AU769975B2

AU769975B2 - Thiazolylcinnamonitrile compounds and insecticides and miticides

Info

Publication number: AU769975B2
Application number: AU22250/01A
Authority: AU
Inventors: Koichirou Aoyagi; Takao Iwasa; Yasushi Shibata; Hidemitsu Takahashi
Original assignee: Nippon Soda Co Ltd
Current assignee: Nippon Soda Co Ltd
Priority date: 1999-12-27
Filing date: 2000-12-26
Publication date: 2004-02-12
Anticipated expiration: 2020-12-26
Also published as: IL150156A0; CN1413201A; KR20020067577A; AU2225001A; WO2001047903A1; BR0016797A

Description

P:AOPER\Kbmi22250-01 claims doc-04/12/03 -1- THIAZOLYLCINNAMONITRILES, AND INSECTICIDES AND ACARICIDES Field of Invention: The present invention relates to novel thiazolylcinnamonitriles, and insecticides and acaricides containing the said compounds as active ingredients.

Background Art: A large number of pest controlling agents, such as insecticides and acaricides, have been used so far. However, many of them are hardly satisfactory controlling agents because of insufficient efficacy, restrictions on their use due to drug resistance problems, chemical injuries or pollution on plants, or strong toxicity on humans, domestic animals and fish. Therefore, there has been a desire for the development of agents applicable safely and having less of the drawbacks mentioned above.

Cinnamonitrile derivatives similar to the compounds of the present invention, for example, 3-hyroxy-2-(4-phenyl-2-thiazolyl)-cinnamonitriles are disclosed in Japanese Patents Laid-open Nos. Sho 53-92769 and Sho 55-154963 and EP 189960, and their alkali metal and ammonium salts in Japanese Patent Laid-open No. Sho 55-154962. However, none of them have been put to practical use as insecticides because of insufficient efficacy and other problems.

Further, WO 95/29591 and Japanese Patent Laid-open No. Hei 10-158254 have disclosed that cinnamonitrile derivatives, similar to the compounds of the present invention, are useful as anti-fouling agents for aquatic adhesive organisms. There is, however, no description of their insecticidal activities.

The reference to any prior art in this specification is not, and should not be taken as, an acknowledgment or any form of suggestion that that prior art forms part of the common general knowledge in Australia.

Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps.

P:\OPER\Kbm\22250-01 clims.doc-04/12/03 1A- Disclosure of the Invention: Advantageously at least one embodiment of the present invention may provide insecticides and acaricides containing thiazolylcinnamonitriles as active ingredients, with sure efficacy and safe applications.

The present invention is directed to compounds represented by Formula (1) H Y,

S

l (1)

(X

3 )n

N

S CN "X2 wherein X 1

X

2 and X 3 are, each independently, halogen, C1-3 alkyl or C1- 3 haloalkyl; n is 0 or an integer of 1 to 3;

Y

1 is halogen, C1- 3 alkyl, C1- 4 alkoxy or C 1 -3 haloalkyl; and

Y

2 is hydrogen, halogen, C1- 3 alkyl, C1- 4 alkoxy or C1- 3 haloalkyl, when used as an insecticide or acaricide. The invention is also directed to methods of controlling insect and acarid pests comprising applying one or more of the said compounds of Formula In the above Formula

X

1

X

2 and X 3 are halogen such as fluorine, chlorine, bromine or iodine;

C

1 3 alkyl such as methyl, ethyl, propyl or isopropyl; or .o *oo 0o *o

C

1 3 haloalkyl such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl or pentafluoroethyl; Y, is halogen such as fluorine, chlorine, bromine or iodine;

C

1 3 alkyl such as methyl, ethyl, propyl or isopropyl;

C,

1 alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or t-butoxy; or

C

1 3 haloalkyl such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl or pentafluoroethyl; and

Y

2 is hydrogen, halogen such as fluorine, chlorine, bromine or iodine;

C

1 3 alkyl such as methyl, ethyl, propyl or isopropyl;

C

1 .4 alkoxy as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy or tbutoxy; or

C

1 3 haloalkyl such as chloromethyl, fluoromethyl, bromomethyl, dichloromethyl, difluoromethyl, dibromomethyl, trichloromethyl, trifluoromethyl, tribromomethyl, trichloroethyl, trifluoroethyl or pentafluoroethyl.

Preferred substituents X, and X 2 include, each independently, fluorine, chlorine, methyl or trifluoromethyl.

