(12) United States Patent (10) Patent No.: US 8.258,103 B2 Araki Et Al

USOO82581 03B2

(12) United States Patent (10) Patent No.: US 8.258,103 B2 Araki et al. (45) Date of Patent: Sep. 4, 2012

(54) PESTICIDAL COMPOSITION JP 2006-50961 A 2, 2006 JP 2006-517538 A T 2006 (75) Inventors: Tsutomu Araki, Fukuchiyama (JP); WO WO-9700265 A1 1, 1997 Naoki Sato, Yachiyo (JP) OTHER PUBLICATIONS (73) Assignee: Sumitomo Chemical Company, “Insecticidal combinations containing alkoxylated amines' Limited, Tokyo (JP) Research Disclosure, Jan. 2006, No. 501, pp. 18-19, Disclosed Anonymously. (*) Notice: Subject to any disclaimer, the term of this International Preliminary Report on Patentability (Form PCT/IB/ patent is extended or adjusted under 35 373) and Written Opinion of the International Searching Authority U.S.C. 154(b) by 182 days. (Form PCT/ISA/237) issued in PCT/JP2008/062591 (dated Feb. 9, 2010). (21) Appl. No.: 12/668,625 Primary Examiner — Elli Peselev (22) PCT Filed: Jul. 11, 2008 (74) Attorney, Agent, or Firm — Birch, Stewart, Kolasch & (86). PCT No.: PCT/UP2008/062591 Birch, LLP S371 (c)(1), (2), (4) Date: Jan. 11, 2010 (57) ABSTRACT The present invention provides a pesticidal composition com (87) PCT Pub. No.: WO2009/008506 prising a compound represented by the formula (I): PCT Pub. Date: Jan. 15, 2009 (65) Prior Publication Data US 2010/O184713 A1 Jul. 22, 2010 (30) Foreign Application Priority Data Jul. 12, 2007 (JP) ...... 2007-182986 May 20, 2008 (JP) ...... 2008-1316O7 (51) Int. Cl. A6 IK3I/70 (2006.01) (52) U.S. Cl...... S14/28 (58) Field of Classification Search ...... 514/28 See application file for complete search history. wherein A, B, R. R. R. R. R. Rs. Re and R7 are as defined (56) References Cited in the description, and 2,6-dichloro-4-(3.3-dichloroallyloxy) phenyl 3-5-(trifluoromethyl)-2-pyridyloxypropyl ether as U.S. PATENT DOCUMENTS active ingredients, and also provides a pest control method 5,202,242 A 4/1993 Mynderse et al. which comprises the step of applying an effective amount of 5,922,880 A 7, 1999 Sakamoto et al. the compound represented by the above formula (I) and an 2006.0128642 A1 6, 2006 Malsam et al. effective amount of 2,6-dichloro-4-(3.3-dichloroallyloxy) phenyl 3-5-(trifluoromethyl)-2-pyridyloxypropyl ether to FOREIGN PATENT DOCUMENTS pests or a place where pests inhabit. JP 6-506477 A T 1994 JP 9-151172 A 6, 1997 JP 11-5061-17 A 6, 1999 4 Claims, No Drawings US 8,258,103 B2 1. 2 PESTCDAL COMPOSITION R represents a group represented by the formula (II):

TECHNICAL FIELD (II) R8 The present invention relates to a pesticidal composition 5 and so on.

BACKGROUND ART (wherein Rs and R, independently represent a C1-C4 alkyl Hitherto, various pesticidal compositions for controlling 10 group, a C1-C4 haloalkyl group, a C1-C4 alkanoyl group or a pests have been developed and used practically (see Patent protected amino group), or a group represented by the for Documents 1 to 3). However, conventional pesticidal compo mula (III): sitions do not exert a satisfactory controlling effect in some cases, and therefore, there is still a need for development of a Rio O— (III) pesticidal composition having an excellent controlling effect. 15 Patent Document 1: WO 97700265 (wherein Rio represents a C1-C4 alkyl group, a C1-C4 Patent Document 2: JP-A 9-151172 haloalkyl group, a C1-C4 alkanoyl group or a protected Patent Document 3: WO 93/09126 amino group), R represents a hydrogen atom or a methyl group, DISCLOSURE OF THE INVENTION R. R. and R independently represent a C1-C4 alkyl group, a C1-C4 haloalkyl group, a C1-C4 alkanoyl group or a Problems to be Solved by the Invention protected hydroxyl group, Rs represents a hydrogen atom, a C1-C4 alkyl group, a An object of the present invention is to provide a pesticidal C1-C4 alkylamino group or an alkylhydroxylamino group composition having an excellent controlling effect against 25 pests. represented by the formula (IV):

Means for Solving the Problems (IV) R-O-N- The present inventors found that a pesticidal composition 30 comprising a compound represented by the following for R11 mula (I) and 2,6-dichloro-4-(3.3-dichloroallyloxy)phenyl 3-5-(trifluoromethyl)-2-pyridyloxypropyl ether as active (wherein R and R2 independently represent a hydrogen ingredients could exert a greater effect in pest control as atom, a C1-C4 alkyl group or a C1-C5 alkanoyl group), compared with a single application of each compounds, and 35 thus the present invention was completed. R represents a hydrogen atom or methyl group, and R7 represents a methyl group or an ethyl group; and 2.6- Effect of the Invention dichloro-4-(3.3-dichloroallyloxy)phenyl 3-5-(trifluorom ethyl)-2-pyridyloxypropyl ether as active ingredients; According to the present invention, a pesticidal composi 40 (2) The composition according to the above (1), wherein A is tion having an excellent controlling effect against pests and so a single bond or a double bond, on are provided. B is a double bond, BEST MODE FOR CARRYING OUT THE R is a group represented by the formula (II): INVENTION 45 (II) The present invention provides: R8 (1) A pesticidal composition comprising a compound repre sented by the formula (I): 50 (wherein Rs and R are methyl groups), R is a methyl group,

55 R is a methyl group or an ethyl group, R is a methyl group, Rs is a hydrogen atom, R is a methyl group, and R, is an ethyl group; 60 (3) The composition according to the above (2), wherein R is an ethyl group; (4) The composition according to the above (1), wherein the compound represented by the formula (I) is spinetoram; 65 (5) A pest control method which comprises a step of applying wherein A and B independently represent a single bond, a an effective amount of a compound represented by the for double bond or an ether linkage, mula (I): US 8,258,103 B2 4 The compound represented by the above formula (I) may be referred to as “the present compound 1’, and 2,6-dichloro 4-(3,3-dichloroallyloxy)phenyl 3-5-(trifluoromethyl)-2-py ridyloxypropyl ether may be referred to as “the present com pound 2'. The present compound 1 and the present compound 2 may be collectively referred to as “the presentactive ingre dients'. The composition having characteristics described in the above (1) may be referred to as “the composition of the present invention'. The present compound 1 is disclosed in WO97/00265. The 10 present compound 2 (generic name: pyridalyl) is disclosed in JP-A9-151172. For the present compound 1, the “C1-C4 alkyl group' means an alkyl group of 1 to 4 carbon atoms, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobu tyl, sec-butyl and tert-butyl. 