WO2008025542A2 - Methods for protecting plants and controlling pests and compositions comprising indoxacarb and neonicotinoid - Google Patents

Methods for protecting plants and controlling pests and compositions comprising indoxacarb and neonicotinoid Download PDF

Info

Publication number
WO2008025542A2
WO2008025542A2 PCT/EP2007/007561 EP2007007561W WO2008025542A2 WO 2008025542 A2 WO2008025542 A2 WO 2008025542A2 EP 2007007561 W EP2007007561 W EP 2007007561W WO 2008025542 A2 WO2008025542 A2 WO 2008025542A2
Authority
WO
WIPO (PCT)
Prior art keywords
plant
propagation material
indoxacarb
plant propagation
pest
Prior art date
Application number
PCT/EP2007/007561
Other languages
French (fr)
Other versions
WO2008025542A3 (en
Inventor
Christoph Grimm
Dieter Hofer
Robert Senn
Domingos Pedroni
Original Assignee
Syngenta Participations Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from EP06018202A external-priority patent/EP1922929A1/en
Application filed by Syngenta Participations Ag filed Critical Syngenta Participations Ag
Publication of WO2008025542A2 publication Critical patent/WO2008025542A2/en
Publication of WO2008025542A3 publication Critical patent/WO2008025542A3/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/38Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof

Definitions

  • the present invention relates to a defined use of indoxcarb or pesticidal combinations thereof.
  • the treatment of plant propagation material is a targeted pesticide application which addresses the need for a reduction of environmental and worker exposure compared to foliar or soil pesticide applications.
  • damage caused by soil dwelling pests, such as corn rootworms, wireworms, false wireworms and white grubs is not always immediately visible because they attack the plant material underground.
  • corn rootworms ⁇ Diabrotica spp. are one of the most economically important corn insects. Methods of managing this include crop rotation away from corn for one year is a highly effective nonchemical control practice for corn rootworms; transgenic corn hybrids with resistance to larval rootworm feeding; biological control with natural enemies such as other insects, mites, nematodes and fungi; and chemical treatment at time of planting with certain insecticies or as seed treatment.
  • indoxacarb has unexpectedly good activity when applied onto a plant propagation material, particularly against soil-dwelling coleopteran pests, such as Diabrotica spp., Agriotes lineatus, Agriotes obscurus, Limonius califomicus, Limonius infuscatus, Conoderus amplicollis, Conoderus falli, Melanotus communis, Somaticus spp., Gonocephalum spp., Melolontha melolontha, Holotrichia serrata, Phyllophaga spp..
  • soil-dwelling coleopteran pests such as Diabrotica spp., Agriotes lineatus, Agriotes obscurus, Limonius califomicus, Limonius infuscatus, Conoderus amplicollis, Conoderus falli, Melanotus communis, Somaticus spp., Gonocephalum spp., Melolontha melolon
  • the present invention provides a method of controlling or preventing damage by one or more soil-dwelling coleopteran pests, such as larvae thereof, on a plant propagation material, a plant, part of a plant and/or plant organ that grow at a later point in time, which comprises applying on the plant propagation material indoxacarb.
  • the present invention provides a method of protecting a plant propagation material, a plant, part of a plant and/or plant organ that grow at a later point in time against one or more soil-dwelling coleopteran pests' damage which comprises applying on the plant propagation material indoxacarb.
  • the present invention also relates to a method which comprises (i) treating a plant propagation material, such as a seed, with indoxacarb, and (ii) planting or sowing the treated propagation material, wherein the treatment protects against one or more soil-dwelling coleopteran pests 'damage of the treated plant propagation material, plant, part of plant and/or plant organ that grow at a later point in time.
  • a plant propagation material such as a seed, with indoxacarb
  • planting or sowing the treated propagation material wherein the treatment protects against one or more soil-dwelling coleopteran pests 'damage of the treated plant propagation material, plant, part of plant and/or plant organ that grow at a later point in time.
  • the present invention concerns a method which comprises (i) treating a plant propagation material, such as a seed, with indoxacarb, and (ii) planting or sowing the treated propagation material, and (iii) achieving protection against one or more soil-dwelling coleopteran pests' damage of the treated plant propagation material, plant, part of plant and/or plant organ that grow at a later point in time.
  • a plant propagation material such as a seed, with indoxacarb
  • planting or sowing the treated propagation material achieving protection against one or more soil-dwelling coleopteran pests' damage of the treated plant propagation material, plant, part of plant and/or plant organ that grow at a later point in time.
  • indoxacarb one or more pesticides selected from additional insecticides, fungicides and nematicides, and one or more customary formulation auxilaries are present in the form of a plant propagation material, preferably seed, treatment composition.
  • a pesticidal combination comprising indoxacarb and one or more pesticides are applied on the plant propagation material, in any desired sequence or simultaneously.
  • indoxacarb When indoxacarb is used in combination with one or more pesticides on a plant propagation material, a synergistically enhanced activity is observed.
  • the enhanced activity can be for example the unexpected enhanced action resulting in lower pathogenic damage and/or pest damage, lower rates of application, or a longer duration of action.
  • the enhanced action is found to show an improvement in the growing characteristics of a plant by, for example, higher than expected control of the pathogenic infestation and/or pest damage, such as Diabrotica spp..
  • the present invention provides a mixture comprising (a) indoxacarb and (b) one or more neonicotinoid compounds selected from the group consisting of acetamiprid, dinotefuran, thiamethoxam, clothianidin and thiocloprid.
  • the neonicotinoid is selected from acetamiprid, dinotefuran and thiamethoxam.
  • the invention provides a method of controlling pests which comprises applying to a pest, to a locus of a pest, to a plant, or to a plant propagation material susceptible to attack by a pest an effective amount of a pesticidal composition comprising the mixture defined in in the second aspect (of aspect B).
  • the present invention further provides a pesticidal composition that includes, in addition to the active ingredients, an insecticidally inert carrier or diluent and, optionally, a surface active agent (SFA; also known as surface active compounds or surfactants herein).
  • SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting).
  • compositions both solid and liquid formulations
  • the ratio of (a):(b) may be from 100:1 to 1 :100, more preferably from 10:1 to 1 :10. Most preferred is a ratio of 1 : 1.
  • the composition is generally used for the control of pests such that the mixture (a) and (b) is applied at a rate of from 0.1g to 10kg per hectare, preferably from 1g to 6kg per hectare, more preferably from 1g to 1 kg per hectare.
  • An improvement in the growing (or growth) characteristics of a plant can manifest in a number of different ways, but ultimately it results in a better product of the plant. It can, for example, manifest in improving the yield and/or vigour of the plant or quality of the harvested product from the plant, which improvement may not be connected to the control of diseases and/or pests.
  • the phrase "improving the yield" of a plant relates to an increase in the yield of a product of the plant by a measurable amount over the yield of the same product of the plant produced under the same conditions, but without the application of the subject method. It is preferred that the yield be increased by at least about 0.5%, more preferred that the increase be at least about 1%, even more preferred is about 2%, and yet more preferred is about 4%, or more.
  • Yield can be expressed in terms of an amount by weight or volume of a product of the plant on some basis. The basis can be expressed in terms of time, growing area, weights of plants produced, amount of a raw material used, or the like.
  • the phrase "improving the vigour" of a plant relates to an increase or improvement of the vigour rating, or the stand (the number of plants per unit of area), or the plant height, or the plant canopy, or the visual appearance (such as greener leaf colour), or the root rating, or emergence, or protein content, or increased tillering, or bigger leaf blade, or less dead basal leaves, or stronger tillers, or less fertilizer needed, or less seeds needed, or more productive tillers, or earlier flowering, or early grain maturity, or less plant verse (lodging), or increased shoot growth, or earlier germination, or any combination of these factors, or any other advantages familiar to a person skilled in the art, by a measurable or noticeable amount over the same factor of the plant produced under the same conditions, but without the application of the subject method.
  • Indoxacarb or pesticidal combination thereof applied or treated on plant propagation material is particularly effective against the larvae of the soil-dwelling coleopteran pests.
  • control of or protection against infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and lsoptera can be obtained.
  • insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and lsoptera
  • pests of the order Lepidoptera are controlled, and in particular Spodoptera sp. such as, for example, Spodoptera littoralis.
  • the term “pesticidal” includes, for example, “insecticidal”, “acaricidal”, “nematicidal” or “molluscicidal”.
  • the term “effective amount” means a quantity of the compound or combination of such compounds that is capable of combating or controlling pests, in particular insects.
  • Examples of the soil-dwelling coleopteran pests are wireworms (Elateridae: Agriotes lineatus, A. obscurus, Limonius califomicus, L. infuscatus, Conoderus amplicollis, C. falli, Melanotus communis), false wireworms (Somaticus sp., Gonocephalus sp.), white grubs (Melolontha melolontha, Holotrichia serrata, Phyllophaga spp.), and Diabrotica insects, and particularly corn rootworm larvae. Examples are Diabrotica spp. (Western, Southern and Northern corn rootworm), for example, D. balteata, D. virgifera, D. undecimpunctata, and D. longicomis.
  • Controlling, preventing or protecting and its inflections, within the context of the present invention, mean reducing any undesired effect, such as
  • - pathogenic such as phytopathogenic, especially fungi, infestation or attack of, and - pathogenic damage or pest damage on, a plant, part of the plant, plant organs or plant propagation material to such a level that an improvement is demonstrated.
  • Indoxacarb and pesticidal combinations thereof can be formulated for a particular use.
  • indoxacarb and pesticidal combination thereof can be formulated for protecting plant propagation materials, for applying to foliage of plants, or for applying to the soil.
  • the type of equipment used for applying the indoxacarb and pesticidal compositions thereof would vary depending on the specific use, and a skilled person would be able to determine the most suitable.
  • a pesticidal composition may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests or plant or plant propagation material (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, or to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.
  • a locus of the pests or plant or plant propagation material such as a habitat of the pests, or a growing
  • composition may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
  • the indoxacarb and pesticidal combinations thereof are formulated for plant propagation material, preferably seed, treatment applications for controlling or preventing damage by pests, which are found in agriculture and forestry, and can particularly damage the plant in the early stages of its development.
  • the present invention also envisages soil application of indoxacarb or a pesticidal combination to control one or more soil-dwelling coleopteran pests.
  • Methods of applying to the soil can be via any suitable method, which ensures that indoxacarb or a pesticidal combination thereof penetrates the soil, for example, nursery tray application, in furrow application, soil drenching, soil injection, drip irrigation, application through sprinklers or central pivot, incorporation into soil (broad cast or in band) are such methods.
  • invention provides a method of controlling or preventing damage by one or more soil-dwelling coleopteran pests in a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time, which comprises applying to the locus of the plant propagation material indoxacarb or a pesticidal combination thereof.
  • the application to the locus can be before planting or sowing, during planting or sowing, after planting or sowing, or any combination thereof.
  • plant propagation material is understood to denote all the generative parts of the plant, such as seeds, which can be used for the multiplication of the latter and vegetative plant material such as cuttings and tubers (for example, potatoes). There may be mentioned, e.g., the seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, parts of plants.
  • Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion, for example, of their roots.
  • Part of plant and plant organ that grow at later point in time are any sections of a plant that develop from a plant propagation material, such as a seed.
  • Part of plant, plant organ, and plant can also benefit from the pathogenic and/or pest damage protection achieved by the application of indoxacarb or a pesticidal combination thereof on to the plant propagation material.
  • certain part of plant and certain plant organ that grow at later point in time can also be considered as plant propagation material, which can themselves be applied (or treated) with indoxacarb or a pesticidal combination thereof; and consequently, the plant, further part of the plant and further plant organ that develop from the treated part of plant and treated plant organ can also benefit from the pathogenic and/or pest damage protection achieved by the application of indoxacarb or a pesticidal combination thereof on to the certain part of plant and certain plant organ.
  • Methods for applying or treating pesticidal active ingredient(s) and mixtures thereof on to plant propagation material, especially seeds, are known in the art, and include dressing, coating, pelleting and soaking application methods of the propagation material.
  • the active ingredients can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful.
  • the seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.
  • the combination is applied or treated on to the plant propagation material by a method such that the germination is not induced; generally seed soaking induces germination because the moisture content of the resulting seed is too high.
  • suitable methods for applying (or treating) a plant propagation material, such as a seed is seed dressing, seed coating or seed pelleting and alike.
  • the plant propagation material is a seed.
  • the seed be in a sufficiently durable state that it incurs no damage during the treatment process.
  • the seed would be a seed that had been harvested from the field; removed from the plant; and separated from any cob, stalk, outer husk, and surrounding pulp or other non-seed plant material.
  • the seed would preferably also be biologically stable to the extent that the treatment would cause no biological damage to the seed. It is believed that the treatment can be applied to the seed at any time between harvest of the seed and sowing of the seed or during the sowing process (seed directed applications).
  • the seed may also be primed either before or after the treatment.
  • Treatment could vary from a thin film (dressing) of the formulation containing the active ingredient(s) on a plant propagation material, such as a seed, where the original size and/or shape are recognizable to an intermediary state (such as a coating) and then to a thicker film (such as pelleting with many layers of different materials (such as carriers, for example, clays; different formulations, such as of other active ingredients; polymers; and colourants) where the original shape and/or size of the seed is no longer recognisable.
  • a thin film dressing
  • a plant propagation material such as a seed
  • an intermediary state such as a coating
  • a thicker film such as pelleting with many layers of different materials (such as carriers, for example, clays; different formulations, such as of other active ingredients; polymers; and colourants) where the original shape and/or size of the seed is no longer recognisable.
  • the seed treatment occurs to an unsown seed, and the term "unsown seed” is meant to include seed at any period between the harvest of the seed and the sowing of the seed in the ground for the purpose of germination and growth of the plant.
  • Treatment to an unsown seed is not meant to include those practices in which the active ingredient is applied to the soil but would include any application practice that would target the seed during the planting process.
  • the treatment occurs before sowing of the seed so that the sown seed has been pre-treated with, for example, indoxacarb or pesticidal composition thereof.
  • seed coating or seed pelleting are preferred in the treatment of, for example, the compositions, according to the invention.
  • the active ingredient(s) are adhered on to the seed and therefore available for pest and/or disease control.
  • the treated seeds can be stored, handled, sowed and tilled in the same manner as any other active ingredient treated seed.
  • the invention in respect of the second aspect (of aspect B), in an embodiment, relates to a method for controlling insect, especially of the order Lepidoptera, which comprises applying to the insect, to a locus of an insect, to a plant, to a plant propagation material susceptible to attack by the insect or locus thereof an effective amount of the pesticidal composition defined in the second aspect.
  • the present invention is suitable for plants of the crops: cereals (wheat, barley, rye, oats, corn, rice, sorghum, triticale and related crops); beet (sugar beet and fodder beet); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, canola, mustard, sunflowers); cucumber plants (marrows, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); as well as sugar cane, and ornamentals (flowers, shrubs, broad-leaved trees and evergreens, such as conifers).
  • cereals wheat, barley, rye, oats, corn, soybean, triticale, sugar cane and cotton, in particular corn (or maize) and cotton.
  • Suitable target crops also include transgenic crop plants of the foregoing types.
  • the transgenic crop plants used according to the invention are plants, or propagation material thereof, which are transformed by means of recombinant DNA technology in such a way that they are - for instance - capable of synthesizing selectively acting toxins as are known, for example, from toxin-producing invertebrates, especially of the phylum Arthropoda, as can be obtained from Bacillus thuringiensis strains; or as are known from plants, such as lectins; or in the alternative capable of expressing a herbicidal or fungicidal resistance.
  • the invention in respect of the second aspect (of aspect B), in an embodiment, also relates to a method for controlling termites, especially in sugar cane crops.
  • the termites include, in particular, the families Hodotermitidae, Kalotermitidae, Rhinotermitidae and Termitidae.
  • the rates of application (use) of indoxacarb alone or in combination with one or more pesticides vary, for example, according to type of crop, the type of application method, the specific active ingredients in the combination, type of plant propagation material but is such that the active ingredients in the combination is an effective amount to provide the desired enhanced action (such as Diabrotica spp. control) and can be determined by trials.
  • application rates can vary from 0.5 to 1000g / 100kg of seeds of active ingredients.
  • Suitable seed treatment application rates of indoxacarb tend to be 1 - 500, preferably 10 - 400, more preferably 30 - 300, /100kg of seeds, and if one or pesticides are also present, then rates tend to 1 -2500, preferably 1-1000, more preferably 2-950 especially 2 - 800, g/100kg of seeds of any other pesticides
  • Suitable rate for application to the pest, plant or locus of the pest, plant or plant propagation material tends to be such that the mixture (a) and (b) (of aspect B) is applied at a rate of from 0.1g to 10kg per hectare, preferably from 1g to 6kg per hectare, more preferably from 1g to 1 kg per hectare.
  • suitable rates tend to be 0.01 to 1000, preferably 1 to 1000, such as 5 to 1000, especially 5 to 400, g /100 kg of seeds.
  • the weight ratio with a pesticide is selected as to give the desired, for example, synergistic, action.
  • the weight ratio would vary depending on the specific pesticide and how many pesticides are present in the combination.
  • the weight ratio of any two active ingredients is from 100:1 to 1 :100, preferably from 75:1 to 1 :75, more preferably, 50:1 to 1.50, especially 25:1 to 1 :25, advantageously 10:1 to 1 :10.
  • the indoxacarb composition of the first or second aspect may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of the active ingredients).
  • additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of the active ingredients).
  • the indoxacarb composition of the first or second aspect may further comprise one or more additional ingredients having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • additional ingredients having biological activity for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
  • the plant propropation material may be applied together and/or sequentially with further active compounds.
  • These further compounds can be other pesticidal active ingredients, fertilizers or micronutrient donors or other preparations that influence plant growth, such as inoculants, plant inducers (e.g. nod factors).
  • the indoxacarb and active compound(s) can be applied in any desired sequence or simultaneously, whether to the pest, plant, plant propagation material or locus of each thereof.
  • the indoxacarb and further active compound(s) are applied simultaneously.
  • the additional ingredient or further active compound may provide a composition having a broader spectrum of activity or increased persistence at a locus; further synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the composition; or help to overcome or prevent the development of resistance to individual components.
  • the particular additional active ingredient or further active compound will depend upon the intended utility of the composition.
  • the plant propagation material treated by indoxacarb or pesticidal combination thereof is, therefore, resistant to damage, especially against one or more soil-dwelling coleopteran pests; accordingly, the present invention also provides one or more soil-dwelling coleopteran pests resistant plant propagation material which is treated with indoxacarb or pesticidal combination thereof and consequently at least the active ingredient(s) are adhered on the propagation material, such as seed.
  • a single pesticidal active ingredient may have activity in more than one area of pest control, for example, a pesticide may have fungicide, insecticide and nematicide activity.
  • a pesticide may have fungicide, insecticide and nematicide activity.
  • aldicarb is known for insecticide, acaricide and nematicide activity
  • metam is known for insecticide, herbicide, fungicide and nematicide activity
  • thiabendazole and captan can provide nematicide and fungicide activity.
  • pesticides include fungicides, bactericides, insecticides, acaricides and nematicides, for example, triazole derivatives, strobilurins, carbamate (including thiocarbamate), benzimidazoles (thiabendazole), N-trihalomethylthio compounds (captan), substituted benzenes, carboxamides, phenylamides and phenylpyrroles, and mixtures thereof; and neonicotinoids, avermectin and derivatives thereof, carbamates and pyrethroids.
  • Suitable pesticides include the following: a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, beta- cyflurthin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or 5-benzyl-3-furylmethyl-(E)-(1 R,3S)-2,2-dimethyl-
  • Organophosphates such as, profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon; c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, clo
  • Diacylhydrazines such as tebufenozide, chromafenozide or methoxyfenozide; m) Diphenyl ethers, such as diofenolan or pyriproxifen; n) Chlorfenapyr; o) Pymetrozine; p) Chlorfenapyr; q) Spirotetramat, Spiromesifen; r) Flubendiamide; s) Chlorantraniliprole, t) fipronil, and u) neonicotinoids, for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam.
  • pesticides having particular targets may be employed in the mixture or composition, if appropriate for the intended utility of the mixture or composition.
  • selective insecticides for particular crops for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed.
  • insecticides or acaricides specific for particular insect species/stages may also be included (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron).
  • acaricidal ovo-larvicides such as clofentezine, flubenzimine, hexythiazox or tetradifon
  • acaricidal motilicides such as dicofol or propargite
  • acaricides such as bromopropylate or chlorobenzilate
  • growth regulators such as hydra
  • fungicidal compounds which may be included are (E)- ⁇ /-methyl-2-[2-(2,5- dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide (SSF-129), 4-bromo-2-cyano- ⁇ /, ⁇ /-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide, ⁇ -[ ⁇ (S-chloro ⁇ . ⁇ -xylyO ⁇ -methoxyacetamidol- ⁇ -butyrolactone, 4-chloro-2-cyano- ⁇ /, ⁇ /-dimethyl- 5-p-tolylimidazole-1 -sulfonamide (IKF-916, cyamidazosulfamid),
  • the one or more fungicides (II) is selected from one or more of thiram, benalaxyl, benalaxyl-M, fuberdiazole, thiabendazole, azoxystrobin, pyraclostrobin, fluoxastrobin, bitertanol, cyproconazole, difenoconazole, prochloraz, diniconazole, prothioconazole, fluquinconazole, flutriafol, metalaxyl, metalaxyl-M, prothioconazole, tebuconazole, triadimenol, triticonazole, fludioxonil, triazoxide, cyprodinil, carboxin and silthiofam.
  • a preferred pesticide for use in combination with indoxacarb in aspect A is one or more insecticides, such as thiamethoxam, imidacloprid, clothianidin, lamda-cyhalothrin, tefluthrin, ⁇ - cyfluthrin, permethrin, abamectin, fipronil, and spinosad; especially preferred are neonicotinoids, such as thiamethoxam, imidacloprid and clothianidin.
  • insecticides such as thiamethoxam, imidacloprid, clothianidin, lamda-cyhalothrin, tefluthrin, ⁇ - cyfluthrin, permethrin, abamectin, fipronil, and spinosad
  • neonicotinoids such as thiamethoxam, imidacloprid and clothianidin.
  • the insecticide is a neonicotinoid, such as thiamethoxam, imidacloprid, clothianidin, thiacloprid, acetamiprid, dinotefuran or nitenpyram.
  • a preferred ratio by mass between indoxacarb and pesticide, for example, thiamethoxam, especially in respect of aspect A, is from 1 :10 to 10:1 , preferably from 1 :5 to 5:1 , more preferably from 1 :2.5 to 2.5:1 , especially from 1 :1.5 to 1.5:1.
  • composition of aspect B may also be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
  • Suitable herbicides and plant-growth regulators for inclusion in the compositions of aspect B will depend upon the intended target and the effect required.
  • composition of the present invention may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers).
  • fertilisers for example nitrogen-, potassium- or phosphorus-containing fertilisers.
  • Suitable formulation types include granules of fertiliser.
  • Indoxacarb and pesticidal combination thereof may be used either in pure form, i.e., as a solid active ingredient, for example, in a specific particle size, or preferably together with at least one of the auxiliary (also known as adjuvants) customary in formulation technology, such as extenders, e.g., solvents or solid carriers, or surface-active compounds (SFAs or surfactants), in the form of a formulation, in the present invention.
  • the active ingredient(s) are in the form of a formulation composition with one or more of customary formulation auxiliaries.
  • compositions of any aspect may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type.
  • other formulation types may be prepared.
  • one active ingredient is a water insoluble solid and the other a water insoluble liquid
  • the resultant composition is a suspoemulsion (SE) formulation.
  • indoxacarb is applied in combination with one or more pesticides
  • the active ingredients making-up the combination can be applied to the locus (e.g., at the planting site, on the plant propagation material) where control is desired either simultaneously or in succession at short interval, for example on the same day, if desired together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology.
  • the combination is applied simultaneously.
  • indoxacarb and the pesticide(s) can be obtained from a separate formulation source and mixed together (known as a tank-mix, ready- to-apply, spray broth, or slurry), optionally with other active compounds (such as micronutrients, inoculants), or they can be obtained as single formulation mixture source (known as a pre-mix, concentrate, formulated compound (or product)), and optionally mixed together with other active compounds (such as micronutrients, inoculants).
  • the pesticidal combination of the present invention is applied as a composition.
  • the composition is a pre-mix composition (or mixture).
  • the pesticidal combinations also have surprising advantageous properties which can also be described, in a wider sense, as synergistic activity.
  • advantageous properties that may be mentioned are: advantageous behaviour during formulation and/or upon application, for example upon grinding, sieving, emulsifying, dissolving or dispensing; increased storage stability; improved stability to light; more advantageous degradability; improved toxicological and/or ecotoxicological behaviour; or any other advantages familiar to a person skilled in the art.
  • a pre- mix composition or concentrate (or product)
  • the end user will normally employ diluted formulations, optionally also containing one or more other pesticide pre-mixes (known as a tank mix composition (or ready-to-apply, spray broth, or slurry)) for, for example, treatment of the propagation material, but can also use appropriately formulated pre-mix compositions.
  • a tank mix composition or ready-to-apply, spray broth, or slurry
  • the tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.
  • a solvent for example, water
  • an aqueous tank-mix is preferred.
  • examples of plant propagation material protection compositions of invention include tank-mix or slurry pesticidal compositions.
  • mixture or “formulated mixture” as used herein preferably means a “ready- mix” formulation that contains the two or more active ingredients in a single formulation (also known as a pre-mix, concentrate (or product)).
  • the mixture of the invention may be employed in any conventional form.
  • foliar formulation types for pre-mix compositions are: GR: Granules WP: wettable powders WG: water dispersable granules (powders) SG: water soluble granules
  • SE aqueous suspo-emulsion.
  • examples of seed treatment formulation types for pre-mix compositions are:
  • WS wettable powders for seed treatment slurry
  • ES emulsions for seed treatment
  • FS suspension concentrate for seed treatment
  • WG water dispersible granules
  • CS aqueous capsule suspension.
  • formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.
  • the methods of application such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
  • the tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.
  • a solvent for example, water
  • a seed dressing formulation is applied in a manner known per se to the seeds employing the composition of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • suitable seed dressing formulation form e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds.
  • seed dressing formulations are known in the art.
  • a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15 %, active ingredient compounds, and 99.9 to 80 %, especially 99.9 to 85 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20 %, especially 0.1 to 15 %, based on the tank-mix formulation.
  • a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95 %, active ingredient compounds, and 99.9 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %, active ingredient compounds, and 99.75 to 20 %, especially 99 to 25 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.
  • auxiliaries including, for example, a solvent such as water
  • a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, active ingredient compounds, and 99.5 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.
  • a solid or liquid adjuvant including, for example, a solvent such as water
  • seed treatment formulation types for pre-mix compositions are:
  • WS wettable powders for seed treatment slurry
  • FS suspension concentrate for seed treatment
  • WG water dispersible granules
  • CS aqueous capsule suspension.
  • tank-mix compositions examples are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.
  • the tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.
  • Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
  • the formulations are prepared in known manner, e.g., by homogeneously mixing and/or grinding the active ingredients with extenders, e.g., solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).
  • extenders e.g., solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).
  • Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes, phthalates, such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, as well as vegetable oils or epoxidised vegetable oils, such as epoxidised coconut oil or soybean oil; or water.
  • aromatic hydrocarbons preferably the fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes
  • the solid carriers used are normally natural mineral fillers, such as calcite, talcum, kaolin, montmorillonite or attapulgite.
  • calcite talcum
  • kaolin kaolin
  • montmorillonite attapulgite
  • highly dispersed silicic acid or highly dispersed absorbent polymers e.g., calcite, talcum, kaolin, montmorillonite or attapulgite.
  • Suitable granulated adsorptive carriers are porous types, for example pumice, broken brick, sepiolite or bentonite, and suitable nonsorbent carriers are, for example, calcite or sand.
  • pregranulated materials of inorganic or organic nature can be used, e.g., especially dolomite or pulverized plant residues.
  • suitable surface-active compounds are non-ionic, cationic, amphoteric and/or anionic surfactants having good emulsifying, dispersing and wetting properties.
  • surfactants will also be understood as comprising mixtures of surfactants.
  • Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltri methyl ammonium bromide), imidazolines and amine salts.
  • Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di-/sopropyl- and tri-/sopropyl- naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric
  • Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
  • Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
  • alkylene oxides such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof
  • fatty alcohols such as oleyl alcohol or cetyl alcohol
  • alkylphenols such as octylphenol, nonyl
  • Particularly advantageous application-promoting adjuvants are also natural or synthetic phospholipids of the cephalin and lecithin series, e.g., phosphatidylethanolamine, phos- phatidylserine, phosphatidylglycerol and lysolecithin.
  • phospholipids of the cephalin and lecithin series e.g., phosphatidylethanolamine, phos- phatidylserine, phosphatidylglycerol and lysolecithin.
  • Preferred seed treatment pre-mix formulations are aqueous suspension concentrates.
  • the formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful.
  • the seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.
  • a preferred embodiment is a plant propagation material treating (or protecting) composition, wherein said plant propagation material protecting composition comprises additionally a colouring agent.
  • the plant propagation material protecting composition or mixture may also comprise at least one polymer from water-soluble and water-dispersible film-forming polymers that improve the adherence of the active ingredients to the treated plant propagation material, which polymer generally has an average molecular weight of at least 10,000 to about 100,000.
  • indoxacarb or a pesticidal combination thereof is a plant propagation material, preferably seed, treating pre-mix composition.
  • active ingredient denoting indoxacarb or a combination thereof with another pesticide(s).
  • Wettable powders a) b) C) active ingredient 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate - 6 % 10 % phenol polyethylene glycol ether - 2 % -
  • Kaolin 62 % 27 % The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
  • Powders for dry seed treatment a) b) c) active ingredient 25 % 50 % 75 % light mineral oil 55 %% 55 %% 5 % highly dispersed silicic acid 5 % 5 %
  • the active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
  • Emulsifiable concentrate active ingredient 10 % octylphenol polyethylene glycol ether 3 %
  • Emulsions of any required dilution which can be used in plant protection, can be obtained from this concentrate by dilution with water.
  • Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
  • Kaolin 82 % The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air. Coated granules
  • Active ingredient 8 polyethylene glycol (mol. wt. 200) 3 %
  • the finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
  • Carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • Flowable concentrate for seed treatment active ingredient 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 % 1 ,2-benzisothiazolin-3-one (in the form of a 20% solution in 0 .5 % water) monoazo-pigment calcium salt 5 % Silicone oil (in the form of a 75 % emulsion in water) 0 .2 % Water 45 .3 %
  • the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water.
  • living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
  • either straight or diluted plant propagation material can be treated and protected against damage, for example, from pests and/or pathogen(s), by, for example, spraying, pouring or immersing.
  • indoxacarb and pesticidal combinations thereof are distinguished by the fact that they are especially well tolerated by plants and are environmentally friendly.
  • indoxacarb or pesticidal combinations thereof can also be used to treat stored products, such as grain, for protection against pathogens and/or pests.
  • indoxacarb as well as the structures of other pesticides (e.g., fungicides, insecticides, nematicides) can be found in the e-Pesticide Manual, version 3.1 , 13th Edition, Ed. CDC Tomlin, British Crop Protection Council, 2004-05.
  • pesticides e.g., fungicides, insecticides, nematicides
  • Example 1 Maize seeds are treated with Indoxacarb at rate of 0.01 , 0.03, 0.1 , and 0.3 mg a.i. /seed. The seeds are sown into 9-cm pots filled with 280 ml. of soil. After placing the seeds on the soil surface they are covered with 50 ml. of soil. Before and during the bioassays, the plants are grown in greenhouse chambers at 25 0 C during daytime, 23 0 C during night, 50-60 % rH, a 14- hour photoperiod and artificial lighting when natural light fell below 20 kLux. After sowing, the pots are transferred to the greenhouse chambers, set up in a random fashion and are irrigated as necessary from above.
  • the pots are sealed at the bottom by placing them into a plastic Petri dish filled with moist plaster of Paris.
  • the plants are cut back to 15 cm height and covered with an acrylic cylinder.
  • the test organism i.e. D. balteata larvae
  • the cylinders are closed with a plastic mesh at the apex.
  • Each treatment group is replicated 5 times. Each replicate contains 5 plants and 5 larvae.
  • Table below shows the observed corrected mortality of corn root worm larvae to indoxacarb (Abbott W. S. (1925) A method of computing the effectiveness of an insecticide. Journal of Economic Entomology 18: 265-267).
  • Example 2 Maize seeds are also treated with thiamethoxam alone at rate of 0.1 mg a.i. /seed and a mixture of thiamethoxam and indoxacarb at the rates indicated in the Table below.
  • the seeds are sown into 9-cm pots filled with 280 mL of soil. After placing the seeds on the soil surface they are covered with 50 mL of soil.
  • the plants are grown in greenhouse chambers at 25 0 C during daytime, 23 0 C during night, 50-60 % rH, a 14-hour photoperiod and artificial lighting when natural light fell below 20 kLux.
  • the pots are transferred to the greenhouse chambers, set up in a random fashion and are irrigated as necessary from above. After 14 days, the pots are sealed at the bottom by placing them into a plastic Petri dish filled with moist plaster of Paris. The plants are cut back to 15 cm height and covered with an acrylic cylinder. After introducing the test organism (i.e. D. balteata larvae), the cylinders are closed with a plastic mesh at the apex. Each treatment group is replicated 5 times. Each replicate contains 5 plants and 5 larvae. Table below shows the observed corrected mortality of D. balteata larvae to indoxcarb, thiamethoxam and the combination thereof and the expected mortality for the combination according to Colby (Colby S. R. (1967) Calculating synergistic and antagonistic responses of herbicide combinations. Weeds 15: 20- 221

