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WO2006037553A1 - Associations de principes actifs insecticides contenant des derives d'acide nicotinique d'halogenure d'alkyle et des pyrethroides - Google Patents

Associations de principes actifs insecticides contenant des derives d'acide nicotinique d'halogenure d'alkyle et des pyrethroides Download PDF

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Publication number
WO2006037553A1
WO2006037553A1 PCT/EP2005/010521 EP2005010521W WO2006037553A1 WO 2006037553 A1 WO2006037553 A1 WO 2006037553A1 EP 2005010521 W EP2005010521 W EP 2005010521W WO 2006037553 A1 WO2006037553 A1 WO 2006037553A1
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Prior art keywords
alkyl
spp
cycloalkyl
aryl
substituted
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PCT/EP2005/010521
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German (de)
English (en)
Inventor
Erich Sanwald
Waltraud Hempel
Koichi Araki
Tetsuya Murata
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Bayer Cropscience Gmbh
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Publication of WO2006037553A1 publication Critical patent/WO2006037553A1/fr

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    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the present invention relates to new active compound combinations which consist of known haloalkyl nicotinic acid derivatives on the one hand and other known insecticidal active compounds on the other hand and are very suitable for controlling animal pests such as insects and unwanted acarids.
  • R 1 is C r C 4 -haloalkyl
  • R 2 and R 3 independently of one another represent hydrogen or hydroxyl, in each case optionally mono- or polysubstituted, identically or differently, by R 4 ,
  • Ci-C 8 alkyl C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C r C 6 alkoxy, C 3 -C 3 cycloalkyl, or cycloalkyl-Q-CRCG C ⁇ - alkyl, where the substituents oximino and hydrazono are each in turn unsubstituted or by C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 3 -C 8 -cycloalkyl, C 3 - C 8 -cycloalkyl-C r C 6 alkyl, CRCG-alkoxy-Ci-Cs-alkyl, cyano-QQ-alkyl, C r C 8 alkylthio
  • R 2 and R 3 together with the nitrogen atom to which they are attached form a 3- to 8-membered saturated, unsaturated or aromatic heterocyclic ring optionally containing up to three further heteroatoms from the group of nitrogen, sulfur and oxygen, and which is unsubstituted or identical or different substituents from the one or more radicals R 4, C r C 6 alkyl, QC 6 -
  • Haloalkyl C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, oxo, oximino or hydrazono, wherein the substituents oximino and hydrazono are in turn unsubstituted or by C 1 -C 8 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C r C 6 alkyl, C r C 8 alkoxy-Ci-C 8 alkyl, cyano-Ci-C 8 - alkyl, Q-Cs-alkylthio-Ci-Cs-alkyl, Q-Cs-alkyl-carbonyl, Ci-Cg-alkoxy-carbonyl, di- (C r C 8 alkyl) amino-carbonyl,
  • Aryl or -CH 2 -aryl can be substituted
  • R 4 is halogen, Ci-C 6 alkoxy, C r C 6 haloalkoxy, -S (O) n -C-C 6 -alkyl, -S (O) n -C 1 -C 6 -
  • Haloalkyl hydroxy, cyano, carboxy, azido, C 1 -C 6 -alkoxycarbonyl, nitro, di-
  • Ci-C 6 alkyl amino, or optionally monosubstituted or polysubstituted by identical or comparable secreted by Ci-C 6 alkyl, Ci-C 6 haloalkyl and / or halogen-substituted
  • n 0, 1 or 2
  • R 5 is 6 haloalkyl for R 4, Ci-Ce-alkyl or C r C,
  • X is oxygen or sulfur
  • Y is R 6 , OR 6 , SR 6 , NR 7 R 8 ,
  • W is oxygen or sulfur