15 The “C1-C4 haloalkyl group” means an alkyl group of 1 to wherein A and B independently represent a single bond, a 4 carbonatoms which is Substituted with at least one halogen double bond or an ether linkage, atom (e.g., fluorine, chlorine, bromine or iodine), and R represents a group represented by the formula (II): examples thereof include chloromethyl, difluoromethyl, trichloromethyl, trifluoromethyl, 2-bromoethyl, 2.2.2-trif (II) luoroethyl, 1.1.2.2.2-pentafluoroethyl, 3,3,3-trifluoropropyl Js and 4,4,4-trifluorobutyl. N The “C1-C4 alkanoyl group” means an alkanoyl group of 1 R1 \ to 4 carbon atoms, and examples thereof include formyl. acetyl, 2-methylacetyl, 2,2-dimethylacetyl, propionyl, (wherein Rs and R independently represent a C1-C4 alkyl butyryl and isobutyryl. group, a C1-C4 haloalkyl group, a C1-C4 alkanoyl group or a 25 The “protected hydroxyl group” means a hydroxyl group protected amino group), or a group represented by the for protected with a protecting group, and examples of the pro mula (III): tecting group include those described in “Protective Groups Rio O— (III) in Organic Synthesis'.T.W. Greene and P. G. M. Wuts, ed. 3, John Wiley & Sons, New York, 1999 and references cited (wherein Rio represents a C1-C4 alkyl group, a C1-C4 therein. haloalkyl group, a C1-C4 alkanoyl group or a protected 30 The “protected amino group” means an amino group pro amino group), tected with a protecting group, and examples of the protecting R represents a hydrogen atom or a methyl group, group include those described in the above “Protective R. R. and R independently represent a C1-C4 alkyl Groups in Organic Synthesis' and references cited therein. group, a C1-C4 haloalkyl group, a C1-C4 alkanoyl group or a The "C1-C4 alkylamino group” means an alkylamino protected hydroxyl group, 35 group of 1 to 4 carbon atoms, and examples thereof include Rs represents a hydrogen atom, a C1-C4 alkyl group, a methylamino, ethylamino, propylamino, isopropylamino, C1-C4 alkylamino group or an alkylhydroxylamino group butylamino, isobutylamino, Sec-butylamino and tert-buty represented by the formula (IV): lamino. (IV) The “C1-C5 alkanoyl group” means an alkanoyl group of 1 R-O-N- to 5 carbon atoms, and examples thereof include formyl. 40 acetyl, 2-methylacetyl, 2,2-dimethylacetyl, propionyl, R11 butyryl, isobutyryl, pentanoyl and 2,2-dimethylpropionyl. The present compound 1 may be present as an isomer (wherein R and R independently represent a hydrogen including a tautomer and a stereoisomer based on an asym atom, a C1-C4 alkyl group or a C1-C5 alkanoyl group), 45 metric carbon atom and a double bond (optical isomer, geo R represents a hydrogen atom or methyl group, and metric isomer, etc.). In the present invention, the compound R7 represents a methyl group or an ethyl group; and an represented by the formula (I) includes all of these isomers effective amount of 2,6-dichloro-4-(3.3-dichloroallyloxy) and mixtures thereof. phenyl 3-5-(trifluoromethyl)-2-pyridyloxypropyl ether to The present compound 1 may be: pests or a place where pests inhabit; and so on. (1) a mixture of a compound represented by the formula (Ia): (Ia)

(R)

CH3 US 8,258,103 B2 5 6 wherein A is a double bond, R is a hydrogen atom and R is Examples of the pharmaceutical additive that may be con a methyl group (hereinafter, referred to as “the compound tained in the present formulation include a Surfactant, a Ala'), and binder, a dispersant, a thickener, a stabilizer, an antioxidant, a a compound represented by the above formula (Ia) wherein A propellant, a defoaming agent, a rust preventive, an antifreez is a double bond, R is a methyl group and R is a methyl ing agent, a dye, and a pigment. Examples of the Surfactant group (hereinafter, referred to as “the compound Alb”), or include alkylsulfate salts, alkylsulfonate salts, alkylaryl Sul (2) a mixture of a compound represented by the above for fonate salts, alkyl aryl ethers and their polyoxyethylenated mula (Ia) wherein A is a single bond, R is a hydrogen atom derivatives, polyethylene glycol ethers, polyhydric alcohol and R is an ethyl group (hereinafter, referred to as “the esters, and Sugar alcohol derivatives. 10 Other examples of the pharmaceutical additive include compound Bla'), and casein, gelatin, polysaccharides (starch, gum arabic, cellulose a compound represented by the above formula (Ia) wherein A derivatives, alginic acid, etc.), lignin derivatives, bentonite, is a double bond, R is a methyl group and R is an ethyl group saccharides, synthetic water-soluble polymers (polyvinyl (hereinafter, described as “the compound B1b). alcohol, polyvinyl pyrrolidone, polyacrylic acid, etc.), PAP Particularly, the mixture (1) of the compound A1a and the 15 (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-meth compound Alb is known as the generic name of spinosad. ylphenol). BHA (a mixture of 2-tert-butyl-4-methoxyphenol The mixture (2) of the compound B1a and the compound Bib and 3-tert-butyl-4-methoxyphenol), fatty acids, andfatty acid is known as the generic name of spinetoram. esterS. The composition of the present invention may be in the The present formulation contains usually 0.001 to 50% by form of a composition consisting of only the present active weight, preferably 0.01 to 30% by weight of the pharmaceu ingredients, or may be in the form of a formulation prepared tical additive. by combining the present active ingredients with other ingre The aerosol formulation is prepared, for example, by dients, such as a liquid formulation, e.g. an oil solution, an charging a container having a jet System, Such as a spray can, emulsifiable concentrate, a flowable formulation and an aero with a formulation containing the present active ingredients Sol formulation, a solid formulation, e.g. a wettable powder, a 25 in the form of an oil solution, an emulsifiable concentrate, a resinformulation, a granule, a dust, a poisonbait and a micro flowable formulation or the like together with a propellant. capsule formulation, a Smoking formulation, a fumigant, an The poison bait is prepared by mixing a base material, the ULV formulation, a spot-on formulation, or a shampoo for present active ingredients and other ingredients. mulation. Hereinafter, a formulation containing the present Examples of the base material for the poison bait include a active ingredients may be referred to as “the present formu 30 food ingredient Such as cereal powder, vegetable oil, Sugar lation'. and crystalline cellulose, an antioxidant such as dibutylhy The present formulation is prepared by a general method droxytoluene and nordihydroguaiaretic acid, a preservative which comprises Supporting, dissolving or dispersing the Such as dehydroacetic acid, an agent for preventing children present active ingredients on/in a carrier appropriately and pets from eating the poison bait by mistake such as hot selected from carriers including a solid carrier, a liquid carrier 35 pepper powder, a pest-attractive perfume Such as cheese per and a gaseous carrier depending on the form of the formula fume, onion perfume and peanut oil. tion, and adding some pharmaceutical additives as needed. The present formulation is applied to a plant or soil where The present formulation contains usually 0.01 to 90% by pests inhabit by Such a method that the present active ingre weight, preferably 0.1 to 80% by weight of the presentactive dients can be provided in an amount effective for pest control. ingredients. 