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WO 2015/028034 Al 5 March 2015 (05.03.2015) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2015/028034 Al 5 March 2015 (05.03.2015) P O P C T (51) International Patent Classification: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, A01N 53/00 (2006.01) A01N 47/02 (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, A01N 43/90 (2006.01) A01P 7/00 (2006.01) HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, A01N 57/ (2006.01) KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (21) International Application Number: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, PCT/DK20 14/050264 SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (22) International Filing Date: TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 1 September 2014 (01 .09.2014) ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (30) Priority Data: TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, PA 2013 00494 2 September 2013 (02.09.2013) DK TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (71) Applicant: CHEMINOVA A S [DK/DK]; Thyboranvej LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, 78, DK-7673 Harbo0re (DK). SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). (72) Inventor: 0STERGAARD, Niels; R0dem0llevej 20, DK- 7660 Bffikmarksbro (DK). Declarations under Rule 4.17 : (74) Agents: RASMUSSEN, Torben Ravn et al; Awapatent — as to applicant's entitlement to apply for and be granted a A/S, Rigensgade 11, DK-13 16 K0benhavn K (DK). patent (Rule 4.1 7(H)) (81) Designated States (unless otherwise indicated, for every Published: kind of national protection available): AE, AG, AL, AM, — with international search report (Art. 21(3)) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, o 00 (54) Title: COMBINATION OF 2,3,5, 6-TETRAFLUORO-4-METHYLBENZYL (Z)-(l R)-CIS-3-(2-CHLORO-3,3,3-TRIFLUORO-l © -PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE WITH AT LEAST ONE INSECTICIDE, ACARICIDE, NEMATICIDE AND/OR FUNGICIDE. o (57) Abstract: Presented are new pesticidal mixtures comprising 2,3,5, 6-tetrafluoro-4- methylbenzyl(Z)-(lR)-cis-3-(2-chloro-3,3,3- trifluoro-l-propenyl)-2,2- dimethylcyclopropanecarboxylate and one or more of compound(s) (II) which is an insecticide, acaricide, nematicide and/or fungicide. The invention relates also to methods and use of these mixtures for controlling harmful pests such as o insects, arachnids, nematodes and fungie.g.in and on plants, and for protecting such plants being infested with pests and also for pro - tecting seeds. COMBINATION OF 2,3,5,6-TETRAFLUORO-4-METHYLBENZYL (Z)-(1 R)-CIS-3-(2-CHLORO-3,3,3-TRIFLUORO-1 -PROPENYL)-2,2-DIMETHYLCYCLOPROPANECARBOXYLATE WITH AT LEAST ONE INSECTICIDE, ACARICIDE, NEMATODE AND/OR FUNGICIDE Introduction The invention relates to new pesticidal mixtures comprising a pyrethroid compound (I) which is 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(\R)-cis-3-(2- chloro-3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate and one or more compounds (II) chosen among insecticides, acaricides, nematicides and/or fungicides. The invention relates also to a method and use of these mixtures for controlling harmful pests (e.g. insects, arachnids, nematodes and fungi) e.g. in and on plants and non-crops, and for protecting such plants being infested with pests and also for protecting seeds. Background One typical problem arising in the field of pest control lies in the need to reduce the dosage rates of the active ingredient in order to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing effective pest control. Another problem encountered concerns the need to have available pest control agents which are effective against a broad spectrum of pests. There also exists the need for pest control agents that combine knock-down activity with prolonged control, that is, fast action with long lasting action. Another difficulty in relation to the use of pesticides is that the repeated and exclusive application of an individual pesticidal compound leads in many cases to a rapid selection of pests which have developed natural or adapted resistance against the active compound in question. Therefore there is a need for pest control agents that help prevent or overcome resistance. It was therefore an object of the present invention to provide pesticidal mixtures which solves at least one of the discussed problems such as reducing the dosage rate, enhancing the spectrum of activity or combining knock-down activity with prolonged control or as to resistance management. It has been found that this object is in part or in whole achieved