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WO1997002746A1 - Synergistic pesticidal composition of diafenthiuron and tebufenpyrad - Google Patents

Synergistic pesticidal composition of diafenthiuron and tebufenpyrad Download PDF

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Publication number
WO1997002746A1
WO1997002746A1 PCT/EP1996/002859 EP9602859W WO9702746A1 WO 1997002746 A1 WO1997002746 A1 WO 1997002746A1 EP 9602859 W EP9602859 W EP 9602859W WO 9702746 A1 WO9702746 A1 WO 9702746A1
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spp
formula
composition
active compound
compound
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Application number
PCT/EP1996/002859
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French (fr)
Inventor
Hans-Peter Streibert
Hubert Buholzer
Markus Julmy
Original Assignee
Novartis Ag
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Publication date
Application filed by Novartis Ag filed Critical Novartis Ag
Priority to AU65158/96A priority Critical patent/AU6515896A/en
Publication of WO1997002746A1 publication Critical patent/WO1997002746A1/en

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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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

Definitions

  • the present invention relates to a pesticidal composition, which comprises a combination of pesticidally active compounds, a method of controlling pests using the said composition, a process for the preparation of the composition, its use and plant propagation material treated with it, and the use of the compounds of the following formulae (A) and (B) for the preparation of the composition.
  • the invention relates to a pesticidal copmpositon which comprises a combination, which can be varied in terms of amounts, of the pesticidally active compound of the formula
  • the compound 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)thiourea (diafenthiuron) of the f ⁇ Ryte(A) is known, fer xample, from The Pesticide Manual, 10 th Ed. (1994), The Brit ⁇ ish Crop Protection Council, London, page 294.
  • N-(4-tert-butylbenzyl)-4-chloro-3-ethyl-1 -methylpyrazole-5-carboxamide (tebufenpyrad) of the formula (B) is known, for example, from The Pesticide Manual, 10 ,h Ed. (1994), The British Crop Protection Council, London, page 945.
  • Agrochemically tolerated salts of the compounds of the formulae (A) and (B) are, for exam ⁇ ple, acid addition salts of inorganic or organic acids, in particular of hydrochloric acid, hy ⁇ drobromic acid, sulfuric acid, nitric acid, perchloric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, malonic acid, toluenesulfonic acid or benzoic acid.
  • compositions which comprise, as active ingredients, the compounds of the formulae (A) and (B) in the free form are preferred in the context of the present invention.
  • the combinations of active compounds according to the invention preferably comprise the active compound of the formula (A) and the active compound of the formula (B) in a mixing ratio (weight ratio, in the ratio of their molecular weights or the ratio of the LD50 values for a particular pest to be controlled) of 1 :50 to 50:1 , in particular in a ratio between 1 :20 and 20:1, especially between 10.J and 1:10, also preferably between 50:1 and 3:1, very par ⁇ ticularly between 40:1 and 10:1, also preferably between 2:1 and 1:2, or in a ratio of 40:1 or 30:1 , or 20:1 , or 20:3, or 15:1 , or 10:1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 : 20, or 1 :10, or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 3:4, or 1 :3, or 2
  • the composition according to the invention is outstandingly suitable for controlling curatively and, in some cases, also preventively a very advanta ⁇ geous spectrum of pests, even at low rates of application, while being well toler ⁇ ated by, for example, warm-blooded animals, fish and plants.
  • the composition according to the invention is effective against all or individual development stages of normally sensitive and also resistant pests, such as insects or representatives of the order Acarina.
  • the good pesticidal activity of the composition according to the invention may manifest itself directly, that is to say in the death of the pests, which occurs immediately or only at a later date, or indirectly, for example in a re ⁇ quiz oviposiilon and/or a reduced hatching rate of corresponding pests, the good activity corresponding, for example, to a mortality and/or a reduction in the oviposition and/or in the hatching rate of at least 50 to 60 %.
  • the animal pests mentioned include,: from the order Lepidoptera, for example
  • Blatta spp. Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. and Schistocerca spp.; from the order Isoptera, for example, Reticulitermes spp.; from the order Psocoptera, for example, Liposcelis spp.; from the order Anoplura, for example,
  • Haematopinus spp. Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; from the order Mallophaga, for example, Damalinea spp. and Trichodectes spp.; from the order Thysanoptera, for example,
  • Cimex spp. Distantiella theobroma, Dysdercus spp., Euchistus spp., Eurygaster spp. Lep- tocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotino- phara spp. and Triatoma spp.; from the order Homoptera, for example,
  • Aedes spp. Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Glossina spp., Hypoderma spp., Hyppobosca spp., Lirio- myza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Os- cinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis pomonella, Sciara spp., Sto- moxys spp., Tabanus spp.
  • Lepisma saccharina and from the order Acarina, for example,
  • Thysanoptera in particular of the family Thripidae, especially Frankliniella spp., Thrips palmi and Thrips tabaci;
  • Pests of the type mentioned which occur on plants, in particular on useful plants and orna ⁇ mentals in agriculture, in horticulture and in forestry, or on parts, such as fruit, blossom, foli ⁇ age, stems, tubers or roots, of such plants can be controlled, i.e. checked or destroyed, in particular using the composition according to the invention, even parts of plants which grow later in some cases being protected against these pests.
  • the active composition according to the invention can advantageously be employed for pest control in cereals, such as maize or sorghum; in fruit, for example pome, stone and soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries and blackberries; in leguminous plants, such as beans, lentils, peas or soya; in oil crops, such as oilseed rape, mustard, poppy, olives, sunflowers, coco ⁇ nut, Ricinus, cocoa or groundnuts; in gourds, such as pumpkins, cucumbers or melons; in fibre plants, such as cotton, flax, hemp or jute; in citrus fruits, such as oranges, lemons, grapefruits or tangerines; in vegetables, such as spinach, lettuce, asparagus, cabbage spe ⁇ cies, carrots, onions, tomatoes, potatoes or capsicum; in laurel family plants, such as avo ⁇ cado, cinnamon or camphor; or in tobacco, nuts, coffee, au
  • the pesticidal activity of the composition ac ⁇ cording to the invention if compared with the combined pesticidal activities of the individual compounds (A) and (B) together forming the active ingredient of the instant composition, is not only additive, as can be expected in principle, but also shows a surprising synergistic effect.
  • the term "synergistic effect" is neither limited to the pure pesticidal activity against a certain pest species, nor is it necessary, that this term relates at all to the pure pesticidal activity, but this term can relate to any property of the instant composition, which is advantageous, if compared with the combined corresponding properties of the in ⁇ dividual compounds (A) and (B) together forming the active ingredients of the instant com ⁇ position.