40 In the case of the present formulation in the form of a wettable The weight ratio of the present compound 1 to the present powder, an emulsifiable concentrate, a flowable formulation, compound 2 in the presentactive ingredients is from 100:1 to an aerosol formulation or a dust, examples of an application 1:100, preferably from 10:1 to 1:10. method include spraying of the present formulation or, if Examples of the solid carrier that may be contained in the needed, a dilution thereof with water oran organic solvent on present formulation include finely-divided powder and gran 45 the leaves and stems of a plant where pests inhabit; spraying ules of clay (kaolin clay, diatomaceous earth, synthetic of the present formulation or a dilution thereof on soil near a hydrated siliconoxide, bentonite, agalmatolite clay, acid clay, plant where pests inhabit or soil where pests inhabit; and talc, etc.), ceramics, other inorganic minerals (sericite, drenching of soil near a plant where pests inhabit or soil quartz, Sulfur, calcium carbonate, hydrated silica, etc.), acti where pests inhabit with the present formulation or a dilution vated carbon, and chemical fertilizers (ammonium Sulfate, 50 thereof. In the case of the present formulation in the form of ammonium phosphate, ammonium nitrate, urea, ammonium a poisonbait or a granule, examples of an application method chloride, etc.). include sprinkling of the present formulation on Soil near a Examples of the liquid carrier include water, alcohols plant where pests inhabit or soil where pests inhabit; and (methanol, ethanol, etc.), ketones (acetone, methyl ethyl drenching of soil near a plant where pests inhabit or soil ketone, etc.), aromatic hydrocarbons (benzene, toluene, 55 where pests inhabit with the present formulation. Xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic Examples of an organic solvent used for dilution of the oil hydrocarbons (hexane, kerosene, light oil, etc.), alicyclic Solution include mineral oils (naphthalene, kerosene, diesel hydrocarbons (cyclohexane, etc.), esters (ethyl acetate, butyl oil, etc.) and vegetable oils (soybean oil, cottonseed oil, etc.). acetate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), Examples of a place where agricultural pests inhabit to be ethers (diisopropyl ether, dioxane, etc.), acid amides (N.N- 60 controlled according to the present invention include the foli dimethylformamide, N,N-dimethylacetamide, etc.), haloge age, flowers, buds and roots of plants such as farm crops; the nated hydrocarbons (dichloromethane, trichloromethane, soil and waterside near plants; forests, rangelands, grass carbon tetrachloride, etc.), dimethylsulfoxide, and vegetable lands, houses, and barns. oils (soybean oil, cotton seed oil, etc.). The pest control method of the present invention comprises Examples of the gaseous carrier include fluorocarbon, 65 the step of applying an effective amount of the present active butane gas, LPG (liquefied petroleum gas), dimethyl ether, ingredients to pests or a place where pests inhabit (a plant and carbon dioxide gas. body, Soil, the inside of a house, an animal body, etc.). The US 8,258,103 B2 7 8 present compound 1 and the compound 2, which are the ment, overall soil incorporation treatment, water Surface present active ingredients, may be applied separately, or a spray treatment, foliar spray treatment in a growing period, mixture of the present compound 1 and the compound 2 may flower cluster spray treatment, and water Surface spray treat be applied. ment. Examples of a method of applying the presentactive ingre The seed treatment is a treatment method comprising dients include spray treatment with a liquid formulation, applying the active ingredient directly to or around the seed, drenching treatment with a liquid formulation, spray treat seed tuber or bulb of a crop to be protected from damage such ment with a dust, spray treatment with a granule, Soil incor as ingestion by pests. Specific examples thereof include spray poration treatment with a granule, seed treatment, water cul treatment, spray coating treatment, immersion treatment, ture medium treatment, fumigation treatment, and 10 impregnation treatment, film coating treatment, and pellet transpiration treatment. coating treatment. The spray treatment with a liquid formulation is a treat The water culture medium treatment is a treating method ment method comprising spraying a dilution of the active comprising adding the active ingredient to a water culture ingredient with water or various solvents on a pest itself, the medium or the like, for the purpose of allowing the active Surface of a plant, or the soil or waterside near a plant. Specific 15 ingredient to permeate and transfer into the interior of the examples thereof include foliage spray treatment, flower plant body of a crop to be protected from damage Such as cluster spray treatment, trunk spray treatment, treatment ingestion by pests through the root part or the like of the plant. under tree crowns or around trunks, soil spray treatment, Specific examples thereof include incorporation into a water water Surface spray treatment, spray treatment by using a culture medium. manned helicopter, spray treatment by using an unmanned The fumigation treatment or the transpiration treatment is helicopter, and spray treatment by using an aircraft. a treatment method comprising diffusing the active ingredient The drenching treatment with a liquid formulation is a from a liquid formulation or a carrier containing the active treatment method comprising applying the active ingredient ingredient into the air by means of burning of an exothermic to soil, an irrigation water or the Surface or vessels of a plant, agent or an auxiliary Smoking agent, an external heat source for the purpose of allowing the active ingredient to permeate 25 utilizing chemical reaction, electricity or the like, or a natural and transfer into the interior of the plant body of a crop to be diffusion, thereby the active ingredient is allowed to adhere to protected from damage such as ingestion by pests. Specific the plant surface or a pest itself. Specific examples thereof examples thereof include drenching treatment of plant foot include treatment with a fumigant, treatment with a heating soil, drenching treatment of planting furrow soil, drenching transpiration agent, and treatment with a resin transpiration treatment of planting row soil, overall soil drenching treat 30 agent. ment, chemical injection treatment into the vessels of a plant, According to the pest control method of the present inven chemical drip irrigation treatment, chemigation treatment, tion, the present active ingredients may control pests in cul drenching treatment of a seedling raising box, drenching tivated lands and the like where plants including “crops” treatment of a nursery bed, and root immersion treatment. listed below are grown, without causing chemical damage to The spray treatment with a granule or the Soil incorporation 35 the “crops”. treatment with a granule is a treatment method comprising The “crops include plants listed below. applying a granule containing the active ingredient to the soil Agricultural crops: maize, rice, wheat, barley, rye, oat, or waterside near a plant, for the purpose of allowing