US00810 1657B2

(12) United States Patent (10) Patent No.: US 8,101,657 B2 Yamada et al. (45) Date of Patent: Jan. 24, 2012

(54) PLANT DISEASE AND INSECT DAMAGE JP 8-198713 A 8, 1996 CONTROL COMPOSITION AND PLANT JP 8-245322 A 3. 1996 DISEASE AND INSECT DAMAGE E. 56 A. E. PREVENTION METHOD JP 9-235282 A 9, 1997 JP 11-5708 A 1, 1999 (75) Inventors: Eiichi Yamada, Chiba (JP); Ryutaro JP 11-228309 A 8, 1999 Ezaki, Yasu (JP); Hidenori Daido, JP 11-292.715 A 10, 1999 Chiba (JP) JP 11-302107 A 11, 1999 JP 11-302108 A 11, 1999 JP 11-302109 A 11, 1999 (73) Assignee: Mitsui Chemicals, Inc., Minato-ku, JP 11-302110 A 11, 1999 Tokyo (JP) JP 11-302111. A 11, 1999 JP 11-322511 A 11, 1999 (*) Notice: Subject to any disclaimer, the term of this E. 585. A 33: patent is extended or adjusted under 35 JP 2001-72513 A 3, 2001 U.S.C. 154(b) by 418 days. JP 2001-810O3. A 3, 2001 JP 2004-538325 A 12, 2004 (21) Appl. No.: 12/516,966 JP 2005-517714. A 6, 2005 JP 2006-213664 A 8, 2006 (22) PCT Filed: Nov. 22, 2007 WO WO 2006/036827 A1 4/2006 9 WO WO 2006/069654 A2 T 2006 WO WO 2006/069655 A1 T 2006 (86). PCT No.: PCT/UP2007/072635 WO WO 2006/082723 A1 8, 2006 WO WO 2006/094978 9, 2006 S 371 (CI), WO WO 2007/010O36 A2 1, 2007 (2), (4) Date: May 29, 2009 WO WO 2008/OO3738 1, 2008 (87) PCT Pub. No.: WO2008/065960 OTHER PUBLICATIONS PCT Pub. Date: Jun. 5, 2008 Webster's New World Dictionary, 2nd college ed., The World Pub lishing Co., NY, entry for “prevent.” p. 1127 (1972). (65) Prior Publication Data Derwent abstract 2006-573208; abstracting JP 2006-213664 (Aug. US 201O/OO71096 A1 Mar. 18, 2010 2006). Machine translation of JP 2006-213664 (Aug. 2006). (30) Foreign Application Priority Data Translation of JP 2006-213664 (Aug. 2006). International Search Report (PCT/ISA/210) dated Jan. 8, 2008. Written Opinion (PCT/ISA/237) dated Jan. 8, 2008. Nov. 29, 2006 (JP) ...... 2006-321404 International Search Report (PCT/ISA/210) dated Jan. 7, 2008. (51) Int. Cl. Written Opinion (PCT/ISA/237) dated Jan. 7, 2008. AOIN 43/08 (2006.01) * cited by examiner AOIN 43/80 (2006.01) AOIN 43/653 (2006.01) Primary Examiner — John Pak AOIN 4I/06 (2006.01) (74) Attorney, Agent, or Firm — Buchanan Ingersoll & (52) U.S. Cl...... 514/471; 514/.461; 514/380: 514/383; Rooney PC 514/604:504/100 (58) Field of Classification Search ...... 514/.461, (57) ABSTRACT 514/471, 380,383, 604: 504/100 The invention provides a plant disease and insect damage See application file for complete search history. control composition including, as active ingredients, dinote furan and at least one fungicidal compound; and a plant (56) References Cited disease and insect damage prevention method that includes applying Such a composition to a plant body, Soil, plant seed, U.S. PATENT DOCUMENTS stored cereal, stored legume, stored fruit, stored vegetable, 5,532,365 A 7, 1996 Kodaka et al. silage, stored flowering plant, or export/import timber. The 2004/01 18040 A1* 6/2004 Asrar et al...... 47,576 2005/OOO97O3 A1 1/2005 Wachendorff-Neumann et al. invention provides a new plant disease and insect damage 2006, OO63829 A1 3/2006 Andersch et al. control composition and a plant disease and insect damage 2008.0171658 A1 7/2008 Dyllick-Brenzinger et al. prevention method with very low toxicity to mammals and 2008/026 1811 A1 10, 2008 Krohn et al. fishes, the composition and method showing an effect against 2008/0274882 A1 11/2008 Krohn et al. plural pathogens and pest insects, including emerging resis 2010.0056594 A1 3/2010 Sakurai et al. tant pathogens and resistant pest insect, by application to a FOREIGN PATENT DOCUMENTS plant body, soil, plant seed, stored cereal, stored legume, JP 61-197553 A 9, 1986 stored fruit, stored vegetable, silage, stored flowering plant, JP 3-227904. A 10, 1991 or export/import timber. JP 7-179448 A 7, 1995 JP 8-198710 A 8, 1996 11 Claims, No Drawings US 8,101,657 B2 1. 2 PLANT DISEASE AND INSECT DAMAGE agents, and the like, and it is known that these will demon CONTROL COMPOSITION AND PLANT strate an effect, as single agents or mixtures thereof, by spray DISEASE AND INSECT DAMAGE treatment, coating treatment, dip treatment, or dressing treat PREVENTION METHOD ment to seeds. How ever, among these agents, it is reported that the control effect against rice bakanae disease of benomy1 FIELD OF THE INVENTION and thiophanate-methyl agents is falling. Moreover, while prochloraZ agents are applied against rice blast disease, The present invention relates to a plant disease and insect brown spot, bakanae disease, tulip bulb rot, and shallot dry rot damage control composition and a plant disease and insect disease, and pefurazoate agents are applied against rice blast damage prevention method. 10 disease, brown spot, bakanae disease, wheat pink Snow mold, and tulip bulb rot, other applications of there agents are not BACKGROUND OF THE INVENTION known. Moreover, mixtures of benomyl and thiuram are applied for: rice diseases of rice blast disease, seedling blight, It is described in Japanese Patent Application Laid-Open bakanae disease, brown spot, bacterial grain rot, bacterial (JP-A) No. 07-179448 that an effect is shown by dinotefuran 15 brown stripe and discolorations of rice; wheat-like cereal as an insecticidal compound, with application methods such diseases of barley Stripe, loose Smut, Cephalosporium stripe as foliar application and water application, against: Lepi and Scald; cucumber fusarium wilt; gummy stem blight; dopterous pests, such as the common cutworm, Chilo and the damping off tomato fusarium wilt; watermelon fusarium common cabbageworm; Hemiptera pests, such as the green wilt; soya bean purple seed stain; taros Alternaria leaf spot: house white fly, the cotton aphid, the comstock mealybug, Sugarcane Smut, Coix lacryma-jobi leaf blight; Smut, corn and the Southern green Stink bug; Coleoptera pests, such as seedling blight; Japanese pumpkin fusarium basal rot; shal the rice water weevil and the striped flea beetle; Diptera pests lots dry rot disease; garlic white rot; and yam root rot. How such as the house fly and the rice leaf miner; Thysanoptera ever, other applications thereof are not known. Moreover, pests such as onion thrips; Orthoptera pests, such as the since mixtures of benomyl and thiuram have a strong affect on Smoky brown cockroach and rice grasshopper, and the like. 25 aquatic animals, there are warnings against their use in places However, there are no indication that there is an effect shown where there is a possibility of dispersal or flow into rivers, for pest insect prevention by application procedures such as lakes, coastal areas, and culture ponds. spray treatment, coating treatment, dip treatment, dressing treatment, fumigation and Smoking treatment, and pressure DESCRIPTION OF THE INVENTION injection to plant seeds. 30 Moreover, it is described in JP-A No. 08-245322, JP-A No. Problem to be Solved by the Invention 08-245323, JP-A No. 08-29.1009, and JP-A No. 11-005708 that a composition containing dinotefuran and a fungicidal An object of the invention is to provide a new prevention compound shows, in the field of paddy rice cultivation, a composition and control method against disease and pest synergistic effect against rice blast disease (Pyricularia 35 damage to plant bodies, soil, plant seeds, stored cereals, Oryzae) and sheath blight disease (Rhizoctonia Solani) in stored legumes, stored fruits, stored vegetable, silage, stored application methods such as to seedling raising boxes. How flowering plants and export/import timber, wherein the pre ever, there is no indication that an effect is shown in disease vention composition and control method show an effect prevention and insect damage prevention by applications of against plural pathogens and pest insects, including emerging spray treatment, coating treatment, dip treatment, or dressing 40 resistant pathogens and resistant pest insects, yet have a very treatment to plant seeds. Furthermore, there is no indication low toxicity to mammals and fish, the composition being of the use of mixtures of fulsulfamide and/or hymexazol, with applied to the plant body, soil, plant seeds, stored cereals, dinotefuran, nor is there any indication of a synergistic effect stored legumes, stored fruits, stored vegetable, silage, stored due to mixed use. flowering plants and export/import timber. It is described in JP-A 61-197553 (Japanese Patent 45 Announcement No. 06-027113) that flusulfamide, as a fun Means for Solving the Problem gicidal compound, shows antimicrobial activity or growth inhibition activity to various plant pathogenic microbes As a result of carrying out diligent examination and inves across a wide range of plant diseases by spraying, soil Surface tigation, the present inventors have determined that a compo application, Soil incorporation application, seed dipping, and 50 sition in which at least one sort of fungicidal compound is root dust coating, root immersion of seedlings and the like, added to dinotefuran shows a high preventive effect at a low and flusulfamide shows a prominent effect especially against dose to plural types of disease damage and insect damage, and soil diseases where the number of effective control chemicals shows a stable preventive effect toward the above resistant are small. Furthermore, the above document mentions the pathogens and/or resistant pest insects, resulting of the inven possibility of concomitant use of flusulfamide with a pesti 55 tion. cide and the like. However, there is no indication of using That is, the means for Solving problem is as follows. fluSulfamide with dinotefuran or hymexaZol, or a synergistic 1. A plant disease and insect damage control composition effect thereof. comprising active ingredients of (RS)-1-methyl-2-nitro JP-A No. 03-227904 (Japanese Patent No. 2,860,492) and 3-(tetrahydro-3-furylmethyl)guanidine (common JP-A No. 08-198710 (Japanese Patent No. 3,608,830), and 60 name: dinotefuran) and at least one fungicidal com JP-A No. 08-198713 (Japanese Patent No. 3,608,831) dis pound selected from the group consisting of 2,4- close a synergistic effect of the concomitant use of flusulfa dichloro-C.C.C.