Method for controlling or preventing damage to plants caused by plant-parasitic nematodes of the genus Aphelenchoides, particularly by the rice root nematode

Abstract

The present invention relates to a method for controlling or preventing damage to plants by plant-parasitic nematodes of the genus Aphelenchoides, which method comprises the step of applying to a crop of plants, the locus thereof, or the propagation material thereof the compound cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram.

Description

[Technical Field]

[0001] The present invention relates to a method for controlling or preventing plant damage caused by plant-parasitic nematodes of the genus Aphelenchoides, in particular the rice root nematode Aphelenchoides besseyi. [Background technology]

[0002] Aphelenchoides spp. is a genus of nematodes that globally infects annual crops such as rice, strawberry, bean, cowpea, soybean, cotton, and ornamental species (e.g., chrysanthemum, rose, gladiolus, violet, and begonia). The nematodes attack young tissues in the above-ground parts of plants (stems, leaves, buds, flowers, and pods), primarily causing significant reductions in crop yield when the attack is concentrated in the reproductive parts of the plant (flowers, inflorescences, and pods). During part of their life cycle, the nematodes inhabit the roots of plants (like most plant-parasitic nematodes), and during part of their life cycle, the nematodes inhabit the above-ground parts, where plant damage is more pronounced. Therefore, there is a strong need to provide effective methods for controlling or preventing damage caused by Aphelenchoides spp. nematodes, particularly the rice root nematode Aphelenchoides besseyi. Summary of the Invention [Means for solving the problem]

[0003] The present invention provides an improved method for controlling or preventing plant damage caused by plant-parasitic nematodes of the genus Aphelenchoides, in particular the rice root nematode Aphelenchoides besseyi. DETAILED DESCRIPTION OF THE INVENTION

[0004] Cyclobutylcarboxamide compounds and methods for their preparation are disclosed in WO 2013 / 143811 and WO 2015 / 003951. One cyclobutylcarboxamide, cyclobutrifluram (ISO name, CAS RN [1460292-16-3]), was recently announced to be under development as a nematicide (http: / / pmonline.azurewebsites.net / _Main / Pesticide.aspx). The chemical structure of cyclobutrifluram is: [ka] is.

[0005] It has been known that cyclobutrifluram has activity against root-knot nematodes, such as Meloidogyne, and cyst nematodes, such as Heterodera. These nematode species live in the soil and attack the root systems of many plants. However, Aphelenchoides nematodes attack the above-ground parts of plants, such as stems, leaves, buds, flowers, and pods. This means that Aphelenchoides nematodes can feed both ectoparasitic (on the surface of plants) and endoparasitic (within plant tissues). Therefore, these nematodes can move around both outside and inside plants. This makes the task of controlling or preventing damage caused by Aphelenchoides nematodes extremely difficult. A potential nematicide needs to not only be active against the target nematode species, but also be able to reach all parts of the plant to effectively control or prevent damage. Most current nematicides are not systemic, i.e., they are unable to reach all of the plant parts that Aphelenchoides nematodes feed on, leading to suboptimal control of this type of nematode.

[0006] It has now been unexpectedly discovered that cyclobutrifluram is highly effective in controlling or preventing plant damage caused by Aphelenchoides spp. plant-parasitic nematodes. Thus, this highly effective compound offers farmers an important new solution for controlling or preventing plant damage caused by Aphelenchoides spp. plant-parasitic nematodes. Cyclobutrifluram has been found to be highly effective when used as a seed treatment against attack by the rice root nematode Aphelenchoides besseyi. Aphelenchoides besseyi attacks the above-ground parts of plants, meaning that cyclobutrifluram can protect not only the seeds to which it is applied, but also the plants growing from the treated seeds. Tests have shown that cyclobutrifluram protects plants growing from the treated seeds far more effectively than any currently used commercial standard. Cyclobutrifluram therefore offers the farmer an excellent means for controlling or preventing damage caused by nematodes of the genus Aphelenchoides, in particular the rice root nematode Aphelenchoides besseyi.

