WO2024218261A1

WO2024218261A1 - Method and composition for treating plant propagation materials

Info

Publication number: WO2024218261A1
Application number: PCT/EP2024/060646
Authority: WO
Inventors: Benedikt KURTZ; Matthias GABERTHUEEL
Original assignee: Syngenta Crop Protection AG Switzerland
Current assignee: Syngenta Crop Protection AG Switzerland
Priority date: 2023-04-18
Filing date: 2024-04-18
Publication date: 2024-10-24
Anticipated expiration: 2025-10-18

Abstract

The present invention relates to method of controlling, limiting or preventing infestation of an Amaranthaceae plant by an aphid, which comprises applying to a propagation material of the plant a compound of formula (I): (I), and to seed treatment compositions comprising a compound of formula (I).

Description

METHOD AND COMPOSITION FOR TREATING PLANT PROPAGATION MATERIALS

The present invention relates a method for preventing, limiting or controlling infestation of plant propagation materials, in particular seeds, of amaranthacea with aphids and to compositions for the treatment of plant propagation material in order to prevent, limit or control damage caused by aphid pests.

Amaranthaceae is a plant family that belongs to the Caryophyllales order and comprises the subfamilies Betoideae and Chenopodioideae. This plant family is known for containing several economically important crops such as sugar beet (Beta vulgaris ssp. vulgaris var. altissima'), spinach (Spinacia oleracea), and quinoa (Chenopodium quinoa).

As an example of an economically very important crop, sugar beet (Beta vulgaris ssp. vulgaris var. altissima') is a variety of beet that is known specifically for its high sugar content which is extracted from the roots and used to produce sugar. The cultivation of sugar beet began in the 18th century, and it has since become an essential crop in many parts of the world, particularly in Europe and North America.

Today, sugar beet is one of the primary sources of sugar globally, second only to sugarcane. However, while sugar beet is primarily grown for its sugar content, it also has some other uses. For example, the leaves of the plant can be used as livestock feed, and the pulp left over after sugar extraction can be used to produce biofuels or as a soil amendment.

Sugar beet and other Amaranthaceae plants are prone to infestation by various aphids. Aphid damage can manifest in various ways in the plants, such as reduced growth rates, mottled leaves, yellowing, stunted growth, curled leaves, browning, wilting, low yields, and even death. The loss of sap weakens the plant, while the toxic saliva of aphids can harm them. Additionally, aphids often transmit plant viruses to their hosts; for example, the green peach aphid (Myzus persicae) is a generalist feeder and can be found on a wide range of crops, including sugar beets; it causes damage by sucking the sap, and is known to be able to transmit over 100 plant viruses. The beet aphid (Aphis fabae) is one of the most common species of aphids that infest sugar beet; it is a specialist feeder that primarily feeds on sugar beet and related crops, and is known to cause significant yield losses by reducing plant growth and transmitting viruses. In addition, beet aphids can also excrete a sticky substance called honeydew, which can attract other pests like ants and lead to the growth of sooty mould. In sugar beet, aphids can also cause the roots to become misshapen and stunted, leading to reduced yield and quality.

Management of aphid pests on Amaranthaceae such as sugar beet typically involves the use of insecticides, which can be applied either through foliar sprays or as a seed treatment. For example, compounds from the class of neonicotinoids are commonly used to control aphids on plants in the Amaranthaceae family, such as spinach, beets, and quinoa. Neonicotinoid insecticides such as thiamethoxam are effective against a wide range of aphid species and can provide quick and effective control of infestations. Another class of compounds used in the control of aphid pests on Amaranthaceae are so-called ketoenol insecticides. For example, W02006089633A2 and W02010066780A1 describe spiroketalsubstituted cyclic keto-enol compounds that are suitable for use in controlling infestation of various plant species with cotton aphid, green peach aphid and cowpea aphid (Aphis craccivora). However, it is also shown in W02006089633A2 that the use of these spiroketal-substituted cyclic keto-enol compounds as a soil treatment for Amaranthus may result in phytotoxicity towards the plant treated therewith.

There is a continuing need to provide pesticidal compounds and compositions, which provide improved properties, such as increased mortality and/or reduced phytotoxicity, especially for controlling sucking insects, in particular aphids, on plants of the Amaranthaceae family. The benefits may also include an increased safety profile, improved physico-chemical properties, or increased biodegradability.

It has now surprisingly been found that a compound or formula (I)

(CAS 907187-07-9) provides unexpected control, limitation or prevention of damage to a plant caused by aphids when applied as a treatment to plant propagation material. Particularly, it has been found that while maintaining or improving control of aphids, less phytotoxicity is observed when this compound is applied to particularly plant propagation materials such as seeds.

