US 20100071096A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0071096 A1 Yamada et al. (43) Pub. Date: Mar. 18, 2010

(54) PLANT DISEASE AND DAMAGE Publication Classification CONTROL COMPOSITION AND PLANT (51) Int. Cl. DISEASE AND INSECT DAMAGE AOIH 5/10 (2006.01) PREVENTION METHOD AOIN 55/10 (2006.01) AOIN 25/26 (2006.01) (75) Inventors: Eiichi Yamada, Chiba (JP): AOIH 5/00 (2006.01) Ryutaro Ezaki, Shiga (JP); AOIH 5/02 (2006.01) Hidenori Daido, Chiba (JP) AOIH 5/08 (2006.01) AOIP3/00 (2006.01) Correspondence Address: BUCHANAN, INGERSOLL & ROONEY PC (52) U.S. Cl...... 800/295: 514/63; 504/100 POST OFFICE BOX 1404 (57) ABSTRACT ALEXANDRIA, VA 22313-1404 (US) The invention provides a plant disease and insect damage control composition including, as active ingredients, dinote (73) Assignee: Mitsui Chemicals, Inc., Minato-ku furan and at least one fungicidal compound; and a plant (JP) disease and insect damage prevention method that includes applying Such a composition to a plant body, Soil, plant seed, (21) Appl. No.: 12/516,966 stored cereal, stored legume, stored fruit, stored vegetable, silage, stored flowering plant, or export/import timber. The (22) PCT Filed: Nov. 22, 2007 invention provides a new plant disease and insect damage (86). PCT No.: PCT/UP2007/072635 control composition and a plant disease and insect damage prevention method with very low toxicity to mammals and S371 (c)(1), fishes, the composition and method showing an effect against (2), (4) Date: May 29, 2009 plural pathogens and pest , including emerging resis tant pathogens and resistant pest insect, by application to a (30) Foreign Application Priority Data plant body, soil, plant seed, stored cereal, stored legume, stored fruit, stored vegetable, silage, stored flowering plant, Nov. 29, 2006 (JP) ...... 2006-321404 or export/import timber. US 2010/007 1096 A1 Mar. 18, 2010

PLANT DISEASE AND INSECT DAMAGE 0006. As chemicals which prevent plant disease by apply CONTROL COMPOSITION AND PLANT ing to plant seeds there are, conventionally, benomyl agents, DISEASE AND INSECT DAMAGE thiophanate-methyl agents, prochloraZ agents, pefurazoate PREVENTION METHOD agents, and the like, and it is known that these will demon strate an effect, as single agents or mixtures thereof, by spray FIELD OF THE INVENTION treatment, coating treatment, dip treatment, or dressing treat ment to seeds. How ever, among these agents, it is reported 0001. The present invention relates to a plant disease and that the control effect against rice bakanae disease of benomy1 insect damage control composition and a plant disease and and thiophanate-methyl agents is falling. Moreover, while insect damage prevention method. prochloraZ agents are applied against rice blast disease, brown spot, bakanae disease, tulip bulb rot, and shallot dry rot BACKGROUND OF THE INVENTION disease, and pefurazoate agents are applied aginst rice blast 0002. It is described in Japanese Patent Application Laid disease, brown spot, bakanae disease, wheat pink Snow mold, Open (JP-A) No. 07-179448 that an effect is shown by dinote and tulip bulb rot, other applications of there agents are not furan as an insecticidal compound, with application methods known. Moreover, mixtures of benomyl and thiuram are Such as foliar application and water application, against: applied for: rice diseases of rice blast disease, seedling blight, Lepidopterous pests, such as the common cutworm, Chilo bakanae disease, brown spot, bacterial grain rot, bacterial and the common cabbageworm; pests, such as the brown stripe and discolorations of rice; wheat-like cereal greenhouse white fly, the cotton aphid, the comstock mealy diseases of barley Stripe, loose Smut, Cephalosporium stripe bug, and the Southern green Stink bug; Coleoptera pests. Such and Scald; cucumber fusarium wilt; gummy stem blight; as the rice water weevil and the striped flea beetle; Diptera damping off tomato fusarium wilt; watermelon fusarium pests such as the house fly and the rice leaf miner; Thysan wilt; soya bean purple seed stain; taros Alternaria leaf spot: opterapests Such as onion ; Orthopterapests, such as the Sugarcane Smut, Coix lacryma-jobi leaf blight; Smut, corn Smoky brown cockroach and rice grasshopper, and the like. seedling blight; Japanese pumpkin fusarium basal rot; shal However, there are no indication that there is an effect shown lots dry rot disease; garlic white rot; and yam root rot. How for pest insect prevention by application procedures such as ever, other applications thereof are not known. Moreover, spray treatment, coating treatment, dip treatment, dressing since mixtures of benomyl and thiuram have a strong affect on treatment, fumigation and Smoking treatment, and pressure aquatic , there are warnings against their use in places injection to plant seeds. where there is a possibility of dispersal or flow into rivers, 0003 Moreover, it is described in JP-A No. 08-245322, lakes, coastal areas, and culture ponds. JP-A No. 08-245323, JP-A No. 08-29.1009, and JP-A No. 11-005708 that a composition containing dinotefuran and a DESCRIPTION OF THE INVENTION fungicidal compound shows, in the field of paddy rice culti Problem to be Solved by the Invention Vation, a synergistic effect against rice blast disease (Pyricu laria Oryzae) and sheath blight disease (Rhizoctonia Solani) 0007 An object of the invention is to provide a new pre in application methods such as to seedling raising boxes. vention composition and control method against disease and However, there is no indication that an effect is shown in pest damage to plant bodies, soil, plant seeds, stored cereals, disease prevention and insect damage prevention by applica stored legumes, stored fruits, stored vegetable, silage, stored tions of spray treatment, coating treatment, dip treatment, or flowering plants and export/import timber, wherein the pre dressing treatment to plant seeds. Furthermore, there is no vention composition and control method show an effect indication of the use of mixtures of fulsulfamide and/or against plural pathogens and pest insects, including emerging hymexaZol, with dinotefuran, nor is there any indication of a resistant pathogens and resistant pest insects, yet have a very synergistic effect due to mixed use. low toxicity to mammals and fish, the composition being 0004. It is described in JP-A 61-197553 (Japanese Patent applied to the plant body, soil, plant seeds, stored cereals, Announcement No. 06-027113) that flusulfamide, as a fun stored legumes, stored fruits, stored vegetable, silage, stored gicidal compound, shows antimicrobial activity or growth flowering plants and export/import timber. inhibition activity to various plant pathogenic microbes across a wide range of plant diseases by spraying, soil Surface Means for Solving the Problem application, Soil incorporation application, seed dipping, and 0008. As a result of carrying out diligent examination and root dust coating, root immersion of seedlings and the like, investigation, the present inventors have determined that a and flusulfamide shows a prominent effect especially against composition in which at least one sort of fungicidal com soil diseases where the number of effective control chemicals pound is added to dinotefuran shows a high preventive effect are small. Furthermore, the above document mentions the at a low dose to plural types of disease damage and insect possibility of concomitant use of flusulfamide with a pesti damage, and shows a stable preventive effect toward the cide and the like. However, there is no indication of using above resistant pathogens and/or resistant pest insects, result fluSulfamide with dinotefuran or hymexaZol, or a synergistic ing of the invention. effect thereof. 0009. That is, the means for solving problem is as follows. 0005 JP-A No. 03-227904 (Japanese Patent No. 2,860, 0010) 1. A plant disease and insect damage control com 492) and JP-A No. 08-1987 10 (Japanese Patent No. 3,608, position comprising active ingredients of (RS)-1-me 830), and JP-A No. 08-198713 (Japanese Patent No. 3,608, thyl-2-nitro-3-(tetrahydro-3-furylmethyl)guanidine 831) disclose a synergistic effect of the concomitant use of (common name: dinotefuran) and at least one fungicidal flusulfamide with a fungicidal compound, and the like. How compound selected from the group consisting of 2,4- ever, there is no indication of using flusulfamide with dinote dichloro-C.C.C.-trifluoro-4'-nitro-m-toluenesulfonanil furan. ide (common name: flusulfamide), 3-hydroxy-5-meth US 2010/007 1096 A1 Mar. 18, 2010

