Patent Application
20250017210
The present invention relates to a composition comprising a combination of insecticidal active ingredients, to the preparation of such compositions, and to a method of using such a composition to control pests in crops of useful plants.
Insecticidal compositions containing combinations of the insecticidal active ingredient spiropidion with another active ingredient are known, eg, from WO 2013/079564. In certain compositions for use in insect control on crop plants, the stability of the composition when formulated may be adversely affected by exposure of the formulation to temperature variations (low or high) when in use or when in storage prior to use. Clearly, such formulation stability is critical to the viability and performance of the composition for insecticidal use. Accordingly, there remains a strong motivation to develop insecticidal compositions where for practical purposes the composition (eg, a suspension concentrate formulation) retains stability over a range of temperatures for prolonged periods.
According to the present invention, there is provided a pesticidal composition comprising:
As is known in the art, pesticidal compositions comprising spiriopidion and abamectin have, for practical purposes, a very advantageous level of activity in controlling insect pests in crops of useful plants after foliar or soil application, whilst also maintaining acceptable crop safety (phytotoxicity) outcomes once applied to a crop at a suitable dilution. By activity, it is meant that these compositions are capable of killing or controlling insects, retarding the growth or reproduction of insects, reducing an insect population, and/or reducing damage to plants caused by insects.
Surprisingly, it has been found that the inclusion of a dispersant system comprising an acrylic graft copolymer in compositions (formulations) comprising spiropidion and abamectin as active ingredients significantly improves the formulation stability at varying temperatures. This stabilisation may include the prevention of flocculation of the solid components at low temperature (−10/10° C. cycling) and crystal growth affecting particle distribution at higher temperatures (40° C.) than may be observed when other dispersing agents known in the art are used. Such low and high temperatures may be indicative of storage conditions for such agrochemical formulations.
Further according to the invention, there is provided an aqueous composition comprising the pesticidal composition according the invention, optionally further comprising one or more adjuvants or carriers.
Still further according to the invention, there is provided a (non-therapeutic) method of combating and controlling pests which comprises applying to a pest, to a locus of a pest, or to a crop of a useful plant susceptible to attack by a pest a composition according to the invention.
Spiropidion ([3-(4-chloro-2,6-dimethyl-phenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5] dec-3-en-4-yl] ethyl carbonate. CAS no.: 1229023-00-0) is known inter alia from WO 2010/066780, WO 2018/114648 and WO 2018/114649. Abamectin (avermectin B1. CAS no.: 71751-41-2) is known inter alia from U.S. Pat. No. 4,310,519. Certain pesticidal mixtures comprising spiropidion and abamectin as active ingredients are known from WO 2013/079564.
Preferably, the composition according to the present invention is a suspension concentrate (SC), which is a stable suspension of a solid pesticidal active ingredient compound or mixture of compounds in a liquid, usually intended for dilution with water (in a spray tank or other vessel) before use. The compositions of the present invention may be made up to 100% by weight with the addition of water.
A dispersant or a dispersing agent is typically a surfactant substance, which when added to a suspension of solid particles in a liquid better enables the separation of the particles to avoid their settling or clumping together.
The dispersing agent used in combination in accordance with the present invention may comprise an acrylic graft copolymer which is a 2-methyl-2-propenoic acid and methyl 2-methyl-2-propenoate polymer with α-methyl-Ω-hydroxypoly (oxy-1,2-ethanediyl) graft. In certain embodiments, this may be otherwise defined as a methyl methacrylate/methacrylic acid/monomethoxypolyethylene glycol (PEG) methacrylate graft copolymer (eg, Atlox™ 4913, Uniqema Surfactants Ltd, UK). Such surfactant component may have a minimum number average molecular weight of 2,500 to 3000 Da, and preferably 2,650 to 2,800 Da.
Preferably, the dispersing agent (acrylic graft copolymer solution) has a hydrophilic-lipophilic balance (HLB) of 11 to 13.
Preferably, at 20° C., the dispersing agent (acrylic graft copolymer solution) used in accordance with the invention has a density of 1.0 to 1.2 g/mL of the solution, more preferably 1.05 to 1.15 g/mL, and even more preferably, 1.05 to 1.10 g/mL.
Preferably, the dispersing agent (acrylic graft copolymer solution) is present at 2 to 4% by weight of the total composition according to the invention.