Accordingly, in a first aspect, the present invention relates to a method of controlling, limiting or preventing infestation of an Amaranthaceae plant by aphids, which comprises applying to a propagation material of the plant a compound of formula (I):

or an agrochemically acceptable salt thereof. In a second aspect, the present invention provides a seed treatment composition comprising a compound of formula (I):

or an agrochemically acceptable salt thereof, and one or more auxiliaries and/or diluents.

The compositions are useful in protecting the seeds, during storage, germination and growth from harmful or damaging aphids. Examples of the above mentioned aphids include pea aphid (Acyrthosiphon pisum), cowpea aphid (Aphis craccivora), bean aphid (Aphis fabae), cotton aphid (Aphis gossypii), foxglove aphid (Aulacorthum solani), large rose aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), celery aphid (Cavariella aegopodii), coriander aphid (Hyadaphis coriandri), lettuce aphid (Hyperomyzus lactucae), turnip aphid (Lipaphis erysimi), potato aphid (Macrosiphum euphorbiae), shallot aphid (Myzus ascalonicus), cherry blackfly (Myzus cerasi), green peach aphid (Myzus persicae), sugar beet root aphid (Pemphigus betae), corn leaf aphid (Rhopalosiphum maidis), bird cherry-oat aphid (Rhopalosiphum padi), cereal aphid (Sitobion avenae), black bean aphid (Therioaphis trifolii), and goldenrod aphid (Uroleucon hypochoeridis).

In some embodiments, the Amaranthaceae plant is selected from the Betoideae subfamily.

In some embodiments, the Amaranthaceae plant is selected from the Chenopodioideae subfamily.

Suitable target Amaranthaceae crops are, in particular, amaranth (Amaranthus various species), garden orache (Atriplex hortensis), shiny orache (Atriplex nitens), spear orache (Atriplex patula), halberd-leaved orache (Atriplex portulacoides), spear saltbush (Atriplex prostrata), saltbush (Atriplex spp.), sea beet (Beta vulgaris subsp. maritima), beet root (Beta vulgaris subsp. vulgaris var. conditiva), mangelwurzel (Beta vulgaris subsp. vulgaris var. crassa), sugar beet (Beta vulgaris subsp. vulgaris var. altissima), Swiss chard (Beta vulgaris subsp. vulgaris var. cicla/flavescens), fodder beet (Beta vulgaris subsp. vulgaris var. crassa), Good King Henry (Chenopodium bonus-henricus), strawberry blite (Chenopodium capitatum), strawberry spinach (Chenopodium foliosum), mapleleaved goosefoot (Chenopodium hybridum), nettle-leaved goosefoot (Chenopodium murale), white goosefoot (Chenopodium album), feathered goosefoot (Chenopodium botrys), fig-leaved goosefoot (Chenopodium ficifolium), quinoa (Chenopodium quinoa), goosefoot (Chenopodium spp.), stinking goosefoot (Chenopodium vulvaria), epazote (Chenopodium ambrosioides), many-seeded goosefoot (Chenopodium polyspermum), strawberry goosefoot (Chenopodium chenopodioides), grey goosefoot (Chenopodium glaucum), red goosefoot (Chenopodium rubrum), greater knapweed (Polycnemum majus), common glasswort (Salicornia europaea), redroot pigweed (Amaranthus retroflexus), spinach (Spinacia oleracea), and annual sea-blite (Suaeda maritima). In an embodiment, the Amaranthaceae plant or its propagation material is sugar beet.

Accordingly, in an aspect, the invention relates to a method of controlling, limiting, or preventing infestation of a sugar beet plant by an aphid, which comprises applying to a propagation material of the plant, an insecticidally effective amount of a compound of formula (I):

or an agrochemically acceptable salt thereof.

In an embodiment, the sugar beet is Beta vulgaris subsp. vulgaris var. altissima.

The term "plant propagation material” denotes all generative parts of a plant, for example seeds or vegetative parts of plants such as cuttings and tubers. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and parts of plants.

In an embodiment, the term "plant propagation material” denotes the seeds of a plant.

As used herein, the term "seed" denotes any resting stage of a plant that is physically detached from the vegetative stage of a plant and/or may be stored for prolonged periods of time and/or can be used to re-grow another plant individual of the same species. Here, the term "resting" refers to a state wherein the plant retains viability, within reasonable limits, in spite of the absence of light, water and/or nutrients essential for the vegetative (i.e. non-seed) state. In particular, the term refers to true seeds but does not embrace plant propagules such as suckers, corms, bulbs, fruit, tubers, grains, cuttings and cut shoots.