ylisoxazol (common name: hymexaZol), and (RS)-2-(4- BEST MODE OF CARRYING OUT THE fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3- INVENTION (trimethylsilyl)propan-2-ol (common aC. simeconazole). 0022 Specific examples of the types of disease damage 0011 2. The plant disease and insect damage control which may be prevented with the method of the invention composition according to claim 1, wherein the at least include, but are not limited to, the following: one fungicidal compound comprises 2,4-dichloro-O.C., C-trifluoro-4'-nitro-m-toluenesulfonanilide (common 0023 rice diseases such as rice blast disease (Pyricularia name: fluSulfamide). Oryzae), brown spot (Cochliobolus miyabeanus), bakanae 0012. 3. The plant disease and insect damage control disease (Gibberellafiujikuroi); composition according to claim 1, wherein the at least 0024 wheat-like cereal diseases such as barley stripe one fungicidal compound comprises 3-hydroxy-5-me (Pyrenophora graminea), loose Smut (Ustilago nuda, Usti thylisoxazol (common name: hymexaZol). lago tritici, Ustilago nigra, Ustilago avenae), bunts (Tilletia 0013 4. The plant disease and insect damage control caries, Tilletia pancicii), covered Smut (Ustilago hordei, composition according to claim 1, wherein the at least Ustilago kolleli), Scald (Rhynchosporium secalis), Septoria one fungicidal compound comprises (RS)-2-(4-fluo tritici leaf blotch (Septoria tritici), glume blotch (Lep rophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-(trimethylsilyl) tosphaeria nodorum), pink Snow mold (Microdochium propan-2-ol (common name: Simeconazole). inivale), Fusarium head blight (Fusarium graminearum, 0014) 5. The plant disease and insect damage control Fusarium culmorum, Fusarium avenaceum, Microdochium composition according to claim 1, wherein the at least inivale), kernel blight (Helminthosporium sativum), take-all one fungicidal compound comprises a mixed composi (Gaeumannomyces graminis), Cephalosporium stripe tion of at least two selected from the group consisting of (Cephalosporium gramineum) and net blotch (Dreschlera flusulfamide, hymexaZol, and Simeconazole. 0015. 6. A plant disease and insect damage prevention teres); method comprising applying the pest control composi 0025 corn diseases such as common Smut (Ustilago tion according to claim 1 to a plant body, soil, plant seed, mydis); stored cereal, stored legume, stored fruit, stored veg 0026 legume diseases such as seedling blight (Rhizoc etable, silage, stored flowering plant, or export/import tionia Solani) and Sclerotinia stem rot (Sclerothinia Scleroto timber. rium), purple seed stain of Soya beans (Cercospora kikuchii) 0016 7. The plant disease and insect damage preven and Rhizoctonia root rot (Rhizoctonia Solani); tion method according to claim 6, wherein the method of 0027 diseases in sugar beet such as root rot (Rhizotconia application to plant seeds is spray treatment, coating Solani); treatment, dip treatment, or dressing treatment of seeds. 0028 rape diseases such as black leg (Leptosphaeria 0017 8. The plant disease and insect damage preven maculans), alternaria leaf spot (Alternaria brassicae); tion method according to claim 6, wherein the method of 0029 damping off (Rhizoctonia solani) of various veg application to a stored cereal, stored legume, stored fruit, etables, such as tomato, cucumber, Japanese radish, water stored vegetable, silage, Stored flowering plants, or melon, eggplant, Sweet pepper, and spinach; and export/import timber is spray treatment, coating treat ment, dip treatment, dressing treatment, fumigation 0030) diseases such as tomato wilt (Fusarium treatment, Smoke treatment, or pressure injection. Oxysporum), cucurbitaceae Fusarium wilt (Fusarium 0018 9. Plant seed, stored cereal, stored legume, stored Oxysporum), cabbage yellows (Fusarium oxysporum), cauli fruit, stored vegetable, silage, stored flowering plant, or flower chlorosis (Fusarium oxysporum), and Chinese cab export/import timber to which the plant disease and bage Verticillium wilt (Verticillium dahlie). insect damage control composition according to claim 1 0031 Examples that may be given of the insect damage has been applied. which can be prevented include, but are not limited to, the 0019 10. The plant disease and insect damage preven following from the order of grasshoppers, crickets and locusts tion method according to claim 6, wherein the method of Examples that may be given of the insect damage which can application to a plant body or soil is foliar application to be prevented include, but are not limited to, the following a plant body, spray treatment to the Soil Surface, soil from the order of grasshoppers, crickets and locusts (Ortho incorporation after spray treatment to the soil Surface, ptera): injection treatment into the soil, or soil drenching treat 0032 BLATTIDAE such as the American cockroach ment. (Periplaneta americana), the Smokybrown cockroach 0020 11. A method of preventing plant disease and (Periplaneta fuliginosa), the Japanese cockroach (Periplan insect damage to a plant body grown from a plant seed, eta japonica); the method comprising applying, to the plant seed, the 0033 BLATTELLIDAE such as the German cockroach plant disease and insect damage control composition (Blattella germanica), the false German cockroach (Blattella according to claim 1. lituricollis); EFFECT OF THE INVENTION 0034. TETTIGONIIDAE such as the northern rice katydid 0021. The method of the invention, while demonstrating a (Homorocoryphus jezoensis), the northern rice katydid (Ho high preventive effect to disease damage and insect damage morocoryphus lineosus); generated in plant bodies, soil, plant seeds, stored cereals, 0035 GRYLLOTALPIDAE such as the mole crickets stored legumes, stored fruits, stored vegetables, silage, stored (Gryllotalpa sp.); and flowering plants, and export/import timber, also shows a 0036 ACRIDIDAE such as the short-horned grasshop stable preventive effect to microbe pathogens and pest insects pers (Oxya hyla intricata) and rice grasshopper (Oxya that are resistant to existing chemicals. yezoensis); US 2010/007 1096 A1 Mar. 18, 2010

0037 the following from the order of Termites/White 0046 PYRRHOCORIDAE such as the cotton bug (Dys (ISOPTERA): the dry-wood termite (Cryptotermes domesti dercus cingulatus), the Small cotton bug (Dysdercus poeci cus), the Formosan Subterranean termite (Coptotermes for lus); mosanus), the Japanese Subterranean termite (Reticulitermes 0047 such as the chrysanthemum lace bug speratus), the macrotermitine termite (Odontotermes formo ( spinifrons), the yanagi-gunbai (Metasalis populi), Sanus); the camphor lace bug (Stephanitis fasciicarina), the lace 0038 the following from the order of thrips (THYSAN bug (Stephanitis nashi), the azalea lace bug (Stephanitis OPTERA): 0039 such as the grass thrips (Anaphothrips pyrioides), the lace bug (Uhlerites debile), the wal obscurus), the cockSfoot thrips (Chirothrips manicatus), the nut lace bug (Uhlerites latious); chanokuro-azamiuma (Dendrothrips minowai), the flower 0048 MIRIDAE such as the alfalfa plant bug (Adelphoc thrips (Frankliniella intonsa), the yurikiiro-azamiuma (Fran Oris lineolatus), the buchihigekuro-kasumikame (Adelphoc Kliniella lilivora), the greenhouse thrips (Heliothrips haem Oris triannulatus), the koao-kasumikame (Apolygus orrhoidalis), the composite thrips (Microcephalothrips lucorum), the pale green plant bug (Apolygus spinolai), the abdominalis), the oriental Soybean thrips (Mycterothrips gly akahoshi-kasumikame (Creontiades coloripes), the tobacco cines), the mulberry thrips (Pseudodendrothrips mori), the leafbug (Nesisiocoris tenuis), the Japanese garden fleahopper yellow tea thrips (Scirtothrips dorsalis), the redbanded (Sele (Ectometopterus micantulus), the oriental garden fleahopper nothrips rubrocinctus), the oriental rice thrips (Stenchaeto (Halticiellus insularis), the apple leaf bug (Heterocordylus thrips biformis), the neglkuro-azamiuma (Thrips alliorum), flavipes), the Japanese tarnished plant bug (Lygus disponsi), the loquat thrips (Thrips coloratus), the honeysuckle thrips the madara-kasumikame (Cyphodemidea Saundersi), the (Thrips flavus), the Hawaiian flower thrips (Thrips hawaiien Sugarbeet leaf bug (Orthotylus flavosparsus), the wheat leaf sis), the chrysanthemum thrips (Thrips nigropilosus), the bug (Stenodema calcaratum), the timothy grassbug (Stenotus melon thrips (Thrips palmi), the western flower thrips (Fran binotatus), the Sorghum plant bug (Stenotus rubrovittatus), Kliniella occidentalis), the Japanese flower thrips (Thrips the brokenbacked bug (Taylorilygus pallidulus), the rice leaf setosus), the thrips (Thrips simplex), the onion bug (Trigonotylus coelestialium); thrips (Thrips tabaci); 0049 CICADIDAE such as the large brown cicada (Grap 0040 PHLAEOTHRIPIDAE such as the rice aculeated topsaltria nigrofuscata); thrips (Haplothrips aculeatus), the Chinese thrips (Haplo thrips chinensis), the hana-kudaaZamiuma (Haplothrips kur 0050 APHROPHORIDAE such as the maeki-awafuki diumovi), the red thrips (Haplothrips niger), the shi (Aphrophora costalis), the pine froghopper (Aphrophora fia ionaga-kudaaZamiuma (Leeuwania pasanii), the camphor vipes), the common spittlebug (Aphrophora intermedia), the thrips (Liothrips floridensis), the lily thrips (Liothrips himefutatennaga-awafuki (Clovia punctata), the meadow vaneeckei), the thrip (Litotetothrips pasaniae), the Japanese Spittlebug (Philaenus spumarius); gall-forming thrips (Ponticulothrips diospyrosi); 0051 TETTIGELLIDAE such as the black-tipped leaf 0041 the following from the order of the true bugs hopper (Bothrogonia japonica), the green leafhopper (Ci (HEMIPTERA): PENTATOMIDAE such as the purple stink cadella viridis); bug (Carpocoris purpureipennis), the sloe bug (Dolycoris 0.052 CICADELLIDAE such as the leafhopper (Agu baccarum), the painted bug (Eurydema pulchrum), the cab riahana quercus), the polyphagous leafhopper (Alnetoidia bage bug (Eurydema rugosum), the Two-spotted Sesame bug alneti), the citrus leafhopper (Aphelioma ferruginea), the (Eysarcoris guttiger), the Ootogeshirahoshi-kamemushi grape Leafhopper (Arboridia apicalis), the Small green leaf (Eysarcoris lewisi), the white spotted spined Stink bug hopper (Edwardsiana flavescens), the leafhopper (Ed (Eysarcoris parvus), the shieldbug (Eysarcoris ventralis), the wardsiana rosae), the pine leafhopper (Empoasca abietis), polished green Stink bug (Glaucias subpunctatus), the red the tea green leafhopper (Empoasca Onuki), the orange stripped Stink bug (Graphosoma rubrolineatum), the brown headed leafhopper (Thaia subrufa), the smaller citrus leaf malmorated Stink bug (Halyomorpha mista), the rice Stink hopper (Zyginella citri): bug (Lagynotomus elongatus), the oriental green Stink bug 0053 DELTOCEPHALIDAE such as aster leafhopper (Nezara antennata), the Southern green Stink bug (Nezara (Macrosteles fasci?ions), the green rice leafhopper (Nepho viridula), the redbanded shieldbug (Piezodorus hybneri), the tettix cincticeps), the green rice leafhopper (Nephotettix brown-winged green bugs (Plautia Stali), the black rice bug nigropictus), the green rice leafhopper (Nephotettix vire (Scotinophara lurida), the brown rice Stink bug (Starioides scens), the apple leafhopper (Orientus ishidai), the Zig-Zag degenerus); rice leafhopper (Recilia dorsalis), the wheat leafhopper (Sor 0042 COREIDAE such as the winter cherry bug (Acan hoanus tritici), the leafhopper (Speudotettix subfiscu thocoris Sordidus), the Coreid-hug (Anacanthocoris stricor lus); nis), the rice Stink bug (Cletus punctiger), the slender rice bug 0054 DELPHACIDAE such as the small brown plantho (Cletus trigonus), the Leaf-Footed Bug (Molipteryx filligi pper (Laodelphax striatellus), the brown planthopper nosa), (Nilaparvata lugens), the pale Sugarcane planthopper (Nu 0043 ALYDIDAE such as the paddy bug (Leptocorisa mata muiri), the maize planthopper (Peregrinus maidis), the acuta), the rice bug (Leptocorisa Chinensis), the rice bug Sugarcane leafhopper (Perkinsiella saccharicida), the white (Leptocorisa Oratorius), the bean bug (Riptortus clavatus); backed planthopper (Sogatella fircifera), the panicum plan 0044. RHOPALIDAE such as the carrot bug (Aeschynteles thopper (Sogatella panicicola); maculatus), the hyaline grass bug (Liorhyssus hyalinus); 0055) PSYLLIDAE such as the mulberry sucker (Ano 0045 LYGAEIDAE such as the oriental chinchbug (Cav momeura mori), the lacquer psylla (Calophya nigridorsalis), elerius saccharivorus), the bamboo chinch bug (Macropes the citrus psylla (Diaphorina citri), the hibiscus psylla (Meso obnubilus), the hiratahyoutan-nagakamemushi (Pachybrach homotoma camphorae), the abies psylla (Psylla abieti), the ius luridus), the kuroashihoso-nagakamemushi (Paromius Plant louse (Psylla alni), the sins psylla (Acizzia jamatonica), jejunus), the seed bug (Togo hemipterus); the apple Sucker (Cacopsylla mali), the black apple Sucker US 2010/007 1096 A1 Mar. 18, 2010