Abstract

A method of controlling or preventing damage by one or more soil-dwelling coleopteran pests, such as larvae thereof, in a plant propagation material, a plant, part of a plant and/or plant organ that grow at a later point in time, which comprises applying on the plant propagation material an effective amount of indoxacarb. Also made available is a mixture comprising: a) indoxacarb and b) one or more defined neonicotinoid compounds.

Description

INDOXACARB and NEONICOTINOID MIXTURES THEREOF
The present invention relates to a defined use of indoxcarb or pesticidal combinations thereof.
The biological properties of known compounds and combinations are not entirely satisfactory in the areas of pest control, phytotoxicity, and environmental and worker exposure, for example. In particular, in the instance a pest has become, or risks becoming resistant to the previously known combinations, improved methods of control or prevention are sought.
The treatment of plant propagation material is a targeted pesticide application which addresses the need for a reduction of environmental and worker exposure compared to foliar or soil pesticide applications. In particular, damage caused by soil dwelling pests, such as corn rootworms, wireworms, false wireworms and white grubs is not always immediately visible because they attack the plant material underground.
For example, corn rootworms {Diabrotica spp.) are one of the most economically important corn insects. Methods of managing this include crop rotation away from corn for one year is a highly effective nonchemical control practice for corn rootworms; transgenic corn hybrids with resistance to larval rootworm feeding; biological control with natural enemies such as other insects, mites, nematodes and fungi; and chemical treatment at time of planting with certain insecticies or as seed treatment.
There is a continuing need to provide pesticidal solutions, which provide improved, for example, biological properties, especially for controlling pests.
It has now been found that indoxacarb has unexpectedly good activity when applied onto a plant propagation material, particularly against soil-dwelling coleopteran pests, such as Diabrotica spp., Agriotes lineatus, Agriotes obscurus, Limonius califomicus, Limonius infuscatus, Conoderus amplicollis, Conoderus falli, Melanotus communis, Somaticus spp., Gonocephalum spp., Melolontha melolontha, Holotrichia serrata, Phyllophaga spp..
Aspect A:
Accordingly, in a first aspect, the present invention provides a method of controlling or preventing damage by one or more soil-dwelling coleopteran pests, such as larvae thereof, on a plant propagation material, a plant, part of a plant and/or plant organ that grow at a later point in time, which comprises applying on the plant propagation material indoxacarb.
In a further aspect, the present invention provides a method of protecting a plant propagation material, a plant, part of a plant and/or plant organ that grow at a later point in time against one or more soil-dwelling coleopteran pests' damage which comprises applying on the plant propagation material indoxacarb.
The present invention also relates to a method which comprises (i) treating a plant propagation material, such as a seed, with indoxacarb, and (ii) planting or sowing the treated propagation material, wherein the treatment protects against one or more soil-dwelling coleopteran pests 'damage of the treated plant propagation material, plant, part of plant and/or plant organ that grow at a later point in time.
Further, the present invention concerns a method which comprises (i) treating a plant propagation material, such as a seed, with indoxacarb, and (ii) planting or sowing the treated propagation material, and (iii) achieving protection against one or more soil-dwelling coleopteran pests' damage of the treated plant propagation material, plant, part of plant and/or plant organ that grow at a later point in time.
In a further aspect of the invention, indoxacarb, one or more pesticides selected from additional insecticides, fungicides and nematicides, and one or more customary formulation auxilaries are present in the form of a plant propagation material, preferably seed, treatment composition.
In an embodiment of each aspect of the first aspect (of aspect A), a pesticidal combination comprising indoxacarb and one or more pesticides are applied on the plant propagation material, in any desired sequence or simultaneously.
When indoxacarb is used in combination with one or more pesticides on a plant propagation material, a synergistically enhanced activity is observed.
The enhanced activity can be for example the unexpected enhanced action resulting in lower pathogenic damage and/or pest damage, lower rates of application, or a longer duration of action. In the instance of agriculture, the enhanced action is found to show an improvement in the growing characteristics of a plant by, for example, higher than expected control of the pathogenic infestation and/or pest damage, such as Diabrotica spp..
It has also been found that combinations of indoxacarb and one or more neonicotinoid pesticides exhibit a synergistic effect in controlling pests, especially certain insects.
Apect B:
Accordingly, in a second aspect the present invention provides a mixture comprising (a) indoxacarb and (b) one or more neonicotinoid compounds selected from the group consisting of acetamiprid, dinotefuran, thiamethoxam, clothianidin and thiocloprid.
In an embodiment of the second aspect, the neonicotinoid is selected from acetamiprid, dinotefuran and thiamethoxam.
In a further aspect, the invention provides a method of controlling pests which comprises applying to a pest, to a locus of a pest, to a plant, or to a plant propagation material susceptible to attack by a pest an effective amount of a pesticidal composition comprising the mixture defined in in the second aspect (of aspect B).
In order to apply the mixture of the second aspect to a pest, a locus of pest, a plant, plant propagation material susceptible to attack by a pest or locus thereof the present invention further provides a pesticidal composition that includes, in addition to the active ingredients, an insecticidally inert carrier or diluent and, optionally, a surface active agent (SFA; also known as surface active compounds or surfactants herein). SFAs are chemicals which are able to modify the properties of an interface (for example, liquid/solid, liquid/air or liquid/liquid interfaces) by lowering the interfacial tension and thereby leading to changes in other properties (for example dispersion, emulsification and wetting). It is preferred that all compositions (both solid and liquid formulations) comprise, by weight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%, of mixture (a) and (b). For example, the ratio of (a):(b) may be from 100:1 to 1 :100, more preferably from 10:1 to 1 :10. Most preferred is a ratio of 1 : 1. The composition is generally used for the control of pests such that the mixture (a) and (b) is applied at a rate of from 0.1g to 10kg per hectare, preferably from 1g to 6kg per hectare, more preferably from 1g to 1 kg per hectare. An improvement in the growing (or growth) characteristics of a plant can manifest in a number of different ways, but ultimately it results in a better product of the plant. It can, for example, manifest in improving the yield and/or vigour of the plant or quality of the harvested product from the plant, which improvement may not be connected to the control of diseases and/or pests.
As used herein the phrase "improving the yield" of a plant relates to an increase in the yield of a product of the plant by a measurable amount over the yield of the same product of the plant produced under the same conditions, but without the application of the subject method. It is preferred that the yield be increased by at least about 0.5%, more preferred that the increase be at least about 1%, even more preferred is about 2%, and yet more preferred is about 4%, or more. Yield can be expressed in terms of an amount by weight or volume of a product of the plant on some basis. The basis can be expressed in terms of time, growing area, weights of plants produced, amount of a raw material used, or the like.
As used herein the phrase "improving the vigour" of a plant relates to an increase or improvement of the vigour rating, or the stand (the number of plants per unit of area), or the plant height, or the plant canopy, or the visual appearance (such as greener leaf colour), or the root rating, or emergence, or protein content, or increased tillering, or bigger leaf blade, or less dead basal leaves, or stronger tillers, or less fertilizer needed, or less seeds needed, or more productive tillers, or earlier flowering, or early grain maturity, or less plant verse (lodging), or increased shoot growth, or earlier germination, or any combination of these factors, or any other advantages familiar to a person skilled in the art, by a measurable or noticeable amount over the same factor of the plant produced under the same conditions, but without the application of the subject method.
Indoxacarb or pesticidal combination thereof applied or treated on plant propagation material is particularly effective against the larvae of the soil-dwelling coleopteran pests.
In the instance of application of the mixture defined in the second aspect (of aspect B) or pesticidal composition thereof to a pest, to a locus of a pest, to a plant, to a plant propagation material or locus thereof, control of or protection against infestations of insect pests such as Lepidoptera, Diptera, Hemiptera, Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera, Hymenoptera and lsoptera can be obtained. In a preferred embodiment pests of the order Lepidoptera are controlled, and in particular Spodoptera sp. such as, for example, Spodoptera littoralis.
The term "pesticidal" includes, for example, "insecticidal", "acaricidal", "nematicidal" or "molluscicidal". The term "effective amount" means a quantity of the compound or combination of such compounds that is capable of combating or controlling pests, in particular insects.
Examples of the soil-dwelling coleopteran pests are wireworms (Elateridae: Agriotes lineatus, A. obscurus, Limonius califomicus, L. infuscatus, Conoderus amplicollis, C. falli, Melanotus communis), false wireworms (Somaticus sp., Gonocephalus sp.), white grubs (Melolontha melolontha, Holotrichia serrata, Phyllophaga spp.), and Diabrotica insects, and particularly corn rootworm larvae. Examples are Diabrotica spp. (Western, Southern and Northern corn rootworm), for example, D. balteata, D. virgifera, D. undecimpunctata, and D. longicomis.
Controlling, preventing or protecting and its inflections, within the context of the present invention, mean reducing any undesired effect, such as
- pathogenic, such as phytopathogenic, especially fungi, infestation or attack of, and - pathogenic damage or pest damage on, a plant, part of the plant, plant organs or plant propagation material to such a level that an improvement is demonstrated.
Indoxacarb and pesticidal combinations thereof can be formulated for a particular use. Preferably, indoxacarb and pesticidal combination thereof can be formulated for protecting plant propagation materials, for applying to foliage of plants, or for applying to the soil. The type of equipment used for applying the indoxacarb and pesticidal compositions thereof would vary depending on the specific use, and a skilled person would be able to determine the most suitable.
A pesticidal composition may be applied by any of the known means of applying pesticidal compounds. For example, it may be applied, formulated or unformulated, to the pests or to a locus of the pests or plant or plant propagation material (such as a habitat of the pests, or a growing plant liable to infestation by the pests) or to any part of the plant, including the foliage, stems, branches or roots, or to the seed before it is planted or to other media in which plants are growing or are to be planted (such as soil surrounding the roots, the soil generally, paddy water or hydroponic culture systems), directly or it may be sprayed on, dusted on, applied by dipping, applied as a cream or paste formulation, applied as a vapour or applied through distribution or incorporation of a composition (such as a granular composition or a composition packed in a water-soluble bag) in soil or an aqueous environment.
The composition may also be injected into plants or sprayed onto vegetation using electrodynamic spraying techniques or other low volume methods, or applied by land or aerial irrigation systems.
Advantageously, the indoxacarb and pesticidal combinations thereof, especially in respect of aspect A, are formulated for plant propagation material, preferably seed, treatment applications for controlling or preventing damage by pests, which are found in agriculture and forestry, and can particularly damage the plant in the early stages of its development.
Further, the present invention also envisages soil application of indoxacarb or a pesticidal combination to control one or more soil-dwelling coleopteran pests. Methods of applying to the soil can be via any suitable method, which ensures that indoxacarb or a pesticidal combination thereof penetrates the soil, for example, nursery tray application, in furrow application, soil drenching, soil injection, drip irrigation, application through sprinklers or central pivot, incorporation into soil (broad cast or in band) are such methods.