-trifluoro-4'-nitro-m-toluenesulfonanil mide with a fungicidal compound, and the like. However, ide (common name: flusulfamide), 3-hydroxy-5- there is no indication of using flusulfamide with dinotefuran. methylisoxazol (common name: hymexaZol), and (RS)- As chemicals which prevent plant disease by applying to 65 2-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3- plant seeds there are, conventionally, benomyl agents, (trimethylsilyl)propan-2-ol (common aC. thiophanate-methyl agents, prochloraZ agents, pefurazoate simeconazole). US 8,101,657 B2 3 4 2. The plant disease and insect damage control composi rice diseases such as rice blast disease (Pyricularia tion according to claim 1, wherein the at least one fun Oryzae), brown spot (Cochliobolus miyabeanus), bakanae gicidal compound comprises 2,4-dichloro-C.C.C.-trif disease (Gibberellafiujikuroi); luoro-4'-nitro-m-toluenesulfonanilide (common name: wheat-like cereal diseases such as barley stripe (Pyreno flusulfamide). 5 phoragraminea), loose Smut (Ustilago nuda, Ustilago tritici, 3. The plant disease and insect damage control composi Ustilago nigra, Ustilago avenae), bunts (Tilletia caries, Tille tion according to claim 1, wherein the at least one fun tia pancicii), covered Smut (Ustilago hordei, Ustilago kol gicidal compound comprises 3-hydroxy-5-methylisox leli), scald (Rhynchosporium secalis), Septoria tritici leaf aZol (common name: hymexaZol). 4. The plant disease and insect damage control composi blotch (Septoria tritici), glume blotch (Leptosphaeria tion according to claim 1, wherein the at least one fun 10 nodorum), pink Snow mold (Microdochium nivale), Fusarium gicidal compound comprises (RS)-2-(4-fluorophenyl)- head blight (Fusarium graminearum, Fusarium culmorum, 1-(1H-1,2,4-triazol-1-yl)-3-(trimethylsilyl)propan-2-ol Fusarium avenaceum, Microdochium nivale), kernel blight (common name: Simeconazole). (Helminthosporium sativum), take-all (Gaeumannomyces 5. The plant disease and insect damage control composi graminis), Cephalosporium stripe (Cephalosporium tion according to claim 1, wherein the at least one fun 15 gramineum) and net blotch (Dreschlera teres); gicidal compound comprises a mixed composition of at corn diseases such as common Smut (Ustilago mydis); least two selected from the group consisting of flusulfa legume diseases such as seedling blight (Rhizoctionia mide, hymexaZol, and Simeconazole. Solani) and Sclerotinia stem rot (Sclerothinia Sclerotorium), 6. A plant disease and insect damage prevention method purple seed stain of Soya beans (Cercospora kikuchii) and comprising applying the pest control composition Rhizoctonia root rot (Rhizoctonia Solani); according to claim 1 to a plant body, soil, plant seed, diseases in Sugar beet such as root rot (Rhizotconia Solani); stored cereal, stored legume, stored fruit, stored veg rape diseases Such as black leg (Leptosphaeria maculans), etable, silage, stored flowering plant, or export/import alternaria leaf spot (Alternaria brassicae); timber. damping off (Rhizoctonia Solani) of various vegetables, 7. The plant disease and insect damage prevention method 25 Such as tomato, cucumber, Japanese radish, watermelon, egg according to claim 6, wherein the method of application plant, Sweet pepper, and spinach; and to plant seeds is spray treatment, coating treatment, dip treatment, or dressing treatment of seeds. diseases such as tomato wilt (Fusarium oxysporum), 8. The plant disease and insect damage prevention method cucurbitaceae Fusarium wilt (Fusarium oxysporum), cab according to claim 6, wherein the method of application bage yellows (Fusarium oxysporum), cauliflower chlorosis to a stored cereal, stored legume, stored fruit, stored 30 (Fusarium oxysporum), and Chinese cabbage Verticillium Vegetable, silage, stored flowering plants, or export/im wilt (Verticillium dahlie). port timber is spray treatment, coating treatment, dip Examples that may be given of the insect damage which treatment, dressing treatment, fumigation treatment, can be prevented include, but are not limited to, the following Smoke treatment, or pressure injection. from the order of grasshoppers, crickets and locusts 9. Plant seed, stored cereal, stored legume, stored fruit, 35 Examples that may be given of the insect damage which can stored vegetable, silage, stored flowering plant, or be prevented include, but are not limited to, the following export/import timber to which the plant disease and from the order of grasshoppers, crickets and locusts (Ortho insect damage control composition according to claim 1 ptera): has been applied. BLATTIDAE such as the American cockroach (Periplan 10. The plant disease and insect damage prevention method 40 eta americana), the Smokybrown cockroach (Periplaneta according to claim 6, wherein the method of application fiuliginosa), the Japanese cockroach (Periplaneta japonica); to a plant body or soil is foliar application to a plant body, BLATTELLIDAE such as the German cockroach (Blat spray treatment to the soil Surface, soil incorporation tella germanica), the false German cockroach (Blattella litu after spray treatment to the Soil Surface, injection treat ricollis); ment into the Soil, or soil drenching treatment. 45 TETTIGONIIDAE such as the northern rice katydid (Ho 11. A method of preventing plant disease and insect dam morocoryphus jezoensis), the northern rice katydid (Homo age to a plant body grown from a plant seed, the method rocoryphus lineosus); comprising applying, to the plant seed, the plant disease GRYLLOTALPIDAE such as the mole crickets (Gryllo and insect damage control composition according to talpa sp.); and claim 1. 50 ACRIDIDAE such as the short-horned grasshoppers (Oxya hyla intricata) and rice grasshopper (Oxya yezoensis); Effect of the Invention the following from the order of Termites/White Ants (ISOPTERA): the dry-wood termite (Cryptotermes domesti The method of the invention, while demonstrating a high cus), the Formosan Subterranean termite (Coptotermes for preventive effect to disease damage and insect damage gen 55 mosanus), the Japanese Subterranean termite (Reticulitermes erated in plant bodies, soil, plant seeds, stored cereals, stored speratus), the macrotermitine termite (Odontotermes formo legumes, stored fruits, stored vegetables, silage, stored flow Sanus); ering plants, and export/import timber, also shows a stable the following from the order of thrips (THYSAN preventive effect to microbe pathogens and pest insects that OPTERA): are resistant to existing chemicals. 60 THRIPIDAE such as the grass thrips (Anaphothrips obscu rus), the cockSfoot thrips (Chirothrips manicatus), the cha BEST MODE OF CARRYING OUT THE nokuro-azamiuma (Dendrothrips minowai), the flower thrips INVENTION (Frankliniella intonsa), the yurikiiro-azamiuma (Franklin iella lilivora), the greenhouse thrips (Heliothrips haemor Specific examples of the types of disease damage which 65 rhoidalis), the composite thrips (Microcephalothrips may be prevented with the method of the invention include, abdominalis), the oriental Soybean thrips (Mycterothrips gly but are not limited to, the following: cines), the mulberry thrips (Pseudodendrothrips mori), the US 8,101,657 B2 5 6 yellow tea thrips (Scirtothrips dorsalis), the redbanded (Sele Sugarbeet leaf bug (Orthotylus flavosparsus), the wheat leaf nothrips rubrocinctus), the oriental rice thrips (Stenchaeto bug (Stenodema calcaratum), the timothy grassbug (Stenotus thrips biformis), the neglkuro-azamiuma (Thrips alliorum), binotatus), the Sorghum plant bug (Stenotus rubrovittatus), the loquat thrips (Thrips coloratus), the honeysuckle thrips the brokenbacked bug (Taylorilygus pallidulus), the rice leaf (Thrips flavus), the Hawaiian flower thrips (Thrips hawaiien bug (Trigonotylus coelestialium); sis), the chrysanthemum thrips (Thrips nigropilosus), the CICADIDAE such as the large brown cicada (Graptopsal melon thrips (Thrips palmi), the western flower thrips (Fran tria nigrofiscata); Kliniella occidentalis), the Japanese flower thrips (Thrips APHROPHORIDAE such as the maeki-awafuki (Aphro setosus), the gladiolus thrips (Thrips simplex), the onion phora costalis), the pine froghopper (Aphrophora flavipes), thrips (Thrips tabaci); 10 the common Spittlebug (Aphrophora intermedia), the PHLAEOTHRIPIDAE such as the rice aculeated thrips himefutatennaga-awafuki (Clovia punctata), the meadow (Haplothrips aculeatus), the Chinese thrips (Haplothrips Spittlebug (Philaenus spumarius); chinensis), the hana-kudaaZamiuma (Haplothrips kurdiu TETTIGELLIDAE such as the black-tipped leafhopper movi), the red clover thrips (Haplothrips niger), the shi (Bothrogonia japonica), the greenleafhopper (Cicadella viri ionaga-kudaaZamiuma (Leeuwania pasanii), the camphor 15 dis); thrips (Liothrips floridensis), the lily thrips (Liothrips CICADELLIDAE such as the oak leafhopper (Aguriahana vaneeckei), the thrip (Litotetothrips pasaniae), the Japanese quercus), the polyphagous leafhopper (Alnetoidia alneti), the gall-forming thrips (Ponticulothrips diospyrosi); citrus leafhopper (Aphelioma ferruginea), the grape Leafhop the following from the order of the true bugs (HEMI per (Arboridia apicalis), the Small green leafhopper (Ed PTERA): PENTATOMIDAE such as the purple stink