyl , 2-Ethylbutyl, 1, 1, 2-Trimethylpropyl, 1 , 2 , 2-Trimethylpropyl , i-Ethyl-1-methyl - propyl und 1- Ethyl-2-methylpropyl ;Alkyl: straight-chain or branched alkyl groups with 1 to 4, 6 or 10 carbon atoms, e.g. Ci-Cβ-alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbucyl, 2,3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2, 2- Trimethylpropyl, i-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl;
Halogenalkyl : geradkettige oder verzweigte Alkylgruppen mit 1 bis 6 Kohlenstoffatomen, wobei in diesen Gruppen teilweise oder vollständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können, z.B. Cι-C2~Halogenalkyl wie Chlor - methyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Dif luormethyl, Trif luormethyl, Chlorfluormethyl, Dichlorf luormethyl, Chlordif luormethyl, 1-Fluorethyl , 2-Fluorethyl , 2 , 2-Difluorethyl , 2, 2, 2-Trif luorethyl, 2-Chlor-2-f luorethyl, 2-Chlor-2 , 2-dif luorethyl, 2, 2-Dichlor-2-f luorethyl, 2 , 2 , 2-Trichlorethyl und Penta- fluorethyl ;Haloalkyl: straight-chain or branched alkyl groups with 1 to 6 carbon atoms, in which groups the hydrogen atoms can be partially or completely replaced by halogen atoms as mentioned above, for example C 1 -C 2 -haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl , Trif luormethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodif luormethyl, 1-fluoroethyl, 2-fluoroethyl, 2, 2-difluoroethyl, 2, 2, 2-trif luorethyl, 2-chloro-2-f luorethyl, 2-chloro-2, 2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl;
Cycloalkyl : monocyclische Alkylgruppen mit 3 bis 6 Kohlenstoff - ringgliedern, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyi und Cyclohexyl ;Cycloalkyl: monocyclic alkyl groups with 3 to 6 carbon ring members, e.g. Cyclopropyl, cyclobutyl, cyclopentyi and cyclohexyl;
Alkenyl: geradkettige oder verzweigte Alkenylgruppen mit 2 bis 6 oder 10 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, z.B. C2-C6-Alkenyl wie Ethenyl, 1-Propenyl, 2-Propenyl, 1-Methylethenyl , 1-Butenyl, 2-Butenyl, 3-Butenyl, 1-Methyl-l-propenyl, 2-Methyl-l-propenyl , l-Methyl-2-propenyl, 2-Methyl-2-propenyl, 1-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1-Methyl-l-butenyl , 2-Methyl-l-butenyl , 3-Methyl-l- butenyl, l-Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2- butenyl, l-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3- butenyl, 1 , l-Dimethyl-2-propenyl, 1 , 2-Dimethyl-l-propenyl, 1, 2-Dimethyl-2-propenyl, 1-Ethyl-l-propenyl, l-Ethyl-2-propenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl,Alkenyl: straight-chain or branched alkenyl groups with 2 to 6 or 10 carbon atoms and a double bond in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2- Butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2- butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, l-dimethyl-2-propenyl, 1, 2-dimethyl-l-propenyl, 1, 2- Dimethyl-2-propenyl, 1-ethyl-l-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl,
1-Methyl-l-pentenyl, 2-Methyi-l-pentenyl , 3-Methyl-l-pentenyl, 4-Methyl-l-pentenyl, l-Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl , l-Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, l-Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 , l-Dimethyl-2-butenyl , 1 , l-Di-methyl-3- butenyl, 1, 2-Dimethyl-l-butenyl, 1, 2-Dimethyl-2-butenyl ,1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l- Methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, l-dimethyl-2-butenyl, 1, l-dimethyl-3- butenyl, 1, 2-dimethyl-l-butenyl, 1, 2-dimethyl-2-butenyl,
1, 2-Dimethyl-3-butenyl, 1, 3-Dimethyl-l-butenyl , 1, 3-Dimethyl-2- butenyl, 1, 3-Dimethyl-3-butenyl , 2 , 2-Dimethyl-3-butenyl , 2, 3-Dimethyl-l-butenyl, 2 , 3-Dimethyl-2 -butenyl , 2, 3-Dimethyl-3- butenyl, 3 , 3-Dimethyl-l-butenyl, 3, 3-Dimethyl-2-butenyl , 1-Ethyl-l-butenyl, l-Ethyl-2-butenyl, l-Ethyl-3-butenyl , 2-Ethyl-l-butenyl, 2-Ethyl-2-butenyl , 2-Ethyl-3-butenyl , 1, 1, 2-Trimethyl-2-propenyl, 1- Ethyl-l-methyl-2-propenyl, l-Ethyl-2-methyl-l-propenyl und l-Ethyl-2-methyl-2-propenyl ;1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl;
Alkinyl: geradkettige oder verzweigte Alkinylgruppen mit 2 bis 10 Kohlenstoffatomen und einer Dreifachbindung in einer beliebigen Position, z.B. C2-C6-Alkinyl wie Ethinyl, 2-Propinyl, 2-Butinyl, 3-Butinyl, l-Methyl-2-propinyl , 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-2-butinyl , l-Methyl-3-butinyl , 2-Methyl-3-butinyl, 1, l-Dimethyl-2-propinyl, l-Ethyl-2-propinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, l-Methyl-2-pentinyl, l-Methyl-3-pentinyI, l-Methyl-4-pentinyl , 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3-Methyl-4-pentinyl , 4-Methyl-2-pentinyl, 1, l-Dimethyl-2-butinyl, 1, l-Dimethyl-3-butinyl, 1 , 2-Dimethyl- 3-butinyl, 2 , 2-Dimethyl-3-butinyl, l-Ethyl-2-butinyl , 1-Ethyl- 3-butinyl, 2-Ethyl-3-butinyl und l-Ethyl-l-methyl-2-propinyl ,-Alkynyl: straight-chain or branched alkynyl groups with 2 to 10 carbon atoms and a triple bond in any position, for example C 2 -C 6 -alkynyl such as ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl-2-butynyl, l-methyl-3-butynyl, 2-methyl-3-butynyl, 1, l-dimethyl-2-propynyl, l-ethyl 2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, l-methyl-2-pentynyl, l-methyl-3-pentynyl, l-methyl-4-pentynyl, 2-methyl-3- pentinyl, 2-methyl-4-pentinyl, 3-methyl-4-pentinyl, 4-methyl-2-pentinyl, 1, l-dimethyl-2-butinyl, 1, l-dimethyl-3-butinyl, 1, 2- Dimethyl-3-butynyl, 2, 2-dimethyl-3-butynyl, l-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and l-ethyl-l-methyl-2- propinyl, -
Heterocyclyl bzw. Heterocyclyloxy, Heterocyclyl thio und Hetero- cyclylamino: drei- bis sechsgliedrige, gesättigte oder partiell ungesättigte mono- oder polycyclische Heterocyclen, die ein bis drei Hereroatome ausgewählt aus einer Gruppe bestehend aus Sauerstoff, Stickstoff und Schwefel enthalten, und welche direkt bzw. (Heterocyclyloxy) über ein Sauerstoffatom oder (Heterocyclylthio) über ein Schwefelatom oder (Heterocyclylamino) über ein Stick- stoffatom an das Gerüst gebunden sind, wie z.B. 2 -Tecrahydro- furanyl, Oxiranyl, 3 -Tetrahydrofuranyl , 2 -Tetrahydrothienyl, 3-Tetrahydrothienyl, 2 -Pyrrolidinyl, 3 -Pyrrolidinyl , 3-Isoxazol- dinyl, 4 -Isoxazolidinyl, 5 -Isoxazolidinyl, 3 -Isothiazolidinyl, 4 - Isothiazolidinyl , 5 - Isothiazolidinyl , 3 -Pyrazolidinyl, 4 -Pyrazolidinyl, 5 -Pyrazolidinyl , 2 -Oxazolidinyl , 4 -Oxazolidinyl, 5-Oxazolidinyl , 2 -Thiazolidinyl, 4 -Thiazolidinyl , 5-Thia- zolidinyl, 2 - Imidazolidinyl , 4 - Imidazolidinyl , 1,2,4-Oxa- diazolidin-3 -yl, 1 , 2 , 4 -Oxadiazolidin- 5 -yl , 1 , 2 , 4 -Thiadiazolidin- 3-yl, 1, 2, 4-Thiadiazolidin-5-yl, 1, 2 , 4 -Triazolidin- 3 -yl , 1, 3, 4-Oxadiazolidin-2-yl, 1 , 3 , 4 -Thiadiazolidin- 2 -yl , 1,3,4-Tri- azolidin-2 -yl, 2 , 3 -Dihydrofur - 2 -yl , 2 , 3 -Dihydrofur- 3 -yl , 2, -Dihydro-fur-4-yl, 2, 3 -Dihydro- fur- 5 -yl , 2, 5 -Dihydro-fur -2 -yl, 2, 5-Dihydro-fur-3-yl, 2 , 3 -Dihydrothien- 2 -yl , 2,3-Dihydro- thien-3-yl, 2 , 3 -Dihydrothien- 4 -yl , 2 , 3 -Dihydrothien- 5 -yl, 2, 5-Dihydrothien-2-yl, 2 , 5 -Dihydrothien-3 -yl, 2,3-Dihydro- pyrrol-2-yl, 2 , 3 -Dihydropyrrol -3 -yl , 2 , 3 -Dihydropyrrol - 4 -yl, 2, 3 -Dihydropyrrol -5 -yl, 2 , 5 -Dihydropyrrol - 2 -yl , 2,5-Dihydro- pyrrol -3 -yl, 2,3 -Dihydroisoxazol -3 -yl, 2,3 -Dihydroisoxazol-4 -yl, 2, 3 -Dihydroisoxazol- 5 -yl, 4, 5 -Dihydroisoxazol - 3 -yl , 4, 5 -Dihydroisoxazol -4 -yl, 4 , 5 -Dihydroisoxazol -5 -yl, 2 , 5-Dihydroisothia- zol-3-yl, 2, 5-Dihydroisothiazol-4-yl, 2 , 5 -Dihydroisothiazol -5-yl, 2, 3-Dihydroisopyrazol-3 -yl, 2, 3 -Dihydroisopyrazol- -yl , 2,3-Dihy- droisopyrazol-5-yl, 4 , 5 -Dihydroisopyrazol - 3 -yl , 4, 5 -Dihydroiso - pyrazol-4-yl, 4, 5 -Dihydroisopyrazol- 5-yl, 2 , 5 -Dihydroisopyrazol -3 -yl, 2 , 5 -Dihydroisopyrazol -4 -yl, 2 , 5 -Dihydroisopyrazol -5 -yi, 2, 3 -Dihydrooxazol-3 -yl, 2 , 3 -Dihydrooxazol -4 -yl , 2,3-Dihydro- oxazol-5-yl, 4 , 5 -Dihydrooxazol -3 -yl, 4 , 5 -Dihydrooxazol -4 -yl, 4, 5 -Dihydrooxazol -5-yl, 2 , 5 -Dihydrooxazol - 3 -yl , 2,5-Dihydro- oxazol-4-yl, 2 , 5 -Dihydrooxazol -5 -yl, 2 , 3 -Dihydrothiazol -2 -yl, 2, 3 -Dihydrothiazol -4 -yl, 2 , 3 -Dihydrothiazol - 5 -yl , 4,5-Dihydro- thiazol-2-yl, 4, 5 -Dihydrothiazol -4 -yl, 4 , 5 -Dihydrothiazol- 5-yl, 2, 5-Dihydrothiazol-2-yl, 2 , 5 -Dihydrothiazol - 4 -yl , 2,5-Dihydro- thiazol - 5-yl , 2,3 -Dihydroimidazol-2-yl , 2,3 -Dihydroimidazol-4 -yl, 2, 3-Dihydroimidazol-5-yl, 4, 5 -Dihydroimidazol - 2 -yl , 4, 5-Dihydro- imidazol - -yl, , 5 -Dihydroimidazol -5 -yl, 2 , 5 -Dihydroimidazol - 2-yl, 2 , 5 -Dihydroimidazol -4 -yl, 2 , 5 -Dihydroimidazol - 5 -yl, 2 -Morpholinyl, 3 -Morpholinyl , 2 -Piperidinyl, 3 - Piperidinyl ,Heterocyclyl or heterocyclyloxy, heterocyclyl thio and heterocycliclamino: three- to six-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three herero atoms selected from a group consisting of oxygen, nitrogen and sulfur, and which directly or (Heterocyclyloxy) via an oxygen atom or (Heterocyclylthio) via a sulfur atom or (Heterocyclylamino) via a nitrogen atom are bound to the structure, such as, for example, 2-tecrahydrofuranyl, oxiranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydr 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4 -isoxazolidinyl, 5 -isoxazolidinyl, 3 -isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3 -pyrazolidinyl, 4 -pyrazolidinyl, 5 -pyrazolidinyl, 2 -oxazolidinyl 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2 - imidazolidinyl, 4 - imidazolidinyl, 1,2,4-oxadiazolidin-3 -yl, 1, 2, 4 -oxadiazolidin-5 -yl, 1, 2, 4 -thiadiazolidin-3-yl, 1, 2, 4-thiadiazolidin-5-yl, 1, 2, 4 -triazolidin-3 -yl, 1, 3, 4-oxadiazolidin-2-yl, 1, 3, 4 -thiadiazolidin- 2 -yl, 1,3,4-triazolidin-2 -yl, 2, 3 -dihydrofur - 2 -yl, 2, 3 -dihydrofur- 3 -yl, 2, -dihydro-fur-4-yl, 2, 3 -dihydro-fur-5 -yl, 2, 5 -dihydro-fur-2 -yl, 2,5-dihydro-fur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydro-thien-3-yl, 2,3-dihydrothien-4-yl, 2,3-dihydrothiene 5 -yl, 2, 5-dihydrothien-2-yl, 2, 5 -dihydrothien-3 -yl, 2,3-dihydropyrrol-2-yl, 2, 3 -dihydropyrrole -3 -yl, 2, 3 - Dihydropyrrole - 4 -yl, 2, 3 -dihydropyrrole -5 -yl, 2, 5 -dihydropyrrole - 2 -yl, 2,5-dihydropyrrole -3 -yl, 2,3 -dihydroisoxazole -3 -yl, 2, 3 -dihydroisoxazole-4 -yl, 2, 3 -dihydroisoxazole- 5 -yl, 4, 5 -dihydroisoxazole-3 -yl, 4, 5 -dihydroisoxazole -4 -yl, 4, 5 -dihydroisoxazole -5 -yl, 2, 5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2,5-dihydroisothiazol -5-yl, 2,3-dihydroisopyrazol-3-yl, 2,3-dihydroisopyrazole-yl, 2 , 3-Dihydroisopyrazol-5-yl, 4, 5 -dihydroisopyrazol - 3 -yl, 4, 5 -dihydroiso - pyrazol-4-yl, 4, 5 -dihydroisopyrazol- 5-yl, 2, 5 -dihydroisopyrazole -3 -yl, 2, 5 -dihydroisopyrazole -4 -yl, 2, 5 -dihydroisopyrazole -5 -yi, 2, 3 -dihydrooxazol-3 -yl, 2, 3 -dihydrooxazole -4 -yl, 2,3-dihydrooxazole -5-y 1,5-dihydrooxazole -3 -yl, 4,5-dihydrooxazole -4 -yl, 4,5-dihydrooxazole -5-yl, 2,5-dihydrooxazole - 3 -yl, 2,5-dihydro-oxazole- 4-yl, 2,5-dihydrooxazole -5 -yl, 2,3-dihydrothiazole -2-yl, 2,3-dihydrothiazole -4-yl, 2,3-dihydrothiazole - 5-yl, 4,5-dihydro thiazol-2-yl, 4,5-dihydrothiazole -4 -yl, 4,5-dihydrothiazol-5-yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazole - 4 -yl, 2,5- Dihydro-thiazol-5-yl, 2,3-dihydroimidazol-2-yl, 2,3-dihydroimidazol-4-yl, 2,3-dihydroimidazol-5-yl, 4,5-dihydroimidazol-2-yl, 4, 5-dihydroimidazole - -yl,, 5 -dihydroimidazole -5 -yl, 2, 5 -dihydroimidazol - 2-yl, 2, 5 -dihydroimidazole -4 -yl, 2, 5 -dihydroimidazole - 5 -yl, 2 - Morpholinyl, 3-morpholinyl, 2 -piperidinyl, 3-piperidinyl,
4 - Piperidinyl, 3 -Tetrahydropyridazinyl, 4 -Tetrahydropyridazinyl, 2 -Tetrahydropyrimidinyl, 4 -Tetrahydropyrimidinyl , 5 -Tetrahydro- pyrimidinyl, 2 -Tetrahydropyrazinyl , 1,3,5 -Tetrahydrotriazin-2 -yl, 1,2,4 -Tetrahydrotriazin-3 -yl , 1,3 -Dihydrooxazin- 2 -yl, 1, 3-Dithian-2-yl, 2 -Tetrahydropyranyl , 1, 3 -Dioxolan-2 -yl, 3,4,5, 6-Tetrahydropyridin-2-yl, 4H-1, 3 -Thiazin-2 -yl, 4H-3, l-Benzothiazin-2-yl, 1, l-Dioxo-2, 3,4, 5 - tetrahydrothien-2 -yl, 2H-1, 4 -Benzothiazin-3-yl, 2H- 1 , 4 -Benzoxazin- 3 -yl , 1,3-Dihydro- oxazin-2-yl, 1, 3 -Dithian-2 -yl;4 - piperidinyl, 3-tetrahydropyridazinyl, 4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl, 4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl, 1,3,5-tetrahydrotriazin-2 -yl, 1,2,4-tetrahydrotriazine 3 -yl, 1,3-dihydrooxazin-2 -yl, 1, 3-dithian-2-yl, 2-tetrahydropyranyl, 1, 3 -dioxolan-2 -yl, 3,4,5, 6-tetrahydropyridin-2- yl, 4H-1, 3 -thiazin-2 -yl, 4H-3, l-benzothiazin-2-yl, 1, l-dioxo-2, 3,4, 5 - tetrahydrothien-2 -yl, 2H-1, 4-benzothiazin-3-yl, 2H-1,4-benzoxazin-3-yl, 1,3-dihydro-oxazin-2-yl, 1,3-dithiane-2-yl;
Aryl bzw. Aryloxy, Arylthio, Arylcarbonyl und Arylsulfonyl : aromatische mono- oder polycyclische Kohlenwasserstoffreste welche direkt bzw. (Aryloxy) über ein Sauerstoffatom (-0-) oder (Arylthio) ein Schwefelatom (-S-), (Arylcarbonyl) über eine Carbonylgruppe (-CO-) oder (Arylsulfonyl) über eine Sulfonyl- gruppe (-SO2-) an das Gerüst gebunden sind, z.B. Phenyl, Naphthyl und Phenanthrenyl bzw. Phenyloxy, Naphthyloxy und Phenanthrenyl - oxy und die entsprechenden Carbonyl- und Sulfonylreste;Aryl or aryloxy, arylthio, arylcarbonyl and arylsulfonyl: aromatic mono- or polycyclic hydrocarbon radicals which directly or (aryloxy) via an oxygen atom (-0-) or (arylthio) a sulfur atom (-S-), (arylcarbonyl) via a carbonyl group (-CO-) or (arylsulfonyl) are bonded to the skeleton via a sulfonyl group (-SO 2 -), for example phenyl, naphthyl and phenanthrenyl or phenyloxy, naphthyloxy and phenanthrenyloxy and the corresponding carbonyl and sulfonyl radicals;
Hetaryl bzw. Hetaryloxy, Hetarylthio, Hetarylcarbonyl und Hetarylsulfonyl : aromatische mono- oder polycyclische Reste welche neben Kohlenstoffringgliedern zusätzlich ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Sauerstoff- oder ein Schwefelatom oder ein Sauerstoff- oder ein Schwefelatom enthalten können und welche direkt bzw. (Hetaryloxy) über ein Sauerstoffatom (-0-) oder (Hetarylthio) ein Schwefelatom (-S-), (Hetarylcarbonyl) über eine Carbonylgruppe (-CO-) oder (Hetarylsulfonyl) über eine Sulfonylgruppe (-S02-) an das Gerüst gebunden sind, z.B.Hetaryl or hetaryloxy, hetarylthio, hetarylcarbonyl and hetarylsulfonyl: aromatic mono- or polycyclic radicals which in addition to carbon ring members additionally one to four Nitrogen atoms or one to three nitrogen atoms and an oxygen or a sulfur atom or an oxygen or a sulfur atom and which directly or (hetaryloxy) via an oxygen atom (-0-) or (hetarylthio) a sulfur atom (-S-), (Hetarylcarbonyl) via a carbonyl group (-CO-) or (hetarylsulfonyl) via a sulfonyl group (-S0 2 -) are bound to the skeleton, for example
