Molecules with pesticide activity and related intermediates, compositions and processes

Abstract

To provide molecules having pesticidal utility against pests in Phyla Arthropoda, Mollusca and Nematoda, processes to produce such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes of using such pesticidal compositions against such pests.SOLUTION: This invention provides molecules having the formula 1 in the figure. (R1, R2, R3, R4 and R5 are each independently H, halogen, or the like; R6 and R9 are each independently H or C1-C6 alkyl; and Q1 and Q2 are each independently O or S).SELECTED DRAWING: None

Description

[Technical Field]

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS This application is a continuation of U.S. Provisional Patent Applications Nos. 62 / 148830, 62 / 148837, 62 / 148809, 62 / 148814, 62 / 148818, and 62 / 148824, all filed April 17, 2015. The entire contents of all of the above-identified applications are hereby incorporated by reference into this application.

[0002] The present disclosure relates to the field of molecules having pesticidal activity against pests of the phyla Arthropoda, Mollusca, and Nematoda, processes for producing such molecules, intermediates used in such processes, pesticidal compositions containing such molecules, and processes for using such pesticidal compositions against such pests. These pesticidal compositions can be used, for example, as acaricides, insecticides, miticides, molluscicides, and nematicides. [Background technology]

[0003] "Many of the most dangerous human diseases are transmitted by insect vectors" (Rivero et al.). "Historically, malaria, dengue fever, yellow fever, plague, filariasis, louse-borne typhus, trypanomiasis, leishmaniasis, and other vector-borne diseases were transmitted between the 17th and 20th centuries. "Throughout the early 20th century, they caused more human disease and death than all other causes combined" (Gubler). Vector-borne diseases account for approximately 17% of the world's parasitic and infectious diseases. Malaria alone causes over 800,000 deaths per year, 85% of which occur in children under the age of five. Approximately 50 million to 100 million cases of dengue fever occur annually. Additionally, 250,000 to 500,000 cases of dengue hemorrhagic fever occur annually (Matthews). Vector control plays a crucial role in the prevention and control of infectious diseases. However, insecticide resistance, including resistance to multiple insecticides, has emerged in all insect species that are major vectors of human disease (Rivero et al.). Recently, over 550 arthropod species have become resistant to at least one pesticide (Whalon et al.). Furthermore, instances of insect resistance continue to far outnumber instances of herbicide and fungicide resistance (Sparks et al.).

[0004] Each year, insects, plant pathogens and weeds destroy over 40% of all food production. This loss occurs despite the use of various non-chemical controls, such as crop rotation and biological controls, and if even a portion of this food could be saved, it could be used to feed the more than 3 billion undernourished people in the world (Pimental).

[0005] Plant-parasitic nematodes are among the most widespread and often most insidious pests. Nematode-related losses account for approximately 9% (in developed countries) of the world's food security. It has been estimated that the loss of crops due to nematodes is about 15% (in less developed countries). However, in the United States, a study of 35 states on various crops revealed that the loss due to nematodes can be as high as 25% (Nicol et al.). .

[0006] Gastropods (slugs and snails) are pests of less economic importance than other arthropods or nematodes, but in certain locations they can substantially reduce crop yields, significantly affect crop quality, and transmit human, animal, and plant diseases. Dozens of gastropod species are serious regional pests, and several are major pests on a global scale. In particular, gastropods affect a wide range of agricultural and horticultural crops, including arable, pasture, and fiber crops; vegetables; fruit trees; herbs; and ornamentals (Speiser).

[0007] Termites cause damage to all types of private and public structures, as well as agricultural and forestry resources. In 2005, it was estimated that termites caused US$50 billion in damage annually worldwide. It was estimated that Korb.

[0008] Therefore, for many reasons, including those mentioned above, it is costly (in 2010, There is a continuing need to develop new pesticides, which is time-consuming (an average of about 10 years per pesticide), difficult (estimated at about US$256 million per pesticide) and time-consuming (CropLife America).

[0009] CERTAIN REFERENCES CITED IN THIS DISCLOSURE CropLife America, The Cost of New Agrochemical Product Discovery, Development & Registration, and Research & Development predictions for the Future, 2010. Drewes, M., Tietjen, K., Sparks, TC, High-Throughput Screening in Agrochemical Research, Modern Methods in Crop Protection Research, Part I, Methods for the Design and Optimization of New Active Ingredients, Jeschke, P., Kramer, W., Schirmer, U., and Matthias W. eds., p. 1-20, 2012。 Gubler, D., Resurgent Vector-Borne Diseases as a Global Health Problem, Emerging Infectious Diseases, Vol. 4, No. 3, p. 442-450, 1998。 Korb, J., Termites, Current Biology, Vol. 17, No. 23, 2007。 Matthews, G., Integrated Vector Management: Controlling Vectors of Malaria and Other Insect Vector Borne Diseases, Ch. 1, p. 1, 2011。 Nicol, J., Turner S., Coyne, L., den Nijs, L., Hocksland, L., Tahna-Maafi, Z., Current Nematode Threats to World Agriculture, Genomic and Molecular Genetics of Plant - Nematode Interactions, p. 21-43, 2011。 Pimental, D., Pest Control in World Agriculture, Agricultural Sciences - Vol. II, 2009。 Rivero, A., Vezilier, J., Weill, M., Read, A., Gandon, S., Insect Control of Vector-Borne Diseases: When is Insect Resistance a Problem? Public Library of Science Pathogens, Vol. 6, No. 8, p. 1-9, 2010. Sparks TC, Nauen R., IRAC: Mode of action classification and insecticide resistance management, Pesticide Biochemistry and Physiology (2014) December 4, 2014 Available online. Speiser, B., Molluscicides, Encyclopedia of Pest Management, Ch. 219, p. 506-508, 2002. Whalon, M., Mota-Sanchez, D., Hollingworth, R., Analysis of Global Pesticide Resistance in Arthropods, Global Pesticide Resistance in Arthropods, Ch. 1, p. 5-33, 2008.

[0010] Definitions used in this disclosure The examples provided in this definition are generally non-exhaustive and should not be construed as limiting the present disclosure. It is understood that a substituent must conform to the chemical bonding rules and steric compatibility constraints of the particular molecule to which it is attached. These definitions are used solely for the purposes of this disclosure.

[0011] The term "active ingredient" refers to a substance having an activity useful for controlling pests and / or a substance useful as a supplement to other substances having superior activity for controlling pests, examples of such substances include, but are not limited to, acaricides, algicides, antifeedants, bird killers, bactericides, bird repellents, chemosterilants, fungicides, herbicide safeners, herbicides, insect attractants, insect repellents, insecticides, mammalian repellents, mating disruptants, molluscicides, nematicides, plant activators, plant growth regulators, rodenticides, synergists, and antivirals (see alanwood.net). Specific examples of such substances include, but are not limited to, those listed in Active Ingredient Group Alpha. .