  • R 6 is in each case optionally mono- or polysubstituted, identically or differently by R 4, substituted Cj-Cg-alkyl, C 3 -C 8 -cycloalkyl or GrCg-cycloalkyl-Q-Ce-alkyl, or in each case optionally mono- or polysubstituted, the same or aryl, heterocyclyl, -CH 2 -aryl or -CH 2 -heterocyclyl which is differently substituted by R 5 ,
  • R 7 represents hydroxyl, represents in each case optionally monosubstituted or polysubstituted by identical or different substituted by the R 4 C r C 8 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 -Alkmyl, C 1 -C 8 - Alkoxy, hydroxyC r C 8 alkyl, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 8 cycloalkyl,
  • R 8 represents hydrogen, for each optionally mono- or polysubstituted, identical or different R 4 -substituted C r C 8 -alkyl, C 3 -C 8 -cycloalkyl or C 3 -C 8 -cycloalkyl-C 1 -C 6 alkyl, cyclyl represents in each case optionally monosubstituted or polysubstituted by identical or different substituents R 5 substituted aryl, heterocyclyl, -CH 2 aryl or -CH 2 -Hetero-,
  • R 9 and R 10 independently of one another in each case optionally monosubstituted or polysubstituted by identical or different substituents R 4 is substituted C r C 8 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 -Alkmyl,
  • QrQ-cycloalkyl or GrCs-cycloalkyl-d-Ce-alkyl, for -G ( X) -Y, in each case optionally mono- or polysubstituted, identically or differently by R 5 -substituted aryl, heterocyclyl, -CH 2 -aryl or -CH 2- heterocyclyl is
  • R 9 and R 10 together with the sulfur atom to which they are attached form a 3- to 8-membered saturated or unsaturated heterocyclic ring which optionally contains up to three further heteroatoms from the group of nitrogen, sulfur and oxygen, and which is unsubstituted or the same or different is substituted by one or more radicals R 4 , Ci-C 6 alkyl, C r C 6 haloalkyl, oxo, oximino or hydrazono, wherein the substituents oximino and hydrazono are in turn unsubstituted or by C r C 8 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, Cs-Cg-cycloalkyl, C 3 -C 8 cycloalkyl-Ci-C 6 alkyl, C, -C 8 alkoxy-C r C 8 alkyl, cyano Ci-C 8 alkyl, C r C 8 alkylthio-
  • Het / heterocyclyl is a cyclic radical which may be completely saturated, partially unsaturated or completely unsaturated or aromatic and which is substituted by at least one or more identical or different atoms from the group of nitrogen,
  • the cyclic radical is unsubstituted or substituted by one or more radicals R 4 , C 1 -C 6 - AllCyI, Ci-C 6 -haloalkyl, Ci-C 8 -alkoxy- C] -C 8 -alkyl, Ci-C 8 -alkylthio-Ci-C 8 -alkyl, oxo, oximino or hydrazono, wherein the
  • Substituents oximino and hydrazono in turn are unsubstituted or substituted by Ci-C 8 - alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 3 -C 8 cycloalkyl, C 3 -C 8 cycloalkyl-C 1 -C 6 alkyl, C 8 alkoxy-C, -C 8 alkyl, cyano-C r C 8 alkyl, C, -C 8 alkylthio-Ci-C 8 alkyl, C r C 8 - Alkylcarbonyl, Q-Cg-alkoxycarbonyl, di- (C 1 -C 8 -alkyl) -amino-carbonyl, aryl or -CH 2 -aryl can be substituted,
  • R -CH 3 or -CO 2 CH 3
  • insecticidal and acaricidal activity of the combination of active substances according to the invention is substantially higher than the sum of the effects of the individual active substances. There is an unpredictable true synergistic effect and not just an effect supplement.
  • the active compound combinations according to the invention contain, in addition to at least one active substance of the formula (I) or a salt of the active compound of the formula (T), at least one active compound of the compounds 1 to 23.
