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Wo 2011/017351 A2 (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 10 February 2011 (10.02.2011) WO 2011/017351 A2 (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every AOlN 43/54 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (21) International Application Number: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, PCT/US20 10/044285 DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 3 August 2010 (03.08.2010) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (26) Publication Language: English SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 61/23 1,483 5 August 2009 (05.08.2009) US (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant (for all designated States except US): E. I. DU GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, PONT DE NEMOURS AND COMPANY [US/US]; ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, 1007 Market Street, Wilmington, DE 19898 (US). TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (72) Inventors; and LV, MC, MK, MT, NL, NO, PL, PT, RO, SE, SI, SK, (75) Inventors/Applicants (for US only): HOLYOKE JR, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Caleb, William [US/US]; 120 Country Club Drive, GW, ML, MR, NE, SN, TD, TG). Newark, Delaware 1971 1 (US). ZHANG, Wenming [CN/US]; 2 1 Charles Pointe, Newark, Delaware 19702 Published: (US). TONG, My-Hanh, Thi [US/US]; 4 Orchid Drive, — without international search report and to be republished Bear, Delaware 19701 (US). upon receipt of that report (Rule 48.2(g)) (74) Agent: KUCHARCZYK, Roman; E. I. du Pont de Nemours and Company, Legal Patent Records Center, 4417 Lancaster Pike, Wilmington, DE 19805 (US). (54) Title: MIXTURES OF MESOIONIC PESTICIDES (57) Abstract: Disclosed are compositions comprising (a) at least one compound selected from compounds of Formula (1), N-ox- ides, and salt thereof, wherein R 1 is phenyl optionally substituted with up to 5 substituents independently selected from R3, or 3 2 pyridinyl optionally substituted with up to 4 substituents independently selected from R ; R is C 1-C4 haloalkyl; or thiazolyl, pyridinyl or pyrimidinyl, each optionally substituted with up to 2 substituents independently selected from the group consisting of 3 halogen and C 1-C4 alkyl; each R is independently halogen, cyano, C 1-C4 alkyl, C 1-C4 haloalkyl, C 1-C4 alkoxy, C 1-C4 haloalkoxy, C(R4)=NOR 4 or Q; each R4 is independently C1-C4 alkyl; Z is CH=CH or S; and each Q is independently phenyl or pyridinyl, each optionally substituted with up to 3 substituents independently selected from the group consisting of halogen, cyano, Ci-C alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy; and (b) at least one invertebrate pest control agent. Also disclosed are meth ods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a composition of the invention. TITLE MIXTURES OF MESOIONIC PESTICIDES FIELD OF THE INVENTION This invention relates to pesticidal mixtures comprising certain pyrimidinium compounds, their //-oxides, and salts, and at least one other invertebrate pest control agent, suitable for agronomic, nonagronomic and animal health uses, and methods of their use for controlling invertebrate pests such as arthropods in both agronomic and nonagronomic environments, and for treatment of parasite infections in animals or infestations in the general environment. BACKGROUND OF THE INVENTION The control of invertebrate pests is extremely important in achieving high crop efficiency. Damage by invertebrate pests to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of invertebrate pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, turf, wood products, and public health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different sites of action. The control of animal parasites in animal health is essential, especially in the areas of food production and companion animals. Existing methods of treatment and parasite control are being compromised due to growing resistance to many current commercial parasiticides. The discovery of more effective ways to control animal parasites is therefore imperative. U.S. Patent No. 5,151,427 discloses mesoionic pyrimidinium compounds of Formula i as anthelmintics wherein, inter alia, R1 and R2 are independently C - C alkyl, R3 is a heteroaromatic 6- 4 5 membered ring, and R and R are independently hydrogen or - C4 alkyl. The mixtures of the present invention are not disclosed in this publication. SUMMARY OF THE INVENTION This invention is directed to a composition comprising (a) at least one compound selected from compounds of Formula 1 (including all stereoisomers), //-oxides, and salts thereof, wherein R1 is phenyl optionally substituted with up to 5 substituents independently selected from R3, or pyridinyl optionally substituted with up to 4 substituents independently selected from R3; 2 R is C1- C4 haloalkyl; or thiazolyl, pyridinyl or pyrimidinyl, each optionally substituted with up to 2 substituents independently selected from the group consisting of halogen and C1- C4 alkyl; 3 each R is independently halogen, cyano, C1- C4 alkyl, C1- C4 haloalkyl, C1- C4 4 4 alkoxy, C C4 haloalkoxy, C(R )=NOR or Q; 4 each R is independently C1- C4 alkyl; Z is CH=CH or S; and each Q is independently phenyl or pyridinyl, each optionally substituted with up to 3 substituents independently selected from the group consisting of halogen, cyano, C1- C4 alkyl, C1- C4 haloalkyl, C1- C4 alkoxy and C1- C4 haloalkoxy; and (b) at least one invertebrate pest control agent selected from the group consisting of abamectin, acetamiprid, amitraz, avermectin, azadirachtin, bensultap, bifenthrin, buprofezin, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, metaflumizone, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, phosmet, pymetrozine, pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, tebufenozide, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate, triflumuron, Bacillus thuringiensis delta- endotoxins, all strains of Bacillus thuringiensis and all strains o Nucleo polyhydrosis viruses. This invention is also directed to aforesaid composition wherein component (a) is selected from at least one compound of Formula 1 (including all stereoisomers). This invention is also directed to the compositions described above, and further herein, 1 2 1 provided that (a) when R is unsubstituted phenyl and R is CF3, then Z is S; (b) when R is 2-fiuorophenyl and R2 is 2-chloro-5-thiazolyl, then Z is S; and (c) when R 1 is 2-fluorophenyl or 3-(trifluoromethoxy)phenyl and R2 is 6-chloro-3-pyridinyl, then Z is CH=CH. This invention also provides a composition comprising any of the compositions described above and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. In one embodiment, this invention also provides a composition for controlling an invertebrate pest comprising the composition described above and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, said composition further comprising at least one additional biologically active compound or agent. This invention is also directed to a composition comprising (a) at least one compound selected from compounds of Formula 1, JV-oxides, and salts thereof, 1 wherein R1 is phenyl optionally substituted with up to 5 substituents independently selected from R3, or pyridinyl optionally substituted with up to 4 substituents independently selected from R3; 2 R is C1- C4 haloalkyl; or thiazolyl, pyridinyl or pyrimidinyl, each optionally substituted with up to 2 substituents independently selected from the group consisting of halogen and C1- C4 alkyl; 3 each R is independently halogen, cyano, C1- C4 alkyl, C1- C4 haloalkyl, C1- C4 4 4 alkoxy, C1- C4 haloalkoxy, C(R )=NOR or Q; 4 each R is independently C1- C alkyl; Z is CH=CH or S; and each Q is independently phenyl or pyridinyl, each optionally substituted with up to 3 substituents independently
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