Preferably, the compositions according to the invention comprise as the pesticidal active ingredient component (i) 8 to 10% by weight of spiropidion and (ii) 1 to 2% by weight of abamectin of the total composition. The compositions according to the invention comprise as the pesticidal active ingredient component spiropidion and abamectin, respectively, preferably in a weight ratio of 7:1 to 5:1, and more preferably, 7:1 to 6:1.
Preferably, in an aqueous composition according to the invention (eg, a tank mix preparation for applying to a crop), the adjuvant is selected from a mineral oil, a vegetable oil, an esterified vegetable oil, a methylated vegetable oil or an alkyl ester phosphate-based adjuvant. A pesticide adjuvant may be defined as a substance present in a pesticidal composition (eg, a concentrated active ingredient formulation diluted in water in a tank for a foliar spray application on a crop), which improves pesticidal active ingredient performance, for example by facilitating the spreading of the active ingredient on a leaf surface or penetration into the leaf of the crop plant.
Examples of adjuvant classes, which may be used in accordance with the present invention include a mineral oil, a vegetable oil, an esterified vegetable oil, a methylated vegetable oil or an alkyl ester phosphate-based adjuvant. Commercially-available adjuvant products which may be tank-mixed to yield a spray fomulation with the composition of the present invention include HASTEN™ (Victorian Chemical Co. Pty. Ltd.—blend of an esterified vegetable oil and non-ionic surfactants), OCHIMAR (Syngenta—alkyl ester of phosphoric acid (EC formulation)), LEDNA™ (Polaquimia—EC formulation comprising a methyl ester of soybean oil), Atplus® 463 (CRODA Europe Limited—60% parafin oil with surfactant blend), Actirob® B (Bayer AG—rapeseed oil methyl ester (esterified vegetable oil)), Destiny® HC (Winfield Solutions LLC—methylated soybean oil), DYNE-AMIC® (HELENA—blend of (methylated) vegetable oil and organosilicone-based nonionic surfactants), and FS Optique™ (GROWMARK, Inc—methyl ester of canola oil).
Dispersing agents which may additionally be used in accordance with the present invention include, but are not limited to, lignosulphonate salts (eg, Ufoxane 3A, Borregard AS; Borresperse NA, Borregard AS; Polyfon™ H, Ingevity; Marasperse CBOS-4 powder, LignoTech), naphthalene sulfonic acid salts (eg, Dispergator B Gran, TFL Ledertechnik GmbH), a co-polymer of 2,5-furandione and 2,4,4-trimethylpentene (eg, Geropon® Ta/72, Solvay), sodium alkyl naphthalene sulfonate formaldehyde condensate (eg, Morwet D-425, Nouryon Surface Chemistry AB, Sweden. CAS no.: 9084-06-4 ((C10H8O3S·CH2O)n·xNa)). In a preferred embodiment of the invention, a further dispersing agent may be 0.2 to 1.0% by weight, and preferably, 0.2 to 0.5% by weight, of a sodium alkyl naphthalene sulfonate formaldehyde condensate, eg, Morwet D-425.
An anti-foaming agent is a chemical additive that reduces and hinders the formation of foam in a composition, such as a pesticidal formulation. Anti-foaming agents which may be used in accordance with the present invention include, but are not limited to, polydimethylsiloxanes (eg, XIAMETER™ ACP-1500, Dow, Inc; Antifoam MSA, Univar; Xiameter ACP-0001, Dow Brasil; Xiameter ACP-0100, Dow Chemical).
Preferably, the compositions according to the invention comprise 0.1 to 2% by weight of a buffering agent. Preferably, the buffering agent is an organic acid that contains 1, 2 or 3 carboxylic acid groups. More preferably, the organic acid is a tricarboxylic acid (ie, contains three carboxylic acid groups) such as citric acid, or a sodium or potassium salt thereof.
Preferably, the compositions according to the invention comprise 5 to 10% by weight of 1,2-propylene glycol, and more preferably, 7 to 8% by weight of 1,2-propylene glycol.
Preferably, the compositions according to the invention comprise 0.1 to 2% by weight of a thickening agent, which may be selected from a natural gum substance, such as guar gum or xanthan gum, or a montmorillonite-type clay (eg, Bentopharm™ 20, Wilfrid Smith, UK).
Examples of pests which may be controlled in accordance with the compositions of the present invention include those:
Examples of soil-inhabiting pests, which can damage a crop in the early stages of plant development, are:
In particular, the compositions of the invention may be applied against insects from the order Homoptera (in particular, white flies, aphids, psyllids and armoured and soft scales), Thysanoptera (thrips), Acarina (mites) and Lepidoptera (butterflies and moths, and larva thereof). Preferably, the compositions of the invention may be applied against white flies, mites, aphids, thrips.
