NZ272296A

NZ272296A - Pesticidal composition of a carbonylurea derivative

Info

Publication number: NZ272296A
Application number: NZ272296A
Authority: NZ
Inventors: Claude Fluckiger; Robert Senn; Stephen Wilson Skillman
Original assignee: Novartis Ag
Priority date: 1994-06-09
Filing date: 1995-06-07
Publication date: 1997-11-24
Also published as: NL1000523C2; ZA954733B; HUT71254A; HU217531B; ES2114791A1; CH687732A5; ITMI951213A0; FR2720898B1; FR2720898A1; IT1279007B1; BR9502723A; KR100402907B1; ITMI951213A1; PT101719B; BE1008752A3; CN1120886A; CN1108749C; GR950100226A; PT101719A; ES2114791B1

Description

<div class="application article clearfix" id="description"> New Zealand Paient Spedficaiion for Paient Number £72296 New Zealand No. 272296 International No. PCT/ TO BE ENTERED AFTER ACCEPTANCE AND PUBLICATION Priority dates: 09.06.1994; Complete Specification Filed: 07.06.1995 Classification:(6) A01N47/34 Publication date: 24 November 1997 Journal No.: 1422 NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION Title of Invention: Method of controlling pests Name, address and nationality of applicant(s) as in international application form: CIBA-GEIGY AG, a Swiss corporation of Klybeckstrasse 141, 4002 Basle, Switzerland Patents Form Ho. 5 Our Re£: JB204809 NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION METHOD OF CONTROLLING PESTS We, CIBA-GEIGY AG, a Swiss corporation of Klybeckstrasse 141, 4002 Basle, Switzerland hereby declare the invention, for which We pray that a patent snay be granted to us and the method by which it is to be performed, to be particularly described in and by the following statement: PT0520668 - 1 - (followed by page la) PI/5-19979/A - W 27229 6 Method of controlling pests The present invention relates to a method of controlling pests which comprises applying a pesticidal composition comprising, as active ingredient, the compound of formula in the free form or in the form of a salt thereof, and at least one adjuvant, to the pests or to their habitat, said pests being (1) representatives of the family of the Thripidae, or (2) representatives of the genus Aculus. The invention also relates to the use of said compound, to pesticidal compositions comprising said compound, and to a process for the preparation of said compositions as well as to the use thereof. European patent EP-B-179 022 teaches that compounds of the type of the compound of formula I are suitable for controlling a great number of different pests. The Examples disclose how, in particular, insects of the order of Coleoptera, Diptera and Lepidoptera can be controlled. Unexpectedly and, in view of the above disclosure, most surprisingly, it has now been found that, from among the great number of compounds cited in EP-B-179 022 and from among the great number of orders of pests which may be controlled with said pesticidally effective compounds, the compound of formula I is particularly suitable for controlling pests and, in particular, representatives of the family of the Thripidae and genus Aculus. The control of pests of the aforementioned type is of great importance to the user in the field of pest control, for if these pests are not controlled systematically then e.g. great financial losses are incurred because of, for example, damage caused by said pests to agricultural products. (I, lufenuron), (followed by page 2 -2- Within the scope of this invention, a preferred method is that for controlling pests of the above-mentioned type, which comprises the use of the compound of formula I in the free form. Likewise preferred is a process for the control of (1) representatives of the genus Frankliniella, in particular of the species Frankliniella occidentalis. Frankliniella fuse a, Frankliniella tritici, Frankliniella vaccinii. Frankliniella bisoinosa. Fmnlclinip.Ua gossvoiana. Frankliniella parvula, Frankliniella robusta. Franlclinialla schultzei. Frankliniella tenuicornis and Frankliniftlla williamsi more particularly, Fnmklinip.lla nccidftntalfo; or (2) representatives of the species Aculus schlechtendali. Aculus fockeui, Aculus lvcopersicL Aculus masseii and Aculus pelekassi and, most particularly, Aculus schlechtendali. The compound of formula I used according to this invention is known and disclosed, inter alia, in EP-B-179 022. The compound of formula I used in the practice of this invention is a pest control agent which has useful preventive and curative properties already at low concentrations, and which is well tolerated by warm-blooded animals, fish and plants. The pest control agent used in the practice of this invention is effective against all, or individual, development stages of normally sensitive, but also of resistant, pests of the abovementioned type. The onset of the pesticidal activity of the pest control agent used in the practice of this invention may follow directly, i.e. a kill of the pest will occur immediately after, or only after some time, as when moulting is effected, or indirectly, e.g. reduced oviposition and/or hatching rate, the good activity corresponding to a mortality of at least 50 to 60%. To be