bug wardsiana flavescens), the rose leafhopper (Edwardsiana (Carpocoris purpureipennis), the sloe bug (Dolycoris bac rosae), the pine leafhopper (Empoasca abietis), the tea green carum), the painted bug (Eurydema pulchrum), the cabbage leafhopper (Empoasca Onuki), the orange headed leafhopper bug (Eurydema rugosum), the Two-spotted sesame bug (Thaia subrufa), the Smaller citrus leafhopper (Zyginella (Eysarcoris guttiger), the Ootogeshirahoshi-kamemushi citri): (Eysarcoris lewisi), the white spotted spined Stink bug 25 DELTOCEPHALIDAE such as aster leafhopper (Macros (Eysarcoris parvus), the shieldbug (Eysarcoris ventralis), the teles fasci?ions), the green rice leafhopper (Nephotettix cinc polished green Stink bug (Glaucias subpunctatus), the red ticeps), the green rice leafhopper (Nephotettix nigropictus), stripped Stink bug (Graphosoma rubrolineatum), the brown the green rice leafhopper (Nephotettix virescens), the apple malmorated Stink bug (Halyomorpha mista), the rice Stink leafhopper (Orientus ishidai), the Zig-Zag rice leafhopper bug (Lagynotomus elongatus), the oriental green Stink bug 30 (Recilia dorsalis), the wheat leafhopper (Sorhoanus tritici), (Nezara antennata), the Southern green Stink bug (Nezara the alder leafhopper (Speudotettix subfusculus); viridula), the redbanded shieldbug (Piezodorus hybneri), the DELPHACIDAE such as the small brown planthopper brown-winged green bugs (Plautia Stali), the black rice bug (Laodelphax striatellus), the brown planthopper (Nilapar (Scotinophara lurida), the brown rice Stink bug (Starioides vata lugens), the pale Sugarcane planthopper (Numata muiri), degenerus); 35 the maize planthopper (Peregrinus maidis), the Sugarcane COREIDAE such as the winter cherry bug (Acanthocoris leafhopper (Perkinsiella saccharicida), the white-backed SOrdidus), the Coreid-hug (Anacanthocoris Stricornis), the planthopper (Sogatella furcifera), the panicum planthopper rice Stink bug (Cletus punctiger), the slender rice bug (Cletus (Sogatella panicicola); trigonus), the Leaf-Footed Bug (Molipteryx filliginosa); PSYLLIDAE such as the mulberry sucker (Anomomeura ALYDIDAE Such as the paddy bug (Leptocorisa acuta), 40 mori), the lacquer psylla (Calophya nigridorsalis), the citrus the rice bug (Leptocorisa chinensis), the rice bug (Lepto psylla (Diaphorina citri), the hibiscus psylla (Mesohomo corisa Oratorius), the bean bug (Riptortus clavatus); toma camphorae), the abies psylla (Psylla abieti), the Plant RHOPALIDAE such as the carrot bug (Aeschynteles macu louse (Psylla alni), the sins psylla (Acizzia jamatonica), the latus), the hyaline grass bug (Liorhyssus hyalinus); apple Sucker (Cacopsylla mali), the black apple Sucker LYGAEIDAE such as the oriental chinch bug (Cavelerius 45 (Psylla malivorella), the pear Sucker (Psylla pyrisuga), the saccharivorus), the bamboo chinch bug (Macropes obnubi tobira psylla (Psylla tobirae), the camphor sucker (Trioza lus), the hiratahyoutan-nagakamemushi (Pachybrachius luri camphorae), the guercus Sucker (Trioza quercicola); dus), the kuroashihoso-nagakamemushi (Paromius jejunus), ALEYRODIDAE such as the orange spiny whitefly (Aleu the seed bug (Togo hemipterus); rocanthus spiniferus), the grape whitefly (Aleurolobus taona PYRRHOCORIDAE such as the cotton bug (Dysdercus 50 bae), the tobacco whitefly (Bemisia tabaci), the citrus white cingulatus), the Small cotton bug (Dysdercus poecilus); fly (Dialeurodes citri), the greenhouse whitefly (Trialeurodes TINGIDAE such as the chrysanthemum lace bug (Galea vaporariorum), the silverleaf whitefly (Bemisia argentifolii); tus spinifrons), the yanagi-gunbai (Metasalis populi), the PHYLLOXERIDAE such as the vine phylloxera (Viteus camphorlace bug (Stephanitis fasciicarina), the pear lace bug vitifolii); (Stephanitis nashi), the azalea lace bug (Stephanitis pyrio 55 PEMPHIGIDAE such as the root aphid (Aphidounguis ides), the chestnut lace bug (Uhlerites debile), the walnut lace mali), the woolly aphid (Eriosoma lanigerum), the Sugarcane bug (Uhlerites latiorus); root aphid (Geoica lucifiiga); MIRIDAE such as the alfalfa plant bug (Adelphocoris lin APHIDIDAE such as the pea aphid (Acyrthosiphon eolatus), the buchihigekuro-kasumikame (Adelphocoris tri pisum), the spirea aphid (Aphis citricola), the cowpea aphid annulatus), the koao-kasumikame (Apolygus lucorum), the 60 (Aphis craccivora), the yanabi-aburamushi (Aphis farinosa pale green plant bug (Apolygus spinolai), the akahoshi-ka vanagicola), the cotton aphid (Aphis gossypii), the foxglove Sumikame (Creontiades coloripes), the tobacco leaf bug (Ne aphid (Aulacorthum Solani), the leafcurl plum aphid (Brachy Sisiocoris tenuis), the Japanese garden fleahopper (Ectome caudus helichrysi), the cabbage aphid (Brevicoryne brassi topterus micantulus), the oriental garden fleahopper cae), the tulip bulb aphid (Dysaphis tulipae), the European (Halticiellus insularis), the apple leaf bug (Heterocordylus 65 birch aphid (Euceraphis punctipennis), the mealy plum aphid flavipes), the Japanese tarnished plant bug (Lygus disponsi), (Hyalopterus pruni), the turnip aphid (Lipaphis erysimi), the the madara-kasumikame (Cyphodemidea Saundersi), the chrysanthemum aphid (Macrosiphoniella Sanborni), the US 8,101,657 B2 7 8 potato aphid (Macrosiphum euphorbiae), the bean aphid raeses phaseoli), the apple fruit licker (Spilonota lechrias (Megoura crassicauda), the nashikofuki-aburamushi pis), the eyespotted bud moth (Spilonota ocellana), the Euro (Melanaphis siphonella), the apple leafcurling aphid (Myzus pean grape berry moth (Eupoecillia ambiguella), the Chinese malisuctus), the umekobu-aburamushi (Myzus numecola), arrowed stemborer (Gymnidomorpha mesotypa), the yomo the green peach aphid (Myzus persicae), the onion aphid 5 gioo-hosohamaki (Phtheochroides clandestina), the mul (Neotoxoptera formosana), the apple aphid (Ovatus malico berry bagworm (Bambalina sp.), the giant bagworm (Eumeta lens), the waterlily aphid (Rhopalosiphum nymphaeae), the japonica), the tea bagworm (Euneta minuscule), the Euro bird-cherry aphid (Rhopalosiphum padi), the rice root aphid pean grain moth (Nemapogon granellus), the casemaking (Rhopalosophum rufiabdominalis), the root aphid (Sappa clothes moth (Tinea translucens), the pear leaf miner (Buc phispiri), the pearaphid (Schizaphispiricola), the gain aphid 10 culatrix pyrivOrella), the peach leafminer (Lyonetia cler (Sitobion akebiae), the ibarahigenaga-aburamushi (Sitobion kella), the apple leafminer (Lyonetia prunifoliella), the Soy ibarae), the tea aphid (Toxoptera aurantii), the brown citrus bean leafroller (Caloptilia sovella), the tea leafroller aphid (Toxoptera citricidus), the peach aphid (Tuberoceph (Caloptilia theivora), the ringo-hosoga (Caloptilia Zach alus mononis), the taiwanhigenaga-aburamushi (Uroleucon rysa), the persimmon leafminer (Cuphodes diospyrosella), formosanum); 15 the apple leafminer (Phyllonorycter ringoniella), the pear MARGARODIDAE such as the giant mealybug (Drosicha barkminer (Spullerina astaurota), the citrus leafminer (Phyl corpulenta), the cottony cushion scale (Icerya purchasi); locnistis citrella), the grape leafminer (Phyllocnistis topar PSEUDOCOCCIDAE such as the matsumoto mealybug cha), the allium leafminer (Acrolepiopsis sapporensis), the (Crisicoccus matsumotoi), the Kuwana Pine Mealybug (Cri yam leafminer (Acrolepiopsis suzukiella), the diamondback sicoccus pini), the Taxus mealybug (Dysmicoccus wistariae), 20 moth (Plutella xylostella), the apple fruit moth (Argyresthia the citrus mealybug (Planococcus citri), the Japanese mealy conjugella), the vine tree borer (Paranthrene regalis), the bug, the (Planococcus kranuhiae), the citrus mealybug cherry tree borer (Synanthedon hector), the persimmon fruit (Pseudococcus citriculus), the comstock mealybug (Pseudo moth (Stathmopoda masinissa), the Sweetpotato leaf folder coccus Comstocki); (Brachnia triannulella), the peach fruit moth (Carposina COCCIDAE such as the Indian wax scale (Ceroplastes 25 niponensis), the pear leaf worm (Illiberispruni), the Chinese ceriferus), the red wax scale (Ceroplastes rubens), the mikan cochlid (Parasa sinica), the oriental moth (Monema flave hiratakaigaramushi (Coccus discrepans), the brown soft Scale scens), the pear stinging caterpillar (Narosoideus flavidorsa (Coccus hesperidum), the citricola Scale (Coccus pseudo lis), the green cocklid (Parasa consocia), the persimmon magnoliarum), the Chinese wax scale (Ericerus pela), the cochlid (Scopelodes contracus), the rice stem borer (Chilo European fruit lecanium scale (Lecanium corni), the Euro 30 suppressalis), the rice leaffolder moth (Cnaphalocrocis medi pian peach scale (Lecanium persicae), the citrus cottony Scale nalis), the yellow peach moth (Conogethes punctiferalis), the (Pulvinaria aurantii), the soft scale (Pulvinaria citricola), the cotton caterpillar (Diaphania indica), the nashimadara cottony mulberry Scale (Pulvinaria kuwacola); meiga (Ectomyelois pyrivorella), the Mediterranean flour DIASPIDIDAE such as the kankitsu-kaigaramushi (An moth (Ephestia kuehniella), the limabean pod borer (Etiella daspis kashicola), the California red scale (Aonidiella auran 35 Zinckenella), the persimmon bark borer (Euzophera batan tii), the yellow scale (Aonidiella citrina), the coconut Scale gensis), the mulberry pyralid (Glyphodes pyloalis), the cab (Aspidiotus destructor), the oleander Scale (Aspidiotus hed bage webworm (Hellulla undalis), the rice leafroller (Maras erae), the circular black scale (Chrysomphalus ficus), the San mia exigua), the legume pod borer (Maruca testulalis), the Jose scale (Comstockaspis perniciosa), the camellia mining cotton leafroller (Notarcha derogate), the Asian corn borer scale (Duplaspidiotus claviger), the