[0012] The term "Alpha Active Ingredients Group" (hereinafter "AIGA") collectively refers to the following substances: (1) (3-ethoxypropyl)mercury bromide, 1,2-dibromoethane, 1,2-dichloroethane Benzene, 1,2-dichloropropane, 1,3-dichloropropene, 1-MCP, 1-methylcyclopropene, 1-naphthol, 2-(octylthio)ethanol, 2,3,3-TPA, 2,3,5-triiodobenzoic acid, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4,5-TP, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 2,4-DES, 2,4-DP, 2,4-MCPA, 2,4-MCPB, 2iP, 2-methoxyethylmercury chloride, 2-phenylphenone alcohol, 3,4-DA, 3,4-DB, 3,4-DP, 3,6-dichloropicolinic acid, 4-aminopyridine, 4-CPA, 4-CPB, 4-CPP, 4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate , 8-phenylmercuryoxyquinoline, abamectin, abamectin-aminomethyl, abscisic acid, ACC, acephate, acequinocyl, acetamiprid, acetion (acethion), acetochlor, acetophenate, acetophenone Acetophos, acetoprole, acibenzolar, acifluorfen, aclonifen, ACN, acrep, ac Linatrin, acrolein, acrylonitrile, acypetacs, afidopyropen, afoxolaner, alachlor, alanap, alanycarb, albendazo aldicarb, aldicarb sulfone, aldimorph, aldoxy Carb, Aldrin, Allethrin, Allicin, Allidochlor, Allosamiji , alloxydim, allyl alcohol, alixycarb, arorac, alpha-cypermethrin, alpha-endosulfan, alphamethrin, altretamine, aluminum phosphide, aluminum phosphide, ametoctrazine, ametridione, ametryn, ametryne, amivudine, amicarbazone, a Micarthiazol, amidithione, amidoflumet, amidosulfuron, aminocarb, aminocyclopyrachlor, aminopyralid, amino Triazole, amiprofos-methyl, amiprophos ), amiprophos-methyl, amisulbrom, amiton, amitraz, amitrole, ammonium sulfamate , Ambam, amorphous silica gel, amorphous silicon dioxide, ampropylfos, AMS, anabasine, ancymidol, anilazine, anilo Anilofos, anisuron, anthraquinone, antu, apholate, alamite, alprocarb, arsenous acid, asomate (asomate), aspirin, ashram, athidathion, atraton, atrazine, aureofungin, avermectin B1, AVG, Aviglycine, azaconazole, azadirachtin, azafenidin, azamethiphos, azidithiophene azidithion, azimsulfuron, azinphos ethyl, azinphos-ethyl, azinphos methyl, azinphos-methyl, adiprothrin, adiprothrin, azithiram, azobenzene, azocyclotin, azothoate, azoxystrobin, bachmedesh, barban, barbanate, barium hexafluorosilicate, Barium polysulfide, barium silicofluoride, Bartholin, basic copper carbonate, basic copper chloride, basic copper sulfate, BCPC, beflubutamide, benalaxyl, benalaxyl-M, benazolin, bencarbazone, benclothiaz, bendaqingbingzhi, bendiocarb, bendioxide, benefin, benfluralin, benfuracarb, benfuresate, benmihuang caoan), benodanil, benomyl, benoxacor, benoxafos, benquinox, bensulfuron, bensulide, bensultap, bentaluron, bentazon, bentazon, bentazon, benthiavalicarb, benthiazole, bentiocarb, benquinox Bentranil, benzadox, benzalkonium chloride, benzamacril, benzamizole, benzamorph, benzene hexachloride, benzfendizone, benzimine, benzipram, benzobicyclon, benzoepin, benzofenap, benzofluo benzofluor, benzohydroxamic acid, benzomate, benzophos benzophosphate, benzothiadiazole, benzovindiflupyr, benzoximate, benzoylprop, benzthiazuron, benzocaotong, benzyl benzoate, benzyladenine, berberine, beta-cyfluthrin, beta-cypermethrin, bethoxazin, BHC, bialaphos, bicyclopyrone, bifenazate, bifenox, bifen Entrin, bifujunzhi, bilanafos, binapacryl, Bingqingxiao, bioallethrin, bioethanomethrin, biopermethrin, bioresmetry phenanthrene, biphenyl, bisazir, bismerthiazol, bismerthiazol-copper, bisphenylmercury methylenedi(x-naphthalene-y-sulphonate), bispyribac, bistrifluron, bisultap, bitertanol, bithionol, bixafen, blasticidin-S, borax Lux, Bordeaux mixture, boric acid, boscalid, BPPS, brassinolide, brassinolide-ethyl, brevicomin, brodifacoum, brofenprox, brofenvalerate, broflanilide, brofluthrinate ...prox, brofenvalerate, brofenprox, brofenprox, brofenvalerate, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox, brofenprox Romacil, bromadiolone, bromchlophos, bromethalin, bromethrin, bromfenvinphos, bromoacetamide, bromobonil, bromobutide, bromociclen, bromocyclen, bromo-DDT, bromofenoxim, bromophos, bromomethane, bromophos, bromophos-ethyl, bromopropylate, bromothalonil, bromophenoxyethanol ... Lomoxynil, brompyrazone, bromuconazole, bronopol, BRP, BTH, bucarpolate, bufencarb, buminafos, bupirimate, buprofezin, bulga Ndi mixture, busulfan, busulphan, butacarb, butachlor, butafenacil, butam, butamifos, butane-fipronil, butathiofos , butenachlor, butene-fipronil, butethrin, buthidazole, buthibate, buthiuron, butifos, butocarboxim, butonate , butopyronoxyl, butoxycarboxim, Butralin, butrizol, butroxydim, buturon, butylamine, butyrate, butylchlorophos, butylene-fipronil, cacodylic acid, cadusafos, cafenstrole, calcife roll, calcium arsenate, calcium chlorate, calcium cyanamide, calcium cyanide, calcium polysulfide, calvinphos , cambendichlor, camphechlor, camphor, captafol, captan, carbam, carbamorph ), carbanolate, carbaryl, carbaryl ), carbasulam, carbathion, carbendazim, carbendazol, carbetamide, carbofenotion, carbofuran, carbon disulfide, carbon tetrachloride, carbonyl sulfide, carbophen Notion, carbophos, carbosulfan, carboxazole, carboxide, carboxin, carfentrazone, carpropami Do, cartap, carvacrol, carvone, CAVP, CDAA, CDEA, CDEC, Cellocidin, CEPC, ceralure, cerenox, Cevadilla, Cheshunt mixture, chinalphos, quinalphos-methyl, chinomethionat, chinomethionate, chiralaxyl, chitosan, chlobenthiazone, chlomethoxyfen, chloralose, chloramben, chloramine phosphorus, chlor Rhamphenicol (chloramphenicol), chloraniformethan (chloraniformethan), chloranil, chloranocryl (chloranocryl), chlorantraniliprole (chlorantraniliprole), chlorazifop (chlorazifop), chlorazine (chlorazine), chlorbeneside, chlorbenzuron (chlorbenzuron), chlorbicyclen (chlorbicyclen), chlorbromuron (chlorbromuron), chlorbufam (chlorbufam), chlordane (chlordane), chlordecone (chlordecone), chlordimeform (chlordimeform), chlorenpentrin (chlorempenthrin), chloretazate (chloretazate), chlorethephon (chlorethephon), chlorethoxyfos (chlorethoxyfos), chloreturon (chloreturon), Chlorfenac, chlorfenapyr, chlorfenazole, chlorfenethol, chlorfenidim, chlorfenprop, chlorfenson, chlorphen Sulfide (chlorfensulphide), chlorfenvinphos, chlor Fenvinphos-methyl, chlorfluazuron, chlorflurazole (chlorflurazole), chlorflurecol, chlorfluren, chlorflurenol, chloridazon, chlorimuron, chlorinate, chlor-IPC, chlormephos, Lormequat, chlormesulone, chlormethoxynil, chlornidine, chlornitrofen, chloroacetic acid, chlorobenzilate, chlorodinitronaphthalenes, chlorophenizon, chloroform, chloromebuform, chloromethicone, Thiuron, chloroneb, chlorophacinone, chlorophos, chloropicrin, chloropon, chloropropylate, chlorothalonil, chlorotoluron, chloroxy Phenizim, chloroxifenidim, chloroxuron, chloroxynil, chlorphonium, chlorphoxim, chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos, chlorpyrifos-methyl, chlorquinox, chlorsulfuron, chlorthal, chlorthiamid, chlorthiophos, chlortoluron, chlorzoli chlorzolinate, chltosan, cholecalciferol, choline chloride, chromafenozide, cycloheximide, Mectacarb, cimetacarb, cinerine I, cinerine II, cinerines, cinidon-ethyl, cinmethylin, cinosulfuron, cintofen, ciobutide, cisanilide, cismethrin, clacyfos, clefoxydim, clenpirin, clenpyrin, clethodim, climbazole, cliogene cliodinate, clodinafop, cloethocarb, Clofencet, clofenotan, clofentezine, clofenvinphos, clofibric acid, clofop, clomazone, clomeprop, clonitralid, cloprop, cloproxydim, clopyralid, cloquintocet, cloransulam, closantel, clothianidin, clotrimazole, cloxidil cloxyfonac, cloxylacon, clozylacon, CMA, CMMP, CMP, CMU, codlelure, cholecalciferol, colophonate, copper 8-quinolinolate ), copper acetate, copper arsenite acetate, copper arsenate, copper carbonate (basic), copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper silicate, copper sulfate, copper sulfate (basic), copper zinc chromate, coumachlor, coumafene, coumafos, coumafuryl (coumafuryl), coumaphos, coumatetralyl, coumethoxystrobin, coumithoate, coumoxystrobin, CPMC, CPMF, CPPC, credazine, cresol, cresylic acid, crimidine, crotamiton, crotoxyfos ), crotoxyphos, crufomate, cryolite, cue-lure, cufraneb, cumyleron, cumyluron, cuprobam, cuprous oxide, curcumenol, CVMP, cyanamide, cyanatrin, cyanazine, cyanofenphos, cyan, cyanophos, cyanthoate, cyan Cyanuric acid, cyazofamid, sibutryne, cyclafuramid, cyclanilide, cyclaniliprole, cyclethrin, cycloate, cycloheximide, cycloprate, cycloprothrin, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, Enopyrafen, cyflufenamid, cyflumetofen, cyfluthrin, cyhalofop, cyha Cyhalothrin, cyhexatin, cymiazole, Cymoxanil, cyometrinil, cypendazole, cypermethrin, cyperquat, cyphenothrin, cyprazine, cyprazole, cyproconazole, cyprodinil, cyprofuram ), cypromid, cyprosulfamide, cyromazine, cythioate, cytrex, dymron, dara Pon, daminozide, dayoutong, dazomet, DBCP, d-camphor, DCB, DCIP, DCPA, DCPTA, DCU, DDD, DDPP, DDT, DDVP, de Bacarb, decafentin, decamethrin , decarbofuran, DEET, dehydroacetic acid, diquat , delachlor, delnav, deltamethrin , demephion, demephion-O, demephion-S, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methylsulphone, demeton-S-methylsulphon, DEP, depallethrine, derris, desmedipham, desmetryn, desmetryne, d-fanshiluquebingjuzhi, diafenthiuron , dialifol, dialifos, diallate, diamidafos, dianat, diatomaceous earth, diatomite, diazinon on), dibrom, dibutyl phthalate, dibutyl succinate, dicamba ), dicapton (dicapthon), dichlobenil (dichlobenil), diclofenthion (dichlofenthion), dichlofluanid (dichlofluanid), diclone (dichlone), diclo Dichloralurea, dichlorbenzuron, dichlorfenidim, dichlorflurecol, dichlorflu Dichlorflurenol, dichlormate, dichlormid, dichloromethane, dichloromezotiaz, dichlorophen, dichlorprop, dichlorprop-P, dichlorvos, dichlozolin, dichlozoline, diclobutrazol, diclocymet, diclofop, diclomezine, dicloran, diclosulam, dicofol (dicofol), dicophane, dicoumarol, dicresyl, dicrotophos, dicryl, dicoumarol, dicycla Dicyclanil, dicyclonon, dieldrin, dienochlor, diethamquat, diethathyl, diethion, diethion, diethofencarb ), dietholate, diethon, diethyl pyrocarbonate, diethyl Toluamide, difenacoum, difenoconazole, difenopenten, difenoxuron, difenzocor difenzoquat, difethialone, diflovidazin ), diflubenzuron, diflufenican, diflu Diflufenicanil, diflufenzopyr, diflumet Diflumetorim, dikegulac, dilor, dimatif, dimefluthrin, dimefox, dimefuron, dimehypo, dimepiperate, dimethachlone, dimethane, dimethacarb, dimethachlone, dimethachlor, dimethametryn, di Dimethenamid, dimethenamid-P, dimethipin, dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl carbate, dimethyl disulfide Fido, dimethyl phthalate, dimethylvinphos, dimetilan, dimexano, dimidazon, dimoxystrobin, dimpylate, dimuron, dinex, dingjunezuo, diniconazole, diniconazole-M, dinitramine, dinitrophenols, dino Dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinophenate, dinopenton, dinoprop, dinosam, dinoseb, dinosulfon, dinotefuran, dinoterb, dinoterbone, diofenolan nolan, dioxabenzofos, dioxacarb, dioxathion, dioxation, diphacin, diphacinone, diphenadione, diphenamid, diphenamide, diphenyl sulfone, diphenylamine, diphenyl sulfide, diprogulic acid , dipropalin, dipropetryn, dipterex, dipymetitrone, dipyrithione, diquat, disodium tetraborate, disosultap, disparlure, disugran, disul, disulfiram, disulfoto disulfoton, dithianon, dithichloro Dithicrofos, dithioether, dithiometon , dithiopyr, diuron, dixanthogen, d-limonene, DMDS, DMPA, DNOC, dodemorph, dodicin, dodine, dofenapine, doguadine, dominicalure, doramectin, DPC, drazoxolone, DSMA, d-trans-allethrin, d-trans-resmethrin, dufulin, dymron, EBEP, EBP, ebufos, ecdysterone, echlomezol, EDB, EDC, EDDP, edifenphos, eglinazine, emamectin, EMPC, empenthrin ), enadenine, endosulfan, endothal, endo Endothall, endothion, endrin, enestroburin, enilconazole, enoxastrobin, ephirsulfonate, EPN, epocholeone, epofenonane, epoxiconazole, eprinomectin, epronaz naz), EPTC, erbon, ergocalciferol, erlujixiancaoan, esdepallethrine, esfenvalerate, ESP, esprocarb, etacelasil, etaconazole, etaphos, etem, ethaboxam, ethachlor, etha Ethifluralin, ethametsulfuron, ethaprochlor, ethephon, ethidimuron, ethifluralin ... Fencarb, ethiolate, ethion, ethiozin, ethiprole, ethirimol, ethoate-methyl, etobenzanid, ethofumesate, ethohexadiol, ethoprop, ethoprophos, ethoxyfen, ethoxyquin, ethoxysulfuron, ethychlozate, ethyl formate, ethyl pyrophosphate, ethylan, ethyl-DDD, ethylene, ethylene dibromide, ethylene Ethylene dichloride, ethylene oxide, ethylicin, ethylmercury 2,3-dichloride Hydroxypropyl mercaptide, ethylmercury acetate, ethylmercury bromide, ethylmercury chloride, ethylmercury phosphate, etinofen, ETM, etonipromy etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimphos (etrimfos), etrimphos, eugenol, EXD, famoxadone, famphur, fenac, fenamidone, fenaminosulf, phenaminestrobin, fenamiphos, fenapanil, fenarimol, fenasulam, fenazaflor, fenazaquin ), fenbuconazole, fenbutatin oxide, fenchlorazole, fenchlorphos, fenclofos, fenclorim, fenthacarb, fenfluthrin, fenfuram, fenhexamid, phenidine, fenitropan, fenitrothion, Thione, fenizon, fenjuntong, fenobucarb (fenobucarb), fenolovo, fenoprop, fenothione Fenothiocarb, fenoxacrim, fenoxanil, fenoxaprop, fenoxaprop-P, fenoxasulfo fenoxasulfone, fenoxycarb, fenpiclonil, fenpirithrin, fenpropathrin, Fenpropidin, fenpropimorph, fenpyrazamine, fenpyroximate, fenquinotrione (fenquinotrione), fenridazon, fenson, fensulfothion, fenteracol, fentiapro Fenthiaprop, fenthion, fenthion-ethyl, fentiaprop, fentin, fentrazamide, fentrifanil, fenuron, fenuron-TCA, fenvalerate, ferbam, ferimzone, ferric phosphate, ferrous sulfate, fipronil, flamprop, flamprop-M, flazasulfuron, flocumafen, flometoquin, flonicamid, florasulam, fluacrypyrim, fluazifop, fluazifop-P, fluazinam, fluazolate, fluazuron, flubendiamide, flubenzimine, flubrocythrinate, flucarbazone, flucetosulfuron , fluchloralin, flucofuron, flucycloxuron, flucythrinate, fludioxonil, fluenethyl, fluenetil, fluensulfone, flufenacet, flufenerim, flufenican, flufenoxuron, flufenoxystrobin, flufenprox, flufenpyr, flufenzine, flufiprole, Fluhexafon, flumethrin, flumetober, flumetralin, flumetsulam, flumezin, flumiclorac, flumioxazin, flumipropyn, flumorph, fluometuron, fluopicolide, fluopyram, fluorbenside, fluoridamid, fluoroacetamide, fluoroacetic acid, fluorochloridone, fluorodifen, flu Fluoroglycofen, fluoroimide, fluoromidine, fluoronitrofen, fluroxypyr, fluothiuron, fluotrimazole, fluoxastrobin, flupoxam, flupropacil, flupropadine, flupropanate, flupyradifurone, flupyrsulfuron, fluquinconazole, fluralaner, flu Flurazole, flurecol, flurenol, flu Fluridone, flurochloridone, fluromidine, fluroxypyr, flurprimidol, flurus Flursulamid, flurtamone, flusilazole, flusulfamide, flutenzine, fluthiacet, fluthiamide, flutianil, flutolanil, flutriafol, fluvalinate , fluxapyroxad, fluxofenim, folpel, folpet, fomesafen, fonofos, foramsulfuron, forchlorfenuron, formaldehyde, formetanate, formothion, formo paranate, fosamine, fosetyl, fosmethicone fosmethilan, fospirate, fosthiazate, Fostietan, frontalin, fthalide, Fuberidazole, Fukaojing, Fukaomi, Fujunmanzhi, Fulumi, Fumarin, Funaiheka Oring (funaihecaoling), fufenthiourea (fuphenthiourea), furalane (furalane), furalaxyl (furalaxyl), furamethrin (furametpyr), furan tebufenozide (furan tebufenozide), furathiocarb (furathiocarb), furcarbanil (furcarbanil), fluconazole (furconazole), fluconazole-cis, furethrin (furethrin), furfural, furilazole (furilazole), furmecyclox (furomecyclox), furophanate (furophanate), furyloxyfen (furyloxyfen), gamma-BHC, gamma-cyhalothrin (cyhalothrin), gamma-HCH, Genit, gibberellic acid, gibberellin A3, gibberellins, gliftor, glitor, glucochloralose, glufosinate (glufosinate), glufosinate-P, glyodin, glyoxime, glyphosate, glyphosine, gossyplure, grandlure, griseofulvin, guanoctine, glyphosinate-P, glyodin, glyoxime, glyphosate, glyphosine, gossyplure, grandlure, griseofulvin, guanoctine, Azatine, halacrinate, halauxifen, halfenprox, halofenozide, halosafen, halosulfuron, haloxydine , haloxyfop, haloxyfop-P, haloxyfop-R, HCA, HCB, HCH, hemel, hempa, HEOD, heptachlor, heptafluthrin, heptenophos, heptopargil, herbima Herbimycin, herbimycin A, heterophos, hexachlor, hexachloran, hexachloroacetone, hexachlorobe benzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron, hexafluoramine, hexaflurate, hexalure, hexamide, Hexazinone, hexylthiofos, hexythiazox, HHDN, holosulf, homobrassinolide, huancaiwo, huanchongjing, huan Huangcaoling, Huanjunzuo, Hydramethylnon, Hydrargaphen, Slaked lime, Hydrogen cyanamide, Hydrogen cyanide, Hydroprene, Hydroxyisoxazole, Hymexazol, Hyquincarb ), IAA, IBA, IBP, icaridin, imazalil, imazamethabe Imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, imibenconazole, imicyaphos (imicyafos), imidacloprid, imidaclothiz , iminoctadine, imiprothrin, inabenfide (inabenfide), indanofan, indaziflam, in Doxacarb, inezin, infusoria earth, iodobonil ), iodocarb, iodofenphos, iodomethane, iodine Iodosulfuron, Iofensulfuron, Ioxy Ioxynil, Ipazine, IPC, Ipconazole, Ipfu Ipfencarbazone, iprobenfos, iprodione, iprovalicarb, iprimidam, ipsdienol, ipsenol, IPSP, IPX, isamidofos, isazofos, isobenzan, isocarbamid, isocarbamide, isocarbophos, isocyanamide, isothiocyanate, isocil, isodrin, isofenphos, isofenphos s-methyl, isofetamide, isolane, isomethiozin, isonoruron, isopamphos, isopamphos isopolinate, isoprocarb, isoprocil, Isopropalin, isopropazol, isoprothiolane, isoproturon, isopyrazam, Sopirimol, isothioate, isotianil, isouron, isovaledione, isoxaben, isoxachlortole, isoxadifen, isoxaflutole, isoxapyrifop, Isoxathion, isuron, ivermectin, ixoxaben, isopamfos, isopamphos, japonilure, japothrins, jasmolin I, jasmolin II, jasmonic acid, jiahuangchongzong, diazizengguksia Olin (jiajizengxiaolin), Jiaxiangjunzhi (jiaxiangjunzhi), Jiecaowan (jiecaowan), Jiecaoxi (jiecaoxi), Jinganmycin A (jinganmycin A), Iodofenphos, juvenile hormone I, juvenile hormone II, juvenile hormone III, kadethrin, kappa-bifenthrin, kappa-tef Lutrin (kappa-tefluthrin), karbutilate, karetazan, kasugamycin, kejunlin, kelevan, ketospira Ketospiradox, diatomaceous earth, kinetin, kinoprene, chiralaxyl, kresoxim-methyl, quicaoxy (kuicaoxi), lactofen, lambda-cyhalothrin, latilure, lead arsenate, lenacil, lepimectin, leptophos, lianbenjingzhi, lime sulfur, lindane, lineatin, linuron, lirimfos, litl Litlure, Looplure, Lufenuron, Luxiancaolin, Lubdingjunzhi, Lubfumijvzhi, Lubxiancaolin, Lythidathion, M-74, M-81, MAA, Magnesium phosphide, Malathion, Maldison ), maleic hydrazide, malonoben, maltodextrin, MAMA, ma Mancopper, mancozeb, mandestrobin ), mandipropamid, maneb, matrine, ma Didox, MCC, MCP, MCPA, MCPA-thioethyl, MCPB, MCPP, mebenil, mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop-P, medimeform , medinoterb, medlure, mefenacet, mefenoxam, mefenpyr, mefluidide ), megatomoic acid, melissyl alcohol, melitoxin, MEMC, menasone, MEP, mepanipyrim, meperfluthrin, mephenate, mephosfolan, mepiquat, mepronil, meptyldinocap, mercaptodimethur, mercaptophos, mercaptophos thiol, mercaptothion, mercuric chloride, oxide Mercuric chloride, mercurous chloride, merphos, merphos oxide, mesoprazine, mesosulfuron, mesotrione, mesulfen, mesulfenphos, mesulfen, metacresol, metaflumizone, metalaxyl, metalaxyl-M, metaldehyde, metam, metamifop, metamitron, metaphos, metaxon, metazachlor, metazosulfuron, metazoxolone (metazoxolon), metconazole, mettepa, metflurazon, methabenzthiazuron, methacrifos, methalpropalin, metham, methamidophos thamidophos, methasulfocarb, methazole, metofuroxam, methibenzuron, methidathion, methiobencarb, methiocarb, methio Pyrisulfuron, methiotepa, methiozolin, methiuron, methocrotophos, metolcarb, methometon, methomyl, methoprene, metoprothrin, methoprotryne, methoquin-butyl, methothrin, methoxychlor, methoxyphen Methoxyfenozide, methoxyphenone, methyl afolate (methyl apholate), methyl bromide, methyl eugenol, methyl iodide, methyl isothiocyanate ocyanate, methyl parathion, methylacetophos, methylchloro methyldithiocarbamic acid, methyldithiocarbamic acid Methyldymron, methylene chloride, methyl-isofenphos, methylmercaptophos, methylmercaptophos oxide, methylmercaptophos thiol, methylmercury benzoate, methylmercury dicyandiamide, methylmercury pentachlorophenoxide, methylneodecanamide, methyl Methylnitrophos, methyltriazothion, methiozolin, metiram, metiram zinc, metiram-zinc, methiram Benzuron (metobenzuron), metobromuron (metobromuron), metofluthrin (metofluthrin), metolachlor (metolachlor), metolcarb (metolcarb), metometuron (metometuron), metominostrobin (metominostrobin), metosulam (metosulam ), metoxadiazone, metoxuron, metrafenone, metriam, metribuzin, metrifonate, metriphonate, metsulfovax, metsulfuron, mevinphos, mexacarbate, mieshuwei, mieshuan, miewenjuzhi, milbemectin, milbemycin oxime oxime), milneb, mima2nan, mipafox, MIPC, mirex, MNAF, moguchun, molinate, molosultap, momfluorothrin, Monalide, monisouron, monoamitraz , monochloroacetic acid, monocrotophos, monolinuron, monomehypo, monosulfiram, monosulfuron, monosultap, monuron, monuron-TCA, Morfamquat, moroxydine, morphothion, morzid, moxidectin, MPMC, MSMA, MTMC, Muscalure, myclobutanil, myclozolin ), myricyl alcohol, N-(ethylmercury)-p-toluenesulfonanilide, NAA, NAAm, nabam, naphthalofos, naled, naphthalene, naphthaleneacetamide, naphthalic anhydride, naphthalophos, naphthoxyacetic acid , naphthylacetic acid, naphthylindan-1,3-diones, naphthyloxyacetic acid, naphthylaniline naproanilide, napropamide, napropamide-M, naptalam, natamycin, NBPOS, neburea, neburon, nendrin, neonicotine, nichlorfos, niclofen, niclosamide, nicobifen, nicosulfuron n), nicotine, nicotine sulfate, nifluridide, nikkomycins, NIP, nipyraclofen, nipyralofen, nitenpyram, nithiazine, nitralin, nitrapyrin, nitrilacarb, nitrofen, nitrofluorfen, trostyrene, nitrothal-isopropyl, nobormide, nonanol, norbormide, norea, norflurazon, nornicotine, noruron, novaluron, noviflumuron, NPA, nuarimol, nurano Nuranone, OCH, octachlorodipropyl ether, octhilinone, o-dichlorobenzene, ofurace, omethoate, o-phenylphenol, orbencarb, orfralure, orthobencarb, ortho-dichlorobenzene, orthosulfamuron, oryctalure, orysastrobin, oryzalin, osthol, osthole, ostramone, ovatron, ovex, oxabetrinil, oxadiargyl, oxadiazon, oxadixyl (oxadixyl), oxamate, oxamyl, oxapyrazon, oxapyrazone, oxasulfuron, ox Oxathiapiprolin, oxaziclomefone, oxine-copper, oxine-Cu, oxolinic acid, oxpoconazole, oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton, oxyenadenine, oxyfluorfen, oxymatrine, oxytetracycline, oxythioquinox, PAC, paclobutrazol, paichongding, pallethrine, PAP, para-dichlorobenzene, parafluron, paraquat, parathion, parathion-methyl, parinol, Paris Green green), PCNB, PCP, PCP-Na, p-dichlorobenzene, PDJ, PEB pebulate, pedinex, pefurazoate, pelargonic acid, penconazole, pencycuron, pendimethicone Pendimethalin, penfenate, penflufen ), penfluron, penoxalin, penoxsulam, pentachlorophenol, pentachlorophenyl laurate, pentanochlor, penthiopyrad, pentomethrin, Pentoxazone, perchlordecone, perfluid perfluidone, permethrin, pethoxamid, PHC, phenamacril, fenamacryl-ethyl, phenaminosulf, phenazine oxide, fenetacarb, phenisopham, phenkapton, phenmedipham Phenmedipham, phenmedipham-ethyl, phenobenzuron, phenothiol, fenothrin, phenproxide, phenthoate, phenylmercuriurea, phenylmercuric acetate, phenylmercuric chloride, phenylmercuric derivatives of pyrocatechol, phenylmercuric nitrate, phenylmercuric salicylate, phorate, phosacetim , phosalone, phosametine, phosazetim, phosazetin, phoscyclotin, phosdiphen, fosetyl, phosfolan, phospholan-methyl, phosglyc Phosglycin, phosmet, phosnichlor, phosphamide, phosphamidon, phosphine, phosphinotri Phosphinothricin, phosphocarb, phosphorus, phostin, phoxim, phoxim-methyl, phthalide, phthalophos, phthalthrin, picarbutrazox, picar Picaridin, picloram, picolinafen, picoxystrobin, pimaricin, pindone, pinoxaden pinoxaden, piperalin, piperazine, piperonyl butoxide, piperonyl cyclonene, piperophos, piproctanly, piproctanyl, piprotal, pyrimeth Pirimetaphos, pirimicarb, piriminil, pirimi Pirimioxyphos, pirimiphos-ethyl, pirimiphos-methyl, pival, pivaldione, plifenate, PMA, PMP, polyb Tenths, polycarbamates, polychlorcamphene, polyethoxy Polyethoxyquinoline, polyoxin D, polyoxins, polyoxol Polyoxorim, polythialan, potassium arsenite, potassium azide, Potassium cyanate, potassium ethylxanthate, potassium naphthenate, potassium polysulfide, potassium thiocyanate, pp'-DDT, prallethrin, precocene I, precocene II, precocene III, pretilachlor , primidophos, primisulfuron, probenazole, prochloraz, proclonol, procyazine, procymidone, prodiamine, Profenofos, profluazol, profluralin, profluthrin, profoxydim, profurite-aminium, proglinadin, prohexadione, prohydrojasmon, promacyl, promecarb, promecarb, Rometon, prometryn, prometryne, promurit, pronamide, propachlor, propafos, propamidine, propamocarb, propanil, propaphos, propaquizafop, propargite, propa Lutrin (proparthrin), propazine (propazine), propetamphos (propetamphos), propham (propham), propiconazole (propiconazole), propidine (propidine), propineb (propineb), propisochlor (propisochlor), propoxur (propoxur), propoxycarbazone (propoxycarbazone), propyl isome (propyl isome) ), propyrisulfuron, propyzamide, proquinazid, prosuler, prosulfalin, prosulfocarb, prosulfuron, prothidathion (prothidathion), prothiocarb, prothioconazole, prothifos, prothoate, protrifenb Protrifenbute, Proxan, Primidophos, Prinachlor, Psoralen, Psoralene, Pidanon, Piflubumide, Pymetrozine, Pyracarbolid, Pyraclofos, Pyraclonil, Pyraclostrobin, Pyraflufen, Pyrafluprole, Pyramat, Pyrametostrobin, Pyraoxystrobin, Pyrasulfotole, Pyrazil Flumid (pyraziflumid), pyrazolate (pyrazolate), pyrazolynate (pyrazolynate), pyrazon (pyrazon), pyrazophos (pyrazophos), pyrazosulfuron (pyrazosulfuron), pyrazothion (pyrazothion), pyrazoxyfen (pyrazoxyfen), pyrethme pyrethrin, pyrethrin I, pyrethrin II, pyrethrins, pyribambenz-isopropyl, pyribambenz-propyl, pyribencarb, pyribenzoxim, pyributicarb , pyriclor, pyridaben, pyridafol, pyridalyl, pyridaphenthion, pyridaphenthione, pyridate, pyridinitril, pyrifenox, pyrifluquinazon, pyriftalid pyriftalid, pyrimetaphos, pyrimethanil, pirimicarb, pyrimidifen, pyriminobac, pyriminostrobin, pirimiphos-ethyl, pirimiphos-methyl, pyrimisulfan, pyrimitate, pyrinuron, pyriophenone, pyriprole, pyripropano pyripropanol, pyriproxyfen, pyrisoxazole, pyrithiobac, pyrrolan, pyroquilon, pyroxasulfone, pyroxsulam, pyroxsulam, pyroxazol, pyrisoxazole ... pyroxychlor, pyroxyfur, qincaosuan, qingkuling, quassia, quinacetol, quinalphos, quinalphos-methyl, quinazamid, quinclorac, quinconazole, quinmerac, quinoclamine, quinomethionate, quinonami quinonamid, quinothion, quinoxyfen, quintiofos, quintozene, quizalofop, quizalofop-P, quwenzhi, quyingding, rabenzazole, rafoxanide, R-diniconazole, rebemide, reglone, renriduron, rescalure ), resmethrin, rhodetanil, rhodojaponin-III, ribavirin, rimsulfuron, rizazo R-rizazole, R-metalaxyl, rodetanil, ronnel (ronnel), rotenone, ryania, sabadilla, sa Flufenacil, Saijunmao, Saisentong, salicylanilide, salifluofen, sanguinarine, santonin, S-bioallethrin, Schradan, scilliroside, sebuthylazine, sec Secbumeton, sedaxane, selamectin, semiamitraz, sesamex, sesamolin, Sesone, sethoxydim, sevin, shuangjian Kaolin (shuangjiaancaolin), Shuangjianankaolin (shuangjianancaolin) , S-hydroprene, siduron, sifumijvzhi, siglure, silafluofen, silatrane ), silica aerogel, silica gel, silthiofam, silthiopham, silthiophan, silvex, simazine, simeconazole, simeton, simetryn, simetryne, sintophen, S-kinoprene, hydrated lime, SMA, S-methoprene, S-metolachlor, sodium arsenite sodium, sodium azide, sodium chlorate, sodium cyanide, sodium fluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodium o-phenylphenoxide, sodium orthophenylphenoxide, sodium pentachlorophenate, sodium pentachlorophenoxide, sodium polysulfide, sodium silicofluoride, sodium tetrathiocarbonate, sodium thiocyanate, solan, sophamide, spinetoram, spinosad, spirodiclofen, spiromesifen, Spirotetramat, spiroxamine, stirofos, streptomycin, strychnine, sulcatol, sulcofuron, sulcotrione, sulfalate , sulfentrazone, sulfiram, sulfluramide (sulfluramid), sulfodiazole, sulfometuron ), sulfosate, sulfosulfuron, sulfotep ( sulfotep, sulfotepp, sulfoxaflor, sulfoxide, sulfoxime, sulfur, sulfuric acid, sulfuryl fluoride, sulglycapin, sulfosate, sulprofos, sultropen, swep, tau-fluvalinate, tavron, tazimcarb, TBTO, TBZ, TCA, TCBA, TCMTB , TCNB, TDE, tebuconazole, tebufenozide, te bufenpyrad, tebufloquin, tebupirimfos, tebutam, tebuthiuron, tecloftalam, tecnazene, tecoram, tedion, teflubenzuron, tefluthrin, tefurtrio tefuryltrione, tembotrione, temefos, temefos Temephos, Tepa, TEPP, tepraloxydim, teproloxydim, terallethrin, terbacil, terbucarb, terbuchlor, terbufos, te lumebumeton (terbumeton), terbuthylazine (terbuthylazine), terbutol (terbutol), terbutryn (terbutryne), terraclor (terraclor), terramycin (terramicin), terramycin (terramycin), tetcyclacis (tetcyclacis), tetrachloroethane, tetrachlorvinphos, tetraconazole (tetraconazole), tetradifon (tetradifon), tetradisul (tetradisul), tetrafluron (tetrafluron), tetramethrin (tetramethrin), tetramethylfluthrin (tetramethylfluthrin), tetramine (tetramine), tetranactin (tetranactin), tetraniliprole (tetraniliprole), tetrapion (tetrapion), tetrasul (tetrasul ), thallium sulfate, thallous sulfate, thenylchlor, theta-cypermethrin, thiabendazole, thiacloprid, thiadiazine, thiadifluor, thiamethoxam, thiameturon, thiapronil, thiazafluron, thiazfluron ), thiazone, thiazopyr, cyclophos, thicyofen, thidiazimin, thidiazuron , thiencarbazone, thifensulfuron, thifluzamide, thimerosal, thimet, thiobencarb, thiocarboxime, thiochlorfenphim, thiochlorphenphime, thiocyanatodinitrobenzenes, thiocyclam , thiodan, thiodiazole-copper, thiodicarb, thiofanocarb, thiofanox, thiofluoximate, thiohempa, thiomersal, thiometon, thionazin, thiophanate, thiophanate-ethyl, thiophanate-methyl, thiophos (thiophos), thioquinox, thiosemicarbazide, thiosultap, thiotepa, thioxamyl, thiram, thiuram, thuringiensin, thiabendazole, Tiadinil, tiafenacil, tiaojiean ), TIBA, tifatol, thiocarbazil, thioclorim, tioxazafen, tioximid, tirpar tirpate, TMTD, tolclofos-methyl, tolfenpyrad, tolprocarb, tolpyralate, tolyfluanid, tolylfluanid, tolylmercury acetate To, tomarin, topramezone, toxaphene , TPN, tralkoxydim, tralocythrin, tralomethrin, tralopyril, transfluthrin thrin, transpermethrin, tretamine, tri Acontanol, triadimefon, triadimenol (triadimenol), triafamone, triallate, tri- Tri-allate, triamiphos, triapenthenol, triarathene, triarimol, triasulf triasulfuron, triazamate, triazbutil, triaziflam, triazophos, triazothion, triazoxide, tribasic copper chloride, tribasic copper sulfate, tribenuro tribenuron, tribufos, tributyltin oxide, tricamba, trichlamide, triclopyr, trichlorfo trichlorfon, trichlormetaphos-3, trichloronate (trichloronat), trichloronate, trichlorotrinitrobenzene Trichlorphon, triclopyr, and triclopyrica Triclopyricarb, tricresol, tricyclazole, tricyclohexyltin hydroxide, tridemorph, tridiphane, trietazine, trifenmorph, triphenofos, trifloxystrobin, trifloxystrobin Sulfuron (trifloxysulfuron), trifludimoxazin, triflu triflumezopyrim, triflumizole, triflumuro triflumuron, trifluralin, triflusulfuron, trifop, trifopsime, triforine ), trihydroxytriazine, trimedlure, trimethacarb, trimeturon, trinexapac, triphenyltin, triprene, tripropindan, triptolide, tritac, trithialan, triticonazole, tritosulfuron, trunc-call, tuoyelin, uniconazole, uniconazole-P, urbacide, uredepa, valerate, validamay Syn, validamycin A, valifenalate, valone, vami Vamidothion, Vanguard, Vaniliprole, Vernolate, vinclozolin, vitamin D3, warfarin, xiaochongliulin, xinjunan, xiwojunan, xiwojunzhi, XMC, xic Xylachlor, xylenols, xylylcarb, xymiazole, yishijing, zalilamid, zeatin, zengxiaoan, zengxiaolin, zeta-cypermethrin, zinc naphthenate, zinc phosphide, zinc thiazole, zinc thiozole, zinc trichlorophenate, zinc trichlorophenoxide trichlorophenoxide), zineb, ziram, zolaprofos, zoocoumarin, zoxamide, zuoanjunzhi, zuocaoan, zuo Junchi (zuojunzhi), Zuomihuanglong (zuomihuanglong), α-chlorohydrin, α-ecdysone, α-multistriatin, α-naphthaleneacetic acid, and β-ecdysone;

