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(11) EP 1 809 106 B1

(12) EUROPEAN PATENT SPECIFICATION

(45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A01N 47/34 (2006.01) A01N 47/40 (2006.01) 25.04.2012 Bulletin 2012/17 A01N 51/00 (2006.01)

(21) Application number: 05800100.9 (86) International application number: PCT/IL2005/001139 (22) Date of filing: 31.10.2005 (87) International publication number: WO 2006/048868 (11.05.2006 Gazette 2006/19)

(54) Use of a mixture of novaluron and oder acetamiprid for controlling in crops Verwendung einer Mischung aus Novaluron und Imidacloprid oder Acetamiprid zur Insektenbekämpfung in Zuchtpflanzen Utilisation d’un mélange de novaluron et d’imidacloprid ou d’acetamiprid pour la lutte contre les insectes dans les cultures

(84) Designated Contracting States: US-A- 6 001 858 US-A- 6 001 858 AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LI LT LU LV MC NL PL PT RO SE SI • DATABASECA [Online] CHEMICAL ABSTRACTS SK TR SERVICE, COLUMBUS, OHIO, US; MATTOS, MARCO ANTONIO A. ET AL: "Agrochemical (30) Priority: 04.11.2004 IL 16502104 strategies evaluation for the control of Bemisia argentifolii Bellows & Perring (Hemiptera: (43) Date of publication of application: Aleyrodidae) on tomatoes" XP002468799 25.07.2007 Bulletin 2007/30 retrieved from STN Database accession no. 2003: 159088 & PESTICIDAS , 12, 131-144 CODEN: (60) Divisional application: PTICEA; ISSN: 0103-7277, 2002, 10178570.7 / 2 258 194 • DATABASECA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; CHEN, (73) Proprietor: MAKHTESHIM CHEMICAL WORKS ZHANGYAN ET AL: "Emamectin benzoate- LIMITED hexaflumuron mixed synergistic " 84100 Beer Sheva (IL) XP002468800 retrieved from STN Database accession no. 2005:5596 & CN 1 480 040 A (72) Inventors: (FUJIANXINNONG DAZHENG BIOENGINEERING • BARAZANI, Avner CO LTD, PEOP. REP. CHINA FUJIAN) 10 March 84965 Omer (IL) 2004 (2004-03-10) • BARKAI, Jacob • DATABASECA [Online] CHEMICAL ABSTRACTS 79505 Moshav Nir Israel (IL) SERVICE, COLUMBUS, OHIO, US; MA, YUNSHENG ET AL: "Emamectin benzoate- (74) Representative: Modiano, Micaela Nadia et al containing compound insecticide" XP002468801 Modiano Josif Pisanty & Staub Ltd retrieved from STN Database accession no. 2004: Thierschstrasse 11 500833 & CN 1 399 884 A (WEN, PEIHONG, PEOP. 80538 München (DE) REP. CHINA; XU, BOYONG; CAO, TONGBO) 5 March 2003 (2003-03-05) (56) References cited: WO-A-99/18796 WO-A-99/18796 WO-A-99/25188 WO-A-2005/053394 WO-A-2005/053394 DE-A1- 4 409 040 DE-A1- 4 409 040 DE-A1- 4 436 268 DE-A1- 4 436 268 DE-A1- 19 548 874

Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 809 106 B1

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• DATABASECA [Online] CHEMICAL ABSTRACTS Remarks: SERVICE, COLUMBUS, OHIO, US; LI, PUCHAO: Thefile contains technical information submitted after "Compounded insecticide with the application was filed and not included in this benzoylphenylurea pesticide" XP002468802 specification retrieved from STN Database accession no. 2002: 278050 & CN 1 308 861 A (ANYANG FOREST CHEMICALS FACTORY, PEOP. REP. CHINA) 22 August 2001 (2001-08-22) • DATABASECA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; ZHANG, YESHENG: "Environmentally friendly insecticide for controlling cabbage moth and American fly" XP002468803 retrieved from STN Database accession no. 2001:681653 & CN 1 292 218 A (PEOP. REP. CHINA PEOP. REP. CHINA) 25 April 2001 (2001-04-25)

