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Dokumentenidentifikation EP1191847 21.04.2005
EP-Veröffentlichungsnummer 0001191847
Titel AMEISENBEKÄMPFUNGSMITTEL UND VERFAHREN ZU DEREN EINSATZ
Anmelder BASF AG, 67063 Ludwigshafen, DE
Erfinder TAKAGI, Kazuhiro, Osaka-shi, Osaka-fu, JP;
WADA, Yasuhiro, Osakasayama-shi, Osaka-fu, JP;
YAMAGUCHI, Rikio, Kawachinagano-shi, Osaka-fu, JP
DE-Aktenzeichen 60018749
Vertragsstaaten AT, BE, CH, CY, DE, DK, ES, FI, FR, GB, GR, IE, IT, LI, LU, MC, NL, PT, SE
Sprache des Dokument EN
EP-Anmeldetag 28.06.2000
EP-Aktenzeichen 009449893
WO-Anmeldetag 28.06.2000
PCT-Aktenzeichen PCT/US00/17895
WO-Veröffentlichungsnummer 0001001781
WO-Veröffentlichungsdatum 11.01.2001
EP-Offenlegungsdatum 03.04.2002
EP date of grant 16.03.2005
Veröffentlichungstag im Patentblatt 21.04.2005
IPC-Hauptklasse A01N 47/34
IPC-Nebenklasse A01N 37/44   

Beschreibung[en]

The present invention relates to the use of hydrazine derivatives of formula I:

wherein
R1
represents hydrogen or C1-C6 alkyl;
R2 and R3
which may be same or different, Represent hydrogen, hydroxy, C1-C6 alkoxy, C1-C6 alkylcarbonyl or phenylcarbonyl;
R4
represents hydrogen or C1-C6 alkyl;
X
represents 1 to 5 same or different substituents selected from the group hydrogen, halogen, C1-C6 alkyl and C1-C6 haloalkyl;
Y
represents 1 to 5 same or different substituents selected from nitro and cyano;
Z
represents halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonal; and
W
represents oxygen or sulfur.
for combating pests selected from the Isoptera, Hymenoptera, Orthoptera and Psocoptera orders.

Related Art

The hydrazine derivatives represented by the formula (I) are known compounds disclosed in JP-A-5-4958, JP-A-5-17428, JP-A-5-32603, JP-A-5-262712, etc. In these patents it is described that these derivatives have an insecticidal activity as agrihorticultural insecticides against LEPIDOPTERA such as diamondback moth, rice leafroller, etc., HEMIPTERA such as tea green leafhopper, pear lace bug, etc., COLEOPTERA such as twenty-eightspotted ladybird, maize weevil, etc., DIPTERA such as melon fly, house fly, house mosquito, etc., and TYLENCHIDA such as coffee rootlesion nematode, root-knot nematode, etc.

Any of these patent gazettes, however, does neither describe nor suggest that said hydrazine derivatives have a marked insecticidal effect against ISOPTERA such as formosan subterranean termite, kolbe, etc., HYMENOPTERA such as cabbage sawfly, Carpenter ant, etc., ORTHOPTERA such as Japanese cockroach, field cricket, rice grasshopper, etc., and PSOCOPTERA such as large pale booklouse, etc.

It is known that hydrazine derivatives which differ from compounds (I) by a substitution in the phenyl ring moiety are suitable for the use against Isoptera, Hymenoptera and Orthoptera (WO-9206076) or against ant and termites (EP-A-05001 11).

Summary of the Invention

The present invention provides a new method for especially controlling ants doing harm to the wooden materials constituting houses, furniture, etc. or crops and human being. It has been found that the hydrazine derivatives of formula I have a marked insecticidal effect on pests from the Isoptera, Hymenoptera, Orthoptera, and Psocoptera orders, especially upon termites and ants.

The invention also relates to the use of compounds of formula I as defined above for protecting wooden materials against pests from the Rhinotermitidae, Termitidae, Kalotermitidae, and Termopsidae family.

It is an object of the present invention to provide a method for combating pests from the Isoptera, Hymenoptera, Orthoptera, and Psocoptera orders.

It is also an object of the invention to provide a method for protecting wooden materials against pests from the Rhinotermitidae, Termitidae, Kalotermitidae, and Termopsidae family.

We have found that this object is achieved by applying the compounds (I) defined at the outset for combating the pests as defined above.

