EP1082009A1 - Melanges fongicides a base de derives d'oximether de diatomite et d'insecticides - Google Patents

Melanges fongicides a base de derives d'oximether de diatomite et d'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)
English (en)
Inventor
Klaus Schelberger
Thomas Grote
Hubert Sauter
Eberhard Ammermann
Gisela Lorenz
Siegfried Strathmann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1082009A1 publication Critical patent/EP1082009A1/fr
Withdrawn legal-status Critical Current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

L'invention concerne a) des dérivés d'acide phénylacétique de la formule (I), dans laquelle les substituants et l'indice ont la signification indiquée dans la description, ainsi que leurs sels, et b) au moins un composé des formules (II) à (XI) en quantités produisant un effet synergique.
EP99910371A 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'insecticides Withdrawn EP1082009A1 (fr)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
DE19812762 1998-03-24
DE19812762 1998-03-24
DE19855331 1998-12-01
DE19855331 1998-12-01
PCT/EP1999/001908 WO1999048366A1 (fr) 1998-03-24 1999-03-22 Melanges fongicides a base de derives d'oximether de diatomite et d'insecticides

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EP1082009A1 true EP1082009A1 (fr) 2001-03-14

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JP (1) JP4458666B2 (fr)
KR (1) KR100557365B1 (fr)
CN (1) CN1139323C (fr)
AR (1) AR018809A1 (fr)
AU (1) AU735903B2 (fr)
BR (1) BR9909048A (fr)
CA (1) CA2324460A1 (fr)
CO (1) CO5060421A1 (fr)
ID (1) ID26839A (fr)
IL (1) IL138295A0 (fr)
MX (1) MXPA00008747A (fr)
TW (1) TW520274B (fr)
WO (1) WO1999048366A1 (fr)

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DE19956098A1 (de) * 1999-11-22 2001-05-23 Bayer Ag Fungizide Wirkstoffkombinationen
KR100805559B1 (ko) * 2000-12-18 2008-02-20 바스프 악티엔게젤샤프트 옥심 에테르 유도체 기재의 살진균제 혼합물
DE10140108A1 (de) * 2001-08-16 2003-03-06 Bayer Cropscience Ag Fungizide Wirkstoffkombinationen
NZ551540A (en) * 2002-03-08 2009-05-31 Basf Ag Fungicidal mixtures based on prothioconazole and containing an insecticide
DE602004021026D1 (de) 2003-12-18 2009-06-18 Basf Se Fungizide mischungen auf grundlage von carbamatderivaten und insektiziden
NZ555623A (en) * 2004-12-20 2009-04-30 Basf Ag Method for controlling mycoses in leguminous plants
DE102004062513A1 (de) * 2004-12-24 2006-07-06 Bayer Cropscience Ag Insektizide auf Basis von Neonicotinoiden und ausgewählten Strobilurinen
CA2597643C (fr) 2005-02-22 2014-01-28 Basf Aktiengesellschaft Compositions comprenant un neonicotinoide et un boscalid et leur utilisation comme pesticides
KR20090108734A (ko) * 2007-02-06 2009-10-16 바스프 에스이 살충 혼합물
JP5166514B2 (ja) 2007-04-25 2013-03-21 ビーエーエスエフ ソシエタス・ヨーロピア 殺菌混合物
EA201001234A1 (ru) * 2008-02-05 2011-04-29 Басф Се Пестицидные смеси
WO2009098228A2 (fr) * 2008-02-05 2009-08-13 Basf Se Mélanges pesticides
EP2306834B1 (fr) 2008-07-04 2018-09-12 Basf Se Mélanges fongicides comprenant un 1-méthylpyrazol-4-ylcarboxanilide substitué
MX2012003018A (es) 2009-09-29 2012-04-19 Basf Se Mezclas pesticidas.
WO2011039105A2 (fr) 2009-09-29 2011-04-07 Basf Se Mélanges pesticides
BR112012012754A2 (pt) * 2009-12-02 2015-09-08 Basf Se "misturas, composição pesticida, método de controle de pragas, método de proteção de material de propagação vegetal contra pragas e material de propagação vegetal"
JP2012102075A (ja) * 2010-10-14 2012-05-31 Sumitomo Chemical Co Ltd 有害生物防除用組成物及び有害生物防除方法

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DE19539324A1 (de) * 1995-10-23 1997-04-24 Basf Ag Phenylessigsäurederivate, Verfahren und Zwischenprodukte zu ihrer Herstellung und sie enthaltende Mittel

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AR018809A1 (es) 2001-12-12
BR9909048A (pt) 2000-12-05
AU2934899A (en) 1999-10-18
CN1139323C (zh) 2004-02-25
IL138295A0 (en) 2001-10-31
JP2002507551A (ja) 2002-03-12
MXPA00008747A (es) 2001-03-01
CA2324460A1 (fr) 1999-09-30
AU735903B2 (en) 2001-07-19
KR100557365B1 (ko) 2006-03-10
WO1999048366A1 (fr) 1999-09-30
CO5060421A1 (es) 2001-07-30
KR20010034646A (ko) 2001-04-25
TW520274B (en) 2003-02-11
JP4458666B2 (ja) 2010-04-28
CN1294488A (zh) 2001-05-09
ID26839A (id) 2001-02-15

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