Title - URACIL COMPOUNDS AND COMPOSITION FOR THE CONTROL OF HARMFUL ARTHROPODS COMPRISING THESE COMPOUNDS

Abstract

The present provides a compound represented by formula (1), which has excellent efficacy in controlling a harmful arthropod.

Description

URACIL COMPOUNDS AND COMPOSITION FOR THE CONTROL OF HARMFUL ARTHROPODS COMPRISING THESE COMPOUNDS TECHNICAL FIELD

[0001] This application claims priority and benefit from Japanese patent application No. 2018-128122 filed on July 5, 2018, the full content of which is incorporated herein by reference. The present invention relates to a uracil compound and a composition for controlling harmful arthropods. PREVIOUS TECHNIQUE [0002 ] To date, several compounds have been developed and are in practical use to control harmful arthropods (see non-patent document 1). In addition, one compound represented by formula (B): (B) (hereinafter referred to as "compound B") is described as a wilting agent (see document of IF-2019-90960353 -ARN-AR#PIRI Page 1 of 15 patent 1). LIST OF APPOINTMENTS PATENT DOCUMENT

[0003] Patent Document 1: US Patent No. 7.157.579 B2 DOCUMENT NOT PATENT

[0004] Non-patent document 1: "The Pesticide Manual" - 17th edition (published by BCPC) ISBN 978-1-901396-88-1 SUMMARY OF THE INVENTION (PROBLEMS TO BE SOLVED BY THE INVENTION) [ 0005 ] An objective of the present invention is to provide a compound that has an excellent control effect against harmful arthropods. (MEANS TO SOLVE PROBLEMS) [ 0006 ] The present inventor has intensively studied the aforementioned problems, and found that a compound represented by the following formula (A) has excellent efficacy in controlling harmful arthropods, IF-2019-90960353-APN-ANP#INPI Page 2 of 15 which, in this way, made the present invention. The present invention is as follows. [1] A compound represented by the formula (A): (A) (hereinafter referred to as "compound A"). [2] A composition comprising the compound according to [1] above and an inert carrier (hereinafter referred to as the "present composition" or the "composition of the present invention"). [3] A method for controlling a harmful arthropod, comprising applying an effective amount of the compound according to [1] above to a harmful arthropod or a habitat where a harmful arthropod lives (hereinafter referred to as the "present control method" or the "control method of the present invention"). [EFFECT OF THE INVENTION]

[0007] The present invention can control harmful arthropods. METHOD FOR CARRYING OUT THE INVENTION IF-2019-9096035 3 -APN-ANP#INPI Page 3 of 15 [ 0008 ] The composition of the present invention comprises compound A and an inert carrier. The composition of the invention is usually prepared by mixing compound A with the inert carrier, such as, for example, a solid carrier and a liquid carrier and the like, and if necessary, by adding a surfactant and other formulation aids to prepare emulsifiable concentrates, oily solutions, powders, granules, wettable powders, water-dispersible granules, fluids, dry fluids, microcapsules, and others. The composition of the present invention usually comprises 0.0001 to 95% by weight of compound A.

[0009] Examples of solid carriers to be used in the formulation include fine powders or granules of clays (e.g., kaolin clay, diatomaceous earth, dentonite, or acidic white clay), dry silica, wet silica, talc, ceramics, other inorganic minerals (e.g., sericite, quartz, sulfur, active cardon, or calcium cardonate), or chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, or ammonium chloride), and others, as well as synthetic resins (e.g., polyester resins such as polypropylene, polyacrylonitrile, polymethyl methacrylate, or terephthalate). IF-2019-90960353-APN-ANP#INPI Page 4 of 15 polyethylene; nylon resins (for example, nylon-6, nylon-11 or nylon-66); polyamide resins; polyvinyl chloride, polyvinylidene chloride, vinyl chloride and propylene copolymers, and others).

[0010] Examples of liquid carriers include water; alcohols (e.g., methanol or ethanol); ketones (e.g., acetone or methyl ethyl ketone); aromatic hydrocarbons (e.g., toluene or xylene); aliphatic hydrocarbons (e.g., hexane or cyclohexane); esters (e.g., ethyl acetate or butyl acetate); nitriles (e.g., acetonitrile); ethers (e.g., diisopropyl ether or diethylene glycol dimethyl ether); amides (e.g., N,N-dimethylformamide); sulfoxides (e.g., dimethyl sulfoxide); and vegetable oils (e.g., soybean oil or cottonseed oil).

