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US 20170208806A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2017/0208806 A1 Barton et al. (43) Pub. Date: Jul. 27, 2017 (54) MOLECULES HAVING PESTICIDAL Publication Classification UTILITY, AND INTERMEDIATES, (51) Int. Cl. COMPOSITIONS, AND PROCESSES, AOIN 4I/O (2006.01) RELATED THERETO AOIN 37/34 (2006.01) AOIN 37/20 (2006.01) (71) Applicant: Dow AgroSciences LLC, Indianapolis, C07C 31 7/28 (2006.01) IN (US) C07C32L/4 (2006.01) (52) U.S. Cl. (72) Inventors: Thomas Barton, Indianapolis, IN (US); CPC ............ A0IN 41/10 (2013.01); C07C317/28 Xin Gao, Carmel, IN (US); Jim (2013.01); C07C321/14 (2013.01); A0IN Hunter, Indianapolis, IN (US); Paul R. 37/20 (2013.01); A0IN 37/34 (2013.01) LePlae, Brownsburg, IN (US); William (57) ABSTRACT C. Lo, Fishers, IN (US); Joshodeep This disclosure relates to the field of molecules having Boruwa, Noida, IN (US); Raghuram pesticidal utility against pests in Phyla Arthropoda, Mol Tangirala, Bengaluru, IN (US); Gerald lusca, and Nematoda, processes to produce Such molecules, B. Watson, Zionsville, IN (US); John intermediates used in Such processes, compositions contain Herbert, Fishers, IN (US) ing Such molecules, and processes of using Such molecules and compositions against Such pests. These molecules and compositions may be used, for example, as acaricides, (73) Assignee: Dow AgroSciences LLC, Indianapolis, insecticides, miticides, molluscicides, and nematicides. This IN (US) document discloses molecules having the following formula (“Formula One”). (21) Appl. No.: 15/408,693 (22) Filed: Jan. 18, 2017 Related U.S. Application Data (60) Provisional application No. 62/286.684, filed on Jan. 25, 2016, provisional application No. 62/286,690, filed on Jan. 25, 2016. US 2017/020880.6 A1 Jul. 27, 2017 MOLECULES HAVING PESTCDAL diseases. While only a few dozen species of gastropods are UTILITY. AND INTERMEDIATES, serious regional pests, a handful of species are important COMPOSITIONS, AND PROCESSES, pests on a worldwide scale. In particular, gastropods affect RELATED THERETO a wide variety of agricultural and horticultural crops, such as, arable, pastoral, and fiber crops; vegetables; bush and CROSS REFERENCE TO RELATED tree fruits; herbs; and ornamentals (Speiser). APPLICATIONS 0007 Termites cause damage to all types of private and 0001. This application claims the benefit of, and priority public structures, as well as, to agricultural and forestry from, U.S. Provisional Patent Application Ser. Nos. 62/286, resources. In 2005, it was estimated that termites cause over 684 and 62/286,690 both filed Jan. 25, 2016, each of which USS50 billion in damage worldwide each year (Korb). are expressly incorporated by reference herein. 0008 Consequently, for many reasons, including those mentioned above, there is an on-going need for the costly FIELD OF THIS DISCLOSURE (estimated to be about USS256 million per pesticide in 0002. This disclosure relates to the field of molecules 2010), time-consuming (on average about 10 years per having pesticidal utility against pests in Phyla Arthropoda, pesticide), and difficult, development of new pesticides Mollusca, and Nematoda, processes to produce Such mol (CropLife America). ecules, intermediates used in Such processes, pesticidal 0009. DeMassey et al. discloses the following structure. compositions containing Such molecules, and processes of For more detail, refer to U.S. 2002/0068838. using such pesticidal compositions against Such pests. These pesticidal compositions may be used, for example, as aca ricides, insecticides, miticides, molluscicides, and nemati cides. b X Z X S2Y N /R BACKGROUND OF THIS DISCLOSURE -C-N 0003 “Many of the most dangerous human diseases are C e 21 R2 transmitted by insect vectors” (Rivero et