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(12) Patent Application Publication (10) Pub. No.: US 2014/0187776 A1 HOLYOKE, JR

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(12) Patent Application Publication (10) Pub. No.: US 2014/0187776 A1 HOLYOKE, JR US 20140187776A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0187776 A1 HOLYOKE, JR. et al. (43) Pub. Date: Jul. 3, 2014 (54) MIXTURES OF MESOIONIC PESTICIDES (71) Applicant: E I DUPONT DE NEMOURS AND COMPANY, Wilmington, DE (US) (72) Inventors: CALEB WILLIAM HOLYOKE, JR., NEWARK, DE (US); WENMING ZHANG, NEWARK, DE (US); MY-HANH THITONG, BEAR, DE (US): THOMAS FRANCIS PAHUTSKI, JR., ELKTON, MD (US) (73) Assignee: E I DUPONT DE NEMOURS AND wherein COMPANY, Wilmington, DE (US) R" is phenyl optionally substituted with up to 5 substituents independently selected from R, or pyridinyl optionally (21) Appl. No.: 14/184,778 substituted with up to 4 substituents independently selected from R: (22) Filed: Feb. 20, 2014 R’ is C-C haloalkyl; or thiazolyl pyridinyl or pyrimidi Related U.S. Application Data nyl, each optionally substituted with up to 2 substituents independently selected from the group consisting of (63) Continuation of application No. 13/386,160, filed on halogen and C-C alkyl; Jan. 20, 2012, now Pat. No. 8,697,707, filed as appli each R is independently halogen, cyano, C-C alkyl, cation No. PCT/US2010/044285 on Aug. 3, 2010. C-Chaloalkyl, C-C alkoxy, C-Chaloalkoxy, C(R) (60) Provisional application No. 61/231,483, filed on Aug. —NOR or Q; 5, 2009. each R is independently C-C alkyl: Publication Classification Z is CH=CH or S; and (51) Int. Cl. each Q is independently phenyl or pyridinyl, each option AOIN 43/90 (2006.01) ally substituted with up to 3 substituents independently (52) U.S. Cl. Selected from the group consisting of halogen, cyano, CPC ...................................... A0IN 43/90 (2013.01) C-C alkyl, C-C haloalkyl, C-C alkoxy and C-C USPC .......................................................... 544/282 haloalkoxy; and (b) at least one invertebrate pest control agent. (57) ABSTRACT Also disclosed are methods for controlling an invertebrate Disclosed are compositions comprising (a) at least one com pest comprising contacting the invertebrate pest or its envi pound selected from compounds of Formula 1, N-oxides, and ronment with a biologically effective amount of a composi salt thereof, tion of the invention. US 2014/O 187776 A1 Jul. 3, 2014 MIXTURES OF MESOONCPESTICIDES 0001. This application is a continuation of application Ser. O No. 13/386,160, filed Jan. 20, 2012, which is a national stage entry of PCT/US2010/44285, filed Aug. 3, 2010. PCT/ R1 US2010/44285 claims priority benefit from Provisional Application 61/231,483, filed Aug. 5, 2009. (COz-s O FIELD OF THE INVENTION 0002 This invention relates to pesticidal mixtures com ls, prising certain pyrimidinium compounds, their N-oxides, and salts, and at least one other invertebrate pest control agent, Suitable for agronomic, nonagronomic and animal health wherein uses, and methods of their use for controlling invertebrate 0008) R' is phenyl optionally substituted with up to 5 pests such as arthropods in both agronomic and nonagro substituents independently selected from R, or pyridi nyl optionally substituted with up to 4 substituents inde nomic environments, and for treatment of parasite infections pendently selected from R: in animals or infestations in the general environment. I0009 R is C-C haloalkyl; or thiazolyl, pyridinyl or BACKGROUND OF THE INVENTION pyrimidinyl, each optionally substituted with up to 2 Substituents independently selected from the group con 0003. The control of invertebrate pests is extremely sisting of halogen and C-C alkyl: important in achieving high crop efficiency. Damage by 0010 each R is independently halogen, cyano, C-C, invertebrate pests to growing and stored agronomic crops can alkyl, C-Chaloalkyl, C-C alkoxy, C-Chaloalkoxy, cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of invertebrate C(R) NOR or Q; pests in forestry, greenhouse crops, ornamentals, nursery I0011 each R is independently C-C alkyl; crops, stored food and fiber products, livestock, household, 0012 Z is CH=CH or S; and turf, wood products, and public health is also important. 