[0011] Examples of surfactants include non-ionic surfactants such as, e.g., polyoxyethylenated alkyl ethers, polyoxyethylenated alkyl aryl ethers, and polyethylene glycol fatty acid esters; and anionic surfactants such as, e.g., alkyl sulfonates, alkylbenzene sulfonates, and alkyl sulfates.

[0012] Examples of other auxiliary agents for IF-2019-9096035 3 -APN-ANP#INPI Page 5 of 15 formulations include a binder, a dispersant, a colorant and a stabilizer, and their specific examples include casein, gelatin, polysaccharides (e.g. starch, gum arabic, cellulose derivatives or alginic acid), lignin derivatives, bentonite, synthetic water-soluble polymers (e.g. polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids); isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).

[0013] Examples of harmful arthropods against which compound A is effective include the following.

[0014] Hemipteran pests: Delphacids (for example, Laodelphaxstriatellus, Nilaparvatalugens, Sogatellafurcifera, Peregrinusmaidis, Javesellapellucida, Perkinsiellasaccharicida or Tagosodesorizicolus) ; Cicadélidos (e.g., Nephotettixcincticeps, Nephotettixvirescens, Nephotettixnigropictus, Recilia dorsalis, Empoascaonukii, Empoascafabae, Dalbulusmaidiso Cofana spectra); Cercopidae (e.g., Mahanarvaposticata or Mahanarvafimbriolata); IF-2019-90960353-APN-ANP#INPI Page 6 of 15 Aphids (e.g., Aphis fabae, Aphis glycines, Aphis gossypii, Aphis pomi, Aphis spiraecola, Myzuspersicae, Brachycaudushelichrysi, Brevicorynebrassicae, apple ash aphid (Dysaphisplantaginea), Lipaphiserysimi, Macrosiphum euphorbias, Aulacorthumsolani, Nasonoviaribisnigri, Rhopalosiphumpadi, Rhopalosiphummaidis, Toxopteracitricidus, Hyalopteruspruni , Melanaphissacch^ri, Tetraneuranigriabdominalis, Ceratovacunalanigera and Eurasium); Phylloxeridae (e.g., Daktulosphairavitifoliae, pecan phylloxera (Phylloxeradevastatrix) , pecan leaf phylloxera (Phylloxeranotabilis), or southern pecan leaf phylloxera (Phylloxerarussellae)) ; Adelgidae (e.g., Adelgessugae, Adelgespiceae, or Aphrastasiapectinatae) ; Pentatomidae (for example, Scotinopharalurida, black rice bug (Scotinopharacoarctata), Nezaraantennata, Eysarcorisaeneus, Eysarcorislewisi, Eysarcorisventralis, Eysarcorisannamita, Halyomorphahalys, Nezaraviridula, marbled brown bedbug (Euschistusheros), insect red-listed apestos (Piezodorusguildinii), Oebaluspugnax, Dichelopsmelacanthus); Cydnids (for example, burrowing insects (Scaptocoriscastanea)) ; Alidids (e.g., Riptortuspedestris, IF-2019-90960353-APN-ANP#INPI Page 7 of Leptocorisachinensis or Leptocorisaacuta) ; Coreidae (e.g., Cletus punctiger or Leptoglossusaustralis) ; Ligeidos (e.g., Cavereliussaccharivorus, Togo hemipterus or Blissusleucopterus); Miridae (e.g., Trigonotyluscaelestialium, Stenotusrubrovittatus, Stenodemacalcarata or Lyguslineolaris); Aleurodids (e.g., Trialeurodesvaporariorum, Bemisiatabaci, Dialeurodescitri, Aleurocanthusspiniferus, Aleurocanthuscamelliae or Pealiuseuryae); Diaspididae (e.g., Abgrallaspiscyanophylli, Aonidiellaaurantii, Diaspidiotusperniciosus, Pseudaulacaspispentagona, Unaspisyanonensis or One-dimensional ); Coccidae (e.g., Ceroplastesrubens); Margarodidae (e.g., Iceryapurchasi o Iceryaseychellarum) ; Pseudococcidae (e.g., Phenacoccussolani, Phenacoccussolenopsis, Pianococcuskraunhiae, Planococcus comstocki, Pianococcus tri, Pseudococcuscalceolariae, Pseudococcuslongispinus o Brevenniarehi) ; Psyllids (e.g., Diaphorinacitri, Triozaerytreae, Cacopsyllapyrisuga, Cacopsyllachinensis, IF-2019-90960353 -APN-ANP#I^JPI Page 8 of Bactericeracockerelli or pear psylla (Cacopsyllapyricola)) ; Tingids (for example, Corythuchacilia ta, Corythuchamarmorata, Stephanitis nashi or Stephanitispyrioides) ; Cimicids (for example, Cimexlectularius) ; Cycads (eg, common cicada (Quesada gigas)); water Triatoma spp. (for example, Triatomainfestans).