al.). “Historically, malaria, dengue, yellow fever, plague, filariasis, louse-borne d typhus, trypanosomiasis, leishmaniasis, and other vector borne diseases were responsible for more human disease and death in the 17" through the early 20" centuries than all CERTAIN REFERENCES CITED IN THIS other causes combined' (Gubler). Vector-borne diseases are DISCLOSURE responsible for about 17% of the global parasitic and infec tious diseases. Malaria alone causes over 800,000 deaths a 0010 CropLife America, The Cost of New Agrochemical year, 85% of which occur in children under five years of age. Product Discovery, Development & Registration, and Each year there are about 50 to about 100 million cases of Research & Development predictions for the Future, dengue fever. A further 250,000 to 500,000 cases of dengue 2010. hemorrhagic fever occur each year (Matthews). Vector con 0011 Gubler, D., Resurgent Vector-Borne Diseases as a trol plays a critical role in the prevention and control of Global Health Problem, Emerging Infectious Diseases, infectious diseases. However, insecticide resistance, includ Vol. 4, No. 3, p. 442-450, 1998. ing resistance to multiple insecticides, has arisen in all insect (0012 Korb, J., Termites, Current Biology, Vol. 17, No. species that are major vectors of human diseases (Rivero et al.). Recently, more than 550 arthropod pest species have 23, 2007. developed resistance to at least one pesticide (Whalon et al.). 0013 Matthews, G., Integrated Vector Management: 0004 Each year insects, plant pathogens, and weeds, Controlling Vectors of Malaria and Other Insect Vector destroy more than 40% of all food production. This loss Borne Diseases, Ch. 1, p. 1-2011. occurs despite the application of pesticides and the use of a 0014 Nicol, J., Turner S.; Coyne, L.; den Nijs, L., wide array of non-chemical controls. Such as, crop rotations, Hocksland, L., Tahna-Maafi, Z., Current Nematode and biological controls. If just some of this food could be Threats to World Agriculture, Genomic and Molecular saved, it could be used to feed the more than three billion Genetics of Plant Nematode Interactions, p. 21-43, people in the world who are malnourished (Pimental). 2011). 0005 Plant parasitic nematodes are among the most (0015 Pimental, D., Pest Control in World Agriculture, widespread pests, and are frequently one of the most insidi Agricultural Sciences Vol. II, 2009. ous and costly. It has been estimated that losses attributable to nematodes are from about 9% in developed countries to 0016 Rivero, A., Vezilier, 3., Weill, M., Read, A., Gan about 15% in undeveloped countries. However, in the don, S., Insect Control of Vector-Borne Diseases: When is United States of America a survey of 35 States on various Insect Resistance a Problem? Public Library of Science crops indicated nematode-derived losses of up to 25% Pathogens, Vol. 6, No. 8, p. 1-9, 2010. (Nicol et al.). 0017 Speiser, B., Molluscicides, Encyclopedia of Pest 0006. It is noted that gastropods (slugs and snails) are Management, Ch. 219, p. 506-508, 2002. pests of less economic importance than other arthropods or 0018 Whalon, M., Mota-Sanchez, D., Hollingworth, R., nematodes, but in certain places they may reduce yields Analysis of Global Pesticide Resistance in Arthropods, substantially, severely affecting the quality of harvested Global Pesticide Resistance in Arthropods, Ch. 1, p. 5-33, products, as well as, transmitting human, animal, and plant 2008. US 2017/020880.6 A1 Jul. 27, 2017 DEFINITIONS USED IN THIS DISCLOSURE benoxacor, benoxafos, benquinox, benSulfuron, bensulide, 0019. The examples given in these definitions are gener bensultap, bentaluron, bentazon, bentaZone, benthiavalicarb, ally non-exhaustive and must not be construed as limiting benthiazole, benthiocarb, bentranil, benzadox, benzalko the