5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoff - atome: 5-Ring Heteroarylgruppen, welche neben Kohlenstoff - atomen ein bis drei Stickstoffatome als Ringglieder enthalten können, z.B. 2-Pyrrolyl, 3-Pyrrolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-Imidazolyl, 4-Imidazolyl, 1, 2, 4-Triazol-3-yl und 1, 3 , 4-Triazol-2-yl;5-membered heteroaryl containing one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three nitrogen atoms as ring members, e.g. 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-triazol-3-yl and 1, 3, 4-triazol-2- yl;
5-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoff - atome oder ein bis drei Stickstoffatome und ein Schwefeloder Sauerstoffatom oder ein Sauerstoff oder ein Schwefel - atom: 5-Ring Heteroarylgruppen, welche neben Kohlenstoff - atomen ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff- oder Schwefelatom als Ringglieder enthalten können, z.B. 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, 2-Pyrrolyl, 3-Pyrrolyl, 3-Isoxazolyl , 4-Isoxazolyl , 5-Isoxazolyl, 3-Isothiazolyl , 4-Isothiazolyl , 5-Isothiazolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-Oxazolyl, 4-Oxazolyl, 5-Oxazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazolyl, 2-Imidazolyl , 4-Imidazolyl , 1 , 2 , 4-OxadiazoI- 3-yl, 1,2, 4-Oxadiazol-5-yl, 1 , 2 , 4-Thiadiazol-3-yl , 1, 2, 4-Thiadiazol-5-yl, 1 , 2 , 4-Triazol-3-yl,5-membered heteroaryl, containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen or one sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and may contain a sulfur or oxygen atom or an oxygen or sulfur atom as ring members, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3- Pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1, 2, 4-oxadiazo I- 3-yl, 1,2, 4-oxadiazol-5-yl, 1, 2, 4-thiadiazol-3-yl, 1, 2, 4-thiadiazol-5-yl, 1, 2, 4-triazol-3- yl,
1,3, 4-Oxadiazol-2-yl, 1,3, 4-Thiddiazoi-2-yI , 1, 3, 4-Triazol-2-yl;1,3,4-oxadiazol-2-yl, 1,3,4-thiddiazoi-2-yl, 1,3,4-triazol-2-yl;
benzokondensiertes 5-gliedriges Heteroaryl, enthaltend ein bis drei Stickstoffatome oder ein Stickstoffatom und/oder ein Sauerstoff- oder Schwefelatom: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome oder ein bis drei Stickstoffatome und ein Schwefel- oder Sauerstoffatom oder ein Sauerstoff- oder ein Schwefelatom als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlenstoffringglieder oder ein Stickstoff- und ein benachbartes Kohlenstoffringglied durch eine Buta-1, 3-dien- 1, 4-diylgruppe verbrückt sein können;Benzo-fused 5-membered heteroaryl, containing one to three nitrogen atoms or one nitrogen atom and / or one oxygen or sulfur atom: 5-ring heteroaryl groups which, in addition to carbon atoms, contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom or one oxygen atom. or may contain a sulfur atom as ring members, and in which two adjacent carbon ring members or a nitrogen and an adjacent carbon ring member may be bridged by a buta-1, 3-diene-1, 4-diyl group;
- über Stickstoff gebundenes 5-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoffatome, oder über Stickstoff gebundenes benzokondensiertes 5-giiedriges Heteroaryl, ent- haltend ein bis drei Stickstoffatome: 5-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis vier Stickstoffatome bzw. ein bis drei Stickstoffatome als Ringglieder enthalten können, und in welchen zwei benachbarte Kohlen- stoffringglieder oder ein Stickstoff- und ein benachbartes5-membered heteroaryl bound via nitrogen, containing one to four nitrogen atoms, or benzo-condensed 5-membered heteroaryl bound via nitrogen, holding one to three nitrogen atoms: 5-ring heteroaryl groups which, in addition to carbon atoms, may contain one to four nitrogen atoms or one to three nitrogen atoms as ring members, and in which two adjacent carbon ring members or one nitrogen and one adjacent one
Kohlenstoffringglied durch eine Buta-1, 3-dien- 1 , 4-diylgruppe verbruckt sein können, wobei diese Ringe über eines der Stickstoffringglieder an das Ger st gebunden sind;Carbon ring member can be bridged by a buta-1, 3-diene-1, 4-diyl group, these rings being bonded to the device via one of the nitrogen ring members;
- 6-gliedriges Heteroaryl, enthaltend ein bis drei bzw. ein bis vier Stickstoffatome : 6-Ring Heteroarylgruppen, welche neben Kohlenstoffatomen ein bis drei bzw. ein bis vier Stickstoff - atome als Ringglieder enthalten können, z.B. 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 3-Pyridazinyl , 4-Pyridazinyl , 2-Pyrimidinyl, 4-Pyrimidinyl, 5-Pyrimidinyl, 2-Pyrazinyl, 1, 3, 5-Triazin-2-yl, 1, 2 , 4-Triazin-3-yl und 1,2,4, 5-Tetrazin-3 -yl;6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-ring heteroaryl groups which, in addition to carbon atoms, can contain one to three or one to four nitrogen atoms as ring members, e.g. 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1, 3, 5-triazin-2-yl, 1, 2, 4-triazin-3-yl and 1,2,4, 5-tetrazin-3 -yl;
benzokondensiertes 6-gliedriges Heteroaryl, enthaltend ein bis vier Stickstoffatome : 6 -Ring Heteroarylgruppen in welchen zwei benachbarte Kohlenstoffringglieder durch eine Buta-1 , 3 -dien- 1, 4 -diylgruppe verbrückt sein können, z.B. Chinolin, Isochinolin, Chinazolin und Chinoxalin,benzo-fused 6-membered heteroaryl containing one to four nitrogen atoms: 6-ring heteroaryl groups in which two adjacent carbon ring members can be bridged by a buta-1, 3 -diene-1, 4 -diyl group, e.g. Quinoline, isoquinoline, quinazoline and quinoxaline,
bzw. die entsprechenden Oxy-, Thio-, Carbonyl- oder Sulfonyl - gruppen.or the corresponding oxy, thio, carbonyl or sulfonyl groups.
Hetarylamino : aromatische mono- oder polycyclische Reste, welche neben Kohlenstoffringgliedern zusätzlich ein bis vier Stickstoff - atome oder ein bis drei Stickstoffatome und ein Sauerstoff- oder ein Schwefeiatom enthalten können und welche über ein Stickstoff - atom an das Gerüst gebunden sind.Hetarylamino: aromatic mono- or polycyclic radicals which, in addition to carbon ring members, can additionally contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom and which are bonded to the structure via a nitrogen atom.
Die Angabe "partiell oder vollständig halogeniert" soll zum Aus- druck bringen, daß in den derart charakterisierten Gruppen die Wasserstoffatome zum Teil oder vollständig durch gleiche oder verschiedene Halogenatome wie vorstehend genannt ersetzt sein können .The expression “partially or fully halogenated” is intended to express that the hydrogen atoms in the groups characterized in this way can be replaced in part or in full by the same or different halogen atoms as mentioned above.
Im Hinblick auf ihre biologische Wirkung sind Verbindungen der Formel I bevorzugt, in denen m für 0 steht.With regard to their biological action, preference is given to compounds of the formula I in which m is 0.
Gleichermaßen bevorzugt sind Verbindungen der Formel I, in denen R1 für Methyl steht. Daneben werden Verbindungen I bevorzugt, in denen R3 für Wasserstoff, Cyano, Cyclopropyl, Methyl, Ethyl, 1 -Methylethyl oder CF3 steht.Likewise preferred are compounds of formula I in which R 1 is methyl. In addition, compounds I are preferred in which R 3 represents hydrogen, cyano, cyclopropyl, methyl, ethyl, 1-methylethyl or CF 3 .
Außerdem werden Verbindungen I bevorzugt, in denen R3 für Methyl steht.In addition, compounds I are preferred in which R 3 is methyl.
Daneben werden Verbindungen I bevorzugt, in denen R3 für Cyano steht.In addition, compounds I are preferred in which R 3 is cyano.