  • Such advantageous properties of the instant composition there may be mentioned: a broadening in the spectrum of the pesticidal activity towards additional or different pests, for example towards a resistant pest species; a reduction in the rates of application of the compounds (A) and/or (B); a sufficient degree of pest control by means of the instant composition even in cases where the individual compounds (A) and (B) to ⁇ gether forming the active ingredient of the instant composition are totally ineffective due to their extremely low rates of application; an advantageous behaviour in the case of being formulated and/or applied, for example if being ground, sieved, compressed, emulsified, dissolved, dispersed or sprayed; an improved storage stability; a better light stability; a bet ⁇ ter heat stability; an advantageous behaviour in the case of being degraded; a better toxi ⁇ cology profile; an improved ecotoxicological behaviour; other advantages familiar to those skilled in the art.
  • compositions according to the invention are emulsifiable concentrates, suspension concentrates, solutions which can be sprayed or diluted directly, spreadabie pastes, dilute emulsions, wettable powders, solu ⁇ ble powders, dispersible powders, dusts, granules or capsules in polymeric substances, which comprise the active compounds of the formulae (A) and (B).
  • the active compounds are employed in these compositions together with at least one of the auxiliaries conventionally used in the art of formulation, such as extenders, for example sol ⁇ vents or solid carriers, or such as surface-active compounds (surfactants).
  • Solvents can be, for example: non-hydrogenated or partly hydrogenated aromatic hydro ⁇ carbons, preferably fractions C 8 to C12 of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols, such as ethanol, propanol or butanol, glycols and ethers and esters thereof, such as propylene glycol, dipropylene glycol ethers, ethylene glycol or ethylene glycol mono-methyl or -ethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly
  • Solid carriers which can be used are as a rule natural rock powders, such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly disperse silicic acids or highly disperse absorbent polymers can also be added to improve the physical properties.
  • Granular adso ⁇ tive granule carriers are porous types, such as pumice, crushed brick, sepiolite or bentonite, and non-absorbent carrier materials are calcite or sand. A large number of granulated materials of inorganic or organic nature, in particular dolomite or comminuted plant residues, can furtheimore be used.
  • Surfact active compounds are, depending on the nature of the active compound to be for ⁇ mulated, nonionic, cationic and/or anionic surfactants or surfactant mixtures with good emulsifying, dispersing and wetting properties.
  • the surfactants listed below are to be re ⁇ knit only as examples; many other surfactants which are conventionally used in the art of formulation and are suitable according to the invention are described in the relevant lit ⁇ erature.
  • Nonionic surfactants are, in particular, polyglycolether derivatives of aliphatic or cy ⁇ cloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can com ⁇ prise 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols.
  • Water-soluble polyethylene oxide adducts containing 20 to 250 ethylene glycol ether and 10 to 100 pro ⁇ pylene glycol ether groups, on polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol having 1 to 10 carbon atoms in the alkyl chain are further ⁇ more suitable.
  • the compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit. Examples are nonylphenolpolyethoxyethanols, castor oil polyglycol ether, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, poly ⁇ ethylene glycol and octylphenoxypolyethoxyethanol.
  • Fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylenesorbitan- trioleate, are furthermore suitable.
  • the cationic surfactants are, in particular, quaternary ammonium salts which contain, as substituents, at least one alkyl radical having 8 to 22 C atoms and, as further substituents, Iower, non-halogenated or halogenated alkyl, benzyl or Iower hydroxy alkyl radicals.
  • the salts are preferably in the form of halides, methyl-sulfates or ethyl-sulfates. Examples are stearyl-trimethyl-ammonium chloride and benzyl-di-(2-chloroethyl)-ethyl-ammonium bro ⁇ mide.
  • Suitable anionic surfactants can be either water-soluble soaps or water-soluble synthetic surface-active compounds.
  • Suitable soaps are, for examples, the alkali metal, alkaline earth metal and substituted or unsubstituted ammonium salts of higher fatty acids (C10-C 22 ), such as the sodium or potassium salts of oleic or stearic acid, or of naturally occurring fatty acid mixtures, which can be obtained, for example, from coconut oil or tall oil; and also the fatty acid methyl-taurine salts.
  • synthetic surfactants in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates, are more often used.
  • the fatty sulfonates and -sulfates are as a rule in the form of alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts and in general contain an alkyl radical having 8 to 22 C atoms, alkyl also including the alkyl moiety of acyl radicals; examples are the sodium or calcium salt of ligninsulfonic acid, of dodecylsulfuric acid ester or of a fatty alcohol sulfate mixture prepared from naturally occurring fatty acids. These also include the salts of the sulfuric acid esters and sulfonic acids of fatty alcohol-ethylene oxide adducts.
  • the sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid radical having about 8 to 22 C atoms.
  • Alkylarylsulfonates are, for example, the sodium, calcium or triethanolammonium salts of dodecylbenzenesulfonic acid, of dibutyl- naphthalenesulfonic acid or of a naphthalenesulfonic acid-formaldehyde condensation product.
  • Corresponding phosphates such as salts of the phosphoric acid ester of a p- nonylphenol (4-14)-ethylene oxide adduct or phospholipids, are furthermore also suitable.
  • compositions as a rule comprise OJ to 99%, in particular OJ to 95%, of a mixture of the active compound of the formula (A) with the active compound of the formula (B), and 1 to 99.9%, in particular 5 to 99,9%, of - at least - one solid or Iiquid auxiliary, and as a rule 0 to 25%, in particular OJ to 20%, of the composition can be surfactants (% is in each case per cent by weight). While concentrated compositions are preferred as commercial goods, the end user as a rule uses dilute compositions which have considerably Iower active com- pound concentrations. Preferred compositions are composed, in particular, as follows (% per cent by weight):
  • Emulsifiable concentrates Mixture of (A) and (B): 1 to 90%, preferably 5 to 20% Surfactant: 1 to 30%, preferably 10 to 20 % Solvent: 5 to 98%, preferably 70 to 85%
  • Suspension concentrates Mixture of (A) and (B): 5 to 75%, preferably 10 to 50% Water: 94 to 24%, preferably 88 to 30% Surfactant: 1 to 40%, preferably 2 to 30%
  • Wettable powders Mixture of (A) and (B): 0.5 to 90%, preferably 1 to 80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 99%, preferably 15 to 98%
  • Solid carrier 99.5 to 70%, preferably 97 to 85%
  • compositions according to the invention can also comprise other solid or Iiquid auxilia ⁇ ries, such as stabilisers, for example nonepoxidized or epoxidized plant oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or adhesives, as well as fertilisers or other active compounds for achieving special effects, for example bactericides, fungicides, nema- ticides, molluscicides or herbicides.