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Description immediate and long term action against insects. [0007] A further purpose of the present invention is to Field of the Invention provide a method for , particularly con- trol, which provides effective immediate action and ef- [0001] The present invention relates to the field of pes- 5 fective long term activity. ticidal compositions, particularly pesticidal composition [0008] Other objects of the invention will become ap- containing at least two pesticidal active ingredients for parent as the description proceeds. improved control of pests. Summary of the invention Background of the Invention 10 [0009] The present invention provides the use of an [0002] In the practice of pest control, particularly insect insecticidal composition comprising (a) at least one in- control, there are two main factors which determine the secticidal compound with effective knock-down action effectiveness of the treatment; 1) immediate action on selected from among group (A) consisting of imidacloprid the pests (known in the art as "knock-down action"), 2) 15 and acetamiprid, and (b) novaluron as insecticidal com- long term action (known also as "residual action"). Effec- pound with effective long-term action, for insect control tive knock- down include , organic in crops and locus thereof. Optionally, said insecticidal phosphoric acid esters, , imidacloprid, composition may further contain excipients and/or addi- acetamiprid and phenyl pyrazoles (). Effective tives and/or surface active agents long term insecticides include insect growth regulators 20 [0010] According to a further aspect of the present in- (IGR) of various types, e.g. chitin synthesis inhibitors. vention, there is provided a method for insect control Current methods for achieving the desired effect include comprising a method for insect control comprising apply- repeated treatments over time with insecticides which ing at least one insecticidal compound with effective have an effective knock- down action. The disadvantages knock-down actionselected from the group (A)consisting of repeated treatments are; a) the use of relatively large 25 of imidacloprid and acetamiprid and (b) novaluron as in- doses of insecticides over time, which may create envi- secticidal compound with effective long-term action to a ronmental problems, and b) there are certain periods crop or a locus thereof in need of insect control. within the life cycle of the crop when treatments with ef- fective knock-down insecticides are prohibited since they Detailed Description of a Preferred Embodiment of may be absorbed in the crop or damage the crop. Using 30 the Invention long term active insecticides may help in preventing re- peated treatments, but may not be effective against cer- [0011] The following description is illustrative of em- tain insects which have reached a certain developmental bodiments of the invention. The following description is stage in their life cycle. For example, the group of insec- not to be construed as limiting, it being understood that ticides known as insect growth regulators (IGR) which 35 the skilled person may carry out many obvious variations generally have effective long term action are almost in- to the invention. effective against adult insects due to the low knock- down [0012] Throughout the description, percentages of effect. components are by weight, unless specifically noted dif- [0003] Combination treatments of knock-down and ferently. The terms "benzoyl urea", "benzoylphenyl urea" long term insecticides have been reported. 40 U.S.and "BPU" as used throughout the specification are syn- 6,685,954 reports on the effectiveness of fipronil in com- onymous. bination with IGR of the juvenile hormone mimic group [0013] It has surprisingly been found that the combi- in the treatment of ectoparasites in mammals. However, nation of an insecticide with knock- down activity selected no publications were found which suggest such a com- from among the groups of pesticides known in the art as bination for other purposes which are non-veterinary pur- 45 neonicotinoids, nitromethylene-neonicotinoids and phe- poses. In other fields of applications such as in the filed nylpyrazoles denoted as group (A) comprising of imida- of plants and plant matter, issues of phytotoxicity must cloprid, acetamiprid, , , niten- be considered as well. pyram, , , abamectin, emamectin, [0004] WO 99/18796 discloses the use of a combina- emamectin benzoate and fipronil, with an IGR insecticide tion of a benzylurea compound with a further pesticide 50 selected from among the BPU group (B), provided a syn- such as chloronicotinyl insecticides for controlling pests. ergistic effect and effective insect control. [0005] Accordingly, there is a long felt need for an in- [0014] The long term IGR group of pesticides known secticidal composition and method of pest control which as BPU herein designated "group (B)" includes inter alia, will provide effective control of insects by providing ef- novaluron, , hexaflumuron, triflumuron, dif- fectiveknock- down andlong term action, without creating 55 lubenzuron, chlorfluazuron, , noviflumuron environmental, toxic, phytotoxic and ecotoxic problems. and teflubenzuron. Novaluron is used in the present in- [0006] It is therefore a purpose of the invention to pro- vention. vide an insecticidal composition which provides effective [0015] "Knock-down" pesticides herein designated