the Sorghum, cotton, soybean, peanut, buckwheat, beet, rape active ingredient to permeate and transfer into the interior of seed, Sunflower, Sugarcane, tobacco, etc.; the plant body of a crop to be protected from damage such as 40 Vegetables: Solanaceous vegetables (egg plant, tomato, ingestion by pests through the root part, Surface or the like of green pepper, hot pepper, potato, etc.), cucurbitaceous Veg the plant. Specific examples thereof include planting hole etables (cucumber, pumpkin, Zucchini, water melon, melon, spray treatment, planting hole soil incorporation treatment, etc.), brassicaceous vegetables (Japanese radish, turnip, plant foot spray treatment, plant foot soil incorporation treat horseradish, kohlrabi, Chinese cabbage, cabbage, brown ment, planting furrow spray treatment, planting furrow soil 45 mustard, broccoli, cauliflower, etc.), asteraceous vegetables incorporation treatment, planting row spray treatment, plant (burdock, garland chrysanthemum, artichoke, lettuce, etc.), ing row soil incorporation treatment, seedling raising tray liliaceous vegetables (scallion, onion, garlic, asparagus, etc.), spray treatment, bed soil incorporation treatment, cover Soil/ umbelliferous vegetables (carrot, parsley, celery, parsnip, ridge soil incorporation treatment, overall soil spray treat etc.), chenopodiaceous vegetables (spinach, chard, etc.), ment, overall soil incorporation treatment, water Surface 50 lamiaceous vegetables (Japanese basil, mint, basil, etc.), spray treatment, foliar spray treatment in a growing period Strawberry, Sweet potato, yam, aroid etc.; and flower cluster spray treatment. Flowers and ornamental plants: acanthus, morning glory, The spray treatment with a granule or the Soil incorporation azalea, hydrangea, anemone raddeana, rhodohypoxis baurii, treatment with a granule is a treatment method comprising anemone, polygonatum odoratum, anaryllis, iris, alyssum, applying a granule containing the active ingredient to the soil 55 armeria, arctotis, China aster, edible flower, Bauera ruibio or waterside near a plant, for the purpose of allowing the ides, Cuban lily, Hosta montana, Mexican aster, four o'clock, active ingredient to permeate and transfer into the interior of Hypericum, oriental poppy, gentiana makinoi, Hosta aureo the plant body of a crop to be protected from damage such as marginata, Japanese iris, Clematis patens, gazania, Casa ingestion by pests through the root part, Surface or the like of Blanca, carnation, showy lily, gerbera, kalanchoe, cal the plant. Specific examples thereof include planting hole 60 ceolaria, curry plant, Carolina jasmine, canna, chrysanthe spray treatment, planting hole soil incorporation treatment, mum, Brugmansia, yellow cosmos, plantain lily, Kim Jon plant foot spray treatment, plant foot soil incorporation treat gilia, tea tree (Manuka), pot marigold, myrtle, masturtium, ment, planting furrow spray treatment, planting furrow soil gladiolus, Siam tulip, clematis, cockscomb, shrimp plant, incorporation treatment, planting row spray treatment, plant midday flower, cosmos, Hosta Sieboldii, Convolvulus arven ing row soil incorporation treatment, seedling raising tray 65 sis, Hosta sagae, primrose, Saffron crocus, Salvia, cyclamen, spray treatment, bed soil incorporation treatment, cover Soil/ moss phlox, Paeonia lactiflora, Anemone hupehensis, Bletilla ridge soil incorporation treatment, overall soil spray treat striata, Sweet pea, lily of the valley, Snowflake, portulaca, US 8,258,103 B2 9 10 violet, rose of Sharon, yarrow, Chinese pink, Zephyranthes, synthesizing enzyme inhibitor, or an herbicide such as bro pelargonium, geum, Zepher lily, dahlia, tithonia, tulip, choco moxynil by a classical breeding method or a genetic engineer late cosmos, Vinca major; Scilla, downy myrtle, German iris, ing technique. passionflower, dianthus, rape blossom, Madagascar peri Examples of the “crops' having herbicidal resistance given winkle, soft windflower, nemophila, Nerine, Swamp chrysan by a classic breeding technique include Clearfield (registered themum (North pole), Japanese water iris (iris ensata var. trademark) canola which is resistant to imidazolinone herbi spontanea), verbena, hibiscus, Joseph’s coat, coral flower, cides Such as imazethapyr, and STS Soybean which is resis Japanese water iris (Iris ensata), eastern redbud, spring star tant to sulfonylurea ALS inhibitor herbicides such as tifen flower, wavyleaf sea-lavender, California poppy, pansy, Vir sulfuron methyl. ginia Stock, daisy, corn poppy, Himalayan creeping saxifrage, 10 Examples of the “crops' having herbicidal resistance given Sunflower, hyacinth, crape-myrtle, Geranium, fuchsia, free by a genetic engineering technique include corn, soybean and sia, primula, garden balsam, ground-cherry, peony, Tricyrtis, cotton having resistance to glyphosate or glufosinate, which marguerite, marigold, Gymnaster savatieri, Strawflower, are already on the market under the product names of muscari, Japanese kerria, lily, ranunculus, lantana, gentian, 15 Roundup Ready (registered trademark), Liberty Link (regis Lupinus, lobelia, etc.; tered trademark), etc. Ornamental foliage plants: ivy, cattail, aglaonema, adian The “crops include crop plants which have acquired abil tum, asparagus, asplenium, ananas, aphelandra, alocasia, ity to produce insecticidal toxins known as selective toxins anthurium, Indian rubber tree, nepenthes, aechmea, produced from Bacillus bacteria by a genetic engineering aeschynanthus, episcia, strelitzia augusta, Spiders plant, Chi technique. nese banyan, kapok, caladium, calathea, Velvet plant (Gy Examples of insecticidal toxins expressed in Such geneti nura), Guzumania, Ctenanthe, gum tree, Crassula, Croton, cally engineered plants include insecticidal proteins pro A locasia Odora, orange jessamine, coffee tree, massangeana, duced from Bacillus cereus or Bacillus popilliae: Ö-endotox conifers, Coleus, cordyline, columnea, Sansevieria, Chinese ins such as Cry1Ab, Cry1Ac, Cry 1F, Cry 1Fa2, Cry2Ab. ixora, Schefflera, cissus, cyperus, reed rhapis, silk jessamine, 25 Cry3A, Cry3Bb1 and Cry9C produced from Bacillus thur syngonium, strelitzia, spathiphyllum, Senecio, zebrina, Japa ingiensis; insecticidal proteins such as VIP1,VIP2, VIP3 and nese Sago palm, tillandsia, tupidanthus, coral tree, dizygoth VIP3A; insecticidal proteins produced from nematode: tox eca, diefenbachia, duranta, bottle palm, dracaena, trades ins produced by animals such as a Scorpion toxin, a spider cantia, neoregelia, nephrolepis, hearts vine, hibiscus, toxin, a bee toxin and an insect specific nervous system toxin; pachypodium, Guiana chestnut (Pachira), ponytail, staghorn 30 filamentous fungus toxins; plant lectins; agglutinins; protease fern, pilea, fatshedera, ficus pumila, philodendron, bougain inhibitors such as trypsin inhibitors, serine protease inhibi villea, phoenix, fittonia, pteris, bridal veil, vriesea, plectran tors, patatin, cystatin and papain inhibitors: ribosome inacti thus, begonia, peperonia, heliconia, benjamina, poinsettia, vation proteins (RIP) such as ricins, corn-RIP. abrins, luffin, pothos, hoya, maranta, Belgian