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Dokumentenidentifikation EP0962138 26.04.2007
EP-Veröffentlichungsnummer 0000962138
Titel Verfahren zur Schädlingsbekämpfung
Anmelder BASF Agro B.V., Arnhem (NL)-Wädenswil-Branch, Wädenswil, CH
Erfinder Lankford, William Timothy, Ongar, Essex, CM5 0HW, GB;
Parsons, Richard, Manningtree, Essex, CO11 2NF, GB
Vertreter derzeit kein Vertreter bestellt
DE-Aktenzeichen 69837320
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 07.05.1998
EP-Aktenzeichen 983035627
EP-Offenlegungsdatum 08.12.1999
EP date of grant 14.03.2007
Veröffentlichungstag im Patentblatt 26.04.2007
IPC-Hauptklasse A01N 47/02(2006.01)A, F, I, 20051017, B, H, EP
IPC-Nebenklasse A01N 43/56(2006.01)A, L, I, 20051017, B, H, EP   

Beschreibung[en]

The present invention relates to a new pesticidal method for the control of weevils, e.g. Otiorynchus sulcatus.

It is presently known that weevils, such as Otiorynchus sulcatus (also known as Black Vine Weevil) are destructive pests in agriculture and horticulture. The insects may inhabit potted plants which are available at commercial horticultural markets. A problem to overcome in the control of these insects in horticultural markets is actually detecting the presence of the larvae of the insects. Although detection of adults may be readily done by observing feeding damage on the leaves, damage by larvae is particularly insidious and difficult to detect because the larvae damage the plants by destroying the roots. Thus by the time damage is detected the plant may not have a reasonable chance to recover after treatment.

An object of the invention is the control of weevils, such as Otiorynchus sulcatus and others mentioned hereinafter.

Another object of the invention is the prevention of damage by weevils, such as Otiorynchus sulcatus, to plants, e.g. ornamental plants.

These objects are met in whole or in part by the instant invention.

The present invention provides a method of providing long term protection of a plant, eg an ornamental plant, a soft fruit plant (e.g. strawberry or raspberry) or pine, from weevils which method comprises incorporating in a growing medium in which the plant is growing or is to be grown an insecticidally effective amount of a 1-arylpyrazole of formula (I): wherein:

  • R1 is CN or methyl or a halogen atom;
  • R2 is S(O)nR3 or 4,5-dicyanoimidazol-2-yl or haloalkyl;
  • R3 is alkyl or haloalkyl;
  • R4 is selected from the group consisting of hydrogen, halogen, -NR5R6, -C(O)OR7, -S(O)mR7, alkyl, haloalkyl, -OR8, -N=C(R9)(R10) and -C(O)alkyl;
  • R5 and R6 are independently selected from a hydrogen atom, alkyl, haloalkyl, -C(O)alkyl, -C(O)OR7, -S(O)rCF3; or R5 and R6 form together a divalent alkylene radical which may be interrupted by one or more heteroatoms, preferably selected from oxygen, nitrogen and sulfur;
  • R7 is selected from alkyl and haloalkyl;
  • R8 is selected from alkyl, haloalkyl and hydrogen;
  • R9 is selected from hydrogen and alkyl;
  • R10 is selected from phenyl and heteroaryl each of which is unsubstituted or substituted by one or more hydroxy, halogen, -O-alkyl, -S-alkyl, cyano, or alkyl or combinations thereof;
  • X is selected from nitrogen and -C-R12;
  • R11 and R12 are independently selected from halogen, hydrogen, CN and NO2;
  • R13 is selected from halogen, haloalkyl, haloalkoxy, -S(O)qCF3 and -SF5;
  • m, n, q, r are independently selected from 0, 1, and 2;
  • provided that when R1 is methyl, R3 is haloalkyl, R4 is NH2, R11 is Cl, R13 is CF3, and X is N and provided that when R2 is 4,5-dicyanoimidazol-2-yl, R4 is Cl, R11 is Cl, R13 is CF3, and X is =C-Cl.

The alkyl and alkoxy groups and moieties thereof of the formula (I) are preferably lower alkyl and alkoxy groups, that is, groups having one to six carbon atoms. The haloalkyl and haloalkoxy groups likewise preferably have one to four carbon atoms. The haloalkyl and haloalkoxy groups can bear one or more halogen atoms; preferred groups of this type include -CF3 and -OCF3. It shall be understood that the ring formed by the divalent alkylene radical represented by R5 and R6 and including the nitrogen atom to which R5 and R6 are attached is generally a 5, 6, or 7-membered ring. When R10 is heteroaryl, it is preferably pyridyl, most preferably 2-pyridyl. It will be understood that the 1-arylpyrazoles of formula (I) include enantiomers and/or diastereomers thereof and mixtures thereof.