(Psylla malivorella), the pear Sucker (Psylla pyrisuga), the ing scale (Duplaspidiotus claviger), the purple scale (Lepi tobira psylla (Psylla tobirae), the camphor sucker (Trioza dosaphes beckii), the oystershell scale (Lepidosaphes ulmi), camphorae), the guercus Sucker (Trioza quercicola); the Japanese scale (Lepidosaphes japonica), the scale 0056 ALEYRODIDAE such as the orange spiny whitefly (Parlatoreopsis pyri), an armored scale (Parlatoria camel (Aleurocanthus spiniferus), the grape whitefly (Aleurolobus liae), the tea parlatoria scale (Parlatoria theae), the black taonabae), the tobacco whitefly (Bemisia tabaci), the citrus parlatoria Scale (Parlatoria Ziziphi), the fern Scale (Pinnaspis whitefly (Dialeurodes citri), the greenhouse whitefly (Tri aspidistrae), the camphor scale (Pseudaonidia duplex), the aleurodes vaporariorum), the silverleaf whitefly (Bemisia peony scale (Pseudaonidia paeoniae), the mulberry scale argentifolii); (Pseudaulacaspis pentagona), the white prunicola scale 0057 PHYLLOXERIDAE such as the vine phylloxera (Pseudaulacaspis prunicola), the arrowhead scale (Unaspis (Viteus vitifolii); vanonensis); 0058 PEMPHIGIDAE such as the root aphid (Aphidoun 0064 the following from the order of the butterflies, guis mali), the woolly aphid (Eriosoma lanigerum), the Sug and skippers (): swift ( arcane root aphid (Geoica lucifiiga); excrescens), the grape treeborer (), the 0059 APHIDIDAE such as the pea aphid (Acyrthosiphon moth (Palpifer sexnotata), the strawberry tortrix moth (Acil pisum), the spirea aphid (Aphis citricola), the cowpea aphid eris comariana), the Summer fruit tortrix moth (Adoxophyes (Aphis craccivora), the yanabi-aburamushi (Aphis farinosa Orana fasciata), the Smaller tea tortrix moth (Adoxophyes vanagicola), the cotton aphid (Aphis gossypii), the foxglove sp.), the Asiatic leafroller (Archips breviplicanus), the apple aphid (Aulacorthum Solani), the leafcurl plum aphid (Brachy tortrix (Archips fiascocupreanus), the brown oak tortrix (Ar caudus helichrysi), the cabbage aphid (Brevicoryne brassi chips xylosteanus), the mat rushworm (Bactra furfurana), the cae), the tulip bulb aphid (Dysaphis tulipae), the European tobacco leaf worm (Cnephasia cinereipalpana), the nut fruit aphid (Euceraphis punctipennis), the mealy plum aphid tortrix ( kurokoi), the greenish chestnut moth (Eu (Hyalopterus pruni), the turnip aphid (Lipaphis erysimi), the coenogenes aestuosa), the oriental fruit moth (Grapholita chrysanthemum aphid (Macrosiphoniella Sanborni), the molesta), the oriental tea tortrix (Homona magnanima), the potato aphid (Macrosiphum euphorbiae), the bean aphid leafroller (Choristoneura adumbratana), the Soybean pod (Megoura crassicauda), the nashikofuki-aburamushi borer (Leguminivora glycinivorella), the adzuki bean pod (Melanaphis siphonella), the apple leafcurling aphid (Myzus worm (Matsumuraeses azukivora), the Soybean pod worm malisuctus), the umekobu-aburamushi (Myzus numecola), (Matsumuraeses falcana), the Soybean pod worm (Matsumu the green peach aphid (Myzus persicae), the onion aphid raeses phaseoli), the apple fruit licker (Spilonota lechrias (Neotoxoptera formosana), the apple aphid (Ovatus malico pis), the eyespotted bud moth (Spilonota ocellana), the Euro lens), the waterlily aphid (Rhopalosiphum nymphaeae), the pean grape berry moth (Eupoecillia ambiguella), the Chinese bird-cherry aphid (Rhopalosiphum padi), the rice root aphid arrowed stemborer (Gymnidomorpha mesotypa), the yomo (Rhopalosophum rufiabdominalis), the root aphid (Sappa gioo-hosohamaki (Phtheochroides clandestina), the mul phispiri), the pearaphid (Schizaphispiricola), the gain aphid berry bagworm (Bambalina sp.), the giant bagworm (Eumeta (Sitobion akebiae), the ibarahigenaga-aburamushi (Sitobion japonica), the tea bagworm (Euneta minuscule), the Euro ibarae), the tea aphid (Toxoptera aurantii), the brown citrus pean grain moth (Nemapogon granellus), the casemaking aphid (Toxoptera citricidus), the peach aphid (Tuberoceph clothes moth (Tinea translucens), the pear leaf miner (Buc alus mononis), the taiwanhigenaga-aburamushi (Uroleucon culatrix pyrivorella), the peach leafminer (Lyonetia cler formosanum); kella), the apple leafminer (Lyonetia prunifoliella), the Soy 0060. MARGARODIDAE such as the giant mealy bug bean leafroller (Caloptilia sovella), the tea leafroller (Drosicha corpulenta), the cottony cushion scale (Iceryapur (Caloptilia theivora), the ringo-hosoga (Caloptilia Zach chasi); rysa), the persimmon leafminer (Cuphodes diospyrosella), 0061 PSEUDOCOCCIDAE such as the matsumoto mea the apple leafminer (Phyllonorycter ringoniella), the pear lybug (Crisicoccus matsumotoi), the Kuwana Pine Mealybug barkminer (Spullerina astaurota), the citrus leafminer (Phyl (Crisicoccus pini), the Taxus mealybug (Dysmicoccus wist locnistis citrella), the grape leafminer (Phyllocnistis topar ariae), the citrus mealybug (Planococcus citri), the Japanese cha), the allium leafminer (Acrolepiopsis sapporensis), the mealybug, the (Planococcus kranuhiae), the citrus mealybug yam leafminer (Acrolepiopsis suzukiella), the diamondback (Pseudococcus citriculus), the comstock mealybug (Pseudo moth (Plutella xylostella), the apple fruit moth (Argyresthia coccus Comstocki); conjugella), the vine tree borer (Paranthrene regalis), the 0062 COCCIDAE such as the Indian wax scale (Cero cherry tree borer (Synanthedon hector), the persimmon fruit plastes ceriferus), the red wax scale (Ceroplastes rubens), the moth (Stathmopoda masinissa), the Sweetpotato leaf folder mikan-hiratakaigaramushi (Coccus discrepans), the brown (Brachnia triannulella), the peach fruit moth (Carposina Soft scale (Coccus hesperidum), the citricola scale (Coccus niponensis), the pear leaf worm (Illiberispruni), the Chinese pseudomagnoliarum), the Chinese wax scale (Ericerus pela), cochlid (Parasa sinica), the oriental moth (Monema flave the European fruit lecanium scale (Lecanium corni), the scens), the pear stinging caterpillar (Narosoideus flavidorsa Europian peach scale (Lecanium persicae), the citrus cottony lis), the green cocklid (Parasa consocia), the persimmon scale (Pulvinaria aurantii), the soft scale (Pulvinaria citri cochlid (Scopelodes contracus), the rice stem borer (Chilo cola), the cottony mulberry scale (Pulvinaria kuwacola); suppressalis), the rice leaffolder moth (Cnaphalocrocis medi 0063) DIASPIDIDAE such as the kankitsu-kaigaramushi nalis), the yellow peach moth ( punctiferalis), the (Andaspis kashicola), the California red scale (Aonidiella cotton caterpillar (Diaphania indica), the nashimadara aurantii), the yellow scale (Aonidiella citrina), the coconut meiga (Ectomyelois pyrivorella), the Mediterranean flour scale (Aspidiotus destructor), the oleander Scale (Aspidiotus moth (Ephestia kuehniella), the limabean pod borer (Etiella hederae), the circular black scale (Chrysomphalus ficus), the Zinckenella), the persimmon bark borer (Euzophera batan San Jose scale (Comstockaspis perniciosa), the min gensis), the mulberry pyralid (Glyphodes pyloalis), the cab US 2010/007 1096 A1 Mar. 18, 2010