The compounds of the present invention, represented by Formula have two stereoisomers and three tautomers, as shown below. These isomers are all covered by the present invention.

2 1Y tX3 0(X3 W Y2 The compounds of the present invention can be used to control agricultural pests, sanitary insect pests, stored grain insect pests, cloth insect pests, house insect pests and the like, and have activities of killing adults, nymphs, larvae and eggs.

The compounds of the said Formula whose phenyl group at position 4 of the thiazole ring has substituents at positions 2 and 6, have far better insecticidal activities than known compounds having non-substituted or 2-mono-substituted phenyl groups do. Among the compounds of the present invention, compounds where X, and X 2 are, each independently, chlorine, fluorine, methyl or trifluoromethyl and Y 1 is chlorine, fluorine, bromine, methyl, methoxy or trifluoromethyl are particularly good.

Representative examples of insect pests to which the insecticidal and acaricidal formulations of the present invention are applicable are shown in the following: Examples of Lepidopterous insect pests include cotton leafworm, cabbage armyworm, black cutworm, common cabbegeworm, cabbage looper, diamond-back, smaller tea tortrix, tea leaf roller, peach fruit moth, oriental fruit moth, citrus leaf miner, tea leaf roller, apple leaf miner, gypsy moth, tea tussock moth, rice stem borer, grass leaf roller, European corn borer, fall webworm, almond moth, Heliothis sp., Helicoverpa sp., Agrotis sp., casemaking clothes moth, codling moth and cotton bollworm.

Examples of Hemipterous insect pests include green peach aphid, cotton aphid, turnip aphid, grain aphid, bean bug, common green stink bug, arrowhead scale, mulberry mealy scale, greenhouse whitefly, tobacco whitefly, pear psylla, Japanese pear lace bug, brown planthopper, small brown planthopper, white-backed planthopper and green rice leafhopper.

Examples of Coleopterous insect pests include striped flea beetle, cucurbit leaf beetle, Colorado potato beetle, rice water weevil, rice weevil, azuki bean weevil, Japanese beetle, soybean beetle, Diabrotica sp., cigarette beetle, powder post beetle, pine sawyer, white-spotted longicor beetle, Agriotis sp., 28-spotted ladybeetle, rust-red flour beetle and cotton boll weevil.

Examples of Dipterous insect pests include housefly, Calliphora lata, Boettcherisca peregrina, cucurbit fruit fly, citrus fruit fly, seed maggot, rice leaf miner, yellow drosophila, Stomoxys calcitrans, Culex tritaeniarhynchus, Aedes aegypti and Anopheles hyrcanus.

Examples of Thysanopterous insect pests include Thrips palmi and tea thrips.

Examples of Hymenopterous insect pests include Monomorium pharaonis, yellow harnet and cabbage sawfly.

Examples of Dictyopterous insect pests include German cockroach, American cockroach and Japanese cockroach.

Examples ofIsopterous insect pests include Formosan subterranean termite and Reticulitermes speratus Kolbe.

Examples ofAphanipterous insect pests include human flea.

Examples of Anoplurous insect pests include human louse.

Examples of mites include two-spotted spider mite, carmine mite, Kanzawa spider mite, citrus red mite, European red mite, citrus rust mite, apple rust mite, Tarsonemus sp., Brevipalpus sp., Eotetranychus sp., Robin bulb mite, common grain mite, Desmatophagoidesfarinae, Boophilus microplus and Haemaphysallis bispinosa.

Examples of plant-parasitic nematodes include southern root-knot nematode, root lesion nematode, soybean cyst nematode, rice white-tip nematode and pine wood nematode.

The compounds of the present invention are favorably applied to, among these insect pests, Lepidopterous, Hemipterous, Coleopterous and Thysanopterous insect pests and phytophagous mites, particularly preferably to Lepidopterous, Hemipterous and Thysanopterous insect pests and phytophagous mites.

Many insect pests such as diamond-back, planthoppers, leafhoppers and aphids, and phytophagous mites have developed resistance against organophosphorus pesticides, carbamate insecticides and acaricides. Therefore, the chemicals have had the problem of lack of efficacy. There has been a desire for chemicals effective on insect pests and mites of resistant lines.

The compounds of the present invention are chemicals having excellent insecticidal and acaricidal effects on insect pests resistant to organophosphorus pesticides, carbamate insecticides or pyrethroid type agents and mites resistant to acaricides, as well as those of sensitive lines.

The compounds of the present invention induce very slight chemical injuries, have low toxicity on fish and warm-blood animals, and are highly safe.