evergreen, milkbush, oyster saporins, and bryodin; Steroid metabolism enzymes Such as plant, monstera, palm, yucca, lantana, etc.; 35 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltrans Fruits: pomaceous fruits (apple, common pear, Japanese ferase, and cholesterol oxidase; ecdysone inhibitors; HMG pear, Chinese quince, quince, etc.), Stone fleshy fruits (peach, CoA reductase; ion channel inhibitors such as sodium chan plum, nectarine, Japanese plum, cherry, apricot, prune, etc.), nel and calcium channel inhibitors: Juvenile hormone citrus plants (Satsuma mandarin, orange, lemon, lime, grape esterase; diuretic hormone receptors; stilbene synthase; fruit, etc.), nuts (chestnut, walnut, hazel nut, almond, pista 40 bibenzyl synthase; chitinase; and glucanases. chio, cashew nut, macadamia nut, etc.), berry fruits (blue Further examples of insecticidal toxins expressed in Such berry, cranberry, blackberry, raspberry, etc.), grape, genetically engineered plants include hybrid toxins of Ö-en persimmon, olive, loquat, banana, coffee, date, coconut palm, dotoxin such as Cry1Ab, Cry1Ac, Cry 1F, Cry1 Fa2, Cry2Ab. etc., Cry3A, Cry3Bb1 and Cry 9C, and insecticidal proteins such Trees other than fruit trees: tea, mulberry, flowering trees, 45 as VIP1,VIP2, VIP3 and VIP3A, and insecticidal proteins in street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, which a part of amino acids constituting the insecticidal pro lilac, maple tree, oak, poplar, cercis, liquidambar, platanus, teins is deleted or modified. The hybrid toxins are created by Zelkova, Japanese arborvitae, fir tree, Japanese hemlock, combining different domains of the above insecticidal pro needle juniper, pine, spruce, yew), etc. teins by a genetic engineering technique. Fruits: pomaceous fruits (apple, common pear, Japanese 50 An example of the toxin in which a part of amino acids pear, Chinese quince, quince, etc.), Stone fleshy fruits (peach, constituting the insecticidal protein is deleted includes plum, nectarine, Japanese plum, cherry, apricot, prune, etc.), Cry1Ab in which a part of amino acids is deleted. citrus plants (Satsuma mandarin, orange, lemon, lime, grape An example of the toxin in which a part of amino acids fruit, etc.), nuts (chestnut, walnut, hazel nut, almond, pista constituting the insecticidal protein is modified is made by chio, cashew nut, macadamia nut, etc.), berry fruits (blue 55 Substitution of one or more amino acids of a natural toxin. berry, cranberry, blackberry, raspberry, etc.), grape, Examples of the insecticidal toxins and genetically engi persimmon, olive, loquat, banana, coffee, date, coconut palm, neered crop plants which have the ability to produce the etc., insecticidal toxins are described in EP-A-0374753, WO Trees other than fruit trees: tea, mulberry, flowering trees, 93/07278, WO95/34656, EP-A-0427529, EP-A-451878 and street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, 60 WO 03/052073. lilac, maple tree, oak, poplar, cercis, liquidambar, platanus, Such genetically engineered plants have become resistant Zelkova, Japanese arborvitae, fir tree, Japanese hemlock, to attack by Coleopteran pests, Dipteran pests and/or Lepi needle juniper, pine, spruce, yew), etc. dopteran pests due to the toxins which the plants have. The above-described “crops” include crop plants which Genetically engineered plants having one or more pest have become resistant to an HPPD inhibitor such as isoxaflu 65 resistant insecticidal genes and expressing one or more insec tole, an ALS inhibitor such as imazethapyr or thifensulfuron ticidal toxins are already known, and some of them are com methyl, an EPSP synthesizing enzyme inhibitor, a glutamine mercially available. US 8,258,103 B2 11 12 Examples of the genetically engineered plants include (Aleyrodidae) such as greenhouse whitefly (Trialeurodes YieldGard (registered trademark) (a corn variety expressing vaporariorum), and Sweetpotato whitefly (Bemisia tabaci); Cry1Ab toxin), YieldGard Rootworm (registered trademark) scales (Coccidae) Such as Califormia red scale (Aonidiella (a corn variety expressing Cry3Bb1 toxin), YieldGard Plus aurantii), San Jose scale (Comstockaspis perniciosa), citrus (registered trademark) (a corn variety expressing Cry1Aband 5 north scale (Unaspis citri), white peach scale (Pseudaulacas Cry3Bb1 toxins), Herculex I (registered trademark) (a corn pis pentagona), olive scale (Saissetia oleae), purple scale variety expressing Cry1 Fa2 toxin and phosphinothricin (Lepidosaphes beckii), red wax scale (Ceroplastes rubens), N-acetyltransferase (PAT) to confer resistance to glufosi and cottonycushion scale (Icerya purchasi), lace bugs nate), NuCOTN33B (registered trademark) (a cotton variety (Tingidae); psyllids (Psyllidae); etc. expressing Cry1Ac toxin), Bollgard I (registered trademark) 10 Lepidoptera: (a cotton variety expressing Cry1Ac toxin), Bollgard II (reg Pyralid moths (Pyralidae) such as rice stem borer (Chilo istered trademark) (a cotton variety expressing Cry1Ac and suppressalis), rice leafroller (Cnaphalocrocis medinalis), Cry2Ab toxins), VIPCOT (registered trademark) (a cotton European corn borer (Ostrinia nubilalis), cabbage webworm variety expressing VIP toxin), New Leaf (registered trade (Hellula undalis), bluegrass webworm (Parapediasia teter mark) (apotato variety expressing Cry3A toxin), NatureGard 15 rella), cotton leafroller (Notarcha derogata), and Indian meal (registered trademark), Agrisure (registered trademark) GT moth (Plodia interpunctella); Owlet moths (Noctuidae) such Advantage (GA21 glyphosate-resistance character), Agrisure as common cutworm (Spodoptera litura), armyworm (Pseu (registered trademark) CB Advantage (Btl corn borer (CB) daletia separata), cabbage armyworm (Mamestra brassi character), and Protecta (registered trademark). cae), black cutworm (Agrotis Thoricoplusia spp., Heliothis The “crops also include crop plants which have acquired spp., and Helicoverpa spp. Such as corn earworm (Helicov ability to produce selective anti-pathogen Substances by a erpa armigera); white butterflies (Pieridae) Such as common genetic engineering technique. white (Pieris rapae); tortricid moths (Tortricidae) such as Examples of the anti-pathogen Substances include PR pro Adoxophyes spp. Such as Smaller tea tortrix (Adoxophyes teins (PRPs, described in EP-A-0392225). Such anti-patho honnai) and Summer fruit tortrix (Adoxophyes Orana), and gen Substances and genetically engineered plants capable of 25 oriental fruit moth Grapholita molesta), and codling moth producing them are described, for example, in EP-A- (Cydia pomonella); Carposimidae such as peach fruit moth 0392225, WO95/33818 and EP-A-0353191. (Carposina niponensis); lyonetiid moths (Lyonetiidae) Such Examples of anti-pathogen Substances expressed in Such as Lyonetia prunifoliella; tussock moths (Lymantriidae) Such genetically engineered plants include ion channel inhibitors as Lymantria spp., and Euproctis spp.; yponomeutid moths Such as Sodium channel inhibitors and calcium channel 30 (Yponomeutidae) Such as diamondback moth (Plutella xylos inhibitors (KP1, KP4 and KP6 toxins