bage webworm (Hellulla undalis), the rice leafroller (Maras fused flour beetle (Tribolium confiusum), the bean blister mia exigua), the legume pod borer (Maruca testulalis), the beetle (Epicauta gorhami), the kimadara-kamikiri (Aeoles cotton leafroller (Notarcha derogate), the Asian corn borer thes chrysothrix), the white spotted longicornbeetle (Anoplo (Ostrinia firinacalis), the azuki bean borer (Ostrinia Scapu phora malasiaca), the Japanese pine Sawyer (Monochamus lalis), the butterbur borer (Ostrinia zaguliaevi), the bluegrass alternatus), the yellow-spotted longicorn beetle (Psacothea webworm (Parapediasia teterrella), the bean webworm hilaris), the grape borer (Xylotrechus pyrrhoderus), the mon (Pleuroptya ruralis), the yellow stem borer (Scirpophaga keypod round-headed borer (Xystrocera globosa), the azuki incertulas), the rice skipper (Parnara guttata), the red helen bean weevil (Callosobruchus chinensis), the cucurbit leaf (Papilio helenus), the common yellow swallowtail (Papilio beetle (Aulacophora femoralis), the chairosaru-hamushi machaon), the swallowtail butterfly (Papilio xuthus), the east (Basilepta balvi), the tortoise beetle (Cassida nebulosa), the ern pale clouded yellow (Colias erate poliographus), the tensaitobi-hamushi (Chaetocnema concinna), the Sweetpo common cabbageworm (Pieris rapae crucivora), the long tato leaf beetle (Colasposoma dauricum), the juushihoshiku tailed pea-blue (Lampides boeticus), the orange moth (Ange binaga-hamushi (Crioceris quatuordecimpunctata), the rice roma prunaria), the Japanese giant looper ( selenaria), rootworm (Donacia provosti), the ruri-hamushi (Linaeidea the phytomimetic giant geometer ( robustum), the aenea), the Soybean flea beetle (Luperomorpha tenebrosa), plum cankerworm (Cystidia couaggaria), the pine caterpillar the two-striped leaf beetle (Medythia nigrobilineata), the rice (Dendrolimus spectabilis), the tent caterpillar (Malacosoma leaf beetle (Oulema oryzae), the tropical legume leaf beetle neustria testacea), the apple caterpillar ( (Pagria signata), the daikon leaf beetle (Phaedon brassicae), japonensis), the coffee hawk moth (Cephonodes hylas), the the striped flea beetle (Phyllotreta striolata), the umechok grape horn worm (Acosmeryx castanea), the scarce choco kiri-Zoumushi (Involvulus cupreus), the peach curculio late-tip (Clostera anachoreta), the poplar prominent (Rhynchites heros), the Sweet potato weevils (Cylas formi (Clostera anastomosis), the Japanese buff-tip moth (Phalera carius), the apple blossom weevil (Anthonomus pomorum), flavescens), the oak caterpillar (Phalerodonta manleyi), the the daikonsaru-Zoumushi (Ceutorhynchus albOsuturalis), the lobster moth (Stauropus fagipersimilis), the tea tussock moth chestnut weevil (Curculio Sikkimensis), the rice plant weevil (Euproctis pseudoconspersa), the brown-tail moth (Echinocnemus squameus), the West Indian Sweetpotato (Sphrageidus similis), the oriental tussock moth (Artaxa sub weevil (Euscepes postfasciatus), the lesser clover-leaf weevil flava), the gypsy moth (Lymantria dispar), the white-spotted (Hypera nigrirostris), the alfalfa weevil (Hypera postica), the tussock moth (Orgvia thyellina), the Fall webworm moth rice water weevil (Lissorhoptrus Oryzophilus), the vegetable (Hyphantria cunea), the mulberry tiger moth (Spilosoma weevil (Listroderes costirostris), the leaf weevil (Phyllobius imparilis), the three-spotted plusia (Acanthoplusia agnata), armatus), the chibikofuki-Zoumushi (Sitona japonicus), the the eastern alchymist (Aedia leucomelas), the black cutworm rice weevil (Sitophilus oryzae), the maize weevil (Sitophilus (Agrotis ipsilon), the turnip moth (Agrotis segetum), the hibis Zeanais), the hunting billbug (Sphenophrus venatus vesti cus looper (Anomis mesogona), the beet semi-looper (Au tus): tographa nigrisigna), the cabbage looper (Trichoplusia ni), 0.066 the following from the sawfly, wasp, bee, and the cotton bollworm (Helicoverpa armigera), the capegoose order (HYMENOPTERA): the cabbage sawfly (Athalia berry budworm (Helicoverpa assulta), the flax budworm (He japonica), the turnip sawfly (Athalia rosae ruficornis), the liothis maritime), the cabbage Moth (Mamestra brassicae), apple argid sawfly (Arge mali), the large rose sawfly (Arge the rice green caterpillar (Naranga aenescens), the oriental pagana) and the oriental chestnut gall wasp (Dryocosmus armyworm (Pseudaletia separata), the pink stem borer kuriphilus); (Sesamia inferens), the lawn grass cutworm (Spodoptera dep 0067 the following from the fly order (DIPTERA): the ravata), the beet armyworm (Spodoptera exigua), the com rice crane fly (Tipula aino), the Sciarid fly (Bradysia agrestis), mon cutworm (Spodoptera litura), the apple dagger moth the Soybean pod gall midge (Asphondylia sp.), the melon fly (Trianea intermedia), the sorrel cutworm (Viminia rumicis), (Dacus cucurbitae), the oriental fruit fly (Dacus dorsalis), the the cutworm (Xestia c-nigrum); citrus fruit fly (Dacus tsuneonis), the Japanese cherry fruit fly 0065 the following of the beetle order (COLEOPTERA): (Rhacochlaena japonica), the rice leaf miner (Hydrellia brown chafer (Adoretus tenuimaculatus), the cupreous chafer griseola), the rice whorl maggot (Hydrelia Sasakii), the (Anomala cuprea), the Soybean beetle (Anomala rufocuprea), cherry drosophila (Drosophila Suzuki), the rice stem maggot the flower beetle (Eucetonia pilifera), the aohanamuguri (Ce (Chlorops Oryzae), the wheat stem maggot (Meromyza tonia roelofsi), the yellowish elongate chafer (Heptophylla nigriventris), the Japanese rice leafminer (Agromyza Oryzae), picea), the Japanese cockchafer (Melolontha japonica), the the pea leaf miner (Chromatomyia horticola), the celery scarab beetle (Mimela splendens), the citrus flower chafer miner fly (Liriomyza bryoniae), the Stone leek leafminer (Li (Oxycetonia jucunda), the Japanese beetle (Popillia riomyza chinensis), the American serpentine leafminer (Liri japonica), the varied carpet beetle (Anthrenus verbasci), the omyza trifolii), the vegetable leafminer (Liriomyza sativae), black carpet beetle (Attagenus unicolor japonicus), the ciga the pea leafminer (Liriomyza huidobrensis), the onion fly rette beetle (Lasioderma serricorne), the powderpost beetle (Delia antiqua), the bean seed fly (Delia platura), the beet (Lyctus brunneus), the corn Sap beetle (Carpophilus dimid leaf miner (Pegomya cunicularia), the house fly (Musca iatus), the dried fruit beetle (Carpophilus hemipterus), the domestica), the blowfly (Phormia regina), the house-gnat leaf feeding ladybird (Epilachna vigintioctomaculata), the (Culex pipiens pallens Coquillett), the chikaieka (Culex pipi phytophagous ladybird beetle (Epilachna vigintioctopunc ens molestus Forskal), the shina-hamadaraka (Anopheles tata), the black fungus beetle (Alphitobius laevigatus), the (Anopheles) sinensis Wiedemann), and the Asian tiger mos yellow-dappled longicorn (Neatus picipes), the Smalleyed quito (Aedes albopictus (Skuse)). flour beetle (Palorus ratzeburgii), the depressed flour beetle 0068. In addition, examples that may be given of stored (Palorus subdepressus), the yellow mealworm (Tenebrio grain insects that may be controlled by the invention include, molitor), the red flour beetle (Tribolium castaneum), the con the but are not limited to, the following: the redlegged ham US 2010/007 1096 A1 Mar. 18, 2010