[0013] (2) The molecule shown below (a) N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide (hereinafter "AI-1") [ka] (b) (3S,6S,7R,8R)-8-benzyl-3-(3-((isobutyryloxy)methoxy)-4-methoxypicolinamido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (hereinafter referred to as "AI-2") [ka]

[0014] (3) A molecule known as Lotilaner, which has the following structure: [ka]

[0015] (4) the following molecules listed in Table A: Table AM# Structure - Active Ingredients [Table 1-1] [Table 1-2]

[0016] As used in this disclosure, each of the above is an active ingredient. For further information, see the "Compendium of Pesticide Common Names" (found at Alanwood.net) and various editions of "The Pesticide Manual," including the online version (found at bcpcdata.com).

[0017] Particularly preferred selected active ingredients are 1,3-dichloropropene, chlorpyrifos, hexaflumuron, methoxyfenozide, noviflumuron, spinetoram, spinosad, and sulfoxaflor (hereinafter "AIGA-2").

[0018] Furthermore, other particularly preferred selected active ingredients include acequinocyl, acetamiprid, acetoprole, avermectin, azinphos-methyl, bifenazate, bifenazate, These are fenthrin, carbaryl, carbofuran, chlorfenapyr, chlorfluazuron, chromafenozide, clothianidin, cyfluthrin, cypermethrin, deltamethrin, diafenthiuron, emamectin benzoate, endosulfan, esfenvalerate, ethiprole, etoxazole, fipronil, flonicamid, fluacrypyrim, gamma-cyhalothrin, halofenozide, indoxacarb, lambda-cyhalothrin, lufenuron, malathion, methomyl, novaluron, permethrin, pyridalyl, pyrimidifen, spirodiclofen, tebufenozide, thiacloprid, thiamethoxam, thiodicarb, tolfenpyrad, and zeta-cypermethrin (hereinafter referred to as "AIGA-3").

[0019] The term "alkenyl" refers to an acyclic, unsaturated (at least one) alkyl group consisting of carbon and hydrogen. (carbon-carbon double bond), branched or unbranched substituents, for example, vinyl, allyl, butenyl, pentenyl, and hexenyl.

[0020] The term "alkenyloxy" refers to an alkenyl further consisting of a carbon-oxygen single bond, for example, allyloxy, butenyloxy, pentenyloxy, hexenyloxy.

[0021] The term "alkoxy" refers to an alkyl further consisting of a carbon-oxygen single bond, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, and tert-butoxy.

[0022] The term "alkyl" refers to an acyclic, saturated, branched or unbranched substituent composed of carbon and hydrogen, such as methyl, ethyl, propyl, isopropyl, butyl, and tert-butyl. It means chill.

[0023] The term "alkynyl" refers to an acyclic, unsaturated (at least one) alkyl group consisting of carbon and hydrogen. (carbon-carbon triple bond), branched or unbranched substituents, for example, ethynyl, propargyl, butynyl, and pentynyl.

[0024] The term "alkynyloxy" refers to an alkynyl further consisting of a carbon-oxygen single bond, for example, pentynyloxy, hexynyloxy, heptynyloxy, and octynyloxy.

[0025] The term "aryl" means a cyclic, aromatic substituent composed of hydrogen and carbon, for example, phenyl, naphthyl, and biphenyl.

[0026] The term "biopesticide" refers to microbial biological pest control agents, generally applied in a manner similar to chemical pesticides. They are usually bacterial, although some examples are fungal control agents, including Trichoderma spp. and Ampelomyces quisqualis. One well-known example of a biopesticide is Bacillus species, which cause bacterial diseases in Lepidoptera, Coleoptera, and Diptera. Biopesticides include entomopathogenic fungi (e.g., Metarhizium anisopliae), entomopathogenic nematodes (e.g., Steinernema feltiae), and entomopathogenic viruses (e.g., Cydia pomonella). (Cydia pomonella) granulovirus-based products. Other examples of organisms include, but are not limited to, baculoviruses, protozoa, and microsporidia.For the avoidance of doubt, a biopesticide is an active ingredient.

[0027] The term "cycloalkenyl" refers to a monocyclic or polycyclic, unsaturated (at least one carbon-carbon double bond) substituent composed of carbon and hydrogen, e.g., cyclobutenyl ... peropentenyl, cyclohexenyl, norbornenyl, bicyclo[2.2.2]octenyl, tetrahydrofuran It means trihydronaphthyl, hexahydronaphthyl, and octahydronaphthyl.

[0028] The term "cycloalkenyloxy" refers to a cycloalkenyl further consisting of a carbon-oxygen single bond, for example, cyclobutenyloxy, cyclopentenyloxy, norbornenyloxy, and bicyclo[2.2.2]octenyloxy.

[0029] The term "cycloalkyl" means a mono- or polycyclic, saturated substituent composed of carbon and hydrogen, for example, cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, bicyclo[2.2.2]octyl, and decahydronaphthyl.

[0030] The term "cycloalkoxy" refers to a cycloalkyl further consisting of a carbon-oxygen single bond, such as cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, norbornyloxy, and bicyclo[2.2.2]octyloxy.

[0031] The term "halo" means fluoro, chloro, bromo, and iodo.

[0032] The term "haloalkoxy" further refers to one to the maximum possible number of identical or different alkyl groups. By "alkoxy" is meant alkoxy consisting of halo, such as fluoromethoxy, trifluoromethoxy, 2,2-difluoropropoxy, chloromethoxy, trichloromethoxy, 1,1,2,2-tetrafluoroethoxy, and pentafluoroethoxy.

[0033] The term "haloalkyl" further refers to one to the maximum possible number of identical or different alkyl groups. It also refers to alkyl groups consisting of halo, such as fluoromethyl, trifluoromethyl, 2,2-difluoropropyl, chloromethyl, trichloromethyl, and 1,1,2,2-tetrafluoroethyl.

[0034] The term "heterocyclyl" means a cyclic substituent which may be aromatic, fully saturated, or partially or fully unsaturated, wherein the cyclic structure has at least one carbon atom. and at least one heteroatom, the heteroatom being nitrogen, sulfur, or oxygen. Examples include:

[0035] (1) Aromatic Heterocyclyl Substituents Examples of aromatic heterocyclyl substituents include, but are not limited to: However, benzofuranyl, benzimidazolyl, benzisothiazolyl, benzisoxazolyl, benzothienyl, benzothiazolyl, benzothiophenyl, benzoxazolyl, cinnolinyl, furanyl, imidazolyl, imidazolylpyridinyl, indazolyl, indolyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, oxadiazolyl, oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl, pyrazolyl, pyrazolopyridinyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, pyrrolopyridinyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrazolyl, thiadiazolyl, thiazolinyl, thiazolyl, thienyl, triazinyl, [1,2,4]thiazolyl Zolo[1,5-c]pyrimidinyl, and triazolyl; (2) Examples of fully saturated heterocyclyl substituents include, but are not limited to, piperazine. phenyl, piperidinyl, morpholinyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiophenyl, tetrahydrothiophenyl-oxide, and tetrahydrothiophenyl- Contains dihydrothiophenyl dioxide; (3) Examples of partially or fully unsaturated heterocyclyl substituents include, but are not limited to: However, 2,3-dihydro-1H-imidazolonyl, 4,5-dihydro-isoxazolyl, 4,5-dihydro-oxazolyl, 2,3-dihydrophthalazinyl, 2,3-dihydrophthalazine-1,4-dionyl, 4,5-dihydro-1H-pyrazolyl, 2,3-dihydro-[1,3,4]-oxadiazolyl, 2,5-dioxoimidazolidinyl, 2,4-dioxo-1,3-diazaspiro[4.4]nonanylisoxazolidinonyl (nonanylisoxa zolidinonyl, indolinyl, imidazolidinonyl, isoxazolidinonyl, oxazolidinonyl, pyrimidine-2,4(1H,3H)-dionyl, pyrrolidinonyl, 1,2,3,4-tetrahydro-pyrimidinyl, 1,2,3,4-tetrahydro-quinolinyl, and thioxothiazolidinonyl; and (4) Additional examples of heterocyclyls include: [ka] Includes:

[0036] The term "area" refers to a habitat, breeding ground, plant, seed, soil, material, or environment in which pests grow, can grow, or can move about. For example, an area may be an area where crops, trees, fruit, grain, forage, vines, lawns, and / or ornamentals grow, an area where livestock live, an interior or exterior surface of a structure (such as where grain is stored), construction materials used in a structure (such as impregnated wood), and the soil surrounding a structure.

[0037] The term "MoA substance" means an active ingredient having a mechanism of action ("MoA") as set out in the IRAC MoA classification v. 7.3 (listed at irac-online.org.), which refers to the following groups: (1) It is an acetylcholinesterase (AChE) inhibitor and contains the following active ingredients: Carb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fu Enobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, xylylcarb, Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famflu, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyaphos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Meta Midophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, Includes lopetamfos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, and vamidothion. (2) A GABA-gated chloride channel antagonist containing the following active ingredients: These include aldene, endosulfan, ethiprole, and fipronil. (3) Sodium channel modulators, including the following active ingredients: acrinathrin; Allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bifenthrin Oallethrin, Bioallethrin S-cyclopentenyl, Bioresmethrin, Cycloprothrin, Cyfluthrin, Beta-Cyfluthrin, Cyhalothrin, Lambda-Cyhalothrin, Gamma-Cyhalothrin, Cypermethrin, Alpha-Cypermethrin, Beta-Cypermethrin, Theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empenthrin, [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imip Lothrin, kadethrin, permethrin, fenothrin [(1R)-trans-isomer], prallethrin, pyrethrins (Ceratitis gramineus), resmethrin, silafluofen, tefluthrin, Tetramethrin, tetramethrin [(1R)-isomer], tralomethrin, and transflut Contains phosphorus, as well as methoxychlor. (4) Nicotinic acetylcholine receptor (nAChR) agonists, including the following active ingredients: (4A) Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, (4B) Nicotine, (4C) sulfoxaflor, (4D) flupyradifurone, (4E) Includes triflumezopyrim and dichloromezothiaz. (5) Nicotinic acetylcholine receptor (nAChR) allosteric activators, including the following active ingredients: spinetoram, and spinosad. (6) Chloride channel activators, including the following active ingredients: abamectin, emma Includes mectin benzoate, lepimectin, and milbemectin. (7) Juvenile hormone mimics, including the following active ingredients: hydroprene, kinoprene, methicillin, methicillin-containing compounds. Includes topren, fenoxycarb, and pyriproxyfen. (8) It is a multi-type non-specific (multi-site) inhibitor, and contains the following active ingredients: methyl bromide, chloro Includes picrin, sulfuryl fluoride, borax, and tartar emetic. (9) Chordotonic organ modulators, including the following active ingredients: pymetrozine and flonizine Contains amide. (10) Mite growth inhibitors, including the following active ingredients: clofentezine, hexythiazox, diflobidazine, and etoxazole. (11) A microbial disruptor of the insect midgut membrane, comprising the following active ingredients: Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, and Bacillus thuringiensis subsp. tenebrionae. tenebrionenis, Bt crop proteins (Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1), and Bacillus sphaericus. (12) Mitochondrial ATP synthase inhibitors, including the following active ingredients: tetradifon; Includes propargite, azocyclotin, cyhexatin, fenbutatin oxide, and diafenthiuron. (13) Uncouplers of oxidative phosphorylation via disruption of the proton gradient, including the following active ingredients: chlorfenapyr, DNOC, and sulfluramide. (14) A nicotinic acetylcholine receptor (nAChR) channel blocker with the following activities: The active ingredients, bensultap, cartap hydrochloride, thiocyclam, and thiosultap sodium Contains sodium. (15) Chitin biosynthesis inhibitor, type 0, containing the following active ingredients: bistrifluron; Includes chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron. (16) Chitin biosynthesis inhibitor, type 1, containing the following active ingredient: buprofezin nothing. (17) A molting disruptant for dipterans, containing the following active ingredient: cyromazine. (18) Ecdysone receptor agonists, including the following active ingredients: chromafenozide, halofenozide, methoxyfenozide, and tebufenozide. (19) Octopamine receptor agonists, including the following active ingredient: amitraz. (20) Mitochondrial complex III electron transport inhibitors, including the following active ingredients: hydrame Includes tilnon, acequinocyl, and fluacrypyrim. (21) A mitochondrial complex I electron transport inhibitor, which contains the following active ingredient: Fenazaki These include benzophenone, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, and rotenone. (22) A voltage-gated sodium channel blocker, including the following active ingredients: indoxacarb and metaflumizone. (23) Acetyl CoA carboxylase inhibitors, including the following active ingredients: Spirodiclo These include phen, spiromesifen, and spirotetramat. (24) A mitochondrial complex IV electron transport inhibitor, containing the following active ingredients: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, and cyanide. (25) Mitochondrial complex II electron transport inhibitors, including the following active ingredients: cyenopyrafen and cyflumetofen. (28) Ryanodine receptor modulators, including the following active ingredients: chlorantraniliprole, cyantraniliprole, and flubendiamide. Groups 26 and 27 are not assigned in this version of the classification scheme. Additionally, there is Group UN, which contains active ingredients with unknown or unclear mechanisms of action. This group includes the following active ingredients: azadirachtin, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolite, dicofol, pyridalyl, and pyrifluquinazone. The term "pest" means an organism that is harmful to humans or human concerns (crops, food, livestock, etc.), said organism being from the phylum Arthropoda, Mollusca, or Nematoda. Specific examples are ants, aphids, bedbugs, beetles, silverfish, caterpillars, cockroaches, Crickets, earwigs, fleas, flies, grasshoppers, grubs, hornets, killer bees, leafhoppers, lice, locusts, maggots, mites, moths, nematodes, planthoppers, psyllids, sawflies, scale insects, silverfish, slugs, snails, spiders, springtails, stink bugs, symphytes, termites, thrips, ticks, digger wasps, whiteflies, and wireworms.