Besides any reduced phytotoxicity when applied on plant propagation materials, the method and compositions according to the aspects of the invention can also have further surprising advantageous properties. Examples of such advantageous properties that may be mentioned are: more advantageous degradability, improved ecotoxicological behaviour, or improved characteristics of the useful plants including: emergence, crop yields, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigour, and early germination.

The term "seed treatment" generally refers to application of a material to a seed prior to or during the time it is planted in soil to improve the handling characteristics of the seed, protect the seed prior to germination, support the germination and/or support the growth of the resulting plant. Some seed treatments are employed solely for the purpose of improving the handling characteristics or other physical characteristics of seeds, and include no agricultural active ingredients. Other seed treatments bind one or more active ingredients to seeds for various beneficial purposes. For example, seed treatments that include one or more active ingredients are commonly used to ensure uniform stand establishment by protecting against soilborne diseases and insects. Typical examples include the application of pesticides such as fungicides, insecticides and plant growth regulators. Systemic seed treatments may eliminate, or at least reduce the need for, traditional broadcast sprays of foliar fungicides or insecticides for certain early season airborne diseases and insects.

The seed treatment composition can also comprise or may be applied together and/or sequentially with further active compounds. These further compounds can be fertilizers or micronutrient donors or other preparations that influence plant growth, such as inoculants.

The compound of formula (I) is present in an insecticidally-effective amount in the formulation, for example, in an amount of 1% to about 60% by weight, based on the total weight of the seed treatment mixture.

As applied to the plant propagation material, especially seed, rates of 0.03 to 600 g of compound (I) per kg of plant propagation material, preferably from 0.3 to 500 g per kg of plant propagation material, especially seed, are generally sufficient. Typically, the compound of formula (I) is applied in a rate of from 1 to 400 g, 2 to 300 g, 4 to 150 g, 8 to 100 g, 12 to 60 g or 15 to 30 g per kg of plant propagation material, especially seed.

In some embodiments, the seed composition comprising a compound of formula (I) as defined herein comprises 0.03 to 600 g of the compound of formula (I) per kg of seed to be treated, preferably from 0.3 to 500 g per kg of seed to be treated, more preferably 1 to 400 g, 2 to 300 g, 4 to 150 g, 8 to 100 g, 12 to 60 g or 15 to 30 g per kg of seed to be treated.

In certain embodiments, the compound of formula (I) is applied in a rate of from 0.001 to 50 mg per plant propagation material, preferably 0.01 to 20 mg, 0.02 to 15 mg, 0.05 to 10 mg, 0.1 to 5 mg, 0.2 to 2 mg, 0.3 to 1 .5 mg or 0.5 to 1 mg per plant propagation material, especially seed.

In field applications, typically, the compound of formula (I) is applied in a rate of from 0.1 to 2000 g/ha, preferably 1 to 2000 g/ha, 2 to 1500 g/ha, 5 to 1000 g/ha, 10 to 500 g/ha, 20 to 200 g/ha, 30 to 150 g/ha or 50 to 100 g/ha.

Such application rates may apply to pelleted seeds and to naked seeds.

The seed treatment composition may include further components, such as further fungicidal, insecticidal, acaricidal, and/or nematocidal ingredients. In yet further embodiments, the active component further includes other active ingredients.

The seed treatment composition may additionally include non-active ingredients in some amount. For example, the active component may include surfactants, solvents (e.g., water and/or other solvents), thickeners, preservatives (including bactericides and other biocides), humectants, antifreeze ingredients, antifoam ingredients and if appropriate colorants, or other additives.

In order to treat plant propagation material, especially seed, the compounds can be applied to the plant propagation material, either by impregnating the tubers or grains with a liquid formulation of the active ingredients, or by coating them with an already combined wet or dry formulation.

The seed treatment composition can be applied to a seed in a variety of manners conventional in the seed treating art, including but not limited to mixing in a container (e.g., a bottle, bag or tumbler), mechanical application, tumbling, spraying, and immersion, followed by drying. Examples of seed coating techniques and machines that can be employed include fluidized bed techniques, the roller mill method, rotary seed treaters, drum coaters, side vended pan, tumble mixers and spouted beds. The seeds may be pre-sized before coating. In one embodiment, the seed treatment mixture is applied to seeds in a Hege seed treater, which rotates as the formulation is being added to the seeds. Mixing is preferably continued until the seed treatment mixture is distributed uniformly on the seed (i.e., uniform coatings over all of the seeds to be treated and an even coating on each individual seed). The seed treatment mixture can be applied to seeds in a batch treatment process or in a continuous treatment process. In one representative batch treatment process, the seeds to be treated are introduced to a batch treatment tank and the seed treatment mixture is then added and mixed with the seeds. Alternatively a continuous treatment process can be used to apply the seed treatment mixture to seeds in which a stream of seeds are introduced into a receptacle containing the seed treatment slurry and, after contacting the formulation, recovered from the receptacle for drying. A stream of seed treatment mixture can continuously flow into the receptacle as well to replenish quantities of the mixture that are removed with treated seeds.