[0007] Thus, in embodiment 1, there is provided a method for controlling or preventing plant damage caused by plant parasitic nematodes of the genus Aphelenchoides, the method comprising the step of applying the compound cyclobutrifluram to a crop of plants, a locus thereof, or propagation material thereof.

[0008] The cyclobutrifluram disclosed above represents a cis racemate: the phenyl ring on the left and the pyridyl-C(=O)-NH group on the right correspond to formulae (Ia) and (Ib): [ka] As shown for the compound of formula (I), the rings are cis to each other on the cyclobutyl ring.

[0009] Thus, a racemic compound of cyclobutrifluram is a 1:1 mixture of compounds of formula (Ia) and (Ib). The wedge-shaped bonds shown in compounds of formula (Ia) and (Ib) represent absolute stereochemistry, while bold, straight bonds such as those shown for cyclobutrifluram represent relative stereochemistry in the racemic compound.

[0010] It has also been surprisingly found that one enantiomer of cyclobutrifluram is particularly useful in controlling or preventing plant damage caused by plant parasitic nematodes of the genus Aphelenchoides.

[0011] Thus, in embodiment 2, cyclobutrifluram is the (1S,2S) stereoisomer [ka] The method of any one of embodiments 1 is provided in the form

[0012] Those skilled in the art will recognize that, according to the methods described in Embodiment 1 or 2, cyclobutrifluram is generally applied as part of a pesticidal composition. Accordingly, as Embodiment 3, there is provided a method for controlling or preventing plant damage caused by plant-parasitic nematodes of the genus Aphelenchoides, comprising applying to a plant crop, its locus, or its propagation material a pesticidal composition comprising cyclobutrifluram and one or more pharmaceutical auxiliaries. As Embodiment 4, there is provided a method for controlling or preventing plant damage caused by plant-parasitic nematodes of the genus Aphelenchoides, comprising applying to a plant crop, its locus, or its propagation material a pesticidal composition comprising a compound of formula (Ia) and one or more pharmaceutical auxiliaries. In the method according to embodiment 5, in pesticidal compositions comprising both the (1S,2S) and (1R,2R) stereoisomers of cyclobutrifluram, the ratio of the (1S,2S) stereoisomer to its enantiomer (1R,2R) is greater than 1: 1. Preferably, the ratio of (1S,2S) to (1S,2S) is greater than 1.5:1, more preferably greater than 2.5:1, in particular greater than 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.

[0013] It is also understood that mixtures containing not more than 50%, preferably not more than 40%, more preferably not more than 30%, in particular not more than 20%, advantageously not more than 10%, desirably not more than 5%, in particular not more than 3% of the trans stereoisomer of the compound of formula (I) (i.e., in which the phenyl and pyridyl-C(=O)-NH groups are trans relative to each other) are part of the present invention. Preferably, the ratio of cis to trans isomer is greater than 1.5:1, more preferably greater than 2.5:1, in particular greater than 4:1, advantageously greater than 9:1, desirably greater than 20:1, in particular greater than 35:1.

[0014] As embodiment 6, there is provided the method of any one of embodiments 1 to 5, wherein the pesticidal composition is a suspension concentrate composition.

[0015] As a seventh embodiment, - providing cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram according to any one of embodiments 1 to 6; - applying the composition to the propagation material; - planting the propagation material; The method of any one of embodiments 1 to 6 is provided, comprising:

[0016] As an eighth embodiment, - providing cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram according to any one of embodiments 1 to 6; applying the composition to the plant crop or to the locus thereof; The method of any one of embodiments 1 to 6 is provided, comprising:

[0017] In embodiment 9, there is provided use of cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram according to any one of embodiments 1 to 6 for controlling or preventing damage to plants caused by plant-parasitic nematodes of the genus Aphelenchoides.

[0018] In embodiment 10, there is provided a method or use according to any one of embodiments 1 to 9, wherein the plant-parasitic nematode is Aphelenchoides besseyi.