The compounds of formula I can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as shrines, temples, houses, outhouses, factories, etc. from ants such as termites, and for controlling ants doing harm to crops or human being.

In the definition of formula (I) shown above, the term "halogen" means chlorine, bromine, iodine and fluorine; the term "C1-C6-alkyl" means a straight or branched chain alkyl group having 1 to 6 carbon atoms; and the term "C1-C6-haloalkyl" means an alkyl group having 1 to 6 carbon atoms substituted with at least one, same or different halogen atoms.

Preferable examples of each substituent of the hydrazine derivatives of formula (I) are the compounds wherein W is oxygen, X is trifluoromethyl, Y is cyano, Z is trifluoromethoxy, and each of R1, R2, R3 and R4 is simultaneously hydrogen atom.

More preferable examples are compounds of formula I wherein X is substituted on the 3-position, and Y is substituted on the 4-position of the phenyl ring.

Most preferable example is the hydrazine derivative represented by the formula I, wherein each of R1, R2, R3 and R4 is simultaneously hydrogen, X is trifluoromethyl substituted on the 3-position of the phenyl ring, Y is cyano substituted on the 4-position of the phenyl ring, and Z is trifluoromethoxy group.

Typical examples of the hydrazine derivative represented by formula (I) used according to the invention are shown in Table 1, but the present invention is by no means limited to the compounds exemplified herein.

The compounds of formula I exhibit a markedly high killing effect at a low dosage upon all the termites doing harm to houses, construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables, for example, RHINOTERMITIDAE including Coptotermes formosanus Shiraki, Reticulitermes speratus (Kolbe), Reticulitermes hesperus which inhabits the North America, Reticulitermes tibialis, Reticulitermes flavipes, Reticulitermes lucifugus which inhabits the shore of the Mediterranean, Reticulitermes santonensis, Incisitermes minor (Hagen), TERMITIDAE including Odontotermes formosanus (Shiraki), KALOTERMITIDAE including Cryptotermes domesticus (Haviland), TERMOPSIDAE including Hodotermopsis japonica (Holmgren), etc.

Further, the compounds of formula I exhibit a markedly high killing effect at a low dosage upon all the ants doing harm to crops, or to human being when the ants invade into houses and public facilities such as parks, for example, FORMICIDAE including Monomorium pharaonis Linne, Monomorium nipponense Wheelex, Camponotus kiusiuensis Santschi, Formica japonica Motschulsky, Lasius fuliginosus (Latreille), Solenopsis richteri, Solenopsis invicta, Solenopsis geminata (Fireant), etc.

For using the hydrazine derivatives of formula I for combating pests selected from the Isoptera, Hymenoptera, Orthoptera, and Psocoptera orders according to the invention, they are formulated with a proper solid carrier and/or liquid carrier. If necessary, they are formulated with auxiliaries in a proper proportion according to the conventional recipe of formulation, and homogenized together with the carrier by the method of dissolution, suspension, mixing, impregnation, adsorption or adhesion, so as to be made it into an appropriate preparation form such as oily solution, emulsifiable concentrate, solubilized concentrate, dust, granule, wettable powder, aerosol, fumigant, flowable preparation or the like. It is also possible to form compounds of formula I into a bait preparation by compounding it with a bait containing an attractant or the like.

As the solid carrier used in the present invention, there can be exemplified clays such as kaolin, bentonite, acid clay and the like; talcs such as talc, pyrophillite and the like; silica materials such as diatomaceous earth, siliceous sand, mica, synthetic silicate, synthetic high-dispersion silica and the like; and inorganic mineral powders such as pumice, sand and the like; organic matters such as pieces of wood, chips of pulp wood, grain flour, sugars and the like. As the liquid carrier, there can be exemplified alcohols such as methyl alcohol, ethyl alcohol, ethylene glycol and the like; ketones such as acetone, methyl ethyl ketone, cyclohexanone and the like; ethers such as ethyl ether, dioxane, tetrahydrofuran, Cellosolves and the like; aliphatic hydrocarbons such as light oil, kerosene and the like; aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, cyclohexanone, methylnaphthalene and the like; and halogenated hydrocarbons such as chloroform, carbon tetrachloride, chlorobenzene and the like. These solid and liquid carriers may be used either alone or in the form of a mixture.