[0038] Further examples are the following categories of pests: (1) The subphyla Chelicerata, Myriapoda, and Hexapoda. (2) Arachnida, Associated Class, and Insecta. (3) Order Phthiraptera. A non-exhaustive list of specific genera includes, but is not limited to, Phthiraptera ... Haematopinus spp., Hoplopleura spp., Linognathus Linognathus spp., Pediculus spp., Polyplax spp., Solenopotes spp., and Neohaematopinis Neohaematopinis spp. A non-exhaustive list of specific species includes, but is not limited to, Haematopinus asini, Haematopinus suis, Linognathus setosus, Linognathus ovillus, Pediculus humanus capitis, Pediculus humanus humanus, and This includes Pthirus pubis. (4) Coleoptera. A non-exhaustive list of specific genera includes, but is not limited to, Acanthoceridae Acanthoscelides spp., Agriotes spp., Antonomus Anthonomus spp., Apion spp., Apogonia spp., Araecerus spp., Aulacophora spp., Bruchus spp., Cerosterna spp., Cerotoma spp. Cerotoma spp., Ceutorhynchus spp., Chaetocnema spp. (Chaetocnema spp.), Colaspis spp., Ctenicera spp. spp.), Curculio spp., Cyclocepahla spp. ), Diabrotica spp., Dinoderu spp., Gnathocerus spp., Hemicoelus spp., Heterobos Heterobostruchus spp., Hypera spp., Ips spp., Lyctus spp., Megascelis spp., Meligethes spp., Mezium spp., Niptus spp., Otiorhynchus spp., Pantomorus spp., Phyllophaga spp., Phloreta spp., Ptinus spp., Rhizotrogus spp., Rhynchites spp. Rhynchites spp., Rhynchophorus spp., Scolytus spp. A non-exhaustive list of specific species includes, but is not limited to, Acanthoscelides obtectus, Agrilus planipennis, Ahasverus advena, Alphitobiu, and Tribolium spp. Alphitobius diaperinus, Anoplophora glabripennis, Anthonomus grandis, Anthrenus verbasci, Anthrenus falvipes, Ataenius spretulus, Atmaria linearis, Attagenus unicolor, Bochinodere Bothynoderes punctiventris, Bruchus pisorum, Callosobruchus maculatus, Karpophy Carpophilus hemipterus, Cassida vittata, Cathartus quadricollis, Cerotoma trifurcata, Ceutorhynchus assimilis, Ceutorhynchus Ceutorhynchus napi, Conoderus scalaris, Conoderus stigmosus, Conotrachelus nenuphar, Cotinis nitida, Cryocerus as Crioceris asparagi, Cryptolestes ferrugineus, Cryptolestes pusillus, Cryptoleste Cryptolestes turcicus, Cylindrocopturus adspersus, Deporaus marginatuss, Dermestes lardarius, Dermestes maculatus, Epilachna varivestis, Euvrilletta peltata, Faustinus cubae, Hylobius pales, Hylotrupes bajulus, Hypera postica, Hypothenemus hampei, Lasioderma serricorne, Leptionotarsa ​​decemkineata, Limonius canus canus), Liogenys fuscus, Liogenys suturalis, Lissorhoptrus oryzophilus, Lophocateres pusillus, Lyctus planicollis , Maecolaspis joliveti, Melanotus communis, Meligethes aeneus, Meloronta melo Melolontha melolontha, red-legged star beetle (Necrobia rufipes), Obere Oberea brevis, Oberea linearis, Oryctes rhinoceros, Oryzaephilus mercator mercator, Oryzaephilus surinamensis, Oulema melanopus, Oulema oryzae, Phyllophaga cuyabana, Polycaon stoutti, Popillia japonica, Prostephanus tornakatsu Prostephanus truncatus, Rhyzopertha dominica, Sitona lineatus, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum, Tenebroides mauritanicus, Tribolium castaneum, These include Tribolium confusum, Trogoderma granarium, Trogoderma variabile, Xestobium rufovillosum, and Zabrus tenebrioides. (5) Dermoptera. A non-exhaustive list of specific species includes, but is not limited to, Forficula Includes Forficula auricularia. (6) Blattella. A non-exhaustive list of specific species includes, but is not limited to, Blattella Blattella germanica, Blattella asahinai These include Blatta orientalis, Blatta lateralis, Parcoblatta pennsylvanica, Periplaneta americana, Periplaneta australasiae, Periplaneta brunnea, Periplaneta fuliginosa, Pycnoscelus surinamensis, and Supella longipalpa. (7) Diptera. A non-exhaustive list of specific genera includes, but is not limited to, Aedes spp., Agromyza spp., Anastrepha spp., Anopheles spp., Bactrocera spp., Ceratitis spp., Chrysops spp., Cochliomyia spp., and others. Cochliomyia spp., Contarinia spp., Culex spp., Culicoides spp., Dasineura spp., Delia spp., Drosophila spp., Fannia spp. (Fannia spp.), Hylemyia spp., Liriomyza spp., Musca spp., Phorbia spp., Pollenia spp., Psychoda spp., Simulium spp., Taba Tabanus spp., and Tipula spp. Certain species of non- An exhaustive list includes, but is not limited to, Agromyza frontella, Anastrepha suspensa, and Anastrepha ludens. (Anastrepha ludens), Anastrepha obliqua, Bactro Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera invadens, Bactrocera Bactrocera zonata, Ceratitis capitata, Dashi Dasineura brassicae, Delia platura, Fannia canicularis, Fannia scalaris, Gasterophilus intestinalis, Gracillia perseae, Haematobia irritans, Hypoderma lineatum, Liriomyza brassicae, Melophagus ovinus, Musca autumnalis, Musca domestica, Oestrus ovis, Oscinella frit, Pegomya betae, Piophila casei, Psilla rosae (Psila rosae), Rhagoletis cerasi, Rhagoletis pomonella, Rhagoletis mendax, Sithodip These include Sitodiplosis mosellana, and Stomoxys calcitrans. (8) Hemiptera. A non-exhaustive list of specific genera includes, but is not limited to, Adelges species. (Adelges spp.), Aulacaspis spp., Aphrophora spp., Aphis spp., Bemisia spp., Ceroplastes spp., Chionaspis spp., Chrysomuff Chrysomphalus spp., Coccus spp., Empoasca spp. (Empoasca spp.), Euschistus spp., Lepidosaphes spp., Lagynotomus spp., Lygus spp. , Macrosiphum spp., Nephotettix spp., Nezara spp., Nilaparvata spp., Philaenus spp. Philaenus spp., Phytocoris spp., Piezodorus spp., Planococcus spp., Pseudococcus spp., Rhopalosiphum spp., Saissetia spp., Therioaphis spp., Toumeyella spp., Toxoptera spp., Trialeurodes spp. spp.), Triatoma spp., and Unaspis spp. A non-exhaustive list of specific species includes, but is not limited to, Acrosternum hilare, Acyrthosiphon pisum, Alley Aleyrodes proletella, Aleurodicus dispersus, Aleurothrixus floccosus, Amrasca biguttula biguttula, Aonijera aura Aonidiella aurantii, Aphis gossypii, Aphis Aphis glycines, Aphis pomi, Aulacorthum solani, Bactericera cockerelli, Bagrada hilaris, Bemisia argentifolii tifolii, Bemisia tabaci, Blissus leucopterus, Boisea trivittata, Brachycorynella Brachycorynella asparagi, Brevennia rehi, Brevicoryne brassicae, Cacopsylla pyri, Cacopsylla pyricola, Calocoris norvegicus, Ceroplastes rubens, Simex Cimex hemipterus, Cimex lectularius , Dagbertus fasciatus, Dichelops furcatus, Diuraphis noxia, Diaphorina citri, Dysaphis plantaginea, Dysdercus suturellus, Edessa meditabunda, Eriosoma lanigerum, Eurygaster maura, Euschistus conspersus, E Euschistus heros, Euschistus servus, Halyomorpha halys, Helopeltis antonii, Helopeltis theivora, Iseria pul Oak (Icerya purchasi), Idioscopus nitidulus, La Laodelphax striatellus, Leptocorisa oratorius, Leptocorisa varicornis, Lygus hesperus, Maconellicoccus hirsutus, Macrosiphum euphorbiae, Macrosiphum granarium, Macrosiphum rosae, Macrosteles quadrilineatus, Mahanarva frimbiolata, Megacopta cribraria (Megacopta cribraria), Metopolophium dirhodum , Mictis longicornis, Myzus persicae, Nephotettix cincticeps, Neurocolpus longirostris, Nezara viridula, Nilaparvata lugens, Parlatoria perganzii Parlatoria pergandii, Parlatoria ziziphi, Peregrinus maidis, Phylloxera vitifoliae, Physokermes piceae, Phytocoris californicus, Phytocoris relativus, Piezodorus guildinii, Poecillocapsus Poecilocapsus lineatus, Psallus vaccinicola, Pseudacysta perseae, Pseudococcus brevipes, Quadraspidiotus perniciosus, Rhopalosiphum maidis, Rhopalosiphum padi, Saissetia oleae, Scapto Scaptocoris castanea, Schizaphis graminum, Sitobion avenae, Sogatella furcifera, Trialeurodes vaporariorum, Trialeurodes abutiloneus, Unaspis yanonensis and Zulia entrerriana Included. (9) Hymenoptera. A non-exhaustive list of specific genera includes, but is not limited to, Acromyrmecoptera. Acromyrmex spp., Atta spp., Camponotus spp., Diprion spp., Dolichovespula spp. ), Formica spp., Monomorium spp., Neodymium Neodiprion spp., Paratrechina spp., Fade These include Pheidole spp., Pogonomyrmex spp., Polistes spp., Solenopsis spp., Technomyrmex spp., Tetramorium spp., Vespula spp., Vespa spp., and Xylocopa spp. A non-exhaustive list of specific species includes, but is not limited to, Athalia rosae, Atta texana, Caliroa cerasi, Cimbex americana, Iridomyrmex humilis, Linepithema humile, Mellifera scutellata, Monomorium minimum, Monomorium Monomorium pharaonis, Neodiprion certifer sertifer), Solenopsis invicta, Solenopsis gemmi Nata (Solenopsis geminata), Solenopsis molesta, Solenopsis These include Solenopsis richtery, Solenopsis xyloni, Tapinoma sessile, and Wasmannia auropunctata. (10) Isoptera. A non-exhaustive list of specific genera includes, but is not limited to, Coptotermes spp., Cornitermes spp., Cryptotermes spp., Heterotermes spp., Kalotermes spp., Incisitermes spp., Macrotermes spp., Marginitermes spp., Microcerotermes spp., and Procornitermes spp. spp.), Reticulitermes spp., Schedorhinotermes spp., and Zootermopsis spp. A non-exhaustive list of specific species includes, but is not limited to, Coptotermes acinus Coptotermes acinaciformis, Coptotermes curvicunasus curvignathus, Coptotermes frenchi, Coptotermes formosanus, Coptotermes gestroi, Cryptotermes brevis, Heterotermes aureus, Heterotermes tenuis, Incisitermes minor, Incisitermes snyderi, Microtermes obesi, Nasti Nasutitermes corniger, Odontotermes formosanus, Odontotermes obesus, Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermes flavipes, Reticulitermes hageni, Reticulitermes hesperus, Reticulitermes santonensis, Reticulitermes speratus, Reticulitermes tibialis, and Reticulitermes This includes Reticulitermes virginicus. (11) Lepidoptera. A non-exhaustive list of specific genera includes, but is not limited to, Adoxophyes spp., Agrotis spp., and Argyrotaenia spp. (Argyrotaenia spp.), Cacoecia spp., Caloptilia spp., Chilo spp., Chrysodeixis spp., Colias spp., Crambus spp., Diaphania spp., Diatraea spp., Earias spp. , Ephestia spp., Epimecis spp., Feltia spp., Gortyna spp., Helicoverpa spp. spp.), Heliothis spp., Indarbela spp., Lithocolletis spp., Loxagrotis spp., Malacosoma spp., Nemapogon spp., Peridro Peridroma spp., Phyllonorycter spp., Pseuda Includes Pseudaletia spp., Plutella spp., Sesamia spp., Spodoptera spp., Synanthedon spp., and Yponomeuta spp. Non-exhaustive list of specific species The list includes, but is not limited to, Achaea janata, Adoxophyae Adoxophyes orana, Agrotis ipsilon, Ara Alabama argillacea, Amorbia cuneana ), Amyelois transitella, Anacamptodes defectaria, Anarsia lineatella ), Anomis sabulifera, Anticarsia gemmatalis, Archips argyrospila, Archips Archips rosana, Argyrotaenia citrana, Autographa gamma, Bonagota cranaodes cranaodes), Borbo cinnara, Buculatrix tulbergii (Bucculatrix thurberiella), Capua reticulana, Carposina niponensis, Chlumetia transversa, Choristoneura rosaceana, Knafalok Cnaphalocrocis medinalis, Conopomorpha cramerella, Corcyra cephalonica, Cossus cossus, Cydia caryana, Cydia funebrana, Cydia molesta, Cydia nigricana, Cydia pomonella, Darna didacta, Diaphania nitidalis, Diatraea saccharalis, Diatraea grandiosella ), Earias insulana, Earias vittella, Ecdytolopha aurantianum, Elasmopa Elasmopalpus lignosellus, Ephestia cautella, Ephestia elutella, Ephestia kuehniella, Epinotia aporema, Epiphi Epiphyas postvittana, Erionota thrax, Estigmene acrea, Eupoecilia ambiguera (Eupoecilia ambiguella), Euxoa auxiliaris, moth Galleria mellonella, Grapholita molesta, Hedylepta indicata, Helicoverpa armigera, Helicoverpa zea, Heliothis virescens, Hellula undalis, Keiferia lycopersicella, Leucinodes orbonalis, Leucoptera coffeella, Leucoptera Leucoptera malifoliella, Lobesia botrana, Loxagrotis albicosta, Lymantria dispar, Lyonetia clerkella, Mahasena corbetti, Mamestra brassicae, Ma Manduca sexta, Maruca testulalis, Metisa plana, Mythimna unipuncta, Neoleucinodes elegantalis, Nymphula depuncta Squirrel (Nymphula depunctalis), Operophtera brumata, Ostrinia nubilalis, Oxydia vesulia, Pandemis cerasana, Pandemis heparana, Papilio demodocus, Pectinophora gossypiae Pectinophora gossypiella, Peridroma saucia, Perileucoptera coffeella, Phthorimaea operculella, Phyllocnistis citrella, Phyllonorycter blancardella, Pieris rapa Pieris rapae, Plathypena scabra, Platinota ida Platynota idaeusalis, Plodia interpunctella, Plutella xylostella, Polychrosis viteana, Prays endocarpa, Prays oleae, Pseudaletia unipuncta , Pseudoplusia includens, Rachiplusia nu, Scirpophaga incertulas, Sesamia inferens, Sesamia nonagrioides, Setora nitens, Sitotroga cerealella cerealella, Sparganotis pilleriana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera eridania, Thecla basilides (Thecla basilides), Tinea pellionella, Tinea biseri Tineola bisselliella, Trichoplusia ni, Ivy fly These include Tuta absoluta, Zeuzera coffeae, and Zeuzea pyrina. (12) Order: Pycnonotida. A non-exhaustive list of specific genera includes, but is not limited to, Anaticola spp., Bovicola spp., Chelopistes spp., Goniodes spp., Menacanthus spp., and Trichodectes spp. A non-exhaustive list of specific species includes, but is not limited to, Anaticola spp., Bovicola spp., Chelopistes spp., Goniodes spp., Menacanthus spp., and Trichodectes spp. The list includes, but is not limited to, Bovicola bovis, Bovicola caprae, Bovicola ovis, Chelopistes meleagridis, Goniodes dissimilis, Goniodes gigas, Menacanthus stramineus, Menopon gallinae, and Trichodectes canis. (13) Orthoptera. A non-exhaustive list of specific genera includes, but is not limited to, Melanoplus spp., and Pterophylla spp. A non-exhaustive list of species includes, but is not limited to, Acheta domesticus, Anabrus simplex, Gryllotalpa africana, and Gryllotalpa australis. , Gryllotalpa brachyptera, Gryllotalpa hexada Gryllotalpa hexadactyla, Locusta migratoria , Microcentrum retinerve, Schistocerca gregaria, and Scudderia furcata. (14) Psocoptera. A non-exhaustive list of specific species includes, but is not limited to, Liposcelis decolor, Liposcelis entomophila, Lachesilla quercus, and Trogium pulsatorium. do. (15) Order Siphonaptera. A non-exhaustive list of specific species includes, but is not limited to, Ceratophyllus gallinae, Ceratophyllus niger, Ctenocephalides canis, Ctenocephalides felis, and Pulex irritans. It can be enjoyed. (16) Thysanoptera. A non-exhaustive list of specific genera includes, but is not limited to, Caryothrips Caliothrips spp., Frankliniella spp., Scirtothrips spp., and Thrips spp. A non-exhaustive list of specific species includes, but is not limited to, Frankliniella bispinosa, Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella williamsi, Heliothrips spp. Heliothrips haemorrhoidalis, Lipihorothrips cruen Rhipiphorothrips cruentatus, Scirtothrips citri, Scirtothrips dorsalis, Taeniothrips rhopalantennalis, Thrips hawaiiensis, Thrips nigropilosus, Thrips orientalis, Thrips palmi, and Tri Includes Thrips tabaci. (17) Thymidales. A non-exhaustive list of specific genera includes, but is not limited to, Lepisma spp., and Thermobia spp. (18) Order Acari. A non-exhaustive list of specific genera includes, but is not limited to, Acarus spp., Aculops spp., Argus spp., Brachyuru ... - Includes Boophilus spp., Demodex spp., Dermacentor spp., Epitrimerus spp., Eriophyes spp., Ixodes spp., Oligonychus spp., Panonychus spp., Rhizoglyphus spp., and Tetranychus spp. A non-exhaustive list of specific species The list includes, but is not limited to, Acarapis woodi, Acarus siro, Aceria mangiferae, Aculops lycopersici, Aculus pelekassi, A Aculus schlechtendali, Amblyomma americanum, Brevipalpus obovatus, Brevipalpus Brevipalpus phoenicis, Dermacentor variabilis, Dermatophagoides pteronyssinus, Eotetranychus carpini, Liponyssoides sanguineus, Notoedres cati, Oligonychus coffeae, Oligonychus ilisi Oligonychus ilicis, Ornithonyssus bacoti, Panonychus citri, Panonychus ulmi, Phyllocoptruta oleivora, Polyphagotarsonemus la Polyphagotarsonemus latus, Rhipicephalus sanguineus sanguineus, Sarcoptes scabiei, Tegolophus perseaflorae, Tetranychus urticae, Tyrophagus longior, and Varroa destructor. (19) Araneae. A non-exhaustive list of specific genera includes, but is not limited to, Loxosceles spp., Latrodectus spp., and Atlas. A non-exhaustive list of specific species includes, but is not limited to, Loxosceles reclusa, Latrodectus mactans, and Atrax robustus. (20) Class Connecticut. A non-exhaustive list of specific species includes, but is not limited to, Scutigerella immaculata. (21) Collembola. A non-exhaustive list of specific species includes, but is not limited to, Bourletiella hortensis, Onychiurus armatus, us), Onychiurus fimetarius, and Smintururus This includes the viridis (Sminthurus viridis). (22) Phylum Nematoda. A non-exhaustive list of specific genera includes, but is not limited to, Aphelenchoides spp., Belonolaimus spp., Criconemella spp., Ditylenchus spp., Glomerulosus spp., and others. Globodera spp., Heterodera spp., Hirschmannii Hirschmanniella spp., Hoplolaimus spp., Meloidogyne spp., Pratylenchus spp., and La Radopholus spp. A non-exhaustive list of specific species includes Not specified, but Dirofilaria immitis, Globodera parvum Globodera pallida, Heterodera glycines, Heterodera zeae, Meloidogyne incognita, Meloidogyne javanica, Onchocerca volvulus, Pratylenchus penetrans, These include Radopholus similis, and Rotylenchulus reniformis. (23) Phylum Mollusca. A non-exhaustive list of specific species includes, but is not limited to, Arion vulgaris, Cornu aspersum, Deroceras reticulatum, Limax flavus, and Mirax . Milax gagates and Pomacea canaliculata Includes:

[0039] A particularly preferred group of pests to be controlled are sap-feeding pests.Sap-feeding pests generally have injection and / or sucking mouthparts and feed on plant sap and internal plant tissues.Examples of sap-feeding pests of particular concern in agriculture include, but are not limited to, aphids, leafhoppers, moths, scale insects, thrips, psyllids, mealybugs, stink bugs, and whiteflies.Specific examples of orders with sap-feeding pests of interest in agriculture include, but are not limited to, the orders Phthiraptera and Hemiptera. Specific examples of Hemiptera of interest in agriculture include, but are not limited to, Aulacaspis spp., Aphrophora spp., Aphis spp., Bemisia spp., Coccus spp., Euschistus spp., Lygus spp., Macrosiphum spp., Nezara spp., and Rhopalosiphum spp.