and the like produced tella); gelechiid moths (Gelechiidae) such as pink bollworm by virus are known); stilbene synthase; bibenzyl synthase: (Pectinophora gossypiella); tiger moths and allies (Arctiidae) chitinase; glucanase; PR proteins; microorganism-producing such as fall webworm (Hyphantria cunea); tineid moths (Ti Substances such as peptide antibiotics, antibiotics having a neidae) Such as casemaking clothes moth (Tinea translucens), heterocycle, and protein factors relating to resistance against 35 and webbing clothes moth (Tineola bisselliella); etc. palant pathogens (described in WO 03/000,906). Diptera: According to the pest control method of the present inven Culices such as common mosquito (Culex.pipiens pallens), tion, the present active ingredients may be used in combina and Cluex tritaeniorhynchus, Aedes spp. Such as yellow fever tion with other pesticides such as insecticides, acaricides, mosquito (Aedes aegypti), and Asian tiger mosquito (Aedes nematocides, fungicides, herbicides, plant hormone agents 40 albOpictus); Anopheles spp. Such as Anopheles sinensis; chi and plant growth regulators, synergists, crop injury-reducing ronomids (Chironomidae); house flies (Muscidae) such as agents, pigments, fertilizers, soil conditioners, animal feed Musca domestica, and Muscina stabulans; blow flies (Calli and the like. phoridae); flesh flies (Sarcophagidae); little house flies (Fan The present active ingredients or the present active ingre niidae); anthomyiid flies (Anthomyiidae) Such as seedcornfly dients dissolved in a solvent can be also Supported on a resin 45 (Delia platura), and onion fly (Delia antiqua); leafminer flies Such as polypropylene or polyethylene by kneading, Surface (Agromyzidae) Such as legume leafminer (Liriomyza trifolii); treatment, etc. to prepare a resin formulation. Such a resin fruit flies (Tephritidae); Drosophilidae; moth flies (Psychod formulation is applied to a habitat of pests by being placed idae); Simuliidae: Tabanidae; stable flies, etc. near plants such as agricultural crop plants. Hymenoptera: Examples of pests which can be controlled by the present 50 Sawflies (Tenthredinidae) such as Cabbage sawfly (Athalia invention include arthropods such as insects and mites, and rosae); Argidae such as rose sawfly (Arge pagana); hornets nemathelminthes such as nematodes listed below. (Vespidae) Such as yellow hornet (Vespa simillima), and Hemiptera: Polistes chinensis; ants (Formicidae) Such as pharaoh ant Planthoppers (Delphacidae) such as small brown plantho (Monomorium pharaosis); bethylid wasps (Bethylidae), etc. pper (Laodelphax striatellus), brown rice planthopper 55 Coleoptera: (Nilaparvata lugens), and white-backed rice planthopper Corn root worms (Diabrotica spp.) such as Western corn (Sogatella fircifera); leafhoppers (Deltocephalidae) Such as root worm (Diabrotica virgifera virgifera), and Sourthern green rice leafhopper (Nephotettix cincticeps), green rice cornroot worm (Diabrotica undecimpunctata howardi); scar leafhopper, and (Nephotettix virescens); aphids (Aphididae) abs (Scarabaeidae) Such as cupreous chafer (Anomala Such as cotton aphid (Aphis gossypii), green peach aphid 60 cuprea), and soybean beetle (Anomala rufocuprea); weevils (Myzus persicae), green citrus aphid (Aphis citricola), turnip Such as maize weevil (Sitophilus zeanais), rice water weevil aphid (Lipaphis pserudobrassicae), pear green aphid (Nippo (Lissorhoptrus Oryzophilus), alfalfa weevil (Hypera pastica), lachnus piri), black citrus aphid (Toxoptera aurantii), and and azuki bean weevil (Calosobruchus chinensis); darkling tropical citrus aphid (Toxoptera citricidus); Stink bugs (Pen beetles (Tenebrionidae) such as yellow mealworm (Tenebrio tatomidae) Such as green Stink bug (Nezara antennata), nar 65 molitor), and red flour beetle (Tribolium castaneum); leaf row coreidbug (Cletus punctiger), bean bug (Riptortus clave beetles (Chrysomelidae) such as cucurbit leaf beetle (Aula tus), and brownwinged green bug (Plautia Stali); whiteflies cophora femoralis), striped flea beetle (Phyllotreta striolata), US 8,258,103 B2 13 14 and Colorado potato beetle (Leptinotarsa decemlineata); nematode (Pratylenchus loosi), and walnut root-lesion nema Epillachna Such as Twenty-eight-spotted ladybird (Epillachna tode (Pratylenchus vulnus); cyst nematodes such as Soybean vigintioctopunctata); false powderpost beetles (Bostry cyst nematode (Heterodera glycines), and potato cyst nema chidae); bark beetles (Scolytidae) such as powder post beetle tode (Globodera rostochiensis); root-knot nematodes such as (Lyctus brunneus); longhorn beetles (Cerambycidae); northern root-knot nematode (Meloidogyne hapla), and Paederus fiscipens, etc. Southern root-knot nematode (Meloidogyne incognita); Alph Blattodea: elen.choides sp. Such as rice white-tip nematode (Aphelen German cockroach (Blattella germanica), Smokybrown choides besseyi), and strawberry nematode (Aphelen.choides cockroach (Periplaneta fuliginosa), American cockroach fragariae); stunt nematodes (Tvlenchorhynchus sp.), ring (Periplaneta americana), Periplaneta brunnea, oriental 10 nematodes (Criconenoides sp.), pin nematodes (Paratylen cockroach (Blatta Orientalis), etc. chus sp.), Longidorus sp., Trichodorus sp., etc. Thysanoptera: When the composition of the present invention or the Thrips (Thripidae) such as melon thrips (Thrips palmi), present active ingredient is used for pest control, the applica onion thrips (Thrips tabaci), banana flower thrips (Thrips tion amount thereof is such an amount that the present com hawaiiensis), yellow tea thrips (Scirtothrips dorsalis), flower 15 pound 1 and the present compound 2 are applied in a com thrips (Frankliniella intonsa), yellow citrus thrips (Franklin bined amount of usually 0.1 to 1,000 g, preferably 1 to 100 g iella Occidentalis), Ponticulothrips diospyrosi, etc. per 10 ares. When the composition of the present invention is Orthoptera: in the form of an emulsifiable concentrate or a flowable for Mole crickets, grasshoppers, etc. mulation, it is usually applied after it is diluted with water so Shiphonaptera: that the active ingredient concentration becomes 1 to 500,000 Cat flea (Ctenocephalides felis), dog flea (Ctenocephalides ppm, preferably 10 to 100,000 ppm. When the composition of canis), human flea (Pulex irritans), etc. the present invention is in the form of a granule or a dust, it is Anoplura: usually used as it is. The composition of the present invention Head louse (Pediculus humanus humanus), Human body or the present active ingredient may be applied directly to louse (Pediculus humanus corporis), crab louse (Phthirus 25 pests or plants such as crop plants to be protected from pests, pubis), etc. or may be applied to a place where pests inhabit, thereby the Termites Such as Japanese subterranean termite (Reticuli pests can be controlled. termes speratus), Formosan Subterranean termite (Coptoter The application amount and concentration vary depending mes formosanus), western drywood termite (Incisitermes on conditions such as the type of a formulation, an application minor), Daikoku drywood termite (Cryptotermes domesti 30 period, an application area, an application method, the kind of cus), Odontotermes formosanus, Neotermes koshunensis, a pest, the extent of damage and the like, and may be appro Glyptotermes Satsumesis, Glyptotermes nakajimai, Glypto priately increased or decreased regardless of the above-de termes fuscus, Glyptotermes kodamai, Glyptotermes kushi scribed ranges. mensis, Japanese dampwood termite (Hodotermopsis Hereinafter, the present invention will be explained in more japonica), Coptotermes guangzhoensis, Reticulitermes 35 detail by the way of Formulation Examples and Test miyatakei, eastern Subterranean termite (Reticulitermes fia Examples which the present invention is not limited to. vipes amamianus), Reticulitermes sp., Nasutitermes takasa First, Formulation Examples will be described. The term goesis, Pericapritermes nitobei, Sinocapritermes mushae, "part(s) means part(s) by weight. etc. Isopoda. 