As the auxiliaries which can be used in the present invention, surfactants, dispersants, sticking agents, etc. can be referred to. As the surfactants, there can be exemplified polyoxyethylene alkylaryl ethers, polyoxyethylene sorbitan monolaurates, alkylaryl sorbitan monolaurates, alkylbenzesulfonates, alkylnaphthalene-sulfonates, ligninsulfonates, higher alcohol sulfuric ester salts, etc. These surfactants may be used either alone or in the form of a mixture.

As the dispersants or sticking agents, for example, casein, gelatin, starch, alginic acid, carboxymethyl cellulose, agar, polyvinyl alcohol, turpentine oil, etc. can be used according to the need.

Compounds of formula I of the present invention are applied not only to the surrounding soil surface or into the under-floor soil in order to protect wooden materials such as trees, board fences, sleepers, etc. and structures such as shrines, temples, houses, outhouses, factories, etc., but it can also be applied to lumbered articles such as surfaces of the under-floor concrete, alcove posts, beams, plywoods, furniture, etc., wooden articles such as particle boards, half boards, etc. and vinyl articles such as coated electric wires, vinyl sheets, heat insulating material such as styrene foams, etc. In case of application against ants doing harm to crops or human beings, the hydrazine derivatives of the present invention is applied to the crops or the surrounding soil, or is directly applied to the nest of ants or the like.

The present invention is not limited to the embodiments mentioned above, but it also includes the embodiments of applying the hydrazine derivatives of the invention preventively to places at which occurrence of ants is expected.

In applying compounds of formula I according to the present invention, the dosage may be appropriately selected from the ranges property chosen. In case of application to wooden materials, the quantity of active ingredient ranges from 0,1 to 50 g per m2; and in case of soil treatment or application to the nests, the quantity of active ingredient ranges from 1 to 500 g per m2.

Examples

Next, typical examples and test example of formulations are presented below. The invention is by no means limited to these examples.

In the examples, "parts" are by weight. Formulation Example 1 Each hydrazine derivative listed in Table 1 20 parts Xylene 80 parts

The ingredients mentioned above were made into a uniform solution to obtain an oily solution. Formulation Example 2 Each hydrazine derivative listed in Table 1 10 parts Polyoxyethylene styrylphenyl ether 10 parts Cyclohexanone 80 parts

The ingredients mentioned above were uniformly mixed and dissolved together to obtain an emulsifiable concentrate. Formulation Example 3 Each hydrazine derivative listed in Table 1 10 parts Sodium alkylbenzenesulfonate 2 parts White carbon 10 parts Clay 78 parts

The ingredients mentioned above were uniformly mixed and pulverized to obtain a wettable powder. Formulation Example 4 Each hydrazine derivative listed in Table 1 8 parts Cyclohexanone 4 parts Mixture of polyoxyethylene nonylphenyl ether and alkylbenzenesulfonic acid 3 parts

A granular composition was prepared by uniformly mixing and dissolving together the ingredients mentioned above, and spraying the resulting solution onto 85 parts of granular pumice, followed by drying.

Test Example 1

A filer paper was spread in a glass dish having a diameter of 9 cm, onto which was dropped 1 ml of a 500 ppm solution of compounds of formula I. Then, the filter paper was inoculated with Coptotermes formosanus Shiraki.

Seven days after the inoculation, percentage of dead insects was investigated, from which mortality was calculated. The results were evaluated according to the following criterion. The test was carried out with triplicate group of 10 insects. Criterion Mortality (%) A 100 B 99-90 C 89-80 D 79-50

The results are summarized in Table 2: Compound No. Termite-killing effect Compound No. Termite-killing effect 5 A 30 A 6 A 35 A 7 A 36 B 8 C 37 A 9 B 40 D 10 A 41 A 11 A 44 C 12 A 45 A 13 A 55 A 14 A 56 A 17 A 62 A 18 A 63 A 19 A 76 A 20 A 77 A 21 A 78 A 22 B 79 B 23 A 80 A 26 A 81 A 27 A 82 B 28 C 83 D 29 C

Test Example 2

Compounds of formula I were applied to nests (ant hill) of fireant (Solenopsis geminata) with drench treatment, in terms of 1 g of the active ingredient per one nest. 14 days after the treatment, the activity of the nests was evaluated according to the following criterion. The test was carried out with one block per one nest. Criterion Effect A Nest is completely destructed or activity of the nest is extremely low. B Activity of the nest is exhibited. C High activity of the nest is exhibited. D Activity of the nest is extremely high.

As a result of the test, Compound No. 44 of the present invention exhibited the effect "A".