purple scale (Lepi 40 (Ostrinia firmacalis), the azuki bean borer (Ostrinia Scapu dosaphes beckii), the oystershell scale (Lepidosaphes ulmi), lalis), the butterbur borer (Ostrinia zaguliaevi), the bluegrass the Japanese maple scale (Lepidosaphes japonica), the scale webworm (Parapediasia teterrella), the bean webworm (Parlatoreopsis pyri), an armored scale (Parlatoria camel (Pleuroptya ruralis), the yellow stem borer (Scirpophaga liae), the tea parlatoria Scale (Parlatoria theae), the black incertulas), the rice skipper (Parnara guttata), the red helen parlatoria Scale (Parlatoria Ziziphi), the fern scale (Pinnaspis 45 (Papilio helenus), the common yellow swallowtail (Papilio aspidistrae), the camphor Scale (Pseudaonidia duplex), the machaon), the Swallowtail butterfly (Papilio xuthus), the east peony scale (Pseudaonidia paeoniae), the mulberry Scale ern pale clouded yellow (Colias erate poliographus), the (Pseudaulacaspis pentagona), the white prunicola scale common cabbageworm (Pieris rapae crucivora), the long (Pseudaulacaspis prunicola), the arrowhead scale (Unaspis tailed pea-blue (Lampides boeticus), the orange moth (Ange vanonensis); 50 roma prunaria), the Japanese giant looper (Ascotis selenaria), the following from the order of the butterflies, moths and the phytomimetic giant geometer (Biston robustum), the skippers (LEPIDOPTERA): swift moth (Endoclita excre plum cankerworm (Cystidia couaggaria), the pine caterpillar scens), the grape treeborer (Endoclita Sinensis), the moth (Dendrolimus spectabilis), the tent caterpillar (Malacosoma (Palpifer sexnotata), the strawberry tortrix moth (Acleris neustria testacea), the apple caterpillar (Odonestis pruni comariana), the Summer fruit tortrix moth (Adoxophyes 55 japonensis), the coffee hawk moth (Cephonodes hylas), the Orana fasciata), the Smaller tea tortrix moth (Adoxophyes grape horn worm (Acosmeryx castanea), the scarce choco sp.), the Asiatic leafroller (Archips breviplicanus), the apple late-tip (Clostera anachoreta), the poplar prominent tortrix (Archips fiascocupreanus), the brown oak tortrix (Ar (Clostera anastomosis), the Japanese buff-tip moth (Phalera chips xylosteanus), the mat rushworm (Bactra furfurana), the flavescens), the oak caterpillar (Phalerodonta manleyi), the tobacco leaf worm (Cnephasia cinereipalpana), the nut fruit 60 lobster moth (Stauropus fagipersimilis), the tea tussock moth tortrix (Cydia kurokoi), the greenish chestnut moth (Eu (Euproctis pseudoconspersa), the brown-tail moth coenogenes aestuosa), the oriental fruit moth (Grapholita (Sphrageidus similis), the oriental tussock moth (Artaxa sub molesta), the oriental tea tortrix (Homona magnanima), the flava), the gypsy moth (Lymantria dispar), the white-spotted leafroller (Choristoneura adumbratana), the Soybean pod tussock moth (Orgvia thyellina), the Fall webworm moth borer (Leguminivora glycinivorella), the adzuki bean pod 65 (Hyphantria cunea), the mulberry tiger moth (Spilosoma worm (Matsumuraeses azukivora), the Soybean pod worm imparilis), the three-spotted plusia (Acanthoplusia agnata), (Matsumuraeses falcana), the Soybean pod worm (Matsumu the eastern alchymist (Aedia leucomelas), the black cutworm US 8,101,657 B2 10 (Agrotis ipsilon), the turnip moth (Agrotis segetum), the hibis the following from the sawfly, wasp, bee, and ant order cus looper (Anomis mesogona), the beet semi-looper (Au (HYMENOPTERA): the cabbage sawfly (Athalia japonica), tographa nigrisigna), the cabbage looper (Trichoplusia ni), the turnip Sawfly (Athalia rosae ruficornis), the apple argid the cotton bollworm (Helicoverpa armigera), the capegoose sawfly (Arge mali), the large rose sawfly (Arge pagana) and berry budworm (Helicoverpa assulta), the flax budworm (He the oriental chestnut gall wasp (Dryocosmus kuriphilus); liothis maritime), the cabbage Moth (Mamestra brassicae), the following from the fly order (DIPTERA): the rice crane the rice green caterpillar (Naranga aenescens), the oriental fly (Tipula aino), the Sciarid fly (Bradysia agrestis), the Soy armyworm (Pseudaletia separata), the pink stem borer bean pod gall midge (Asphondylia sp.), the melon fly (Dacus (Sesamia inferens), the lawn grass cutworm (Spodoptera dep cucurbitae), the oriental fruit fly (Dacus dorsalis), the citrus 10 fruit fly (Dacus tsuneonis), the Japanese cherry fruitfly (Rha ravata), the beet armyworm (Spodoptera exigua), the com cochlaena japonica), the rice leafminer (Hydrelia griseola), mon cutworm (Spodoptera litura), the apple dagger moth the rice whorl maggot (Hydrellia Sasakii), the cherry droso (Trianea intermedia), the sorrel cutworm (Viminia rumicis), phila (Drosophila Suzukii), the rice stem maggot (Chlorops the cutworm (Xestia c-nigrum); Oryzae), the wheat stem maggot (Meromyza nigriventris), the the following of the beetle order (COLEOPTERA): brown 15 Japanese rice leaf miner (Agromyza Oryzae), the pea leaf chafer (Adoretus tenuimaculatus), the cupreous chafer miner (Chromatomyia horticola), the celery miner fly (Liri (Anomala cuprea), the Soybean beetle (Anomala rufocuprea), omyza bryoniae), the stone leek leafminer (Liriomyza chin the flower beetle (Eucetonia pilifera), the aohanamuguri (Ce ensis), the American serpentine leafminer (Liriomyza tri tonia roelofsi), the yellowish elongate chafer (Heptophylla folii), the vegetable leafminer (Liriomyza sativae), the pea picea), the Japanese cockchafer (Melolontha japonica), the leafminer (Liriomyza huidobrensis), the onion fly (Delia anti scarab beetle (Mimela splendens), the citrus flower chafer qua), the bean seed fly (Delia platura), the beet leaf miner (Oxycetonia jucunda), the Japanese beetle (Popillia (Pegomya cunicularia), the house fly (Musca domestica), the japonica), the varied carpet beetle (Anthrenus verbasci), the blowfly (Phormia regina), the house-gnat (Culex pipiens pal black carpet beetle (Attagenus unicolor japonicus), the ciga lens Coquillett), the chikaieka (Culex pipiens molestus For rette beetle (Lasioderma serricorne), the powderpost beetle 25 skal), the shina-hamadaraka (Anopheles (Anopheles) sinensis (Lyctus brunneus), the corn Sap beetle (Carpophilus dimid Wiedemann), and the Asian tiger mosquito (Aedes albopictus iatus), the dried fruit beetle (Carpophilus hemipterus), the (Skuse)). leaf feeding ladybird (Epilachna vigintioctomaculata), the In addition, examples that may be given of stored grain phytophagous ladybird beetle (Epilachna vigintioctopunc insects that may be controlled by the invention include, the tata), the black fungus beetle (Alphitobius laevigatus), the 30 but are not limited to, the following: the redlegged hambeetle yellow-dappled longicorn (Neatus picipes), the Smalleyed (Necrobia rufipes), the Soybean beetle (Calosobruchus ana flour beetle (Palorus ratzeburgii), the depressed flour beetle lis), the redshouldered hambeetle (Necrobia ruficollis), the (Palorus subdepressus), the yellow mealworm (Tenebrio Pineapple beetle (Urophorus humeralis), the American spi molitor), the red flour beetle (Tribolium castaneum), the con der beetle (Mezium americanum), the stored nut moth fused flour beetle (Tribolium confiusum), the bean blister 35 (Parallipsagularis), the bean weevil (Acanthoscelides Obtec beetle (Epicauta gorhami), the kimadara-kamikiri (Aeoles tus), the pea weevil (Bruchus pisorum), the Australian spider thes chrysothrix), the white spotted longicornbeetle (Anoplo beetle (Ptinus tectus), the larger grain borer (Prostephanus phora malasiaca), the Japanese pine Sawyer (Monochamus truncatus), the broad-horned flour beetle (Gnathocerus cor alternatus), the yellow-spotted longicorn beetle (Psacothea nutus), the merchant grain beetle (Oryzaephilus mercator), hilaris), the grape borer (Xylotrechus pyrrhoderus), the mon 40 the meal moth (Pyralis farinalis), the Kashmir flour beetle keypod round-headed borer (Xystrocera globosa), the azuki (Tribolium freemani), the foreign grain beetle (Ahasverus bean weevil (Callosobruchus chinensis), the cucurbit leaf advena), the lesser meal worm (Alphitobius diaperinus), the beetle (Aulacophora femoralis), the chairosaru-hamushi rice moth (Corcyra cephalonica), the golden spider beetle (Basilepta balvi), the tortoise beetle (Cassida nebulosa), the (Niptus holoeucus), the granary weevil (Sitophilus grana tensaitobi-hamushi (Chaetocnema concinna), the Sweetpo 45 ries), the black flour beetle (Tribolium madens), the destruc tato leaf beetle (Colasposoma dauricum), the juushihoshiku tive flour beetle (Tribolium destructor), the Nemapogon binaga-hamushi (Crioceris quatuordecimpunctata), the rice (Nemapogon granella), the maize weevil (Sitophilus zea rootworm (Donacia provosti), the ruri-hamushi (Linaeidea mais), the broadnosed grain weevil (Caulophilus Oryzae), the aenea), the Soybean flea beetle (Luperomorpha tenebrosa), cadelle beetle (Tenebroides mauritanicus), the grain worm the two-striped leaf beetle (Medythia nigrobilineata), the rice 50 (Martyringa xeraula), the longheaded flour beetle (Latheti leaf beetle (Oulema oryzae), the tropical legume leaf beetle cus oryzae), the slenderhorned flour beetle (Gnathocerus (Pagria signata), the daikon leaf beetle (Phaedon brassicae), maxillosus), the lesser grain borer (Rhizopertha dominica), the striped flea beetle (Phyllotreta striolata), the umechok the mould beetle (Aridius modifer), the sap beetle (Carpophi kiri-Zoumushi (Involvulus cupreus), the peach curculio lus pilosellus), the dark mealworm (Tenebrio obscurus), the (Rhynchites heros), the Sweet potato weevils (Cylas formi 55 black rice worm (Aglossa dimidiata), the rusty grain beetle carius), the apple blossom weevil (Anthonomus pomorum), (Cryptolestes ferrugineus), the drugstore beetle (Stegobium the daikonsaru-Zoumushi (Ceutorhynchus albOsuturalis), the paniceum), the almond moth (Ephestia cautella), the broad chestnut weevil (Curculio Sikkimensis), the rice plant weevil bean weevil (Bruchus rufimanus), the square-necked grain (Echinocnemus squameus), the West Indian Sweetpotato beetle (Cathartus quadricollis), the hairy fungus beetle weevil (Euscepes postfasciatus), the lesser clover-leaf weevil 60 (Tiphaea stercorea), the tsuyahimemakimusshi (Holopar (Hypera nigrirostris), the alfalfa weevil (Hypera postica), the amecus signatus), the seed beetle (Pagiocerus frontalis), the rice water weevil (Lissorhoptrus Oryzophilus), the vegetable niseduriyakesikisui (Carpophilus delkeskampi), the spider weevil (Listroderes costirostris), the leaf weevil (Phyllobius beetle (Gibbium aequinoctiale), the sawtoothed grain beetle armatus), the chibikofuki-Zoumushi (Sitona japonicus), the (Oryzaephilus Surinamensis), the Indian-meal moth (Plodia rice weevil (Sitophilus oryzae), the maize weevil (Sitophilus 65 interpunctella), the hide beetle (Dermestes maculates), the Zeanais), the hunting billbug (Sphenophrus venatus vesti cowpea weevil (Callosobruchus phaseori), the rusty grain tus): beetle (Cryptolestes pusilloides), the angoumois grain moth US 8,101,657 B2 11 12 (Sitotroga cerealella), the khaprabeetle (Trogoderma grana dithiocarbamate fungicides, such as thiuram, mancoZeb, rium), the brown spider beetle (Ptinus clavipes), the larger propineb, Zineb, metiram, maneb, Ziram, and amobam; cabinet beetle (Trogoderma inclusium), the lentil pest (Bru soil disinfectants, such as hydroxyisoxazol (hymexaZol), chus lentis), a the futagomameZoumushi (Callosobruchus methasulfocarb, chloropicrin, flusulfamide, dazomet, meth subinnotatus), the Mexican bean weevil (Zabrotes subfascia ylisothiocyanate, potassium salt of hydroxyisoxazol, etridi tus), the vetch bruchid (Bruchus brachialis), the Siamese azole, 1,3-dichloropropene, and carbam; grain beetle (Lophocaterus pusillus), the munabirohimeha organochlorine fungicides, such as TPN and captan; makimushi (Dienerella costulata), the Mexican grain beetle anilino pyrimidine fungicides, such as mepanipyrim, (Pharaxonotha kirschii), the peanut bruchid (Carvedon ser cyprodinil, and pyrimethanil; 10 natural products, such as rapeseed oil and machine oil; ratus), the cowpea bruchid (Callosobruchus maculatus), the inorganic fungicides, such as Sulfur, lime Sulfur mixture, checkered beetle (Necrobia violacea), the rhodesian bean Zinc sulfate, fentin, sodium hydrogencarbonate, potassium weevil (Callosobruchus rhodesianus) and the coffee bean hydrogencarbonate, and hypochlorite; weevil (Araecerus fasciculatus). morpholine fungicides, such as dimethomorph, fempropi Examples that may be given of timber pest insects that may 15 din, fenpropimorph, Spiroxamine, tridemorph, dodemorph, be controlled by the invention include, but are not limited to and flumorph; the following: the nisima-kikuimushi (Sueus misimai), the fungicides, such as iprovalicarb, imazalil-S, iminoctadine coffee-kikuimushi (Taphronychus coffeae), the Sazankako albesilate, quinoxyfen, chinomethionat, metallic silver, chlo atomaru-kikuimushi (Poecilips Oblongus), the black twig rothalonil, chloroneb, cyazofamid, diethofencarb, dichloflu borer (Xylosandrus compactus), the mulberry bark beetle anid, dichloram, dithianon, diflumetorim, dimethirimol, (Xvleborus atratus), the futairo-kikuimushi (Xvleborus cymoxanil, silthiofam, spiroxamine, Zoxamide, thiadiazine bicolor), the akagashinoki-kikuimushi (Xvleborus cincisus), (minleb), dodine, triforine, tolylfluanid, nitrothal-isopropyl, redbay ambrosia beetle (Xvleborus glabratus), the aino famoxadone, fenamidone, fenitropan, fenpiclonil, fenhexa kikuimushi (Xvleborus interjectus), camphor shot borer (Xy mid, folpet, fluazinam, fluopicolide, fluoroimide, propam losandrus mutilatus) and the todomatsuoo-kikuimushi (Xvle 25 ocarb, propamocarb hydrochloride, propylene glycol fatty borus validus). acid esters, calcium salt of prohexadione, benthiazole, The following may be given as examples of the fungicidal benthiavalicarb-isopropyl, myclobutanil, organic nickel, res compound included in the pest control composition of the Veratrol, diclomeZine, iminoctadine acetate, isoprothiolane, invention, but it should be noted that the invention is not tiadinil, probenazole, acibenzolar-S-methyl, fludioxonil, fos limited thereto. 30 etyl-aluminum, guazatline and triaZOxide. The examples include: carboxamide fungicides, such as In the invention, a plant seed refers to something that stores thifluzamide, flutolanil, mepronil, pencycuron, ethaboxam, nutrients for seedlings to sprout and is used for propagation in oxycarboxin, carboxin, and silthiofam; agriculture. Specific examples that may be given include, but melanin biosynthesis inhibitor fungicides, such as carpro are not limited to: seeds, such as of corn, Coix lacrymajoli pamid, diclocymet, tricyclazole, pyroquilon, fenoxanil, and 35 (Job's Tears), Japanese millet, buckwheat, soya bean, azuki fthalide; bean, common bean, pea, broad bean, peanut, hyacinth bean, strobilurin fungicides, such as azoxystrobin, metominos cabbage, Brussels sprout, Japanese radish, nonhead-forming trobin, orysastrobin, kresoxim-methyl, fluoxastrobin, triflox brassica leaf vegetables, cotton, rice, Sugar beet, table beet, yStrobin, dimoxystrobin, pyraclostrobin, and picoxystrobin; wheat, barley, Sunflower, tomato, cherry tomato, chilli pep antibiotics, such as kasugamycin, validamycin, benzy 40 pers, cucumber, watermelon, bitter melon, melon, oriental laminobenzenesulfonic acid salt of blasticidin-S, tecloftalam, pickling melon, winter melon, eggplant, spinach, podded pea, oxytetracycline, Streptomycin, blasticidin-S, mildiomycin, greenbean, immature broadbean, greenpea, asparagus, okra, and polyoxins; garland chrysanthemum, carrot, parsley, Welsh onion, Scal pyrimidine fungicides, such as ferimZone, fenarimol, lion, lettuce, non head-forming lettuces, Japanese pumpkin, pyrifenox, nuarimol, and bupirimate; 45 Sugarcane, tobacco, Sweet pepper, rape, rye, and oats; seed azole fungicides, such as Simeconazole, furametpyr, tubers, such as taro, potato, Sweet potato, yam and konnyaku: ipconazole, triflumizole, prochloraz, pefurazoate, imazalil, bulbs, such as edible lily, tulip, narcissus, hyacinth, amaryllis, imibenconazole, etridiazole, epoxiconazole, fumaric acid salt lily, gladiolus and crocus; and seed bulbs, such as shallot, of Oxpoconazole, diniconazole, difenoconazole, cyprocona ginger, garlic and lotus root. Moreover, the pest insect dam Zole, tetraconazole, tebuconazole, triadimenol, triadimefon, 50 age control by application to these plant seeds and plant triticonazole, bitertanol, fenbuconazole, fluguinconazole, bodies is not only related to these seeds, seed tubers, and seed flusilaZole, flutriafol, prothioconazole, propiconazole, bro bulbs themselves, but also to the products such as stems, muconazole, hexaconazole, penconazole, metconazole, and leaves, fruits and the like that grow therefrom. fluguinconazole; The plant seeds and plant bodies in this specification may copper fungicides, such as copper, copper nonylphenolsul 55 also be plant seeds, cereals, legumes, vegetables, and flower fonate, basic copper oxychloride, basic copper Sulphate, ing plants which have undergone genetic transformation, in oxine copper, DBEDC, anhydrous copper Sulfate, and copper other words, plants that do not initially exist in nature but are II hydroxide: produced by manipulating genes and the like artificially. benzimidazole fungicides. Such as thiophanate-methyl, Examples thereof include, but are not limited to: plants benomyl, thiabendazole, thiophanate, carbendazim, and 60 imparted with herbicide resistance Such as Soya bean, corn, fuberidazole; and cotton; cold adapted plants such as rice and tobacco; and organophosphorus fungicides, such as EDDP, IBP, tolclo plants imparted with the functionality of producing insecti foS-methyl, fosetyl, dinocap, and pyrazophos: cidal Substance, such as corn, cotton, and potato. acylalanine fungicides, such as metalaxyl, oxadixyl, benal Stored cereals, stored legumes, stored fruits, and stored axyl, and metalaxyl-M; 65 Vegetables refer to cereals, legumes, fruits, vegetables, and dicarboximide fungicides, such as iprodione, procymi the like which are stored and saved for domestic distribution done, VincloZolin, and chloZolinate; or export/import, and these are generally provided for con US 8,101,657 B2 13 14 Sumption or processing. Examples that may be given thereof ylene glycol dimethyl ether; alcohols, such as ethanol, pro include, rice, barley, wheat, corn, rye, oat, pea, kidney bean, panol, and ethylene glycol; carbonates, such as ethylene car black-eyed bean, Saltani bean, Saltapia bean, butter bean, bonate, propylene carbonate, and butylene carbonate; aprotic pegia bean, white bean, lima bean, broad bean, Soya bean, Solvents such as dimethylformamide, and dimethyl sulfox aZuki bean, apricot, Japanese plum, cherry, plum, nectarine, ide; and water, and the like. peach, orange, grapefruit, Chinese citron, lime, lemon, Furthermore, in order to reinforce the effect of the inven loquat, quince, apple, avocado, kiwifruit, guava, date, pine tion compound the following adjuvants (binders, disintegra apple, passion fruit, banana, papaya, mango, Strawberry, tors, pH adjusters, antifoams and antifreezing agents) may cranberry, huckleberry, blackberry, blueberry, persimmon, also be used, alone or in combinations thereof, according to watermelon, grape, oriental melon, melon, turnip, cauli 10 flower, cabbage, watercress, kale, horseradish, radish, broc the purpose and in consideration of the form of the formula coli, Sweet