Crops of useful plants in which the compositions according to the invention can be used include perennial and annual crops, such as berry plants for example blackberries, blueberries, cranberries, raspberries and strawberries; cereals for example barley, maize (corn), millet, oats, rice, rye, sorghum triticale and wheat; fibre plants for example cotton, flax, hemp, jute and sisal; field crops for example sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea and tobacco; fruit trees for example apple, apricot, avocado, banana, cherry, citrus (oranges, lemons, grapefruit, limes), nectarine, peach, pear and plum; grasses for example Bermuda grass, bluegrass, bentgrass, centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass; herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes for example beans, lentils, peas and soya beans; nuts for example almond, cashew, ground nut, hazelnut, peanut, pecan, pistachio and walnut; palms for example oil palm; ornamentals for example flowers, shrubs and trees; other trees, for example cacao, coconut, olive and rubber; vegetables for example asparagus, aubergine, broccoli, cabbage, carrot, cucumber, garlic, lettuce, marrow, melon, watermelon, okra, onion, leek, pepper, chili, potato, pumpkin, squash, rhubarb, spinach and tomato; and vines for example grapes. The compositions of the invention can also be applied on turf, lawn and pastures.
Preferably, the compositions of the invention may be applied to a crop of a useful plant selected from:
Preferably, the composition of the invention may be applied to a crop of a useful plant selected from tea, cucumber, melon, watermelon, citrus, strawberry, eggplant, tomato, pepper, chili, okra.
In an aqueous composition comprising the pesticidal composition according to the invention (eg, a tank-mix composition), there may be added a further component comprising a pesticidal active ingredient selected from one or more of:
Acequinocyl, Acetamiprid, Acetoprole, Acrinathrin, Acynonapyr, Afidopyropen, Afoxalaner, Alanycarb, Allethrin, Alpha-Cypermethrin, Alphamethrin, Amidoflumet, Aminocarb, Azocyclotin, Bensultap, Benzoximate, Benzpyrimoxan, Betacyfluthrin, Beta-cypermethrin, Bifenazate, Bifenthrin, Binapacryl, Bioallethrin, Bioallethrin S)-cyclopentylisomer, Bioresmethrin, Bistrifluron, Broflanilide, Brofluthrinate, Bromophos-ethyl, Buprofezine, Butocarboxim, Cadusafos, Carbaryl, Carbosulfan, Cartap, CAS number: 1472050 Apr. 6, CAS number: 1632218-00-8, CAS number: 1808115-49-2, CAS number: 2032403-97-5, CAS number: 2044701-44-0, CAS number: 2128706 May 6, CAS number: 2249718-27-0, Chlorantraniliprole, Chlordane, Chlorfenapyr, Chloroprallethrin, Chromafenozide, Clenpirin, Cloethocarb, Clothianidin, 2-chlorophenyl N-methylcarbamate (CPMC), Cyanofenphos, Cyantraniliprole, Cyclaniliprole, Cyclobutrifluram, Cycloprothrin, Cycloxaprid, Cycloxaprid, Cyenopyrafen, Cyetpyrafen (or Etpyrafen), Cyflumetofen, Cyfluthrin, Cyhalodiamide, Cyhalothrin, Cypermethrin, Cyphenothrin, Cyproflanilide, Cyromazine, Deltamethrin, Diafenthiuron, Dialifos, Dibrom, Dicloromezotiaz, Diflovidazine, Diflubenzuron, dimpropyridaz, Dinactin, Dinocap, Dinotefuran, Dioxabenzofos, Emamectin, Empenthrin, Epsilon-momfluorothrin, Epsilon-metofluthrin, Esfenvalerate, Ethion, Ethiprole, Etofenprox, Etoxazole, Famphur, Fenazaquin, Fenfluthrin, Fenitrothion, Fenobucarb, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyroxymate, Fensulfothion, Fenthion, Fentinacetate, Fenvalerate, Fipronil, Flometoquin, Flonicamid, Fluacrypyrim, Fluazaindolizine, Fluazuron, Flubendiamide, Flubenzimine, Flucitrinate, Flucycloxuron, Flucythrinate, Fluensulfone, Flufenerim, Flufenprox, Flufiprole, Fluhexafon, Flumethrin, Fluopyram, Flupyradifurone, Flupyrimin, Fluralaner, Flupentiofenox, Fluvalinate, Fluxametamide, Fosthiazate, Gamma-Cyhalothrin, Gossyplure™, Guadipyr, Halofenozide, Halofenozide, Halofenprox, Heptafluthrin, Hexythiazox, Hydramethylnon, Imicyafos, Imidacloprid, Imiprothrin, Indoxacarb, lodomethane, Iprodione, Isocycloseram, Isothioate, Ivermectin, Kappa-bifenthrin, Kappa-tefluthrin, Lambda-Cyhalothrin, Lepimectin, Lufenuron, Metaflumizone, Metaldehyde, Metam, Methomyl, Methoxyfenozide, Metofluthrin, Metolcarb, Mexacarbate, Milbemectin, Momfluorothrin, nicofluprole