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WO 2012/106495 Al 9 August 2012 (09.08.2012) P O P C T

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WO 2012/106495 Al 9 August 2012 (09.08.2012) 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 2012/106495 Al 9 August 2012 (09.08.2012) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07D 471/04 (2006.01) A01N 43/90 (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/US2012/023583 DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, (22) International Filing Date: HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, KR, 2 February 2012 (02.02.2012) KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (25) Filing Language: English OM, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, 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: 61/439,129 3 February 201 1 (03.02.201 1) (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, RW, SD, SL, SZ, TZ, Pont de Nemours and Company [US/US]; 1007 Market UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, Street, Wilmington, Delaware 19898 (US). 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, (72) Inventors; and LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, 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, Ne GW, ML, MR, NE, SN, TD, TG). wark, Delaware 1971 1 (US). TONG, My-Hanh, Thi [US/US]; 4 Orchid Drive, Bear, Delaware 19701 (US). Published: ZHANG, Wenming [CN/US]; 2 1 Charles Pointe, Newark, — with international search report (Art. 21(3)) Delaware 19702 (US). (74) Agent: KUCHARCZYK, Roman; E. I. du Pont de Nemours and Company, Legal Patent Records Center, 4417 Lancaster Pike, Wilmington, Delaware 19808 (US). (54) Title: MESOIONIC PESTICIDES (57) Abstract: Disclosed are compounds of 1 (R )n Formula 1, each R is independently halogen, cyano, C 1 alkyl, C 1 haloalkyl, cyc- loalkyl, halocycloalkyl, C 1 alkoxy, C 1 haloalkoxy, C 1 alkylthio or C 1 haloalkylthio; each R2 is independently halo gen, cyano, C 1 alkyl, C 1 haloalkyl, cycloalkyl, halocycloalkyl, C 1 a l koxy, C 1 haloalkoxy, C 1 alkylthio, C 1 haloalkylthio, C 1 alkylsulfinyl, C 1 haloalkylsulfinyl, C 1 alkylsulfonyl or C 1 haloalkylsulfonyl; ( 1 ) wherein n is 0, 1 or 2; and m is 1, 2 or 3. Also disclosed are composi tions containing the compounds of Formula 1 and methods for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically ef fective amount of a compound or a composi tion of the invention. o o o TITLE MESOIONIC PESTICIDES FIELD OF THE INVENTION This invention relates to certain pyrimidinium compounds, their compositions suitable for agronomic and nonagronomic uses, and methods of their use for controlling invertebrate pests such as arthropods in both agronomic and nonagronomic environments. 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. PCT Patent Publication WO 09/099929 discloses certain mesoionic pyrimidinium compounds of Formula i as insecticides wherein, inter alia, X and Y are O, R is substituted phenyl, R2 is CH Q and Q is an optionally substituted 5- or 6-membered heteroaromatic ring, and R3 and R4 are taken together to form an optionally substituted 6-membered ring. SUMMARY OF THE INVENTION This invention is directed to compounds of Formula 1, compositions containing them and their use for controlling invertebrate pests: wherein each R is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio or C1-C4 haloalkylthio; each R2 is independently halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C4 cycloalkyl, C3-C4 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, C1-C4 haloalkylthio, C1-C4 alkylsulfinyl, C1-C4 haloalkylsulfinyl, C C alkylsulfonyl or C1-C4 haloalkylsulfonyl; n is 0, 1 or 2; and m is 1, 2 or 3. This invention provides a composition comprising a compound of Formula 1 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 a compound of Formula 1 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 also provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein). This invention also relates to such method wherein the invertebrate pest or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, said composition optionally further comprising a biologically effective amount of at least one additional biologically active compound or agent. This invention also provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of any of the aforesaid compositions wherein the environment is a plant. This invention also provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest or its environment with a biologically effective amount of any of the aforesaid compositions wherein the environment is a seed. This invention also provides a method for protecting a seed from an invertebrate pest comprising contacting the seed with a biologically effective amount of a compound of Formula 1 (e.g., as a composition described herein). This invention also relates to the treated seed. DETAILS OF THE INVENTION As used herein, the terms "comprises", "comprising", "includes", "including", "has", "having", "contains", "containing", "characterized by" or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated. For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method. The transitional phrase "consisting of excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase "consisting of appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole. The transitional phrase "consisting essentially of is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term "consisting essentially of occupies a middle ground between "comprising" and "consisting of. Where applicants have defined an invention or a portion thereof with an open-ended term such as "comprising", it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms "consisting essentially of or "consisting of. Further, unless expressly stated to the contrary, "or" refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present). Also, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore "a" or "an" should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular. As referred to in this disclosure, the term "invertebrate pest" includes arthropods, gastropods, nematodes and helminths of economic importance as pests.
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