Forms to Implement the Invention: The compounds of the present invention are prepared, for example, according to the following:

X

1 rY2

C

(X

3 2 (3) X S OH

(X

3 )n -IYz2

X

2

Y

1 (1) (wherein X 1

X

2

X

3

Y

1

Y

2 and n are as defined above, and L is a leaving group such as halogen, Ci 1 6 alkoxy, phenoxy, 1-imidazolyl, 1-pyrazolyl, p-toluenesulfonyloxy, methanesulfonyloxy or trifluoromethanesulfonyloxy).

SThat is, 1 mole of a compound of Formula is reacted with 0.5 to 2 moles of a compound of Formula in an inert solvent in the presence of a base, to give a compound of Formula Examples of bases used for this reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium carbonate and potassium carbonate; organic metals such as n-butyl lithium and lithium diisopropylamide (LDA); and organic bases such as triethylamine, diisopropylethylamine and pyridine.

Solvents able to be used include N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO), tetrahydrofuran (THF), acetonitrile, hexamethylphosphoric amide (HMPA), benzene, toluene, dichloromethane, chloroform and carbon tetrachloride. Preferred reaction temperatures are from -78 0 C to the boiling point of solvents used.

A target compound is obtained with usual post-treatments after the completion of the reaction.

(Insecticides and Acaricides) The compounds of the present invention can be used in the pure form without adding other ingredients, when they are actually applied as insecticides or acaricides. When applied as agricultural chemicals, they may be used in forms that general agricultural chemicals can take, such as wettable powders, granules, dusts, emulsifiable concentrates, water soluble powders, flowable concentrates, floables and water dispersible granules.

In order to make solid formulations, vegetable powders such as soybean flour and wheat flour; fine mineral powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, pyrophylite and clay; and organic and inorganic compounds such as sodium benzoate, urea and Glauber's salt can be used as additives and carriers.

When the purpose is to prepare liquid formulations, kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, DMF, DMSO, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oils, vegetable oils, water and the like can be used as solvents.

It is possible to further add surfactants, if required, to make these formulations homogeneous and stable forms. There are no particular restrictions on surfactants used. Their examples include nonionic surfactants such as polyoxyethylene-added alkylphenyl ethers, polyoxyethylene-added alkyl ethers, polyoxyethylene-added higher fatty acid esters, polyoxyethylene-added sorbitan higher fatty acid esters and polyoxyethylene-added tristylylphenyl ethers; polyoxyethylene-added alkylphenyl ether sulfates, alkylbenzene sulfonates, higher alcohol sulfates, alkylnaphthalene sulfonates, polycarboxylic acid salts, lignin sulfonates, condensation products of alkylnaphthalene sulfonates with formaldehyde, and copolymers ofisobutylene and maleic anhydride.

An amount of the active ingredient (a compound of the present invention) in a formulation is preferably 0.01 to 90% by weight, more preferably about 0.05 to 85% by weight. The obtained wettable powders, emulsifiable concentrates, flowable concentrates and flowables are diluted with water to specified concentrations to use as suspensions or emulsions. The dusts and granules are used, as they are, to directly spray on plants or soil.

It goes without saying that the compounds of the present invention are sufficiently effective by themselves. They can be used, however, by mixing with one or more of various fungicides, insecticides, acaricides or synergists.

Representative examples of bactericides, insecticides, acaricides and plant growth regulators that can be used to mix with the compounds of the present invention are shown in the following: Fungicides: Captan, Forpet, Thiuram, Ziram, Zineb, Maneb, Mancozeb, Propineb, Polycarbamate, Chlorotalonyl, Quintozene, Captafol, Iprodione, Prothimidon, Vinclosolin, Fluorimide, Cymoxanil, Mepronyl, Flutoranyl, Penthichlon, Oxycarboxin, Phosethyl-aluminum, Propamocarb, Triazimefon, Triazimenol, Propiconazole, Dichloptrazole, Bitertanol, Hexaconazole, Microbutanil, Flusilazole, Ethaconazole, Fluotrimazole, Flutriafen, Penconazole, Diniconazole, Cyproconazole, Phenalimol, Triflumizole, Prochloraz, Imazaryl, Pefurazoate, Tridemorph, Fenpropymorph, Triforin, Buthiobate, Pryfenox, Anilazine, Polyoxin, Metharaxyl, Oxadixyl, Flaraxyl, Isoprothiorane, Probenazole, Pyrolnitrin, Blasticidin S, Kasugamycin, Validamycin, Sulfric acid dihydrostreptomycin, Benomil, Carbendazim, Thiophanate-methyl, Hymexazole, Basic copper chloride, Basic copper sulfate, Triphenyl tin acetate, Triphenyl tin hydroxide, Diethofencarb, Methasulfocarb, Quinomethionate, Binapacryl, Lecithin, Sodium carbonate, Dithianon, Dinocap, Phenaminosulf, Dichlomezine, Guazatine, Dozin, IBP, Edifenphos, Mepanipyrim, Ferimzone, Trichiamide, Methasulfocarb, Fluazinam, Etokinorakku, Dimethomorpli, Pyroquiron, Tecrofutaram, Futharide, Phenazinoxyde, Thiabendazole, Tricyclazole, Vinclozolin, Cymoxanil, Cyclobutanyl, Guazatine, Propamocarbhydrochloride and Oxolinic acid.