[0019] In embodiment 11, there is provided a method or use according to any one of embodiments 1 to 10, wherein the plant is selected from rice, strawberry, bean, cowpea, soybean, cotton and ornamental species (e.g., chrysanthemum, rose, gladiolus, violet, begonia).

[0020] In embodiment 12, there is provided a method or use according to any one of embodiments 1 to 10, wherein the plant is selected from rice, soybean, and cotton.

[0021] In embodiment 13, there is provided a method or use according to any one of embodiments 1 to 10, wherein the plant is selected from soybean and cotton.

[0022] In embodiment 14, there is provided a method or use according to any one of embodiments 1 to 10, wherein the plant is selected from soybean.

[0023] In embodiment 15, there is provided a method for growing soybeans, the method comprising applying or treating the propagation material with cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram as defined in any one of claims 1 to 6.

[0024] In embodiment 16, there is provided a method for growing cotton, the method comprising applying or treating the propagation material with cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram as defined in any one of claims 1 to 6.

[0025] In embodiment 17, there is provided a method for growing pulses, the method comprising applying or treating the propagation material with cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram as defined in any one of claims 1 to 6.

[0026] In embodiment 18, there is provided a method for growing strawberry plants, the method comprising applying or treating the propagation material thereof with cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram as defined in any one of claims 1 to 6.

[0027] In embodiment 19, there is provided a method for growing ornamental species, the method comprising applying or treating the propagation material with cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram as defined in any one of claims 1 to 6.

[0028] In embodiment 20, there is provided a method for growing rice, the method comprising applying or treating the propagation material with cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram as defined in any one of claims 1 to 6.

[0029] In embodiment 21, there is provided a method or use according to any one of claims 1 to 20, wherein the propagation material is a seed.

[0030] As embodiment 22, there is provided a method or use according to any one of claims 1 to 21, wherein the compound cyclobutrifluram is applied to the seeds in an amount of 5 grams to 100 grams of cyclobutrifluram per 100 kg of seeds.

[0031] As embodiment 23, there is provided a method or use according to any one of claims 1 to 21, wherein the compound cyclobutrifluram is applied to the seeds in an amount of 10 grams to 80 grams of cyclobutrifluram per 100 kg of seeds.

[0032] As embodiment 24, there is provided a method or use according to any one of claims 1 to 21, wherein the compound cyclobutrifluram is applied to the seeds in an amount of 10 grams to 40 grams of cyclobutrifluram per 100 kg of seeds.

[0033] The preparation of cyclobutrifluram is disclosed in WO 2013 / 143811 and WO 2015 / 003951, which are incorporated herein by reference.

[0034] The term "seed" includes seeds and all types of plant propagation material, including, but not limited to, true seeds, seed pieces, suckers, corms, bulbs, fruits, tubers, grains, rhizomes, cuttings, cuttings, etc., and in preferred embodiments refers to true seeds.

[0035] The application according to any one of the methods or uses of embodiments 1 to 24 is preferably to a plant crop, a locus thereof, or a propagation material thereof. Preferably, the application is to a plant crop or a propagation material thereof, more preferably to a propagation material. The application of cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram can be carried out according to any of the usual application forms, such as foliar application, drench, soil application, furrow application, etc.

[0036] The compounds according to any one of embodiments 1 to 24 are preferably used for pest control at 1 to 500 g / ha, preferably 10 to 70 g / ha.

[0037] The method according to any one of embodiments 1 to 24 is suitable for use on any plant, including those genetically modified to be tolerant to an active ingredient such as a herbicide, or for producing biologically active compounds that control damage caused by plant pests.