Weiterhin werden Verbindungen I bevorzugt, in denen R3 für Cyclopropyl steht.Furthermore, compounds I are preferred in which R 3 is cyclopropyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R3 für CF3 steht.Furthermore, compounds I are preferred in which R 3 is CF 3 .
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für Wasserstoff, Cyclopropyl, Methyl, Ethyl, iso- Propyl, ggf. subst. Aryl oder Hetaryl steht.Furthermore, compounds I are preferred in which R 5 is hydrogen, cyclopropyl, methyl, ethyl, isopropyl, optionally subst. Aryl or hetaryl is.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Methyl steht.In addition, compounds I are preferred in which R 5 is methyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für Ethyl steht.Furthermore, compounds I are preferred in which R 5 is ethyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Iso- Propyl steht.In addition, compounds I are preferred in which R 5 is isopropyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Cyclopropyl steht.In addition, compounds I are preferred in which R 5 is cyclopropyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für CF3 steht.In addition, compounds I are preferred in which R 5 is CF 3 .
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Aryl oder Hetaryl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Aryl or hetaryl is.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Pyridyl, Pyrimidyl, Pyrazinyl, Pyridazinyl oder Triazinyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Pyridyl, pyrimidyl, pyrazinyl, pyridazinyl or triazinyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Furyl, Thienyl oder Pyrrolyl steht. Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Oxazolyl, Thiazolyl, Isoxazolyl, Isothiazolyl, Pyrazolyl oder Imidazolyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Furyl, thienyl or pyrrolyl. Furthermore, compounds I are preferred in which R 5 for optionally subst. Oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, pyrazolyl or imidazolyl.
Des weiteren werden Verbindungen I bevorzugt, in denen R5 für ggf. subst. Oxdiazolyl, Thiadiazolyl oder Triazolyl steht.Furthermore, compounds I are preferred in which R 5 for optionally subst. Oxdiazolyl, thiadiazolyl or triazolyl.
Außerdem werden Verbindungen I bevorzugt, in denen R5 für Phenyl steht, welches unsubstituiert ist oder ein oder zwei der folgen- den Gruppen trägt: Nitro, Cyano, Hydroxy, Amino, Aminocarbonyl, Aminothiocarbonyl, Halogen, Cχ-C -Alkyl, Cι-C -Halogenalkyl, Cι-C -Alkoxy, Cχ-C-Halogenalkoxy, C1-C -Alkylamino, Di-Cι-C - Alkylamino, C1-C -Alkylsulfonyl, Cι-C -Alkoxycarbonyl , Cχ-C -Alkyl- aminocarbonyl oder Di-Cι-C-Alkylaminocarbonyl .In addition, compounds I are preferred in which R 5 is phenyl which is unsubstituted or carries one or two of the following groups: nitro, cyano, hydroxy, amino, aminocarbonyl, aminothiocarbonyl, halogen, Cχ-C -alkyl, Cι- C -haloalkyl, -C-C alkoxy, Cχ-C-haloalkoxy, C 1 -C -alkylamino, di-Cι-C - alkylamino, C 1 -C -alkylsulfonyl, Cι-C -alkoxycarbonyl, Cχ-C -alkyl- aminocarbonyl or Di-Cι-C-alkylaminocarbonyl.
Außerdem werden Verbindungen I bevorzugt, in denen R4 für Wasserstoff, Cι-C6-Alkyl, C2-C6-Alkenyl, C2-C6 -Alkinyl , Allyl, Arylalkyl, Hetarylalkyl , Aryloxyalkyl , Hetaryloxyalkyl , Aryl oder Hetaryl steht.In addition, compounds I are preferred in which R 4 represents hydrogen, -CC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, allyl, arylalkyl, hetarylalkyl, aryloxyalkyl, hetaryloxyalkyl, aryl or hetaryl .
Des weiteren werden Verbindungen I bevorzugt, in denen R4 für Cι-C6-Alkyl steht.Furthermore, compounds I are preferred in which R 4 is C 1 -C 6 -alkyl.
Weitere bevorzugte Verbindungen I sind der WO 97/15,552 zu ent- nehmen.Further preferred compounds I can be found in WO 97 / 15,552.
Die in den erfindungsgemäßen Mischungen enthaltenen Verbindungen I zeichnen sich durch eine hervorragende Wirkung gegen ein breites Spektrum von pflanzenpathogenen Pilzen, insbesondere gegen Pilze aus den Klassen der Ascomyceten, Deuteromyceten, Phycomyce- ten und Basidiomyceten.The compounds I contained in the mixtures according to the invention are distinguished by an outstanding action against a broad spectrum of phytopathogenic fungi, in particular against fungi from the classes of the Ascomycetes, Deuteromycetes, Phycomycetes and Basidiomycetes.
Besondere Bedeutung haben sie für die Bekämpfung einer Vielzahl von Pilzen an verschiedenen Kulturpflanzen wie Baumwolle, Gemüse- pflanzen (z.B. Gurken, Bohnen, Tomaten, Kartoffeln und Kürbisgewächse), Gerste, Gras, Hafer, Bananen, Kaffee, Mais, Obstpflanzen, Reis, Roggen, Soja, Wein, Weizen, Zierpflanzen, Zuckerrohr sowie an einer Vielzahl von Samen.They are of particular importance for combating a large number of fungi on various crops such as cotton, vegetable plants (eg cucumber, beans, tomatoes, potatoes and squashes), barley, grass, oats, bananas, coffee, corn, fruit plants, rice, rye , Soy, wine, wheat, ornamental plants, sugar cane and a variety of seeds.
Insbesondere eignen sie sich zur Bekämpfung der folgenden pf lanzenpathogenen Pilze: Erysiphe graminis (echter Mehltau) an Getreide, Erysiphe cichoracearum und Sphaerotheca fuliginea an Kürbisgewächsen, Podosphaera leucotricha an Äpfeln, Uncinula necator an Reben, Puccinia-Arten an Getreide, Rhizoctonia-Arten an Baumwolle, Reis und Rasen, Ustilago-Arten an Getreide und Zuk- kerrohr, Venturia inaequalis (Schorf) an Äpfeln, Helminthospori- um-Arten an Getreide und Reis, Septoria nodorum an Weizen, Botrytis cinera (Grauschimmel) an Erdbeeren, Gemüse, Zierpflanzen und Reben, Cercospora arachidicola an Erdnüssen, Pseudo- cercosporella herpotrichoides an Weizen und Gerste, Pyricularia oryzae an Reis und Rasen, Phytophthora infestans an Kartoffeln und Tomaten, Plasmopara viticola an Reben, Pseudoperonospora-Ar- ten in Hopfen und Gurken, Alternaria-Arten an Gemüse und Obst, Mycosphaerella-Arten in Bananen sowie Fusarium- und Verticillium- Ar en.They are particularly suitable for combating the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia cotton species on cereal species, Rhiz , Rice and lawn, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, Helminthosporium species on cereals and rice, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries, vegetables, ornamental plants and vines, Cercospora arachidicola on peanuts, Pseudo-cercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice and lawn, Phytophthora infestans on potatoes and tomatoes, Plasmopara viticola on vines, pseudoperon - ten in hops and cucumbers, Alternaria species in vegetables and fruits, Mycosphaerella species in bananas and Fusarium and Verticillium species.
Die Verbindungen der Formeln II bis IX werden zur Bekämpfung von tierischen Schädlingen aus der Klasse der Insekten, Spinnentiere und Nematoden eingesetzt. Sie können im Pflanzenschutz sowie auf dem Hygiene-, Vorratsschutz- und Veterinärsektor zur Bekämpfung tierischer Schädlinge eingesetzt werden. Insbesondere eignen sie sich zur Bekämpfung der folgenden tierischen Schädlinge:The compounds of the formulas II to IX are used to control animal pests from the class of the insects, arachnids and nematodes. They can be used in crop protection as well as in the hygiene, storage protection and veterinary sectors to control animal pests. They are particularly suitable for controlling the following animal pests:
• Insekten aus der Ordnung der Schmetterlinge (Lepidoptera) beispielsweise Agrotis ypsilon, Agrotis segetum, Alabama argilla- cea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insu- lana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersi- cella, Lambdina fiscellaria, Laphygma exigua, Leucoptera cof - feella, Leucoptera sciteila, Lithocolletis blancardella, Lobe- sia botrana, Loxostege sticticalis, Lymuntrid dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella,• Insects from the order of the butterflies (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argilla- cea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobone brumoneurumuraisumuraisumuraisumanaurumura, chorus unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Helithiothiothiothiella, Helithiothiothiothi, Helithium, Helithiothiothiothiothi, Helithiothiothiothi, Helithiothiothiothi, Helithiothiothiothiothi, Helithiothiothiothi, Helithiothiothi, Helithiothiothiothi, Helithiothiothiothi, Helithiothiothi undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersi- cella, Lambdina fiscellaria, Laphygma exigua, Leucoptera cof - feella, Leucoptera sciteila, Lithocolletis blancardella, Lobe- sia botrana, Licalidia triaxia triaxia triaxia, loxidia paria, Loxidia paria, Loxidia moniaxia triaxia, loxidia paria, Loxidia moniaxia triaxia Malacosoma neustria, Mamest ra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella,
Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseu- doplusia includens, Rhyacionia frustrana, Scrobipalpula abso- luta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumato- poea pityocampa, Tortrix viridana, Trichoplusia ni und Zeira- phera canadensis,Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens, Rhyacionia frustrana, Scrobipalpula abso- luta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Trumocampidia nia, Thaumocampia- nia, Thaumocampia- poira phera canadensis,
• Käfer (Coleoptera) , z.B. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Bla- stophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bru- chus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebu- losa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorr- hynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc- tata, Diabrotica virgifera, Epilachna varivestis, Epitrix hir- tipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californi- cus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani , Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllotreta chrysocephala, Phyllophaga sp., Phyl - lopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus und Sitophilus granaria,• Beetles (Coleoptera), e.g. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bru, Bruchus pis Byctiscus betulae, Cassida nebu- losa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc- tata, Diabrotica virgifera, Epilachna varivestis, Epitrix hir- tipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus commander, Meligethes aeneus, Melolonhynus, Melolontha melolonus chrysocephala, Phyllophaga sp., Phyl - lopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria,
• Zweiflügler (Diptera), z.B. Aedes aegypti, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macella- ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi- piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fan- nia canicularis, Gasterophilus intestinalis, Glossina morsi- tans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifo- lii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lyco- ria pectoralis, Mayetiola destructor, Musca domestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami,• Two-winged (Diptera), e.g. Aedes aegypti, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macella- ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, fan- nia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata pectoral, Lyco- rica pomica, lyco- rica, lorica- rica, lalica- rorica p , Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami,
Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagole- tis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula ole- racea und Tipula paludosa,Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula ole-racea and Tipula paludosa,
• Thripse (Thysanoptera) , z.B. Frankliniella fusca, Frankiiniella occidentalis, Franklinielia tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi und Thrips tabaci,Thrips (Thysanoptera), e.g. Frankliniella fusca, Frankiiniella occidentalis, Franklinielia tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
• Hautflügler (Hymenoptera) , z.B. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testu- dinea, Monomorium pharaonis, Solenopsis geminata und Solenopsis invicta,Dermatoptera (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,
• Wanzen (Heteroptera), z.B. Acrosternum hilare, Blissus leucop- terus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus in- termedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Ne- zara viridula, Piesma quadrata, Solubea insularis und Thyanta perditor,Bugs (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara quadrantulais, Pyanma viridula, Pies
Pflanzensauger (Homoptera) , z.B. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi , Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce- rosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopa- lomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sap- paphis mali, Schizaphis graminum, Schizoneura lanuginosa, Tria- leurodes vaporariorum und Viteus vitifolii,Plant suckers (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce-rosipha gossypii, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae, Macrosiphum avenae, Macrosiaodumeodona Maconia phiumisodumophone, Macrosia diaumodis, Macrosia diumusumica, Macrosia diodiahumacophus, Macrosia diumusi Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Sappaphis mala, Sap- paphis mali, Schizaphis graminum, Viz.