beetle (Necrobia rufipes), the soybean beetle (Callosobru 0070 The following may be given as examples of the chus analis), the redshoulderedham beetle (Necrobia ruficol fungicidal compound included in the pest control composi lis), the Pineapple beetle (Urophorus humeralis), the Ameri tion of the invention, but it should be noted that the invention can spider beetle (Mezium americanum), the stored nut moth is not limited thereto. (Parallipsagularis), the bean weevil (Acanthoscelides Obtec 0071. The examples include: carboxamide fungicides, tus), the pea weevil (Bruchus pisorum), the Australian spider Such as thifluZamide, flutolanil, mepronil, pencycuron, beetle (Ptinus tectus), the larger grain borer (Prostephanus ethaboxam, oxycarboxin, carboxin, and silthiofam; truncatus), the broad-horned flour beetle (Gnathocerus cor 0072 melanin biosynthesis inhibitor fungicides, such as nutus), the merchant grain beetle (Oryzaephilus mercator), carpropamid, diclocymet, tricyclazole, pyroquilon, fenoxa nil, and fthalide; the meal moth (Pyralis farinalis), the Kashmir flour beetle 0073 strobilurin fungicides, such as azoxystrobin, (Tribolium freemani), the foreign grain beetle (Ahasverus metominostrobin, orysastrobin, kresoxim-methyl, fluoxas advena), the lesser meal worm (Alphitobius diaperinus), the trobin, trifloxystrobin, dimoxystrobin, pyraclostrobin, and rice moth (Corcyra cephalonica), the golden spider beetle picoxystrobin; (Niptus holoeucus), the granary weevil (Sitophilus grana 0074 antibiotics, such as kasugamycin, validamycin, ben ries), the black flour beetle (Tribolium madens), the destruc Zylaminobenzenesulfonic acid salt of blasticidin-S, teclofta tive flour beetle (Tribolium destructor), the Nemapogon lam, oxytetracycline, Streptomycin, blasticidin-S, mildiomy (Nemapogon granella), the maize weevil (Sitophilus zea cin, and polyoxins; mais), the broadnosed grain weevil (Caulophilus Oryzae), the 0075 pyrimidine fungicides, such as ferimzone, fenari cadelle beetle (Tenebroides mauritanicus), the grain worm mol, pyrifenox, nuarimol, and bupirimate; (Martyringa xeraula), the longheaded flour beetle (Latheti 0076 azole fungicides, such assimeconazole, furametpyr. cus oryzae), the slenderhorned flour beetle (Gnathocerus ipconazole, triflumizole, prochloraz, pefurazoate, imazalil, maxillosus), the lesser grain borer (Rhizopertha dominica), imibenconazole, etridiazole, epoxiconazole, fumaric acid salt the mould beetle (Aridius modifer), the sap beetle (Carpophi of Oxpoconazole, diniconazole, difenoconazole, cyprocona lus pilosellus), the dark mealworm (Tenebrio obscurus), the Zole, tetraconazole, tebuconazole, triadimenol, triadimefon, black rice worm (Aglossa dimidiata), the rusty grain beetle triticonazole, bitertanol, fenbuconazole, fluguinconazole, (Cryptolestes ferrugineus), the drugstore beetle (Stegobium flusilaZole, flutriafol, prothioconazole, propiconazole, bro paniceum), the almond moth (Ephestia cautella), the broad muconazole, hexaconazole, penconazole, metconazole, and bean weevil (Bruchus rufimanus), the square-necked grain fluquinconazole; beetle (Cathartus quadricollis), the hairy fungus beetle 0077 copper fungicides, such as copper, copper non (Tiphaea Stercorea), the tsuyahimemakimusshi (Holopar ylphenolsulfonate, basic copper oxychloride, basic copper amecus signatus), the seed beetle (Pagiocerus frontalis), the sulphate, oxine copper, DBEDC, anhydrous copper sulfate, niseduriyakesikisui (Carpophilus delkeskampi), the spider and copper II hydroxide; 0078 benzimidazole fungicides, such as thiophanate-me beetle (Gibbium aequinoctiale), the sawtoothed grain beetle thylbenomyl, thiabendazole, thiophanate, carbendazim, and (Oryzaephilus Surinamensis), the Indian-meal moth (Plodia fuberidazole; interpunctella), the hide beetle (Dermestes maculates), the 0079 organophosphorus fungicides, such as EDDP, IBP, cowpea weevil (Callosobruchus phaseori), the rusty grain tolclofoS-methyl, fosetyl, dinocap, and pyrazophos; beetle (Cryptolestes pusilloides), the angoumois grain moth 0080 acylalanine fungicides, such as metalaxyl, oxadixyl, (Sitotroga cerealella), the khaprabeetle (Trogoderma grana benalaxyl, and metalaxyl-M; dicarboximide fungicides, such rium), the brown spider beetle (Ptinus clavipes), the larger as iprodione, procymidone, VincloZolin, and chloZolinate; cabinet beetle (Trogoderma inclusium), the lentil pest (Bru I0081 dithiocarbamate fungicides, such as thiuram, man chus lentis), a the futagomameZoumushi (Callosobruchus coZeb, propineb, Zineb, metiram, maneb, Ziram, and subinnotatus), the Mexican bean weevil (Zabrotes subfascia amobam; tus), the vetch bruchid (Bruchus brachialis), the Siamese I0082 soil disinfectants, such as hydroxyisoxazol (hymex grain beetle (Lophocaterus pusillus), the munabirohimeha aZol), methasulfocarb, chloropicrin, flusulfamide, dazomet, makimushi (Dienerella costulata), the Mexican grain beetle methylisothiocyanate, potassium salt of hydroxyisoxazol. (Pharaxonotha kirschii), the peanut bruchid (Carvedon ser etridiazole, 1,3-dichloropropene, and carbam; ratus), the cowpea bruchid (Callosobruchus maculatus), the I0083 organochlorine fungicides, such as TPN and captan; checkered beetle (Necrobia violacea), the rhodesian bean 0084 anilino pyrimidine fungicides, such as mepanipy weevil (Callosobruchus rhodesianus) and the coffee bean rim, cyprodinil, and pyrimethanil; weevil (Araecerus fasciculatus). I0085 natural products, such as rapeseed oil and machine 0069. Examples that may be given of timber pest insects oil; that may be controlled by the invention include, but are not I0086 inorganic fungicides, such as sulfur, lime sulfur limited to the following: the nisima-kikuimushi (Sueus niisi mixture, Zinc sulfate, fentin, sodium hydrogencarbonate, mai), the coffee-kikuimushi (Taphronychus coffeae), the potassium hydrogencarbonate, and hypochlorite; sazankakoatomaru-kikuimushi (Poecilips Oblongus), the I0087 morpholine fungicides, such as dimethomorph, fen black twig borer (Xylosandrus compactus), the mulberrybark propidin, fempropimorph, spiroxamine, tridemorph, dode beetle (Xvleborus atratus), the futairo-kikuimushi (Xyle morph, and flumorph; borus bicolor), the akagashinoki-kikuimushi (Xvleborus cin I0088 fungicides, such as iprovalicarb, imazalil-S, imi cisus), redbay ambrosia beetle (Xvleborus glabratus), the noctadine albesilate, quinoxyfen, chinomethionat, metallic aino-kikuimushi (Xvleborus interjectus), camphor shot borer silver, chlorothalonil, chloroneb, cyazofamid, diethofencarb, (Xvlosandrus mutilatus) and the todomatsuoo-kikuimushi dichlofluanid, dichloram, dithianon, diflumetorim, dimethiri (Xvleborus validus). mol, cymoxanil, silthiofam, Spiroxamine, Zoxamide, thiadi US 2010/007 1096 A1 Mar. 18, 2010

azine (minleb), dodine, triforine, tolylfluanid, nitrothal-iso sesame seeds, Sunflower seeds, oilseed rape, safflower seeds, propyl, famoxadone, fenamidone, fenitropan, fenpiclonil. and cotton seeds), nuts (such as almond, ginkgo nut, chestnut, fenhexamid, folpet, fluaZinam, fluopicolide, fluoroimide, walnut, and pecan), cacao bean, coffee bean, tea, and hops. propamocarb, propamocarb hydrochloride, propylene glycol 0092 Silage refers to feed and the like that is stored and fatty acid esters, calcium salt of prohexadione, benthiazole, saved for domestic distribution or export/import, and is gen benthiavalicarb-isopropyl, myclobutanil, organic nickel, res erally provided for the breeding of livestock and the like. Veratrol, diclomeZine, iminoctadine acetate, isoprothiolane, Specific examples that may be given thereof include cereals, tiadinil, probenazole, acibenzolar-S-methyl, fludioxonil, fos legumes, and the like. etyl-aluminum, guaZatine and triaZOxide. 0093 Stored flowering plants refers to potted plants, 0089. In the invention, a plant seed refers to something that flower arrangements, cut flowers, bulbs, seeds, and the like stores nutrients for seedlings to sprout and is used for propa stocked for domestic distribution or export/import, and are gation in agriculture. Specific examples that may be given mainly provided for decoration and cultivation. Examples include, but are not limited to: seeds, such as of corn, Coix that may be given thereof include, orchid, Rumohra, chrysan lacrymajoli (Job's Tears), Japanese millet, buckwheat, Soya themum, Xerophyllum, japonica, lily, , wild bean, azuki bean, common bean, pea, broad bean, peanut, pink, rose, anthurium, carnation, tulip and the like. hyacinth bean, cabbage, Brussels sprout, Japanese radish, 0094 Export/import timber refers to logs or sawn timbers nonhead-forming brassica leaf vegetables, cotton, rice, Sugar that are stored/stockpiled for the purpose of export/import, beet, table beet, wheat, barley, sunflower, tomato, cherry and is generally provided for processing, construction, and tomato, chilli peppers, cucumber, watermelon, bitter melon, the like. Examples that may be given thereof include hem melon, oriental pickling melon, winter melon, eggplant, spin lock, Douglas fir, spruce, Picea jezoensis, Abies Sachalinen ach, podded pea, green bean, immature broad bean, green sis, larch, lauan, and the like. pea, asparagus, okra, garland chrysanthemum, carrot, pars 0.095 The content of the dinotefuran as an active ingredi ley, Welsh onion, scallion, lettuce, nonhead-forming lettuces, ent of the composition of the invention is normally in the Japanese pumpkin, Sugarcane, tobacco, Sweet pepper, rape, range of 0.005% to 99% with respect to the total weight of the rye, and oats; seed tubers, such as taro, potato, Sweet potato, composition, preferably is 0.01% to 90%, and is still more yam and konnyaku; bulbs, such as edible lily, tulip, narcissus, preferably 0.1% to 85%. On the other hand, the content of the hyacinth, amaryllis, lily, gladiolus and ; and seed bulbs, fungicidal compound is normally in the range of 0.005% to Such as shallot, ginger, garlic and lotus root. Moreover, the 99% with respect to the total weight of the composition, pest insect damage control by application to these plant seeds preferably is 0.01% to 90%, and still more preferably is 0.1% and plant bodies is not only related to these seeds, seed tubers, to 85%. The total content of dinotefuran together with other and seed bulbs themselves, but also to the products such as fungicidal compound(s) is normally in the range of 0.005% to stems, leaves, fruits and the like that grow therefrom. 99% with respect to the total weight of the composition, 0090 The plant seeds and plant bodies in this specification preferably is 0.01% to 90%, and is still more preferably 0.1% may also be plant seeds, cereals, legumes, vegetables, and to 85%. flowering plants which have undergone genetic transforma 0096. A carrier used for the above formulation is not par tion, in other words, plants that do not initially exist in nature ticularly limited, and if it is a carrier that is usually used for but are produced by manipulating genes and the like artifi agricultural formulation, then either a Solid or a liquid carrier cially. Examples thereof include, but are not limited to: plants may be used. As a solid carrier, the following may be given as imparted with herbicide resistance Such as Soya bean, corn, examples: inorganic Substances, such as bentonite, montmo and cotton; cold adapted plants such as rice and tobacco; and rillonite, kaolinite, diatomaceous earth, white clay, talc, clay, plants imparted with the functionality of producing insecti Vermiculite, gypsum, calcium carbonate, amorphous silica, cidal Substance, such as corn, cotton, and potato. ammonium sulfate; vegetable organic Substance, such as Soya 0091 Stored cereals, stored legumes, stored fruits, and bean flour, wood flour, saw dust, wheat flour, lactose, Sucrose, stored vegetables refer to cereals, legumes, fruits, vegetables, and glucose; and urea and the like. As a liquid carrier, the and the like which are stored and saved for domestic distri following may be given as examples: aromatic hydrocarbons bution or export/import, and these are generally provided for Such as toluene, Xylene, and cumene, and naphthenes; paraf consumption or processing. Examples that may be given fin hydrocarbons, such as n-paraffin, iso-paraffin, liquid par thereof include, rice, barley, wheat, corn, rye, oat, pea, kidney affin, kerosene, mineral oil, and polybutene; ketones, such as bean, black-eyed bean, Saltani bean, Saltapia bean, butter acetone, and methyl ethyl ketone; ethers, such as dioxane and bean, pegia bean, white bean, lima bean, broad bean, Soya diethylene glycol dimethyl ether, alcohols, such as ethanol, bean, azuki bean, apricot, Japanese plum, cherry, plum, nec propanol, and ethylene glycol, carbonates, such as ethylene tarine, peach, orange, grapefruit, Chinese citron, lime, lemon, carbonate, propylene carbonate, and butylene carbonate; loquat, quince, apple, avocado, kiwifruit, guava, date, pine aprotic solvents such as dimethylformamide, and dimethyl apple, passion fruit, banana, papaya, mango, Strawberry, sulfoxide; and water, and the like. cranberry, huckleberry, blackberry, blueberry, persimmon, 0097. Furthermore, in order to reinforce the effect of the watermelon, grape, oriental melon, melon, turnip, cauli invention compound the following adjuvants (binders, disin flower, cabbage, watercress, kale, horseradish, radish, broc tegrators, pH adjusters, antifoams and antifreezing agents) coli, Sweet potato, konnyaku tubers, taro, potato, Japanese may also be used, alone or in combinations thereof, according pumpkin, cucumber, oriental pickling melon, artichoke, to the purpose and in consideration of the form of the formu endive, burdock, Salsify, chicory, lettuce, Shiitake mushroom, lation, the treatment method and the like. As adjuvants, Sur mushroom, celery, carrot, parsnip, parsley, tomato, Sweet factants may be used that are usually used in agricultural pepper, asparagus, onion, garlic, Welsh onion, Scallion, green formulation for purposes Such as emulsification, dispersion, Soya bean, okra, Sugar cane, ginger, Sugar beet, spinach, spreading, and wetting, and examples that may be given of immature kidney beans, immature peas, oilseeds (such as Such surfactants include, but are not limited to: nonionic US 2010/007 1096 A1 Mar. 18, 2010