Insecticides and Acaricides: Organophosphorus and Carbamate Insecticides: Fenthion, Fenitrothion, Diazinon, Chiorpyrifos, ESP, Vamidothion, Fenthoate, Dimethoate, Formothion, Malathon, Trichiorfon, Thiomethon, Phosmet, Dichiorvos, Acephate, EPBP, Methylparathion, Oxydimethonmethyl, Ethion, Salithion, Cyanophos, Isoxathion, Pyridafenthion, Phosalon, Methidathion, Suiprofos, Chlorfenvinphos, Tetrachlorvinphos, Dimethylvinphos, Propaphos, Isofenphos, Ethyithiomethon, Profenofos, Pyrachiofos, Monoclotophos, Azinphosmethyl, Aldicarb, Methomyl, Thiodicarb, Carbofuiran, Carbosulfan, Benfuracarb, Furathiocarb, Propoxur, BPMC, MTMC, MLPC, Carbaryl, Pyrimicarb, Ethiofencarb, Fenoxycarb and the like.

Pyretliroid Type Insecticides: Permetlirin, Cypermetlirin, Deltamethrin, Fenvalerate, Fenpropathrin, Pyrethrin, Allethrin, Tetramethrin, Resmethrin, Dimethrin, Propathrin, Phenothrin, Prothrin, Fluvalinate, Cyfluthrin, Cyhalothrin, Flucythrinate, Ethofenprox, Cycloprotbrin, Tralomethrin, Silafluofen, Acrynatbrin and the like.

Benzoyl urea and other insecticides: Diflubenzuron, Chioriluazuron, Hexaflumuron, Triflumuron, Tetrabenzuron, Flufenoxuron, Flucycloxuron, Buprofezin, Pyriproxyfen, Methoprene, Benzoepin, Diafenthiuron, Acetamiprid, Imidacloprid, Nitenpyram, Fipronyl, Cartap, Thiocyclam, Bensultap, Clilorfenapyr, Emamectinbenzoate, Tebufenozide, Nicotine sulfate, Rotenone, Metaldehyde, Machine oils, BT, Agricultural chemicals for microbial organisms such as insect disease viruses, and the like.

Nematicides: Phenamiphos, Fosthiazate and the like.

Acaricides: Chlorbenzylate, Phenisobromolate, Dicofol, Amitraz, BPPS, Benzomate, Hexythiazox, Fenbutatin oxide, Polynactins, Quinomethionate, CPCBS,' Tetradifon, Avermectin, Milbemnectin, Clofentezin, Cyhexatin, Pyridaben, Fenpyroximate, Tebufenpyrad, Pyrimidifen, Phenothiocarb, Dienochior, Etoxazole, Halfenprox and the like.

Plant growth regulators: Gibberellins (for example, gibberellin A3, gibberellin A4 and gibberellin A7), IAA, NAA and the like.

Best Forms to Implement the Invention: The present invention is further described in detail in reference to Examples. The structures of the compounds of the present invention were determined by IR, NMR and MS.

Example 1 Preparation of 2 4 2 6 -difluorophenyl)-2-thiazolyl]-3-hydroxy-2'-trifluoromethycinnamonitrile

CH

2 -CN 6 00 To a solution of 0.8g (4.2 mmol) of 2-trifluoromethylbenzoic acid in 10 ml of THF was added 0.69g (4.2 mmol) of carbonylbisimidazole, followed by stirring at room temperature for an hour. To the mixture was added 1.0g (4.2 mmol) of 2 -cyanomethyl-4-(2,6-difluorophenyl)thiazole, and then, 0.17g (4.2 mmol) of sodium hydride (60% in oil) in an ice-bath. After stirring at room temperature for an hour, another equivalent of sodium hydride (0.17g, 4.2 mmol 60% in oil) was added, followed by stirring at room temperature overnight. The reaction mixture was poured into ice-water, acidified with dilute hydrochloric acid, and then, extracted with ethyl acetate. The organic layer was concentrated under diminished pressure, followed by chromatography on silica-gel column (ethyl acetate/n-hexane 1/1, as an eluent) to give 1.lg of the title compound. Melting point 170- 172'C.