particularly highlighted is the novel method by which resistant phylums of the above-mentioned pests are controlled, more particularly resistant phylums of the species Frankliniella occidentalis or Aculus schlechtendali. With the pest control agent useful in the practice of this invention it is possible to control, i.e. inhibit or destroy, in particular pests of the aforementioned type that occurjsjilants, # 272" -3- 29 more particularly in cultivated plants or ornamentals, in agriculture, horticulture and in forestry, or in parts of such plants such as fruit, blossoms, foliage, stems, tubers or roots, while in some cases parts of plants that grow later can also be protected against these pests. Particularly suitable target crops are: cereals such as wheat, barley, rye, oats, rice, maize or sorghum; beet such as sugar beet and fodder beet; fruit, e.g. pomes, drupes and soft fruit such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blueberries, red currants or blackberries; leguminous plants, e.g. beans, lentils, peas and soybeans; oil plants such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucurbits, e.g. marrows, cucumber and melons; fibre plants such as cotton, flax, hemp, or jute; citrus fruit, e.g. oranges, lemons, grapefruit and mandarins; vegetables such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, e.g. avocados, cinnamon and camphor; or tobacco, nuts, coffee, egg plants, sugar cane, tea, pepper, vines, hops, bananas, natural rubber plants and ornamentals; more particularly pomes, drupes and soft fruit, cereals, cucurbits, cotton, citrus fruit, vegetables, tomatoes, tobacco, bananas or ornamentals; most preferably cucurbits, vegetables or ornamentals. A particularly important aspect of the novel process is the control of a) Frankliniella occidentalis in vegetable cultures and ornamentals; or b) of Aculus schlechtendali in pomes, particularly in apples. Further utilities of the pest control agent useful in the practice of this invention are the protection of storage goods or materials and, in the hygiene sector, in particular the protection of domestic animals or productive livestock against pests of the indicated type. Accordingly, the invention also relates to pesticidal compositions for use against pests of the indicated type. Depending on the intended objectives and the prevailing circumstances, such compositions are emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, coatable pastes, dilute emulsions, wettable powders, soluble powders, dispersable powders, dusts, granules or encapsulations in polymeric materials, comprising at least one of the pest control agents useful in the practice of this invention. -4- 27229 The active ingredient is used in these compositions in pure form, the solid compound being used in a specific particle size or, preferably, together with at least one of the adjuvants customary in formulation technology, for example extenders such as solvents or solid carriers, or surface-active compounds (surfactants). Suitable solvents are typically: aromatic hydrocarbons or partially hydrogenated aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms of alkylbenzenes, typically xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene; aliphatic and cycloaliphatic hydrocarbons such as cyclohexane or paraffins; alcohols such as ethanol, propanol or butanol; glycols and their ethers and esters such as propylene glycol, dipropylene glycol ether, diethylene glycol, or 2-methoxyethanol or 2- ethoxyethanol; ketones such as cyclohexanone, isophorone or diacetone alcohol; strongly polar solvents such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or N,N-dimethyl formamide; water, vegetable oils or epoxidised vegetable oils such as epoxidised rapeseed oil, castor oil, coconut oil or soybean oil; or silicone oils. The solid carriers typically used for dusts and dispersible powders are usually natural mineral tillers such as calcite, talcum, kaolin, montmorillonite or attapulgite. To improve the physical properties it is also possible to add highly dispersed silicic acid or highly dispersed absorbent polymers. Suitable granulated adsorptive carriers are porous types, including pumice, broken brick, sepiolite or bentonite; and suitable nonsoibent carriers are materials such as calcite or sand. In addition, innumerable granulated materials of inorganic or organic origin may be used, especially dolomite or pulverised plant residues. Depending on the type of compound to be formulated, suitable surface-active compounds are nonionic, cationic and/or anionic surfactants or mixtures of surfactants having good emulsifying, dispersing and wetting properties. The surfactants listed below shall be regarded merely as exemplary; many more surfactants customarily employed in formulation technology and suitable for use in the practice of this invention are described in the relevant literature. Nonionic surfactants are preferably polyglycol ether derivatives of aliphatic or cycloaliphatic alcohols, or saturated or unsaturated fatty acids and alkylphenols, said derivatives containing 