  • stabilisers for example nonepoxidized or epoxidized plant oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or adhesives, as well as fertilisers or other active compounds for achieving special effects, for example bactericides, fungicides, nema- ticide
  • compositions according to the invention are prepared in a known manner, for example by grinding, sieving and/or pressing an active compound or the active compound mixtures, for example to a particular particle size, before mixing with the auxiliary or auxiliaries, and by intimate mixing and/or grinding of the active compound mixture with the auxiliary or aux ⁇ iliaries.
  • the invention therefore also relates to the process for the preparation of the compo ⁇ sitions.
  • the invention also relates to the methods of application of the compositions, i.e. the meth ⁇ ods for controlling pests of the type mentioned, such as - to be chosen according to the in ⁇ tended aims and given circumstances - spraying, wetting, atomizing, dusting, brushing, dressing, scattering, or pouring, and to the use of the compositions for controlling pests of the type mentioned.
  • Typical rates of concentration are between OJ and 1000 ppm, prefera ⁇ bly between OJ and 500 ppm of active ingredient.
  • the rate of application can vary within wide limits and depends on the nature of the soil, the type of application (foliar application; seed dressing; application in the seed furrow), the crop plant, the pest to be controlled, the particular prevailing climatic circumstances and other factors determined by the type of ap ⁇ plication, the time of application and the target crop.
  • the rates of application per hectare are in general 1 to 2000 g of active ingredientompound per hectare, in particular 10 to 1000 g/ha, preferably 20 to 600 g/ha, particularly preferably 20 to 200 g/ha.
  • a preferred method of application in the field of plant protection is application to the foliage of the plants (foliar application), where the frequency of application and rate of application can depend on the risk of infestation by the particular pest.
  • the active compounds can also enter the plants via the root system (systemic action), by steeping the location of the plants with a Iiquid composition or introducing the active compounds into the location of the plants, for example into the soil, in solid form, for example in the form of granules (soil application). In paddy rice crops, such granules can be metered into the flooded rice field.
  • compositions according to the invention are also suitable for protection of plant propa ⁇ gation material, for example, seed, such as fruit, tubers or grains, or plant seedlings, against animal pests.
  • the propagation material can be treated with the composition before placement, for example seed can be dressed before sowing.
  • the active compounds ac ⁇ cording to the invention can also be applied to seed grains (coating) by either steeping the grains in a Iiquid composition or coating them with a solid composition.
  • the composition can also be applied to the placement location during placement of the propagation material, for example during sowing in the seed furrow.
  • the invention also relates to this treatment method for plant propagation material and the plant propagation material treated in this way.
  • Example F1 Emulsion concentrates a) b) c)
  • Active ingredients [ratio of the compounds of the formulae (A) and (B) 1 :1] 25 % 40 % 50 %
  • Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
  • Example F2 Solutions a) b) c) d)
  • Active ingredients (10 : 1) 80 % 10 % 5 % 95 %
  • Example F3 Granules a) b) C) d)
  • the active compounds are dissolved together in dichloromethane, the solution is sprayed onto the carrier and the solvent is then evaporated off in vacuo.
  • Example F4 Dusts a) b)
  • Ready-to-use dusts are obtained by intimate mixing of the carriers with the active com ⁇ pounds.
  • Example F5 Wettable powders a) b) c)
  • Example F6 Emulsion concentrate
  • Emulsions of any desired concentration can be prepared from this concentrate by dilution with water.
  • Active compound mixture (1 : 2) 5 % 8 %
  • Ready-to-use dusts are obtained by mixing the active compounds with the carrier and grinding the mixture on a suitable mill.
  • the active compounds are mixed with the additives and the mixture is ground and mois ⁇ tened with water. This mixture is extruded and granulated and the granules are then dried in a stream of air.
  • Example F9 Coated granules Active compound mixture (1 : 1) 3 %
  • the finely ground active compounds are applied uniformly, in a mixer, to the kaolin mois ⁇ tened with polyethylene glycol. Dust-free coated granules are obtained in this manner.
  • Example B3 Ovicidal action on Lobesia botrana
  • the combinations of the active compound of the formula (A) with the ac ⁇ tive compound of the formula (B) show a synergistic effect.
  • the combination of 100 ppm of the active compound of the formula (A) with 300 ppm of the active compound of the formula (B), and the combination of 250 ppm of the active compound of the formula (A) with 150 ppm of the active compound of the formula (B) show a very good effect.
  • Example B4 Ovicidal action on Heliothis virescens

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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Abstract

A pesticide which comprises a combination, which can be varied in terms of amounts, of the pesticidally active compound of formula (A, diafenthiuron), in the free form or in the form of an agrochemically tolerated salt, and of the pesticidally acitve compound of formula (B, tebufenpyrad), in the free form or in the form of an agrochemically tolerated salt, and at least one auxiliary, a method of controlling pests, a process for the preparation of the composition, its use and plant propagation material treated with it, and the use of the compound of formula (A) and the use of the compound of formula (B) for preparation of the composition are described.

Description

SYNERGISTIC PESTICIDAL COMPOSITION OF DIAFENTHIURON AND TEBUFENPYRAD.
The present invention relates to a pesticidal composition, which comprises a combination of pesticidally active compounds, a method of controlling pests using the said composition, a process for the preparation of the composition, its use and plant propagation material treated with it, and the use of the compounds of the following formulae (A) and (B) for the preparation of the composition.
Certain mixtures of active compounds are proposed for pest control in the literature. How¬ ever, the biological properties of these known mixtures are not completely satisfactory in the field of pest control, and there is therefore the need to provide further mixtures, in particular for controlling insects and representatives of the order Acarina. This object is achieved ac¬ cording to the invention by providing the present composition.
The invention relates to a pesticidal copmpositon which comprises a combination, which can be varied in terms of amounts, of the pesticidally active compound of the formula
(A, diafenthiuron),
Figure imgf000003_0001
in the free form or in the form of an agrochemically tolerated salt, and of the pesticidally active compound of the formula
(B. tebufenpyrad)
Figure imgf000003_0002
in the free form or in the form of an agrochemically tolerated salt, and at least one auxiliary. The compound 1-tert-butyl-3-(2,6-diisopropyl-4-phenoxyphenyl)thiourea (diafenthiuron) of the fθβRyte(A) is known, fer xample, from The Pesticide Manual, 10thEd. (1994), The Brit¬ ish Crop Protection Council, London, page 294.