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"group (A)" include: acetamiprid, imidacloprid, thiameth- tera, Diptera, Thysanoptera, Orthoptera, Anoplura, Si- oxam, thiacloprid, , dinotefuran, clothianidin, phonaptera, Mallophaga, Thysanura, Isoptera, Psocop- abamectin, emamectin, emamectin benzoate and fipron- tera and Hymenoptera, as well as representatives of the il. Acetamiprid or imidacloprid are used in the present order Acarina of the familiesIxodidae, Argasidae, invention. 5 Tetranychidae and Dermanyssidae. [0016] According to a preferred embodiment of the [0024] In addition said method and composition are present invention there is provided the use of an insec- effective in controlling flies, e.g. Musca domestica, ter- ticidal composition comprising 0.1% to 60% of at least mites, cockroaches and mosquito larvae. The presently one knock down insecticide selected from among group claimed method and composition is also suitable for con- (A) consisting of imidacloprid and acetamiprid; and 0.5% 10 trolling plant-destructive feeding insects in ornamentals to 60% of novaluron as insecticidal compound with long- and crops of useful plants, especially in (e.g. term action. More preferably said composition contains against Spodoptera littoralis and Heliothis virescens) 10% to 50% of at least one insecticide selected from and in fruit and vegetables (e.g. againstLaspeyresia group (A) and 5 % to 15% of novaluron. pomonella, Cydia pomonella, Lithocolletis blancardella, [0017] The composition disclosed herein is formulated 15 Stigmella malella, Adoxophyes orana, Psylla piri, Cryp- in a manner which suits the specific application. Non- tophlebia leucotreta, , Cydia moles- limiting examples of suitable formulations are; emulsion ta, Anarsia lineatella, Leptinotarsa decemlineata and concentrates (EC), suspension concentrates (SC), water Epilachna varivestis), as well as for controlling several dispersible granules (WDG) and wettable powders (WP) species of mites, e.g., oleivora. and formulations suitable for oral, topical or injectable 20 [0025] The present method and composition are fur- veterinary formulations. ther effective for controlling ectoparasites such as Lucilia [0018] According to yet a further embodiment of the sericata, in domestic animals and productive livestock, compositions disclosed herein, there is provided a syn- e.g. by treating animals, cowsheds, barns, stables, pas- ergistic insecticidal composition comprising of at least tures and the like. one knock-down insecticide selected from among group 25 [0026] According to a particular embodiment of the (A) consisting of imidacloprid and acetamiprid; and no- present method, the pesticidal composition is used to valuron as insecticidal compound with long-term action, prepare a tank mix which is then applied via spraying to wherein the weight ratio between the group (A) insecti- the area, plant matter or crop needing treatment. The cide and novaluron is in the range of 1: 100 to 100: 1, more active ingredient concentration in the tank mix is adjusted preferably 1:50 to 50:1. 30 to the particular application, depending on agricultural or [0019] The present invention further provides method non-agricultural application, the crop and the pest. Al- for insect control, comprising of applying at least one in- though various methods of application may be employed secticidal compound with effective knock-down action as the skilled artisan may appreciate, spraying is the pre- selected from among group (A) consisting of imidacloprid ferred method of application. Various methods of appli- and acetamiprid; and novaluron as insecticidal com-35 cation can also be employed when necessary. For ex- pound with effective long-term action to a crop, agricul- ample, in field crops systemic application via an irrigation tural product, plant matter, animal or locale. The present system can be combined with foliar application. method is effective for insect control in agricultural, hor- [0027] According to a particular embodiment of the in- ticultural, insect control in ornamentals, seed treatment vention, separate application is employed wherein the and non-agricultural purposes, e.g. public health, storage 40 knock down and long term insecticides are applied sep- and domestic use and veterinary. arately. [0020] According to a preferred embodiment of the method of the present invention, the application of the insecticides is simultaneous, separate or sequential ap- Claims plication. 45 [0021] According to a preferred embodiment of the 1. Use of an insecticidal composition comprising (a) at present method, the insecticidal composition is em- least one insecticidal compound with effective ployed for pest control. knock-down action selected from among group (A) [0022] According to specific embodiment of the meth- consisting of imidacloprid and acetamiprid, and (b) od of the present invention when applied to plant matter, 50 novaluron as insecticidal compound with effective the insecticides of group (A) are applied at a rate of 1g/ long-term action, for insect control in crops and locus hectar to 500g/hectar and novaluron is applied at a rate thereof. of 1g/hectar to 200g/hectar. Preferably, group (A) insec- ticides are applied at rate of 100g/hectar to 350g/hectar 2. A use according to claim 1 wherein said insecticidal and novaluron at a rate of 30g/hectar to 100g/hectar. 55 composition comprises 0.1% to 60% of at least one [0023] The present method and composition are par- insecticide from group (A) and 0.5% to 60% of no- ticularly effective for controlling insects of, inter alia, the valuron, preferably 10% to 50% of at least one in- orders Lepidoptera, Coleoptera, Homoptera, Heterop- secticide from group (A) and 5% to 15% of novaluron.