A preferred group of 1-arylpyrazoles for use in the present invention are those of formula (I) with one or more of the following features wherein:

  • R1 is CN;
  • R4 is -NR5R6;
  • R5 and R6 are independently selected from the hydrogen atom, alkyl, haloalkyl, C(O)alkyl, C(O)OR7;
  • X is C-R12; or
  • R13 is selected from a halogen atom, haloalkyl, haloalkoxy, and -SF5.

Another preferred group of 1-arylpyrazoles of formula (I) for use in the present invention is that wherein:

  • R1 is CN;
  • R3 is a haloalkyl radical;
  • R4 is NH2;
  • X is C-R12;
  • R11 and R12 represent, independently of one another, a halogen atom; and
  • R13 is a haloalkyl radical.

A most preferred compound is 5-amino-1-(2,6-dichloro 4-trifluoromethyl phenyl) 4-trifluoromethylsulfinyl-3-cyanopyrazole, hereafter designated as compound (A).

Compounds of formula (I) may be prepared according to known processes, for example as described in International Patent Publications WO 87/3781, 93/6089, and 94/21606 as well as in European Patent Applications 295117, 403300, 385809 or 679650, German Patent Publication 19511269 and United States Patents 5232940 and 5236938 or other process according to the knowledge of a man skilled in the art of chemical synthesis, which is deemed to include Chemical Abstracts and the literature referred to therein, Compositions comprising the compounds of formula (I) may also be prepared according to the teaching of the same prior art or similar publications.

The weevils may be of the Otiorynchus or Hylobius family, e.g. Otiorynchus sulcatus, Otiorynchus ovatus (European strawberry) weevil, Otiorynchus singularis which attack soft fruit plants (e.g. strawberry and raspberry) and Hylobius abietis (pine weevil).

By the term "growing medium" is meant a substance in which, for example, the plant or the seed from which it grows may germinate and develop or into which it may be translated. Generally growing medium comprises compost, peat or potting soil. To facilitate even distribution of the 1-arylpyrazole in the growing medium, it may be applied to one or more components e.g. sand, perlite or water-retaining granules of the growing medium before that component is incorporated into the growing medium. The content of 1-arylpyrazole in the treated component may be adjusted to provide the desired final concentration after mixing all the components of the growing medium.

The 1-arylpyrazole may be used in conjunction with other active ingredients, for example a plant feed or plant growth regulator. Compositions comprising a plant feed or plant growth regulator, a 1-arylpyrazole of general formula (I) and, optionally, a carrier and/or a surface active agent may also be used in the method of the invention.

The amount of the 1-arylpyrazole is from 0.01 g/m3 to 10 g/m3 of 1-arylpyrazole per volume of growing medium, preferably from 0.2 g/m3 to 5 g/m3, more preferably from 0.25 to 1 g/m3.

The method of the invention is preferably applied to plants grown in containers, for example pots, nets or other flexible material which contains the growing medium.

The incorporation of the 1-arylpyrazole is generally effected by a suitable means known to those skilled in the art. It is generally preferred to apply the 1-arylpyrazole as a particulate solid composition or a liquid composition to the growing medium. It is more preferable to apply the 1-arylpyrazole as a particulate solid composition in order to minimize the effective amount and more evenly distribute the active ingredient in the growing medium.

In general the method of the instant invention is used preventatively: that is, the application of the 1-arylpyrazole is used to prevent or reduce attack by weevils such as Otiorynchus sulcatus on a plant. However, the invention may also be used curatively in that a planting medium infested with weevils such as Otiorynchus sulcatus or others mentioned above may be treated to kill a substantial majority of the insects after the plant has been affected. Generally in a curative treatment, it is preferred to apply the 1-arylpyrazole as a liquid composition to penetrate the planting medium quickly.

The method of the invention may be used to provide long-term protection for plants, including ornamental plants, from weevils such as Otiorynchus sulcatus. Generally, the method of the invention provides protection of from 0.1 years to 5 years, preferably from 0.3 years to 3 years, most preferably from 0.5 years to 2 years.