[0040] Another pest group that is particularly preferred for control is chewing pests. Chewing pests generally have mouthparts that allow chewing plant tissues, including roots, stems, leaves, shoots, and reproductive tissues (including but not limited to flowers, fruits, and seeds). Examples of chewing pests that are of particular concern in agriculture include, but are not limited to, caterpillars, beetles, grasshoppers, and locusts. Specific examples of the order that has chewing pests of interest in agriculture include, but are not limited to, Coleoptera and Lepidoptera. Specific examples of Coleoptera of interest in agriculture include, but are not limited to, Anthonomus spp., Cerotoma spp., Chaetocnema spp., Colaspis spp., Cyclocephala spp., Diabrotica spp., Hypera spp., Phyllophaga spp., and Phyllotreta spp. , Sphenophorus spp., and Sitophilus spp.

[0041] The phrase "pesticidally effective amount" means the amount of pesticide required to produce an observable effect on a pest (e.g., necrosis, death, suppression, prevention, elimination, destruction, or reduction in the occurrence and / or activity of a pest in an area). Effectiveness is achieved when pest populations are repelled from an area, when pests are incapacitated in or around an area, and / or when pests are eradicated in or around an area. Of course, a combination of these effects can occur. Typically, pest populations, activity, or both are desirably reduced by more than 50 percent, preferably by more than 90 percent, and most preferably by more than 99 percent. Generally, a pesticidal amount for agricultural purposes is about 1000 mg / hectare of pesticides per hectare. The average dosage is from about 0.0001 grams per hectare to about 5000 grams per hectare, preferably from about 0.0001 grams per hectare to about 500 grams per hectare, and even more preferably from about 0.0001 grams per hectare to about 500 grams per hectare. The average annual average annual yield is about 0.0001 grams per hectare to about 50 grams per hectare. DETAILED DESCRIPTION OF THE INVENTION

[0042] This document describes a molecule of formula 1 [ka] (In the formula, (A) R 1 is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl , (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, S(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, (C-C)alkyl-S(O)NH, and (C-C)haloalkyl-S(O)NH; (B) R 2is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl , (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, S(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, (C-C)alkyl-S(O)NH, and (C-C)haloalkyl-S(O)NH; (C) R 3 is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl , (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, S(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, (C-C)alkyl-S(O)NH, and (C-C)haloalkyl-S(O)NH; (D) R 4is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S selected from the group consisting of (O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2; (E) R 5 is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl, (C3-C6) halocycloalkenyl , (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, S(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, (C-C)alkyl-S(O)NH, and (C-C)haloalkyl-S(O)NH; (F) R 6 is selected from the group consisting of H and (C1-C6) alkyl; (G)R 7 is selected from the group consisting of H, F, Cl, Br, and I; (H) R 8 is selected from the group consisting of F, Cl, Br, and I; (I) R 9 is selected from the group consisting of H and (C1-C6) alkyl; (J) Q 1is selected from the group consisting of O and S; (K) Q 2 is selected from the group consisting of O and S; (L) R 10 is selected from the group consisting of H, (C-C)alkyl, (C-C)alkenyl, (C-C)haloalkyl, (C-C)alkyl(C-C)alkoxy, C(=O)(C-C)alkyl, and (C-C)alkoxyC(=O)(C-C)alkyl; (M) R 11 are H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl alkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl , (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2; (N)R 12 are H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl alkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl , (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2; (O) X 1 teeth, (1) N, (2) NO, and (3) CR 13 is selected from the group consisting of So, R 13 are H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6) alkyl, (C3-C6) silyl chloroalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl is selected from the group consisting of cycloalkenyl, (C-C)halocycloalkenyl, (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, S(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, (C-C)alkyl-S(O)NH, (C-C)haloalkyl-S(O)NH, and triazolyl; (P) X 2 teeth, (1) N, (2) NO, and (3) CR 14 is selected from the group consisting of So, R 14is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl , (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2; (Q) X 3 is N(R 15 ) (substituted or unsubstituted phenyl), N(R 15 ) (substituted or unsubstituted heterogeneous substituted or unsubstituted heterocyclyl; (a) Applicable R 15 is selected from the group consisting of H, (C-C)alkyl, (C-C)alkenyl, (C-C)alkynyl, (C-C)haloalkyl, (C-C)alkyl(C-C)alkoxy, C(=O)(C-C)alkyl, and (C-C)alkoxyC(=O)(C-C)alkyl; (b) the substituted phenyl and the substituted heterocyclyl are F, Cl, Br, I, H, CN, CHO, NHOH, NO, NO2, OH, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)alkylphenyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkoxy, (C1-C6)haloalkyl, (C1-C6)haloalkyl-S(O)2NH2, (C2-C6)alkenyl, (C2- C6)alkynyl, (C2-C6)haloalkenyl, (C3-C6)cycloalkenyl, (C3-C6)cycloalkyl, (C3-C6)halocycloalkenyl, (C3-C6)halocycloalkyl, (C1-C6)alkyl((C1-C6)alkyl)(=NO(C1-C6)alkyl), C(=NO(C1-C6)alkyl)(C1-C6)alkyl, C(O)(C1-C6)alkyl, C(O)NH(C1-C 6) Alkyl, C(O)NHphenyl, C(O)O(C1-C6)alkyl, CH(=NO(C1-C6)alkyl), imidazolyl, N((C1-C6)alkyl)(C(O)(C1-C6)alkyl), N((C1-C6)alkyl)(C(O)(C1-C6)alkyl-O(C1-C6)alkyl), N((C1-C6)alkyl)(C(O)(C1-C6)haloalkyl), N((C1-C6)alkyl) (C(O)O(C1-C6)alkyl), N((C1-C6)alkyl)2, N(C(O)O(C1-C6)alkyl)2, N=CH-phenyl, NH((C1-C6)alkylC(O)(C1-C6)alkyl), NH(C(O)(C1-C6)alkyl), NH(C(O)(C2-C6)alkenyl), NH(C(O)(C3-C6)cycloalkyl), NH(C1-C6)alkyl, NH(C1-C6)alkene nyl, NH(C1-C6)alkynyl, NH(C1-C6)alkylphenyl, NH(S(O)2(C1-C6)alkyl), NH2, NHC(O)(C1-C6)alkyl, NHC(O)(C1-C6)alkylphenyl, NHC(O)(C1-C6)alkylphenyl, NHC(O)(C1-C6)haloalkyl, NHC(O)(C2-C6)alkenyl, NH-C(O)O(C1-C6)alkenyl alkyl, oxazolyl, phenyl, pyrazolyl, pyridinyl, S(=NCN)((C1-C6)alkyl), S(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(=NCN)((C1-C6)alkyl), S(O)(C1-C6)alkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)alkyl, S(O)2(C1-C6)haloal having one or more substituents selected from the group consisting of alkyl, SCN, thiazolyl, thienyl, and triazolyl; Thus, each of the groups alkoxy, alkyl, haloalkoxy, haloalkyl, alkenyl, alkynyl, haloalkenyl, cycloalkenyl, cycloalkyl, halocycloalkenyl, halocycloalkyl, imidazolyl, phenyl, pyrazolyl, pyridinyl, thiazolyl, thienyl, and triazolyl is selected from the group consisting of F, Cl, Br, I, CN, OH, NH(C1-C6)alkyl, NH(C3-C6)cycloalkylCHO(C1-C6)alkyl, NH(C3-C6)cycloalkylCHO(C1-C6)haloa one selected from the group consisting of alkyl, NHCH2(C3-C6)cycloalkyl, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkyl, (C1-C6)alkoxy, and C(O)O-(C1-C6)alkyl; and N-oxides, agriculturally acceptable acid addition salts, salt derivatives, solvates, esters, etc. of the molecules of Formula 1 derivatives, crystalline polymorphs, isotopes, resolved stereoisomers, and tautomers. The molecules of formula 1 may exist in various geometric or optical isomeric forms, or in various tautomeric forms. One or more centers of chirality may be present, in which case the molecule of Formula 1 may exist as a pure enantiomer, a mixture of enantiomers, a pure diastereomer, or a mixture of diastereomers. Those skilled in the art will appreciate that one stereoisomer may be more active than another. It will be understood that individual stereoisomers may be obtained by known individual synthetic procedures, by conventional synthetic procedures using resolved starting materials, or by conventional resolution procedures. It is understood that compounds of Formula 1 may be obtained as single geometric isomers (cis or trans, E or Z). The molecule may have double bonds where it can exist as a cis or trans isomer, or as a mixture of geometric isomers (cis and trans, E and Z). Centers of tautomerism may also be present. The present disclosure covers all such isomers, tautomers, and mixtures thereof in all proportions.

[0043] In another embodiment, the carboxamide and phenyl bonded to the cyclopropane of the molecule of Formula 1 is in the R,R configuration. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments.

[0044] In another embodiment, R 1 is selected from the group consisting of H, F, or Cl. This embodiment is 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Other It may be used in combination with the embodiments.

[0045] In another embodiment, R 2 is selected from the group consisting of H, F, Cl, Br, CH3, and CF3. This embodiment is 1 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments.

[0046] In another embodiment, R 3 is selected from the group consisting of H, F, Cl, Br, CH3, CF3, and OCF3. This embodiment is 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments.

[0047] In another embodiment, R 4 is selected from the group consisting of H, F, Cl, Br, CH3, and CF3. This embodiment is 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments.

[0048] In another embodiment, R 5 is selected from the group consisting of H and Cl. This embodiment is 1 , R 2 , R 3 , R 4 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Other implementations of It may be used in combination with the above.

[0049] In another embodiment, R 6 is H. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of That's fine.

[0050] In another embodiment, R 7 is selected from the group consisting of Cl and Br. This embodiment is1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Other implementations of It may be used in combination with the above.

[0051] In another embodiment, R 8 is selected from the group consisting of Cl and Br. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Other implementations of It may be used in combination with the above.

[0052] In another embodiment, R 9 is H. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of That's fine.

[0053] In another embodiment, R 10 is H or CH3. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 In combination with other embodiments of may also be used.

[0054] In another embodiment, R 11 is selected from the group consisting of H, F, Cl, and CH3. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments.

[0055] In another embodiment, R 12 is selected from the group consisting of H and Cl. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R11 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments.

[0056] In another embodiment, Q 1 is O. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of That's fine.

[0057] In another embodiment, Q 2 is selected from the group consisting of O and S. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , X 1 , X 2 , and X 3 Other embodiments of may be used in combination with

[0058] In another embodiment, X 1 N, NO, and CR 13 This embodiment is selected from the group consisting of , R 1 , R 2 , R3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 2 , and X 3 Other This embodiment may be used in combination with the previous embodiment.

[0059] In another embodiment, R 13 is selected from the group consisting of H, F, Cl, Br, I, CN, CH3, CF3, OCH3, OCF3, SCH3, S(O)CH3, S(O)2CH3, and triazolyl. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 2 , and X 3 Other implementations of It may be used in combination with the above.

[0060] In another embodiment, X 2 N and CR 14 This embodiment is selected from the group consisting of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X1 , and X 3 It may be used in combination with other embodiments.

[0061] In another embodiment, R 14 is selected from the group consisting of H, F, Cl, and OCH3. The state is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , and X 3 Noso It may be used in combination with other embodiments.

[0062] In another embodiment, X 3 teeth, [ka] [ka] [ka] (In the formula, (a) R 15 is H, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) ha alkyl, (C1-C6) alkyl(C1-C6) alkoxy, C(=O)(C1-C6) alkyl, and (C1-C6) alkoxyC(=O)(C1-C6)alkyl; (b) X 4 teeth, (i) N, (ii) NO, and (iii) CR 16is selected from the group consisting of So, R 16 are H, F, Cl, Br, I, CN, NH2, NO2, CHO, (C1-C6) alkyl, (C3-C6) silyl chloroalkyl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl and (C-C)halocycloalkenyl, (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, S(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, S(O)(C-C)haloalkyl, CO(C-C)alkyl, CH(═NO(C-C)alkyl), C(═NO(C-C)alkyl)(C-C)alkyl, (C-C)alkyl-S(O)NH, and (C-C)haloalkyl-S(O)NH; Each of the alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, haloalkyl, halocycloalkyl, haloalkenyl, halocycloalkenyl, and haloalkoxy groups may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH, NO, oxo, (C-C)alkyl, (C-C)alkoxy, and C(O)O—(C-C)alkyl; (c) X 5 teeth, (i) N, (ii) NO, and (iii) CR 17 is selected from the group consisting of So, R 17 is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl , (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, C(O)O(C1-C6)alkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2; (d) X 6 teeth, (i) N, (ii) NO, and (iii) CR 18 is selected from the group consisting of So, R 18 is H, F, Cl, Br, I, CN, NO2, OH, NH2, SCN, CHO, (C1-C6) alkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) haloalkyl, (C1-C6) alkoxy, (C1-C6) haloalkoxy, NH(C1-C6) alkyl, N((C1-C6) alkyl)2, S(C1-C6) alkyl, S(O)(C1-C6) alkyl, S(O)2(C1-C6) alkyl, S(C1-C6) haloalkyl, S(O)(C1-C6) haloalkyl, S(O)2(C1-C6) haloalkyl, CO(C1-C6) alkyl, CONH(C1-C6)alkyl, NHCO(C1-C6)alkyl, N(C1-C6)alkyl-CO(C1-C6)alkyl, NHCO(C2-C6)alkenyl, NHCO(C3-C6)cycloalkyl, NHCO(C1-C6)haloalkyl, N(C1-C6)alkyl-CO(C1-C6)haloalkyl, NHCO(C1-C6)alkylphenyl, NH-C(O)O(C1-C6)alkyl, N(C1-C6)alkyl-C(O)O(C1-C6)alkyl, CH(=NO(C1-C6)alkyl), C(=NO(C1-C6)alkyl)(C1-C6)alkyl phenyl, pyrazolyl, imidazolyl, and triazolyl; Each of the alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, halocycloalkyl, cycloalkyl, phenyl, imidazolyl, and triazolyl groups may be optionally substituted with one or more substituents selected from the group consisting of F, Cl, Br, I, CN, OH, NH, NO, oxo, (C-C)alkyl, (C-C)alkoxy, and C(O)O—(C-C)alkyl; (e) X 7 teeth, (i) N, (ii) NO, and (iii) CR 19 is selected from the group consisting of So, R 19 is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl , (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, C(O)O(C1-C6)alkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2; (f) X 8 teeth, (i) N, (ii) NO, and (iii) CR 20 is selected from the group consisting of So, R 20is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkenyl, (C2-C6) alkynyl, (C1-C6) alkoxy, (C1-C6) haloalkyl, (C3-C6) halocycloalkyl, (C2-C6) haloalkenyl , (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, C(O)O(C1-C6)alkyl, (C1-C6)alkyl-S(O)2NH2, and (C1-C6)haloalkyl-S(O)2NH2; (g) R 21 is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl aryl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2; selected from the group consisting of phenyl, pyridinyl, and thienyl; Thus, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, phenyl, imidazolyl, and triazolyl groups are selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkoxy, and C(O)O-(C1-C6)alkyl. may be optionally substituted with one or more substituents selected from the group consisting of: (h) R 22 is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl aryl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2; selected from the group consisting of phenyl, pyridinyl, and thienyl; Thus, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, phenyl, imidazolyl, and triazolyl groups are selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkoxy, and C(O)O-(C1-C6)alkyl. may be optionally substituted with one or more substituents selected from the group consisting of: (i) R 23 is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl aryl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2; selected from the group consisting of phenyl, pyridinyl, and thienyl; Thus, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, phenyl, imidazolyl, and triazolyl groups are selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkoxy, and C(O)O-(C1-C6)alkyl. may be optionally substituted with one or more substituents selected from the group consisting of: (j) R 24 is H, F, Cl, Br, I, CN, NH2, NO2, (C1-C6) alkyl, (C3-C6) cycloalkyl aryl, (C2-C6)alkenyl, (C3-C6)cycloalkenyl, (C2-C6)alkynyl, (C1-C6)alkoxy, (C1-C6)haloalkyl, (C3-C6)halocycloalkyl, (C2-C6)haloalkenyl, (C3-C6)halocycloalkenyl, (C1-C6)haloalkoxy, S(C1-C6)alkyl, S(O)(C1-C6)alkyl, S(O)2(C1-C6)alkyl, S(C1-C6)haloalkyl, S(O)(C1-C6)haloalkyl, S(O)2(C1-C6)haloalkyl, (C1-C6)alkyl-S(O)2NH2, (C1-C6)haloalkyl-S(O)2NH2; selected from the group consisting of phenyl, pyridinyl, and thienyl; Thus, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, haloalkoxy, phenyl, imidazolyl, and triazolyl groups are selected from the group consisting of F, Cl, Br, I, CN, OH, NH2, NO2, oxo, (C1-C6)alkyl, (C1-C6)alkoxy, and C(O)O-(C1-C6)alkyl. and optionally substituted with one or more substituents selected from the group consisting of is selected from. This embodiment is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , and X 2 It may be used in combination with other embodiments.

[0063] In another embodiment, X 3 is selected from the group consisting of the following chemical formulas: [ka] This embodiment is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , and X 2 It may be used in combination with other embodiments.

[0064] In another embodiment, X 3 The substituted or unsubstituted heterocyclyl may be indolyl, oxazolyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, tetrazolyl, thiadiazolyl, thiazolyl, thienyl, triazinyl, [1,2,4]triazolo[1,5-c]pyrimidinyl, triazolyl, 2,3-dihydrophthalazine-1,4-dionyl, indolinyl, and and pyrimidine-2,4(1H,3H)-dionyl, wherein the substituents are selected from the group consisting of F, Cl, Br, I, H, CN, NH, NO, (C-C)alkoxy, (C-C)alkyl, (C-C)haloalkoxy, (C-C)haloalkyl, (C-C)haloalkenyl, (C-C)halocycloalkenyl, and (C-C)halocycloalkyl. This embodiment is further illustrated by the formula: 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , and X 2 Other embodiments and combinations of It may also be used.

[0065] In another embodiment, X 3 wherein the substituted or unsubstituted heterocyclyl is selected from the group consisting of indolinyl, oxazolyl, pyridyl, and thiadiazolyl, and the substituents are F, Cl, Br , I, H, CN, NO2, NH2, (C1-C6)alkoxy, (C1-C6)alkyl, (C1-C6)haloalkoxy , (C-C)haloalkyl, (C-C)haloalkenyl, (C-C)halocycloalkenyl, and (C-C)halocycloalkyl. This embodiment is further illustrated by the formula: R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , and X2 In combination with other embodiments of They may also be used in combination.

[0066] In another embodiment, X 3 is N(R 15 ) (substituted or unsubstituted phenyl), (a) Applicable R 15 is selected from the group consisting of H, and (C1-C6) alkyl; (b) The substituted phenyl is selected from the group consisting of F, Cl, Br, I, CN, NO, NH, (C-C)alkoxy, (C-C (C-C) alkyl, (C-C) haloalkoxy, (C-C) haloalkyl, (C-C) haloalkenyl, (C-C) cycloalkenyl, (C-C) cycloalkyl, (C-C) halocycloalkenyl, and (C-C) halocycloalkyl. The embodiment is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , and X 2 It may be used in combination with other embodiments. In another embodiment, R 15 is selected from the group consisting of H, CH, CHCH, CHCHCH, CHCH=CH, CH-C=CH, and CHCF. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11, R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of This may also be done.

[0067] In another embodiment, X 4 N and CR 16 This embodiment is selected from the group consisting of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments. In another embodiment, R 16 is selected from the group consisting of H, F, Cl, CN, NH, CH, CHCH, and CH(CH). 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments.

[0068] In another embodiment, X 5 N, NO, and CR 17 This embodiment is selected from the group consisting of , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Noso It may be used in combination with other embodiments.

[0069] In another embodiment, R 17 is selected from the group consisting of H, F, Cl, and CN, NH. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments.

[0070] In another embodiment, X 6 N, NO, and CR 18 This embodiment is selected from the group consisting of , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q2 , X 1 , X 2 , and X 3 Noso It may be used in combination with other embodiments.

[0071] In another embodiment, R 18 are H, F, Cl, CN, NO2, NH 2、 CH3, CF3, OCH3, OCHCF2, OCF3 , SCH3, S(O)CH3, S(O)2CH3, C(O)NHCH3, and NHC(O)CH3. The embodiment of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 It may be used in combination with other embodiments.

[0072] In another embodiment, X 7 is CR 19 This embodiment is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of It's okay to stay there.

[0073] In another embodiment, R 19 is selected from the group consisting of H, F, and NH. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Nosono It may be used in combination with other embodiments.

[0074] In another embodiment, X 8 is CR 20 This embodiment is R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of It's okay to stay there.