by the combination of active compounds defined at the outset. Moreover, it has been found that simultaneous, that is joint or separate, application of an active compound (I) and one or more compounds (II) or successive application of an active compound (I) and one or more compounds (II) allows enhanced control of pests compared to the control rates that are possible with the individual compounds. The pesticidal active compound tefluthrin is a racemic mixture comprised of mainly two isomers out of 8 possible due to the Z/E configuration on the vinyl group and the two chiral centers on the cyclopropane ring (IRS, RS , i.e. present in the molecule 2,3,5,6-tetrafluoro-4-methylbenzyl 3-(2-chloro-3,3,3- trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate. One of these 8 isomers being the compound (I). Tefluthrin is primarily a mixture of the two compounds (Z)-( \R)-cis-3 -(2-chloro-3,3,3-trifluoro- 1-propenyl)-2,2- dimethylcyclopropanecarboxylate and (Z)-(l,S)-czs-3-(2-chloro-3,3,3-trifluoro-l- propenyl)-2,2-dimethylcyclopropanecarboxylate; i.e. two cis-isomers. On a commercial scale, tefluthrin is produced according to methods that provide such mixture, and the single most active isomer is not easily separated. The use of tefluthrin in crop protection is well known e.g. as described in British Crop Protection Conference Pests and Diseases,(l), p . 97-106 (1986). It is known that the pesticidal effect of tefluthrin is found primarily in one of the isomers, i.e. compound (I), as described in British Crop Protection Conference Pests and Diseases, (1), p . 199-206 (1986). One would expect that when combining tefluthrin with another pesticide, the same combination would require approximately half the amount of the most active isomer (i.e. compound (I)) to provide the same pesticidal effect. However, it has now surprisingly been found that an improved effect is observed when substituting tefluthrin (including any of the other isomers) with the compound (I), preferably substantially free of any of the others isomers of 2,3,5,6-tetrafluoro-4-methylbenzyl 3-(2-chloro- 3,3,3-trifluoro-l-propenyl)-2,2-dimethylcyclopropanecarboxylate. That is, it has been found that an improved synergistic effect is present for pesticidal mixtures comprising the compound (I) over the same mixtures comprising tefluthrin. The unexpected finding has several important implications, e.g. both economical but also environmental in that the pesticidal mixtures as herein described preferably need only to be applied at a lower dose and advantageously without the presence of potentially detrimental isomers. It is a standard demand in crop protection to achieve an optimal effect with active ingredients at the lowest dosage rate required while simultaneously keeping the pollution of the environment as low as possible. Description of the invention The present invention relates to a mixture comprising compound (I) which is 2,3,5,6-tetrafluoro-4-methylbenzyl (Z)-(\R)-cis-3-(2-chloro-3,3,3-trifluoro- 1- propenyl)-2,2-dimethylcyclopropanecarboxylate and one or more compound(s) (II) which is either an insecticide, nematicide, acaricide or fungicide. One aspect of the invention relates to a mixture comprising, as pesticidal active ingredients, the compound (I) and just one other compound (II) which is an insecticide, nematicide, acaricide or fungicide, i.e. a mixture containing the compound (I) and one other compound (II) which is an insecticide, nematicide, acaricide or fungicide as the sole active ingredients. Preferably the compound (II) is an insecticide, nematicides or acaricide and most preferably an insecticide or acaricide. Another apect of the invention relates to a mixture comprising, as pesticidal active ingredients, the compound (I) and just two other compounds (II) which are selected among insecticides, nematicides, acaricides and/or fungicides, i.e. a mixture containing the compound (I) and two other compounds (II) which are selected among insecticides, nematicides, acaricides and/or fungicides as the sole active ingredients. Preferably at least one of the two compounds (II) is a insecticide or an acaricide. More preferably the second of the two compounds (II) is chosen among insecticides, nematicides or acaricides; with insecticides and acaricides being of particular use. In another aspect the two compounds (II) are both insecticides, nematicides, acaricides or fungicides, more preferably the two compounds (II) are both insecticides, nematicides or acaricides and most preferably the two compounds (II) are both insecticides or acaricides.
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