Accordingly, in an aspect, invention provides a method of controlling or preventing damage by one or more soil-dwelling coleopteran pests in a plant propagation material, a plant, parts of a plant and/or plant organs that grow at a later point in time, which comprises applying to the locus of the plant propagation material indoxacarb or a pesticidal combination thereof. The application to the locus can be before planting or sowing, during planting or sowing, after planting or sowing, or any combination thereof.
The benefit from the invention can also be achieved either by (i) treating plant propagation material with indoxacarb or a pesticidal combinaton thereof or (ii) applying to the locus where control is desired, generally the planting site, indoxacarb or a pesticidal combinaton thereof, or both (i) and (ii). The term "plant propagation material" is understood to denote all the generative parts of the plant, such as seeds, which can be used for the multiplication of the latter and vegetative plant material such as cuttings and tubers (for example, potatoes). There may be mentioned, e.g., the seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, parts of plants.
Germinated plants and young plants, which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants may be protected before transplantation by a total or partial treatment by immersion, for example, of their roots.
Part of plant and plant organ that grow at later point in time are any sections of a plant that develop from a plant propagation material, such as a seed. Part of plant, plant organ, and plant can also benefit from the pathogenic and/or pest damage protection achieved by the application of indoxacarb or a pesticidal combination thereof on to the plant propagation material. In an embodiment, certain part of plant and certain plant organ that grow at later point in time can also be considered as plant propagation material, which can themselves be applied (or treated) with indoxacarb or a pesticidal combination thereof; and consequently, the plant, further part of the plant and further plant organ that develop from the treated part of plant and treated plant organ can also benefit from the pathogenic and/or pest damage protection achieved by the application of indoxacarb or a pesticidal combination thereof on to the certain part of plant and certain plant organ.
Methods for applying or treating pesticidal active ingredient(s) and mixtures thereof on to plant propagation material, especially seeds, are known in the art, and include dressing, coating, pelleting and soaking application methods of the propagation material.
The active ingredients can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.
In a preferred embodiment, the combination is applied or treated on to the plant propagation material by a method such that the germination is not induced; generally seed soaking induces germination because the moisture content of the resulting seed is too high. Accordingly, examples of suitable methods for applying (or treating) a plant propagation material, such as a seed, is seed dressing, seed coating or seed pelleting and alike.
It is preferred that the plant propagation material is a seed. Although it is believed that the present method can be applied to a seed in any physiological state, it is preferred that the seed be in a sufficiently durable state that it incurs no damage during the treatment process. Typically, the seed would be a seed that had been harvested from the field; removed from the plant; and separated from any cob, stalk, outer husk, and surrounding pulp or other non-seed plant material. The seed would preferably also be biologically stable to the extent that the treatment would cause no biological damage to the seed. It is believed that the treatment can be applied to the seed at any time between harvest of the seed and sowing of the seed or during the sowing process (seed directed applications). The seed may also be primed either before or after the treatment.
Even distribution of the active ingredients and adherence thereof to the seeds is desired during propagation material treatment. Treatment could vary from a thin film (dressing) of the formulation containing the active ingredient(s) on a plant propagation material, such as a seed, where the original size and/or shape are recognizable to an intermediary state (such as a coating) and then to a thicker film (such as pelleting with many layers of different materials (such as carriers, for example, clays; different formulations, such as of other active ingredients; polymers; and colourants) where the original shape and/or size of the seed is no longer recognisable.
The seed treatment occurs to an unsown seed, and the term "unsown seed" is meant to include seed at any period between the harvest of the seed and the sowing of the seed in the ground for the purpose of germination and growth of the plant.
Treatment to an unsown seed is not meant to include those practices in which the active ingredient is applied to the soil but would include any application practice that would target the seed during the planting process.
Preferably, the treatment occurs before sowing of the seed so that the sown seed has been pre-treated with, for example, indoxacarb or pesticidal composition thereof. In particular, seed coating or seed pelleting are preferred in the treatment of, for example, the compositions, according to the invention. As a result of the treatment, the active ingredient(s) are adhered on to the seed and therefore available for pest and/or disease control.
The treated seeds can be stored, handled, sowed and tilled in the same manner as any other active ingredient treated seed.
The invention in respect of the second aspect (of aspect B), in an embodiment, relates to a method for controlling insect, especially of the order Lepidoptera, which comprises applying to the insect, to a locus of an insect, to a plant, to a plant propagation material susceptible to attack by the insect or locus thereof an effective amount of the pesticidal composition defined in the second aspect.
The present invention is suitable for plants of the crops: cereals (wheat, barley, rye, oats, corn, rice, sorghum, triticale and related crops); beet (sugar beet and fodder beet); leguminous plants (beans, lentils, peas, soybeans); oil plants (rape, canola, mustard, sunflowers); cucumber plants (marrows, cucumbers, melons); fibre plants (cotton, flax, hemp, jute); vegetables (spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika); as well as sugar cane, and ornamentals (flowers, shrubs, broad-leaved trees and evergreens, such as conifers). Especially suitable plants are wheat, barley, rye, oats, corn, soybean, triticale, sugar cane and cotton, in particular corn (or maize) and cotton.
Suitable target crops also include transgenic crop plants of the foregoing types. The transgenic crop plants used according to the invention are plants, or propagation material thereof, which are transformed by means of recombinant DNA technology in such a way that they are - for instance - capable of synthesizing selectively acting toxins as are known, for example, from toxin-producing invertebrates, especially of the phylum Arthropoda, as can be obtained from Bacillus thuringiensis strains; or as are known from plants, such as lectins; or in the alternative capable of expressing a herbicidal or fungicidal resistance. Examples of such toxins, or transgenic plants which are capable of synthesizing such toxins, have been disclosed, for example, in EP-A-O 374 753, WO 93/07278, WO 95/34656, EP-A-O 427 529 and EP-A-451 878 and are incorporated by reference in the present application. The invention in respect of the second aspect can further be suitable for application in pasture land to control the pest(s) damaging the vegetation therein.
The invention in respect of the second aspect (of aspect B), in an embodiment, also relates to a method for controlling termites, especially in sugar cane crops. The termites include, in particular, the families Hodotermitidae, Kalotermitidae, Rhinotermitidae and Termitidae.
The rates of application (use) of indoxacarb alone or in combination with one or more pesticides vary, for example, according to type of crop, the type of application method, the specific active ingredients in the combination, type of plant propagation material but is such that the active ingredients in the combination is an effective amount to provide the desired enhanced action (such as Diabrotica spp. control) and can be determined by trials.
Generally for seed treatment, application rates can vary from 0.5 to 1000g / 100kg of seeds of active ingredients.
Suitable seed treatment application rates of indoxacarb tend to be 1 - 500, preferably 10 - 400, more preferably 30 - 300, /100kg of seeds, and if one or pesticides are also present, then rates tend to 1 -2500, preferably 1-1000, more preferably 2-950 especially 2 - 800, g/100kg of seeds of any other pesticides
Suitable rate for application to the pest, plant or locus of the pest, plant or plant propagation material tends to be such that the mixture (a) and (b) (of aspect B) is applied at a rate of from 0.1g to 10kg per hectare, preferably from 1g to 6kg per hectare, more preferably from 1g to 1 kg per hectare.
In the instance of seed treatment application rates of mixture (a) and (b) of aspect B, suitable rates tend to be 0.01 to 1000, preferably 1 to 1000, such as 5 to 1000, especially 5 to 400, g /100 kg of seeds.
In the instance a pesticide is used in combination with indoxacarb, the weight ratio with a pesticide is selected as to give the desired, for example, synergistic, action. In general, the weight ratio would vary depending on the specific pesticide and how many pesticides are present in the combination. Generally, the weight ratio of any two active ingredients is from 100:1 to 1 :100, preferably from 75:1 to 1 :75, more preferably, 50:1 to 1.50, especially 25:1 to 1 :25, advantageously 10:1 to 1 :10.
The indoxacarb composition of the first or second aspect may include one or more additives to improve the biological performance of the composition (for example by improving wetting, retention or distribution on surfaces; resistance to rain on treated surfaces; or uptake or mobility of the active ingredients). Such additives include surface active agents, spray additives based on oils, for example certain mineral oils or natural plant oils (such as soy bean and rape seed oil), and blends of these with other bio-enhancing adjuvants (ingredients which may aid or modify the action of the active ingredients).
Furthermore, the indoxacarb composition of the first or second aspect may further comprise one or more additional ingredients having biological activity, for example micronutrients or compounds having fungicidal activity or which possess plant growth regulating, herbicidal, insecticidal, nematicidal or acaricidal activity.
The plant propropation material may be applied together and/or sequentially with further active compounds. These further compounds can be other pesticidal active ingredients, fertilizers or micronutrient donors or other preparations that influence plant growth, such as inoculants, plant inducers (e.g. nod factors).
In the event indoxacarb is applied in combination with further active compound(s), the indoxacarb and active compound(s) can be applied in any desired sequence or simultaneously, whether to the pest, plant, plant propagation material or locus of each thereof. Preferably, the indoxacarb and further active compound(s) are applied simultaneously.
The additional ingredient or further active compound may provide a composition having a broader spectrum of activity or increased persistence at a locus; further synergise the activity or complement the activity (for example by increasing the speed of effect or overcoming repellency) of the composition; or help to overcome or prevent the development of resistance to individual components. The particular additional active ingredient or further active compound will depend upon the intended utility of the composition. The plant propagation material treated by indoxacarb or pesticidal combination thereof is, therefore, resistant to damage, especially against one or more soil-dwelling coleopteran pests; accordingly, the present invention also provides one or more soil-dwelling coleopteran pests resistant plant propagation material which is treated with indoxacarb or pesticidal combination thereof and consequently at least the active ingredient(s) are adhered on the propagation material, such as seed.
A single pesticidal active ingredient may have activity in more than one area of pest control, for example, a pesticide may have fungicide, insecticide and nematicide activity. Specifically, aldicarb is known for insecticide, acaricide and nematicide activity, while metam is known for insecticide, herbicide, fungicide and nematicide activity, and thiabendazole and captan can provide nematicide and fungicide activity.
Examples of pesticides include fungicides, bactericides, insecticides, acaricides and nematicides, for example, triazole derivatives, strobilurins, carbamate (including thiocarbamate), benzimidazoles (thiabendazole), N-trihalomethylthio compounds (captan), substituted benzenes, carboxamides, phenylamides and phenylpyrroles, and mixtures thereof; and neonicotinoids, avermectin and derivatives thereof, carbamates and pyrethroids.
Examples of suitable pesticides include the following: a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin (in particular lambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, beta- cyflurthin, tefluthrin, fish safe pyrethroids (for example ethofenprox), natural pyrethrin, tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or 5-benzyl-3-furylmethyl-(E)-(1 R,3S)-2,2-dimethyl-