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon moiety and 6 to 18 carbon atoms in the alkyl moiety of the alkylphenols. Further suitable nonionic surfactants are the water-soluble polyadducts of -5- 27229 polyethylene oxide with polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol containing 1 to 10 carbon atoms in the alkyl chain, which polyadducts contain 20 to 250 ethylene glycol ether groups and 10 to 100 propylene glycol ether groups. These compounds usually contain 1 to 5 ethylene glycol units per propylene glycol unit Illustrative examples of nonionic surfactants are nonylphenol polyethoxylates, polyethoxylated castor oil, polyadducts of polypropylene and polyethylene oxide, tributylphenol polyethoxylates, polyethylene glycol and octylphenol polyethoxylates. Fatty acid esters of polyoxyethylene sorbitan are also suitable nonionic surfactants, typically polyoxyethylene sorbitan trioleate. Cationic surfactants are preferably quaternary ammonium salts carrying, as substituent, at least one C8-C22alkyl radical and, as further substituents, unsubstituted or halogenated alkyl, benzyl or hydroxy-lower alkyl radicals. The salts are preferably in the form of halides, methyl sulfates or ethyl sulfates, for example stearyl trimethylammonium chloride or benzyl bis(2-chloroethyl)ethylammonium bromide. Suitable anionic surfactants may be water-soluble soaps as well as water-soluble synthetic surface-active compounds. Suitable soaps are the alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts of higher fatty acids (CjQ-Cg), e.g. the sodium or potassium salts of oleic or stearic acid, or of natural fatty acid mixtures which can be obtained, inter alia, from coconut oil or tall oil. Further suitable soaps are also the fatty acid methyl taurin salts. More often, however, so-called synthetic surfactants are used, especially fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates. The fatty alcohol sulfonates or sulfates are usually in the form of alkali metal salts, alkaline earth metal salts, ammonium salts or substituted ammonium salts, and they typically contain a Cg-C^alkyl radical which also includes the alkyl moiety of acyl radicals, e.g. the sodium or calcium salt of ligninsulfonic acid, of dodecylsulfate, or of a mixture of fatty alcohol sulfates obtained from natural fatty acids. These compounds also comprise the salts of sulfated or sulfonated fatty alcohol/ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain two sulfonic acid groups and one fatty acid radical containing 8 to 22 carbon atoms. Illustrative examples of alkylarylsulfonates are the sodium, calcium or triethanolamine salts of dodecylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or of a condensate of naphthalenesulfonic acid and formaldehyde. Corresponding phosphates, typically salts of the phosphoric acid ester of an adduct of p-nonylphenol with 4 to 14 mol of ethylene oxide, or phospholipids, are also suitable. -6- *- " k- v. ;27229 ;The compositions usually comprise 0.1 to 99% by weight, more particularly 0.1 to 95% by weight, of active ingredient, and 1 to 99.9% by weight, more particularly at least 5 to 99.9% by weight, of a solid or liquid adjuvant; usually they will contain 0 to 25%, more particularly 0.1 to 20%, of surfactants. Whereas commercial products will preferably be formulated as concentrates, the end user will normally use dilute formulations having a substantially lower concentration of active ingredient Particularly preferred formulations will be made up as follows (% = percent by weight): ;Emulsifiable concentrates: ;active ingredient: 1 to 90%, preferably 5 to 20% ;surfactant: 1 to 30%, preferably 10 to 20% ;solvent: 5 to 98%, preferably 70 to 85% ;Dusts: ;active ingredient: 0.1 to 10%, preferably 0.1 to 1% ;solid carrier 99.9 to 90%, preferably 99.9 to 99% ;Suspension concentrates: active ingredient: ;water: ;surfactant: ;5 to 75%, preferably 10 to 50% 94 to 24%, preferably 88 to 30% 1 to 40%, preferably 2 to 30% ;Wettable powder: active ingredient: surfactant: ;solid carrier: ;0.5 to 90%, preferably 1 to 80% 0.5 to 20%, preferably 1 to 15% 5 to 99%, preferably 15 to 98% ;Granulates: ;active ingredient: solid carrier ;0.5 to 30%, preferably 3 to 15% 99.5 to 70%, preferably 97 to 85% ;The activity spectrum of the novel compositions may be substantially broadened and adapted to prevailing circumstances by addition of other pest control agents. Suitable additives are, in particular, members of the following classes of compounds: organophosphorous compounds, nitrophenols and derivatives, formamidines, urea, ;carbamates, pyrethroids, chlorinated hydrocarbons, and Bacillus thuringiensis compositions. The novel compositions may also comprise further solid or liquid adjuvants, typically stabilisers such as plant oils or epoxidised plant oils (e.g. epoxidised coconut oil, rapeseed oil or soybean oil), antifoams such as silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, as well as fertilisers or other chemical compounds to obtain special effects, typically bactericides, fungicides, nematicides, molluscicides or selective herbicides. ;The novel