potato, konnyaku tubers, taro, potato, Japanese tion, the treatment method and the like. As adjuvants, Surfac pumpkin, cucumber, oriental pickling melon, artichoke, tants may be used that are usually used in agricultural formu endive, burdock, Salsify, chicory, lettuce, Shiitake mushroom, lation for purposes such as emulsification, dispersion, mushroom, celery, carrot, parsnip, parsley, tomato, Sweet 15 spreading, and wetting, and examples that may be given of pepper, asparagus, onion, garlic, Welsh onion, Scallion, green Such surfactants include, but are not limited to: nonionic Soya bean, okra, Sugar cane, ginger, Sugar beet, spinach, Surfactants such as Sorbitan fatty acid esters, polyoxyethylene immature kidney beans, immature peas, oilseeds (such as Sorbitan fatty acid esters, Sucrose fatty acid esters, polyoxy sesame seeds, Sunflower seeds, oilseed rape, safflower seeds, ethylene fatty acid esters, polyoxyethylene resin acid esters, and cotton seeds), nuts (such as almond, ginkgo nut, chestnut, polyoxyethylene fatty acid diesters, polyoxyethylene castor walnut, and pecan), cacao bean, coffee bean, tea, and hops. oils, polyoxyethylene alkyl ethers, polyoxyethylene alkyl Silage refers to feed and the like that is stored and saved for phenyl ethers, polyoxyethylene dialkyl phenyl ethers, form domestic distribution or export/import, and is generally pro aldehyde condensates of polyoxyethylene alkyl phenyl ether, vided for the breeding of livestock and the like. Specific polyoxyethylene-polyoxypropylene block polymer, alkyl examples that may be given thereof include cereals, legumes, 25 polyoxyethylene-polyoxypropylene block polymer ether, and the like. alkylphenyl polyoxyethylene-polyoxypropylene block poly Stored flowering plants refers to potted plants, flower mer ether, polyoxyethylene alkylamine, polyoxyethylene arrangements, cut flowers, bulbs, seeds, and the like stocked fatty acid amide, polyoxyethylene bisphenyl ether, polyoxy for domestic distribution or export/import, and are mainly alkylene benzylphenyl ether, polyoxyalkylene styryl phenyl provided for decoration and cultivation. Examples that may 30 ether, polyoxyalkylene adducts of a higher alcohol, polyoxy be given thereof include, orchid, Rumohra, chrysanthemum, ethylene ethers, ester modified silicones, and fluorosurfac xerophyllum, Eurya japonica, lily, freesia, wild pink, rose, tants; anionic surfactants such as alkyl sulfates, polyoxyeth anthurium, carnation, tulip and the like. ylene diallyl ether sulfates, polyoxyethylene alkyl ether Export/import timber refers to logs or sawn timbers that are Sulfates, polyoxyethylene alkylphenyl ether Sulfates, poly stored/stockpiled for the purpose of export/import, and is 35 oxyethylene benzylphenyl ether sulfates, polyoxyethylene generally provided for processing, construction, and the like. styryl phenyl ether Sulfates, polyoxyethylene-polyoxypropy Examples that may be given thereof include hemlock, Dou lene block polymer Sulfates, paraffin Sulfonates, alkane Sul glas fir, spruce, Picea jezoensis, Abies Sachalinensis, larch, fonates, AOS, dialkyl sulfosuccinate, alkylbenzene sul lauan, and the like. fonates, naphthalene Sulfonates, dialkyl naphthalene The content of the dinotefuranas an active ingredient of the 40 Sulfonates, formaldehyde condensates of naphthalene Sul composition of the invention is normally in the range of fonates, alkyl diphenyl ether disulfonates, lignin Sulfonates, 0.005% to 99% with respect to the total weight of the com polyoxyethylene alkyl phenyl ether Sulfonates, polyoxyeth position, preferably is 0.01% to 90%, and is still more pref ylene alkyl ether SulfoSuccinate half esters, fatty acid salts, erably 0.1% to 85%. On the other hand, the content of the N-methyl fatty acid sarcosinate, resinates, polyoxyethylene fungicidal compound is normally in the range of 0.005% to 45 alkyl ether phosphates, polyoxyethylene phenyl ether phos 99% with respect to the total weight of the composition, phates, polyoxyethylene dialkyl phenyl ether phosphates, preferably is 0.01% to 90%, and still more preferably is 0.1% polyoxyethylene benzylated phenyl ether phosphates, poly to 85%. The total content of dinotefuran together with other oxyethylene benzylated phenylphenyl ether phosphates, fungicidal compound(s) is normally in the range of 0.005% to polyoxyethylene Styrylated phenyl ether phosphates, poly 99% with respect to the total weight of the composition, 50 oxyethylene benzylated phenylphenyl ether phosphates, preferably is 0.01% to 90%, and is still more preferably 0.1% polyoxyethylene-polyoxypropylene block polymer phos to 85%. phates, polyoxyethylene diallyl ether Sulfates, phosphatidyl A carrier used for the above formulation is not particularly choline, phosphatidyl ethanolimine, alkyl phosphates and limited, and if it is a carrier that is usually used for agricultural Sodium tripolyphosphates; polyanion type high molecular formulation, then eithera solid or a liquid carrier may be used. 55 surfactant derived from acrylic acid with acrylonitrile, acry As a Solid carrier, the following may be given as examples: lamide-methylpropanesulfonic acid; cationic Surfactants, inorganic Substances, such as bentonite, montmorillonite, Such as alkyl trimethyl ammonium chloride, methyl polyoxy kaolinite, diatomaceous earth, white clay, talc, clay, Vermicu ethylene alkyl ammonium chloride, alkyl N-methylpyri lite, gypsum, calcium carbonate, amorphous silica, ammo dinium bromide, mono-methylated ammonium chloride, nium sulfate; vegetable organic Substance. Such as Soya bean 60 dialkyl methalated ammonium chloride, alkyl pentamethyl flour, wood flour, saw dust, wheat flour, lactose, Sucrose, and propylene amine dichloride, alkyl dimethyl benzalkonium glucose; and urea and the like. As a liquid carrier, the follow chloride, and benzethonium chloride; and amphoteric Surfac ing may be given as examples: aromatic hydrocarbons such as tants, such as dialkyl diaminoethyl betaines and alkyl dim toluene, Xylene, and cumene, and naphthenes; paraffin hydro ethylbenzyl betaine. carbons, such as n-paraffin, iso-paraffin, liquid paraffin, kero 65 As a binder, examples that may be given include Sodium sene, mineral oil, and polybutene; ketones, such as acetone, arginate, polyvinyl alcohols, gum arabic, sodium CMC, ben and methyl ethyl ketone; ethers, such as dioxane and dieth tonite, and the like. US 8,101,657 B2 15 16 Examples that may be given of disintegrants include of diatomaceous earth were mixed together and ground, and Sodium CMC, crosscarmellose sodium, and examples of sta a wettable powder containing dinotefuran at 40% and flusul bilizers include hindered phenol based antioxidants, benzot famide at 4% was obtained. riazol based and hindered amine based ultraviolet absorbers, and the like. Example 3 Phosphoric acid, acetic acid, and sodium hydroxide may be used as a pH adjuster, and industrial fungicides and antifungal Wettable Powder agents, such as 1,2-benzisothiazolin-3-one and the like, may be added for prevention of bacteria and molds. 10 70 parts of dinotefuran, 4 parts of flusulfamide, 1 part of As a thickener, Xanthane gum, guar gum, Sodium CMC, Sodium ligninsulfonate, 5 parts of white carbon, and 20 parts gum arabic, polyvinyl alcohols, montmorillonite, and the like of diatomaceous earth were mixed together and ground, and may also be used. a wettable powder containing dinotefuran at 70% and flusul As required, silicone compounds may be used as antifoam famide at 4% was obtained. ing agents and propylene glycol, ethylene glycol, and the like 15 may be used as antifreezing agents. Example 4 When applying the composition of the invention to plant seeds, plant seeds may be immersed in a composition as it is. Alternatively, the composition may be diluted to a suitable Wettable Powder concentration with a suitable carrier, and then used by immer Sion, dust coating, spraying, coating treatment, or the like, to 70 parts of dinotefuran, 4 parts of hymexazol, 1 part of plant seeds. Sodium ligninsulfonate, 5 parts of white carbon, and 20 parts There are no particular limitations to Suitable carriers, and of diatomaceous earth were mixed together and ground, and examples that may be given thereof include: liquid carriers, a wettable powder containing dinotefuranat 70% and hymex Such as water or organic solvents such as ethanol; Solid car 25 azol at 4% was obtained. riers, such as inorganic Substances like bentonite, montmo rillonite, kaolinite, diatomaceous earth, white clay, talc, clay, Example 5 Vermiculite, gypsum, calcium carbonate, amorphous silica, and ammonium sulfate; vegetable organic Substances, such as Wettable Powder Soya bean flour, wood flour, saw dust, wheat flour, lactose, 30 Sucrose, and glucose; and urea. 70 parts of dinotefuran, 4 parts of flusulfamide, 4 parts of The dilution rate of formulation may be set appropriately, hymexaZol. 1 part of sodium ligninsulfonate, 5 parts of white and the dilution rate is suitably chosen according to the can carbon, and 16 parts of diatomaceous earth were mixed didate crop for application, type of disease damage, and type 35 together and ground, and a wettable powder containing of insect damage, and the dilution rate is suitably 1 to 50,000 dinotefuran at 70%, flusulfamide at 4% and hymexazol at 4% times, is preferably 1 to 20,000 times, and is still more pref was obtained. erably 1 to 10,000 times. For carrying out dust coating, spraying, and coating treat Reference Example 1 ment, a suitable amount of the formulation used is usually 40 about 0.05% to 50% of dry plant seed weight, more preferably 0.1% to 40%, and still more preferably 0.1% to 30%. How Wettable Powder ever, the amount used is not limited to these ranges, and may be varied according to the form of the formulation and to the 70 parts of dinotefuran, 1 part of sodium ligninsulfonate, 5 kind of plant seed used as the candidate for treatment. 45 parts of white carbon, and 24 parts of diatomaceous earth were mixed together and ground, and a wettable powder EXAMPLES containing dinotefuran at 70% was obtained. The invention will now be explained in detail, with refer Reference Example 2 ence to Examples and Test Examples. 50 Example 1 Wettable Powder