3-(2-oxothiolan-3-ylidenemethyl)cyclopropane carboxylate; b) Organophosphates, such as, profenofos, sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon; c) Carbamates (including aryl carbamates), such as pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur, methomyl or oxamyl; d) Benzoyl ureas, such as diflubenzuron, triflumuron, hexaflumuron, flufenoxuron or chlorfluazuron; e) Organic tin compounds, such as cyhexatin, fenbutatin oxide or azocyclotin; f) Pyrazoles, such as tebufenpyrad and fenpyroximate; g) Macrolides, such as avermectins or milbemycins, for example abamectin, emamectin benzoate, ivermectin, milbemycin, spinosad or azadirachtin; h) Hormones or pheromones; i) Organochlorine compounds such as endosulfan, benzene hexachloride, DDT, chlordane or dieldrin; j) Amidines, such as chlordimeform or amitraz; k) Fumigant agents, such as chloropicrin, dichloropropane, methyl bromide or metam;
I) Diacylhydrazines, such as tebufenozide, chromafenozide or methoxyfenozide; m) Diphenyl ethers, such as diofenolan or pyriproxifen; n) Chlorfenapyr; o) Pymetrozine; p) Chlorfenapyr; q) Spirotetramat, Spiromesifen; r) Flubendiamide; s) Chlorantraniliprole, t) fipronil, and u) neonicotinoids, for example, acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam.
In addition to the major chemical classes of pesticide listed above, other pesticides having particular targets may be employed in the mixture or composition, if appropriate for the intended utility of the mixture or composition. For instance, selective insecticides for particular crops, for example stemborer specific insecticides (such as cartap) or hopper specific insecticides (such as buprofezin) for use in rice may be employed. Alternatively insecticides or acaricides specific for particular insect species/stages may also be included (for example acaricidal ovo-larvicides, such as clofentezine, flubenzimine, hexythiazox or tetradifon; acaricidal motilicides, such as dicofol or propargite; acaricides, such as bromopropylate or chlorobenzilate; or growth regulators, such as hydramethylnon, cyromazine, methoprene, chlorfluazuron or diflubenzuron). Examples of fungicidal compounds which may be included are (E)-Λ/-methyl-2-[2-(2,5- dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide (SSF-129), 4-bromo-2-cyano-Λ/,Λ/-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide, α -[^(S-chloro^.θ-xylyO^-methoxyacetamidol-γ-butyrolactone, 4-chloro-2-cyano-Λ/,Λ/-dimethyl- 5-p-tolylimidazole-1 -sulfonamide (IKF-916, cyamidazosulfamid),
3-5-dichloro-Λ/-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH-7281 , zoxamide), Λ/-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide (MON65500), /V-(1- cyano-1 ,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide (AC382042), Λ/-(2-methoxy-5-pyridyl)-cyclopropane carboxamide, acibenzolar (CGA245704), alanycarb, aldimorph, anilazine, azaconazole, azoxystrobin, benalaxyl, benomyl, biloxazol, bitertanol, bixafen, blasticidin S, bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazim chlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chlorothalonil, chlorozolinate, clozylacon, copper containing compounds such as copper oxychloride, copper oxyquinolate, copper sulphate, copper tallate and Bordeaux mixture, cymoxanil, cyproconazole, cyprodinil, debacarb, di-2-pyridyl disulphide 1 ,1'-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb, difenoconazole, difenzoquat, diflumetorim, O,O-di-/so-propyl-S-benzyl thiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol, diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride, dodemorph, dodine, doguadine, edifenphos, epoxiconazole, ethirimol, ethyl(Z)-Λ/-benzyl-Λ/- ([methyl(methyl-thioethylideneaminooxycarbonyl)amino]thio)-β-alaninate, etridiazole, famoxadone, fenamidone (RPA407213), fenarimol, fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumetover, fluoroimide, fluoxastrobin, fluopyram, fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole, imazalil, imibenconazole, iminoctadine, iminoctadine triacetate, ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanyl butyl carbamate, isoprothiolane, kasugamycin, kresoxim-methyl, LY186054, LY211795, LY248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil, metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin, myclobutanil, neoasozin, nickel dimethyldithiocarbamate, nitrothal-Zsopropyl, nuarimol, ofurace, organomercury compounds, oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin, pefurazoate, penconazole, pencycuron, phenazin oxide, phosetyl-AI, phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxin D, polyram, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, propionic acid, prothioconazole, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil, pyroquilon, pyroxyfur, pyrrolnitrin, quaternary ammonium compounds, quinomethionate, quinoxyfen, quintozene, silthiofam, sipconazole (F-155), sodium pentachlorophenate, spiroxamine, streptomycin, sulphur, tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifluzamid, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thiram, timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph, trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole, validamycin A, vapam, vinclozolin, zineb, ziram and compounds of the formulae below:
or a tautomer of such a compound,
Figure imgf000016_0001
or a tautomer of such a compound, and
Figure imgf000016_0002
CH, or a tautomer of such a compound.
In an embodiment, independent of other embodiments and aspects, the one or more fungicides (II) is selected from one or more of thiram, benalaxyl, benalaxyl-M, fuberdiazole, thiabendazole, azoxystrobin, pyraclostrobin, fluoxastrobin, bitertanol, cyproconazole, difenoconazole, prochloraz, diniconazole, prothioconazole, fluquinconazole, flutriafol, metalaxyl, metalaxyl-M, prothioconazole, tebuconazole, triadimenol, triticonazole, fludioxonil, triazoxide, cyprodinil, carboxin and silthiofam.
A preferred pesticide for use in combination with indoxacarb in aspect A is one or more insecticides, such as thiamethoxam, imidacloprid, clothianidin, lamda-cyhalothrin, tefluthrin, β- cyfluthrin, permethrin, abamectin, fipronil, and spinosad; especially preferred are neonicotinoids, such as thiamethoxam, imidacloprid and clothianidin.
In an embodiment of aspect A, the insecticide is a neonicotinoid, such as thiamethoxam, imidacloprid, clothianidin, thiacloprid, acetamiprid, dinotefuran or nitenpyram.
A preferred ratio by mass between indoxacarb and pesticide, for example, thiamethoxam, especially in respect of aspect A, is from 1 :10 to 10:1 , preferably from 1 :5 to 5:1 , more preferably from 1 :2.5 to 2.5:1 , especially from 1 :1.5 to 1.5:1.
The composition of aspect B may also be mixed with soil, peat or other rooting media for the protection of plants against seed-borne, soil-borne or foliar fungal diseases.
Suitable herbicides and plant-growth regulators for inclusion in the compositions of aspect B will depend upon the intended target and the effect required.
In addition, the composition of the present invention may be used in mixtures with fertilisers (for example nitrogen-, potassium- or phosphorus-containing fertilisers). Suitable formulation types include granules of fertiliser.
Indoxacarb and pesticidal combination thereof may be used either in pure form, i.e., as a solid active ingredient, for example, in a specific particle size, or preferably together with at least one of the auxiliary (also known as adjuvants) customary in formulation technology, such as extenders, e.g., solvents or solid carriers, or surface-active compounds (SFAs or surfactants), in the form of a formulation, in the present invention. Generally, the active ingredient(s) are in the form of a formulation composition with one or more of customary formulation auxiliaries.
Some compositions of any aspect may comprise active ingredients which have significantly different physical, chemical or biological properties such that they do not easily lend themselves to the same conventional formulation type. In these circumstances other formulation types may be prepared. For example, where one active ingredient is a water insoluble solid and the other a water insoluble liquid, it may nevertheless be possible to disperse each active ingredient in the same continuous aqueous phase by dispersing the solid active ingredient as a suspension (using a preparation analogous to that of an SC) but dispersing the liquid active ingredient as an emulsion (using a preparation analogous to that of an EW). The resultant composition is a suspoemulsion (SE) formulation.
Therefore, in the instance indoxacarb is applied in combination with one or more pesticides the active ingredients making-up the combination can be applied to the locus (e.g., at the planting site, on the plant propagation material) where control is desired either simultaneously or in succession at short interval, for example on the same day, if desired together with further carriers, surfactants or other application-promoting adjuvants customarily employed in formulation technology. In a preferred embodiment, the combination is applied simultaneously.
In the event the pesticidal combination is applied simultaneously in the present invention, they may be applied as a composition, in which case indoxacarb and the pesticide(s) can be obtained from a separate formulation source and mixed together (known as a tank-mix, ready- to-apply, spray broth, or slurry), optionally with other active compounds (such as micronutrients, inoculants), or they can be obtained as single formulation mixture source (known as a pre-mix, concentrate, formulated compound (or product)), and optionally mixed together with other active compounds (such as micronutrients, inoculants).
In an embodiment, the pesticidal combination of the present invention is applied as a composition. In a preferred embodiment of the invention, the composition is a pre-mix composition (or mixture).
Alternative to the actual synergistic action with respect to pesticidal activity, the pesticidal combinations also have surprising advantageous properties which can also be described, in a wider sense, as synergistic activity. Examples of such advantageous properties that may be mentioned are: advantageous behaviour during formulation and/or upon application, for example upon grinding, sieving, emulsifying, dissolving or dispensing; increased storage stability; improved stability to light; more advantageous degradability; improved toxicological and/or ecotoxicological behaviour; or any other advantages familiar to a person skilled in the art.
Whereas commercial products will preferably be formulated as concentrates (known as a pre- mix composition (or concentrate (or product)), the end user will normally employ diluted formulations, optionally also containing one or more other pesticide pre-mixes (known as a tank mix composition (or ready-to-apply, spray broth, or slurry)) for, for example, treatment of the propagation material, but can also use appropriately formulated pre-mix compositions.
The tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries. Generally, an aqueous tank-mix is preferred.
Accordingly, examples of plant propagation material protection compositions of invention include tank-mix or slurry pesticidal compositions.
The expression "mixture" or "formulated mixture" as used herein preferably means a "ready- mix" formulation that contains the two or more active ingredients in a single formulation (also known as a pre-mix, concentrate (or product)).
The mixture of the invention may be employed in any conventional form. Examples of foliar formulation types for pre-mix compositions are: GR: Granules WP: wettable powders WG: water dispersable granules (powders) SG: water soluble granules
SL: soluble concentrates
EC: emulsifiable concentrate
EW: emulsions, oil in water ME: micro-emulsion
SC: aqueous suspension concentrate
CS: aqueous capsule suspension
OD: oil-based suspension concentrate, and
SE: aqueous suspo-emulsion.
Whereas, examples of seed treatment formulation types for pre-mix compositions are:
WS: wettable powders for seed treatment slurry
LS: solution for seed treatment
ES: emulsions for seed treatment FS: suspension concentrate for seed treatment
WG: water dispersible granules, and
CS: aqueous capsule suspension.
Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts.
As with the nature of the formulations, the methods of application, such as foliar, drench, spraying, atomizing, dusting, scattering, coating or pouring, are chosen in accordance with the intended objectives and the prevailing circumstances.
The tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.
A seed dressing formulation is applied in a manner known per se to the seeds employing the composition of the invention and a diluent in suitable seed dressing formulation form, e.g. as an aqueous suspension or in a dry powder form having good adherence to the seeds. Such seed dressing formulations are known in the art. Generally, a tank-mix formulation for foliar or soil application comprises 0.1 to 20%, especially 0.1 to 15 %, active ingredient compounds, and 99.9 to 80 %, especially 99.9 to 85 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 20 %, especially 0.1 to 15 %, based on the tank-mix formulation.
Typically, a pre-mix formulation for foliar application comprises 0.1 to 99.9 %, especially 1 to 95 %, active ingredient compounds, and 99.9 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.
Normally, a tank-mix formulation for seed treatment application comprises 0.25 to 80%, especially 1 to 75 %, active ingredient compounds, and 99.75 to 20 %, especially 99 to 25 %, of a solid or liquid auxiliaries (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 40 %, especially 0.5 to 30 %, based on the tank-mix formulation.