The compound N-(4-tert-butylbenzyl)-4-chloro-3-ethyl-1 -methylpyrazole-5-carboxamide (tebufenpyrad) of the formula (B) is known, for example, from The Pesticide Manual, 10,hEd. (1994), The British Crop Protection Council, London, page 945.
Agrochemically tolerated salts of the compounds of the formulae (A) and (B) are, for exam¬ ple, acid addition salts of inorganic or organic acids, in particular of hydrochloric acid, hy¬ drobromic acid, sulfuric acid, nitric acid, perchloric acid, phosphoric acid, formic acid, acetic acid, trifluoroacetic acid, oxalic acid, malonic acid, toluenesulfonic acid or benzoic acid.
Compositions which comprise, as active ingredients, the compounds of the formulae (A) and (B) in the free form are preferred in the context of the present invention.
The combinations of active compounds according to the invention preferably comprise the active compound of the formula (A) and the active compound of the formula (B) in a mixing ratio (weight ratio, in the ratio of their molecular weights or the ratio of the LD50 values for a particular pest to be controlled) of 1 :50 to 50:1 , in particular in a ratio between 1 :20 and 20:1, especially between 10.J and 1:10, also preferably between 50:1 and 3:1, very par¬ ticularly between 40:1 and 10:1, also preferably between 2:1 and 1:2, or in a ratio of 40:1 or 30:1 , or 20:1 , or 20:3, or 15:1 , or 10:1 , or 5:1 , or 5:2, or 5:3, or 5:4, or 4:1 , or 4:3, or 3:1 , or 3:2, or 2:1 , or 1 : 20, or 1 :10, or 1 :5, or 2:5, or 3:5, or 4:5, or 1 :4, or 3:4, or 1 :3, or 2:3, or 1 :2, or 1:1.
Surprisingly, the composition according to the invention is outstandingly suitable for controlling curatively and, in some cases, also preventively a very advanta¬ geous spectrum of pests, even at low rates of application, while being well toler¬ ated by, for example, warm-blooded animals, fish and plants. The composition according to the invention is effective against all or individual development stages of normally sensitive and also resistant pests, such as insects or representatives of the order Acarina. The good pesticidal activity of the composition according to the invention may manifest itself directly, that is to say in the death of the pests, which occurs immediately or only at a later date, or indirectly, for example in a re¬ duced oviposiilon and/or a reduced hatching rate of corresponding pests, the good activity corresponding, for example, to a mortality and/or a reduction in the oviposition and/or in the hatching rate of at least 50 to 60 %.
The animal pests mentioned include,: from the order Lepidoptera, for example
Acleris spp., Adoxophyes spp., Aegeria spp., Agrotis spp., Alabama argillaceae, Amylois spp., Anticarsia gemmatalis, Archips spp., Argyrotaenia spp., Autographaspp., Busseola fusca, Cadra cautella, Carposina nipponensis, Chilo spp., Choristoneura spp., Clysia am¬ biguella, Cnaphalocrocis spp., Cnephasia spp., Cochylis spp., Coleophora spp., Crocidolo- mia binotalis, Cryptophlebia leucotreta, Cydia spp., Diatraea spp., Diparopsis castanea, Earias spp., Ephestia spp., Eucosma spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Grapholita spp., Hedya nubiferana, Heliothis spp., Hellula undalis, Hyphantria cunea, Keiferia lycopersicella, Leucoptera scitella, Lithocollethis spp., Lobesia botrana, Lymantria spp., Lyonetia spp., Malacosoma spp., Mamestra brassicae, Manduca sexta, Operophtera spp., Ostrinia nubilalis, Pammene spp., Pandemis spp., Panolis flammea, Pectinophora gossypiella, Phthorimaea operculella, Pieris rapae, Pieris spp., Plutella xylostella, Prays spp., Scirpophaga spp., Sesamia spp., Sparganothis spp., Spodoptera spp., Synanthedon spp., Thaumetopoea spp., Tortrix spp., Trichoplusia ni and Yponomeuta spp.; from the order Coleoptera, for example,
Agriotes spp., Anthonomus spp., Atomaria linearis, Chaetocnema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp., Lepti- notarsa decemlineata, Lissorhoptrus spp., Melolontha spp., Oryzaephilus spp., Otiorhyn- chus spp., Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp., Scarabeidae, Sitophilus spp., Sitotroga spp., Tenebrio spp., Tribolium spp. and Trogoderma spp.; from the order Orthoptera, for example,
Blatta spp., Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. and Schistocerca spp.; from the order Isoptera, for example, Reticulitermes spp.; from the order Psocoptera, for example, Liposcelis spp.; from the order Anoplura, for example,
Haematopinus spp., Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; from the order Mallophaga, for example, Damalinea spp. and Trichodectes spp.; from the order Thysanoptera, for example,
Frankliniella spp., Hercinothrips spp., Taeniothrips spp., Thrips palmi, Thrips tabaci and Scirtothrips aurantii; from the order Heteroptera, for example,
Cimex spp., Distantiella theobroma, Dysdercus spp., Euchistus spp., Eurygaster spp. Lep- tocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis, Scotino- phara spp. and Triatoma spp.; from the order Homoptera, for example,
Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, Aphis spp., As- pidiotus spp., Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium, Chrysomphalus dictyospermi, Coccus hesperidum, Empoasca spp., Eriosoma lanigerum, Erythroneura spp., Gascardia spp., Laodelphax spp., Lecanium comi, Lepidosaphes spp., Macrosiphus spp., Myzus spp., Nephotettix spp., Nilaparvata spp., Paratoria spp., Pemphigus spp., Planococ- cus spp., Pseudaulacaspis spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetiaspp., Scaphoideus spp., Schizaphis spp., Sitobion spp., Trialeurodes vaporariorum, Trioza erytreae and Unaspis citri; from the order Hymenoptera, for example,
Acromyrmex, Atta spp., Cephus spp., Diprion spp., Diprionidae, Gilpinia polytoma, Hoplo¬ campa spp., Lasius spp., Monomorium pharaonis, Neodiprion spp., Solenopsis spp. and Vespa spp.; from the order Diptera, for example,
Aedes spp., Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster, Fannia spp., Gastrophilus spp., Glossina spp., Hypoderma spp., Hyppobosca spp., Lirio- myza spp., Lucilia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp., Os- cinella frit, Pegomyia hyoscyami, Phorbia spp., Rhagoletis pomonella, Sciara spp., Sto- moxys spp., Tabanus spp., Tannia spp. and Tipula spp.; from the order Siphonaptera, for example,
Ceratophyllus spp. and Xenopsylla cheopis; from the order Thysanura, for example,
Lepisma saccharina, and from the order Acarina, for example,
Acarus siro, Aceria sheldoni, Aculus spp., Amblyomma spp., Argas spp., Boophilus spp.,
Brevipalpus spp., Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp., Dermanyssus gallinae, Eotetranychus caφini, Eriophyes spp., Hyalomma spp., Ixodes spp., Olygonychus pratensis, Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotar- sonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp.,
Tarsonemus spp. and Tetranychus spp..