[0038] Generally, cyclobutrifluram is used in the form of a composition (eg, a formulation) containing a carrier. The cyclobutrifluram and compositions comprising cyclobutrifluram according to any one of embodiments 1 to 5 can be used in the form of an aerosol dispenser, a capsule suspension, a cold fogging concentrate, a dust, an emulsifiable concentrate, an oil-in-water emulsion, a water-in-oil emulsion, an encapsulated granule, a fine granule, a seed treatment flowable, a (pressurized) gas, a gas generating product, a granule, a hot fogging concentrate, a macrogranule, a microgranule, an oil-dispersible powder, an oil-miscible flowable, an oil-miscible liquid, a paste, a plant rodlet, a dry seed treatment powder, a pesticide-coated seed, a soluble concentrate, a soluble dust, a seed treatment liquid, a suspension concentrate (flowable), an ultra low volume (ulv) liquid, an ultra low volume suspension It can be used in various forms such as a water dispersible volume (ulv) suspension, a water dispersible granule or tablet, a water dispersible powder for slurry treatment, a water soluble granule or tablet, a water soluble dust for seed treatment and a water dispersible powder.

[0039] The formulation typically comprises a liquid or solid carrier and optionally one or more conventional formulation auxiliaries, which may be solid or liquid auxiliaries, such as non-epoxidized or epoxidized vegetable oil (for example, epoxidized coconut oil, rapeseed oil or soybean oil), antifoaming agent, for example, silicone oil, preservative, clay, inorganic compound, viscosity regulator, surfactant, binder and / or tackifier.The composition not only comprises the compound of the present invention and one or more other biologically active substances such as bactericides, fungicides, nematicides, plant activators, acaricides and insecticides, but also may further comprise fertilizers, micronutrient donors or other preparations that affect plant growth.

[0040] The compositions are prepared in a manner known per se in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid compound of the invention, and in the presence of at least one auxiliary, for example by intimately mixing and / or grinding the compound with one or more auxiliaries, In the case of the solid compound of the invention, grinding / milling of the compound is carried out to ensure a specific particle size.

[0041] Examples of compositions for agricultural use are emulsifiable concentrates, suspension concentrates, microemulsions, oil-dispersible, directly sprayable or dilutable solutions, spreadable pastes, dilute emulsifiable concentrates, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymeric materials, which contain—at least—cyclobutrifluram, the type of composition being chosen to suit the intended purpose and the circumstances at hand.

[0042] Typically, the composition comprises 0.1 to 99%, in particular 0.1 to 95%, of cyclobutrifluram and 1 to 99.9%, in particular 5 to 99.9%, of at least one solid or liquid carrier, and typically 0 to 25%, in particular 0.1 to 20%, of the composition can be surfactant (% in each case means percent by weight). Concentrated compositions tend to be preferred commercially, but end users typically use diluted compositions with significantly lower concentrations of active ingredient.

[0043] Examples of foliar formulation types for premix compositions are as follows: GR: Granules WP: Wettable powder WG: Hydrable granule (powder) SG: Water-soluble granules SL: Soluble thickener EC: Emulsifiable concentrate EW: oil in water emulsion ME: Microemulsion SC: Aqueous suspension concentrate CS: Aqueous capsule suspension OD: oil-based suspension concentrate, and SE: aqueous suspo-emulsion.

[0044] On the other hand, examples of seed treatment formulation types for premix compositions are as follows: WS: Wettable powder for seed treatment slurry LS: Liquid for seed treatment ES: Emulsion for seed treatment FS: Suspension concentrate for seed treatment WG: water dispersible granules, and CS: Aqueous capsule suspension.

[0045] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions, or mixtures thereof, and dusts.

[0046] The nature of the formulation as well as the method of application, whether foliar application, dredging, spraying, atomizing, dusting, spreading, painting or pouring, will be selected according to the intended purpose and the circumstances at hand.

[0047] Tank-mix compositions are generally prepared by diluting with a solvent (eg, water) one or more pre-mix compositions containing different pesticides and, optionally, additional adjuvants.

[0048] Suitable carriers and adjuvants may be solid or liquid and are substances commonly used in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0049] Generally, tank-mix formulations for foliar or soil application contain 0.1 to 20%, particularly 0.1 to 15%, of the desired ingredient and 99.9 to 80%, particularly 99.9 to 85%, of a solid or liquid auxiliary (including, for example, a solvent such as water), which auxiliary may be a surfactant in an amount of 0 to 20%, particularly 0.1 to 15%, based on the tank-mix formulation.