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3. A use according to claim 1 wherein the weight to 5. Ein Verfahren zur Insektenbekämpfung, das Folgen- weight ratio between the group (A) insecticides and des umfasst: Anwendung mindestens einer Insekti- novaluron is in the rangeof 1: 100 to 100:1, preferably zidverbindung mit wirksamer Knockdown-Aktivität, 1:50 to 50:1. gewählt aus der Gruppe (A) bestehend aus Imida- 5 cloprid und Acetamiprid und (b) Novaluron als Insek- 4. A use according to any of claims 1 to 3 wherein said tizidverbindung mit wirksamer Langzeitwirkung auf insecticidal composition further contains excipients eine Zuchtpflanze oder ein Gebiet davon, die/das and/or additives and/or surface active agents. Insektenbekämpfung benötigt.

5. A method for insect control comprising applying at 10 6. Ein Verfahren gemäß Anspruch 5, worin die Anwen- least one insecticidal compound with effective dung der Insektizide gleichzeitig, separat oder se- knock-down action selected from the group (A) con- quentiell ist. sisting of imidacloprid and acetamiprid and (b) no- valuron as insecticidal compound with effective long- 7. Ein Verfahren gemäß Anspruch 5, worin bei Anwen- term action to a crop or a locus thereof in need of 15 dung auf eine Zuchtpflanze oder ein Feld die Insek- insect control. tizide der Gruppe (A) mit einer Rate von 1g/Hektar bis 500g/Hektar angewandt werden und Novaluron 6. A method according to claim 5 wherein the applica- mit einer Rate von 1g/Hektar bis 200g/Hektar ange- tion of the insecticides is simultaneous, separate or wandt wird; vorzugsweise werden Insektizide der sequential. 20 Gruppe (A) mit einer Rate von 100g/ Hektar bis 350g/ Hektar und Novaluron mit einer Rate von 30g/ Hektar 7. A method according to claim 5 wherein when applied bis 100g/Hektar angewandt. to crop or field, the insecticides of group (A) are ap- plied at a rate of 1g/hectar to 500g/hectar and no- valuron is applied at a rate of 1g/hectar to 200g/hec- 25 Revendications tar, preferably, group (A) insecticides are applied at a rate of 100g/hectar to 350g/hectar and novaluron 1. Utilisation d’une composition insecticide, compre- at a rate of 30g/hectar to 100g/hectar. nant (a) au moins un composé insecticide ayant une action de choc efficace, sélectionné parmi le groupe 30 (A) composé d’imidacloprid et d’acétamipride, et (b) Patentansprüche du novaluron en tant que composé insecticide avec une action à long terme efficace, pour la suppression 1. Verwendung einer Insektizidzusammensetzung, die des insectes dans les cultures et leur emplacement Folgendes umfasst: (a) mindestens eine Insektizid- géographique. verbindung mit wirksamer Knockdown-Aktivität, ge- 35 wählt aus der Gruppe (A) bestehend aus Imidaclo- 2. Utilisation selon la revendication 1, dans laquelle la- prid und Acetamiprid und (b) Novaluron als Insekti- dite composition insecticide comprend de 0,1 % à zidverbindung mit wirksamer Langzeitwirkung, zur 60 % d’au moins un insecticide issu du groupe (A) Insektenbekämpfung in Zuchtpflanzen und Gebiet et de 0,5 % à 60 % de novaluron, de préférence de davon. 