compositions are prepared in known manner, in the absence of adjuvants, for example, by grinding, sieving and/or compressing a solid active ingredient or mature thereof, for example to a specific particle size and, in the presence of at least one adjuvant, by thorough blending and/or grinding of the active ingredient or mixture thereof with the adjuvant or adjuvants. The invention also relates to the above processes for preparing the novel compositions and to the use of the compound of formula 1 for preparing said compositions. ;The methods of applying the compositions, i.e. the methods of controlling pests of the indicated type, typically spraying, atomising, dusting, coating, dressing, scattering or pouring, selected in accordance with the intended objectives and the prevailing circumstances, and the use of the compositions for controlling pests of the indicated type, are further objects of the invention. Typical rates of application are in the range from 0.1 to 1000 ppm, preferably from 0.1 to 500 ppm, of active ingredient It is preferred to use spray mixtures containing the active ingredient in a concentration of 30, 50,80,100,150 or 200 ppm. The rates of application per hectare are usually from 1 to 2000 g of active ingredient per hectare, more particularly from 10 to 1000 g/ha, preferably from 20 to 600 g/ha. Rates of application of 300,400 or 450 g of active ingredient per hectare are preferred. The preferred rates of application per tree are 0.25,0.75,1.0 or 2.0 g. ;A preferred method of application in the field of plant protection is foliar application. The frequency of application and the rate of application will depend on the risk of infestation by the particular pest However, the active ingredient may also be absorbed by the plant through the roots (systemic activity) by drenching the locus of the plant with a liquid composition or by applying the active ingredient in solid form to the locus of the plants, e.g. to the soil, typically in the form of granulates (soil application). ;The following non-limitative Examples illustrate the invention. ;* 8- 072^ Formulation Examples (throughout, percentages are by weight) Example Fl: Emulsifiable concentrates a) b) c) active ingredient 25% 40% 50% calcium dodecylbenzene sulfonate 5 % 8 % 6 % polyethoxylated castor oil (36 mol EO) 5% tributylphenol polyethoxylate (30 mol EO) - 12% 4% cyclohexanone - 15 % 20 % mixture of xylenes 65 % 25 % 20 % Emulsions of any desired concentration can be prepared by diluting such concentrates with water. Example F2: solutions a) b) c) d) active ingredient 80 % 10 % 5 % 95 % 2-methoxyethanol 20 % - polyethylene glycol MG 400 - 70% - N-methyl-2-pyrrolidone - 20 % epoxidised coconut oil - - 1 % 5 % white spirit (boiling range 160-190°) - - 94% - The solutions are suitable for use as micrortrops. Example F3: Granulates a) b) c) d) active ingredient 5% 10% 8% 21 % kaolin 94% - 79% 54% highly dispersed silica 1 % - 13% 7% attapulgite - 90% - 18% The active ingredient is dissolved in dichloromethane, the solution is sprayed on to the carrier, and the solvent is then removed under vacuum. 9- a) b) 2% 5% 1% 5% 97% • 272?q Example F4: Dusts active ingredient highly dispersed silica talcum kaolin 90 % Ready for use dusts are obtained by intimately mixing the active ingredient with the carriers. Example F5: Wettable powder a) b) c) active ingredient 25 % 50 % 75 % sodium ligninsulfonate 5 % 5% sodium laurylsulfate 3 % - 5 % sodium diisobutylnaphthalene sulfonate - 6 % 10 % octylphenol polyethoxylate (7-8 mol EO) - 2% highly dispersed silica 5% 10 % 10 % kaolin 62 % 27 % The active ingredient is mixed with the adjuvants and this mixture is v».ll ground in a suitable mill to give wettable powders which can be diluted with water to give suspensions of any desired concentration. Example F6: Emulsifiable concentrate active ingredient 10 % octylphenol polyethoxylate (4-5 mol EO) 3% calcium dodecylbenzenesulfonate 3 % polyethoxylated castor oil (36 mol EO) 4% cyclohexanone 30 % mixture of xylenes 50 % Emulsions of any desired concentration can be prepared by diluting such concentrates with water. 2722 9 8 Example F7: Dusts a) b) active ingredient 5% 8 % talcum 95 % kaolin - 92 % Ready for use dusts are obtained by mixing the active ingredient with the carriers on a suitable mill. Example F8: Extruder granulate active ingredient 10 % sodium ligninsulfonate 2 % carboxymethyl cellulose 1 % kaolin 87 % The active ingredient is mixed with the adjuvants and the mixture is then milled and moistened with water. This mixture is extruded, granulated and then dried in a stream of air. Example F9: Coated granulate active ingredient 3 % polyethylene glycol (MG 200) 3 % kaolin 94 % The fmely ground active ingredient is uniformly applied in a mixer to the kaolin moistened with polyethylene glycol. Non-dusty coated granulates are obtained in this manner. Example F10: Suspension concentrate active ingredient 40 % ethylene glycol 10 % nonylphenol polyethoxylate (15 mol EO) 6 % sodium ligninsulfonate 10 % carboxymethyl cellulose 1 % 37% aqueous formaldehyde solution 0.2 % </div>