[0075] In another embodiment, R 20 is selected from the group consisting of H, F, Cl, and CH. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10, R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 of It may be used in combination with other embodiments.

[0076] In another embodiment, R 21 is H. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of It may be possible.

[0077] In another embodiment, R 22 is H. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of It may be possible.

[0078] In another embodiment, R 23 is H. This embodiment is 1 , R 2 , R3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of It may be possible.

[0079] In another embodiment, R 24 is H. This embodiment is 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , Q 1 , Q 2 , X 1 , X 2 , and X 3 Used in combination with other embodiments of It may be possible.

[0080] In another embodiment, (A) R 1 , R 2 , R 3 , R 4 , R 5 , R 11 , and R 12 are each independently selected from the group consisting of H, F, Cl, Br, (C-C)alkyl, (C-C)haloalkyl, and (C-C)haloalkoxy; (B) R 6 and R 9 is H; (C) R 7 is selected from the group consisting of Cl and Br; (D) R8 is selected from the group consisting of Cl and Br; (E) Q 1 and Q 2 are each independently selected from the group consisting of O and S; (F) R 10 is H; (G) X 1 teeth, (1) N, (2) NO, and (3) CR 13 is selected from the group consisting of So, R 13 is selected from the group consisting of H, F, Cl, Br, I, CN, (C-C)alkyl, (C-C)alkoxy, (C-C)haloalkyl, (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, and triazolyl; (H) X 2 teeth, (1) N and (2) CR 14 is selected from the group consisting of So, R 14 is selected from the group consisting of H, F, Cl, and (C1-C6)alkoxy; (I) X 3 teeth, [ka] (In the formula, (a) R 15 is selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl; (b) X 4 teeth, (i) N, and (ii) CR 16 is selected from the group consisting of So, R 16 are H, F, Cl, CN, and NH 2、 and (C1-C6) alkyl; (c) X 5 teeth, (i) N, (ii) NO, and (iii) CR 17 is selected from the group consisting of So, R 17 are H, F, Cl, NH 2、 and CN; (d) X 6 teeth, (i) N, (ii) NO, and (iii) CR 18 is selected from the group consisting of So, R 18 are H, F, Cl, CN, NO2, NH 2、 selected from the group consisting of (C-C)alkyl, (C-C)haloalkyl, (C-C)alkoxy, (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, CONH(C-C)alkyl, and NHCO(C-C)alkyl; (e) X 7 is CR 19 and So, R 19 is H, NH 2、 and F; (f) X 8 is CR 20 and So, R 20 are H, F, Cl, NH 2、 and (C1-C6) alkyl; and (g) R 21 , R 22 , R 23 , and R 24 is H). In another embodiment, (A) R 1 is H; (B) R 2 is selected from the group consisting of H, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl; (C) R 3 is selected from the group consisting of H, F, Cl, Br, (C-C) alkyl, (C-C) haloalkyl, and (C-C) haloalkoxy; (D) R 4 is selected from the group consisting of H, Cl, Br, (C1-C6)alkyl, and (C1-C6)haloalkyl; (E) R 5 is selected from the group consisting of H and Cl; (F) R 6 is H; (G)R 7 is selected from the group consisting of Cl and Br; (H) R 8 is selected from the group consisting of Cl and Br; (I) R 9 is H; (J) Q 1 is O; (K) Q 2 is selected from the group consisting of O and S; (L) R 10 is H; (M) R 11 is selected from the group consisting of H, F, Cl, and (C1-C6) alkyl; (N)R 12 is selected from the group consisting of H and Cl; (O) X 1 teeth, (1) N, (2) NO, and (3) CR 13 is selected from the group consisting of So, R 13 is selected from the group consisting of H, F, Cl, Br, I, CN, (C-C)alkyl, (C-C)alkoxy, (C-C)haloalkyl, (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, and triazolyl; (P) X 2 teeth, (1) N and (2) CR 14is selected from the group consisting of So, R 14 is selected from the group consisting of H, F, Cl, and (C1-C6)alkoxy; and (Q) X 3 teeth, [ka] (In the formula, (a) R 15 is selected from the group consisting of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl; (b) X 4 teeth, (i) N, and (ii) CR 16 is selected from the group consisting of So, R 16 are H, F, Cl, CN, and NH 2、 and (C1-C6) alkyl; (c) X 5 teeth, (i) N, (ii) NO, and (iii) CR 17 is selected from the group consisting of So, R 17 are H, F, Cl, NH 2、 and CN; (d) X 6 teeth, (i) N, (ii) NO, and (iii) CR 18 is selected from the group consisting of So, R 18 is selected from the group consisting of H, F, Cl, CN, NO, NH, (C-C)alkyl, (C-C)haloalkyl, (C-C)alkoxy, (C-C)haloalkoxy, S(C-C)alkyl, S(O)(C-C)alkyl, S(O)(C-C)alkyl, CONH(C-C)alkyl, and NHCO(C-C)alkyl; (e) X 7 is CR19 and So, R 19 is H, NH 2、 and F; (f) X 8 is CR 20 and So, R 20 are H, F, Cl, NH 2、 and (C1-C6) alkyl; and (g) R 21 , R 22 , R 23 , and R 24 is H). In another embodiment, (A) R 1 is selected from the group consisting of H, F, or Cl; (B) R 2 is the group consisting of H, F, Cl, Br, (C1-C6) alkyl, and (C1-C6) haloalkyl Selected from; (C) R 3 is selected from the group consisting of H, F, Cl, Br, (C-C) alkyl, (C-C) haloalkyl, and (C-C) haloalkoxy; (D) R 4 is the group consisting of H, F, Cl, Br, (C1-C6) alkyl, and (C1-C6) haloalkyl Selected from; (E) R 5 is selected from the group consisting of H, F, and Cl; (F) R 6 is H; (G)R 7 is selected from the group consisting of Cl and Br; (H) R 8 is selected from the group consisting of Cl and Br; (I) R 9 is H; (J) Q 1 is O; (K) Q 2is selected from the group consisting of O and S; (L) R 10 is H; (M) R 11 is selected from the group consisting of H, F, Cl, and (C1-C6) alkyl; (N)R 12 is selected from the group consisting of H and Cl; (O) X 1 is CR 13 and So, R 13 is selected from the group consisting of H, F, Cl, Br, I, CN, (C-C)alkyl, (C-C)alkoxy, (C-C)haloalkyl, and (C-C)haloalkoxy; (P) X 2 is CR 14 and So, R 14 is selected from the group consisting of H, F, Cl, and (C-C) alkyl, (C-C) alkoxy, (C-C) haloalkyl, and (C-C) haloalkoxy; and (Q) X 3 teeth, [ka] (In the formula, R 15 consists of H, (C1-C6) alkyl, (C2-C6) alkenyl, and (C1-C6) haloalkyl Selected from the group; X 4 is CR 16 and so, R 16 are H, F, Cl, NH 2、 selected from the group consisting of CN, NO, (C-C) alkyl, (C-C) haloalkyl, (C-C) alkoxy, and (C-C) haloalkoxy; Re; X 5 is CR 17 and so, R 17 are H, F, Cl, NH 2、selected from the group consisting of CN, NO, (C-C) alkyl, (C-C) haloalkyl, (C-C) alkoxy, and (C-C) haloalkoxy; Re; X 6 is CR 18 and so, R 18 are H, F, Cl, NH 2、 selected from the group consisting of CN, NO, (C-C) alkyl, (C-C) haloalkyl, (C-C) alkoxy, and (C-C) haloalkoxy; Re; X 7 is CR 19 and so, R 19 are H, F, Cl, NH 2、 selected from the group consisting of CN, NO, (C-C) alkyl, (C-C) haloalkyl, (C-C) alkoxy, and (C-C) haloalkoxy; Re; X 8 is CR 20 and so, R 20 are H, F, Cl, CN, and NH 2、 NO2, (C1-C6) alkyl, (C1-C6 ) haloalkyl, (C1-C6) alkoxy, and (C1-C6) haloalkoxy; (It can be).

[0081] Preparation of cyclopropyl carboxylic acids Stilbenes 1-1 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 as disclosed above) is treated with a base such as sodium hydroxide in the presence of a carbene source such as chloroform or bromoform and a phase transfer catalyst such as N-benzyl-N,N-diethylethanaminium chloride in a polar protic solvent such as water at a temperature of about 0°C to about 40°C to give diarylcyclopropane. Ropan 1-2 (R1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 is as disclosed above ) can be obtained (Scheme 1, Step a). Diarylcyclopropanes 1-2 can be obtained by Treatment with a transition metal such as ruthenium(III) chloride in the presence of a stoichiometric oxidizing agent such as sodium periodate in a solvent mixture (preferably water, ethyl acetate, and acetonitrile) at a temperature between about 0°C and about 40°C provides cyclopropyl carboxylic acids 1-3 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 as disclosed above) can be obtained (Scheme 1, step b).

[0082] Scheme 1 [ka]

[0083] Thiophene carbonyl 1.4-1(R 9 as disclosed above) with sodium methoxide. In the presence of a base such as methyl phosphate, in a polar aprotic solvent such as N,N-dimethylformamide, at a temperature of about -10°C to about 80°C, alkoxybenzylphosphonate 2-2 (R 1 , R 2 , R 4 , R 5 is as disclosed above) to give stilbene 1.4-2 (R 1 , R 2 , R 4 , R 5 , R 6 , and R 9(as disclosed above) can be obtained (Scheme 1.4, step a). Chillben 1.4-2(R 1 , R 2 , R 4 , R 5 , R 6 , and R 9 as disclosed above) A carbene source such as chloroform or bromoform and N-benzyl-N,N-diethylethanamine In the presence of a phase transfer catalyst such as ammonium chloride, in a polar protic solvent such as water, at about 0°C Treatment with a base such as sodium hydroxide at a temperature of about 40°C to afford thiophenecyclopropane 1,4-3(R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 (as disclosed above) can be obtained (Scheme 1.4, step b). Thiophenecyclopropane 1.4-3 can be prepared by the addition of periodate. In the presence of a stoichiometric oxidizing agent such as sodium, a solvent mixture (preferably water, ethyl acetate) and acetonitrile) at a temperature of about 0°C to about 40°C with a transition metal such as ruthenium(III) chloride to give cyclopropyl carboxylic acid 1-3 (R 3 is a (C1-C4)alkoxy group, and R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 as disclosed above) can be obtained (Scheme 1.4, step c).

[0084] Scheme 1.4 [ka]

[0085] Phenylcarbonyls 1.7-1(R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 As disclosed above, ) in the presence of a base such as sodium hydride in a polar aprotic solvent such as tetrahydrofuran at a temperature of about −10° C. to about 40° C. to give stilbenes 1.7-3 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 is as disclosed above) Stilbenes 1.7-3 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 (as disclosed above) in a polar aprotic solvent such as toluene. Diisobutylaluminum hydride (DIBAL) and other reducing agents are used in a solvent at temperatures between about -80°C and about 0°C. Treated with the original agent, alcohol 1.7-4 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 is disclosed above (Scheme 1.7, step b) Alcohols 1.7-4 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 (as disclosed above) in a polar aprotic solvent such as diethyl ether in the presence of an acid catalyst such as p-toluenesulfonic acid. and protecting the stilbenes 1,7-5 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 is as disclosed above) (Scheme 1.7, step c). Protected stilbenes 1.7-5 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 as disclosed above) in chloroform or bromoform Carbene sources such as methyl ether and phase transfer compounds such as N-benzyl-N,N-diethylethanaminium chloride In the presence of a catalytic catalyst, sodium hydroxide is produced in a polar protic solvent such as water at a temperature of about 0°C to about 40°C. Treatment with a base such as thorium affords the cyclopropanes 1,7-7(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 (as disclosed above) can be obtained (Scheme 1.7, Step Top d). Cyclopropanes 1,7-6 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 as disclosed above) in a polar protic solvent such as methanol at a temperature of about 0°C to about 40°C. At room temperature, treatment with an acid such as p-toluenesulfonic acid affords the alcohol 1.7-7(R 1 , R2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 (as disclosed above) can be obtained ( Room 1.7, step e). Alcohols 1.7-7 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 (as disclosed above) in a polar aprotic solvent such as acetone at about -10°C. Treatment with an oxidizing agent such as Jones reagent at a temperature of about 40°C to give cyclopropyl carboxylic acids 1-3 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 As disclosed above, ) is obtained (Scheme 1.7, step f).

[0086] Scheme 1.7 [ka]

[0087] Preparation of stilbenes Stilbenes 1-1 can be prepared by several different methods outlined in Scheme 2. Phenylcarbonyls 2-1 (R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 is as disclosed above) In the presence of a base such as sodium methoxide, the stilbenes 1-1 can be obtained by treating the stilbenes 1-2 with alkoxybenzylphosphonates 2-2 in a polar aprotic solvent such as N,N-dimethylformamide at a temperature of about -10°C to about 30°C, followed by heating to 40°C to about 80°C (Ski). Program 2, step a).

[0088] Scheme 2 [ka]

[0089] Aryl halides 2-3(R 1 , R 2 , R 3 , R 4 , and R 5 as disclosed above) The reaction is carried out with a transition metal catalyst such as palladium(II) acetate and 1,1'-bis(diphenylphosphino)ferro In the presence of a bisphosphine ligand such as benzophenone, vinylbenzenes 2-4 (R 6 and R 9 as disclosed above) to give stilbenes 1-1 (Scheme 2, step b). In the method, aryl halides 2-3 are reacted with tetrakis(triphenylphosphine) para In the presence of a transition metal catalyst such as sodium(0) and a base such as potassium carbonate, 1,2-dimethoxyethane In a solvent mixture such as methanol and water, vinyl boronates 2-5 (R 6 and R 9 as disclosed above) to give stilbenes 1-1. (Scheme 2, step c).

[0090] In yet another embodiment, stilbenes 1-1 can also be prepared by the Wittig olefination method (Chalal, M.; Vervandier-Fasseur, D.; Meunier, P.; Cattey, H.; Hierso, J.-C. Tetrahedron 2012, 68, 3899-3907) outlined in Scheme 2.5. Phenylcarbonyls 2-1 (R 1 , R 2 , R 3 , R 4 , and R 5 is as disclosed above, and R 6 is H) can be treated with alkoxybenzyltriphenylphosphonium chlorides 2.5-2 in the presence of a base such as n-butyllithium in a polar aprotic solvent such as tetrahydrofuran at about −78 °C to ambient temperature to give stilbenes 1-1 (Scheme 2.5, step a).

[0091] Scheme 2.5 [ka]

[0092] Preparation of cyclopropylamides Cyclopropylamides 3-3(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , X 1 , X 2 , and Q 2 is as disclosed above, and X 3 is as disclosed above and is OH) can be reacted with amines or amine salts 3-2 (R10 , R 11 , R 12 , X 1 , X 2 , Q 2 , and X 3 are as disclosed above) and activated carboxylic acids 3-1 (A is an activating group and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 (as disclosed above) with a base such as triethylamine, diisopropylethylamine, 4-methylmorpholine, 4-dimethylaminopyridine, or pyridine (Scheme 3, step a).

[0093] The activated carboxylic acids 3-1 can be prepared by activating an acid halide such as an acid chloride, an acid bromide, or an acid fluoride. para-nitrophenyl ester, pentafluorophenyl ester, ethyl (hydrogen (roxyiminio)cyanoacetate ester, methyl ester, ethyl ester, benzyl ester, N-hydroxysuccinimidyl ester, hydroxybenzotriazol-1-yl esters or carboxylic acids such as hydroxypyridyltriazol-1-yl esters The acid chlorides may be esters; O-acylisoureas; acid anhydrides; or thioesters. Acid chlorides can be prepared from the corresponding carboxylic acids by treatment with dehydrating chlorination reagents such as oxalyl chloride or thionyl chloride. The activated carboxylic acid esters 3-1 can be prepared in situ by the addition of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxygen. Activated carboxylic acid esters 3-1 can also be prepared in situ from carboxylic acids using uronium salts such as benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (HATU), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU), or (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (COMU). Alternatively, activated carboxylic acid esters 3-1 can be prepared in situ from phosphonium salts such as benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (PyBop). Furthermore, activated carboxylic acid esters 3-1 can be prepared from carboxylic acids using ammonium salts. was synthesized in situ in the presence or absence of triazoles such as hydroxybenzotriazole monohydrate (HOBt) or 1-hydroxy-7-azabenzotriazole (HOAt) by the addition of 1-(3- Prepared from carboxylic acids using coupling reagents such as (dimethylaminopropyl)-3-ethylcarbodiimide, propylphosphonic anhydride, or dicyclohexylcarbodiimide O-acylisourea can be prepared by the method of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide. Alternatively, activated carboxylic acid esters 3-1 can be prepared in situ using dehydrating carbodiimides such as 1-hydroxy-7-azabenzo[a]imide or dicyclohexylcarbodiimide. In the presence of a triazole such as 2-chloro-1,3-dimethylimidazoline (HOAt), Coupling reagents such as cinnamium hexafluorophosphate (CIP) can be used to prepare carboxylic acids. It can be prepared from acids.

[0094] The sulfide-containing cyclopropylamides 3-3 were reacted with polar non-protonated amines such as dichloromethane. Treatment with about 1 equivalent of meta-chloroperbenzoic acid (sulfoxide) or about 2 equivalents of meta-chloroperbenzoic acid (sulfone) in an aqueous solvent at a temperature of about 0°C to about 40°C affords the corresponding Alternatively, sulfide-containing cyclopropylamides 3-3 can be oxidized to the corresponding sulfoxides or sulfones by treatment with 1 equivalent of sodium perborate (sulfoxide) or 2 equivalents of sodium perborate (sulfone) in a protic solvent such as acetic acid. The oxidation can be carried out at a temperature of about 40°C to about 100°C. The reaction is carried out at 50°C with approximately 1.5 equivalents of sodium perborate and is chromatographically separable. A mixture of sulfoxide cyclopropylamides and sulfone cyclopropylamides 3-3 can be obtained. Alternatively, the sulfide-containing cyclopropylamides 3-3 can be oxidized to the corresponding sulfilimines by treatment with about 1 equivalent of an amine such as cyanamide, about 1 equivalent of a base such as potassium tert-butoxide, and 1 to 2 equivalents of an oxidizing agent such as N-bromosuccinimide in a polar protic solvent such as methanol at a temperature of about 0°C to about 40°C. The sulfilimines can be oxidized to the corresponding sulfilimines by treatment with about 1 equivalent of an amine such as cyanamide, about 1 equivalent of a base such as potassium tert-butoxide, and 1 to 2 equivalents of an oxidizing agent such as N-bromosuccinimide in a solvent such as 2:1:1 ethanol:dichloromethane:water. It can be further oxidized to the corresponding sulfoximine by treatment with about 1 equivalent of meta-chloroperbenzoic acid and about 2 equivalents of potassium carbonate in a mixture at a temperature of about 0°C to about 40°C.

[0095] Cyclopropylamides 3-3(X 1 , X 2 , X 4 , X 5 , X 6 , X 7 , or X 8 is N) is reacted with about 1 equivalent of meta- It can be oxidized to the corresponding N-oxide by treatment with chloroperbenzoic acid.

[0096] Cyclopropylamides 3-3(R 3is NO2) can be reduced to the corresponding NH2 by treatment with an acid source, such as ammonium chloride, and iron in a polar protic solvent, such as methanol, water, or a mixture thereof, at a temperature of about 20°C to about 60°C.

[0097] Amines or amine salts 3-2(Q 2 is O) in an aprotic solvent selected from tetrahydrofuran, dichloromethane, chloroform, toluene, or pyridine at a temperature of about 40° C. to about 120° C. with or without an additive such as 1,1,1,3,3,3-hexamethyldisoloxane, or a sulfur compound such as phosphorus pentasulfide or 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (Lawson's reagent). Direct treatment with a source of amines or amine salts 3-2(Q 2 is S).

[0098] Scheme 3 [ka]

[0099] Cyclopropylamides 4-3(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , and X 3 is as disclosed above) can be reacted with amines or amine salts 4-2 (X) in an anhydrous aprotic solvent such as dichloromethane, tetrahydrofuran, 1,2-dichloroethane, dimethylformamide, or any combination thereof at a temperature of about 0° C. to about 120° C. 3as disclosed above) and activated carboxylic acids 4-1 (A is an activating group , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , and X 2 is disclosed above (as shown) with a base such as triethylamine, diisopropylethylamine, 4-methylmorpholine, 4-dimethylaminopyridine, or pyridine (Scheme 4, step a).