Typically, a pre-mix formulation for seed treatment application comprises 0.5 to 99.9 %, especially 1 to 95 %, active ingredient compounds, and 99.5 to 0.1 %, especially 99 to 5 %, of a solid or liquid adjuvant (including, for example, a solvent such as water), where the auxiliaries can be a surfactant in an amount of 0 to 50 %, especially 0.5 to 40 %, based on the pre-mix formulation.
Examples of seed treatment formulation types for pre-mix compositions are:
WS: wettable powders for seed treatment slurry
LS: solution for seed treatment
ES: emulsions for seed treatment
FS: suspension concentrate for seed treatment WG: water dispersible granules, and
CS: aqueous capsule suspension.
Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or a mixture thereof, and dusts. The tank-mix compositions are generally prepared by diluting with a solvent (for example, water) the one or more pre-mix compositions containing different pesticides, and optionally further auxiliaries.
Suitable carriers and adjuvants can be solid or liquid and are the substances ordinarily employed in formulation technology, e.g. natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.
The formulations are prepared in known manner, e.g., by homogeneously mixing and/or grinding the active ingredients with extenders, e.g., solvents, solid carriers and, where appropriate, surface-active compounds (surfactants).
Suitable solvents are: aromatic hydrocarbons, preferably the fractions containing 8 to 12 carbon atoms, e.g. xylene mixtures or substituted naphthalenes, phthalates, such as dibutyl phthalate or dioctyl phthalate, aliphatic hydrocarbons, such as cyclohexane or paraffins, alcohols and glycols and their ethers and esters, such as ethanol, ethylene glycol, ethylene glycol monomethyl or monoethyl ether, ketones, such as cyclohexanone, strongly polar solvents, such as N-methyl-2-pyrrolidone, dimethyl sulfoxide or dimethylformamide, as well as vegetable oils or epoxidised vegetable oils, such as epoxidised coconut oil or soybean oil; or water.
The solid carriers used, e.g., for dusts and dispersible powders, are normally natural mineral fillers, such as calcite, talcum, kaolin, montmorillonite or attapulgite. In order 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, for example pumice, broken brick, sepiolite or bentonite, and suitable nonsorbent carriers are, for example, calcite or sand. In addition, a great number of pregranulated materials of inorganic or organic nature can be used, e.g., especially dolomite or pulverized plant residues.
Depending upon the nature of the active ingredient compounds to be formulated, suitable surface-active compounds (SFAs) are non-ionic, cationic, amphoteric and/or anionic surfactants having good emulsifying, dispersing and wetting properties. The term "surfactants" will also be understood as comprising mixtures of surfactants. Suitable SFAs of the cationic type include quaternary ammonium compounds (for example cetyltri methyl ammonium bromide), imidazolines and amine salts.
Suitable anionic SFAs include alkali metals salts of fatty acids, salts of aliphatic monoesters of sulphuric acid (for example sodium lauryl sulphate), salts of sulphonated aromatic compounds (for example sodium dodecylbenzenesulphonate, calcium dodecylbenzenesulphonate, butylnaphthalene sulphonate and mixtures of sodium di-/sopropyl- and tri-/sopropyl- naphthalene sulphonates), ether sulphates, alcohol ether sulphates (for example sodium laureth-3-sulphate), ether carboxylates (for example sodium laureth-3-carboxylate), phosphate esters (products from the reaction between one or more fatty alcohols and phosphoric acid (predominately mono-esters) or phosphorus pentoxide (predominately di-esters), for example the reaction between lauryl alcohol and tetraphosphoric acid; additionally these products may be ethoxylated), sulphosuccinamates, paraffin or olefine sulphonates, taurates and lignosulphonates.
Suitable SFAs of the amphoteric type include betaines, propionates and glycinates.
Suitable SFAs of the non-ionic type include condensation products of alkylene oxides, such as ethylene oxide, propylene oxide, butylene oxide or mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetyl alcohol) or with alkylphenols (such as octylphenol, nonylphenol or octylcresol); partial esters derived from long chain fatty acids or hexitol anhydrides; condensation products of said partial esters with ethylene oxide; block polymers (comprising ethylene oxide and propylene oxide); alkanolamides; simple esters (for example fatty acid polyethylene glycol esters); amine oxides (for example lauryl dimethyl amine oxide); and lecithins.
Particularly advantageous application-promoting adjuvants are also natural or synthetic phospholipids of the cephalin and lecithin series, e.g., phosphatidylethanolamine, phos- phatidylserine, phosphatidylglycerol and lysolecithin.
Preferred seed treatment pre-mix formulations are aqueous suspension concentrates. The formulation can be applied to the seeds using conventional treating techniques and machines, such as fluidized bed techniques, the roller mill method, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds may also be useful. The seeds may be presized before coating. After coating, the seeds are typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art.
A preferred embodiment is a plant propagation material treating (or protecting) composition, wherein said plant propagation material protecting composition comprises additionally a colouring agent. The plant propagation material protecting composition or mixture may also comprise at least one polymer from water-soluble and water-dispersible film-forming polymers that improve the adherence of the active ingredients to the treated plant propagation material, which polymer generally has an average molecular weight of at least 10,000 to about 100,000.
In a preferred embodiment, indoxacarb or a pesticidal combination thereof is a plant propagation material, preferably seed, treating pre-mix composition.
The Examples which follow serve to illustrate formulations according to the invention, "active ingredient" denoting indoxacarb or a combination thereof with another pesticide(s).
Formulation Examples
Wettable powders a) b) C) active ingredient 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate - 6 % 10 % phenol polyethylene glycol ether - 2 % -
(7-8 mol of ethylene oxide) highly dispersed silicic acid 5 % 10 % 10 %
Kaolin 62 % 27 % The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.
Powders for dry seed treatment a) b) c) active ingredient 25 % 50 % 75 % light mineral oil 55 %% 55 %% 5 % highly dispersed silicic acid 5 % 5 %
Kaolin 65 % 40 %
Talcum - 20
The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.
Emulsifiable concentrate active ingredient 10 % octylphenol polyethylene glycol ether 3 %
(4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3 % castor oil polyglycol ether (35 mol of ethylene oxide) 4 %
Cyclohexanone 30 % xylene mixture 50 %
Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.
Dusts a) b) c)
Active ingredient 5 % 6 % 4 %
Talcum 95 % _ _
Kaolin - 94 % mineral filler - - 96 %
Ready-for-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.
Extruder granules
Active ingredient 15 % sodium lignosulfonate 2 % carboxymethylcellulose 1 %
Kaolin 82 % The active ingredient is mixed and ground with the adjuvants, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air. Coated granules
Active ingredient 8 % polyethylene glycol (mol. wt. 200) 3 %
Kaolin 89 %
The finely ground active ingredient is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.
Suspension concentrate active ingredient 40 % propylene glycol 10 % nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6 %
Sodium lignosulfonate 10 %
Carboxymethylcellulose 1 % silicone oil (in the form of a 75 % emulsion in water) 1 %
Water 32 % The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.
Flowable concentrate for seed treatment active ingredient 40 % propylene glycol 5 % copolymer butanol PO/EO 2 % tristyrenephenole with 10-20 moles EO 2 % 1 ,2-benzisothiazolin-3-one (in the form of a 20% solution in 0 .5 % water) monoazo-pigment calcium salt 5 % Silicone oil (in the form of a 75 % emulsion in water) 0 .2 % Water 45 .3 %
The finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired dilution can be obtained by dilution with water. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion. Using such formulations either straight or diluted plant propagation material can be treated and protected against damage, for example, from pests and/or pathogen(s), by, for example, spraying, pouring or immersing.
The formulations of indoxacarb and pesticidal combinations thereof are distinguished by the fact that they are especially well tolerated by plants and are environmentally friendly.
In an embodiment, indoxacarb or pesticidal combinations thereof can also be used to treat stored products, such as grain, for protection against pathogens and/or pests.
In each aspect and embodiment of the invention, "consisting essentially" and inflections thereof are a preferred embodiment of "comprising" and its inflections, and "consisting of and inflections thereof are a preferred embodiment of "consisting essentially of and its inflections.
Use of a term in a singular form also encompasses that term in plural form and vice a versa.
A description of the structure of indoxacarb as well as the structures of other pesticides (e.g., fungicides, insecticides, nematicides) can be found in the e-Pesticide Manual, version 3.1 , 13th Edition, Ed. CDC Tomlin, British Crop Protection Council, 2004-05.
The compound of formula A (including the different stereoisomeric forms) and its manufacturing processes starting from known and available compounds are described in WO 03/074491.
Details of compound of formula B are disclosed in WO 03/010149 and WO 05/58839.
Details of compound of formula C are disclosed in WO 04/35589. The following Examples are given by way of illustration and not by way of limitation of the invention.
Biological Examples Example 1 Maize seeds are treated with Indoxacarb at rate of 0.01 , 0.03, 0.1 , and 0.3 mg a.i. /seed. The seeds are sown into 9-cm pots filled with 280 ml. of soil. After placing the seeds on the soil surface they are covered with 50 ml. of soil. Before and during the bioassays, the plants are grown in greenhouse chambers at 25 0C during daytime, 23 0C during night, 50-60 % rH, a 14- hour photoperiod and artificial lighting when natural light fell below 20 kLux. After sowing, the pots are transferred to the greenhouse chambers, set up in a random fashion and are irrigated as necessary from above. After 14 days, the pots are sealed at the bottom by placing them into a plastic Petri dish filled with moist plaster of Paris. The plants are cut back to 15 cm height and covered with an acrylic cylinder. After introducing the test organism (i.e. D. balteata larvae), the cylinders are closed with a plastic mesh at the apex. Each treatment group is replicated 5 times. Each replicate contains 5 plants and 5 larvae. Table below shows the observed corrected mortality of corn root worm larvae to indoxacarb (Abbott W. S. (1925) A method of computing the effectiveness of an insecticide. Journal of Economic Entomology 18: 265-267).
Table: Mortality of corn rootworms exposed to maize plants grown from seeds treated with indoxacarb mg/seed Observed, %
0.01 26.1
0.03 34.8
0.1 43.5
0.3 65.2
Example 2 Maize seeds are also treated with thiamethoxam alone at rate of 0.1 mg a.i. /seed and a mixture of thiamethoxam and indoxacarb at the rates indicated in the Table below. The seeds are sown into 9-cm pots filled with 280 mL of soil. After placing the seeds on the soil surface they are covered with 50 mL of soil. Before and during the bioassays, the plants are grown in greenhouse chambers at 25 0C during daytime, 23 0C during night, 50-60 % rH, a 14-hour photoperiod and artificial lighting when natural light fell below 20 kLux. After sowing, the pots are transferred to the greenhouse chambers, set up in a random fashion and are irrigated as necessary from above. After 14 days, the pots are sealed at the bottom by placing them into a plastic Petri dish filled with moist plaster of Paris. The plants are cut back to 15 cm height and covered with an acrylic cylinder. After introducing the test organism (i.e. D. balteata larvae), the cylinders are closed with a plastic mesh at the apex. Each treatment group is replicated 5 times. Each replicate contains 5 plants and 5 larvae. Table below shows the observed corrected mortality of D. balteata larvae to indoxcarb, thiamethoxam and the combination thereof and the expected mortality for the combination according to Colby (Colby S. R. (1967) Calculating synergistic and antagonistic responses of herbicide combinations. Weeds 15: 20- 221
Table: Observed & Expected mortality (%) of corn rootworms exposed to maize plants grown from seeds treated with thiamethoxam and indoxacarb arb, mg/seed Observed, % Expected, %
0.1 0 43.5
0 0.01 26.1
0 0.03 34.8
0 0.1 43.5
0 0.3 65.2
0.1 0.01 82.6 58.2 0.1 0.03 69.6 63.1 0.1 0.1 91.3 68.1 0.1 0.3 82.6 80.3
Example 3
Effect of a mixture of indoxacarb (INDO) and thiamethoxam (THMX) (1 :1 ratio) on Spodoptera littoralis, cotton leafworm, larvae (L2).
ppm = milligrams of active ingredient (=a.i) per litre of spray mixture First experiment:
Table 1 -% mortality of Thiamethoxam (TMX), Indoxacarb (INDO) and a Thiamethoxam + Indoxacarb mixture (ratio 1 : 1) on Spodoptera littoralis (L2).
Figure imgf000030_0001
Second experiment:
Table 2 -% mortality of Thiamethoxam (TMX), Indoxacarb (INDO) and a Thiamethoxam + Indoxacarb mixture (ratio 1 : 1) on Spodoptera littoralis (L2).
Figure imgf000030_0002
Figure imgf000031_0001