In the context of the subject matter of the invention, in particular pests
(1) of the order Lepidoptera, in particular Adoxophyes spp., Alabama argillaceae, Clysia ambiguella, Clysia pomonella, Crocidolomia binotalis, Cydiaspp., Earias spp., Heliothis spp., Lobesia botrana, Ostrinia nubilalis, Phthorimaea operculella, Sparganothis spp. and Spodoptera spp.;
(2) of the order Coleoptera, in particular of the family Curculionidae, in particular Anthonomus spp., especially A. gran- dis, in particular of the family Chrysomelidae, in particular Leptinotarsa decemlineata;
(3) of the order Homoptera in particular of the family Aphididae, especially of the genus Aphis, particularly A. gossypii; in particular of the family Aleurodidae, in particular Aleurothrixus floccus and Bemisia tabaci; in particular of the family Psyllidae, especially particularly Psylla spp.,
(4) of the order Thysanoptera, in particular of the family Thripidae, especially Frankliniella spp., Thrips palmi and Thrips tabaci;
(5) of the order Acarina, in particular of the family Eriophyidae, especially Aculus schlechtendali and Phyllocoptruta oleivora; in particular Tetranychus spp., and (6) of the order Diptera, in particular of the family Agromyzidae, especially Liriomyza trifolii, can be controlled.
Pests of the type mentioned which occur on plants, in particular on useful plants and orna¬ mentals in agriculture, in horticulture and in forestry, or on parts, such as fruit, blossom, foli¬ age, stems, tubers or roots, of such plants can be controlled, i.e. checked or destroyed, in particular using the composition according to the invention, even parts of plants which grow later in some cases being protected against these pests.
The active composition according to the invention can advantageously be employed for pest control in cereals, such as maize or sorghum; in fruit, for example pome, stone and soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, for example strawberries, raspberries and blackberries; in leguminous plants, such as beans, lentils, peas or soya; in oil crops, such as oilseed rape, mustard, poppy, olives, sunflowers, coco¬ nut, Ricinus, cocoa or groundnuts; in gourds, such as pumpkins, cucumbers or melons; in fibre plants, such as cotton, flax, hemp or jute; in citrus fruits, such as oranges, lemons, grapefruits or tangerines; in vegetables, such as spinach, lettuce, asparagus, cabbage spe¬ cies, carrots, onions, tomatoes, potatoes or capsicum; in laurel family plants, such as avo¬ cado, cinnamon or camphor; or in tobacco, nuts, coffee, aubergines, cane sugar, tea, pep¬ per, vines, hops, banana-family plants, natural rubber plants or ornamentals, in particular in maize, sorghum, pome and stone fruit, leguminous plants, gourds, cotton, citrus fruits, vegetables, aubergines, vines, hops or ornamentals, especially in maize, sorghum, apples, pears, plums, peaches, beans, peas, soya, olives, sunflowers, coconut, cocoa, groundnuts, cucumbers, pumpkins, citrus fruits, cabbage spe¬ cies, tomatoes, potatoes, vines or cotton, preferably in vines, citrus fruit, apples, pears, tomatoes or cotton.
Other fields of use of the active composition according to the invention are the protection of stocks and stores and of material and in the hygiene sector, in particular the protection of domestic animals and productive livestock against pests of the type mentioned.
In particular, it has suφrisingly been found, that the pesticidal activity of the composition ac¬ cording to the invention, if compared with the combined pesticidal activities of the individual compounds (A) and (B) together forming the active ingredient of the instant composition, is not only additive, as can be expected in principle, but also shows a surprising synergistic effect. In this connection, the term "synergistic effect" is neither limited to the pure pesticidal activity against a certain pest species, nor is it necessary, that this term relates at all to the pure pesticidal activity, but this term can relate to any property of the instant composition, which is advantageous, if compared with the combined corresponding properties of the in¬ dividual compounds (A) and (B) together forming the active ingredients of the instant com¬ position. As examples of such advantageous properties of the instant composition there may be mentioned: a broadening in the spectrum of the pesticidal activity towards additional or different pests, for example towards a resistant pest species; a reduction in the rates of application of the compounds (A) and/or (B); a sufficient degree of pest control by means of the instant composition even in cases where the individual compounds (A) and (B) to¬ gether forming the active ingredient of the instant composition are totally ineffective due to their extremely low rates of application; an advantageous behaviour in the case of being formulated and/or applied, for example if being ground, sieved, compressed, emulsified, dissolved, dispersed or sprayed; an improved storage stability; a better light stability; a bet¬ ter heat stability; an advantageous behaviour in the case of being degraded; a better toxi¬ cology profile; an improved ecotoxicological behaviour; other advantages familiar to those skilled in the art.
Depending on the intended aims and given circumstances, the compositions according to the invention are emulsifiable concentrates, suspension concentrates, solutions which can be sprayed or diluted directly, spreadabie pastes, dilute emulsions, wettable powders, solu¬ ble powders, dispersible powders, dusts, granules or capsules in polymeric substances, which comprise the active compounds of the formulae (A) and (B).
The active compounds are employed in these compositions together with at least one of the auxiliaries conventionally used in the art of formulation, such as extenders, for example sol¬ vents or solid carriers, or such as surface-active compounds (surfactants). Solvents can be, for example: non-hydrogenated or partly hydrogenated aromatic hydro¬ carbons, preferably fractions C8 to C12 of alkylbenzenes, such as xylene mixtures, alkylated naphthalenes or tetrahydronaphthalene, aliphatic or cycloaliphatic hydrocarbons, such as paraffins or cyclohexane, alcohols, such as ethanol, propanol or butanol, glycols and ethers and esters thereof, such as propylene glycol, dipropylene glycol ethers, ethylene glycol or ethylene glycol mono-methyl or -ethyl ether, ketones, such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents, such as N-methylpyrrolid-2-one, dimethylsul¬ foxide or N,N-dimethylformamide, water, non-epoxidized or epoxidized plant oils, such as non-epoxidized or epoxidized rapeseed, castor, coconut or soya oil, and silicone oils.