0013 each Q is independently phenyl or pyridinyl, each Many products are commercially available for these pur optionally substituted with up to 3 substituents indepen poses, but the need continues for new compounds that are dently selected from the group consisting of halogen, more effective, less costly, less toxic, environmentally safer cyano, C-C alkyl, C-C haloalkyl, C-C alkoxy and or have different sites of action. C-C haloalkoxy; 0004. The control of animal parasites in animal health is 0014 and essential, especially in the areas of food production and com 0.015 (b) at least one invertebrate pest control agent panion animals. Existing methods of treatment and parasite Selected from the group consisting of abamectin, control are being compromised due to growing resistance to acetamiprid, amitraz, avermectin, azadirachtin, bensul many current commercial parasiticides. The discovery of tap, bifenthrin, buprofezin, cartap, chlorantraniliprole, more effective ways to control animal parasites is therefore chlorfenapyr, chlorpyrifos, clothianidin, cyantranilip imperative. role, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cy 0005 U.S. Pat. No. 5,151,427 discloses mesoionic pyri halothrin, lambda-cyhalothrin, cypermethrin, alpha midinium compounds of Formula i as anthelmintics cypermethrin, Zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, ema mectin, endosulfan, esfenvalerate, ethiprole, fenothio carb, fenoxycarb, fenvalerate, fipronil, flonicamid, R4 flubendiamide, flufenoxuron, hexaflumuron, hydram ethylnon, imidacloprid, indoxacarb, lufenuron, metaflu miZone, methomyl, methoprene, methoxyfenozide, HR nitenpyram, nithiazine, novaluron, oxamyl, phosmet, RN UN N CN pymetrozine, pyrethrin, pyridaben, pyridalyl, lsN H OR3 pyriproxyfen, ryanodine, spinetoram, spinosad, Spirodi H Nt O clofen, spiromesi?en, Spirotetramat, tebufenozide, thia l, cloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate, triflumuron, Bacillus thuringiensis delta-endotoxins, all strains of wherein, interalia, R' and Rare independently C-C alkyl, Bacillus thuringiensis and all strains of nucleo polyhe R is a heteroaromatic 6-membered ring, and R and Rare drosis viruses. independently hydrogen or C-C alkyl. 0016. This invention is also directed to aforesaid compo 0006. The mixtures of the present invention are not dis sition wherein component (a) is selected from at least one closed in this publication. compound of Formula 1 (including all stereoisomers). 0017. This invention is also directed to the compositions SUMMARY OF THE INVENTION described above, and further herein, provided that (a) when 0007. This invention is directed to a composition compris R" is unsubstituted phenylandR is CF, then Zis S.; (b) when ing (a) at least one compound selected from compounds of R" is 2-fluorophenyl and R is 2-chloro-5-thiazolyl, then Z is Formula 1 (including all stereoisomers), N-oxides, and salts S; and (c) when R' is 2-fluorophenyl or 3-(trifluoromethoxy) thereof, phenyl and R is 6-chloro-3-pyridinyl, then Z is CH=CH. US 2014/O 187776 A1 Jul. 3, 2014 0018. This invention also provides a composition com clofen, spiromesi?en, Spirotetramat, tebufenozide, thia prising any of the compositions described above and at least cloprid, thiamethoxam, thiodicarb, thiosultap-sodium, one additional component selected from the group consisting tolfenpyrad, tralomethrin, triazamate, triflumuron, of Surfactants, Solid diluents and liquid diluents. In one Bacillus thuringiensis delta-endotoxins, all strains of embodiment, this invention also provides a composition for Bacillus thuringiensis and all strains of nucleo polyhe controlling an invertebrate pest comprising the composition drosis viruses; and described above and at least one additional component 0028 (c) at least one fungicide: selected from the group consisting of Surfactants, Solid dilu 0029 provided that when the at least one additional ents and liquid diluents, said composition further comprising biologically active compound or agent is selected from at least one additional biologically active compound or agent. group (b) and (i) when R' is unsubstituted phenylandR 0019. This invention is also directed to a composition is CF, then Z is S.; (ii) when R' is 2-fluorophenyland R' comprising (a) at least one compound selected from com is 2-chloro-5-thiazolyl, then Z is S; and (iii) when R' is pounds of Formula 1, N-oxides, and salts thereof, 2-fluorophenyl or 3-(trifluoromethoxy)phenyland R is 6-chloro-3-pyridinyl, then Z is CH=CH. 0030 This invention further provides a composition for protecting an animal from an invertebrate parasitic pest com O prising any of the compositions described above and at least RI one carrier. 0031. This invention provides a method for controlling an invertebrate pest comprising contacting the invertebrate pest N (DCZ N+ NO or its environment with a biologically effective amount of any of the aforesaid compositions. 0032. This invention also provides a method for control s ling an invertebrate pest comprising contacting the inverte brate pest or its environment with a biologically effective wherein amount of any of the aforesaid compositions wherein the (0020) R' is phenyl optionally substituted with up to 5 environment is a plant. substituents independently selected from R, or pyridi 0033. This invention also provides a method for control nyl optionally substituted with up to 4
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