Niclosamide, Nitenpyram, Nithiazine, Omethoate, Oxamyl, Oxazosulfyl, Parathion-ethyl, Permethrin, Phenothrin, Phosphocarb, Piperonylbutoxide, Pirimicarb, Pirimiphos-ethyl, Polyhedrosis virus, Prallethrin, Profenofos, Profenofos, Profluthrin, Propargite, Propetamphos, Propoxur, Prothiophos, Protrifenbute, Pyflubumide, Pymetrozine, Pyraclofos, Pyrafluprole, Pyridaben, Pyridalyl, Pyrifluquinazon, Pyrimidifen, Pyrimostrobin, Pyriprole, Pyriproxyfen, Resmethrin, Sarolaner, Selamectin, Silafluofen, Spinetoram, Spinosad, Spirodiclofen, Spiromesifen, Spirotetramat, Sulfoxaflor, Tebufenozide, Tebufenpyrad, Tebupirimiphos, Tefluthrin, Temephos, Tetrachloraniliprole, Tetradiphon, Tetramethrin, Tetramethylfluthrin, Tetranactin, Tetraniliprole, Theta-cypermethrin, Thiacloprid, Thiamethoxam, Thiocyclam, Thiodicarb, Thiofanox, Thiometon, Thiosultap, Tioxazafen, Tolfenpyrad, Toxaphene, Tralomethrin, Transfluthrin, Triazamate, Triazophos, Trichlorfon, Trichloronate, Trichlorphon, Triflumezopyrim, Tyclopyrazoflor, Zeta-Cypermethrin.
The pesticidal compositions of the present invention may be prepared according to standard procedures known in the art.
As already indicated, the pesticidal compositions of the present invention have, for practical purposes, a very advantageous level of activity in controlling insect pests in crops of useful plants after foliar or soil application, whilst also maintaining acceptable crop safety (phytotoxicity) outcomes. Further, the compositions of the present invention when in an agrochemical formulation may possess any number of other benefits compared to other compositions including, inter alia, the prevention of sedimentation, thickening, phase separation, cloudiness, foaming or crystal growth, chemical stability of the spiropidion active ingredient (degradation), long-term formulation stability (eg, at high temperature, such as 45° C.), or reduced clogging of spray nozzles during application and spray drift.
The Examples which follow serve to illustrate the invention, and in particular, demonstrate the formulation stablisation benefits of the use of a dispersing agent in accordance with the present invention (ie, Atlox™ 4913) against a polyalkylene glycol ether dispersant system known in the art, ie, ATLAS™ G-5000D (Croda, UK). Table 1 (below) describes the components of a composition D (as a suspension concentrate) according to the invention and a composition C (as a suspension concentrate), which is not according to the invention.
The remainder of the compositions D and C are made up to 100% by weight with water. Compositions D and C are prepared according to routine methods.
Storage at −10/10° C. cycling (low temperature) for 8 weeks of compositions D and C resulted in the flocculation of active ingredient particles in the suspension concentrate compositions for composition C and not for composition D, thus resulting in a failure for composition C at low temperature.
Additionally, storage at 40° C. (high temperature) for 8 weeks of compositions D and C showed evidence of crystal growth of active ingredient particles in the suspension concentrate compositions for composition C and not for composition D, again resulting in a failure for composition C at high temperature.
Flocculation and crystal growth behaviours of the compositions D and C were assessed using conventional microscopy and/or particle size measurement techniques.
| Number | Date | Country | Kind |
|---|---|---|---|
| 21210434.3 | Nov 2021 | EP | regional |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/EP2022/082474 | 11/18/2022 | WO |