  • R 1 preferably represents mono- or polysubstituted, identically or differently by fluorine and / or chlorine-substituted C 1 -C 4 -alkyl, particularly preferably CF 3 , CHF 2 or CF 2 Cl, very particularly preferably CF 2 ;
  • R 2 and R 3 independently of one another preferably represent hydrogen or hydroxyl, in each case optionally mono- or polysubstituted, identically or differently, by R 4 or
  • Alkylthio-C r C 8 alkyl, dQ-alkyl-carbonyl, d-Cs-alkoxy-carbonyl, di- (C r -C 8 alkyl) - amino-carbonyl, aryl or -CH 2 -aryl which may be substituted, for -C ( X) -Y, or for each optionally mono- or polysubstituted, identically or differently, R 5 -substituted aryl, heterocyclyl, -CH 2 -aryl or -CH 2 -heterocyclyl,
  • R 2 and R 3 together with the nitrogen atom to which they are attached, preferably form a 3- to 8-membered saturated, unsaturated or aromatic heterocyclic ring which optionally contains up to three further heteroatoms from the group of nitrogen, sulfur and oxygen, and which is unsubstituted or substituted by one or more radicals
  • R 4 Ci-C 6 alkyl, Ci-C 6 haloalkyl or oximino wherein the substituent oximino turn is unsubstituted or substituted by QC 8 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 -alkynyl, C 3 -C 8 - cycloalkyl, C 3 -C 8 cycloalkyl-C r C 6 alkyl, C r C 8 alkoxy-C, -C 8 alkyl, cyano-C, -C 8 alkyl, C 1 - C 8 alkylthio-Ci-C 8 alkyl, d-Cg-alkyl-carbonyl, C r C 8 -alkoxy-carbonyl, di- (C 1 -C 8 -alkyl> amino-carbonyl, aryl or -CH 2 - Aryl may be substituted,
  • R 4 is preferably halogen, C r C 6 alkoxy, C r C 6 haloalkoxy, -S (O) n -C r C 6 alkyl, cyano, carboxy, azido, C 6 alkoxy-carbonyl, nitro or Di (C 1 -C 6 alkyl) amino,
  • n is preferably 0, 1 or 2
  • R 5 is preferably R 4 , C 1 -C 6 -alkyl or C 1 -C 6 -haloalkyl,
  • X is preferably oxygen
  • X is also preferably sulfur
  • Y is preferably R 6 , OR 6 , SR 6 , NR 7 R 8 ,
  • W is preferably oxygen
  • W is also preferably sulfur
  • R 6 is preferably in each case optionally mono- or polysubstituted by identical or different substituents R 4 -substituted Q-Cg-alkyl, C 3 -C 8 -cycloalkyl or C 3 -C 8 -cycloalkyl-C r C 6 -alkyl, or for each optionally mono- or polysubstituted, identically or differently, R 5 -substituted aryl, heterocyclyl, -CH 2 -aryl or -CH 2 -heterocyclyl,
  • R 7 preferably represents hydroxyl, in each case optionally mono- or polysubstituted by identical or different substituents R 4 -substituted Q-Cg-alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, QC 8 -alkoxy, hydroxyl Q-Cg-alkyl, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-QC 6 -alkyl, -O-CH 2 -C C 3 -C 8 -cycloalkyl, in each case optionally mono- or polysubstituted, identically or differently, by R 5 -substituted aryl, heterocyclyl, aryloxy, heterocyclyloxy, -CH 2 -aryl, -O-CH 2 -aryl,
  • R 8 preferably represents hydrogen, in each case optionally monosubstituted or polysubstituted by identical or different substituents by R 4 substituted QC 8 alkyl, C 3 -C 8 cycloalkyl or C 3 -C 8 - cycloalkyl-Ci-C 6 alkyl, for in each case optionally mono- or polysubstituted, identical or differentiated by R 5 -substituted aryl, heterocyclyl, -CH 2 -aryl or -CH 2 heterocyclyl,
  • R 9 and R 10 together with the sulfur atom to which they are attached, preferably form a 3- to 8-membered saturated or unsaturated heterocyclic ring which optionally contains up to three further heteroatoms from the group of nitrogen, sulfur and oxygen, and is unsubstituted or substituted by one or more radicals R 4 , Ci-C 6 alkyl, Q- C 6 haloalkyl, oxo, oximino or hydrazono, wherein the substituents oximino and