Claims

1. A method of controlling or preventing damage by one or more soil-dwelling coleopteran pests, such as larvae thereof, on a plant propagation material, a plant, part of a plant and/or plant organ that grow at a later point in time, which comprises applying on the plant propagation material an effective amount of indoxacarb.
2. The method according to claim 1 wherein the pest is one or more of Diabrotica spp. Agriotes lineatus, Agriotes obscurus, Limonius califomicus, Limonius infuscatus, Conoderus amplicollis, Conoderus falli, Melanotus communis, Somaticus geniculatus, Gonocephalum spp., Melolontha melolontha, Holotrichia serrata, Phyllophaga spp.
3. The method according to claim 2 wherein the pest is Diabrotica is one or more of D. balteata, D. virgifera, D. undecimpunctata, and D. longicornis.
4. The method according to claim 3 wherein the pest is Diabrotica balteata, preferably larvae thereof.
5. The method according to any one of claims 1 to 4 wherein one or more pesticides selected from additional insecticides, fungicides and nematicides are applied on the propagation material in combination with indoxacarb, either in any desired sequence or simultaneously.
6. The method according to claim 4 wherein the pesticide is a neonicotinoid.
7. The method according to claim 6, wherein the neonicotinoid is thiamethoxam, imidacloprid, clothianidin, thiacloprid, acetamiprid, dinotefuran or nitenpyram.
8. The method according to any one of the preceding claims which comprises indoxacarb and thiamethoxam, either in any desired sequence or simultaneously, being applied on the plant propagation material.
9. The method according to claim 8 wherein indoxacarb and thiamethoxam is in the form of a composition.
10. The method according to any one of claims 1 to 9 wherein the plant propagation material is for a plant of the crop of cereals, beets, leguminous plants, oil plants, cucumber plants, fibre plants, vegetables, or ornamentals.
11. A method of protecting a plant propagation material, a plant, part of a plant and/or plant organ that grow at a later point in time against damage by one or more soil-dwelling coleopteran pests, such as larvae thereof, which comprises applying on the plant propagation material an effective amount of indoxacarb.
12. The method according to any one of claims 1 to 11 , wherein the plant propagation material is a seed.
13. A plant propagation material treatment composition comprising indoxacarb, one or more pesticides selected from additional insecticides, fungicides and nematicides, and one or more customary formulation auxilaries.
14. The composition according to claim 13 wherein pesticide is a neonicotinoid.
15. A plant propagation material treated with the composition defined in claims 13 and 14.
16. A method of controlling or preventing damage one or more soil-dwelling coleopteran pests, such as larvae thereof, in a plant propagation material, a plant, part of a plant and/or plant organ that grow at a later point in time, which comprises applying to the locus of the plant propagation material an effective amount of indoxacarb.
17. A mixture comprising (a) indoxacarb and (b) a neonicotinoid compound selected from the group consisting of acetamiprid, dinotefuran and thiamethoxam.
18. The mixture according to claim 17, wherein the weight ratio of (a) to (b) is from 100:1 to 1 :100.
19. The pesticidal composition comprising a mixture according to claim 18 or claim 19 and an insecticidally inert carrier or diluent.
20. The pesticidal composition according to claim 19, further comprising a surface active agent (SFA).
21. The pesticidal composition according to either claim 19 or 20, wherein the pesticidal composition further comprises one or more additional ingredients having biological activity.
22. A method of controlling pests which comprises applying to a pest, to a locus of a pest, to a plant, or to a plant propagation material susceptible to attack by a pest an effective amount of a pesticidal composition according to any one of claims 19 to 21.
23. The method according to claim 22, wherein the pest is an insect.
24. The method according to claim 22, wherein the pest is of the order Lepidoptera.
PCT/EP2007/007561 2006-08-31 2007-08-29 Methods for protecting plants and controlling pests and compositions comprising indoxacarb and neonicotinoid WO2008025542A2 (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP06018202.9 2006-08-31
EP06018202A EP1922929A1 (en) 2006-08-31 2006-08-31 A method of protecting a plant propagation material, a plant, part of a plant and/or plant organ
EP07004253 2007-03-01
EP07004253.6 2007-03-01

Publications (2)

Publication Number Publication Date
WO2008025542A2 true WO2008025542A2 (en) 2008-03-06
WO2008025542A3 WO2008025542A3 (en) 2008-04-17

Family

ID=38984088

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/007561 WO2008025542A2 (en) 2006-08-31 2007-08-29 Methods for protecting plants and controlling pests and compositions comprising indoxacarb and neonicotinoid

Country Status (4)

Country Link
AR (1) AR063699A1 (en)
CL (1) CL2007002517A1 (en)
UY (1) UY30563A1 (en)
WO (1) WO2008025542A2 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101790989A (en) * 2010-04-01 2010-08-04 上海悦联化工有限公司 Pesticide composite containing thiamethoxam and indoxacarb
CN101796959A (en) * 2010-04-16 2010-08-11 陕西美邦农药有限公司 Insecticidal composition containing clothianidin and indoxacarb
CN101999391A (en) * 2010-04-16 2011-04-06 陕西美邦农药有限公司 Indoxacarb-and-thiacloprid-containing insecticidal composition
ES2410358A1 (en) * 2011-12-27 2013-07-01 Sumitomo Chemical Company, Limited Method for protecting corn
EP2206428B1 (en) * 2008-12-22 2017-04-12 Siegfried Mantel Landtechnikproduktion Method for chemical and/or biological combating of plant pests, in particular root pests and diseases of cultivated plants

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0580553A2 (en) * 1992-07-22 1994-01-26 Ciba-Geigy Ag Oxadiazine derivatives
WO2000035277A1 (en) * 1998-12-14 2000-06-22 Syngenta Participations Ag Insecticidal seed coating
WO2000054591A2 (en) * 1999-03-12 2000-09-21 American Cyanamid Company Synergistic insecticidal compositions
WO2002056691A1 (en) * 2001-01-19 2002-07-25 Bayer Cropscience Ag Synergistic pesticide mixtures for the control of animal pests
WO2003070001A1 (en) * 2002-02-21 2003-08-28 Bayer Cropscience Ag Synergistic insecticide mixtures

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1593144A (en) * 2004-07-13 2005-03-16 江苏长青农化股份有限公司 Insecticide

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0580553A2 (en) * 1992-07-22 1994-01-26 Ciba-Geigy Ag Oxadiazine derivatives
WO2000035277A1 (en) * 1998-12-14 2000-06-22 Syngenta Participations Ag Insecticidal seed coating
WO2000054591A2 (en) * 1999-03-12 2000-09-21 American Cyanamid Company Synergistic insecticidal compositions
WO2002056691A1 (en) * 2001-01-19 2002-07-25 Bayer Cropscience Ag Synergistic pesticide mixtures for the control of animal pests
WO2003070001A1 (en) * 2002-02-21 2003-08-28 Bayer Cropscience Ag Synergistic insecticide mixtures

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
BLOT Y ET AL: "Consequence of three types of chemical treatment: Broadcast, localised and seed treatment on reduction rate of wireworms (Agriotes spp) larval population in corn crop" MEDEDELINGEN - FACULTEIT LANDBOUWKUNDIGE EN TOEGEPASTE BIOLOGISCHE WETENSCHAPPEN, UNIVERSITEIT GENT, GENT,, BE, vol. 60, no. 3B, 1995, pages 945-951, XP008088031 ISSN: 1373-7503 *
DATABASE WPI Week 200573 Derwent Publications Ltd., London, GB; AN 2005-704740 XP002467748 & CN 1 593 144 A (JIANGSU CHANGQING AGRIC CHEM CO LTD) 16 March 2005 (2005-03-16) *
PARIMI SRINIVAS ET AL: "Toxicity of insecticide-bait mixtures to insecticide resistant and susceptible western corn rootworms (Coleoptera: Chrysomelidae)." CROP PROTECTION, vol. 22, no. 5, June 2003 (2003-06), pages 781-786, XP002467638 ISSN: 0261-2194 *
WILDE GERALD ET AL: "Seed treatment for control of early-season pests of corn and its effect on yield" JOURNAL OF AGRICULTURAL AND URBAN ENTOMOLOGY, vol. 21, no. 2, April 2004 (2004-04), pages 75-85, XP008088030 ISSN: 1523-5475 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2206428B1 (en) * 2008-12-22 2017-04-12 Siegfried Mantel Landtechnikproduktion Method for chemical and/or biological combating of plant pests, in particular root pests and diseases of cultivated plants
CN101790989A (en) * 2010-04-01 2010-08-04 上海悦联化工有限公司 Pesticide composite containing thiamethoxam and indoxacarb
CN101796959A (en) * 2010-04-16 2010-08-11 陕西美邦农药有限公司 Insecticidal composition containing clothianidin and indoxacarb
CN101999391A (en) * 2010-04-16 2011-04-06 陕西美邦农药有限公司 Indoxacarb-and-thiacloprid-containing insecticidal composition
ES2410358A1 (en) * 2011-12-27 2013-07-01 Sumitomo Chemical Company, Limited Method for protecting corn

Also Published As

Publication number Publication date
UY30563A1 (en) 2008-03-31
WO2008025542A3 (en) 2008-04-17
CL2007002517A1 (en) 2008-04-18
AR063699A1 (en) 2009-02-11

Similar Documents

Publication Publication Date Title
EP2411384B1 (en) Insecticidal compounds
RU2515966C2 (en) Bisamide derivatives and their application as insecticidal compounds
RU2636978C2 (en) Methods of controlling soil pests
CN102803257A (en) Insecticidal Compounds
MX2012010261A (en) Pesticidal mixtures.
US20130317073A1 (en) Methods of pest control in soybean
US20230320357A1 (en) Methods of pest control in soybean
EP2887809B1 (en) Methods of controlling insects
WO2008025542A2 (en) Methods for protecting plants and controlling pests and compositions comprising indoxacarb and neonicotinoid
JP5592353B2 (en) Insecticidal compounds
US9320278B2 (en) Methods of controlling insects
WO2022158265A1 (en) Method, seeds, and composition for controlling insects in crops
US20150189883A1 (en) Methods of controlling insects
WO2013190050A1 (en) Methods of controlling insects
WO2014131837A1 (en) Isoxaline derivatives for use in cotton plants
WO2014019957A2 (en) Methods of pest control in soybean
NZ613413B2 (en) Methods of pest control in soybean
NZ613413A (en) Methods of pest control in soybean
WO2013190046A1 (en) Methods of soil pest control
SA110310519B1 (en) Insecticidal Compounds
NZ700056B2 (en) Methods of pest control in soybean
NZ626702B2 (en) Methods of pest control in soybean

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07801982

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase in:

Ref country code: DE

NENP Non-entry into the national phase in:

Ref country code: RU

122 Ep: pct application non-entry in european phase

Ref document number: 07801982

Country of ref document: EP

Kind code of ref document: A2