Anspruch[de]
  1. Verwendung für die Bekämpfung von Schädlingen aus den Ordnungen Isoptera, Hymenoptera, Orthoptera und Psocoptera durch Ausbringung eines Hydrazinderivats, das der Formel I entspricht:
    in der
    R1
    Wasserstoff oder C1-C6-Alkyl bedeutet;
    R2 und R3,
    die gleich oder unterschiedlich sein können, Wasserstoff, Hydroxy, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Alkylcarbonyl oder Phenylcarbonyl bedeuten;
    R4
    Wasserstoff oder C1-C6-Alkyl bedeutet;
    X
    1 bis 5 gleiche oder unterschiedliche Substituenten aus der Gruppe Wasserstoff, Halogen, C1-C6-Alkyl und C1-C6-Halogenalkyl bedeutet;
    Y
    1 bis 5 gleiche oder unterschiedliche Substituenten aus der Reihe Nitro und Cyano bedeutet;
    Z
    Halogen, Cyano, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Halogenalkylthio, C1-C6-Halogenalkylsulfinyl oder C1-C6-Halogenalkylsulfonyl bedeutet; und
    W
    Sauerstoff oder Schwefel bedeutet.
  2. Ausbringung nach Anspruch 1, wobei
    R1, R2, R3 und R4
    Wasserstoff bedeuten;
    X
    Trifluormethyl bedeutet;
    Y
    Cyano bedeutet;
    Z
    Trifluormethoxy bedeutet; und
    W
    Sauerstoff bedeutet.
  3. Verwendung von Hydrazinderivaten nach Anspruch 1 oder 2, wobei es sich bei den Schädlingen um Ameisen oder Termiten handelt.
  4. Verwendung von Hydrazinderivaten nach Anspruch 1 oder 2 für den Schutz von Häusern, Baustoffen, Möbeln, Leder, Fasern, Vinylartikeln, elektrischen Drähten oder Kabeln gegen Schädlinge aus den Familien Rhinotermitidae, Termitidae, Kalotermitidae und Termopsidae.
  5. Verwendung von Hydrazinderivaten nach Anspruch 1 oder 2 für die Bekämpfung von Schädlingen aus der Familie der Formicidae.
  6. Verwendung von Hydrazinderivaten nach Anspruch 5, wobei das Hydrazinderivat auf die Kulturen, auf den umgebenden Boden oder auf das Nest der Schädlinge ausgebracht wird.
  7. Verfahren für die Bekämpfung von Schädlingen aus den Familien Rhinotermitidae, Termitidae, Kalotermitidae und Termopsidae durch Ausbringung von 0,1 bis 50 g/m2 eines Hydrazinderivats der Formel I nach Anspruch 1 oder 2 auf Holzmaterial.
  8. Verfahren für die Bekämpfung von Schädlingen aus der Familie Formicidae durch Ausbringung von 1 bis 500 g/m2 eines Hydrazinderivats der Formel I nach Anspruch 1 oder 2 auf den Boden, der Kulturen umgibt, oder auf das Nest der Schädlinge.
Anspruch[en]
  1. A use for combating pests selected from the Isoptera, Hymenoptera, Orthoptera, and Psocoptera orders by applying a hydrazine derivative represented by formula I:
    wherein
    R1
    represents hydrogen or C1-C6 alkyl;
    R2 and R3,
    which may be same or different,