  • Hydrazono are in turn unsubstituted or by Q-Cg-alkyl, C 3 -C 6 alkenyl, C 3 -C 6 - alkynyl, C 3 -C 8 -cycloalkyl, C 3 -C 8 -cycloalkyl-C r C 6 -alkyl , Q-Cg-alkoxy-Q-Cs-alkyl, cyano-QC 8 -alkyl, C 1 -C 9 -alkylthio-QQ-alkyl, C 1 -C 8 -alkylcarbonyl, C 1 -C 8 -alkoxycarbonyl, di (QC 8 -alkyl) - amino-carbonyl, aryl or -CH 2 -aryl can be substituted,
  • Hefeterocyclyl preferably represents a cyclic radical from the series thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3,4- Triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, 1,2,3,4-tetrazole, benzo [b] thiophene, benzo [b] furan, indole, benzo [c] thiophene, benzo [c] furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, Benzothiadiazole, benzotriazole, dibenzofi ⁇ ran, dibenz
  • R 4 is particularly preferably fluorine, chlorine, methoxy, ethoxy, n- or iso-propyloxy, n-, iso-, secondary- or tertiary-butyloxy, trifluoromethoxy, thiomethyl, thioethyl, sulfonylmethyl, sulfonylethyl, sulfonylmethyl or sulfonylethyl,
  • R 5 particularly preferably represents R 4 , methyl, ethyl, n- or iso-propyl, n-, iso-, secondary- or tert-butyl or for trifluoromethyl,
  • R 6 particularly preferably represents in each case optionally mono- or polysubstituted by identical or different R 4 -substituted methyl, ethyl, n- or iso-propyl, n-, iso-, secondary- or tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, or for each optionally mono- or polysubstituted by identical or different substituents by R 5
  • R 7 particularly preferably represents hydroxyl, in each case optionally monosubstituted or polysubstituted, identically or differently by R 4, substituted methyl, ethyl, n- or iso-propyl, n-, iso-, secondary or tertiary-butyl propenyl, butenyl, propynyl, butynyl, methoxy, ethoxy, n- or iso-propyloxy, n-, iso-, secondary or tertiary-butyloxy, propenyloxy, butenyloxy, propinyloxy, butinyloxy, or for each optionally simple or multiply, identically or differently by R 5 substituted phenyl, phenyloxy, benzyl or benzyloxy,
  • R 8 particularly preferably represents hydrogen, in each case optionally mono- or polysubstituted, identically or differently by R 4, substituted methyl, ethyl, n- or iso-propyl, n-, iso-, secondary or tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl , Cyclohexyl, or for each optionally mono- or polysubstituted by identical or different substituents R 5 -substituted phenyl or bercyl,
  • R 9 and R 10 independently of one another particularly preferably represent substituted methyl, ethyl, n- or iso-propyl, n-, iso-, secondary- or tertiary-butyl, propenyl, each optionally mono- or polysubstituted, identically or differently by R 4 Butenyl, propynyl, butynyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or for in each case optionally mono- or polysubstituted by identical or different substituents R 5 -substituted phenyl or benzyl,
  • Het / heterocylyl particularly preferably represents a cyclic radical from the series thiophene, furan, pyrrole, thiazole, oxazole, imidazole, isothiazole, isoxazole, pyrazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,3, 4-triazole, 1,2,4-oxadiazole, 1,2,4-thiadiazole, 1,2,4-triazole, 1,2,3-triazole, benzo [b] thiophene, benzo [b] furan, Indole, benzo [c] thiophene, benzo [c] furan, isoindole, benzoxazole, benzothiazole, benzimidazole, benzisoxazole, benzisothiazole, benzopyrazole, benzothiadiazole, benzotriazole, dibenzofuran, dibenzothiophene, pyridine, pyrazin
  • W is oxygen and R and R .10 are particularly preferred.