Representative examples of the compounds of the present invention that can be prepared according to the above process are shown in Table 1. The abbreviation used in the table represents Me: methyl.

Table 1 Compound No. (X 3) nl y1 y 2 M.P. I I T -t I 1 2

F

C I

F

131- 133 3 F F B r -T 171-173 4 F F Me 139-142 F F OM e 197-198 6 F F CF 3 170-172 7 F FT F 6 -F 199-201 8 F F F 6 -Cl 9 F F 3 -F Cl I 1 0 F IF 3 -F F I1I F F 3 -F B r 1 2 F F 3 -F M e 120-122 1 3 F F 3 -F OM e 1 4 F F 3 -F C F 3 1 5 F F 3 -F F 6-F 1 6 F F 3,4,5-F 3 Cl I 1 7 F F 3,4,5-F 3 CF 3 1 8 F Cl C I 1 9 F Cl I

F-

2 0 F Cl I B r.

2 1 F Cl I M e 2 2 F C 1 0 OMe 23 F Cl 1 C F 3 171-173 2 4 Cl CI C1 2 5 Cl CI

F-

2 6 Cl CI B r 2 7 Cl CI M e Compound No. X X 2

(X

3 )n Y Y m.p. C 28 C1 C1 OMe 29 Cl Cl

CF

3 3 0 F Me C 169-171 31 F Me F 32 F Me Br 3 3 F Me Me 135-137 34 F Me OMe F Me

CF

3 162-163 36 F F -F 6-Me 3 7 F F -F 6 -CF 3 38 F F Me 3-F 39 F F Me 4-F F F Me 41 F F

CF

3 3--F 42 F F CF 3 43 Me Me C 216-218 44 Me Me F Me Me Br 4 6 Me Me Me 242-244 47 Me Me OMe 48 Me Me CF 3 194-196 49 CF 3

CF

3 Cl 0 CHF 2 F B r A few examples of compositions of the present invention are described below. Additives and addition ratios are not limited to those in the examples, and can be changed in a wide range. The 'parts" used in the formulation examples are parts by weight.

Example 2 Wettable Powder A compound of the present invention 40 parts Clay 48 parts Sodium dioctylsulfosuccinate 4 parts Sodium lignin sulfonate 8 parts The above compounds were mixed uniformly and pulverized finely to give a wettable powder containing 40% of the active ingredient.

Example 3 Emulsifiable concentrate A compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzene sulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts The above compounds were mixed and dissolved to give an emulsifiable concentrate containing 10% of the active ingredient.

Example 4 Dust A compound of the present invention 10 parts Clay 90 parts The above compounds were mixed uniformly and pulverized finely to give a dust containing of the active ingredient.

Example 5 Granules A compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Sodium dioctylsulfosuccinate 1 part Potassium phosphate 1 part The above compounds were sufficiently pulverized and mixed. Water was added to it for kneading well, followed by granulation and drying to give granules containing 5% of the active ingredient.

Example 6 Flowable concentrate A compound of the present invention 10 parts Polyoxyethylene alkylallyl ether 4 parts Sodium polycarboxylate 2 parts Glycerin 10 parts Xanthane gum 0.2 parts Water 73.8 parts The above compounds were mixed and wet pulverized until the granule size became smaller than 1 i, to give aflowable concentrate containing 10% of the active ingredient.

Example 7 Water dispersible granules A compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Sodium alkylbenzene sulfonate 1 part Sodium lignin sulfonate 8 parts Formaldehyde condensate of sodium alkylbenzene sulfonate 5 parts The above compounds were mixed uniformly and pulverized finely. An appropriate amount of water was added to it for kneading. The resulting clay-like product was granulated and dried to give water dispersible granules containing 40% of the active ingredient.

Availability in Industry: Examples are shown below that formulations containing compounds of the present invention, which were prepared according to such ways as described above, were applied as agricultural and horticultural insecticides and acaricides.