40 Formulation Example 1 Common rough woodlouse (Porcellio scaber), Porcellion ides pruinosus, common pill bug (Armadillidium vulgare), 5 parts of spinetoram as the present compound 1, 5 parts of etc. pyridalyl as the present compound 2, 8 parts of polyoxyeth Chilopoda: ylene Styrylphenyl ether, 2 parts of calcium dodecylbenzene Scolopendra subspinipes mutilians, Scolopendra subspin 45 sulfonate and 80 parts of xylene are mixed uniformly to ipes japonica, House centipede (Thereuonema hilgendorfi), obtain an emulsifiable concentrate. etc. Diplopoda. Formulation Example 2 Garden millipede (Oxidus gracilis), Parafontaria laminata laminata, etc. 50 4 parts of spinetoram as the present compound 1, 20 parts Acarina: of pyridalyl as the present compound 2, 3 parts of Sodium Spider mites (Tetranychidae) such as two-spotted spider dodecylbenzenesulfonate, 3 parts of Sodium ligninsulfonate mite (Tetranychus urticae), Kanzawa spider mite (Tetrany and 70 parts of diatomaceous earth are mixed and milled chus kanzawaii), citrus red mite (Panonychus citri), European uniformly with a jet air mill to obtain a wettable powder. red mite (Panonychus ulmi), and Oligonychus spp., eriophyid 55 mites (Eriophyidae) Such as tomato rust mite (Aculops lyco Formulation Example 3 persici), pink citrus rust mite (Aculops pelekassi), and purple tea mite (Calacarus carinatus); tarosonemid mites (Tarson 0.5 part of spinetoram as the present compound 1, 1 part of emidae) Such as broad mite (Polyphagotarisonemus latus); pyridalyl as the present compound 2, 48.5 parts of talc and 50 false spider mites (Tenuipalpidae); Tuckerellidae; rat mites: 60 parts of clay are mixed and stirred uniformly to obtain a dust. ticks (Ixodidae); acarid mites (Acaridae); house dust mites (Pyroglyphidae) Such as Dermatophagoides farinae; chey Formulation Example 4 letide mites (Cheyletidae) such as Chelacaropsis moorei; parasitoid mites (Dermanyssidae), etc. To 1 part of spinetoram as the present compound 1 and 4 Nematoda: 65 parts of pyridalyl as the present compound 2 are added 5 parts Root-lesion nematode such as coffee root-lesion nematode of sodium dodecylbenzenesulfonate, 30 parts of bentonite (Pratylenchus coffeae), Pratylenchus fallax, tea root-lesion and 60 parts of clay. The mixture is mixed and stirred thor US 8,258,103 B2 15 16 oughly. Then, a properamount of water is added to the mix smectite mineral and 60 parts of water are mixed uniformly. ture. The mixture is stirred, granulated with a granulator and To the mixture are added 2 parts of spinosad as the present then dried by ventilation to obtain a granule. compound 1 and 10 parts of pyridalyl as the present com pound 2. The mixture is stirred thoroughly and then wet Formulation Example 5 5 milled with a sand mill to obtain a flowable formulation. 5 parts of polyoxyethylene styrylphenyl ether sulfate, 20 parts of a 1% Xanthan gum aqueous solution, 3 parts of a Formulation Example 13 smectite mineral and 60 parts of water are mixed uniformly. To the mixture are added 2 parts of spinetoram as the present 0.02 part of spinosad as the present compound 1 and 0.1 compound 1 and 10 parts of pyridalyl as the present com 10 part of pyridalyl as the present compound 2 are dissolved in pound 2. The mixture is stirred thoroughly and then wet 10 parts of acetone. The solution is uniformly mixed with milled with a sand mill to obtain a flowable formulation. 99.88 parts of a powdered solid animal feed (CE-2:powdered chow for breeding, manufactured by Clea Japan Inc.). Then, Formulation Example 6 15 the mixture is air dried to remove acetone to obtain a poison bait. 0.02 part of spinetoram as the present compound 1 and 0.1 part of pyridalyl as the present compound 2 are dissolved in Formulation Example 14 10 parts of acetone. The solution is uniformly mixed with 99.88 parts of a powdered solid animal feed (CE-2:powdered 0.1 part of spinosadas the present compound 1 and 0.1 part chow for breeding, manufactured by Clea Japan Inc.). Then, of pyridalyl as the present compound 2 are dissolved in 5 parts the mixture is air dried to remove acetone to obtain a poison of xylene and 5 parts of trichloroethane. The solution is mixed bait. with 89.8 parts deodorized kerosene to obtain an oil solution. The following Test Examples demonstrate that the present Formulation Example 7 25 invention is effective in pest control. The theoretical value of 0.1 part of spinetoram as the present compound 1 and 0.1 an insecticidal (ovicidal) rate obtained by using a mixture of part of pyridalyl as the present compound 2 are dissolved in 5 2 kinds of active ingredients was calculated by the following parts of xylene and 5 parts of trichloroethane. The solution is formula: mixed with 89.8 parts deodorized kerosene to obtain an oil Solution. 30 which conforms to the Colby's formula. Formulation Example 8 X: Insecticidal rate (%) of the active ingredient A at MPpm Y: Insecticidal rate (%) of the active ingredient B at N ppm 5 parts of spinosad as the present compound 1, 5 parts of 35 E: Theoretical insecticidal rate (%) of combination use of the pyridalyl as the present compound 2, 8 parts of polyoxyeth active ingredient A at M ppm and the active ingredient B at N ylene Styrylphenyl ether, 2 parts of calcium dodecylbenzene ppm sulfonate and 80 parts of xylene are mixed uniformly to When an actual insecticidal (ovicidal) rate exceeds the obtain an emulsifiable concentrate. theoretical value, it is determined that the used two active Formulation Example 9 40 ingredients produce a synergetic effect. 4 parts of spinosad as the present compound 1, 20 parts of Test Example 1 pyridalyl as the present compound 2, 3 parts of sodium dode cylbenzenesulfonate, 3 parts of sodium ligninsulfonate and (1) 12 parts of spinetoram as the present compound 1, 35 70 parts of diatomaceous earth are mixed and milled uni 45 parts of a carrier on which a polyoxyethylene alkyl ether formly with a jet air mill to obtain a wettable powder. Sulfate ammonium salt and white carbon in a weight ratio of 1:1 were adsorbed, and 53 parts of water were mixed, and Formulation Example 10 finely milled by a wet milling method to obtain a spinetoram formulation (hereinafter, referred to as the formulation A). 