    represent hydrogen, hydroxy, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 alkylcarbonyl or phenylcarbonyl;
    R4
    represents hydrogen or C1-C6 alkyl;
    X
    represents 1 to 5 same or different substituents selected from the group hydrogen, halogen, C1-C6 alkyl and C1-C6 haloalkyl;
    Y
    represents 1 to 5 same or different substituents selected from nitro and cyano;
    Z
    represents halogen, cyano, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl or C1-C6 haloalkylsulfonyl; and
    W
    represents oxygen or sulfur.
  2. The use according to claim 1 wherein
    R1, R2, R3, and R4
    represent hydrogen;
    X
    represents trifluoromethyl;
    Y
    represents cyano;
    Z
    represents trifluoromethoxy; and
    W
    represents oxygen.
  3. The use of hydrazine derivatives as defined in claims 1 or 2 wherein the pests are ants or termites.
  4. The use of hydrazine derivatives as defined in claims 1 or 2 for protecting houses, construction materials, furniture, leathers, fibers, vinyl articles, electric wires or cables-against pests from the Rhinotermitidae, Termitidae, Kalotermitidae, and Termopsidae families.
  5. The use of hydrazine derivatives as defined in claims 1 or 2 for the control of pests from the formicidae family.
  6. The use of hydrazine derivatives according to claim 5 wherein the hydrazine derivative is applied to the crops, to the surrounding soil, or to the nest of the pests.
  7. A method for the control of pests from the Rhinotermitidae, Termitidae, Kalotermitidae, and Termopsidae families by applying 0.1 to 50 g/m2 of a hydrazine derivative of formula I as defined in claims 1 or 2 to wooden materials.
  8. A method for the control of pests from the Formicidae family by applying 1 to 500 g/m2 of a hydrazine derivative of formula I as defined in claims 1 or 2 to the soil surrounding crops or to the nest of the pests.
Anspruch[fr]
  1. Utilisation, pour combattre des organismes nuisibles choisis dans les ordres des Isoptères, des Hyménoptères, des Orthoptères et des Psocoptères, de l'application d'un dérivé de l'hydrazine représenté par la formule I :
    dans laquelle
    R1
    représente un atome d'hydrogène ou un groupe alkyle en (C1-C6) ;
    R2 et R3,
    qui peuvent être identiques ou différents, représentent un atome d'hydrogène, un groupe hydroxy, un groupe alkyle en (C1-C6), un groupe alcoxy en (C1-C6), un groupe alkyle en (C1-C6)carbonyle ou un groupe phénylcarbonyle ;
    R4
    représente un atome d'hydrogène ou un groupe alkyle en (C1-C6) ;
    X
    représente 1 à 5 substituants identiques ou différents, choisis dans le groupe comprenant un atome d'hydrogène, un atome d'halogène, un groupe alkyle en (C1-C6) et un groupe halogénoalkyle en (C1-C6);
    Y
    représente 1 à 5 substituants identiques ou différents choisis parmi un groupe nitro et un groupe cyano ;
    Z
    représente un atome d'halogène, un groupe cyano, un groupe alkyle en (C1-C6), un groupe halogénoalkyle en (C1-C6), un groupe alcoxy en (C1-C6), un groupe halogénoalcoxy en (C1-C6), un groupe halogénoalkyle en (C1-C6)thio, un groupe halogénoalkyle en (C1-C6)sulfinyle ou un groupe halogénoalkyle en (C1-C6)sulfonyle ; et
    W
    représente un atome d'oxygène ou un atome de soufre.
  2. Utilisation d'un composé selon la revendication 1, dans lequel
    R1, R2, R3 et R4
    représentent un atome d'hydrogène ;
    X
    représente un groupe trifluorométhyle ;
    Y
    représente un groupe cyano ;
    Z
    représente un groupe trifluorométhoxy ; et
    W
    représente un atome d'oxygène.
  3. Utilisation de dérivés de l'hydrazine tels que définis selon les revendications 1 ou 2, dans laquelle les organismes nuisibles sont des fourmis ou des termites.
  4. Utilisation de dérivés de l'hydrazine, tels que définis dans les revendications 1 ou 2, pour protéger les habitations, les matériaux de construction, l'ameublement, les cuirs, les fibres, les articles en vinyle, les fils ou les câbles électriques contre les organismes nuisibles appartenant aux familles des Rhinotermitidés, des Termitidés, des Kalotermitidés et des Termopsidés.
  5. Utilisation de dérivés de l'hydrazine, tels que définis dans les revendications 1 ou 2, pour lutter contre les organismes nuisibles de la famille des Formicidés.
  6. Utilisation de dérivés de l'hydrazine selon la revendication 5, dans laquelle le dérivé de l'hydrazine est appliqué aux cultures, au sol environnant ou au nid des organismes nuisibles.
  7. Procédé de lutte contre les organismes nuisibles appartenant aux familles des Rhinotermitidés, des Termitidés, des Kalotermitidés et des Termopsidés par application aux matériaux en bois de 0,1 à 50 g/m2 d'un dérivé de l'hydrazine de formule I, tel que défini selon les revendications 1 ou 2.
  8. Procédé de lutte contre les organismes nuisibles de la famille des Formicidés par application de 1 à 500 g/m2 d'un dérivé de l'hydrazine de formule I, tel que défini selon les revendications 1 ou 2, au sol environnant les cultures ou au nid des organismes nuisibles.






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