[0100] The activated carboxylic acids 4-1 can be prepared by activating an acid halide such as an acid chloride, an acid bromide, or an acid fluoride. p-Nitrophenyl ester, pentafluorophenyl ester, ethyl (hydroxyimino)cyanoacetate ester, methyl ester, ethyl ester, benzyl ester, N-hydroxysuccinimidyl ester, hydroxybenzotriazol-1-yl ester carboxylic acid esters such as hydroxypyridyltriazol-1-yl esters The acid chlorides can be prepared from the corresponding carboxylic acids by treatment with a dehydrating chlorination reagent such as oxalyl chloride or thionyl chloride. The activated carboxylic acid esters 4-1 can be prepared in situ by the addition of 1-[bis(2-methyl-2-methyl-4-phenyl)-2-propanol]. [(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU), or (1-cyano-2-ethoxy-2- Oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluoro Alternatively, activated carboxylic acid esters 4-1 can be prepared in situ from carboxylic acids using uronium salts such as benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (COMU). Furthermore, activated carboxylic acid esters 4-1 can be prepared in situ using hydroxybenzotriazole monohydrate (HOBt) or 1-hydroxy-7-azabicyclo[4.1.0]azabicyclo[4.1.1]azabicyclo[4.1.2 ... 1-(3-dimethyl-2-benzotriazole) in the presence or absence of a triazole, such as benzotriazole (HOAt). O-acylisoureas can be prepared from carboxylic acids using coupling reagents such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, propylphosphonic anhydride, or dicyclohexylcarbodiimide. O-acylisoureas can be prepared from carboxylic acids using coupling reagents such as 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide or Alternatively, activated carboxylic acid esters 4-1 can be prepared in situ using 1-hydroxy-7-azabenzotriazole. In the presence of a triazole such as 2-chloro-1,3-dimethylimidazolidinium Coupling reagents such as hexafluorophosphate (CIP) can be used to convert carboxylic acids to It can be prepared from

[0101] Scheme 4 [ka]

[0102] Cyclopropylamides 5-2(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8, R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , Q 2 , R 15 , X 4 , X 5 , X 6 , X 7 , and X 8 (as disclosed above) is Class 5-1(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , Q 2 , R 15 , X 4 , X 5 , X 6 , X 7 , and X 8 (as disclosed above) in the presence of an aprotic amine base such as pyridine in a solvent such as 1,4-dioxane at a temperature of about 110° C. It can be prepared by treatment with a methylating agent such as methylisothiazolinone and a copper catalyst such as copper diacetate (Scheme 5, step a).

[0103] Cyclopropylamides 5-4(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X2 , Q 2 , R 15 , X 4 , X 5 , X 6 , X 7 , and X 8 is as disclosed above, and L is (C-C)alkyl, (C-C)alkenyl, (C-C)cycloalkyl, (C-C)haloalkyl, (C-C)alkylphenyl, and (C-C)alkoxy, where each of the alkyl, alkenyl, cycloalkyl, haloalkyl, and phenyl groups can be optionally substituted with one or more substituents selected from F, Cl, Br, I, CN, OH, NH, NO, oxo, (C-C)alkyl, (C-C)alkoxy, and C(O)O(C-C)alkyl), can be optionally substituted with one or more substituents selected from F, Cl, Br, I, CN, OH, NH, NO, oxo, (C-C)alkyl, (C-C)alkoxy, and C(O)O(C-C)alkyl, in combination with amines 5-1 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , Q 2 , R 15 , X 4 , X 5 , X 6 , X 7 , and X 8 are as disclosed above), or amines 5-2 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , Q 2 , R 15 , X4 , X 5 , X 6 , X 7 , and X 8 as disclosed above) and activated carboxylic acids 5-3 (A is an activating group and L is as disclosed above). (which is the case with dichloromethane, tetrahydrofuran, 1,2-dichloroethane, N,N-dimethyl They can be prepared by treatment with a base such as triethylamine, diisopropylethylamine, 4-methylmorpholine, 4-dimethylaminopyridine, or pyridine in an anhydrous aprotic solvent such as ethylformamide, or any combination thereof at a temperature between about 0° C. and about 120° C. (Scheme 5, steps b and c).

[0104] The activated carboxylic acids 5-3 can be prepared by converting them into acid halides such as acid chlorides, acid bromides, or acid fluorides. p-Nitrophenyl ester, pentafluorophenyl ester, ethyl (hydroxyiminio)cyanoacetate ester, methyl ester, ethyl ester, benzyl ester, N-hydroxysuccinimidyl ester, hydroxybenzotriazol-1-yl ester carboxylic acid esters such as hydroxypyridyltriazol-1-yl esters The acid chlorides can be prepared from the corresponding carboxylic acids by treatment with a dehydrochlorinating agent such as oxalyl chloride or thionyl chloride. The activated carboxylic acid esters 5-3 can be prepared in situ by the addition of 1-[bis(2-methyl-2-methyl-1,2-diol)-2-( ... [(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU), O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU), or (1-cyano-2-ethoxy-2- Oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluoro Alternatively, activated carboxylic acid esters 5-3 can be prepared in situ from carboxylic acids using uronium salts such as benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate (COMU). Furthermore, activated carboxylic acid esters 5-3 can be prepared in situ using hydroxybenzotriazole monohydrate (HOBt) or 1-hydroxy-7-azabicyclo[4.2.1] ... In the presence of a triazole such as benzotriazole (HOAt), 1-(3-dimethylaminopropyl) O-acylisoureas can be prepared from carboxylic acids using coupling reagents such as 1-(3-dimethyl-2-methyl-1, ... Alternatively, activated carboxylic acid esters 5-3 can be prepared in situ using 2-chloro-1,3-dimethylimidazolidinium hexafluorophosphate in the presence of a triazolol such as 1-hydroxy-7-azabenzotriazole (HOAt). It can be prepared from carboxylic acids using coupling reagents such as cyclohexyl phosphate (CIP). The reactive carboxylic esters 5-3 can be prepared in situ from carboxylic acids using a coupling reagent such as 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (T3P®) in the presence of a base such as pyridine.

[0105] Scheme 5 [ka]

[0106] Cyclopropylamides 6-3(R 1 , R 2 , R 3 , R 4, R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , Q 2 , R 15 , X 5 , X 6 , X 7 , and X 8 (as disclosed above) is an aldehyde Hydride or ketone 6-1(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , Q 2 , R 15 , X 5 , X 6 , X 7 , and X 8 as disclosed above) and hydroxy and dimethylamines 6-2 (each alkyl group may be optionally substituted with one or more substituents selected from F, Cl, Br, I, CN, OH, NH, NO, oxo, (C-C) alkyl, (C-C) alkoxy, and C(O)O(C-C) alkyl) in a polar aprotic solvent such as ethanol at about 0°C. C. to about 80.degree. C. with or without an acid such as acetic acid (Scheme 6, step a).

[0107] Scheme 6 [ka]

[0108] Cyclopropylamides 7-3(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , Q 2 , R 15 , X 4 , X 5 , X 7 , and X 8 (as disclosed above) is an aldehyde Hydride or ketone 7-1(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , Q 2 , R 15 , X 4 , X 5 , X 7 , and X 8 as disclosed above) and hydroxy and amines 7-2 (each alkyl group may be optionally substituted with one or more substituents selected from F, Cl, Br, I, CN, OH, NH, NO, oxo, (C-C) alkyl, (C-C) alkoxy, and C(O)O(C-C) alkyl) in a polar aprotic solvent such as ethanol at about 0°C. It can be prepared by treatment with or without an acid such as acetic acid at temperatures between about 10° C. and about 80° C. (Scheme 7, step a).

[0109] Scheme 7 [ka]

[0110] Cyclopropylamides 8-3(R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , X 3 , and Q 2 is as disclosed above) is reacted with aryl bromide 8-1 (R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , X 3 , and Q 2 As disclosed above, and (C1-C6) alkenylstannane or (C1-C6) alkynylstannane 8-2( Each of the alkenyl or alkynyl groups may contain one or more substituents selected from F and SiMe3. (which may be optionally substituted with bis(triphenylphosphine)palladium(II) dichloride, etc.) in an aprotic solvent such as 1,4-dioxane at a temperature of about 20° C. to about 120° C. It can be prepared by treatment with a palladium source (Scheme 8, step a).

[0111] Cyclopropylamides 8-3 (wherein (C1-C6) alkynyl is trimethylsilyl alkyne) are heated in a polar solvent such as dichloromethane, methanol, or a combination thereof at about 0°C. Treatment with a fluoride source such as potassium fluoride at temperatures between about 10° C. and about 50° C. can provide cyclopropylamide 8-3 (wherein (C1-C6)alkynyl is CCH).

[0112] Scheme 8 [ka]

[0113] Cyclopropylamides 9-3(R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , X 3 , and Q 2 is as disclosed above) is reacted with aryl bromide 9-1 (R 1 , R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , X 3 , and Q 2 as disclosed above), and (C1-C6) alkenylstannane or (C1-C6 alkynylstannane) (each of the alkenyl or alkynyl groups may have one or more substituents selected from F and SiMe3). and a palladium(II) dichloride, such as bis(triphenylphosphine)palladium(II) dichloride, in an aprotic solvent, such as 1,4-dioxane, at a temperature of about 20° C. to about 120° C. It can be prepared by treatment with a radium source (Scheme 9, step a).

[0114] Cyclopropylamides 9-3 (wherein (C1-C6) alkynyl is trimethylsilyl alkyne) are heated in a polar solvent such as dichloromethane, methanol, or a combination thereof at about 0°C. Treatment with a fluoride source such as potassium fluoride at temperatures between about 10° C. and about 50° C. can provide cyclopropylamide 9-3 (wherein (C1-C6)alkynyl is CCH).

[0115] Scheme 9 [ka]

[0116] Cyclopropylamides 10-3(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , X 4 , X 5 , X 6 , X 7 , and X 8 are as disclosed above) can be converted to primary amides 10-1 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R10 , R 11 , R 12 , X 1 , and X 2 As mentioned above, as shown) and aryl bromides 10-2 (X 4 , X 5 , X 6 , X 7 , and X 8 (as disclosed above) with a palladium catalyst such as tris(dibenzylideneacetone)dipalladium(0), a phosphine ligand such as 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene, and an inorganic base such as cesium carbonate in an aprotic solvent such as 1,4-dioxane at a temperature of about 60° C. to about 80° C. (Scheme 10, step a).

[0117] Scheme 10 [ka]

[0118] Cyclopropylamides 11-3(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , X 4 , X 5 , X 6 , X 7 , and X 8 as disclosed above) is 11-1 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , X 4 , X 5 , X 6 , X 7 , and X 8 (as disclosed above) can be prepared by treating a metal such as palladium on carbon in a solvent such as ethyl acetate in the presence of a reducing agent such as hydrogen gas, or a metal such as iron in a solvent mixture such as methanol and water in the presence of a reducing agent such as ammonium chloride at a temperature between about 25°C and about 60°C (Scheme 11, step a). Pyramides 11-3(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , X 4 , X 5 , X 6 , X 7 , and X 8 As disclosed above, 11-2 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , X 4 , X 5 , X 6 , X 7 , and X8 is disclosed above (as shown) can be prepared by treatment with anhydrous acidic solution such as hydrochloric acid in 1,4-dioxane and dichloromethane at a temperature of about 25° C. (Scheme 11, step b).

[0119] Scheme 11 [ka]

[0120] Cyclopropylamides 12-3(R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X 2 , Q 2 , R 15 , X 4 , X 5 , X 6 , X 7 , and X 8 is as disclosed above, and L 2 is a (C1-C6) alkenyl group or a (C1-C6) alkynyl group, and the each optionally substituted with one or more substituents selected from F, Cl, and (C1-C6) alkyl. aryl halides 12-1 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , Q 1 , R 10 , R 11 , R 12 , X 1 , X2 , Q 2 , R 15 , X 4 , X 5 , X 6 , X 7 , and X 8 (as disclosed above) with a stannane (L) such as 12-2 in the presence of a metal catalyst such as bis(triphenylphosphine)palladium(II) dichloride in an aprotic solvent such as 1,4-dioxane at a temperature of about 90° C. 2 as disclosed above) (Scheme 12, step a).

[0121] Scheme 12 [ka]

[0122] In some embodiments, 1-3 is an α,β-unsaturated aldehyde 13-1 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 9 (as described above). Those skilled in the art will appreciate that compound 13-1 can be synthesized by aldol condensation of commercially available appropriately substituted aldehydes and acetaldehyde (see Yoshikawa, M.; Kamei, T. PCT Int. Appl. 2010123006, 2010). 13-1 can be converted to acetaldehyde by the aldol condensation of (C1-C6) alkyl orthoformate in the presence of hydrobromic acid, N-bromosuccinimide, hydrochloric acid, N-chlorosuccinimide, and an acid with a pH of 0-5, such as pyridinium p-toluenesulfonate (PPTS), in a (C1-C6) alkanol solvent at temperatures between 0°C and ambient pressure. By treating with acetal 13-2 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R9 is as disclosed above, and R a is (C1-C6) alkyl, or R a and R a Together, these form cyclic acetone Acetal 13-2 can be prepared by reacting sodium hydroxide with acetal 13-3 to give acetal 13-4 (Scheme 13, Step a). An inorganic base such as sodium or potassium hydroxide, or sodium or potassium carbonate, and benzyltriethylammonium chloride, (-)-N-dodecyl-N-methylethoxybenzoate Phase transfer compounds such as tetramethylammonium bromide, tetrapropylammonium bromide, tetrabutylammonium tetrafluoroborate, tetramethylammonium chloride, or tetrabutylammonium hexafluorophosphate Cyclopropyl acetal 13-3 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , and R a (as disclosed above) (Scheme 13, Step b). Caution: Step B is an exothermic reaction, and careful control of the exotherm should be exercised when carrying out this reaction. Cyclopropyl acetal 13-3 can be converted to aldehyde 13-4 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R7 , R 8 , and R 9 can be converted to cyclopropyl acid 1-3 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 The aldehydes 13-4 (as disclosed above) can be obtained by oxidation of the aldehydes 13-4 with an oxidizing agent such as sodium permanganate or potassium permanganate, or under Pinnick oxidation conditions in a polar aprotic solvent selected from the group consisting of acetone, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, and 1,4-dioxane, at about 0 °C to about ambient temperature (Scheme 13, step d). Standard safety precautions should be taken.

[0123] Scheme 13 [ka]

[0124] In some embodiments, cyclopropyl acid 1-3 (R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , and R 9 (as disclosed above) resolves into the (R,R) and (S,S) enantiomers. It will be understood by those skilled in the art that the hydroxyl group can be prepared by the method described in Kovalenko VN, Kulinkovich OG Tetrahedron: Asymmetry 2011, 22, 26 (Scheme 14, step a). Deaf.

[0125] Scheme 14 [ka] [Example]

[0126] This example is for illustrative purposes and should not be construed as limiting the disclosure to only the embodiments disclosed in this example. Starting materials, reagents, and solvents obtained from commercial sources were used without further purification. Anhydrous solvents were purchased as Sure / Seal™ from Aldrich and used as received. Melting points were measured using a Thomas Hoover Unimelt capillary melting point apparatus or a Stumpf melting point apparatus. Stanford Research Systems OptiMelt automated melting point system The data were obtained in a laboratory with a temperature range of about 20°C to about 24°C and are uncorrected. Examples using "room temperature" were performed in a climate-controlled laboratory with temperatures ranging from about 20°C to about 24°C. Molecules were given known names that were named according to naming programs within ISIS Draw, ChemDraw, or ACD Name Pro. These programs When Graham is unable to name a molecule, conventional naming conventions are used to refer to such molecules. 1 H NMR spectral data are in ppm (δ) unless otherwise stated. MHz, or recorded at 600 MHz; 13 C NMR spectral data are in ppm (δ) and were recorded at 75 MHz, 100 MHz, or 150 MHz; 19 F NMR spectral data are in ppm (δ) It was recorded at 376 MHz.

[0127] Example 1: trans-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarboxylic acid Preparation of (C1) [ka] Ruthenium(III) chloride (0.080 g, 0.39 mmol) was dissolved in trans-1,3-dichloro-5-(-2,2- Dichloro-3-(4-methoxyphenyl)cyclopropyl)benzene (C22) (2.8 g, 7.7 mmol) and sodium periodate (33 g, 160 mmol) were added to a stirred mixture of water:ethyl acetate:acetonitrile (8:1:1, 155 mL) at 23 °C. The resulting biphasic brown mixture was vigorously stirred at 23 °C for 5 h. The reaction mixture was diluted with water (1000 mL) and extracted with dichloromethane (4 × 200 mL). The combined organic layers were dried over magnesium sulfate, filtered, and concentrated. The residue was diluted with sodium hydroxide solution (1 M, 100 mL) and washed with diethyl ether (4 × 50 mL). The aqueous layer was The pH was adjusted to 2 with concentrated hydrochloric acid and extracted with dichloromethane (3 x 50 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated to give the title product as a light brown powder (0.78 g, 34% yield). ) obtained as: melting point 117°C-120°C; 1 H NMR(400 MHz, DMSO-d6)δ 13.38 (br s, 1H), 7.52 - 7.65 (m, 3H), 3.57 (d, J = 8.5 Hz, 1H), 3.50 (d, J = 8.5 Hz, 1H);IR (thin film) 3083 (s), 3011 (s), 1731 (s), 1590 (w), 1566 (s), 1448 (w), 1431 (m), 1416 (m) cm -1 . The following compounds were prepared in a manner similar to the procedure outlined in Example 1:

[0128] trans-2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropanecarboxylic acid (C2) [ka] Isolated as a yellow powder (1.5 g, 39%): 1 H NMR (400 MHz, CDCl3) δ 7.31 (d, J = 0.7 Hz, 2H), 3.40 (d, J= 8.2 Hz, 1H), 2.86 (d, J = 8.3 Hz, 1H); 13 C NMR (101 MHz, CDCl3) δ 171.05, 134.55, 132.44, 131.75, 128.89, 61.18, 39.26, 37.14;ESIMS m / z 333 ([MH] - ).

[0129] trans-2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropanecarboxylic acid (C3) [ka] Isolated as an off-white solid (3.2 g, 51%): 1 H NMR (400 MHz, CDCl3) δ 7.47 (d, J = 8.3 Hz, 1H), 7.37 (d, J= 1.6 Hz, 1H), 7.12 (ddd, J = 8.3, 2.1, 0.6 Hz, 1H) , 3.43 (d, J= 8.3 Hz, 1H), 2.86 (d, J = 8.3 Hz, 1H); 13 C NMR (101 MHz, CDCl3) δ 171.52, 132.91, 132.76, 132.29, 130.66, 130.62, 128.02, 61.48, 39.65, 37.13 - ).

[0130] Example 2: trans-2,2-dichloro-3-(4-(trifluoromethyl)phenyl)cyclopropane Preparation of Carboxylic Acid (C4) [ka] trans-1-(2,2-dichloro-3-(4-(trifluoromethyl)phenyl)cyclopropyl)-4- A stirred mixture of methoxybenzene (C25) (3.50 g, 9.60 mmol) and sodium periodate (30.8 g, 144 mmol) in water:ethyl acetate:acetonitrile (8:1:1, 200 mL) was added with ruthenium chloride. Sodium(III) (0.100 g, 0.400 mmol) was added at 23° C. The resulting mixture was stirred at 23° C. for approximately 5 hours. The mixture was stirred vigorously for 1 hour. The reaction mixture was diluted with dichloromethane and washed with water. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography afforded the title compound as an off-white solid (0.630 g, 38%): melting point 100°C-102°C; 1 H NMR (400 MHz, DMSO-d6) δ 13.43 (brs, 1H), 7.77 - 7.73 (m, 2H), 7.67 - 7.64 (m, 2H), 3.55 (d, J = 8.8 Hz, 1H), 3.44 (d, J = 8.8 Hz, 1H);ESIMS m / z 347 ([MH] - ). The following compounds were prepared in a manner similar to the procedure outlined in Example 2:

[0131] trans-2,2-dichloro-3-(3-(trifluoromethyl)phenyl)cyclopropane Carboxylic Acid (C5) [ka] Isolated as an off-white solid (0.81 g, 33%): mp 86-88°C; 1H NMR (400 MHz, DMSO-d6) δ 13.37 (brs, 1H), 7.83 (s, 1H), 7.76 - 7.69 (m, 2H), 7.65 - 7.59 (m, 1H), 3.59 - 3.51 (m, 2H);ESIMS m / z 297 ([MH] - ).