Surfactants such as Sorbitan fatty acid esters, polyoxyethylene 0102 AS required, silicone compounds may be used as Sorbitan fatty acid esters, Sucrose fatty acid esters, polyoxy antifoaming agents and propylene glycol, ethylene glycol, ethylene fatty acid esters, polyoxyethylene resin acid esters, and the like may be used as antifreezing agents. polyoxyethylene fatty acid diesters, polyoxyethylene castor 0103) When applying the composition of the invention to oils, polyoxyethylene alkyl ethers, polyoxyethylene alkyl plant seeds, plant seeds may be immersed in a composition as phenyl ethers, polyoxyethylene dialkyl phenyl ethers, form it is. Alternatively, the composition may be diluted to a Suit aldehyde condensates of polyoxyethylene alkyl phenyl ether, able concentration with a suitable carrier, and then used by polyoxyethylene-polyoxypropylene block polymer, alkyl immersion, dust coating, spraying, coating treatment, or the polyoxyethylene-polyoxypropylene block polymer ether, like, to plant seeds. alkylphenyl polyoxyethylene-polyoxypropylene block poly 0104. There are no particular limitations to suitable carri mer ether, polyoxyethylene alkylamine, polyoxyethylene ers, and examples that may be given thereof include: liquid carriers, such as water or organic solvents such as ethanol: fatty acid amide, polyoxyethylene bisphenyl ether, polyoxy Solid carriers, such as inorganic Substances like bentonite, alkylene benzylphenyl ether, polyoxyalkylene styryl phenyl montmorillonite, kaolinite, diatomaceous earth, white clay, ether, polyoxyalkylene adducts of a higher alcohol, polyoxy talc, clay, Vermiculite, gypsum, calcium carbonate, amor ethylene ethers, ester modified silicones, and fluorosurfac phous silica, and ammonium sulfate; vegetable organic Sub tants; anionic Surfactants such as alkyl Sulfates, polyoxyeth stances. Such as Soya bean flour, wood flour, saw dust, wheat ylene diallyl ether sulfates, polyoxyethylene alkyl ether flour, lactose. Sucrose, and glucose; and urea. Sulfates, polyoxyethylene alkylphenyl ether Sulfates, poly 0105. The dilution rate of formulation may be set appro oxyethylene benzylphenyl ether sulfates, polyoxyethylene priately, and the dilution rate is suitably chosen according to styryl phenyl ether Sulfates, polyoxyethylene-polyoxypropy the candidate crop for application, type of disease damage, lene block polymer Sulfates, paraffin Sulfonates, alkane Sul and type of insect damage, and the dilution rate is Suitably 1 fonates, AOS, dialkyl sulfosuccinate, alkylbenzene sul to 50,000 times, is preferably 1 to 20,000 times, and is still fonates, naphthalene Sulfonates, dialkyl naphthalene more preferably 1 to 10,000 times. Sulfonates, formaldehyde condensates of naphthalene Sul 0106 For carrying out dust coating, spraying, and coating fonates, alkyl diphenyl ether disulfonates, lignin Sulfonates, treatment, a suitable amount of the formulation used is usu polyoxyethylene alkyl phenyl ether Sulfonates, polyoxyeth ally about 0.05% to 50% of dry plant seed weight, more ylene alkyl ether SulfoSuccinate half esters, fatty acid salts, preferably 0.1% to 40%, and still more preferably 0.1% to N-methyl fatty acid sarcosinate, resinates, polyoxyethylene 30%. However, the amount used is not limited to these ranges, alkyl ether phosphates, polyoxyethylene phenyl ether phos and may be varied according to the form of the formulation phates, polyoxyethylene dialkyl phenyl ether phosphates, and to the kind of plant seed used as the candidate for treat polyoxyethylene benzylated phenyl ether phosphates, poly ment. oxyethylene benzylated phenylphenyl ether phosphates, polyoxyethylene Styrylated phenyl ether phosphates, poly EXAMPLES oxyethylene benzylated phenylphenyl ether phosphates, polyoxyethylene-polyoxypropylene block polymer phos 0107 The invention will now be explained in detail, with phates, polyoxyethylene diallyl ether Sulfates, phosphatidyl reference to Examples and Test Examples. choline, phosphatidyl ethanolimine, alkyl phosphates and Sodium tripolyphosphates; polyanion type high molecular Example 1 surfactant derived from acrylic acid with acrylonitrile, acry Powder Formulation lamide-methylpropanesulfonic acid; cationic Surfactants, Such as alkyl trimethyl ammonium chloride, methyl polyoxy 0108) 1 part of dinotefuran, 10 parts of hymexazol, 88.5 ethylene alkyl ammonium chloride, alkyl N-methylpyri parts of clay, and 0.5 parts of DRILESS B (trade name, an dinium bromide, mono-methylated ammonium chloride, aggregating agent from Sankyo Co., Ltd.) were uniformly dialkyl methalated ammonium chloride, alkyl pentamethyl mixed together and ground, and a powder formulation con propylene amine dichloride, alkyl dimethyl benzalkonium taining dinotefuran at 1% and hymexazol at 10% was chloride, and benzethonium chloride; and amphoteric Surfac obtained. tants, such as dialkyl diaminoethyl betaines and alkyl dim ethylbenzyl betaine. Example 2 0098. As a binder, examples that may be given include Wettable Powder Sodium arginate, polyvinyl alcohols, gum arabic, sodium 0109 40 parts of dinotefuran, 4 parts of flusulfamide, 1 CMC, bentonite, and the like. part of sodium ligninsulfonate, 5 parts of white carbon, and 50 0099 Examples that may be given of disintegrants include parts of diatomaceous earth were mixed together and ground, Sodium CMC, crosscarmellose sodium, and examples of sta and a wettable powder containing dinotefuran at 40% and bilizers include hindered phenol based antioxidants, benzot flusulfamide at 4% was obtained. riazol based and hindered amine based ultraviolet absorbers, and the like. Example 3 0100 Phosphoric acid, acetic acid, and sodium hydroxide may be used as a pH adjuster, and industrial fungicides and Wettable Powder antifungal agents, such as 1,2-benzisothiazolin-3-one and the 0110 70 parts of dinotefuran, 4 parts of flusulfamide, 1 like, may be added for prevention of bacteria and molds. part of sodium ligninsulfonate, 5 parts of white carbon, and 20 0101. As a thickener, Xanthane gum, guar gum, Sodium parts of diatomaceous earth were mixed together and ground, CMC, gum arabic, polyvinyl alcohols, montmorillonite, and and a wettable powder containing dinotefuran at 70% and the like may also be used. flusulfamide at 4% was obtained. US 2010/007 1096 A1 Mar. 18, 2010