  • W is oxygen
  • R 2 is hydrogen
  • X is oxygen
  • Y is -OR 6 , where R 6 is in each case optionally mono- or polysubstituted, identical or different R 5 is substituted benzyl, furylmethyl or thienylmethyl and R 5 has the particularly preferred condition.
  • W is oxygen
  • R 2 is hydrogen
  • X is oxygen
  • Y is -NR 7 R 8 , wherein R 7 is methoxy, ethoxy, n- or iso -Propyloxy, n-, iso-, secondary- or tertiary-butyloxy, propenyloxy, butenyloxy, propinyloxy or butinyloxy and R 8 is methyl, ethyl, n- or iso-propyl, n-, iso-, secondary or tertiary-butyl stands.
  • salts of the active compounds of the formula (I) which can be used as alternatives according to the invention, the sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 -alkylammonium, di (C 1 -C 4) alkyl) -ammonium, Tn- (C j -C 4 -alkyl) -ammonium, Tefra (Ci-C4-alkyl) -ammonium, Tn- (C 1 -C 4 -alkyl) sulfonium, C5 or Cg -Cycloalkyl-ammomum- and di- (Ci-C2-alkyl) -benzyl-amrnonium- called salts of these drugs.
  • Flucythrinate (lc-8) -Na + lambda-cyhalothrin, (lc-8) -Na + permethrin, (lc-8) -Na + taufluvalinate, (lc-8) -Na + tralomethrin, (lc-8 ) -Na + zeta-cypermethrin, (Ic-8) -Na + cyfluthrin, (I-c-8) -Na + bifenthrin, (Ic-8) -Na + cycloprothrin, (Ic-8) -Na + eflusilanate, (Ic-8) -Na + Fubfenprox, (Ic-8) -Na + pyrethrin, (Ic-8) -Na + resmethrin.
  • the active ingredient combinations may also contain other fungicidal, acaricidal or insecticidal Zumischkomponenten beyond. If the active ingredients in the active compound combinations according to the invention are present in certain weight ratios, the synergistic effect is particularly pronounced. However, the weight ratios of the active ingredients in the drug combinations can be varied within a relatively wide range.
  • the combinations according to the invention comprise active compounds of the formula (I) or salts thereof and the mixing partner in the preferred and particularly preferred mixing ratios indicated in the table below:
  • the active compound combinations according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and spider animals, which occur in agriculture, animal health, in forests, in the protection of stored products and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • animal pests preferably arthropods and nematodes, in particular insects and spider animals, which occur in agriculture, animal health, in forests, in the protection of stored products and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Isopoda for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber. From the order of Diplopoda eg Blaniulus guttulatus.
  • Chilopoda e.g. Geophilus carpophagus, Scutigera spp.
  • Symphyla e.g. Scutigerella immaculata.
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera e.g. Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
  • Thysanoptera e.g. Herculothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Heteroptera e.g. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cirnex lectularius, Rhodnius prolixus, Triatoma spp.
  • Otiorrhynchus sulcatus Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Diptera e.g. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp.
  • Oestrus spp. Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp.
  • siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp.
  • arachnids e.g. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.
  • Chorioptes spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
  • the plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, Granules, suspension-emulsion concentrates, active substance-impregnated natural and synthetic substances as well as ultrafine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Suitable solid carriers are:
  • Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules come into question: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corncobs and tobacco stems; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin-sulphite liquors and methylcellulose.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention can be present in commercially available formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides.
  • the insecticides include, for example, phosphoric esters, carbamates, carboxylic esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms, and the like.
  • the active compound combinations according to the invention can furthermore be present when used as insecticides in their commercial formulations and in the formulations prepared from these formulations in admixture with synergists.
  • Synergists are compounds by which the effect of the active ingredients is increased without the added synergist itself having to be actively active.
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
  • the application is done in a custom forms adapted to the application forms.
  • Wirkstoffkombina ⁇ tions When used against hygiene and storage pests, the Wirkstoffkombina ⁇ tions are characterized by an excellent residual effect on wood and clay and by a good alkali stability on limed documents.