After application of the seed treatment mixture (whether in a batch process or a continuous process) the seeds are allowed a period of time to dry. For example, the seeds can be spun in a bowl for a period of time, for example, at least 15 seconds, to allow for drying. Different time periods may be needed to allow for variability in drying conditions due to weather or different seed sizes. Moreover, heat can be provided, if desired, to increase drying times, for example, in the form of a heated stream of air. After drying, the coated seeds can undergo a size separation or classification process.

In one embodiment, the seeds treated as described herein include seeds of sugar beet, amaranth, spinach, quinoa, Swiss chard, fodder beet, garden orache, shiny orache, spear orache, halberdleaved orache, spear saltbush, saltbush, sea beet, beet root, mangelwurzel, Good King Henry, strawberry blite, strawberry spinach, maple-leaved goosefoot, nettle-leaved goosefoot, white goosefoot, feathered goosefoot, fig-leaved goosefoot, goosefoot, stinking goosefoot, epazote, manyseeded goosefoot, strawberry goosefoot, grey goosefoot, red goosefoot, greater knapweed, common glasswort, annual sea-blite, and redroot pigweed.

Although the seed treatment methods described herein 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 significant damage during the treatment process. Typically, the seed is a seed that has been harvested from a field; removed from the plant; and/or separated from the fruit and any cob, pod, stalk, outer husk, and surrounding pulp or other non-seed plant material. The seed is preferably also biologically stable to the extent that the treatment would cause no biological damage to the seed. In one embodiment, for example, the treatment can be applied to seed that has been harvested, cleaned and dried to a moisture content below about 15% by weight. In an alternative embodiment, the seed can be one that has been dried and then primed with water and/or another material and then re-dried before or during the treatment with a seed treatment mixture as described herein. In one embodiment, the seed to be treated is thus substantially dry. "Substantially dry" is used herein to refer to a seed that has a moisture content which results if the seed is allowed to equilibrate in an air atmosphere at 20 to 30° C and 30-90% relative humidity, e.g. at 25°C and 50% relative humidity.

The seed treatment composition can be applied to the seed at any time from the harvest of the seed to the sowing of the seed in the ground for the purpose of germination and growth of the plant. For example, the treatment may be carried out several weeks or months, for example up to 12 months, before planting the seed, for example in the form of a seed dressing treatment, without a substantially reduced efficacy being observed. Seeds can be treated, for example, at a central location and then dispersed for planting. This permits the person who plants the seeds to avoid the handling and use of active ingredients and to merely handle and plant the treated seeds in a manner that is conventional for regular untreated seeds, which reduces human exposure.

The compound and composition of the present invention may be useful for the control of pests, such as insects, in improving the tolerance of crop plants to abiotic stress conditions, and/or in improving the yield of crop plants. In one embodiment, the compound and composition of the present invention may be useful for the control of insect and/or acarina and/or nematode pests and/or fungal infections. The present invention provides a method for controlling pests in or on crop plants, improving the tolerance of crop plants to abiotic stress conditions, and/or improving the yield of crop plants, comprising treating seeds of the plants with a composition as described herein.

The method, compound and compositions of the present invention may be useful for extending the duration of protection afforded to the plant material. In one embodiment, the compound and compositions of the present invention may show both a fast-acting curative action and a preventative or protective action.

The method, compound and compositions of the present invention may be useful for extending the range of crops with which the compound and compositions are useful and/or the range of aphid pests against which the compound and compositions provide effective control.

Compounds of formula (I) are described in W02006089633A2.

The compound and compositions according to the invention can be used for controlling or limiting pests of the abovementioned type which occur in particular on Amaranthaceae plants, especially on useful Amaranthaceae plants in agriculture, in horticulture and in forests, or on organs, such as fruits, flowers, foliage, stalks, tubers or roots, of such plants, and in some cases even plant organs which are formed at a later point in time remain protected against these pests.

The compound and compositions of the invention are particularly suitable for control of aphid infestation of Amaranthaceae plants selected from the Betoideae and Chenopodioideae subfamilies.

