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Ep 1380209 B1 (19) & (11) EP 1 380 209 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A01N 41/10 (2006.01) A01N 37/30 (2006.01) 05.09.2012 Bulletin 2012/36 (86) International application number: (21) Application number: 02717180.0 PCT/JP2002/003780 (22) Date of filing: 16.04.2002 (87) International publication number: WO 2002/087334 (07.11.2002 Gazette 2002/45) (54) PEST CONTROL AGENT COMPOSITION AND METHOD OF USING THE SAME SCHÄDLINGSBEKÄMPFUNGSZUSAMMENSETZUNG UND VERFAHREN ZU IHRER VERWENDUNG COMPOSITION D’AGENTS PESTICIDES ET PROCEDE D’UTILISATION (84) Designated Contracting States: • MORIMOTO, Masayuki AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU Kawachinagano-shi, Osaka 596-0024 (JP) MC NL PT SE TR • KODAMA, Hiroshi Hashimoto-shi, Wakayama 648-0063 (JP) (30) Priority: 17.04.2001 JP 2001118840 • NISHIMATSU, Tetsuyosi 26.04.2001 JP 2001129588 Kawachinagano-shi, Osaka 586-0094 (JP) (43) Date of publication of application: (74) Representative: Grünecker, Kinkeldey, 14.01.2004 Bulletin 2004/03 Stockmair & Schwanhäusser Leopoldstrasse 4 (73) Proprietor: NIHON NOHYAKU CO., LTD. 80802 München (DE) Tokyo 103-8236 (JP) (56) References cited: (72) Inventors: EP-A2- 0 919 542 JP-A- 2001 064 268 • SAKATA, Kazuyuki JP-A- 2001 131 141 JP-A- 2001 158 764 Kawachinagano-shi, Osaka 586-0022 (JP) JP-A- 2001 240 580 Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 380 209 B1 Printed by Jouve, 75001 PARIS (FR) EP 1 380 209 B1 Description TECHNICAL FIELD 5 [0001] The present invention relates to a composition for noxious organisms-controlling agent having a synergistic effect and a method for using said composition, which comprises a phthalamide derivative being useful as an insecticide or acaricide and one or more compounds selected from the compounds having insecticidal, acaricidal or nematocidal activity. 10 BACKGROUND ART [0002] The phthalamide derivatives represented by general formula (I) are known compounds disclosed in JP-A- 11-240857, JP-A-2001-131141. JP-A-2001-064268, JP- A-2001-158764 and JP- A-2001-240580, wherein it is mentioned that these compounds have an insecticidal or acaricidal activity. 15 [0003] On the other hand, the compounds having insecticidal, acaricidal or nematocidal activity, as the second active ingredient of the present invention, are known compounds as disclosed in The Pesticide Manual Eleventh Edition 1997, etc. DISCLOSURE OF THE INVENTION 20 [0004] There exist many noxious organisms which are difficult or impossible to control by the use of a single member selected from phthalamide derivatives and the insecticidal, acaricidal or nematocidal compounds. Accordingly, it is expected that discovery of the means and method for the effective control of such noxious organisms will lead to a more effective production of crop plants. 25 [0005] With the aim of solving the problem mentioned above, the present inventors have conducted extensive studies. As a result, it has been found that a plurality of noxious organisms can be controlled effectively by the combined use of one or more compounds selected from phthalamide derivatives and one or more compounds selected from the insec- ticidal, acaricidal or nematocidal compounds. The present invention has been accomplished on the basis of this finding. [0006] The present invention relates to a composition for noxious organisms-controlling agent comprising, as active 30 ingredients thereof, one or more compounds selected from 2N-(1,1-dimethyl-2-methylthioethyl)-3-iodo-N1-(2-methyl- 4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl) phthalamide. 2-(1,1-N dimethyl-2-methylsulfonylethyl)-3-iodo- N1-(2-methyl-4-(1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl)phenyl)phthalamide or N2-(1,1-dimethyl-2-methylsulfinyle- thyl)-3-iodo-N1-(2-methyl-4-{1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl}phenyl)phthalamide; and 35 one or more compounds selected from compounds having an insecticidal, acaricidal or nematocidal activity; and to a method for using said composition. [0007] The noxious organisms-controlling agent of the present invention exhibits a marked effect even when dosage thereof is so low that any of the ingredients constituting said agent can exhibit no effect at such a low dosage if used singly, and exhibits a marked controlling effect against noxious organisms and agent- resistant noxious organisms which 40 cannot be controlled with any of the single ingredients. MODE FOR PRACTICE OF THE ENVENTION [0008] In some cases, the phthalamide derivative of the present invention may have an asymmetric carbon atom or 45 an asymmetric center in the structural formula thereof, and may have two or more optical isomers. The present invention involves all such optical isomers and mixtures consisting of the optical isomers at arbitrary ratios. In some cases, the present invention involves salts, hydrates and the like of these compounds. [0009] The phthalamide derivatives can be obtained by using the compounds and production processes disclosed in JP-A-11-240857 and JP-A-2001-131141. 