The following Examples illustrate the invention:

Example 1:

In a twenty-replicate test, Compound A was incorporated in compost by mixing a 2% w/w granule with the compost (Klasmann Substrat 2 (Peat based) ) using a small mechanical mixer. Plants of Thuya plicata Atrovirens were potted in the compost and allowed to grow for two months and then about 15 eggs of Otiorynchus sulcatus were added to the soil and covered with a small layer of compost. As a comparison, some compost was untreated and other compost was treated with the standard chlorpyrifos in the form of the commercial product suSCon Green®. After 27 days the soil was reinfested with 15 more eggs. The plant pots were enclosed such that the plants were exposed to light and the adult beetles which emerged could not escape.

Of the twenty replicates of each test, five were assessed after 6 months and fifteen were assessed after 18 months for numbers of larvae and adults. After 6 months the following results were observed: Compound Dose g/m3 Total # larvae Number per pot % Control Untreated 0 31 3.1 0 A 2.5 0 0 100 A 5 0 0 100 A 7.5 0 0 100 A 15 0 0 100 Chlorpyrifos 75 4 0.8 87

The following results were obtained after 18 months: Compound Dose g/m3 Total Dead Plants % Survival of Plants Total # larvae Number per pot % Control Untreated 0 7 72 51 3.1 0 A 2.5 0 100 0 0 100 A 5 0 100 0 0 100 A 7.5 0 100 0 0 100 A 15 0 100 0 0 100 Chlorpyrifos 75 0 100 47 3.1 0

Example 2

In 20-replicate tests, Fuchsia triphylla hybrid cv. Koralle was infested with 15 eggs per pot of vine weevil. Compound A in the form of an 80% water dispersible granule (Regent 800 WG) was suspended in water and added to each pot at the indicated rate per surface area of the pot at various dilutions. After 6 months, the trials were assessed. Compound A protected the plants substantially better than the commercial standard fonofos in a curative treatment. Drench Treatments Trt. No. Dose mg m-2 in litre Total no. of larvae Number per pot Control 1 Untreated Control 44 2.2 2 REGENT 800WG 1.25 5 25 1.25 43% 3 REGENT 800WG 1.25 10 30 1.5 32% 4 REGENT 800WG 1.25 20 12 0.6 73% 5 REGENT 800WG 2.5 5 10 0.5 77% 6 REGENT 800WG 2.5 10 18 0.9 59% 7 REGENT 800WG 2.5 20 10 0.5 77% 8 REGENT 800WG 5 5 8 0.4 82% 9 REGENT 800WG 5 10 11 0.55 75% 10 REGENT 80OWG 5 20 15 0.75 66% 11 REGENT 80OWG 10 10 5 0.25 89% 12 Cudgel ml (fonofos) 2.5 10 32 1.6 27%