Suitable target Amaranthaceae crops are, in particular, amaranth (Amaranthus various species), garden orache (Atriplex hortensis), shiny orache (Atriplex nitens), spear orache (Atriplex patula), halberd-leaved orache (Atriplex portulacoides), spear saltbush (Atriplex prostrata), saltbush (Atriplex spp.), sea beet (Beta vulgaris subsp. maritima), beet root (Beta vulgaris subsp. vulgaris var. conditiva), mangelwurzel (Beta vulgaris subsp. vulgaris var. crassa), sugar beet (Beta vulgaris subsp. vulgaris var. altissima), Swiss chard (Beta vulgaris subsp. vulgaris var. cicla/flavescens), fodder beet (Beta vulgaris subsp. vulgaris var. crassa), Good King Henry (Chenopodium bonus-henricus), strawberry blite (Chenopodium capitatum), strawberry spinach (Chenopodium foliosum), mapleleaved goosefoot (Chenopodium hybridum), nettle-leaved goosefoot (Chenopodium murale), white goosefoot (Chenopodium album), feathered goosefoot (Chenopodium botrys), fig-leaved goosefoot (Chenopodium ficifolium), quinoa (Chenopodium quinoa), goosefoot (Chenopodium spp.), stinking goosefoot (Chenopodium vulvaria), epazote (Chenopodium ambrosioides), many-seeded goosefoot (Chenopodium polyspermum), strawberry goosefoot (Chenopodium chenopodioides), grey goosefoot (Chenopodium glaucum), red goosefoot (Chenopodium rubrum), greater knapweed (Polycnemum majus), common glasswort (Salicornia europaea), redroot pigweed (Amaranthus retroflexus), spinach (Spinacia oleracea), and annual sea-blite (Suaeda maritima).

The compound and compositions of the invention are particularly suitable for controlling, limiting or preventing infestation of an Amaranthaceae plant by an aphid selected from the groups consisting of green peach aphid (Myzus persicae), bean aphid (Aphis fabae), cotton aphid (Aphis gossypii), sugar beet root aphid (Pemphigus betae) and cabbage aphid (Brevicoryne brassicae).

The term "crops" as used herein is to be understood as including also crop plants which have been so transformed by the use of recombinant DNA techniques that they are capable of synthesising antipathogenic substances having a selective action, such as, for example, the so-called "pathogenesis-related proteins" (PRPs, see e.g. EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesising such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95/33818 and EP-A-0 353 191. The methods of producing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

Crops may also be modified for enhanced resistance to fungal (for example Fusarium, Anthracnose, or Phytophthora), bacterial (for example Pseudomonas) or viral (for example potato leafroll virus, tomato spotted wilt virus, cucumber mosaic virus) pathogens.

Crops also include those that have enhanced resistance to nematodes, such as the soybean cyst nematode.

Crops that are tolerance to abiotic stress include those that have enhanced tolerance to drought, high salt, high temperature, chill, frost, or light radiation, for example through expression of NF-YB or other proteins known in the art.

Antipathogenic substances which can be expressed by such transgenic plants include, for example, ion channel blockers, such as blockers for sodium and calcium channels, for example the viral KP1 , KP4 or KP6 toxins; stilbene synthases; bibenzyl synthases; chitinases; glucanases; the so-called "pathogenesis-related proteins" (PRPs; see e.g. EP-A-0 392 225); antipathogenic substances produced by microorganisms, for example peptide antibiotics or heterocyclic antibiotics (see e.g. WO 95/33818) or protein or polypeptide factors involved in plant pathogen defence (so-called "plant disease resistance genes", as described in WO 03/000906).

The present invention provides a method of improving the tolerance of an Amaranthaceae plant to

The present invention provides a method for regulating or improving the growth of an Amaranthaceae plant, wherein the method comprises applying to the plant propagation material a compound or composition as described herein. In one embodiment, plant growth is regulated or improved when the plant is subject to abiotic stress conditions.

The term “regulating or improving the growth of a crop” means an improvement in plant vigour, an improvement in plant quality, improved tolerance to stress factors, and/or improved input use efficiency.

Where a range of numbers is disclosed herein (for example, 1 to 10), this is intended to include all numbers and intervening values within that range (for example, 1 , 1 .1 , 2, 3, 3.9, 4, 5, 6, 6.5, 7, 8, 9 and 10) and also any sub-range of numbers and intervening values within that range (for example, 2 to 8, 1 .5 to 5.5 and 3.1 to 4.7). Additionally, it is intended that the both the upper and lower limits specified are included within the range.