Powder Formulation 4 parts of flusulfamide, 1 part of sodium ligninsulfonate, 5 55 parts of white carbon, and 90 parts of diatomaceous earth 1 part of dinotefuran, 10 parts of hymexazol, 88.5 parts of were mixed together and ground, and a wettable powder clay, and 0.5 parts of DRILESSB (trade name, an aggregating containing flusulfamide at 4% was obtained. agent from Sankyo Co., Ltd.) were uniformly mixed together and ground, and a powderformulation containing dinotefuran Reference Example 3 at 1% and hymexazol at 10% was obtained. 60 Example 2 Wettable Powder Wettable Powder 4 parts of hymexaZol. 1 part of sodium ligninsulfonate, 5 65 parts of white carbon, and 90 parts of diatomaceous earth 40 parts of dinotefuran, 4 parts of flusulfamide, 1 part of were mixed together and ground, and a wettable powder sodium ligninsulfonate, 5 parts of white carbon, and 50 parts containing hymexazol at 4% was obtained. US 8,101,657 B2 17 18 Reference Example 4 ether Sulfate, 0.2 parts of silicone antifoaming agent, and 64.8 parts of water, and a flowable containing dinotefuran at 20% Wettable Powder was obtained. Reference Example 6 4 parts of flusulfamide, 4 parts of hymexazol, 1 part of Sodium ligninsulfonate, 5 parts of white carbon, and 88 parts of diatomaceous earth were mixed together and ground, and Flowable a wettable powder containing flusulfamide at 4% and hymex azol at 4% was obtained. 10 Wetgrinding was performed using a sandgrinder on 4 parts of flusulfamide, 5 parts of propylene glycol, 5 parts of poly Example 6 oxyethylene oleate, 5 parts of polyoxyethylene diallyl ether Sulfate, 0.2 parts of silicone antifoaming agent, and 80.8 parts Emulsion 15 of water, and a flowable containing flusulfamide at 4% was obtained. 15 parts of dinotefuran, 15 parts of triflumizole, 10 parts of Reference Example 7 cyclohexane, 40 parts of xylene, and 20 parts of SORPOL (trade name, a surfactant made by Toho Chemical Industries Flowable Co., Ltd.) were uniformly dissolved and mixed, and an emul sion containing dinotefuran at 15% and triflumizole at 15% Wetgrinding was performed using a sandgrinder on 4 parts was obtained. of hymexaZol. 5 parts of propylene glycol, 5 parts of poly 25 oxyethylene oleate, 5 parts of polyoxyethylene diallyl ether Example 7 Sulfate, 0.2 parts of silicone antifoaming agent, and 80.8 parts of water, and a flowable containing hymexazol at 4% was Granular Wettable Powder obtained. 20 parts of dinotefuran, 50 parts of benomyl, 3 parts of 30 Test Example 1 sodium CMC, 5 parts of sodium alkylsulfate, and 22 parts of clay were uniformly mixed, and then kneading with water, Control Effect Against Sugar Beet Seedling pelletization, drying, and particle size regulation were per Damping Off formed thereto, and a granular wettable powder containing dinotefuran at 20% and benomyl at 50% was obtained. 35 A Rhizoctonia culture and a Pythium culture were sepa rately cultivated at 25° C. for seven days in a wheat bran Example 8 medium, and after respectively grinding, the Rhizoctonia cul ture and/or the Pythium culture were added to and mixed in Flowable with sterilized soil, and the mixtures were filled in plastic pots 40 to obtain infected soils each containing: Wet grinding was performed using a sand grinder on 20 Rhizoctonia culture at 0.1% with respect to the sterilized parts of dinotefuran, 4 parts of flusulfamide, 5 parts of pro pylene glycol. 5 parts of polyoxyethylene oleate, 5 parts of soil; polyoxyethylene diallyl ether sulfate, 0.2 parts of silicone Pythium culture at 0.1% with respect to the sterilized soil, antifoaming agent, and 60.8 parts of water, and a flowable 45 and containing dinotefuran at 20% and flusulfamide at 4% was Rhizoctonia culture at 0.1% and Pythium culture at 0.1%, obtained. with respect to the sterilized soil. Subsequently, amounts of 3.5% and 7% per kg of seed of Example 9 the powder of Example 1 containing active ingredients of 50 dinotefuran and hymexazol, and amounts of 0.5% and 1.0% Flowable per kg of seed of a commercially available seed fungicide (TACHIGAREN, a dust coating agent containing hymexazol Wet grinding was performed using a sand grinder on 20 made by Sankyo Agro Co., Ltd.) were added to Sugar beet parts of dinotefuran, 4 parts of hymexaZol. 5 parts of propy seed (variety: ABEND), and well mixed. The sugar beet seeds lene glycol, 5 parts of polyoxyethylene oleate, 5 parts of 55 to which chemical treatment had been carried out were sown polyoxyethylene diallyl ether sulfate, 0.2 parts of silicone at five seeds per pot, with a total of 20 pots, and these pots antifoaming agent, and 60.8 parts of water, and a flowable were grown on in agreenhouse. The number of non-sprouting containing dinotefuran at 20% and hymexazol at 4% was seeds was examined at 7 days after sowing, and the seedling obtained. dieback number was examined at 14 days after sowing, with 60 the naked eye, and the seedling dieback rate was computed by Reference Example 5 the following Formula 1. Moreover, the existence or not of occurrences of phytotoxicity was also examined with the Flowable naked eye. Results are shown in Table 1. Wet grinding was performed using a sand grinder on 20 65 Seedling dieback rate ((number of non-sprouting parts of dinotefuran, 5 parts of propylene glycol, 5 parts of seeds--seedling dieback number), number of polyoxyethylene oleate, 5 parts of polyoxyethylene diallyl seeds sown)x100 Formula 1 US 8,101,657 B2 19 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

Test Example 2 Test Example 3 Control Effect Against Common Scab and Black Scarf in Potato Control Effect Against Bakanae Disease A Rhizoctonia culture was cultivated in a concrete pot in a Rice seeds (variety: Tanginbozu-dwarf) infected with wheat bran medium at 25°C. for seven days, and this was then benomyl-resistant Bakanae disease was mixed respectively added at 0.1% by weight with respect to steam sterilized soil with the emulsion produced in Example 6 containing dinote and mixed in uniformly. A Rhizoctonia culture cultivated by furan and triflumizole as active ingredients, and mixed with a the same method was added at 0.1% with respect to soil 25 commercially available seed disinfectant (TRIFMIN, trade extracted from a common scab infected field and mixed in name, a wettable powder containing triflumizole made by uniformly, and soil was also extracted from a common Scab Nippon Soda Co., Ltd.) as a control chemical, and a dressing infected field. These three soil compositions were placed, treatment was carried out. After soaking the seeds (at 15° C. respectively, into concrete pots (50 cm lengthx50 cm width:X for three days) and forced sprouting (at 28°C. for one day), 30 the seeds to which chemical treatment had been carried out 30 cm depth) and the test soils were thereby obtained. were each sown at 100 seeds per plastic pot, and grown on in Next, after carrying out dip treatment of the seed tubers of a greenhouse. The existence of disease onset was examined potato (variety: Baron) into, respectively, 50 times diluents of for all the seedlings with the naked eye at 20 days after the wettable powder produced in Example 2 and in Reference Sowing, and the disease onset seedling ratio was computed by Example 2 (comparative agents), and of a commercial fungi the following Formula 3. Moreover, the existence or not of cide (NOTTOBAN, a wettable powder containing tolclofos 35 occurrences of phytotoxicity was also examined with the methyl and flusulfamide, made by Sumitomo Chemical Co., naked eye. Three replicates of the above test were performed, Ltd.), the seed tubers were air dried and then two seed tubers and the average values of the results are shown in Table 3. were buried perpot. For the non-treated category, seed tubers that had not undergone chemical treatment were buried. 