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WO 2012/080415 Al 21 June 2012 (21.06.2012) P O P C T

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WO 2012/080415 Al 21 June 2012 (21.06.2012) 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 2012/080415 Al 21 June 2012 (21.06.2012) P O P C T (51) International Patent Classification: (74) Agent: THWAITE, Jonathan; Syngenta Crop Protection, A 43/36 (2006.01) A01N 47/06 (2006.01) Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein A 43/40 (2006.01) A01N 51/00 (2006.01) (CH). A 43/90 (2006.01) A01P 9/00 (2006.01) (81) Designated States (unless otherwise indicated, for every A01N 57/ (2006.01) A01P 7/04 (2006.01) kind of national protection available): AE, AG, AL, AM, A0 43/56 (2006.01) A01P 7/02 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, A0 53/00 (2006.01) A01P 7/00 (2006.01) CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, A0 43/707 (2006.01) A01P 5/00 (2006.01) DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, (21) International Application Number: HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, PCT/EP20 11/072946 KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (22) International Filing Date: OM, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, 15 December 201 1 (15. 12.201 1) SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, (25) Filing Language: English TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (26) Publication Language: English (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (30) Priority Data: GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, 10195199.4 15 December 2010 (15. 12.2010) EP UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, (71) Applicant (for all designated States except US): SYN- TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, GENTA PARTICIPATIONS AG [CH/CH]; Schwar- DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, zwaldallee 215, CH-4058 Basel (CH). LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (72) Inventors; and GW, ML, MR, NE, SN, TD, TG). (75) Inventors/Applicants (for US only): RENOLD, Peter [CH/CH]; Syngenta Crop Protection, Munchwilen AG, Declarations under Rule 4.17 : Schaffhauserstrasse, CH-4332 Stein (CH). CASSAYRE, — as to applicant's entitlement to apply for and be granted a Jerome Yves [FR/CH]; Syngenta Crop Protection, Munch patent (Rule 4.1 7(H)) wilen AG, Schaffhauserstrasse, CH-4332 Stein (CH). EL QACEMI, Myriem [FR/CH]; Syngenta Crop Protection, Published: Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein — with international search report (Art. 21(3)) (CH). PABBA, Jagadish [IN/IN]; Syngenta Biosciences, — before the expiration of the time limit for amending the Private Limited, Santa Monica Works, Corlim Ilhas Goa, claims and to be republished in the event of receipt of Goa 403 110 (IN). PITTERNA, Thomas [AT/CH]; Syn amendments (Rule 48.2(h)) genta Crop Protection, Munchwilen AG, Schaffhauser strasse, CH-4332 Stein (CH). (54) Title: PESTICIDAL MIXTURES < (I) o 00 (57) Abstract: The present invention relates to pesticidal mixtures comprising a component A and a component B, wherein compon © 1 2 1 ent A is a compound of formula I wherein one of Y and Y is S, SO or SO2 and the other is CH2; L is a direct bond or methylene; A and A2 are C-H, or one of A 1 and A2 is C-H and the other is N; R 1 is hydrogen or methyl; R2 is chlorodifluoromethyl or trifluoro- o methyl; R3 is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, or 3,4,5-trichloro- phenyl, 3,5-dichloro-4-fluoro- phenyl, or 3,5-bis-trifluoromethylphenyl; R4 is methyl or chlorine; R5 is hydrogen; or R4 and R5 together form a bridging 1,3- butadiene group; and wherein component B is an insecticide. The invention also relates to methods of controlling insects, acarines, o nematodes or molluscs which comprises applying to a pest, to a locus of a pest, or to a plant susceptible to attack by a pest a combin - ation of components A and B. PESTICIDAL MIXTURES The present invention relates to mixtures of pesticidally active ingredients and to methods of using the mixtures in the field of agriculture. WO20 10/020522 discloses that certain dihydropyrrole compounds have insecticidal activity. The present invention provides pesticidal mixtures comprising a component A and a component B, wherein component A is a compound of formula I wherein 1 2 one of Y and Y is S, SO or S0 2 and the other is CH2; L is a direct bond or methylene; A1 and A2 are C-H, or one of A1 and A2 is C-H and the other is N; R 1 is hydrogen or methyl; R2 is chlorodifluoromethyl or trifluoromethyl; R is 3,5-dibromo-phenyl, 3,5-dichloro-phenyl, 3,4-dichloro-phenyl, or 3,4,5-trichloro- phenyl, 3-chloro-5-trifluoromethyl-phenyl, 3,5-dichloro-4-fluoro-phenyl, or 