[0015] Lepidopterans Crambidae (for example, Chilosuppressalis, barrenador of the dark head (Chilopolychrysus), barrenador of the tallow white (Scirpophagainnotata), Scirpophagaincertulas, Rupelaalbina, Cnaphalocrocismedinalis, Marasmiapatnalis, Marasmiaexigua, Notarchaderogata, Ostriniafurnacalis, gusano barrenador europeano (Ostrinianubilalis), Hellulaundalis, Herpetogrammalucuosa le, Pediasaterellus, Nymphuladepunctalis or sugar cane borer (Diatraeasaccharalis) ; Pyralids (for example, Elasmopalpuslignosellus, Plodiainterpunctella or Euzopherabatangensis); Noctuidos (for example, Spodopteralitura, Spodopterexigua, Mythimnaseparata, Mamestrabrassicae, Sesamiainferens, Spodopteramauritia, Narangaaenescens, IF-2019-90960353-APN-ANP#^PI Page 9 of 15 Spodopterafrugiperda, Spodopteraexempta, Agrotisipsilon, Autographanigrisigna, Plusiafestucae, soybean worm (Chrysodeixisincludens), Trichoplusia spp., Heliothis spp. (e.g., Heliothisvirescens), Helicoverpa spp. (e.g., Helicoverpaarmigera or Helicoverpazea), legume caterpillar (Anticarsiagemmatalis), leaf caterpillar (Alabama argillacea) or hop sander (Hydraeciaimmanis)); Pierides (for example, Pierisrapae); Tortricidae (e.g., Grapholitamolesta, Grapholitadimorpha, Leguminivoraglycinivorella, Matsumuraesesazukivora, Adoxophyesoranafasciata, Adoxophyeshonmai, Homonamagnanima, Archipsfuscocupreanus, Cydiapomonella, Tetramoeraschistaceana, bean shoot borer (Epinotiaaporema) or citrus fruit borer (Ecdytolophaaurantiana)); Gracillariidae (for example, Caloptiliatheivora or Phyllonorycterringoniella); Carposinidae (for example, Carposinasasakii); Lionetids (e.g., coffee leaf miner (Leucopteracoffeela), Lyonetiaclerkella or Lyonetiaprunifoliella); Limantrines (e.g., Lymantria spp. (e.g., Lymantriadispar) or Euproctis SPP (e.g., Euproctispseudoconspersa)); IF-2019-90960353 -APN-ANP^PI Page 10 of 15 Pluteliidae (e.g., Plutellaxylostella); Gelechiids (for example, Anarsialineatella, Helcystogrammatriannulellum, Pectinophoragossypiella, Phthorimaeaoperculella or Tutaabsolut); Arctines (for example, Hyphantria cunea); Castniids (e.g., giant sugarcane borer (Telchinlicus)); Sewn (for example, Cosusinsularis); Geometrids (for example, Ascotisselenaria); Limacodidae (e.g., Parasalepida); Stathmopodidae (e.g. Stathmopodamasinissa); Sphinx moths (for example, Acherontialachesis); Light-winged moths (e.g. Nokonaferalis, Synanthedon hector or Synanthedon tenuis); Hesperides (for example, Parnaraguttata); and Tinedae (for example, Tinea translucens or Tineolabisselliella).

[0016] Thysanoptera Thripidae (e.g. Frankliniellaoccidentalis, Thripspalmi, Scirtothrips dorsalis, Thripstabaci, Frankliniellaintonsa, Stenchaetothripsbiformis or Echinothripsamericanus); and Phlaeothripidae (for example, Haplothripsaculeatus).

[0017] IF-2019-90960353 -APN-ANPJIjMPI Page 11 of 15 The method for controlling harmful arthropods of the present invention comprises applying an effective amount of compound A to the harmful arthropods directly and / or to the habitat where a harmful arthropod lives (e.g., a plant or the soil).

[0018] An application rate of compound A is usually within a range of 1 to 10,000 g per 10,000 m2. When compound A is formulated in emulsifiable concentrates, wettable powders, fluids, and others, these formulations are usually applied after diluting them with water, so that the concentration of the active ingredient is within a range of 0.01 to 10,000 ppm, and in the case of being formulated in powder, granule, and other formulations, these formulations are used as is.