Solid carriers which can be used, for example for dusts and dispersible powders, are as a rule natural rock powders, such as calcite, talc, kaolin, montmorillonite or attapulgite. Highly disperse silicic acids or highly disperse absorbent polymers can also be added to improve the physical properties. Granular adsoφtive granule carriers are porous types, such as pumice, crushed brick, sepiolite or bentonite, and non-absorbent carrier materials are calcite or sand. A large number of granulated materials of inorganic or organic nature, in particular dolomite or comminuted plant residues, can furtheimore be used.
Surfact active compounds are, depending on the nature of the active compound to be for¬ mulated, nonionic, cationic and/or anionic surfactants or surfactant mixtures with good emulsifying, dispersing and wetting properties. The surfactants listed below are to be re¬ garded only as examples; many other surfactants which are conventionally used in the art of formulation and are suitable according to the invention are described in the relevant lit¬ erature.
Nonionic surfactants are, in particular, polyglycolether derivatives of aliphatic or cy¬ cloaliphatic alcohols, saturated or unsaturated fatty acids and alkylphenols, which can com¬ prise 3 to 30 glycol ether groups and 8 to 20 carbon atoms in the (aliphatic) hydrocarbon radical and 6 to 18 carbon atoms in the alkyl radical of the alkylphenols. Water-soluble polyethylene oxide adducts, containing 20 to 250 ethylene glycol ether and 10 to 100 pro¬ pylene glycol ether groups, on polypropylene glycol, ethylenediaminopolypropylene glycol and alkylpolypropylene glycol having 1 to 10 carbon atoms in the alkyl chain are further¬ more suitable. The compounds mentioned usually contain 1 to 5 ethylene glycol units per propylene glycol unit. Examples are nonylphenolpolyethoxyethanols, castor oil polyglycol ether, polypropylene/polyethylene oxide adducts, tributylphenoxypolyethoxyethanol, poly¬ ethylene glycol and octylphenoxypolyethoxyethanol. Fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylenesorbitan- trioleate, are furthermore suitable. The cationic surfactants are, in particular, quaternary ammonium salts which contain, as substituents, at least one alkyl radical having 8 to 22 C atoms and, as further substituents, Iower, non-halogenated or halogenated alkyl, benzyl or Iower hydroxy alkyl radicals. The salts are preferably in the form of halides, methyl-sulfates or ethyl-sulfates. Examples are stearyl-trimethyl-ammonium chloride and benzyl-di-(2-chloroethyl)-ethyl-ammonium bro¬ mide.
Suitable anionic surfactants can be either water-soluble soaps or water-soluble synthetic surface-active compounds. Suitable soaps are, for examples, the alkali metal, alkaline earth metal and substituted or unsubstituted ammonium salts of higher fatty acids (C10-C22), such as the sodium or potassium salts of oleic or stearic acid, or of naturally occurring fatty acid mixtures, which can be obtained, for example, from coconut oil or tall oil; and also the fatty acid methyl-taurine salts. However, synthetic surfactants, in particular fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives or alkylarylsulfonates, are more often used. The fatty sulfonates and -sulfates are as a rule in the form of alkali metal, alkaline earth metal or substituted or unsubstituted ammonium salts and in general contain an alkyl radical having 8 to 22 C atoms, alkyl also including the alkyl moiety of acyl radicals; examples are the sodium or calcium salt of ligninsulfonic acid, of dodecylsulfuric acid ester or of a fatty alcohol sulfate mixture prepared from naturally occurring fatty acids. These also include the salts of the sulfuric acid esters and sulfonic acids of fatty alcohol-ethylene oxide adducts. The sulfonated benzimidazole derivatives preferably contain 2 sulfonic acid groups and a fatty acid radical having about 8 to 22 C atoms. Alkylarylsulfonates are, for example, the sodium, calcium or triethanolammonium salts of dodecylbenzenesulfonic acid, of dibutyl- naphthalenesulfonic acid or of a naphthalenesulfonic acid-formaldehyde condensation product. Corresponding phosphates, such as salts of the phosphoric acid ester of a p- nonylphenol (4-14)-ethylene oxide adduct or phospholipids, are furthermore also suitable.
The compositions as a rule comprise OJ to 99%, in particular OJ to 95%, of a mixture of the active compound of the formula (A) with the active compound of the formula (B), and 1 to 99.9%, in particular 5 to 99,9%, of - at least - one solid or Iiquid auxiliary, and as a rule 0 to 25%, in particular OJ to 20%, of the composition can be surfactants (% is in each case per cent by weight). While concentrated compositions are preferred as commercial goods, the end user as a rule uses dilute compositions which have considerably Iower active com- pound concentrations. Preferred compositions are composed, in particular, as follows (% per cent by weight):
Emulsifiable concentrates: Mixture of (A) and (B): 1 to 90%, preferably 5 to 20% Surfactant: 1 to 30%, preferably 10 to 20 % Solvent: 5 to 98%, preferably 70 to 85%
Dusts:
Mixture of (A) and (B): 0J to 10%, preferably 0J to 1%
Solid carrier 99.9 to 90%, preferably 99.9 to 99%
Suspension concentrates: Mixture of (A) and (B): 5 to 75%, preferably 10 to 50% Water: 94 to 24%, preferably 88 to 30% Surfactant: 1 to 40%, preferably 2 to 30%
Wettable powders: Mixture of (A) and (B): 0.5 to 90%, preferably 1 to 80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 99%, preferably 15 to 98%
Granules:
Mixture of (A) and (B): 0.5 to 30%, preferably 3 to 15%
Solid carrier 99.5 to 70%, preferably 97 to 85%
The compositions according to the invention can also comprise other solid or Iiquid auxilia¬ ries, such as stabilisers, for example nonepoxidized or epoxidized plant oils (for example epoxidized coconut oil, rapeseed oil or soya oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or adhesives, as well as fertilisers or other active compounds for achieving special effects, for example bactericides, fungicides, nema- ticides, molluscicides or herbicides. The compositions according to the invention are prepared in a known manner, for example by grinding, sieving and/or pressing an active compound or the active compound mixtures, for example to a particular particle size, before mixing with the auxiliary or auxiliaries, and by intimate mixing and/or grinding of the active compound mixture with the auxiliary or aux¬ iliaries. The invention therefore also relates to the process for the preparation of the compo¬ sitions.