• Termiten (Isoptera) , z.B. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus und Termes natalensis,Termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis,
• Geradflügler (Orthoptera), z.B. Acheta domestica, Blatta orien- talis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melano- plus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguini - pes, Melanoplus spretus, Nomadacris septemfasciata, Periplaneta americana, Schistocerca americana, Schistocerca peregrina, Stauronotus maroccanus und Tachycines asynamorus,Straight wing aircraft (Orthoptera), e.g. Acheta domestica, Blatta orien- talis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melano- plus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguini-pes, Melanoplus spretus, Schomannacana america, Nomadascocata americana Schistocerca peregrina, Stauronotus maroccanus and Tachycines asynamorus,
• Arachnoidea wie Spinnentiere (Acarina), z.B. Amblyomma america- num, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoeni - eis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubieundus, Ornithodorus moubata, Otobius me- gnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllo- coptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetra - nychus paeificus, Tetranychus telarius und Tetranychus urticae,Arachnoid such as arachnids (Acarina), e.g. Amblyomma america- num, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpus phoeni-eis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalundxnobinium, Hyalommxxusodusunc me- gnini, Paratetranychus pilosus, Dermanyssus gallinae, Phyllo- coptruta oleivora, Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabieus, Tetranychus Tinnabarinus tawchychanyus, Tetranychany Tawchanyus, Tetranych
• Nematoden wie Wurzelgallennematoden, z.B. Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, Zysten bildende Nematoden, z.B. Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, Stock- und Blattälchen, z.B. Belonolaimus longicaudatus, Dity- lenchus destruetor, Ditylenchus dipsaci, Heliocotylenchus mul- ticinetus, Longidorus elongatus, Radopholus similis, Rotylen- chus robustus, Trichodorus primitivus, Tylenchorhynchus clay- toni, Tylenchorhynchus dubius, Pratylenchus neglectus, Praty- lenchus penetrans, Pratylenchus curvitatus und Pratylenchus goodeyi . Die Aufwandmenge an Wirkstoff zur Bekämpfung von tierischen Schädlingen beträgt unter Freilandbedingungen in der Regel 0,01 bis 2,0, vorzugsweise 0,02 bis 1,0 kg/ha.• Nematodes such as root-bile nematodes, eg Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming nematodes, eg Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolius, longica- lodum, undelongeluityu, stock- and leafelenchia dipsaci, Heliocotylenchus mul- ticinetus, Longidorus elongatus, Radopholus similis, Rotylen- chus robustus, Trichodorus primitivus, Tylenchorhynchus clay- toni, Tylenchorhynchus dubius, Pratylenchus neglectus, Praty- lenchusususatati curatusi, Praty- lenchususususatatiatusi, Praty- lusus penetraty curatus, Praty- lenchusususususatati curatusi, Praty- lenchusususususatati curatusi, Praty- lenchusususususatati curatus, Praty- undususususatansi. The amount of active ingredient used to control animal pests is generally from 0.01 to 2.0, preferably from 0.02 to 1.0, kg / ha under field conditions.
Besonders bevorzugt sind die erfindungsgemäßen Mischungen zur Bekämpfung von Pflanzenkrankheiten und Schadinsekten in Reis einsetzbar.The mixtures according to the invention can particularly preferably be used to control plant diseases and insect pests in rice.
Die Verbindungen I und mindestens eine der Verbindungen II bis XI können gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander aufgebracht werden, wobei die Reihenfolge bei getrennter Applikation im allgemeinen keine Auswirkung auf den Bekämpfungs- erfolg hat.The compounds I and at least one of the compounds II to XI can be applied simultaneously, that is jointly or separately, or in succession, the sequence in the case of separate application generally not having any effect on the control success.
Die Aufwandmengen der erfindungsgemäßen Mischungen liegen, vor allem bei landwirtschaftlichen Kulturflächen, je nach Art des gewünschten Effekts bei 0,01 bis 8 kg/ha, vorzugsweise 0,1 bis 5_kg/ha, insbesondere 0,5 bis 3,0 kg/ha.The application rates of the mixtures according to the invention, especially for agricultural crop areas, are from 0.01 to 8 kg / ha, preferably 0.1 to 5 kg / ha, in particular 0.5 to 3.0 kg / ha, depending on the type of effect desired.
Die Aufwandmengen liegen dabei für die Verbindungen I bei 0,01 bis 2,5 kg/ha, vorzugsweise 0,05 bis 2,5 kg/ha, insbesondere 0,1 bis 1,0 kg/ha.The application rates for the compounds I are 0.01 to 2.5 kg / ha, preferably 0.05 to 2.5 kg / ha, in particular 0.1 to 1.0 kg / ha.
Bei der Saatgutbehandlung werden im allgemeinen Aufwandmengen an Mischung von 0,001 bis 250 g/kg Saatgut, vorzugsweise 0,01 bis 100 g/kg, insbesondere 0,01 bis 50 g/kg verwendet.In the case of seed treatment, application rates of mixture of 0.001 to 250 g / kg of seed, preferably 0.01 to 100 g / kg, in particular 0.01 to 50 g / kg, are generally used.
Sofern für Pflanzen pathogene Schadpilze zu bekämpfen sind, erfolgt die getrennte oder gemeinsame Applikation der Verbindungen I und mindestens einer der Verbindungen II bis XI oder derIf pathogenic fungi are to be combated for plants, the separate or joint application of the compounds I and at least one of the compounds II to XI or
Mischungen aus den Verbindungen I und mindestens einer der Verbindungen II bis IX durch Besprühen oder Bestäuben der Samen, der Pflanzen oder der Böden vor oder nach der Aussaat der Pflanzen oder vor oder nach dem Auflaufen der Pflanzen.Mixtures of the compounds I and at least one of the compounds II to IX by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.
Die erfindungsgemäßen Mischungen können beispielsweise in Form von direkt versprühbaren Lösungen, Pulver und Suspensionen oder in Form von hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen, Dispersionen, Emulsionen, Öldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten aufbereitet und durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsform ist abhängig vom Verwendungszweck; sie soll in jedem Fall eine möglichst feine und gleichmäßige Verteilung der erfindungsgemäßen Mischung gewährleisten. Die Formulierungen werden in bekannter Weise hergestellt, z.B. durch Verstrecken des Wirkstoffs mit Lösungsmitteln und/oder Trägerstoffen, gewünschtenfalls unter Verwendung von Emulgiermitteln und Dispergiermitteln, wobei im Falle von Wasser als Verdύnnungs- mittel auch andere organische Lösungsmittel als Hilfslόsungsmit- tel verwendet werden können. Als Hilfsstoffe kommen dafür im wesentlichen in Betracht: Losungsmittel wie Aromaten (z.B. Xylol) , chlorierte Aromaten (z.B. Chlorbenzole), Paraffine (z.B. Erdöl - fraktionen) , Alkohole (z.B. Methanol, Butanol) , Ketone (z.B. Cyclohexanon) , Amine (z.B. Ethanolamin, Dimethylformamid) und Wasser; Trägerstoffe wie naturliche Gesteinsmehle (z.B. Kaoline, Tonerden, Talkum, Kreide) und synthetische Gesteinsmehle (z.B. hochdisperse Kieselsäure, Silikate) ; Emulgiermittel wie nichtio- nogene und anionische Emulgatoren (z.B. Polyoxyethylen-Fettalko- hol-Ether, Alkylsulfonate und Arylsulfonate) und Dispergiermittel wie Ligninsulfitablaugen und Methylcellulose.The mixtures according to the invention can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-strength aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules and by spraying, atomizing, dusting, scattering or pouring can be applied. The form of application depends on the intended use; in any case, it should ensure that the mixture according to the invention is as fine and uniform as possible. The formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants, and in the case of water as diluent, other organic solvents can also be used as auxiliary solvents. The following are essentially considered as auxiliaries: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. ethanolamine , Dimethylformamide) and water; Carriers such as natural stone powder (eg kaolins, clays, talc, chalk) and synthetic stone powder (eg highly disperse silica, silicates); Emulsifiers such as non-ionic and anionic emulsifiers (eg polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin sulfite waste liquors and methyl cellulose.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie vonThe alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as from
Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanole oder Fettalkoholglycolethern, Kondensationsprodukte von sulfoniertem Naphthalin und seinen Derivaten mit Form- aldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxyethylenoctyl - phenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenol- oder Tributylphenylpolyglycolether, Alkylarylpoly- etheralkohole, Isotridecylalkohol, Fettalkoholethylenoxid- Kon- densate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether oder Poiyoxypropylen, Laurylalkoholpolyglycoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.Fatty acids, alkyl and alkyl aryl sulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalene and phenol and sulfonic acids with phenol formaldehyde, Polyoxyethylenoctyl - Phenol, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol or Tributylphenylpolyglycolether, alkylaryl polyglycol ether-isotridecylalcohol, Fettalkoholethylenoxid- con- condensates, ethoxylated castor oil, polyoxyethylene or Poiyoxypropylen, Laurylalkoholpolyglycoletheracetat, sorbitol esters, lignin-sulfite waste liquors or methylcellulose .