Example 4 Example 7 Wettable Powder Granular Wettable Powder 0111 70 parts of dinotefuran, 4 parts of hymexazol, 1 part 0118 20 parts of dinotefuran, 50 parts of benomyl, 3 parts of sodium ligninsulfonate, 5 parts of white carbon, and 20 of sodium CMC, 5 parts of sodium alkylsulfate, and 22 parts parts of diatomaceous earth were mixed together and ground, of clay were uniformly mixed, and then kneading with water, and a wettable powder containing dinotefuran at 70% and pelletization, drying, and particle size regulation were per hymexazol at 4% was obtained. formed thereto, and a granular wettable powder containing dinotefuran at 20% and benomyl at 50% was obtained. Example 5 Example 8 Wettable Powder Flowable 0112 70 parts of dinotefuran, 4 parts of flusulfamide, 4 parts of hymexaZol. 1 part of Sodium ligninsulfonate, 5 parts 0119 Wet grinding was performed using a sandgrinder on of white carbon, and 16 parts of diatomaceous earth were 20 parts of dinotefuran, 4 parts of flusulfamide, 5 parts of mixed together and ground, and a wettable powder containing propylene glycol, 5 parts of polyoxyethylene oleate, 5 parts of dinotefuran at 70%, flusulfamide at 4% and hymexazol at 4% polyoxyethylene diallyl ether sulfate, 0.2 parts of silicone was obtained. antifoaming agent, and 60.8 parts of water, and a flowable containing dinotefuran at 20% and flusulfamide at 4% was Reference Example 1 obtained. Wettable Powder Example 9 0113 70 parts of dinotefuran, 1 part of sodium ligninsul fonate, 5 parts of white carbon, and 24 parts of diatomaceous Flowable earth were mixed together and ground, and a wettable powder 0120 Wet grinding was performed using a Sandgrinder on containing dinotefuran at 70% was obtained. 20 parts of dinotefuran, 4 parts of hymexazol, 5 parts of propylene glycol, 5 parts of polyoxyethylene oleate, 5 parts of Reference Example 2 polyoxyethylene diallyl ether sulfate, 0.2 parts of silicone antifoaming agent, and 60.8 parts of water, and a flowable Wettable Powder containing dinotefuran at 20% and hymexazol at 4% was 0114. 4 parts of flusulfamide, 1 part of sodium ligninsul obtained. fonate, 5 parts of white carbon, and 90 parts of diatomaceous earth were mixed together and ground, and a wettable powder Reference Example 5 containing flusulfamide at 4% was obtained. Flowable Reference Example 3 0121 Wet grinding was performed using a Sandgrinder on 20 parts of dinotefuran, 5 parts of propylene glycol, 5 parts of Wettable Powder polyoxyethylene oleate, 5 parts of polyoxyethylene diallyl 0115 4 parts of hymexazol, 1 part of sodium ligninsul ether Sulfate, 0.2 parts of silicone antifoaming agent, and 64.8 fonate, 5 parts of white carbon, and 90 parts of diatomaceous parts of water, and a flowable containing dinotefuran at 20% earth were mixed together and ground, and a wettable powder was obtained. containing hymexazol at 4% was obtained. Reference Example 6 Reference Example 4 Flowable Wettable Powder 0.122 Wet grinding was performed using a Sandgrinder on 0116 4 parts of flusulfamide, 4 parts of hymexazol, 1 part 4 parts of flusulfamide, 5 parts of propylene glycol, 5 parts of of sodium ligninsulfonate, 5 parts of white carbon, and 88 polyoxyethylene oleate, 5 parts of polyoxyethylene diallyl parts of diatomaceous earth were mixed together and ground, ether Sulfate, 0.2 parts of silicone antifoaming agent, and 80.8 and a wettable powder containing flusulfamide at 4% and parts of water, and a flowable containing flusulfamide at 4% hymexazol at 4% was obtained. was obtained. Example 6 Reference Example 7 Emulsion Flowable 0117 15 parts of dinotefuran, 15 parts of triflumizole, 10 0123 Wet grinding was performed using a Sandgrinder on parts of cyclohexane, 40 parts of Xylene, and 20 parts of 4 parts of hymexaZol, 5 parts of propylene glycol, 5 parts of SORPOL (trade name, a surfactant made by Toho Chemical polyoxyethylene oleate, 5 parts of polyoxyethylene diallyl Industries Co., Ltd.) were uniformly dissolved and mixed, ether Sulfate, 0.2 parts of silicone antifoaming agent, and 80.8 and an emulsion containing dinotefuran at 15% and triflumi parts of water, and a flowable containing hymexazol at 4% Zole at 15% was obtained. was obtained. US 2010/007 1096 A1 Mar. 18, 2010

Test Example 1 Test Example 2 Control Effect Against Sugar Beet Seedling Damp ing Off Control Effect Against Common Scab and Black Scarf in Potato 0.124 A Rhizoctonia culture and a Pythium culture were separately cultivated at 25°C. for seven days in a wheat bran 0129. A Rhizoctonia culture was cultivated in a concrete medium, and after respectively grinding, the Rhizoctonia cul pot in a wheat bran medium at 25°C. for seven days, and this ture and/or the Pythium culture were added to and mixed in was then added at 0.1% by weight with respect to steam with sterilized soil, and the mixtures were filled in plastic pots to obtain infected soils each containing: sterilized soil and mixed in uniformly. A Rhizoctonia culture 0.125 Rhizoctonia culture at 0.1% with respect to the ster cultivated by the same method was added at 0.1% with ilized soil; respect to soil extracted from a common scab infected field 0126 Pythium culture at 0.1% with respect to the steril and mixed in uniformly, and soil was also extracted from a ized soil, and common scab infected field. These three soil compositions 0127 Rhizoctonia culture at 0.1% and Pythium culture at were placed, respectively, into concrete pots (50 cm lengthx 0.1%, with respect to the sterilized soil. 50 cm width:X30 cm depth) and the test soils were thereby 0128 Subsequently, amounts of 3.5% and 7% per kg of obtained. seed of the powder of Example 1 containing active ingredi 0.130 Next, after carrying out dip treatment of the seed ents of dinotefuran and hymexazol, and amounts of 0.5% and tubers of potato (variety: Baron) into, respectively, 50 times 1.0% per kg of seed of a commercially available seed fungi diluents of the wettable powderproduced in Example 2 and in cide (TACHIGAREN, a dust coating agent containing Reference Example 2 (comparative agents), and of a com hymexazol made by Sankyo Agro Co., Ltd.) were added to mercial fungicide (NOTTOBAN, a wettable powder contain sugar beet seed (variety: ABEND), and well mixed. The sugar ing tolclofos-methyl and flusulfamide, made by Sumitomo beet seeds to which chemical treatment had been carried out Chemical Co., Ltd.), the seed tubers were air dried and then were sown at five seeds per pot, with a total of 20 pots, and these pots were grown on in a greenhouse. The number of two seed tubers were buried per pot. For the non-treated non-sprouting seeds was examined at 7 days after Sowing, and category, seed tubers that had not undergone chemical treat the seedling dieback number was examined at 14 days after ment were buried. 110 days afterburying the seed tubers, the Sowing, with the naked eye, and the seedling dieback rate was newly formed potatoes were dug up, and the existence of computed by the following Formula 1. Moreover, the exist disease onset was examined with the naked eye, and the ence or not of occurrences of phytotoxicity was also exam disease onset potato ratio was computed by the following ined with the naked eye. Results are shown in Table 1. Formula 2. Five replicates of the above test were performed, and the average values of the results are shown in Table 2. Seedling dieback rate ((number of non-sprouting seeds--seedling dieback number), number of seeds Disease onset potato ratio=(number of potatoes with sown)x100 Formula 1: disease onset/total number of potatoes examined)x100 Formula 2:

TABLE 1 Seedling dieback Seedling dieback Seedling dieback rate with Active ingredient rate with rate with Rhizoctonia and Test compound amount (g/kg seed) Rhizoctonia (%) Pythium (%) Pythium (%) Phytotoxicity Powder Dinotefuran 0.7+ SO.6 O.9 42.2 None formulation of Hymexazol 7.0 the invention Dinotefuran 0.35 + S3.6 4.1 48.8 None (Example 1) Hymexazol 3.5 Control seed 7.0 65.8 1.1 59.1 None disinfectant 3.5 63.9 4.3 58.6 None TACHIGAREN powder formulation No treatment 65.3 SO4 57.5 US 2010/007 1096 A1 Mar. 18, 2010 11

TABLE 2

Disease onset Disease onset Disease onset potato ratio in soil potato ratio in soil potato ratio in soil infected with black Dilution infected with black infected with common Scarf and common Test compound rate scarf (%) scab (%) scab (%) Phytotoxicity Wettable powder 50 times 2O.S 18.6 18.4 None of the invention (Example 2) Comparative 50 times 28.2 25.3 26.2 None wettable powder (Reference Example 2) Control 50 times 1.3 27.2 28.3 None chemical NOTTOBAN wettable powder No treatment 25.2 50.5 63.1

Test Example 3 tant (BENLATE, trade name, a wettable powder containing benomyl as the active ingredient made by Sumitomo Chemi Control Effect Against Bakanae Disease cal Co., Ltd.) as a control chemical, and a dressing treatment 0131 Rice seeds (variety: Tanginbozu-dwarf) infected was carried out. After soaking the seeds (at 15° C. for three with benomyl-resistant Bakanae disease was mixed respec days) and forced sprouting (at 28°C. for one day), the seeds tively with the emulsion produced in Example 6 containing to which chemical treatment had been carried out were each dinotefuran and triflumizole as active ingredients, and mixed Sown at 100 seeds per plastic pot, and grown on in a green with a commercially available seed disinfectant (TRIFMIN, house. The existence of disease onset was examined for all the trade name, a wettable powder containing triflumizole made seedlings with the naked eye at 20 days after Sowing, and the by Nippon Soda Co., Ltd.) as a control chemical, and a dress disease onset seedling ratio was computed by the following ing treatment was carried out. After soaking the seeds (at 15° Formula 4. Moreover, the existence or not of occurrences of C. for three days) and forced sprouting (at 28°C. for one day), phytotoxicity was also examined with the naked eye. Three the seeds to which chemical treatment had been carried out replicates of the above test were performed, and the average were each sown at 100 seeds per plastic pot, and grown on in values of the results are shown in Table 4. a greenhouse. The existence of disease onset was examined Disease onset seedling ratio=(number of diseased for all the seedlings with the naked eye at 20 days after seedlings/number of seeds sown)x100 Formula 4: Sowing, and the disease onset seedling ratio was computed by the following Formula 3. Moreover, the existence or not of occurrences of phytotoxicity was also examined with the TABLE 4 naked eye. Three replicates of the above test were performed, Disease and the average values of the results are shown in Table 3. Active ingredient OnSet amount seedling Disease onset seedling ratio=(number of diseased Test compound (g/kg seed) ratio (%) Phytotoxicity seedlings/number of seeds sown)x100 Formula 3: Granular wettable powder Dinotefuran 2.0 + 29.4 None of the invention Benomyl 5.0 TABLE 3 (Example 7) Control seed disinfectant Benomyl 5.0 39.7 None Active ingredient Disease onset BENLATE wettable amount Seedling ratio powder Test compound (g/kg seed) (%) Phytotoxicity No treatment 45.3 Emulsion of the Dinotefuran 5.0 + 32.4 None invention Trifumizole 5.0 (Example 6) Control seed Trifumizole 5.0 41.5 None Test Example 5 disinfectant TRIFMIN emulsion Control Effect Against Beet Flea Beetle on Sugar No treatment 45.3 Beet 0.133 Processing was carried out in a seed dressing machine (chemical liquid jetting within a rotating drum) Test Example 4 using the wettable powders produced in Example 3, Example Control Effect Against Bakanae Disease in Rice 4. Example 5. Reference Example 1 (comparative agent), Reference Example 2 (comparative agent), Reference 0132) Rice seeds (variety: Tanginbozu-dwarf) contami Example 3 (comparative agent) and Reference Example 4 nated with benomyl-resistant Bakanae disease was mixed (comparative agent), and with Gaucho (trade name, an insec respectively with the granular wettable powder produced in ticide containing imidacloprid made by Bayer CropScience), Example 7 containing dinotefuran and benomyl as active at the following amounts of formulation per 100,000 seed unit ingredients, and with a commercially available seed disinfec of Sugar beet seed. US 2010/007 1096 A1 Mar. 18, 2010