[0019] Furthermore, the composition of the present invention can be used in the form of an agent to control harmful arthropods in agricultural land such as, for example, fields, parcelled land, lawns, and orchards. EXAMPLES

[0020] From here on, the present invention is explained IF-2019-9096035 3 -APN-ANP#INPI Page 12 of 15 in detail by means of an example of preparation and test examples and the like; however, the present invention shall not be limited to these examples. Examples of preparation of compound A are shown below.

[0021] Example of preparation To a mixture of 2.00 g of (3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-l-yl]phenoxy}-2-pyridyloxy) acetic acid, which was prepared by the method described in the descriptive memorandum of U.S. Patent No. 6,537,948 B2, 8.01 g of xylene and 0.05 g of boron diethyl ether trifluoride complex were added dropwise, and 1.61 g of a solution containing 40% ethyl diazoacetate in xylene at 50 °C, and the mixture was stirred for 4 hours. To the resulting mixture were subsequently added 0.05 g of the boron diethyl ether trifluoride complex and 1.94 g of a solution containing 40% ethyl diazoacetate in xylene, and the mixture was stirred at 50 °C for 1 hour. The resulting mixture was allowed to cool to room temperature, and 10% aqueous sulfuric acid solution was added, and the mixture was extracted with ethyl acetate.The resulting organic layer was washed with saturated aqueous sodium bicarbonate solution, and concentrated to IF-2019-90960353 -APN-ANPJ^JPI Page 13 of 15 reduced pressure. The resulting residue was subjected to silica gel chromatography to obtain 1.01 g of compound A. The 1H-NMR data for compound A are shown below. NMR s), 5.12-4.99 (2H, m), 4.63 (2H, s), 4.20 (2H, q, J = 7.1 Hz), 3.51 (3H, s), 1.27 (3H, t, J = 7.1 Hz).

[0022] The following trial examples are used to demonstrate the effectiveness of compound A in controlling harmful arthropods. Hereafter, the term "part(s)" means "part(s) by weight."

[0023] Essay example 1 Thirty-five parts of a mixture of polyoxyethylene alkyl ether ammonium sulfate salt and wet silica (1:1 weight ratio), twenty parts of compound A, and forty-five parts of water were thoroughly mixed. The resulting mixture was diluted with water containing 0.03% v / v Shindain (registered trademark) to prepare a dilute solution containing 500 ppm of compound A. The dilute solution was sprayed onto the cabbage (Brassicaeoleracea) seedling (at the stage of IF-2019-90960353-APN-ANPJ^PI Page 14 of 15 development of the second to third true leaf) which was planted in a container at a ratio of 20 ml / seedling. From there, the stem and leaf were cut and placed inside the container, which was covered with filter paper. Five diamondback moths in the second larval stage (Plutella xylostella) were released into the container, and it was left to stand at 25°C for 5 days. The surviving insects were then counted, and mortality was calculated using the following equation; the result was 100%. Mortality (%) = (1 - number of surviving insects / 5) x 100. [ 0024 ] Example of a comparative essay 1 The trial was conducted according to trial example 1 by using compound B instead of compound A. As a result, mortality was 0%. Industrial Applicability

[0025] Compound A shows an excellent control effect against harmful arthropods. IF-2019-90960353-APN- PI Page 15 of 15 Argentine Republic - National Executive Branch 2019 - Year of Exports Additional Signature Sheet Graphic Report Number: IF-2019-909603 5 3 -APN-ANP#INPI CITY OF BUENOS AIRES Monday, October 7, 2019 Reference: 20190101879 The document was imported by the GEDO system with a total of 15 page(s). Digitally signed by GESTION DOCUMENTAL ELECTRONICA - GDE DN: cn=ELECTRONIC DOCUMENTARY MANAGEMENT - GDE, c=AR, o=GOVERNMENT SECRETARY OF MODERNIZATION, ou=ADMINISTRATIVE MODERNIZATION SECRETARY, serialNumber=CUIT 30715117564 Date: 2019.10.07 12:50:04-03'00' Marcelo Esteban Rubino Administrative Assistant National Patent Administration National Institute of Industrial Property Digitally signed by GESTION DOCUMENTAL ELECTRONICA GDE DN: cn=GEST10N DOCUMENTAL ELECTRONICA - GDE, c=AR, o=SECRETARIA DE GOBIERNO DE MODERNIZACION, ou=SECRETARIA DE MODERNIZACION ADMINISTRATIVA, serialNumber=CUIT 30715117564 Date: 2019.10.07 12:50:04 -03'00'

Claims

1. A compound characterized in that it is represented by the formula (A): (FORMULA). 2 Claims follow