[0050] Typically, premix formulations for foliar application comprise 0.1 to 99.9%, in particular 1 to 95%, of the desired ingredient and 99.9 to 0.1%, in particular 99 to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), which may be a surfactant in an amount of 0 to 50%, in particular 0.5 to 40%, based on the premix formulation.

[0051] Typically, tank-mix formulations for seed treatment application comprise 0.25 to 80%, in particular 1 to 75%, of the desired ingredients and 99.75 to 20%, in particular 99 to 25%, of a solid or liquid adjuvant (including, for example, a solvent such as water), which may be a surfactant in an amount of 0 to 40%, in particular 0.5 to 30%, based on the tank-mix formulation.

[0052] Typically, premix formulations for seed treatment application comprise 0.5 to 99.9%, in particular 1 to 95%, of the desired component and 99.5 to 0.1%, in particular 99 to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), which may be a surfactant in an amount of 0 to 50%, in particular 0.5 to 40%, based on the premix formulation.

[0053] Commercially available products will preferably be formulated as concentrates (e.g., premix compositions), while end users will typically employ dilute formulations (e.g., tank-mix compositions).

[0054] A preferred seed treatment premix formulation is an aqueous suspension concentrate. This formulation can be applied to seeds using conventional treatment techniques and machines, such as fluidized bed technology, roller mill method, rotostatic seed treater, and drum coater. Other methods, such as spouted bed, can also be useful. Seeds can be pre-classified before application. After application, the seeds are typically dried and then transferred to a classifier for classification. Such procedures are known in the art. Cyclobutriflurum is particularly suitable for use in soil and seed treatment applications.

[0055] The invention will now be illustrated by the following non-limiting examples, all citations of which are incorporated by reference. [Example]

[0056] Biological Examples Efficacy of nematicide treatments against Aphelenchoides spp. To evaluate the effectiveness of nematicidal treatments against the rice root nematode (Aphelenchoides besseyi), a soybean pot trial was conducted in a greenhouse at Holambra Field Station (São Paulo, Brazil). Seeds of the susceptible soybean variety Nidera 6828 IPRO were treated in the field (seed treatment) using 0.6 liters of slurry (spray solution) per 100 kg of soybean seeds. The treated seeds (treatments 3–10) were then compared with an untreated control (check). Two seeds were sown in one-liter pots containing Holambra Mix (25% Holambra station soil and 75% pasteurized sand). After soybean emergence, plants were sorted by removing poorly growing plants from the pot; each pot ultimately contained one plant per pot for further inoculation. Nematode inoculation of each plant was performed 8 days after emergence (at crop stage V1) with 1,000 Aphelenchoides larvae per plant, directed toward the base of the plant, using a pipette. Each plot in the test was a pot containing one infected soybean plant. A total of six replicates were used per treatment. Plants were grown in separate plastic chambers in a greenhouse with an average daytime temperature of 30°C and nighttime temperature of 20°C (to avoid contamination of the plots). Plants were watered multiple times daily by an automatic sprinkler system (to maintain a favorable environment for nematode population growth and migration to the above-ground parts of the plant). Nematode counts (total number of larvae per gram of above-ground parts (stems + leaves)) were performed 28 days after inoculation (28DAI).

[0057] [Table 1]

[0058] [Table 2]

[0059] [Table 3]

[0060] [Table 4]

[0061] [Table 5]

[0062] [Table 6]

[0063] [Table 7]