Where ranges or values used herein are preceded by the term “about”, this term is intended to provide support for both the exact number that it precedes, and also a number that is near to or approximately the number that it precedes. In determining whether a number is near to or approximately a specifically recited number, the near or approximating number may be a number, which would be rounded to or be substantially equivalent to the specifically recited number. For example, the term “about 5” includes 5.0, 4.5, 5.4, 4.92, 5.01 , and so on.

The composition can be in the form of concentrates which are diluted prior to use, although ready-to- use compositions can also be made. The final dilution is usually made with water, but can be made instead of, or in addition to, water, with, for example, liquid fertilisers, micronutrients, biological organisms, oil or solvents.

The composition according to the invention can be generally formulated in various ways using formulation adjuvants, such as carriers, solvents and surface-active substances. The formulations can be in various physical forms, e.g. in the form of dusting powders, gels, wettable powders, water- dispersible granules, water-dispersible tablets, effervescent pellets, emulsifiable concentrates, micro- emulsifiable concentrates, oil-in-water emulsions, oil-flowables, aqueous dispersions, oily dispersions, suspo-emulsions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as carrier), impregnated polymer films or in other forms known e.g. from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can either be used directly or diluted prior to use. The dilutions can be made, for example, with water, liquid fertilisers, micronutrients, biological organisms, oil or solvents.

The formulations can be prepared e.g. by mixing the active ingredient with the formulation adjuvants in order to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other adjuvants, such as finely divided solids, mineral oils, oils of vegetable or animal origin, modified oils of vegetable or animal origin, organic solvents, water, surface-active substances or combinations thereof.

The active ingredients can also be contained in very fine microcapsules. Microcapsules contain the active ingredients in a porous carrier. This enables the active ingredients to be released into the environment in controlled amounts (e.g. slow-release). Microcapsules usually have a diameter of from 0.1 to 500 microns. They contain active ingredients in an amount of about from 25 to 95 % by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can comprise, for example, natural or synthetic rubbers, cellulose, styrene/butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers that are known to the person skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely divided particles in a solid matrix of base substance, but the microcapsules are not themselves encapsulated.

The formulation adjuvants that are suitable for the preparation of the compositions according to the invention are known per se. As liquid carriers there may be used: water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1 ,2-dichloropropane, diethanolamine, p- diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1 ,4- dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1 ,1 ,1-trichloroethane, 2- heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols of higher molecular weight, such as amyl alcohol, tetrahydro-furfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone and the like.

Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.

A large number of surface-active substances can advantageously be used in both solid and liquid formulations, especially in those formulations which can be diluted with a carrier prior to use. Surfaceactive substances may be anionic, cationic, non-ionic or polymeric and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surface-active substances include, for example, salts of alkyl sulfates, such as diethanolammonium lauryl sulfate salts of alkylarylsulfonates, such as calcium dodecylbenzenesulfonate alkylphenol/alkylene oxide addition products, such as nonylphenol ethoxylate alcohol/alkylene oxide addition products, such as tridecylalcohol ethoxylate soaps, such as sodium stearate salts of alkylnaphthalenesulfonates, such as sodium dibutylnaphthalenesulfonate dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl)sulfosuccinate sorbitol esters, such as sorbitol oleate quaternary amines, such as lauryltrimethylammonium chloride, polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate block copolymers of ethylene oxide and propylene oxide and salts of mono and di-alkylphosphate esters and also further substances described e.g. in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981).

Further adjuvants that can be used in pesticidal formulations include crystallisation inhibitors, viscosity modifiers, suspending agents, dyes, anti-oxidants, foaming agents, light absorbers, mixing auxiliaries, antifoams, complexing agents, neutralising or pH-modifying substances and buffers, corrosion inhibitors, fragrances, wetting agents, take-up enhancers, micro-nutrients, plasticisers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilisers.

The compositions according to the invention can include an additive comprising an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the invention is generally from 0.01 to 10 %, based on the mixture to be applied. For example, the oil additive can be added to a spray tank in the desired concentration after a spray mixture has been prepared. Preferred oil additives comprise mineral oils or an oil of vegetable origin, for example rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example the methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of C8 C22 fatty acids, especially the methyl derivatives of C12-C18 fatty acids, for example the methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10th Edition, Southern Illinois University, 2010.