  • the active compound combinations of the invention not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ectoparasites) such as ticks, leather ticks, mange mites, mites, flies (stinging and licking), parasitic fly larvae, lice, hair pieces, Featherlings and fleas.
  • animal parasites ectoparasites
  • ectoparasites such as ticks, leather ticks, mange mites, mites, flies (stinging and licking), parasitic fly larvae, lice, hair pieces, Featherlings and fleas.
  • parasites include: From the order of the Anoplurida eg Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp , Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Chrysomyia spppp
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compound combinations according to the invention are also suitable for controlling
  • Arthropods farm animals, such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, caged birds, .Aquarium fish and so-called Experimental animals, such as Hamsters, guinea pigs, rats and mice.
  • enteral administration in the form of, for example, tablets, capsules, infusions, Drenchen, granules, pastes, BoIi, the feed-through process, suppositories
  • parenteral administration such as by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants
  • nasal application by dermal application in the form of, for example, dipping or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, Mark réellesvor ⁇ directions, etc.
  • the active ingredient combinations When used for livestock, poultry, pets, etc., the active ingredient combinations may be used as formulations (for example, powders, emulsions, flowables) containing the active ingredients in an amount of 1 to 80% by weight, directly or after 100 to 10,000 dilution or use as a chemical bath.
  • formulations for example, powders, emulsions, flowables
  • the active compound combinations according to the invention have a high insecticidal activity against insects which destroy industrial materials.
  • insects By way of example and preferably without limiting however, the following insects are mentioned:
  • Kalotermes flavicollis Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulite ⁇ nes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
  • the material to be protected from insect attack is wood and woodworking products.
  • the active compound combinations can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and other processing aids.
  • the insecticidal agents or concentrates used for the protection of wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.
  • the amount of agents or concentrates used depends on the type and occurrence of
  • Insects and dependent on the medium The optimal amount used can be determined in each case by test series. In general, however, it is sufficient 0.0001 to 20 wt .-%, preferably 0.001 to 10 wt .-%, of the active ingredient, based on the material to be protected, use.
  • the solvent and / or diluent used is an organic-chemical solvent or solvent mixture and / or an oily or oily, volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally one Emulsifier and / or wetting agent.
  • organic-chemical solvents are preferably oily or oil-like solvents having an evaporation number above 35 and a flash point above 30 0 C, preferably above 45 ° C used.
  • suitable mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures preferably white spirit, petroleum and / or alkylbenzene are used.
  • Mineral oils having a boiling range of 170 to 220 0 C, white spirit having a boiling range of 170 to 220 0 C., spindle oil with a boiling range of 250 to 350 0 C, petroleum and aromatics with a boiling range of 160 to 280 0 C, oil of turpentine and Like. For use.
  • the organic low volatile oily or oily solvents having an evaporation number above 35 and a flash point above 30 0 C, preferably above 45 0 C, can be partially replaced by light or medium volatile organic chemical solvents, with the devis ⁇ task that the solvent mixture is also a Evaporation rate above 35 and a flash point above 30 0 C, preferably above 45 0 C, and that the mixture is soluble or emulsifiable in this solvent mixture.
  • a portion of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups are used, for example glycol ethers, esters or the like.
  • the organic-chemical binders used are the water-dilutable and / or soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils, in particular binders consisting of or containing Acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders used on the basis of a natural and / or synthetic resin.
  • binders consisting of or containing Acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene coumarone resin, silicone resin, drying vegetable and / or drying
  • the synthetic resin used as the binder may be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellent agents, odor correctors and inhibitors or corrosion inhibitors and the like can be used.
  • organic-chemical binders it is preferred to contain at least one alkyd resin or modified alkyd resin and / or one drying vegetable oil in the middle or in the concentrate.
  • Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
  • the mentioned binder can be completely or partially replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to volatilize the active ingredients and crystallize or precipitate! prevent. Preferably, they replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers are derived from the chemical classes of phthalic acid esters such as dibutyl, di-ethyl or benzyl butyl phthalate, phosphoric esters such as tributyl phosphate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or higher molecular weight glycol ethers , Glycerol esters and p-toluenesulfonic acid esters.
  • phthalic acid esters such as dibutyl, di-ethyl or benzyl butyl phthalate
  • phosphoric esters such as tributyl phosphate
  • adipic acid esters such as di (2-ethylhexyl) adipate
  • stearates such as butyl
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Particularly suitable solvents or diluents are also water, optionally in admixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved by large-scale impregnation, eg vacuum, double vacuum or printing process.
  • the active compound combinations according to the invention can be used to protect against fouling of objects, in particular of hulls, screens, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • heavy metals such as, for example, in bis (trialkyltin) sulfides, tri-w-butyltin laurate, tri-n-butyltin chloride, copper (I) oxide, triethyltin chloride, tri-7z-butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide, Antimony oxide, polymeric butyl titanate, phenyl (bispyridine) bismuth chloride, tri-n-butyltin fluoride, manganese ethylene bis-thiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinethiol-l-oxide, bisdimethyldithiocarbamoylzinc ethylene bisthiocarbamate, zinc oxide, copper (I) Ethylene-bisd
  • the ready-to-use antifouling paints may optionally contain other active substances, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • the antifouling agents used contain the active compound combinations according to the invention in a concentration of 0.001 to 50 wt .-%, in particular from 0.01 to 20 wt .-%.
  • the antifouling agents of the invention further contain the usual ingredients, e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, especially in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile Rubbers, drying oils, such as linseed oil, rosin esters or modified hard resins in combination with tar or bitumens, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • paints also contain inorganic pigments, organic pigments or dyes which are preferably insoluble in seawater.
  • paints may contain materials such as rosin to allow for controlled release of the active ingredients enable.
  • the paints may further include plasticizers, rheology modifiers, and other conventional ingredients.
  • the compounds according to the invention or the above-mentioned mixtures can also be incorporated in silk-polishing antifouling systems.
  • insects in particular insects, arachnids and mites, which are used in closed rooms, such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. They can be used to control these pests in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
  • Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • Application is in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with evaporator plates of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propellergetrie ⁇ benen evaporators, energy-less or passive evaporation systems, moth papers, mantle bags and moth gels, as granules or dusts, in straw baits or bait stations.
  • Pump and atomizer sprays e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with evaporator plates of cellulose or plastic, liquid evaporators, gel and membrane evaporators, propellergetrie ⁇ benen evaporators, energy-less or passive evaporation systems, moth papers, mantle bags and moth gels, as granules or dusts, in straw baits or bait stations.
  • plants and parts of plants can be treated.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods 1 , including the transgenic plants and including lent to plant variety protection or non-protectable plant varieties.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes be listed.
  • the plant parts also include crops as well as vegetative and generative propagation material, for example cuttings, tubers, rhiomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, spreading, spreading and in propagation material, in particular in seeds, further by single or multi-layer wrapping.
  • all plants and their parts can be treated according to the invention.
  • wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” has been explained above.
  • the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of the harvested products possible, which go beyond the actual expected effects.
  • the preferred plants or plant varieties to be treated according to the invention to be treated include all plants produced by the genetic engineering modification obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
  • traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products.
  • Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses and an increased tolerance of the plants to certain herbicidal active compounds.
  • transgenic plants include the important crops such as cereals (wheat, rice), corn, soy, potato, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soy, potato, cotton and rapeseed should be highlighted.
  • Traits which are particularly emphasized are the increased defense of the plants against insects by toxins formed in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CrylHA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryEF and combinations thereof) are produced in the plants (hereinafter "Bt plants”).
  • “traits”) which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT” gene).