0.5 part of spinosad as the present compound 1, 1 part of 50 (2) A flowable formulation containing 10 parts of pyrida pyridalyl as the present compound 2, 48.5 parts of talc and 50 lyl, which is the present compound 2, as the active ingredient parts of clay are mixed and stirred uniformly to obtain a dust. (trade name: PLEO flowable, manufactured by Sumitomo Chemical Co., Ltd.) (hereinafter, referred to as the formula Formulation Example 11 55 tion B) was used. To 1 part of spinosadas the present compound 1 and 4 parts (3) The formulation A was diluted with water to prepare a of pyridalyl as the present compound 2 are added 5 parts of water dilution having an active ingredient concentration sodium dodecylbenzenesulfonate, 30 parts of bentonite and shown in Table 1. To the water dilution, 1/5,000 volume of a 60 parts of clay. The mixture is mixed and stirred thoroughly. spreading agent (Sindain, manufactured by Sumitomo Then, a proper amount of water is added to the mixture. The 60 Chemical Takeda Agro Co., Ltd.) was added to prepare a test mixture is stirred, granulated with a granulator and then dried Solution containing the present compound 1. The formulation by Ventilation to obtain a granule. B was diluted with water to prepare a water dilution having an active ingredient concentration shown in Table 1. To the water Formulation Example 12 dilution, 1/5,000 volume of a spreading agent (Sindain, 65 manufactured by Sumitomo Chemical Takeda Agro Co., 5 parts of polyoxyethylene styrylphenyl ether sulfate, 20 Ltd.) was added to prepare a test solution containing the parts of a 1% Xanthan gum aqueous solution, 3 parts of a present compound 2. US 8,258,103 B2 17 18 A water dilution of the formulation A and a water dilution The formulation B was diluted with water to prepare a of the formulation B were mixed so that the respective active water dilution having an active ingredient concentration ingredients could reach concentrations shown in Table 1. To shown in Table 2. To the water dilution, 1/5,000 volume of a the mixture, 1/5,000 volume of a spreading agent (Sindain, manufactured by Sumitomo Chemical Takeda Agro Co., spreading agent (Sindain, manufactured by Sumitomo Ltd.) was added to prepare a test solution containing the Chemical Takeda Agro Co., Ltd.) was added to prepare a test present compound 1 and the present compound 2. Solution containing the present compound 2. (4) A cabbage was planted in a pot and grown until the A water dilution of the formulation A and a water dilution fourth leaf stage. The leaves of the cabbage were cut off one of the formulation B were mixed so that the respective active by one, and then immersed in the above-described test solu 10 tion for 60 seconds. After air drying, the cabbage leaves were ingredients could reach concentrations shown in Table 2. To each placed in a cup with a filter paper spread on the bottom. the mixture, 1/5,000 volume of a spreading agent (Sindain, Ten fourth-instar larvae of Spodoptera litura were released manufactured by Sumitomo Chemical Takeda Agro Co., into each cup. After 2 days, the tested larvae were observed Ltd.) was added to prepare a test solution containing the for life or death. An insecticidal rate was calculated and 15 present compound 1 and the present compound 2. corrected according to the following formula. Results are shown in Table 1. (2) A cabbage was planted in a pot and grown until the fourth leaf stage. The leaves of the cabbage were cut off one Insecticidal rate (%)=100x(Mt-Mc)/(100-Mc) by one, and then immersed in the above-described test solu Mt. Worm death rate (%) in a section treated with a test tion for 60 seconds. After air drying, the cabbage leaves were compound each placed in a cup with a filter paper spread on the bottom. Mc: Worm death rate (%) in a section not treated with a test Ten fourth-instar larvae of Spodoptera litura were released compound into each cup. After 2 days, the tested larvae were observed TABLE 1 Active Active ingredient Theoretical value Found value of Determination of ingredient in Concentration of insecticidal insecticidal synergetic test solution (ppm) rate (%) rate (%) effect Spinetoram 2.9 - 2.5 O 6O.O Yes (present compound 1) + O.73 - 2.5 O SO.O Yes Pyridalyl (present compound 2) Spinetoram 2.9 O O (present 0.73 O O compound 1) Pyridalyl 2.5 O O (present compound 2) Untreated O

Test Example 2 for life or death. An insecticidal rate was calculated and corrected according to the following formula. (1) The formulation A was diluted with water to prepare a water dilution having an active ingredient concentration 45 Insecticidal rate (%)=100x(Mt-Mc)/(100-Mc) shown in Table 2. To the water dilution, 1/5,000 volume of a Mt: Worm death rate (%) in a section treated with a test spreading agent (Sindain, manufactured by Sumitomo compound Chemical Takeda Agro Co., Ltd.) was added to prepare a test Mc: Worm death rate (%) in a section not treated with a test Solution containing the present compound 1. compound TABLE 2 Active Active ingredient Theoretical value Found value of Determination of ingredient in concentration of insecticidal insecticidal synergetic test solution (ppm) rate (%) rate (%) effect Spinetoram O.25 - 2.5 16.7 8O.O Yes (present compound 1) -- 2.5 + 0.25 O SO.O Yes Pyridalyl (present compound 2) Spinetoram 2.5 O (present O.25 O compound 1) Pyridalyl 2.5 16.7 (present O.25 O compound 2) Untreated US 8,258,103 B2 19 20 INDUSTRIAL APPLICABILITY 2. The composition according to claim 1, wherein R is an ethyl group. According to the present invention, it is possible to provide 3. The composition according to claim 1, wherein the com a pesticidal composition having an excellent controlling pound represented by the formula (I) is spinetoram. effect on pests, and so on. 4. A pest control method which comprises a step of apply The invention claimed is: ing an effective amount of a compound represented by the 1. A pesticidal composition comprising:, a compound rep formula (I): resented by the formula (I):

wherein A is a single bond or a double bond, wherein A is a single bond or a double bond, 25 B is a double bond, B is a double bond, R is a group represented by the formula (II): R is a group represented by the formula (II): (II) R8 (II) 30 Js R1 N\ wherein Rs and Ro are methyl groups, wherein Rs and Ro are methyl groups, 35 R is a hydrogen atom or a methyl group, R is a hydrogen atom or a methyl group, R is a methyl group, R is a methyl group, R is a methyl group or an ethyl group, R is a methyl group or an ethyl group, R is a methyl group, R is a methyl group, Rs is a hydrogen atom, R is a hydrogen atom, 40 R is a methyl group, and R is a methyl group, and R, is an ethyl group; and R is an ethyl group; and an effective amount of 2,6-dichloro-4-(3.3-dichloroally 2,6-dichloro-4-(3,3-dichloroallyloxy)phenyl 3-5-(trifluo loxy)phenyl 3-5-(trifluoromethyl)-2-pyridyloxypro romethyl)-2-pyridyloxypropyl ether as active ingredi pyl ether to pests or a place where pests inhabit, ents, 45 wherein a weight ratio of the compounds being from 10:1 wherein a weight ratio of the compounds being from 10:1 to 1:10. to 1:10.