0134 Wettable powder: 65g and 130g of formulation/unit (one unit is 100,000 of sugar beet seeds). TABLE 5-continued 0135 Gaucho (imidacloprid): 130 g formulation/unit. Formulation treatment Prevention 0136. On the next day of treatment, the test seeds were amount index sown at 50 seeds each, in a concrete pot filled with soil (5 m Test compound (g/unit) (%) Phytotoxicity lengthx2 m width:X60 cm depth). Comparative 65g O None 0.137 The level of insect damage by striped fleabeetle was wettable powder 130 g O None investigated at 45 days after Sowing and at 60 days after (Reference Sowing, and the prevention index was computed by the fol Example 2) lowing formula 5. Moreover, the existence or not of occur Comparative 65g O None rences of phytotoxicity was also examined with the naked wettable powder 130 g O None (Reference eye. Example 3) 0138 Results are shown in Table 5. Comparative 65g O None 0.139. The index number levels of insect damage are as wettable powder 130 g O None follows. (Reference Example 4) 0140 Index 0: No insect damage Control 130 g 85 None 0141 Index 1: Slight level of insect damage insecticide 0142 Index 2: Medium level of insect damage Gaucho 0143 Index 3: High level of insect damage No treatment O None Prevention index=100-((1xnumber of insect damage at index 1+2xnumber of insect damage at index 2+3x Test Example 6 number of insect damage at index 3)f(3xtotal number of examinations)x100) Formula 5: Control Effect Against Adzuki Bean Weevil 0144 Coating treatment was carried out using the respec tive flowables produced in Example 8. Example 9, Reference TABLE 5 Example 5 (comparative agent), Reference Example 6 (com Formulation treatment Prevention parative agent), and Reference Example 7 (comparative amount index agent) at a dose of 5, 10 and 20 ml, with respect to 1 kg of Test compound (g/unit) (%) Phytotoxicity aZuki bean seed. After air-drying, portions thereof were Wettable powder 65g 100 None moved to 9 cm deep petri dishes, and allowed to stand in a of the invention 130 g 100 None constant 25° C. temperature room. Two months and three (Example 3) months after the coating treatment, respectively, five male Wettable powder 65g 100 None adult adzuki bean weevils and five adult female adzuki bean of the invention 130 g 100 None (Example 4) weeviles, ten in total, were grazed per deep petri dish. The Wettable powder 65g 100 None number of dead weevils and the number of eggs laid on the of the invention 130 g 100 None aZuki beans were examined two days after grazing, and the (Example 5) mortality was computed by the following Formula 6. Five Comparative 65g 88 None wettable powder 130 g 92 None replicates of the above test were performed, and the average (Reference values of the results are shown in Table 6. Example 1) Mortality=(number of dead weevils in treated cat egory/50 weevils)x100 Formula 6:

TABLE 6

Two months after Three months after Active ingredient treatinent treatinent Test Amount Mortality Number of eggs Mortality Number of eggs compound (g/kg seed) % laid female % laid female Flowable of Dinotefuran 1.0 + 100 O.OO 1OO O.OO the invention Fusulfamide 0.2 (Example 8) Dinotefuran 2.0 + 100 O.OO 1OO O.OO Fusulfamide 0.4 Dinotefuran 4.0 + 100 O.OO 1OO O.OO Fusulfamide 0.8 Flowable of Dinotefuran 1.0 + 100 O.OO 1OO O.OO the invention Hymexazol 0.2 (Example 9) Dinotefuran 2.0 + 100 O.OO 1OO O.OO Hymexazol 0.4 Dinotefuran 4.0 + 100 O.OO 1OO O.OO Hymexazol 0.8 Comparative Dinotefuran 1.0 95 O.O6 93 O.10 Flowable Dinotefuran 2.0 98 O.O2 94 O.08 (Reference Dinotefuran 4.0 100 O.OO 1OO O.OO Example 5) Comparative Flusulfamide 0.2 O 11.3 O 12.2 Flowable Fusulfamide 0.4 O 12.9 O 11.9 US 2010/007 1096 A1 Mar. 18, 2010 13

TABLE 6-continued

Two months after Three months after Active ingredient treatinent treatinent Test Amount Mortality Number of eggs Mortality Number of eggs compound (g/kg seed) % laid female % laid female (Reference Flusulfamide 0.8 O 12.4 O 10.4 Example 6) Comparative Hymexazol 0.2 O 12.3 O 10.9 Flowable Hymexazol 0.4 O 12.1 O 12.O (Reference Hymexazol 0.8 O 11.0 O 11.O Example 7) No treatment — O 11.5 O 10.8

Test Example 7 1. A plant disease and insect damage control composition comprising active ingredients of (RS)-1-methyl-2-nitro-3- Control Effect Against Striped Flea Beetle (tetrahydro-3-furylmethyl)guanidine (common name: 0145 Soil surfaces were treated with commercially avail dinotefuran) and at least one fungicidal compound selected able formulations at amounts of: from the group consisting of 2,4-dichloro-C.C.C.-trifluoro-4'- 0146 STARKLE granule (trade name, a granular formu lation containing 1% dinotefuran made by Sankyo Agro Co., nitro-m-toluenesulfonanilide (common name: flusulfamide), Ltd.) at 9 kg/10a; 3-hydroxy-5-methylisoxazol (common name: hymexaZol), 0147 NEBIJIN powder (trade name, a powder formula and (RS)-2-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3- tion containing 0.3% flusulfamide made by Sankyo Agro Co., (trimethylsilyl)propan-2-ol (common name: Simeconazole). Ltd.) at 30 kg/10 a. 2. The plant disease and insect damage control composi 014.8 MONGARIT granule (trade name, a granular for tion according to claim 1, wherein the at least one fungicidal mulation containing 1.5% simeconazole made by Sankyo compound comprises 2,4-dichloro-C.C.C.-trifluoro-4'-nitro Agro Co., Ltd.) at 6 kg/10a; m-toluenesulfonanilide (common name: flusulfamide). 0149 STARKLE granule and NEBUIN powder at 9 kg and 30 kg/10a; and 3. The plant disease and insect damage control composi 0150 STARKLE granule and MONGARIT granule at 9 tion according to claim 1, wherein the at least one fungicidal kg and 6 kg/10 a, respectively, and the treated soils were compound comprises 3-hydroxy-5-methylisoxazol (common lightly mixed with a rake. name: hymexaZol). 0151. Immediately after the soil treatment, Japanese rad 4. The plant disease and insect damage control composi ish seeds were sown in lines. The Japanese radishes were dug tion according to claim 1, wherein the at least one fungicidal up at 32 days and at 52 days after sowing, respectively, and the compound comprises (RS)-2-(4-fluorophenyl)-1-(1H-1,2,4- damage level to the roots was examined on the following triazol-1-yl)-3-(trimethylsilyl)propan-2-ol (common name: basis, and the degree of damage was computed from the simeconazole). following formula. Results are shown in Table 7. 0152 Damage Level 5. The plant disease and insect damage control composi 0153 A: Damage area is greater than 11% of the surface tion according to claim 1, wherein the at least one fungicidal area of root compound comprises a mixed composition of at least two 0154 B: Damage area is 5 to 10% of the surface area of selected from the group consisting of flusulfamide, hymex rOOt aZol, and Simeconazole. 0155 C: Damage area is 2 to 4% of the surface area of root 6. A plant disease and insect damage prevention method 0156 D: Damage area is 1% of the surface area of root comprising applying the pest control composition according Degree of damage=(number of roots of Ax4+number claim 1 to a plant body, Soil, plant seed, stored cereal, stored of roots of Bx330 number of roots of Cx2+number of legume, stored fruit, stored vegetable, silage, stored flowering roots of Dx1+number of roots with no damagex0), plant, or export/import timber. (number of roots examinedx4)x100 Formula 7: 7. The plant disease and insect damage prevention method according to claim 6, wherein the method of application to TABLE 7 plant seeds is spray treatment, coating treatment, dip treat ment, or dressing treatment of seeds. 52 days 32 days after after 8. The plant disease and insect damage prevention method Test chemicals Formulation amount treatinent treatinent according to claim 6, wherein the method of application to a stored cereal, stored legume, stored fruit, stored vegetable, STARKLE granule 9 kg/10 a 30 2O silage, stored flowering plants, or export/import timber is STARKLE granule + 9 kg/10 a + 2O 13 NEBIJIN powder 30 kg/10 a spray treatment, coating treatment, dip treatment, dressing NEBIJIN powder 30 kg/10 a 65 8O treatment, fumigation treatment, Smoke treatment, or pres STARKLE granule + 9 kg/10 a + 18 13 Sure injection. MONGARIT granule 6 kg/10 a MONGARIT granule 6 kg/10 a 65 88 9. Plant seed, stored cereal, stored legume, stored fruit, No treatment 60 70 stored vegetable, silage, stored flowering plant, or export/ import timber to which the plant disease and insect damage control composition according to claim 1 has been applied. US 2010/007 1096 A1 Mar. 18, 2010 14

10. The plant disease and insect damage prevention method 11. A method of preventing plant disease and insect dam according to claim 6, wherein the method of application to a age to a plant body grown from a plant seed, the method plant body or soil is foliar application to a plant body, spray comprising applying, to the plant seed, the plant disease and treatment to the Soil Surface, Soil incorporation after spray insect damage control composition according to claim 1. treatment to the soil Surface, injection treatment into the soil. or soil drenching treatment. ck