Anspruch[de]
Verfahren der Bereitstellung von langfristigem Schutz einer Pflanze vor Angriff durch Rüsselkäfer der Familie Otiorhynchus oder Hylobius, wobei das Verfahren das Einbringen von 1-Arylpyrazol der Formel (I): in ein Wachstumsmedium in einer Menge von 0,01 g/cm3 bis 10 g/m3 pro Volumen an dem Wachstumsmedium, in dem die Pflanze wächst oder wachsen soll, umfasst, worin: R1 CN oder Methyl oder ein Halogenatom ist; R2S(O)nR3 oder 4,5-Dicyanoimidazol-2-yl oder Halogenalkyl ist; R3 Alkyl oder Halogenalkyl ist; R4 ausgewählt ist aus der Gruppe bestehend aus Wasserstoff, Halogen, -NR5R6, -C(O)OR7, -S(O)mR7, Alkyl, Halogenalkyl, -OR8, -N=C(R9)(R10) und -C(O)-Alkyl; R5 und R6 unabhängig voneinander ausgewählt sind aus einem Wasserstoffatom, Alkyl, Halogenalkyl, -C(O)-Alkyl, -C(0)OR7, -S(O)rCF3; oder R5 und R6 zusammen ein zweiwertiges Alkylenradikal bilden, das durch ein oder mehrere Heteroatome unterbrochen sein kann, die vorzugsweise ausgewählt sind aus Sauerstoff, Stickstoff und Schwefel; R7 ausgewählt ist aus Alkyl und Halogenalkyl; R8 ausgewählt ist aus Alkyl, Halogenalkyl und Wasserstoff; R9 ausgewählt ist aus Wasserstoff und Alkyl; R10 ausgewählt ist aus Phenyl und Heteroaryl, die jeweils nicht-substituiert oder mit einem oder mehreren aus Hydroxyl, Halogen, -O-Alkyl, -S-Alkyl, Cyano oder Alkyl oder deren Kombinationen substituiert sind; X ausgewählt ist aus Stickstoff und -C-R12; R11 und R12 unabhängig voneinander ausgewählt sind aus Halogen, Wasserstoff, CN und NO2; R13 ausgewählt ist aus Halogen, Halogenalkyl, Halogenalkoxy, -S(O)qCF3 und -SF5; m, n, q, r unabhängig voneinander ausgewählt sind aus 0, 1 und 2; vorausgesetzt, dass wenn R1 Methyl ist, R3 Halogenalkyl ist, R4 NH2 ist, R11 Cl ist, R13 CF3 ist und X N ist, und vorausgesetzt, dass wenn R2 4,5-Dicyanoimidazol-2-yl ist, R4 Cl ist, R11 Cl ist, R13 CF3 ist und X =C-Cl ist. Verfahren gemäß Anspruch 1, wobei der Rüsselkäfer Otiorhynchus sulcatus, ovatus oder singularis, oder Hylobius abietis ist. Verfahren gemäß Anspruch 1 oder 2, wobei das 1-Arylpyrazol in einer Menge von 0,2 g/m3 bis 5 g/m3 an aktivem Bestandteil pro Volumen an dem Wachstumsmedium angewendet wird. Verfahren gemäß einem der vorhergehenden Ansprüche, wobei das Wachstumsmedium Kompost, Torf oder Blumenerde umfasst. Verfahren gemäß einem der vorhergehenden Ansprüche, wobei das 1-Arylpyrazol als eine partikuläre feste Zusammensetzung dem Wachstumsmedium beigegeben wird. Verfahren gemäß einem der Ansprüche 1 bis 4, wobei das 1-Arylpyrazol als eine flüssige Zusammensetzung dem Wachstumsmedium beigegeben wird. Verfahren gemäß einem der vorhergehenden Ansprüche, wobei das 1- Arylpyrazol 5-Amino-1-(2,6-dichlor-4-trifluormethylphenyl)-4-trifluormethylsulfinyl-3-cyanopyrazol ist.
Anspruch[en]
A method of providing long-term protection of a plant from attack by weevil of the Otiorynchus or Hylobius family which method comprises incorporating in a growing medium, at a rate of from 0.01 g/m3 to 10 g/m3 per volume of growing medium in which the plant is growing or is to be grown, a 1-arylpyrazole of formula (I): wherein: R1 is CN or methyl or a halogen atom; R2 is S(O)nR3 or 4,5-dicyanoimidazol-2-yl or haloalkyl; R3 is alkyl or haloalkyl; R4 is selected from the group consisting of hydrogen, halogen, -NR5R6, -C(O)OR7, -S(O)mR7, alkyl, haloalkyl, -OR8,-N=C(R9)(R10) and -C(O)alkyl; R5 and R6 are independently selected from a hydrogen atom, alkyl, haloalkyl, -C(O)alkyl, -C(O)OR7, -S(O)rCF3; or R5 and R6 form together a divalent alkylene radical which may be interrupted by one or more heteroatoms, preferably selected from oxygen, nitrogen and sulfur; R7 is selected from alkyl and haloalkyl; R8 is selected from alkyl, haloalkyl and hydrogen; R9 is selected from hydrogen and alkyl; R10 is selected from phenyl and heteroaryl each of which is unsubstituted or substituted by one or more hydroxy, halogen, -O-alkyl, -S-alkyl, cyano, or alkyl or combinations thereof; X is selected from nitrogen and -C-R12; R11 and R12 are independently selected from halogen, hydrogen, CN and NO2; R13 is selected from halogen, haloalkyl, haloalkoxy, -S(O)qCF3 and -SF5; m, n, q, r are independently selected from 0, 1, and 2; provided that when R1 is methyl, R3 is haloalkyl, R4 is NH2, R11 is Cl, R13 is CF3, and X is N and provided that when R2 is 4,5-dicyanoimidazol-2-yl, R4 is Cl, R11 is Cl, R13 is CF3, and X is =C-Cl. A method according to claim 1 wherein the weevil is Otiorynchus sulcatus, ovatus or singularis, or Hylobius abietis. A method according to claim 1 or 2 wherein the 1-arylpyrazole is applied at from 0.2 g/m3 to 5 g/m3 of active ingredient per volume of growing medium. A method according to any one of the preceding claims wherein the growing medium comprises compost, peat or potting soil. A method according to any one of the preceding claims wherein the 1-arylpyrazole is applied as a particulate solid composition to the growing medium. A method according to any one of claims 1 to 4 wherein the 1-arylpyrazole is applied as a liquid composition to the growing medium. A method according to any one of the preceding claims wherein the 1-arylpyrazole is 5-amino-1-(2,6-dichloro 4-trifluoromethyl phenyl) 4-trifluoromethylsulfinyl-3-cyanopyrazole.
Anspruch[fr]
Procédé pour conférer à une plante une protection de longue durée contre l'attaque par un charançon du genre Otiorynchus ou Hylobius, procédé qui comprend l'incorporation à un milieu de croissance, à un taux de 0,01 g/m3 à 10 g/m3 par volume de milieu de croissance dans lequel la plante se développe ou est destinée à être cultivée, d'un 1-arylpyrazole de formule (I) : dans laquelle

