WO 2016/033025 Al 3 March 2016 (03.03.2016) P O P C T
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(12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2016/033025 Al 3 March 2016 (03.03.2016) P O P C T (51) International Patent Classification: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, A 43/653 (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, ΓΝ , IR, IS, JP, KE, KG, KN, KP, KR, (21) International Application Number: KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, PCT/US20 15/046667 MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (22) International Filing Date: PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, 25 August 2015 (25.08.2015) SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every (26) Publication Language: English kind of regional protection available): ARIPO (BW, GH, (30) Priority Data: GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, 62/041,685 26 August 2014 (26.08.2014) US TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, (71) Applicant: DOW AGROSCIENCES LLC [US/US]; DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, 9330 Zionsville Road, Indianapolis, ΓΝ 46268 (US). 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: BAUM, Erich W.; 9330 Zionsville Road, Indi GW, KM, ML, MR, NE, SN, TD, TG). anapolis, ΓΝ 46268 (US). FISCHER, Lindsey G.; 9330 Zionsville Road, Indianapolis, IN 46268 (US). CROUSE, Declarations under Rule 4.17: Gary D.; 9330 Zionsville Road, Indianapolis, IN 46268 — as to applicant's entitlement to apply for and be granted a (US). SPARKS, Thomas C ; 9330 Zionsville Road, Indi patent (Rule 4.1 7(H)) anapolis, IN 46268 (US). — as to the applicant's entitlement to claim the priority of the (74) Agent: CORVIN, Carl; The Dow Chemical Company- earlier application (Rule 4.1 7(in)) DO NOT USE, 9330 Zionsville Rd, Indianapolis, Indiana 46268 (US). Published: (81) Designated States (unless otherwise indicated, for every — with international search report (Art. 21(3)) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (54) Title: MOLECULES HAVING CERTAIN PESTICIDAL UTILITIES, AND INTERMEDIATES, COMPOSITIONS, AND PROCESSES RELATED THERETO o © v o (57) Abstract: This disclosure relates to the field of molecules having pesticidal utility against pests in Phyla Nematoda, Arthro - poda, and/or Mollusca, processes to produce such molecules and intermediates used in such processes, compositions containing such molecules, and processes of using such molecules against such pests. These molecules may be used, for example, as nematicides, o acaricides, insecticides, miticides, and/or moUuscicides. This document discloses molecules having the following formula ("Formula One"). MOLECU LES HAVING CERTAIN PESTICIDAL UTILITIES, AND INTERM EDIATES, COM POSITIONS, AND PROCESSES RELATED THERETO CROSS REFERENCE TO RELATED APPLICATIONS This application claims the benefit of, and priority from, U.S . Provisional Patent Application Serial No. 62/041,685 filed 26 Aug 2014, the entire disclosure of which is hereby expressly incorporated by reference . FIELD OF THE DISCLOSU RE The invention disclosed in this document is related to the field of processes to produce molecules that are useful as pesticides (e.g. , acaricides, insecticides, molluscicides, and nematicides), such molecules, and processes of using such molecules to control pests. BACKGROUND OF THE DISCLOSU RE Pests cause millions of human deaths around the world each year. Furthermore, there are more than ten thousand species of pests that cause losses in agriculture. The world-wide agricultural losses amount to billions of U.S. dollars each year. Termites cause damage to all kinds of private and public structures. The world- wide termite damage losses amount to billions of U.S . dolla rs each year. Stored food pests eat and adulterate stored food . The world-wide stored food losses amount to billions of U.S . dollars each year, but more importantly, deprive people of needed food . There is an acute need for new pesticides. Certain pests are developing resistance to pesticides in current use. Hundreds of pest species are resistant to one or more pesticides. The development of resistance to some of the older pesticides, such as DDT, the carbamates, and the organophosphates, is well known . But resistance has even developed to some of the newer pesticides, for example, imidacloprid . Therefore, for many reasons, including the above reasons, a need exists for new pesticides. DEFINITIONS The examples given in the