Test Example 1 Effects on Pseudaletia separata Walker According to the instructions of the wettable powder described in the above Example 2, a wettable powder was diluted with water to make the compound concentration 125 ppm. Corn leaves were immersed in the obtained chemical solution for 30 seconds, air dried and placed in a Petri dish containing 5 second instar larvae ofPseudaletia separata Walker. The dish was covered with a glass lid and placed in a thermostatic chamber of temperature 25°C and relative humidity 65%. The mortality was examined 6 days later. The test was carried out by a repeating double trial.

The results show that the following compounds had the mortality of 100 1, 3, 4, 5, 6, 7, 12, 18, 20, 23, 30, 33 and (The compound numbers correspond to those in Table 1.) Control compound A killed none of the larvae at all, and chlorodimeform used as a control killed 40% of them.

Test Example 2 Effects on Aphis gossypii Glover Adults of Aphis gossypii Glover were inoculated on cucumber seedlings planted in a (diameter) pot and 10 days old after the germination. One day later, the adult aphids were removed.

According to the instructions of the emulsifiable concentrate described in the above Example 3, an emulsifiable concentrate was diluted with water to make a compound concentration 125 ppm. The obtained chemical solution was sprayed over the cucumber seedlings infested with the first-instar nymphs. The seedlings were placed in a thermostatic chamber of temperature 25'C and relative humidity 65%. The mortality was examined 6 days later. The test was carried out by a repeating double trial.

The results show that the following compounds had the mortality of 100 1, 3, 4, 5, 6, 7, 12,20, 23, 33 and The known compounds shown below and used as controls had the following mortalities: Control Compound A: 44% Control Compound B: 0% Control Compound C: 46% Pyrimicarb: 9% Control Compound A A compound disclosed in Japanese Patent Laid-open No. Sho 55-154963 C1 Control Compound B A compound disclosed in Japanese Patent Laid-open No. Sho 55-154963 Control Compound C A compound disclosed in EP 189960 N H

Claims

13- THE CLAIMS DEFINING THE INVENTION ARE AS FOLLOWS: 1. A compound represented by Formula (1) (1) wherein X 1 X 2 and X 3 are, each independently halogen, C 1 -3 alkyl or C 1 -3 haloalkyl; n is 0 or an integer of 1 to 3; YI is halogen, C 1 -3 alkyl, C1- 4 alkoxy or CI- 3 haloalkyl; and Y 2 is hydrogen, halogen, C 1 -3 alkyl, C 1 -4 alkoxy or C 1 3 haloalkyl, when used as an insecticide or acaricide. 2. A compound according to Claim 1, in which Xi and X 2 are, each independently, fluorine, chlorine, methyl or trifluoromethyl, when used as an insecticide or an acaricide. 3. A method of controlling insect and acarid pests comprising applying one or more compounds of Formula (1) H Y, S X, \2 0 *0 .*oo .0 000. 04..0 0 0 0000 wherein X 1 X 2 and X 3 are, each independently halogen, C 1 -3 alkyl or C1- 3 haloalkyl; n is 0 or an integer of 1 to 3; Y 1 is halogen, C1- 3 alkyl, C1- 4 alkoxy or C1- 3 haloalkyl; and V P:\OPER\Kbn\22250-01 clims.doc-04/12/03 -14- Y 2 is hydrogen, halogen, Ci-3 alkyl, C 1 -4 alkoxy or CI- 3 haloalkyl, to said pests or their habitat. 4. A method according to Claim 3, in which X 1 and X 2 in Formula are, each independently, fluorine, chlorine, methyl or trifluoromethyl. A compound according to claim 1, when used as an insecticide or acaricide, substantially as hereinbefore described with reference to the Examples. 6. A method of controlling insect and acarid pests according to claim 3, substantially as hereinbefore described with reference to the Examples. DATED this 4 th day of December, 2003 Nippon Soda Co., Ltd. By DAVIES COLLISON CAVE Patent Attorneys for the Applicants 9* S S Se S S SSSS Abstract A compound represented by Formula (1) (1) (wherein X 1 X 2 and X 3 are, each independently, halogen, C 1 -3 alkyl or C 1 -3 haloalkyl; n is 0 or an integer of 1 to 3; YI is halogen, C 1 -3 alkyl, C1- 4 alkoxy or C 1 -3 haloalkyl; and Y 2 is hydrogen, halogen, C1- 3 alkyl, Cl- 4 alkoxy or C 1 -3 haloalkyl), and a pest controlling agent containing one or more of the said compounds as active ingredients.