R1 représente un groupe CN ou méthyle ou un atome d'halogène ;

R2 représente un groupe S(O)nR3 ou 4,5-dicyano-imidazole-2-yle ou halogénalkyle ;

R3 représente un groupe alkyle ou halogénalkyle ;

R4 est choisi dans le groupe consistant en un atome d'hydrogène, un atome d'halogène, des groupes -NR5R6, -C(O)OR7, -S(0)mR7, alkyle, halogénalkyle, -OR8, -N=C(R9)(R10) et -C(O)alkyle;

R5 et R6 sont choisis indépendamment entre un atome d'hydrogène, des groupes alkyle, halogénalkyle, -C (O) alkyle, -C(O)OR7, -S(O)rCF3 ; ou bien R5 et R6 forment conjointement un radical alkylène divalent qui peut être interrompu par un ou plusieurs hétéroatomes, choisis de préférence entre l'oxygène, l'azote et le soufre ;

R7 est choisi entre des groupes alkyle et halogénalkyle ;

R8 est choisi entre des groupes alkyle, halogénalkyle et un atome d'hydrogène;

R9 est choisi entre un atome d'hydrogène et un groupe alkyle ;

R10 est choisi entre des groupes phényle et hétéroaryle, chacun d'entre eux étant non substitué ou substitué avec un ou plusieurs substituants hydroxy, halogéno, -O-alkyle, -S-alkyle, cyano, alkyle ou leurs associations ;

X est choisi entre un atome d'azote et un groupe -C-R12;

R11 et R12 sont choisis indépendamment entre un atome d'hydrogène, un atome d'halogène, des groupes CN et NO2 ;

R13 est choisi entre un atome d'halogène, des groupes halogénalkyle, halogénalkoxy, -S(O)qCF3 et -SF5 ;

m, n, q et r sont choisis indépendamment entre 0, 1 et 2 ;

sous réserve que, lorsque R1 représente un groupe méthyle, R3 représente un groupe halogénalkyle, R4 représente un groupe NH2, R11 représente un groupe Cl, R13 représente un groupe CF3 et X représente N, et sous réserve que, lorsque R2 représente un groupe 4,5-dicyanoimidazole-2-yle, R4 représente un groupe Cl, R11 représente un groupe Cl, R13 représente un groupe CF3 et X représente un groupe =C-Cl.
Procédé suivant la revendication 1, dans lequel le charançon est Otiorynchus sulcatus, ovatus ou singularis, ou Hylobius abietis. Procédé suivant la revendication 1 ou 2, dans lequel le 1-arylpyrazole est appliqué à un taux de 0,2 g/m3 à 5 g/m3 d'ingrédient actif par volume de milieu de croissance. Procédé suivant l'une quelconque des revendications précédentes, dans lequel le milieu de croissance comprend du compost, de la tourbe ou de la terre pour mise en pot. Procédé suivant l'une quelconque des revendications précédentes, dans lequel le 1-arylpyrazole est appliqué sous forme d'une composition solide en particules au milieu de croissance. Procédé suivant l'une quelconque des revendications 1 à 4, dans lequel le 1-arylpyrazole est appliqué sous forme d'une composition liquide au milieu de croissance. Procédé suivant l'une quelconque des revendications précédentes, dans lequel le 1-arylpyrazole est le 5-amino-1-(2,6-dichloro-4-trifluorométhylphényl)4-trifluorométhylsulfinyl-3-cyanopyrazole.






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