  • the genes which confer the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names YTELD GARD® (eg corn, cotton, soya), KnockOut® (eg corn), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Herbicide-resistant plants plants grown in a conventional manner with herbicide tolerance
  • the listed plants can be treated particularly advantageously according to the invention with the erfindungs ⁇ according drug mixtures.
  • the preferred ranges given above for the mixtures also apply to the treatment of these plants.
  • Particularly emphasized is the plant treatment with the mixtures specifically mentioned in the present text.
  • Active ingredient A at a rate of m ppm, Y the kill rate, expressed in% of the untreated control, when using the
  • Active ingredient B at a rate of n ppm
  • E means the degree of killing, expressed in% of the untreated control, when using the active compound A and B at application rates of m and n ppm,
  • the combination is over-additive in its kill, ie, there is a synergistic effect.
  • the actually observed kill rate must be greater than the expected kill rate (E) value calculated from the above formula.
  • a corresponding part by weight of formulated product is mixed with water to obtain the desired concentration.
  • Barley plants (Hordeum vulgare), which are infected with cereal aphids (Metopolophium dirhodum), are treated by spraying with the preparation solution in the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • the determined kill values are calculated according to the Colby formula.

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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 des associations de principes actifs à base de composés de formule (I), dans laquelle R1 et A ont les significations indiquées dans la description, et de pyréthroïdes, ces associations possédant d'excellentes propriétés insecticides et acaricides. L'invention concerne également l'utilisation de ces associations et des procédés de production desdites associations.
PCT/EP2005/010521 2004-10-06 2005-09-29 Associations de principes actifs insecticides contenant des derives d'acide nicotinique d'halogenure d'alkyle et des pyrethroides WO2006037553A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004048527.5 2004-10-06
DE200410048527 DE102004048527A1 (de) 2004-10-06 2004-10-06 Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften

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WO2006037553A1 true WO2006037553A1 (fr) 2006-04-13

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0246331A1 (fr) * 1985-11-11 1987-11-25 Nippon Kayaku Kabushiki Kaisha Composition insecticide
FR2784011A1 (fr) * 1998-10-05 2000-04-07 Rhone Poulenc Agrochimie Composition insecticide comprenant de la cypermethrine et de l' acetamiprid
WO2001065941A1 (fr) * 2000-03-08 2001-09-13 Aventis Cropscience S.A. Procede de lutte contre les arthropodes ravageurs des cultures et composition utile pour ce procede
WO2002034050A1 (fr) * 2000-10-23 2002-05-02 Ishihara Sangyo Kaisha, Ltd. Composition pesticide
WO2002037964A1 (fr) * 2000-11-10 2002-05-16 Syngenta Participations Ag Compositions pesticides synergetiques a base de n-cyanomethyl-4-(trifluoromethyl)nicotinamide
WO2003069990A2 (fr) * 2002-02-22 2003-08-28 Ishihara Sangyo Kaisha, Ltd. Composition de lutte contre les insectes dans les habitations et procede de lutte contre lesdits insectes

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0246331A1 (fr) * 1985-11-11 1987-11-25 Nippon Kayaku Kabushiki Kaisha Composition insecticide
FR2784011A1 (fr) * 1998-10-05 2000-04-07 Rhone Poulenc Agrochimie Composition insecticide comprenant de la cypermethrine et de l' acetamiprid
WO2001065941A1 (fr) * 2000-03-08 2001-09-13 Aventis Cropscience S.A. Procede de lutte contre les arthropodes ravageurs des cultures et composition utile pour ce procede
WO2002034050A1 (fr) * 2000-10-23 2002-05-02 Ishihara Sangyo Kaisha, Ltd. Composition pesticide
WO2002037964A1 (fr) * 2000-11-10 2002-05-16 Syngenta Participations Ag Compositions pesticides synergetiques a base de n-cyanomethyl-4-(trifluoromethyl)nicotinamide
WO2003069990A2 (fr) * 2002-02-22 2003-08-28 Ishihara Sangyo Kaisha, Ltd. Composition de lutte contre les insectes dans les habitations et procede de lutte contre lesdits insectes

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