3,5-bis- trifluoromethylphenyl; R4 is methyl or chlorine; R5 is hydrogen; or R4 and R5 together form a bridging 1,3 -butadiene group; and component B is a compound selected from a) a pyrethroid selected from the group consisting of permethrin, cypermethrin, fenvalerate, esfenvalerate, deltamethrin, cyhalothrin, lambda-cyhalothrin, gamma- cyhalothrin, bifenthrin, fenpropathrin, cyfluthrin, tefluthrin, ethofenprox, natural pyrethrin, tetramethrin, S-bioallethrin, fenfluthrin, prallethrin and 5-benzyl-3-furylmethyl-(E)-(lR,3S)-2,2-dimethyl- 3-(2-oxothiolan-3-ylidenemethyl)cyclopropane carboxylate; b) an organophosphate selected from the group consisting of sulprofos, acephate, methyl parathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon, fenamiphos, monocrotophos, profenofos, triazophos, methamidophos, dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos, fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl, pirimiphos-ethyl, fenitrothion, fosthiazate and diazinon; c) a carbamate selected from the group consisting of pirimicarb, triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb, aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur, methomyl and oxamyl; d) a benzoyl urea selected from the group consisting of diflubenzuron, triflumuron, hexaflumuron, flufenoxuron, lufenuron and chlorfluazuron; e) an organic tin compound selected from the group consisting of cyhexatin, fenbutatin oxide and azocyclotin; f) a pyrazole selected from the group consisting of tebufenpyrad and fenpyroximate; g) a macrolide selected from the group consisting of abamectin, emamectin (e.g. emamectin benzoate), ivermectin, milbemycin, spinosad, azadirachtin and spinetoram; h) an organochlorine compound selected from the group consisting of endosulfan (in particular alpha-endosulfan), benzene hexachloride, DDT, chlordane and dieldrin; i) an amidine selected from the group consisting of chlordimeform and amitraz; j) a fumigant agent selected from the group consisting of chloropicrin, dichloropropane, methyl bromide and metam; k) a neonicotinoid compound selected from the group consisting of imidacloprid, thiacloprid, acetamiprid, nitenpyram, dinotefuran, thiamethoxam, clothianidin, and nithiazine; 1) a diacylhydrazine selected from the group consisting of tebufenozide, chromafenozide and methoxyfenozide; m) a diphenyl ether selected from the group consisting of diofenolan and pyriproxyfen; n) indoxacarb; o) chlorfenapyr; p) pymetrozine; q) spirotetramat, spirodiclofen and spiromesifen; r) a diamide selected from the group consisting of flubendiamide, chlorantraniliprole (Rynaxypyr®) and cyantraniliprole; s) sulfoxaflor; t) metaflumizone; u) fipronil and ethiprole; v) pyrifluqinazon; and w) buprofezin; x) flonicamid; y) 4-[(6-Chloro-pyridin-3-ylmethyl)-(2,2-difluoro-ethyl)-amino]-5H-furan-2-one. In addition, component B may be a nematicidally active biological agents. The nematicidally active biological agent refers to any biological agent that has nematicidal activity. The biological agent can be any type known in the art including bacteria and fungi. The wording "nematicidally active" refers to having an effect on, such as reduction in damage caused by, agricultural-related nematodes. The nematicidally active biological agent can be a bacterium or a fungus. Preferably, the biological agent is a bacterium. Examples of nematicidally active bacteria include Bacillus firmus, Bacillus cereus, Bacillus subtilis, and Pasteuria penetrans, preferably Bacillus firmus, Bacillus subtilis, and Pasteuria penetrans. A suitable Bacillus firmus strain is strain CNCM 1-1582 which is commercially available as BioNem™ A suitable Bacillus cereus strain is strain CNCM I- 1562. Of both Bacillus strains more details can be found in US 6,406,690. It has now been found, surprisingly, that the active ingredient mixture according to the invention not only delivers about the additive enhancement of the spectrum of action with respect to the pest to be controlled that was in principle to be expected but achieves a synergistic effect which can extend the range of action of the component A and of the component B in two ways. Firstly, the rates of application of the component A and of the component B are lowered whilst the action remains equally good. Secondly, the active ingredient mixture still achieves a high degree of pest control, sometimes even where the two individual components have become totally ineffective in such a low application rate range. This allows increased safety in use. However, besides the actual synergistic action with respect to pest control, the pesticidal compositions according to the invention can have further surprising advantageous properties which
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