The invention also relates to the methods of application of the compositions, i.e. the meth¬ ods for controlling pests of the type mentioned, such as - to be chosen according to the in¬ tended aims and given circumstances - spraying, wetting, atomizing, dusting, brushing, dressing, scattering, or pouring, and to the use of the compositions for controlling pests of the type mentioned. Typical rates of concentration are between OJ and 1000 ppm, prefera¬ bly between OJ and 500 ppm of active ingredient. The rate of application can vary within wide limits and depends on the nature of the soil, the type of application (foliar application; seed dressing; application in the seed furrow), the crop plant, the pest to be controlled, the particular prevailing climatic circumstances and other factors determined by the type of ap¬ plication, the time of application and the target crop. The rates of application per hectare are in general 1 to 2000 g of active ingredientompound per hectare, in particular 10 to 1000 g/ha, preferably 20 to 600 g/ha, particularly preferably 20 to 200 g/ha.
A preferred method of application in the field of plant protection is application to the foliage of the plants (foliar application), where the frequency of application and rate of application can depend on the risk of infestation by the particular pest. However, the active compounds can also enter the plants via the root system (systemic action), by steeping the location of the plants with a Iiquid composition or introducing the active compounds into the location of the plants, for example into the soil, in solid form, for example in the form of granules (soil application). In paddy rice crops, such granules can be metered into the flooded rice field.
The compositions according to the invention are also suitable for protection of plant propa¬ gation material, for example, seed, such as fruit, tubers or grains, or plant seedlings, against animal pests. The propagation material can be treated with the composition before placement, for example seed can be dressed before sowing. The active compounds ac¬ cording to the invention can also be applied to seed grains (coating) by either steeping the grains in a Iiquid composition or coating them with a solid composition. The composition can also be applied to the placement location during placement of the propagation material, for example during sowing in the seed furrow. The invention also relates to this treatment method for plant propagation material and the plant propagation material treated in this way.
The following examples serve to illustrate the invention. They do not limit the invention.
Formulation examples (% = Per cent by weight, active compound ratios = weight ratios)
Example F1 : Emulsion concentrates a) b) c)
Active ingredients [ratio of the compounds of the formulae (A) and (B) 1 :1] 25 % 40 % 50 %
Calcium dodecylbenzenesulfonate 5 % 8 % 6 %
Castor oil polyethylene glycol ether
(36 mol of EO) 5 % - -
Tributylphenol polyethylene glycol ether
(30 mol of EO) - 12 % 4 %
Cyclohexanone - 15 % 20 %
Xylene mixture 65 % 25 % 20 %
Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
Example F2: Solutions a) b) c) d)
Active ingredients (10 : 1) 80 % 10 % 5 % 95 %
Ethylene glycol monomethyl ether 20 % - - -
Polyethylene glycol MW 400 - 70 % - -
N-Methyl-2-pyrrolidone - 20 % - -
Epoxidized coconut oil - - 1 % 5 %
Benzene (boiling limits
160-190°C) - - 94 % -
The solutions are suitable for use in the form of tiny drops. Example F3: Granules a) b) C) d)
Active ingredients (1 : 2) 5% 10% 8% 21 %
Kaolin 94% - 79% 54%
Highly disperse silicic acid 1 % - 13% 7%
Attapulgite - 90% - 18%
The active compounds are dissolved together in dichloromethane, the solution is sprayed onto the carrier and the solvent is then evaporated off in vacuo.
Example F4: Dusts a) b)
Active ingredients (5:1) 2% 5%
Highly disperse silicic acid 1 % 5%
Talc 97% -
Kaolin - 90°/c
Ready-to-use dusts are obtained by intimate mixing of the carriers with the active com¬ pounds.
Example F5: Wettable powders a) b) c)
Active ingredients (20 : 1) 25% 50% 75%
Sodium ligninsulfonate 5% 5% -
Sodium lauryl sulfate 3% . 5%
Sodium diisobutylnaphthalene- sulfonate - 6% 10%
Octylphenol polyethylene glycol- ether (7-8 mol of EO) - 2%
Highly disperse silicic acid 5% 10% 10%
Kaolin 62 % 27 % Ό
The active compounds are mixed with the additives and the mixture is ground thoroughly in a suitable mill. Wettable powders which can be diluted with water to give suspensions of any desired concentration are obtained. Example F6: Emulsion concentrate
Active ingredients (50 : 1 ) 10 %
Octylphenol polyethylene glycol ether
(4-5 mol of EO) 3 %
Calcium dodecylbenzenesulfonate 3 %
Castor oil polyglycol ether
(36 mol of EO) 4 %
Cyclohexanone 30 %
Xylene mixture 50 %
Emulsions of any desired concentration can be prepared from this concentrate by dilution with water.
Example F7: Dusts a) b)
Active compound mixture (1 : 2) 5 % 8 %
Talc 95 %
Kaolin . 92 %
Ready-to-use dusts are obtained by mixing the active compounds with the carrier and grinding the mixture on a suitable mill.
Example F8: Extruded granules
Active compound mixture (3 : 1) 10 %
Sodium ligninsulfonate 2 %
Carboxymethylcellulose 1 %
Kaolin 87 %
The active compounds are mixed with the additives and the mixture is ground and mois¬ tened with water. This mixture is extruded and granulated and the granules are then dried in a stream of air.
Example F9: Coated granules Active compound mixture (1 : 1) 3 %
Polyethylene glycol (MW 200) 3 %
Kaolin 94 %
The finely ground active compounds are applied uniformly, in a mixer, to the kaolin mois¬ tened with polyethylene glycol. Dust-free coated granules are obtained in this manner.
Example F10: Suspension concentrate
Active compound mixture (3 : 2) 40 %
Ethylene glycol 10 %
Nonylphenol polyethylene glycol ether
(15 mol of EO) 6 %
Sodium ligninsulfonate 10 %
Carboxymethylcellulose 1 %
37% aqueous formaldehyde solution 0,2 %
Silicone oil in the form of a 75 % aqueous emulsion 0,8 %
Water 32 %
The finely ground active compounds are mixed intimately with additives. A suspension con¬ centrate from which suspensions of any desired concentration can be prepared by dilution with water is obtained in this way.
It is often more practicable to formulate the active compounds of the formulae (A) and (B) individually and then to bring them together in the applicator in the desired mixing ratio as a "tank mix" in water only shortly before application.
Biological examples (% = Per cent by weight, unless stated otherwise)
A pesticidally synergistic effect is always present if the action of the combination of the ac¬ tive compound of the formula (A) with the active compound of the formula (B) is greater than the sum of the action of the active compounds applied individually. For example, the pesticidal action to be expected Ae for a given combination of two pesti¬ cides can be calculated as follows (cf. COLBY, S.R., "Calculating synergistic and antago¬ nistic response of herbicide combinations", Weeds 15, pages 20-22, 1967):
Y ( 100 - X )
Ae = X +
100
where:
X = Per cent mortality under treatment with the compound of the formula (A) at a rate of application of p kg per hectare compared with the untreated control (= 0 %).