Pulver Streu- und Stäubemittel können durch Mischen oder gemein- sames Vermählen der Verbindungen I und mindestens einer der Verbindungen II bis XI oder der Mischung aus den Verbindungen I und mindestens einer der Verbindungen II bis XI mit einem festen Trägerstoff hergestellt werden.Powder sprinklers and dusts can be prepared by mixing or jointly grinding the compounds I and at least one of the compounds II to XI or the mixture of the compounds I and at least one of the compounds II to XI with a solid carrier.
Granulate (z.B. Umhullungs-, Imprägnierungs- oder Homogengranulate) werden üblicherweise durch Bindung des Wirkstoffs oder der Wirkstoffe an einen festen Trägerstoff hergestellt.Granules (e.g. coated granules, impregnated granules or homogeneous granules) are usually produced by binding the active ingredient or ingredients to a solid carrier.
Als Füllstoffe bzw. feste Trägerstoffe dienen beispielsweise Mineralerden wie Silicagel, Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Caicium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, sowie Düngemittel wie Ammoniumsulfat, Ammoniumphosphat , Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Mineral earths such as silica gel, silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, boluses, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, serve, for example, as fillers or solid carriers. ground plastics, as well as fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Die Formulierungen enthalten im allgemeinen 0,1 bis 95 Gew.-%, vorzugsweise 0,5 bis 90 Gew.-% einer der Verbindungen I und mindestens einer der Verbindungen II bis XI bzw. der Mischung aus den Verbindungen I und mindestens einer der Verbindungen II bis XI. Die Wirkstoffe werden dabei in einer Reinheit von 90 % bis 100%, vorzugsweise 95 % bis 100 % (nach NMR- oder HPLC-Spektrum) eingesetzt .The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight, of one of the compounds I and at least one of the compounds II to XI or the mixture of the compounds I and at least one of the compounds II to XI. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR or HPLC spectrum).
Die Anwendung der Verbindungen I und mindestens einer der Verbin- dungeή II bis XI, der Mischungen oder der entsprechenden Formulierungen erfolgt so, daß man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit einer fungizid wirksamen Menge der Mischung, bzw. der Verbindungen I und mindestens einer der Verbindungen II bis XI bei getrennter Ausbringung, behandelt.The use of the compounds I and at least one of the compounds II to XI, the mixtures or the corresponding formulations takes place in such a way that the harmful fungi, their habitat or the plants, seeds, soils, surfaces, materials or spaces to be kept free of them with a fungicidally effective amount of the mixture, or of the compounds I and at least one of the compounds II to XI treated separately.
Die Anwendung kann vor oder nach dem Befall durch die Schadpilze erfolgen.The application can take place before or after the infestation by the harmful fungi.
Beispiele für solche Zubereitungen, welche die Wirkstoffe enthalten, sind:Examples of such preparations that contain the active ingredients are:
I. eine Lösung aus 90 Gew. -Teilen der Wirkstoffe und 10 Gew.- Teilen N-Methylpyrrolidon, die zur Anwendung in Form klein- ster Tropfen geeignet ist;I. a solution of 90 parts by weight of the active ingredients and 10 parts by weight of N-methylpyrrolidone, which is suitable for use in the form of tiny drops;
II. eine Mischung aus 20 Gew. -Teilen der Wirkstoffe, 80 Gew.- Teilen Xylol, 10 Gew. -Teilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N-monoethanolamid,II. A mixture of 20 parts by weight of the active ingredients, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide,
5 Gew. -Teilen Calciumsalz der Dodecylbenzolsulfonsäure, 5 Gew. -Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl; durch feines Verteilen der Lösung in Wasser erhält man eine Dispersion;5 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 5 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil; a dispersion is obtained by finely distributing the solution in water;
III. eine wäßrige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 40 Gew. -Teilen Cyclohexanon, 30 Gew. -Teilen Isobutanol, 20 Gew. -Teilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl ,-III. an aqueous dispersion of 20 parts by weight of the active ingredients, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil,
IV. eine wäßrige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 25 Gew. -Teilen Cyclohexanol , 65 Gew. -Teilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gew.-Tei- len des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl; V. eine in einer Hammermühle vermahlene Mischung aus 80 Gew.- Teilen der Wirkstoffe, 3 Gew. -Teilen des Natriumsalzes der Diisobutylnaphthalin-1-sulfonsäure, 10 Gew. -Teilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfitablauge und 7 Gew. -Teilen pulverförmigem Kieselsäuregel; durch feines Verteilen der Mischung in Wasser erhält man eine Spritzbrühe;IV. An aqueous dispersion of 20 parts by weight of the active ingredients, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide 1 mole of castor oil; V. a mixture of 80 parts by weight of the active ingredients, 3 parts by weight of the sodium salt of diisobutylnaphthalene-1-sulfonic acid, 10 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powder Silica gel; a spray mixture is obtained by finely distributing the mixture in water;
VI. eine innige Mischung aus 3 Gew. -Teilen der Wirkstoffe und 97 Gew. -Teilen feinteiligem Kaolin; dieses Stäubemittel enthält 3 Gew.-% Wirkstoff;VI. an intimate mixture of 3 parts by weight of the active ingredients and 97 parts by weight of finely divided kaolin; this dust contains 3% by weight of active ingredient;
VII. eine innige Mischung aus 30 Gew. -Teilen der Wirkstoffe, 92 Gew. -Teilen pulverförmigem Kieselsäuregel und 8 Gew. -Teilen Paraffinöl, das auf die Oberfläche dieses Kieselsäuregels gesprüht wurde; diese Aufbereitung gibt dem Wirkstoff eine gute Haftfähigkeit;VII. An intimate mixture of 30 parts by weight of the active ingredients, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil which has been sprayed onto the surface of this silica gel; this preparation gives the active ingredient good adhesion;
VIII. eine stabile wäßrige Dispersion aus 40 Gew. -Teilen der Wirkstoffe, 10 Gew. -Teilen des Natriumsalzes eines Phenolsulfonsäure-Harnstoff-Formaldehyd-Kondensates, 2 Gew. -Teilen Kieselgel und 48 Gew. -Teilen Wasser, die weiter ver- dünnt werden kann;VIII. A stable aqueous dispersion of 40 parts by weight of the active ingredients, 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which further dilutes can be;
IX. eine stabile ölige Dispersion aus 20 Gew. -Teilen der Wirkstoffe, 2 Gew. -Teilen des Calciumsalzes der Dodecylbenzol - sulfonsäure, 8 Gew. -Teilen Fettalkohol-polyglykolether,IX. a stable oily dispersion of 20 parts by weight of the active ingredients, 2 parts by weight of the calcium salt of dodecylbenzene sulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether,
20 Gew. -Teilen des Natriumsalzes eines Phenolsulfonsäure- Harnstoff-Formaldehydkondensates und 88 Gew. -Teilen eines paraffinischen Mineralöls.20 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 88 parts by weight of a paraffinic mineral oil.
Die synergistische Wirkung der erfindungsgemäßen Mischungen läßt sich durch die folgenden Versuche zeigen:The synergistic effect of the mixtures according to the invention can be demonstrated by the following experiments:
Die Wirkstoffe werden getrennt oder gemeinsam als 10 %ige Emulsion in einem Gemisch aus 63 Gew.-% Cyclohexanon und 27 Gew.-% Emulgator aufbereitet und entsprechend der gewünschten Konzentration mit Wasser verdünnt.The active ingredients are prepared separately or together as a 10% emulsion in a mixture of 63% by weight cyclohexanone and 27% by weight emulsifier and diluted with water in accordance with the desired concentration.
Die Auswertung erfolgt durch Feststellung der befallenen Blattflächen in Prozent. Diese Prozent-Werte werden in Wirkungsgrade umgerechnet. Der Wirkungsgrad (W) wird nach der Formel von Abbot wie folgt bestimmt:The evaluation is carried out by determining the affected leaf areas in percent. These percentages are converted into efficiencies. Efficiency (W) is determined using Abbot's formula as follows:
= (1 - α) -100/ß= (1 - α) -100 / ß
α entspricht dem Pilzbefall der behandelten Pflanzen in % und ß entspricht dem Pilzbefall der unbehandelten (Kontroll-) Pflanzen in % Bei einem Wirkungsgrad von 0 entspricht der Befall der behandelten Pflanzen demjenigen der unbehandelten Kontrollpflanzen; bei einem Wirkungsgrad von 100 wiesen die behandelten Pflanzen keinen Befall auf.α corresponds to the fungal attack of the treated plants in% and ß corresponds to the fungal attack of the untreated (control) plants in% With an efficiency of 0, the infection of the treated plants corresponds to that of the untreated control plants; at an efficiency of 100, the treated plants showed no infection.