disclosure. It is understood that a substituent should nium chloride, benzamacril, benzamizole, benzamorf, ben comply with chemical bonding rules and steric compatibility Zene hexachloride, benzfendizone, benzimine, benzipram, constraints in relation to the particular molecule to which it benzobicyclon, benzoepin, benzofenap, benzofluor, benzo is attached. These definitions are only to be used for the hydroxamic acid, benzomate, benzophosphate, benzothiadi purposes of this disclosure. azole, benzovindiflupyr, benzoximate, benzoylprop, benz 0020 “Active ingredient’ means a material having activ thiazuron, benzuocaotong, benzyl benzoate, benzyladenine, ity useful in controlling pests, and/or that is useful in helping berberine, beta-cyfluthrin, beta-cypermethrin, bethoxazin, other materials have better activity in controlling pests, BHC, bialaphos, bicyclopyrone, bifenazate, bifenox, bifen examples of Such materials include, but are not limited to, thrin, bifujunzhi, bilanafos, binapacryl, bingqingxiao, bio acaricides, algicides, avicides, bactericides, fungicides, her allethrin, bioethanomethrin, biopermethrin, bioresmethrin, bicides, insecticides, molluscicides, nematicides, rodenti biphenyl, bisazir, bismerthiazol, bismerthiazol-copper, bis cides, virucides, antifeedants, bird repellents, chemosteri phenylmercury methylenediCX-naphthalene-y-Sulphonate), lants, herbicide Safeners, insect attractants, insect repellents, bispyribac, bistrifluron, bisultap, bitertanol, bithionol, bix mammal repellents, mating disrupters, plantactivators, plant afen, blasticidin-S, borax, Bordeaux mixture, boric acid, growth regulators, and synergists. Specific examples of Such boscalid, BPPS, brassinolide, brassinolide-ethyl, brevi materials include, but are not limited to, the materials listed comin, brodifacoum, brofenprox, brofenvalerate, brofla in active ingredient group alpha. nilide, brofluthrinate, bromacil, bromadiolone, bromchlo 0021 “Active ingredient group
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  • NEXGARD SPECTRA, INN-Afoxolaner-Milbemycin Oxime

    NEXGARD SPECTRA, INN-Afoxolaner-Milbemycin Oxime

    EMA/704200/2014 EMEA/V/C/003842 Nexgard Spectra (afoxolaner/milbemycin oxime) An overview of Nexgard Spectra and why it is authorised in the EU What is Nexgard Spectra and what is it used for? Nexgard Spectra is a veterinary medicine used to treat infestations with fleas, ticks, as well as demodectic and sarcoptic mange (skin infestations caused by two different types of mites) in dogs when prevention of heartworm disease (caused by a worm that infects the heart and blood vessels and is transmitted by mosquitoes), lungworm disease, eye worm and/or treatment of gut worms (hookworms, roundworms and whipworm) is also required. Nexgard Spectra contains the active substances afoxolaner and milbemycin oxime. How is Nexgard Spectra used? Nexgard Spectra is available as chewable tablets in five different strengths for use in dogs of different weights. It can only be obtained with a prescription. The appropriate strength of tablets should be used according to the dog’s weight. Treatment for fleas and ticks should be repeated at monthly intervals during the flea or tick seasons; Nexgard Spectra can be used as part of the seasonal treatment of fleas and ticks in dogs infected with gut worms. A single dose of Nexgard Spectra is given to treat gut worms. After which, further flea and tick treatment should be continued with a monovalent product containing a single active substance. For demodectic mange, treatment should be repeated monthly until the mange is successfully treated (as confirmed by two negative skin scrapings one month apart) whereas for sarcoptic mange treatment is given monthly for two months, or longer based on clinical signs and skin scrapings.