Y = Per cent mortality under treatment with the compound of the formula (B) at a rate of application of q kg per hectare compared with the untreated control.
Ae = Expected pesticidal action (per cent mortality compared with the untreated control) after treatment with the compound of the formula (A) and the compound of the formula (B) at a rate of application of p + q kg of active compound per hectare.
If the action actually observed is greater than the action Ae to be expected, synergism ex¬ ists.
The pesticidally synergistic effect of the combinations of the active compound of the formula (A) with the active compound of the formula (B) is demonstrated in the following examples.
Example B1 : Action against Bemisia tabaci
Dwarf bean plants are placed in gauze cages and populated with adults of Bemisia tabaci. After oviposition has taken place, all the adults are removed. 10 days later, the plants with the nymphs on them are sprayed with an aqueous suspension spray mixture which com¬ prises a total amount of 50 ppm of the active ingredients. After a further 14 days, the per cent hatching of the eggs is evaluated in comparison with untreated control set-ups.
In this experiment, the combinations of the active compound of the formula (A) with the ac¬ tive compound of the formula (B) show a synergistic effect. In particular, the combination of 25 ppm of the active compound of the formula (A) with 25 ppm of the active compound of the formula (B) shows a very good effect.
Example B2: Action against Spodoptera littoralis caterpillars
Young soya plants are sprayed with an aqueous emulsion spray mixture which comprises 400 ppm of the active ingredients. After the spray coating has dried on, the soya plants are populated with 10 caterpillars of the third stage of Spodoptera littoralis and placed in a plas¬ tic container. The evaluation is carried out 3 days later. The per centage reduction in the population or the per centage reduction in feeding damage (% action) is determined by comparison of the number of dead caterpillars and the feeding damage on the treated plants to those on untreated plants.
In this experiment, the combinations of the active compound of the formula (A) with the ac¬ tive compound of the formula (B) show a synergistic effect. In particular, the combinations of 200 ppm of the active compound of the formula (A) with 200 ppm of the active compound of the formula (B), and the combination of 300 ppm of the active compound of the formula (A) with 100 ppm of the active compound of the formula (B) show a very good effect.
Example B3: Ovicidal action on Lobesia botrana
Lobesia botrana eggs deposited on filter paper are immersed for a short time in an acetone- water test solution which comprises 400 ppm of the active ingredients to be tested. After the test solution has dried, the eggs are incubated in Petri dishes. After 6 days, the per centage hatching of the eggs is evaluated in comparison with untreated control set-ups (% hatching reduction).
In this experiment, the combinations of the active compound of the formula (A) with the ac¬ tive compound of the formula (B) show a synergistic effect. In particular, the combination of 100 ppm of the active compound of the formula (A) with 300 ppm of the active compound of the formula (B), and the combination of 250 ppm of the active compound of the formula (A) with 150 ppm of the active compound of the formula (B) show a very good effect. Example B4: Ovicidal action on Heliothis virescens
Heliothis virescens eggs deposited on filter paper are immersed for a short time in an ace¬ tone-water test solution which comprises 400 ppm of the active ingredients to be tested. After the test solution has dried, the eggs are incubated in Petri dishes. After 6 days, the percentage hatching of the eggs is evaluated in comparison with untreated control set-ups (% hatching reduction).
In this experiment, the combinations of the active compound of the formula (A) with the ac¬ tive compound of the formula (B) show a synergistic effect. In particular, the combination of 266.6 ppm of the active compound of the formula (A) with 133.3 ppm of the active com¬ pound of the formula (B), and the combination of 150 ppm of the active compound of the formula (A) with 250 ppm of the active compound of the formula (B) show a very good ef¬ fect.
Example B5: Action against Tetranychus urticae
Young bean plants are populated with a mixed population of Tetranychus urticae, and 1 day later are sprayed with an aqueous emulsion spray mixture which comprises 400 ppm of the active compound. The plants are then incubated for 6 days at 25°C and thereafter evalu¬ ated. The percentage reduction in the population (% action) is determined from the com¬ parison of the number of dead eggs, larvae and adults on the treated plants to those on the untreated plants.
In this experiment, the combinations of the active compound of the formula (A) with the ac¬ tive compound of the formula (B) show a synergistic effect. In particular, the combination of 200 ppm of the active compound of the formula (A) with 200 ppm of the active compound of the formula (B), and the combination of 300 ppm of the active compound of the formula (A) with 100 ppm of the active compound of the formula (B) show a very good effect.

Claims

WHAT IS CLAIMED IS:
1. A pesticidal composition, which comprises a combination, which can be varied in terms of amounts, of the pesticidally active compound of the formula
(A, diafenthiuron),
Figure imgf000021_0001
in the free form or in the form of an agrochemically tolerated salt, and of the pesticidally active compound of the formula
(B, tebufenpyrad)
Figure imgf000021_0002
in the free form or in the form of an agrochemically tolerated salt, and at least one auxiliary.
2. A composition according to claim 1 , which comprises the compounds of the formula (A) and of the formula (B) in the free form.
3. A method of controlling pests, which comprises applying a composition as defined in claim 1 to the pests or their environment.
4. A method according to claim 3 of controlling insects of the order Homoptera.
5. A method according to claim 3 of controlling insects of the order Lepidoptera.
6. A method according to claim 3 of controlling insects of the order Thysanoptera.
7. A method according to claim 3 of controlling insects of the order Acarina.
8. A method according to claim 3 of controlling insects of the order Coleoptera.
9. A method according to claim 3 of protecting plant propagation material against the attack by pests, which comprises treating the propagation material or the location of placement of the propagation material with the composition.
10. A process for the preparation of a composition as defined in claim 1, which comprises mixing the active ingredients intimately with the auxiliary or auxiliaries.
11. Plant propagation material treated bythe process described in claim 10.
12. The use of a composition as defined in claim 1 in a method as defined in claim 3.
13. The use of a compound of the formula (A), in the free form or in agrochemically toler¬ ated salt fotm, for the preparation of a composition as defined in claim 1.
14. The use of a compound of the formula (B), in the free form or in agrochemically toler¬ ated salt form, for the preparation of a composition as defined in claim 1.
PCT/EP1996/002859 1995-07-10 1996-07-01 Synergistic pesticidal composition of diafenthiuron and tebufenpyrad WO1997002746A1 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011134822A1 (en) * 2010-04-27 2011-11-03 Syngenta Participations Ag Methods of controlling neonicotinoid resistant aphids

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AU6515896A (en) 1997-02-10
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