Preferred formulations can have the following compositions (weight %)

Emulsifiable concentrates: active ingredient: 1 to 95 %, preferably 60 to 90 % surface-active agent: 1 to 30 %, preferably 5 to 20 % liquid carrier: 1 to 80 %, preferably 1 to 35 %

Dusts: active ingredient: 0.1 to 10 %, preferably 0.1 to 5 % solid carrier: 99.9 to 90 %, preferably 99.9 to 99 %

Suspension concentrates: active ingredient: 5 to 75 %, preferably 10 to 50 % water: 94 to 24 %, preferably 88 to 30 % surface-active agent: 1 to 40 %, preferably 2 to 30 % Wettable powders: active ingredient: 0.5 to 90 %, preferably 1 to 80 % surface-active agent: 0.5 to 20 %, preferably 1 to 15 % solid carrier: 5 to 95 %, preferably 15 to 90 % Granules: active ingredient: 0.1 to 30 %, preferably 0.1 to 15 % solid carrier: 99.5 to 70 %, preferably 97 to 85 %

The following Examples further illustrate, but do not limit, the invention.

The combination 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.

The combination 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.

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 combination with the carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

The combination 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.

The finely ground combination is uniformly applied, in a mixer, to the kaolin moistened with polyethylene glycol. Non-dusty coated granules are obtained in this manner.

Suspension concentrate

The finely ground combination 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

Slow Release Capsule Suspension

28 parts of the combination are mixed with 2 parts of an aromatic solvent and 7 parts of toluene diisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). This mixture is emulsified in a mixture of 1 .2 parts of polyvinylalcohol, 0.05 parts of a defoamer and 51 .6 parts ofwater until the desired particle size is achieved. To this emulsion a mixture of 2.8 parts 1 ,6-diaminohexane in 5.3 parts of water is added. The mixture is agitated until the polymerization reaction is completed. The obtained capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The capsule suspension formulation contains 28% of the active ingredients. The medium capsule diameter is 8-15 microns. The resulting formulation is applied to seeds as an aqueous suspension in an apparatus suitable for that purpose.

The compound or composition of the present invention may be applied pre-emergence. Where the compound or composition is used to inhibit or delay the germination of seeds, it may be applied preemergence. Where the compound or composition is used to control pests, it may be applied as a preventative (before pest establishment) or curative (after pest establishment) treatment.

The present invention envisages application of the compound and composition of the invention to plant propagation material prior to, during, or after planting, or any combination of these.

Although active ingredients can be applied to plant propagation material in any physiological state, a common approach is to use seeds in a sufficiently durable state to incur no damage during the treatment process. Typically, seed would have 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. Seed would preferably also be biologically stable to the extent that treatment would not cause biological damage to the seed. It is believed that treatment can be applied to seed at any time between seed harvest and sowing of seed including during the sowing process.

Methods for applying or treating active ingredients on to plant propagation material or to the locus of planting are known in the art and include dressing, coating, pelleting and soaking as well as nursery tray application, in furrow application, soil drenching, soil injection, drip irrigation, application through sprinklers or central pivot, or incorporation into soil (broad cast or in band). Alternatively or in addition active ingredients may be applied on a suitable substrate sown together with the plant propagation material.

The rates of application of compound and composition of the present invention may vary within wide limits and depend on the nature of the soil, the method of application (pre- or post-emergence, seed dressing, application to the seed furrow, no tillage application etc.), the crop plant, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop.

The method, compound and compositions according to the invention can be used in combination with other pesticides, including other pesticides such as insecticides, acaricides, nematicides, fungicides, or agents that enhance the activity of the composition according to the invention, in for example chemical treatment or pest control programs. The combination may have further surprising advantages, which could be described as synergistic effects.

Suitable other pesticides are, for example, pesticides of the following classes of active ingredients: organophosphates, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, benzophenone derivatives, ureas, pyrrole derivatives, carbamates, pyrethroids, chlorinated hydrocarbons, acylureas, pyridylmethyleneamino derivatives, macrolides, benzoylureas, neonicotinoids and biological agents such as Bacillus thurigiensis strains or bacterially-derived pesticides such as spinosads, avermectins and Cry proteins.

Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).

Crops are also to be understood as being those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include d- endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.

An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut (Syngenta Seeds). An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification). For example, a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

Table 1 sets out exemplary application rates (in grams per hectare, g/ha) and lists key aphid pests against which the compound and compositions are particularly effective and key seed species for which these are particularly advantageous as seed treatments. Each combination of the compound of formula (I) and each seed and pest is individually exemplified by Table 1 .

TABLE 1

TABLE 1A

TABLE 1B

TABLE 1C

TABLE 1D

TABLE 1E

TABLE 1 F

Table 2 sets out exemplary application rates (as grams per kg of seed, g/kg seed) and lists key aphid pests against which the compound and compositions are particularly effective and key seed species for which these are particularly advantageous as seed treatments. Each combination of the compound of formula (I) and each seed and pest is individually exemplified by Table 2.