[0064] Conclusion: In this trial, cyclobutrifluram showed unexpectedly good activity against Aphelenchoides besseyi attacking soybean 28 days after inoculation evaluation, statistically superior to Avicta 500FS and Ilevo 600FS (even at the lowest tested dose of 5 g AI per 100 kg seed). Another aspect of the present invention may be as follows. [1] A method for controlling or preventing plant infestation by plant-parasitic nematodes of the genus Aphelenchoides, comprising the step of applying the compound cyclobutrifluram to a plant crop, its locus, or its propagation material. [2] The method according to [1], wherein the compound cyclobutrifluram is applied as a pesticidal composition comprising cyclobutrifluram and one or more pharmaceutical auxiliaries. [3] The method according to [2], wherein the pesticidal composition is a suspension composition. [4] The method according to any one of [1] to [3] above, wherein the plant parasitic nematode is Aphelenchoides besseyi. [5] The method according to any one of [1] to [4] above, wherein the plant is selected from rice, strawberry, beans, cowpea, soybean, cotton, and ornamental species. [6] The method according to any one of [1] to [4] above, wherein the plant is soybean or cotton. [7] The method according to any one of [1] to [4] above, wherein the plant is soybean. [8] The method according to any one of [1] to [7], wherein the compound cyclobutrifluram or a pesticidal composition containing cyclobutrifluram is applied to propagation material. [9] The method according to [8], wherein the propagation material is a seed.

[10] The method according to [9], wherein the compound cyclobutrifluram is applied to the seeds in an amount of 5 grams to 100 grams of cyclobutrifluram per 100 kg of seeds.

[11] The method according to [9], wherein the compound cyclobutrifluram is applied to the seeds in an amount of 10 grams to 80 grams of cyclobutrifluram per 100 kg of seeds.

[12] The method according to [9], wherein the compound cyclobutrifluram is applied to the seeds in an amount of 10 grams to 40 grams of cyclobutrifluram per 100 kg of seeds.

[13] Use of cyclobutrifluram or a pesticidal composition containing cyclobutrifluram to control or prevent infestation of plants by plant-parasitic nematodes of the genus Aphelenchoides.

[14] The use according to

[13] above, wherein the plant parasitic nematode is Aphelenchoides besseyi.

[15] The use according to embodiment 13 or 14, wherein the plant is selected from rice, strawberry, beans, cowpea, soybean, cotton and ornamental species.

Claims

1. 1. A method for controlling or preventing infestation of plants by plant parasitic nematodes of the genus Aphelenchoides, comprising the step of applying the compound cyclobutrifluram to a crop of plants, the locus thereof, or the propagation material thereof.

2. 10. The method of claim 1, wherein the compound cyclobutrifluram is applied as a pesticidal composition comprising cyclobutrifluram and one or more pharmaceutical auxiliaries.

3. The method of claim 2 wherein the pesticidal composition is a suspension composition.

4. The method according to any one of claims 1 to 3, wherein the plant-parasitic nematode is Aphelenchoides besseyi.

5. The method according to any one of claims 1 to 4, wherein the plant is selected from rice, strawberry, pulses, cowpea, soybean, cotton and ornamental species.

6. The method according to any one of claims 1 to 4, wherein the plant is soybean or cotton.

7. The method according to any one of claims 1 to 4, wherein the plant is soybean.

8. The method according to any one of claims 1 to 7, wherein the compound cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram is applied to propagation material.

9. The method of claim 8, wherein the propagation material is a seed.

10. 10. The method of claim 9, wherein the compound cyclobutrifluram is applied to the seeds in an amount of 5 grams to 100 grams of cyclobutrifluram per 100 kg of seeds.

11. 10. The method of claim 9, wherein the compound cyclobutrifluram is applied to the seeds in an amount of 10 grams to 80 grams of cyclobutrifluram per 100 kg of seeds.

12. 10. The method of claim 9, wherein the compound cyclobutrifluram is applied to the seeds in an amount of 10 grams to 40 grams of cyclobutrifluram per 100 kg of seeds.

13. Use of cyclobutrifluram or a pesticidal composition comprising cyclobutrifluram to control or prevent infestation of plants by plant-parasitic nematodes of the genus Aphelenchoides.

14. The use according to claim 13, wherein the plant-parasitic nematode is Aphelenchoides besseyi.

15. 15. The use according to claim 13 or 14, wherein the plant is selected from rice, strawberry, legumes, cowpea, soybean, cotton and ornamental species.

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