40 10 % à 50 % d’au moins un insecticide issu du groupe (A) et de 5 % à 15 % de novaluron. 2. Eine Verwendung gemäß Anspruch 1, worin die In- sektizidzusammensetzung Folgendes umfasst: 3. Utilisation selon la revendication 1, dans laquelle le 0,1% bis 60% mindestens eines Insektizids aus der rapport des poids, entre les insecticides du groupe Gruppe (A) und 0,5% bis 60% Novaluron, vorzugs- 45 (A) et le novaluron, est dans la fourchette comprise weise 10% bis 50% mindestens eines Insektizids entre 1:100 et 100:1, de préférence entre 1:50 et 50: aus der Gruppe (A) und 5% bis 15% Novaluron. 1.

3. Eine Verwendung gemäß Anspruch 1, worin das Ge- 4. Utilisation selon l’une quelconque des revendica- wichtsverhältnis zwischen den Insektiziden aus der 50 tions 1 à 3, dans laquelle ladite composition inserti- Gruppe (A) und Novaluron im Verhältnis von 1:100 cide contient en outre des excipients et/ou des ad- bis 100:1, vorzugsweise 1:50 bis 50:1, liegt. ditifs et/ou des agents tensioactifs.

4. Eine Verwendung gemäß einem beliebigen der An- 5. Procédé de suppression des insectes, comprenant sprüche 1 bis 3, worin die Insektizidzusammenset- 55 l’application d’au moins un composé ayant une ac- zung weiter Bindemittel und/oder Zusatzstoffe und/ tion de choc efficace, sélectionné parmi le groupe oder grenzflächenaktive Stoffe enthält. (A) composé d’imidacloprid et d’acétamipride, et (b) du novaluron en tant que composé insecticide avec

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une action à long terme efficace, pour la suppression des insectes dans les cultures et leur emplacement géographique

6. Procédé selon la revendication 5, dans lequel l’ap- 5 plication des insecticides est simultanée, séparée ou séquentielle.

7. Procédé selon la revendication 5, dans lequel, lors- qu’ils sont appliqués à une culture ou à un champ, 10 les insecticides du groupe (A) sont appliqués à un dosage de 1 g/hectare à 500 g/hectare et le novalu- ron est appliqué à un dosage de 1 g/hectare à 200 g/hectare, de préférence les insecticides du groupe (A) sont appliqués à un dosage de 100 g/hectare à 15 350 g/hectare et le novaluron est appliqué à un do- sage de 30 g/hectare à 100 g/hectare.

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REFERENCES CITED IN THE DESCRIPTION

This list of references cited by the applicant is for the reader’s convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description

• US 6685954 B [0003] • WO 9918796 A [0004]

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