TABLE 2A

TABLE 2B

TABLE 2C

TABLE 2D

TABLE 2E

TABLE 2F

Table 3 sets out exemplary application rates (as milligrams per seed, mg/seed) and lists key aphid pests against which the compound and compositions are particularly effective and key seed species for which these are particularly advantageous as seed treatments. Each combination of the compound of formula (I) and each seed and pest is individually exemplified by Table 3.

TABLE 3A

TABLE 3B

TABLE 3C

TABLE 3D

TABLE 3E

TABLE 3F

Biological Examples

A treated sugar beet seed is sown in a 350 ml pot filled with soil. Two weeks after sowing, the sugar beet seedling is infested with an aphid population of mixed stages. After an incubation period of seven days the grade of efficacy as well as phytotoxicity (lack of shoot - missing emergence) compared to the control is estimated and expressed in percentage.

TABLE 4

counted number of aphids

Claims

1 . A method of controlling, limiting or preventing infestation of a sugar beet plant by an aphid, which comprises applying to a propagation material of the plant, an insecticidally effective amount of a compound of formula (I):

or an agrochemically acceptable salt thereof.

2. The method of claim 1 , wherein the sugar beet plant is Beta vulgaris subsp. vulgaris var. altissima.

3. The method according to any one of claims 1-2, wherein the aphid is selected from pea aphid (Acyrthosiphon pisum), cowpea apbrehid (Aphis craccivora), bean aphid (Aphis fabae), cotton aphid (Aphis gossypii), foxglove aphid (Aulacorthum solani), large rose aphid (Brachycaudus helichrysi), cabbage aphid (Brevicoryne brassicae), celery aphid (Cavariella aegopodii), coriander aphid (Hyadaphis coriandri), lettuce aphid (Hyperomyzus lactucae), turnip aphid (Lipaphis erysimi), potato aphid (Macrosiphum euphorbiae), shallot aphid (Myzus ascalonicus), cherry blackfly (Myzus cerasi), green peach aphid (Myzus persicae), sugar beet root aphid (Pemphigus betae), corn leaf aphid (Rhopalosiphum maidis), bird cherry-oat aphid (Rhopalosiphum padi), cereal aphid (Sitobion avenae), black bean aphid (Therioaphis trifolii), and goldenrod aphid (Uroleucon hypochoeridis).

4. The method according to any one of claims 1-3, wherein the aphid is selected from sugar beet root aphid (Pemphigus betae), green peach aphid (Myzus persicae), cowpea aphid (Aphis craccivora), bean aphid (Aphis fabae), foxglove aphid (Aulacorthum solani), potato aphid (Macrosiphum euphorbiae) and bean aphid (Aphis fabae).

5. The method according to any one of claims 1-4, wherein the plant propagation material is a seed.

6. The method according to any one of claims 1-5, wherein the compound of formula (I) is applied in a rate of from 0.1 to 2000 g/ha, preferably 1 to 2000 g/ha, 2 to 1500 g/ha, 5 to 1000 g/ha, 10 to 500 g/ha, 20 to 200 g/ha, 30 to 150 g/ha or 50 to 100 g/ha.

7. The method according to any one of claims 1-5, wherein the compound of formula (I) is applied in a rate of from 0.03 to 600 g per kg of plant propagation material, preferably 0.3 to 500 g, 1 to 400 g, 2 to 300 g, 4 to 150 g, 8 to 100 g, 12 to 60 g or 15 to 30 g per kg of plant propagation material, especially seed.

8. The method according to any one of claims 1-5, wherein the compound of formula (I) is applied in a rate of from 0.001 to 50 mg per plant propagation material, preferably 0.01 to 20 mg, 0.02 to 15 mg, 0.05 to 10 mg, 0.1 to 5 mg, 0.2 to 2 mg, 0.3 to 1 .5 mg or 0.5 to 1 mg per plant propagation material, especially seed.

9. A seed treatment composition comprising a compound of formula (I):

or an agrochemically acceptable salt thereof, and one or more auxiliaries and/or diluents, wherein the seed treatment composition comprises 0.03 to 600 g of the compound of formula (I) per kg of seed to be treated.

10. The seed treatment composition according to claim 9, wherein the seed treatment composition comprises 0.3 to 500 g of the compound of formula (I) per kg of seed to be treated, preferably from 1 to 400 g, 2 to 300 g, 4 to 150 g, 8 to 100 g, 12 to 60 g or 15 to 30 g per kg of seed to be treated.