50 [0010] The phthalamide derivatives of the invention are the following : N 2-(1,1-dimethyl-2-methylthioethyl)-3-iodo-N1- {2-methyl-4-(1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-ohthalamide, N’-(1,1-dimethyl-2-methylsulfonylethyl)-3- iodo-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-phenyl}phthalamide and 2N-(1,1-dimethyl-2-methyl- sulfinylethyl)-3-iodo-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-phenyl}phthalamide. [0011] In Table 1, the compounds of the present invention are listed. 55 2 EP 1 380 209 B1 5 10 Table 1 (Z1 = Z2 =O) No R1 R2 R3 Xn Ym Property mp °C 15 129 C(CH3)2CH2SCH3 HH3-I2-CH3-4-C3F7-i 205-206 130 C(CH3)2CH2SO2CH3 HH3-I2-CH3-4-C3F7-i 90-95 131 C(CH3)2CH2SOCH3 HH3-I2-CH3-4-C3F7-i 88-90 20 [0012] As the compounds having an insecticidal, acaricidal or nematocidal activity, which the composition for noxious organisms-controlling agent of the present invention comprises, insecticidal compounds such as chloronicotinyl com- pounds, carbamate compounds, pyrethroid compounds, macrolide compounds, phosphorus compounds and the like can be referred to. Examples thereof include the following compounds indicated by their general names, however, the 25 present invention is by no means limited by these compounds: acetamiprid, pymetrozine, fenitrothion, acephate, carbaryl, methomyl, cartap, cyhalothrin, ethofenprox, tefluben- zuron, flufenoxuron, tebufenozide, fenpyroximate, pyridaben, imidacloprid, buprofezin, BPMC (fenobucarb), malathion, methidathion, fenthion, diazinon, oxydeprofos, vamidothion, ethiophencarb, pirimicarb, permethrin, cy- permethrin, bifenthrin, halfenprox, silafluofen, nitenpyram, chlorfluazuron, methoxyfenozide, tebufenpyrad, pyrimid- 30 ifen, dicofol, propargite, hexythiazox, clofentezine, spinosad, milbemectin, BT (bacillus thuringiensis), indoxacarb, chlorfenapyr, fipronil, etoxazole, acequinocyl, pirimiphos-methyl, acrinathrin, quinomethionate, chlorpyrifos, aver- mectin, emamectin-benzoate, fenbutatin oxide, terbufos, ethoprophos, cadusafos, fenamiphos, fensulfothion, DSP, dichlofenthion, fosthiazate, oxamyl, isamidofos, fosthietan, isazofos, thionazin, benfuracarb, spirodiclofen, ethiofen- carb, azinphos-methyl, disulfoton, methiocarb, oxydemetonmethyl, parathion, cyfluthrin, beta- cyfluthrin, tebupyrim- 35 fos, spiromesifen, endosulfan, amitraz, tralomethrin, acetoprole, ethiprole and the like. [0013] Further, it is also possible to use the compounds mentioned above in combination with insecticides, acaricides and nematocides having the following general names or chemical names, or those disclosed in the following Patent 40 Kokai gazettes, etc.: ethion, trichlorfon (DEP), metamidophos, dichlorvos (DDVP), mevinphos, monocrotophos, dimethoate, formothion, mecarbam, thiometon, disulfoton, naled (BRP), methylparathion, cyanophos, diamodafos, albendazole, oxibenda- zole, fenbendazole, oxfendazole, propaphos, sulprofos, prothiofos, profenofos, isophenphos, temephos, ph- enthoate, dimethylvinphos, chlorfenvinphos, tetrachlorvinphos, phoxim, isoxathion, pyraclofos, chlorpyrifos- methyl, 45 pyridafenthion, phosalone, phosmet, dioxabenzofos, quinalphos, pyrethrins, allethrin, prallethrin, resmethrin, per- methrin, tefluthrin, fenpropathrin, alpha- cypermethrin, lambda-cyhalothrin, deltamethrin, fenvalerate, esfenvalerate, flucythrinate, fluvalinate, cycloprothrin, thiodicarb, aldicarb, alanycarb, metolcarb, xylylcarb, propoxur, fenoxycarb, fenothiocarb, bifenazate, carbofuran, carbosulfan, furathiocarb, diafenthiuron, diflubenzuron, hexaflumuron, no- valuron, lufenuron, chlorfluazuron, cyhexatin, Oleic acid sodium salt, Potassium oleate, methoprene, hydroprene, 50 binapacryl, amitraz, chlorobenzilate, brompropylate, tetradifon, bensultap, benzoximate, chromafenozide, endosul- fan, diofenolan, tolfenpyrad, triazamate, nicotine-sulfate, thiacloprid, thiamethoxam, clothianidin, dinotefuran (MT I- 446), fluazinam, pyriproxyfen, hydramethylnon, cyromazine, TPIC (tripropylisocyanurate), thiocyclam, fenazaquin, polynactins, azadirachtin, rotenone, Hydroxy propyl starch, mesulfenfos, phosphocarb, isoamidofos, aldoxycarb, metam-sodium,
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