Die zu erwartenden Wirkungsgrade der Wirkstoffmischungen wurden nach der Colby Formel [R.S. Colby, Weeds 15_, 20-22 (1967)] ermittelt und mit den beobachteten Wirkungsgraden verglichen.The expected efficacies of the active ingredient mixtures were calculated using the Colby formula [R.S. Colby, Weeds 15_, 20-22 (1967)] and compared with the observed efficiencies.
Colby Formel: E = x + y - x-y/100Colby formula: E = x + y - x-y / 100
E zu erwartender Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz der Mischung aus den Wirkstoffen A und B in den Konzentrationen a und b x der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs A in der Konzentration a y der Wirkungsgrad, ausgedrückt in % der unbehandelten Kontrolle, beim Einsatz des Wirkstoffs B in der Konzentration bE expected efficiency, expressed in% of the untreated control, when using the mixture of active ingredients A and B in concentrations a and bx the efficiency, expressed in% of the untreated control, when using active ingredient A in concentration ay, the efficiency, expressed in% of the untreated control when using the active ingredient B in the concentration b
Anwendungsbeispiel 1 - Wirksamkeit gegen Pyricularia oryzae (protektiv)Example of use 1 - Activity against Pyricularia oryzae (protective)
Blätter von in Töpfen gewachsenen Reiskeimlingen der Sorte "Tai- Nong 67" wurden mit wäßriger Wirkstoffaufbereitung, die mit einer Stammlösung aus 10 % Wirkstoff, 63 % Cyclohexanon und 27 % Emulgiermittel angesetzt wurde, bis zur Tropfnässe besprüht. Am folgenden Tag wurden die Pflanzen mit einer wäßrigen Sporensuspension von Pyricularia oryzae inokuliert. Anschließend wurden die Versuchspflanzen in Klimakammern bei 22 - 24° C und 95 - 99 % relativer Luftfeuchtigkeit für 6 Tage aufgestellt. Dann wurde das Ausmaß der Befallsentwicklung auf den Blättern visuell ermittelt.Leaves of "Tai-Nong 67" rice seedlings grown in pots were sprayed to runoff point with aqueous active compound preparation which was prepared with a stock solution of 10% active compound, 63% cyclohexanone and 27% emulsifier. The following day, the plants were inoculated with an aqueous spore suspension of Pyricularia oryzae. The test plants were then placed in climatic chambers at 22-24 ° C and 95-99% relative humidity for 6 days. The extent of the development of the infestation on the leaves was then determined visually.
Die visuell ermittelten Werte für den Prozentanteil befallener Blattflächen wurden in Wirkungsgrade als % der unbehandelten Kontrolle umgerechnet. Wirkungsgrad 0 ist gleicher Befall wie in der unbehandelten Kontrolle, Wirkungsgrad 100 ist 0 % Befall. Die zu erwartenden Wirkungsgrade für Wirkstoffko binationen wurden nach der Colby-Formel (Colby, S. R. : "Calculating synergistic and an- tagonistic responses of herbicide Combinations" , Weeds 15., S. 20 - 22, 1967) ermittelt und mit den beobachteten Wirkungsgraden verglichen.The visually determined values for the percentage of leaf areas affected were converted into efficiencies as% of the untreated control. Efficiency 0 is the same as in the untreated control, efficiency 100 is 0%. The combinations expected efficacies for Wirkstoffko were determined using Colby's formula (Colby, SR "Calculating synergistic and Toggle tagonistic responses of herbicide Combinations", Weeds 15, pp 20-22., 1967) and compared with the observed efficacies .
Als Komponente a) wurde folgende Verbindung I' eingesetzt: The following compound I 'was used as component a):
Die Ergebnisse der Versuche sind den nachstehenden Tabellen 1 und 2 zu entnehmen:The results of the tests are shown in Tables 1 and 2 below:
Tabelle 1Table 1
Tabelle 2:Table 2:
*> berechnet nach der Colby-Formel*> calculated according to the Colby formula
Aus den Ergebnissen der Versuche geht hervor, daß der beobachtete Wirkungsgrad in allen Mischungsverhältnissen höher ist als der nach der Colby- Formel vorausberechnete Wirkungsgrad. The results of the experiments show that the observed efficiency in all mixing ratios is higher than the efficiency calculated in advance using the Colby formula.

Claims

Patentansprüche claims
1. Mischungen für den Pflanzenschutz, enthaltend als aktive Komponenten1. Mixtures for crop protection, containing as active components
a) P enylessigsäurederivate der Formel Ia) P enylacetic acid derivatives of the formula I.
in der die Substituenten und der Index die folgende Bedeutung haben:in which the substituents and the index have the following meaning:
X NOCH3, CHOCH3 oder CHCH3 ;X STILL 3 , CHOCH 3 or CHCH 3 ;
Y Sauerstoff oder NR;Y is oxygen or NR;
R!,R unabhängig voneinander Wasserstoff oder C]_-C -Alkyl;R!, R independently of one another are hydrogen or C] _- C -alkyl;
R2 Cyano, Nitro, Trifluormethyl , Halogen, Cι~C -Alkyl oder Cι-C -Alkoxy;R 2 cyano, nitro, trifluoromethyl, halogen, -C ~ alkyl or -C -C alkoxy;
m 0, 1 oder 2, wobei die Reste R2 verschieden sein können, wenn m für 2 steht;m is 0, 1 or 2, it being possible for the radicals R 2 to be different if m is 2;
R3 Wasserstoff, Cyano, C]_-C -Alkyl, Cι-C -Halogenalkyl oder C3-C6-Cycloalkyl;R 3 is hydrogen, cyano, C] _- C alkyl, -C -C haloalkyl or C 3 -C 6 cycloalkyl;
R4,R6 unabhängig voneinander Wasserstoff,R 4 , R 6 are independently hydrogen,
Cι-Cιo-Alkyl, C3-C6-Cycloalkyl, C -Cιo-Alkenyl , C2-Cιo-Alkinyl, Cι-Cιo-Alkylcarbonyl , C2-Cιo-Alkenyl- carbonyl , C3-Cιo-Alkinylcarbonyl oder Cι-Cχo-Alkyl- sulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cβ-Alkyl, Ci-Cß-Halogenalkyl , Ci-Cß-Alkylsulfonyl, Cι-C6-Alkylsulfoxyl , Ci-Cg-Alkoxy,Cι-Cιo-alkyl, C 3 -C 6 cycloalkyl, C -Cιo-alkenyl, C 2 -Cιo-alkynyl, Cι-Cιo-alkylcarbonyl, C 2 -Cιo-alkenylcarbonyl, C 3 -Cιo-alkynylcarbonyl or Cι -Cχo-alkyl-sulfonyl, where these radicals can be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cβ-alkyl, Ci-C ß -haloalkyl, Ci-C ß -alkylsulfonyl, Cι-C 6 -alkylsulfoxyl, Ci-Cg-alkoxy,
Cι-C6-Halogenalkoxy, Cι-C5-Alkoxycarbonyl , Cι-C6-Alkyl- thio, Cι-C6-Alkylamino, Di-Ci-Cg-alkylamino, Ci-Cg-Alkylaminocarbonyl , Di-Ci-Cg-alkylaminocarbonyl , Ci-Cg-Alkylaminothiocarbonyl, Di-Ci-Cg-alkylaminothio- carbonyl, C2-Cg-Alkenyl, C -Cg-Alkenyloxy, C3-Cg-Cyclo- alkyl, C3-C6-Cycloalkyloxy, Heterocyclyl, Hetero- cyclyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio,Cι-C 6 haloalkoxy, Cι-C 5 alkoxycarbonyl, Cι-C 6 -alkylthio, Cι-C6-alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothio-carbonyl, C 2 -Cg-alkenyl, C -Cg-alkenyloxy, C 3 -Cg-cyclo- alkyl, C 3 -C 6 cycloalkyloxy, heterocyclyl, heterocyclicoxy, benzyl, benzyloxy, aryl, aryloxy, arylthio,
Hetaryl, Hetaryloxy und Hetarylthio, wobei die cyclischen Gruppen ihrerseits partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cß-Alkylsulfonyl, Cχ-Cg-Alkylsulfoxyl, C3-Cg-Cyclo- alkyl, Ci-Cg-Alkoxy, Cι-C6-Halogenalkoxy, Ci-Cg-Alkyl- oxycarbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Ci-Cg-Alkylamino, Cχ-Cg-Alkylaminocarbonyl,Hetaryl, hetaryloxy and hetarylthio, where the cyclic groups can in turn be partially or completely halogenated or can carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl , Ci-Cg-haloalkyl, Ci-C ß- alkylsulfonyl, Cχ-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl, Ci-Cg-alkoxy, Cι-C 6 -haloalkoxy, Ci-Cg-alkyloxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, Cχ-Cg-alkylaminocarbonyl,
Di-Ci-Cg-Alkylaminocarbonyl , Ci-Cg-Alkylaminothio- carbonyl, Di-Ci-Cg-Alkylaminothiocarbonyl, C2-Cg- Alkenyl, C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio oder C (=N0R7 ) -An-R8 ;Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C 2 -Cg-alkenyl, C 2 -Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, Hetaryloxy, hetarylthio or C (= NO R 7 ) -A n -R 8 ;
Aryl, Arylcarbonyl, Arylsulfonyl , Hetaryl, Hetaryl - carbonyl oder Hetarylsulfonyl, wobei diese Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können:Aryl, arylcarbonyl, arylsulfonyl, hetaryl, hetarylcarbonyl or hetarylsulfonyl, where these residues can be partially or completely halogenated or can carry one to three of the following groups:
Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cß-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylcarbonyl , Ci-Cg-Alkyl- sulfonyl, Ci-Cg-Alkylsulfoxyl , C3-Cg-Cycloalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkyloxy- carbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Cχ-Cg- Alkylamino, Ci-Cg-Alkylaminocarbonyl , Di-Ci-Cg-Alkyl- aminocarbonyl , Ci-Cg-Alkylaminothiocarbonyl, Di-Ci-Cg- Alkylaminothiocarbonyl, C2-Cg-Alkenyl, C2-Cg-Alkenyl- oxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Hetaryl,Cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-C ß- alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylcarbonyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl , C3-Cg-cycloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkyloxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Cχ-Cg-alkylamino, Ci-Cg -Alkylaminocarbonyl, Di-Ci-Cg-Alkyl- aminocarbonyl, Ci-Cg-Alkylaminothiocarbonyl, Di-Ci-Cg-Alkylaminothiocarbonyl, C 2 -Cg-Alkenyl, C 2 -Cg-Alkenyloxy, benzyl, benzyloxy, aryl, aryloxy Hetaryl
Hetaryloxy oder C ( =NOR7 ) -An-R8 ;Hetaryloxy or C (= NOR 7 ) -A n -R 8 ;
Wasserstoff,Hydrogen,
Ci-Cg-Alkyl, C2-Cg-Alkenyl , C2-Cg-Alkinyl , wobei dieCi-Cg-alkyl, C 2 -Cg-alkenyl, C 2 -Cg-alkynyl, the
Kohlenwasserstoffreste dieser Gruppen partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Reste tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkylaminocarbonyl,Hydrocarbon radicals of these groups can be partially or completely halogenated or can carry one to three of the following radicals: cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkylaminocarbonyl,
Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-Alkylaminothio- carbonyl , Di-Ci-Cg-alkylaminothiocarbonyl, Cχ-Cg-Alkyl- sulfonyl, Ci-Cg-Alkylsulfoxyl, Ci-Cg-Alkoxy, Ci-Cg- Halogenalkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Ci-Cg-Alkylamino, Di-Cχ-Cg-alkylamino, C2-Cg-Alkenyloxy, C3-Ce-Cycloalkyl, C3-Cg-Cycloalkyloxy, Heterocyclyl, Heterocyclyloxy, Aryl, Aryloxy, Aryl-Cι-C -alkoxy,Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, Cχ-Cg-alkyl- sulfonyl, Ci-Cg-alkylsulfoxyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-alkylamino, di-Cχ-Cg-alkylamino, C 2 -Cg Alkenyloxy, C 3 -C e -cycloalkyl, C 3 -Cg-cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl -CC -alkoxy,
Arylthio, Aryl-Cι-C4-alkylthio, Hetaryl, Hetaryloxy, Hetaryl-Cι-C4-alkoxy, Hetarylthio, Hetaryl-Cι-C -alkyl - thio, wobei die cyclischen Reste ihrerseits partiell oder vollständig halogeniert sein können und/oder ein bis drei der folgenden Gruppen tragen können:Arylthio, aryl -CC 4 -alkylthio, hetaryl, hetaryloxy, hetaryl -CC 4 -alkoxy, hetarylthio, hetaryl -CC -alkyl-thio, where the cyclic radicals in turn can be partially or completely halogenated and / or can wear one to three of the following groups:
Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkyl- sulfoxyl, C3C5-Cycloalkyl, Ci-Cg-Alkoxy, Cχ-Cg-Halogen- alkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Ci-Cg-Cyano, nitro, hydroxy, mercapto, amino, carboxyl, aminocarbonyl, aminothiocarbonyl, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 C 5 -cycloalkyl, Ci -Cg-alkoxy, Cχ-Cg-haloalkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Ci-Cg-
Alkylamino, Di-Ci-Cg-alkylamino, Cχ-Cg-Alkylaminocarbonyl, Di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-Alkyl- aminothiocarbonyl , Di-Ci-Cg-alkylaminothiocarbonyl , C2-Cg-Alkenyl, C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, Aryl, Aryloxy, Arylthio, Hetaryl, Hetaryloxy, Hetarylthio und C(=NOR7)-An-R8;Alkylamino, di-Ci-Cg-alkylamino, Cχ-Cg-alkylaminocarbonyl, di-Ci-Cg-alkylaminocarbonyl, Ci-Cg-alkylaminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C 2 -Cg-alkenyl, C 2 - Cg-alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, arylthio, hetaryl, hetaryloxy, hetarylthio and C (= NOR 7 ) -A n -R 8 ;
C3-Cg-Cycloalkyl, C3 -Cg-Cycloalkenyl, Heterocyclyl, Aryl, Hetaryl, wobei die cyclischen Reste partiell oder vollständig halogeniert sein können oder einen bis drei der folgenden Gruppen tragen können: Cyano, Nitro, Hydroxy, Mercapto, Amino, Carboxyl, Aminocarbonyl, Aminothiocarbonyl, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkylsulfonyl , Ci-Cg-Alkyl- sulfoxyl, C3-Cg-Cycloalkyl , Ci-Cg-Alkoxy, Ci-Cg-Halogen- alkoxy, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylthio, Cι~Cg- Alkylamino, Di-Ci-Cg-alkylamino, Ci-Cg-Alkylamino- carbonyl, Di-Ci-Cg-alkylaminocarbonyl , Cι~Cg-Alkyl- aminothiocarbonyl , Di-Ci-Cg-alkylaminothiocarbonyl , C -Cg-Alkenyl, C2-Cg-Alkenyloxy, Benzyl, Benzyloxy, C3 -CG-cycloalkyl, C3 -CG-cycloalkenyl, heterocyclyl, aryl, hetaryl, where the cyclic radicals may be partially or fully halogenated or may carry one to three of the following groups: cyano, nitro, hydroxy, mercapto, amino, Carboxyl, aminocarbonyl, aminothiocarbonyl, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkylsulfonyl, Ci-Cg-alkylsulfoxyl, C 3 -Cg-cycloalkyl, Ci-Cg-alkoxy, Ci-Cg -Halogen- alkoxy, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylthio, Cι ~ Cg- alkylamino, di-Ci-Cg-alkylamino, Ci-Cg-alkylamino-carbonyl, di-Ci-Cg-alkylaminocarbonyl, Cι ~ Cg Alkyl aminothiocarbonyl, di-Ci-Cg-alkylaminothiocarbonyl, C -Cg-alkenyl, C 2 -Cg-alkenyloxy, benzyl, benzyloxy,
Aryl, Aryloxy, Hetaryl und Hetaryloxy;Aryl, aryloxy, hetaryl and hetaryloxy;
wobeiin which
A für Sauerstoff, Schwefel oder Stickstoff steht und wobei der Stickstoff Wasserstoff oder Ci-Cg-Alkyl trägt;A represents oxygen, sulfur or nitrogen and the nitrogen carries hydrogen or Ci-Cg-alkyl;
n 0 oder 1 bedeutet;n represents 0 or 1;
R7 Wasserstoff oder Ci-Cg-Alkyl bedeutet und R8 Wasserstoff oder Cι~C6-Alkyl bedeutet,R 7 is hydrogen or Ci-Cg-alkyl and R 8 is hydrogen or -C ~ C 6 alkyl,
sowie deren Salze,and their salts,
undand
b) mindestens eine Verbindung der Formeln II bis XIb) at least one compound of the formulas II to XI
NO.NO.
CH. CH.
CH3 CH(CH3)2 CH 3 CH (CH 3 ) 2
.N.N
0 11 +0 11 +
in einer synergistisch wirksamen Menge. in a synergistically effective amount.
2. Mischung nach Anspruch 1, welche in zwei Teilen konditioniert ist, wobei der eine Teil die Verbindung I in einem festen oder flüssigen Träger enthält und der andere Teil mindestens eine der Verbindungen II bis XI in einem festen oder flüssi- gen Träger enthält.2. Mixture according to claim 1, which is conditioned in two parts, one part containing the compound I in a solid or liquid carrier and the other part containing at least one of the compounds II to XI in a solid or liquid carrier.
3. Verfahren zur Bekämpfung von Schadpilzen, dadurch gekennzeichnet, daß man die Pilze, deren Lebensraum oder die vor Pilzbefall zu schützenden Materialien, Pflanzen, Samen, Böden, Flächen oder Räume mit einer Mischung gemäß einem der Ansprüche 1 oder 2 behandelt, wobei die Anwendung der Verbindung I und mindestens einer der Verbindungen II bis XI gleichzeitig, und zwar gemeinsam oder getrennt, oder nacheinander erfolgen kann.3. A method of combating harmful fungi, characterized in that the fungi, their habitat or the materials, plants, seeds, soils, areas or spaces to be protected from fungal attack are treated with a mixture according to one of claims 1 or 2, the application the compound I and at least one of the compounds II to XI can be carried out simultaneously, namely together or separately, or in succession.
4. Verfahren nach Anspruch 3, dadurch gekennzeichnet, daß man die Schadpilze, deren Lebensraum oder die von ihnen freizuhaltenden Pflanzen, Samen, Böden, Flächen, Materialien oder Räume mit 0,005 bis 1 kg/ha einer Verbindung I gemäß Anspruch 1 behandelt. 4. The method according to claim 3, characterized in that treating the harmful fungi, their habitat or the plants, seeds, soils, surfaces, materials or spaces to be kept free by them with 0.005 to 1 kg / ha of a compound I according to claim 1.
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