definitions are generally non-exhaustive and must not be construed as limiting the invention disclosed in this document. It is understood that a substituent should comply with chemical bonding rules and steric compatibility constraints in relation to the particular molecule to which it is attached . "Alkenyl" means an acyclic, unsaturated (at least one carbon-carbon double bond), branched or unbranched, substituent consisting of carbon and hydrogen, for example, vinyl, allyl, butenyl, pentenyl, and hexenyl. "Alkenyloxy" means an alkenyl further consisting of a carbon-oxygen single bond, for example, allyloxy, butenyloxy, pentenyloxy, hexenyloxy. "Alkoxy" means an alkyl further consisting of a carbon-oxygen single bond, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, and e -butoxy. "Alkyl" means an acyclic, saturated, branched or unbranched, substituent consisting of carbon and hydrogen, for example, methyl, ethyl, (C3)alkyl which represents n-propyl and isopropyl, (C4)alkyl which represents n-butyl, sec-butyl, isobutyl, and er -butyl. "Alkynyl" means an acyclic, unsaturated (at least one carbon-carbon triple bond), branched or unbranched, substituent consisting of carbon and hydrogen, for example, ethynyl, propargyl, butynyl, and pentynyl . "Alkynyloxy" means an alkynyl further consisting of a carbon-oxygen single bond, for example, pentynyloxy, hexynyloxy, heptynyloxy, and octynyloxy. "Aryl" means a cyclic, aromatic substituent consisting of hydrogen and carbon, for example, phenyl, naphthyl, and biphenyl . "Cycloalkyl" means a monocyclic or polycyclic, saturated substituent consisting of carbon and hydrogen, for example, cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, bicyclo[2 .2 .2]octyl, and decahydronaphthyl . "Cycloalkoxy" means a cycloalkyl further consisting of a carbon-oxygen single bond, for example, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, norbornyloxy, and bicyclo[2 .2 .2]octyloxy. "Halo" means fluoro, chloro, bromo, and iodo. "Haloalkoxy" means an alkoxy further consisting of, from one to the maximum possible number of identical or different, halos, for example, fluoromethoxy, trifluoromethoxy, 2,2-difluoropropoxy, chloromethoxy, trichloromethoxy, 1, 1,2,2- tetrafluoroethoxy, and pentafluoroethoxy. "Haloalkyl" means an alkyl further consisting of, from one to the maximum possible number of, identical or different, halos, for example, fluoromethyl, trifluoromethyl, 2,2-difluoropropyl, chloromethyl, trichloromethyl, and 1, 1,2,2- tetrafluoroethyl . "Heterocyclyl" means a cyclic substituent that may be fully saturated, partially unsaturated, or fully unsaturated, where the cyclic structure contains at least one carbon and at least one heteroatom, where said heteroatom is nitrogen, sulfur, or oxygen. In the case of sulfur, that atom can be in other oxidation states such as a sulfoxide and sulfone . Examples of aromatic heterocyclyls include, but are not limited to, benzofuranyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, benzothienyl, benzothiazolyl, cinnolinyl, furanyl, imidazolyl, indazolyl, indolyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl, triazinyl, and triazolyl . Examples of fully saturated heterocyclyls include, but are not limited to, piperazinyl, piperidinyl, morpholinyl, pyrrolidinyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl and tetrahydropyranyl . Examples of partially unsaturated heterocyclyls include, but are not limited to, 1,2,3,4- tetrahydroquinolinyl, 4,5-dihydro-oxazolyl, 4,5-dihydro-l/-/-pyrazolyl, 4,5-dihydro- isoxazolyl, and 2,3-dihydro- [l,3,4] -oxadiazolyl . DETAILED DESCRIPTION OF THE DISCLOSU RE This document discloses molecules having the following formula ("Formul One ") wherein : (A) R , R2, R3, R4, R5, R6, R7, and R9 are each independently selected from the group consisting of H, F, CI, Br, I, CN, N0 2, OH, ( -C4)alkyl, (C2-C4)alkenyl, (C2- C4)alkynyl, (Ci-C4)haloa lkyl, (Ci-C4)alkoxy, (Ci-C4)haloa lkoxy, (C3-C6)cycloalkyl, and (C3-C6)cycloalkoxy, wherein each alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, cycloalkyl, and cycloa lkoxy is optionally substituted with one or more substituents independently selected from the group consisting of F, CI, CN, OH, and oxo; (B) R8 is H; (C) L is a (Ci-C4)alkyl that is optionally substituted with one or more substituents independently selected from the group consisting of F, CI, CN, OH, and oxo; 0 (D) R is selected from the group consisting of H, (d-C 4)alkyl, (C2-C4)alkenyl, (C2-C4)alkynyl,