110 Disease onset seedling ratio=(number of diseased days afterburying the seed tubers, the newly formed potatoes 40 seedlings/number of seeds sown)x100 Formula 3 were dug up, and the existence of disease onset was examined TABLE 3 with the naked eye, and the disease onset potato ratio was Active ingredient Disease onset computed by the following Formula 2. Five replicates of the amount Seedling ratio above test were performed, and the average values of the Test compound (g/kg seed) (%) Phytotoxicity 45 results are shown in Table 2. Emulsion of the Dinotefuran 5.0 + 32.4 None Disease onset potato ratio=(number of potatoes with invention Trifumizole 5.0 disease onset/total number of potatoes exam (Example 6) ined)x100 Formula 2 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 US 8,101,657 B2 21 22 TABLE 3-continued Wettable powder: 65 g and 130 g of formulation/unit (one unit is 100,000 of sugar beet seeds). Active ingredient Disease onset Gaucho (imidacloprid): 130 g formulation/unit. amount Seedling ratio On the next day of treatment, the test seeds were sown at 50 Test compound (g/kg seed) (%) Phytotoxicity seeds each, in a concrete pot filled with soil (5 m lengthx2 m Control seed Trifumizole 5.0 41.5 None width:X60 cm depth). disinfectant The level of insect damage by striped flea beetle was inves TRIFMIN emulsion tigated at 45 days after Sowing and at 60 days after Sowing, No treatment 45.3 and the prevention index was computed by the following 10 formula 5. Moreover, the existence or not of occurrences of phytotoxicity was also examined with the naked eye. Test Example 4 Results are shown in Table 5. The index number levels of insect damage areas follows. Control Effect Against Bakanae Disease in Rice Index 0: No insect damage 15 Index 1: Slight level of insect damage Rice seeds (variety: Tanginbozu-dwarf) contaminated with Index 2: Medium level of insect damage benomyl-resistant Bakanae disease was mixed respectively Index 3: High level of insect damage with the granular wettable powder produced in Example 7 Prevention index=100-((1xnumber of insect damage containing dinotefuran and benomyl as active ingredients, at index 1+2xnumber of insect damage at index and with a commercially available seed disinfectant (BEN 2+3xnumber of insect damage at index 3)/(3x LATE, trade name, a wettable powder containing benomylas total number of examinations)x100) Formula 5 the active ingredient made by Sumitomo Chemical Co., Ltd.) as a control chemical, and a dressing treatment was carried out. After soaking the seeds (at 15° C. for three days) and TABLE 5 forced sprouting (at 28°C. for one day), the seeds to which 25 Formulation treatment Prevention chemical treatment had been carried out were each sown at amount index 100 seeds per plastic pot, and grown on in a greenhouse. The Test compound (g/unit) (%) Phytotoxicity existence of disease onset was examined for all the seedlings Wettable powder 65g 100 None with the naked eye at 20 days after sowing, and the disease of the invention 30 g 100 None 30 (Example 3) onset seedling ratio was computed by the following Formula Wettable powder 65g 100 None 4. Moreover, the existence or not of occurrences of phytotox of the invention 30 g 100 None icity was also examined with the naked eye. Three replicates (Example 4) of the above test were performed, and the average values of Wettable powder 65g 100 None the results are shown in Table 4. of the invention 30 g 100 None 35 (Example 5) Comparative 65g 88 None Disease onset seedling ratio=(number of diseased wettable powder 30 g 92 None seedlings/number of seeds sown)x100 Formula 4 (Reference Example 1 Comparative 65g O None TABLE 4 wettable powder 30 g O None 40 (Reference Disease Example 2) Active ingredient Onset Comparative 65g O None amount seedling wettable powder 30 g O None Test compound (g/kg seed) ratio (%) Phytotoxicity (Reference Example 3) Granular wettable powder Dinotefuran 2.0 + 29.4 None 45 Comparative 65g O None of the invention Benomyl 5.0 wettable powder 30 g O None (Example 7) (Reference Control seed disinfectant Benomyl 5.0 39.7 None Example 4) BENLATE wettable Contro 30 g 85 None powder insecticide No treatment 45.3 50 Gaucho No treatment O None

Test Example 5 Test Example 6 Control Effect Against Beet Flea Beetle on Sugar 55 Beet Control Effect Against Adzuki Bean Weevil Processing was carried out in a seed dressing machine Coating treatment was carried out using the respective (chemical liquid jetting within a rotating drum) using the flowables produced in Example 8. Example 9, Reference wettable powders produced in Example 3. Example 4. 60 Example 5 (comparative agent), Reference Example 6 (com Example 5, Reference Example 1 (comparative agent), Ref parative agent), and Reference Example 7 (comparative erence Example 2 (comparative agent), Reference Example 3 agent) at a dose of 5, 10 and 20 ml, with respect to 1 kg of (comparative agent) and Reference Example 4 (comparative aZuki bean seed. After air-drying, portions thereof were agent), and with Gaucho (trade name, an insecticide contain moved to 9 cm deep petri dishes, and allowed to stand in a ing imidacloprid made by Bayer CropScience), at the follow 65 constant 25° C. temperature room. Two months and three ing amounts of formulation per 100,000 seed unit of sugar months after the coating treatment, respectively, five male beet seed. adult adzuki bean weevils and five adult female adzuki bean US 8,101,657 B2 23 24 weeviles, ten in total, were grazed per deep petri dish. The B: Damage area is 5 to 10% of the surface area of root number of dead weevils and the number of eggs laid on the C: Damage area is 2 to 4% of the surface area of root aZuki beans were examined two days after grazing, and the mortality was computed by the following Formula 6. Five D: Damage area is 1% of the surface area of root replicates of the above test were performed, and the average values of the results are shown in Table 6. Degree of damage=(number of roots of Ax4+number of roots of Bx3+number of roots of Cx2+number Mortality=(number of dead weevils in treated cat of roots of Dx1+number of roots with no dam egory 50 weevils)x100 Formula 6 agex0)/(number of roots examinedx4)x100 Formula 7 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.O8 (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 (Reference Fusulfamide 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 12.0 (Reference Hymexazol 0.8 O 11.0 O 11.0 Example 7) No treatment — O 11.5 O 10.8

Test Example 7 TABLE 7 40 Control Effect Against Striped Flea Beetle 32 days after 52after days Test chemicals Formulation amount treatinent treatinent Soil surfaces were treated with commercially available STARKLE granule 9 kg/10 a 30 2O formulations at amounts of STARKLE granule + 9 kg/10 a + 2O 13 STARKLE granule (trade name, a granular formulation 45 NEBITINpowder 30 kg/10 a containing 1% dinotefuran made by Sankyo Agro Co., Ltd.) NEBIJIN powder 30 kg/10 a 65 8O at 9 kg/10 a. STARKLE granule + 9 kg/10 a + 18 13 NEBIJIN powder (trade name, a powder formulation con- MNASA I E. 65 88 taining 0.3% flusulfamide made by Sankyo Agro Co., Ltd.) at No treatment 60 70 30 kg/10 a. 50 MONG ARIT granule (trade name, a granular formulation containing 1.5% simeconazole made by Sankyo Agro Co., Ltd.) at 6 kg/10a; The invention claimed is: STARKLE granule and NEBIJIN powder at 9 kg and 30 1. A plant disease and insect damage control composition kg/10a; and 55 comprising active ingredients of (RS)-1-methyl-2-nitro-3- STARKLE granule and MONG ARIT granule at 9 kg and 6 (tetrahydro-3-furylmethyl)guanidine (common name: kg/10a, respectively, and the treated soils were lightly mixed dinotefuran) and at least one fungicidal compound selected with a rake. from the group consisting of 2,4-dichloro-C.C.C.-trifluoro-4'- Immediately after the soil treatment, Japanese radish seeds nitro-m-toluenesulfonanilide (common name: flusulfamide), were sown in lines. The Japanese radishes were dug up at 32 60 days and at 52 days after sowing, respectively, and the dam 3-hydroxy-5-methylisoxazol (common name: hymexaZol), age level to the roots was examined on the following basis, and (RS)-2-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3- and the degree of damage was computed from the following (trimethylsilyl)propan-2-ol (common name: Simeconazole). formula. Results are shown in Table 7. 2. The plant disease and insect damage control composi Damage Level 65 tion according to claim 1, wherein the at least one fungicidal A: Damage area is greater than 11% of the Surface area of compound comprises 2,4-dichloro-C.C.C.-trifluoro-4'-nitro rOOt m-toluenesulfonanilide (common name: flusulfamide). US 8,101,657 B2 25 26 3. The plant disease and insect damage control composi 8. The plant disease and insect damage control method tion according to claim 1, wherein the at least one fungicidal according to claim 6, wherein the method of application to a compound comprises 3-hydroxy-5-methylisoxazol (common stored cereal, stored legume, stored fruit, stored vegetable, name: hymexaZol). silage, stored flowering plants, or export/import timber is 4. The plant disease and insect damage control composi spray treatment, coating treatment, dip treatment, dressing tion according to claim 1, wherein the at least one fungicidal treatment, fumigation treatment, Smoke treatment, or pres compound comprises (RS)-2-(4-fluorophenyl)-1-(1H-1,2,4- Sure injection. triazol-1-yl)-3-(trimethylsilyl)propan-2-ol (common name: 9. Plant seed, stored cereal, stored legume, stored fruit, simeconazole). stored vegetable, silage, stored flowering plant, or export/ 5. The plant disease and insect damage control composi 10 import timber to which the plant disease and insect damage tion according to claim 1, wherein the at least one fungicidal control composition according to claim 1 has been applied. compound comprises a mixed composition of at least two 10. The plant disease and insect damage control method selected from the group consisting of flusulfamide, hymex according to claim 6, wherein the method of application to a aZol, and Simeconazole. plant body or soil is foliar application to a plant body, spray 6. A plant disease and insect damage control method com 15 treatment to the Soil surface, Soil incorporation after spray prising applying the pest control composition according treatment to the Soil Surface, injection treatment into the soil. claim 1 to a plant body, Soil, plant seed, stored cereal, stored or soil drenching treatment. legume, stored fruit, stored vegetable, silage, stored flowering 11. A method of controlling plant disease and insect dam plant, or export/import timber. age to a plant body grown from a plant seed, the method 7. The plant disease and insect damage control method comprising applying, to the plant seed, the plant disease and according to claim 6, wherein the method of application to insect damage control composition according to claim 1. plant seeds is spray treatment, coating treatment, dip treat ment, or dressing treatment of seeds. k k k k k