Claims

<div class="application article clearfix printTableText" id="claims"> silicone oil in form of a 75% aqueous emulsion water 0.8% 32 % The finely ground compound mixture is intimately mixed with the adjuvants to give a suspension concentrate from which suspensions of any desired concentration can be prepared by dilution with water. Biological Examples Example Bl: Action against Frankliniella occidentalis Paprika plants in a greenhouse, which are populated with a natural mixed population of larvae, nymphs and adults of Frankliniella occidentalis, are sprayed three times to drip point at intervals of 10 days with a spray mixture containing 10 g/hl of the compound of formula I. Immediately before the second, and one day after the third, treatment, the nymphs on the treated plants and on untreated control plants are counted and the reduction in the number of nymphs is determined. After 10 days, the reduction is 92 %, and after 21 days 97 %. -12- 272 2 9 6 WHAT/(/WE CLAIM IS:

1. A method of controlling pests which comprises applying a pesticidal composition comprising, as active ingredient, the compound of formula in the free form or in the form of a salt thereof, and at least one adjuvant, to the pests or to their habitat, said pests being (1) representatives of the family of the Thripidae, or (2) representatives of the genus Aculus.

2. A method according to claim 1, wherein the compound of formula I is used in the free form.

3. A method according to either claim 1 or claim 2 for controlling representatives of the genus Frankliniella.

4. A method according to claim 3 for controlling the species Frankliniella occidentalis. Frankliniella fusca, Frankliniella tritici. Frankliniella vaccinii. Frankliniella bispinosa. Frankliniella gossypiana, Frankliniella parvula, Frankliniella robusta. Franklinielk schultzei, Frankliniella tenuicornis or Frankliniella williamsi.

5. A method according to either claim 1 or claim 2 for controlling representatives of the jrcnus Aculus. CL lufenuron), </div>