[0132] trans-2,2-dichloro-3-(3-chloro-4-(trifluoromethoxy)phenyl)cyclopropane carboxylic acid (C6) [ka] Isolated as an off-white solid (0.3 g, 19%): mp 134°C-136°C; 1 ESIMS m / z 347 ([MH] - ).

[0133] trans-2,2-dichloro-3-(2,4,5-trichlorophenyl)cyclopropanecarboxylic acid (C7) [ka] Isolated as an off-white solid (0.267 g, 18%): mp 189°C-192°C; 1 H NMR (400 MHz, DMSO-d6) δ 13.44 (brs, 1H), 8.01 (s, 1H), 7.82 (s, 1H), 3.52 (d, J = 8.2 Hz, 1H), 3.29 (d, J = 8.2 Hz, 1H);ESIMS m / z 333 ([MH] - ).

[0134] trans-3-(3,5-bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropanecarboxylic acid (C8) [ka] Isolated as an off-white solid (0.5 g, 31%): mp 112-114°C; 1 H NMR (400 MHz, DMSO-d6) δ 13.43 (brs, 1H), 8.22 (s, 2H), 8.08 (s, 1H), 3.80 - 3.71 (m, 2H);ESIMS m / z 365 ([MH] - ).

[0135] trans-2,2-dichloro-3-(3,5-dibromophenyl)cyclopropanecarboxylic acid (C9) [ka] Isolated as an off-white solid (0.5 g, 24%): mp 157-159°C; 1 H NMR (400 MHz, DMSO-d6) δ 13.36 (brs, 1H), 7.81 (d, J = 1.5 Hz, 2H), 7.72 (d, J = 1.5 Hz, 2H), 3.57 - 3.53 (m, 1H), 3.51 - 3.47 (m, 1H);ESIMS m / z 387 ([MH] - ).

[0136] trans-2,2-dichloro-3-(3-chloro-5-(trifluoromethyl)phenyl)cyclopropane Carboxylic Acid (C10) [ka] Isolated as an off-white solid (0.73 g, 28%): mp 113°C-115°C; 1H NMR (400 MHz, DMSO-d6) δ 13.39 (brs, 1H), 7.91 (s, 1H), 7.86 (s, 1H), 7.84 (s, 1H), 3.69 - 3.60 (m, 2H);ESIMS m / z 333 ([MH] - ).

[0137] trans-2,2-dichloro-3-(3,5-dichloro-4-fluorophenyl)cyclopropanecarboxylic acid Acid (C11) [ka] Isolated as an off-white solid (0.539 g, 34%): 1 H NMR (400 MHz, DMSO-d6): δ 13.37 (brs, 1H), 7.71 (d, J = 6.4 Hz, 2H), 3.42 (s, 2H);ESIMS m / z317 ([MH] - ).

[0138] trans-3-(4-bromo-3,5-dichlorophenyl)-2,2-dichlorocyclopropanecarboxylic acid (C12) [ka] Isolated as an off-white solid (0.100 g, 10%): 1 H NMR (400MHz, DMSO-d6) δ 13.37 (brs, 1H), 7.76 (s, 3H), 3.57 (d, J = 8.8 Hz, 1H), 3.48 (d, J = 8.8 Hz, 1H);ESIMS m / z 377 ([MH] - ).

[0139] trans-3-(3-bromo-5-chlorophenyl)-2,2-dichlorocyclopropanecarboxylic acid (C13) [ka] Isolated as an off-white solid (0.4 g, 25%): mp 161-163°C; 1 H NMR (400MHz, DMSO-d6) δ 13.38 (br s, 1H), 7.70 (d, J = 5.3 Hz, 2H), 7.66 - 7.52 (m, 1H), 3.59 - 3.43 (m, 2H);ESIMS m / z 341 ([MH] - ).

[0140] trans-2,2-dichloro-3-(3-chloro-5-fluorophenyl)cyclopropanecarboxylic acid (C14) [ka] Isolated as an off-white solid (0.700 g, 25%): mp 138°C-140°C; 1 H NMR (400MHz, DMSO-d6) δ 13.38 (brs, 1H), 7.46 (s, 1H), 7.42 (td, J = 2.0, 8.7 Hz, 1H), 7.37 (d, J = 9.8 Hz, 1H), 3.52 (q, J = 8.5 Hz, 2H);ESIMS m / z 281 ([MH] - ).

[0141] trans-2,2-dichloro-3-(4-chloro-3-fluorophenyl)cyclopropanecarboxylic acid (C15) [ka] Isolated as an off-white solid (0.500 g, 20%): mp 140°C-142°C; 1 H NMR (400MHz, DMSO-d6) δ 13.40 (brs, 1H), 7.59 (m, 1H), 7.55 (d, J = 8.4 Hz, 1H), 7.33 (dd, J = 2.0, 8.4 Hz, 1H), 3.55 - 3.38 (m, 2H);ESIMS m / z 281 ([MH] - ).

[0142] trans-2,2-dichloro-3-(3-chloro-4-fluorophenyl)cyclopropanecarboxylic acid (C16) [ka] Isolated as an off-white solid (1.0 g, 53%): mp 121°C-123°C; 1 ESIMS m / z 281 ([MH] - ).

[0143] trans-2,2-dichloro-3-(3-chloro-5-methylphenyl)cyclopropanecarboxylic acid (C17) [ka] Isolated as an off-white solid (1.0 g, 42%): mp 124°C-126°C; 1 H NMR (400 MHz, DMSO-d6) δ 13.33 (brs, 1H), 7.30 (s, 1H), 7.23 (s, 1H), 7.21 (s, 1H), 3.38 (s, 2H), 2.31 (s, 3H);ESIMS m / z277 ([MH] - ).

[0144] trans-2,2-dichloro-3-(3,5-dichloro-4-methylphenyl)cyclopropanecarboxylic acid (C18) [ka] Isolated as an off-white solid (0.8 g, 40%): mp 181°C-183°C; 1 ESIMS m / z311 ([MH] - ).

[0145] trans-2,2-dichloro-3-(3,4-dichloro-5-methylphenyl)cyclopropanecarboxylic acid (C19) [ka] Isolated as an off-white solid (0.73 g, 45%): mp 157-159°C; 1 H NMR (400 MHz, DMSO-d6) δ 13.40 (s, 1H), 7.59 (d, J = 2.0 Hz, 1H), 7.44 (d, J = 1.6 Hz, 1H), 3.43 (q, J = 8.5 Hz, 2H), 2.39 (s, 3H);ESIMS m / z 311 ([MH] - ).

[0146] trans-2,2-dichloro-3-(4-(perfluoroethyl)phenyl)cyclopropanecarboxylic acid (C20) [ka] Isolated as an off-white solid (0.020 g, 10%): mp 116-118°C; 1H NMR (300 MHz, CDCl3) δ 7.63 (d, J = 8.1 Hz, 2H), 7.42 (d, J = 8.1 Hz, 2H), 3.53 (d, J = 8.4 Hz, 1H), 2.94 (d, J = 8.4 Hz, 1H);ESIMS m / z347 ([MH] - ).

[0147] trans-2,2-dichloro-3-(4-ethoxyphenyl)cyclopropanecarboxylic acid (C21) [ka] Isolated as an off-white solid (0.025 g, 5%): mp 129°C-130°C; 1 H NMR (400 MHz, CDCl3) δ 7.16 (d, J = 8.4 Hz, 2H), 6.88 (d, J = 8.31 Hz, 2H), 4.03 (q, J = 6.8 Hz, 2H), 3.41 (d, J = 8.0 Hz, 1H), 2.81 (d, J = 8.0 Hz, 1H), 1.41 (t, J = 6.8 Hz, 3H);ESIMS m / z 273 ([MH] - ).

[0148] Example 3: trans-1,3-dichloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)cyclopropanol Preparation of (C22)pyr)benzene [ka] Aqueous sodium hydroxide (50%, 6.8 mL, 130 mmol) was added to (E)-1,3-dichloro-5-(4-methyl- To a stirred solution of N-benzyl-N,N-diethylethanaminium chloride (0.20 g, 0.86 mmol) in chloroform (14 mL, 170 mmol) was added at 23°C. The resulting biphasic dark brown mixture was vigorously stirred at 23°C for 24 hours. The reaction mixture was diluted with water (200 mL) and extracted with dichloromethane (2 x 100 mL). The combined organic layers were Drying over magnesium sulfate, filtration and concentration gave the title product as a brown oil (2.8 g, 90%): 1 H NMR (400 MHz, CDCl3) δ 7.34 (t, J = 1.8 Hz, 1H), 7.21 - 7.30 (m, 4H), 6.93 (m, 2H), 3.83 (s, 3H), 3.14 (d, J = 8.5 Hz, 1H), 3.08 (d, J = 8.5 Hz, 1H);IR (thin film) 3075 (w), 2934 (w), 2836 (w), 1724 (w), 1640 (w), 1609 (m), 1584 (m), 1568 (s), 1513 (s) cm -1 . The following compounds were prepared in a manner similar to the procedure outlined in Example 3:

[0149] trans-1,2,3-trichloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl) Benzene (C23) [ka] Isolated as a dark foam (4.7 g, 100%): 1 H NMR (400 MHz, CDCl3) δ 7.40 (d, J = 0.6 Hz, 2H), 7.29 - 7.22 (m, 2H), 6.96 - 6.89 (m, 2H), 3.83 (s, 3H), 3.12 (d, J = 8.8 Hz, 1H), 3.06 (d, J = 8.7 Hz, 1H); 13C NMR (101 MHz, CDCl3) δ 159.46 , 135.08, 134.23, 130.91, 129.85, 129.16, 125.42, 114.02, 64.67, 55.32, 39.62, 38.48.

[0150] trans-1,2-dichloro-4-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)benzene Zen (C24) [ka] Isolated as an orange-red oil (7.6 g, 99%): 1 H NMR (400 MHz, CDCl3) δ 7.47 (d, J = 4.9 Hz, 1H), 7.45 (bs, 1H), 7.30 - 7.23 (m, 2H), 7.21 (dd, J = 8.2, 1.9 Hz, 1H), 6.96 - 6.90 (m, 2H), 3.83 (s, 3H), 3.11 (app. q, J= 8.8 Hz, 2H); 13 C NMR (101 MHz, CDCl3) δ 159.39, 134.90, 132.62, 131.99, 130.90, 130.40, 129.90, 128.33, 125.81, 113.98, 64.94, 55.33, 39.52, 38.75.

[0151] Example 4: Preparation of trans-1-(2,2-dichloro-3-(4-(trifluoromethyl)phenyl)cyclopropyl)-4-methoxybenzene (C25) [ka] (E)-1-Methoxy-4-(4-(trifluoromethyl)styryl)benzene (C46) (4.00 g, 14.0 mmol) and N-benzyl-N,N-diethylethanaminium chloride (0.320 g, 14.0 mmol) To a stirred solution of 1,2-dichloromethane (23.1 g, 288 mmol) in chloroform at 23° C., sodium hydroxide (50%, 8.64 g, 216 mmol) in water (17 mL) was added at 23° C., and the resulting mixture was vigorously stirred at 23° C. for 16 hours. The reaction mixture was diluted with water and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography afforded the title compound as an off-white solid (3.70 g, 68%): 1 H NMR (300 MHz, CDCl3) δ 7.65 (d, J = 8.4 Hz, 2H), 7.49 (d, J = 8.4 Hz, 2H), 7.29 (d, J = 8.4 Hz, 2H), 6.94 (d, J = 8.4 Hz, 2H), 3.83 (s, 3H), 3.19 (s, 2H);ESIMS m / z361 ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 4:

[0152] trans-1-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-3-(trifluoromethyl)benzene (C26) [ka] Isolated as a brown liquid (3.5 g, 67%): 1 H NMR (300 MHz, CDCl3) δ 7.62 - 7.50 (m, 4H), 7.29 (d, J = 9.0 Hz, 2H), 6.94 (d, J = 9.0 Hz, 2H), 7.35 - 7.25 (m, 3H), 7.97 - 6.88 (m, 1H), 3.83 (s, 3H), 3.19 (m, 2H);ESIMS m / z 361 ([M+H] + ).

[0153] trans-2-chloro-4-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-1-(trichlorophenyl) Fluoromethoxy)benzene (C27) [ka] Isolated as an off-white solid (2.5 g, 65%): 1 H NMR (400 MHz, CDCl3) δ 7.57 (d, J = 2.0 Hz, 1H), 7.44 (d, J = 8.8 Hz, 1H), 7.35 - 7.25 (m, 3H), 7.97 - 6.88 (m, 1H), 3.84 (s, 3H), 3.15 - 3.05 (m, 2H);ESIMS m / z 411 ([M+H] + ).

[0154] trans-1,2,4-trichloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl) Benzene (C28) [ka] Isolated as a brown liquid (2.0 g, 58%): EIMS m / z 394 ([M] + ).

[0155] trans-1-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-3,5-bis(trifluoromethyl)benzene (C29) [ka] Isolated as a brown liquid (3.0 g, 61%): EIMS m / z 428 ([M] + ).

[0156] trans-1,3-dibromo-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)benzene Zen (C30) [ka] Isolated as a brown liquid (3.0 g, 57%): 1 H NMR (300 MHz, CDCl3) δ 7.64 (s, 1H), 7.45 (s, 2H), 7.25 (d, J = 9.0 Hz, 2H), 6.92 (d, J = 9.0 Hz, 1H), 3.83 (s, 3H), 3.15 - 3.05 (m, 2H);ESIMS m / z 453 ([M+H] + ).

[0157] trans-1-chloro-3-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-5-(trichlorophenyl) Fluoromethyl)benzene (C31) [ka] Isolated as a brown solid (4.0 g, 74%): 1 H NMR (300 MHz, CDCl3) δ 7.64 (s, 1H), 7.45 (s, 1H), 7.42 (s, 1H), 7.26 (d, J = 9.0 Hz, 2H), 6.93 (d, J = 9.0 Hz, 1H), 3.83 (s, 3H), 3.15 - 3.05 (m, 2H);ESIMS m / z 395 ([M+H] + ).

[0158] trans-1,3-dichloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-2-fluorobenzene (C32) [ka] Isolated as a brown solid (1.6 g, 54%): 1 H NMR (300 MHz, CDCl3) δ 7.32 (d, J = 6.0 Hz, 2H), 7.30 (d, J = 9.0 Hz, 1H), 6.93 (d, J = 9.0 Hz, 1H), 3.83 (s, 3H), 3.12 - 3.05 (m, 2H);ESIMS m / z 297 ([M+H] +).

[0159] trans-2-bromo-1,3-dichloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropane) Pyr) Benzene (C33) [ka] Isolated as an off-white solid (1.5 g, 44%): 1 H NMR (300 MHz, CDCl3) δ 7.36 (d, J = 9.0 Hz, 2H), 7.20 (s, 2H), 6.93 (d, J = 9.0 Hz, 2H), 3.83 (s, 3H), 3.15 - 3.05 (m, 2H);ESIMS m / z 439 ([M+H] + ).

[0160] trans-1-bromo-3-chloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)benzene (C34) [ka] Isolated as an off-white solid (2.5 g, 50%): 1 H NMR (400 MHz, CDCl3) δ 7.49 (s, 1H), 7.30 (s, 1H), 7.28 - 7.24 (m, 3H), 6.92 (d, J = 8.0 Hz, 2H), 3.92 (s, 3H), 3.01 (q, J = 8.8 Hz, 2H);ESIMS m / z 405 ([M+H] + ).

[0161] trans-1-chloro-3-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-5-fluorobenzene (C35) [ka] Isolated as a brown liquid (3.5 g, 67%): ESIMS m / z 345 ([M+H] + ).

[0162] trans-1-chloro-4-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-2-fluorobenzene (C36) [ka] Isolated as an off-white solid (2.5 g, 65%): ESIMS m / z 345 ([M+H] + ).

[0163] trans-2-chloro-4-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-1-fluorobenzene (C37) [ka] Isolated as a brown liquid (2.0 g, 58%): ESIMS m / z 345 ([M+H] + ).

[0164] trans-1-chloro-3-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-5-methylbenzene (C38) [ka] Isolated as an off-white solid (3.0 g, 47%): 1 H NMR (400 MHz, CDCl3) δ 7.27 (d, J = 8.8 Hz, 2H), 7.14 (s, 2H), 7.06 (s, 1H), 6.92 (d, J = 8.8 Hz, 2H), 3.82 (s, 3H), 3.10 (q, J = 8.8 Hz, 2H), 2.36 (s, 3H);ESIMS m / z341 ([M+H] + ).

[0165] trans-1,3-dichloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-2-methylbenzene (C39) [ka] Isolated as a brown liquid (2.5 g, 80%): 1 H NMR (400 MHz, CDCl3) δ 7.25 (d, J = 8.0 Hz, 2H), 7.17 (d, J = 8.8 Hz, 1H), 6.92 (d, J = 8.0 Hz, 2H), 6.88 (d, J = 8.8 Hz, 1H), 3.82 (s, 3H),3.12 - 3.03 (m, 2H), 2.47 (s, 3H);ESIMS m / z 375 ([M+H] + ).

[0166] trans-1,2-dichloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-3-methylbenzene (C40) [ka] Isolated as a brown liquid (4.0 g, 90%): ESIMS m / z 375 ([M+H] + ).

[0167] trans-1-(2,2-dichloro-3-(4-(perfluoroethyl)phenyl)cyclopropyl)-4- Methoxybenzene (C41) [ka] Isolated as an off-white solid (0.5 g, 46%): 1 H NMR (400 MHz, CDCl3) δ 7.60 - 7.50 (m, 4H), 7.47 (d, J = 8.0 Hz, 2H), 6.92 (d, J = 8.0 Hz, 2H), 3.82 (s, 3H), 3.20 (s, 2H);ESIMS m / z411 ([M+H] +).

[0168] trans-4,4'-(3,3-dichlorocyclopropane-1,2-diyl)bis(ethoxybenzene)(C42) [ka] Isolated as an off-white solid (1.5 g, 45%): 1 H NMR (400 MHz, CDCl3) δ ESIMS m / z 351 ([M+H] + ).

[0169] Example 5: Preparation of (E)-1,3-dichloro-5-(4-methoxystyryl)benzene (C43) [ka] Sodium methoxide powder (98%, 0.63 g, 11 mmol) was dissolved in 3,5-dichlorobenzaldehyde (2.0 g, 11 mmol) and diethyl 4-methoxybenzylphosphonate (2.0 mL, 11 mmol). was added to a stirred solution of anhydrous N,N-dimethylformamide (38 mL) at 23°C. The dark blue mixture was heated to 80°C, resulting in a dark brown mixture, which was stirred for 24 hours. The cooled reaction mixture was diluted with water (500 mL) and extracted with diethyl ether (3 x 100 mL). The combined organic layers were diluted with hexane (150 mL) and washed with water (300 mL). The organic layers were dried over magnesium sulfate, filtered, and concentrated to give the title product as a light brown oil (2.4 g, 75%): 1H NMR (400 MHz, CDCl3) δ 7.44 (m, 2H), 7.34 (d, J = 2 Hz, 2H), 7.20 (t, J = 2 Hz, 1H), 7.06 (d, J = 16.5 Hz, 1H), 6.91 (m, 2H), 6.82 (d, J = 16.5 Hz, 1H), 3.84 (s, 3H); IR (thin film) 2934 (w), 2835 (w), 1724 (w), 1637 (w), 1605 (m), 1581 (m), 1558 (m), 1511 (s) cm -1 . The following compounds were prepared in a manner similar to the procedure outlined in Example 5:

[0170] (E)-1,2,3-trichloro-5-(4-methoxystyryl)benzene (C44) [ka] Isolated as an off-white solid (3.7 g, 31%): 1 H NMR (400 MHz, CDCl3) δ 7.49 - 7.46 (m, 2H), 7.47 - 7.39 (m, 2H), 7.04 (d, J = 16.3 Hz, 1H), 6.93 - 6.89 (m, 2H), 6.78 (d, J= 16.3 Hz, 1H), 3.84 (s, 3H); 13 EIMS m / z 313 ([M] + ).

[0171] (E)-1,2-Dichloro-4-(4-methoxystyryl)benzene (C45) [ka] Isolated as an off-white solid (6.0 g, 53%): mp 91-94°C; 1 H NMR (400 MHz, CDCl3) δ 7.56 (d, J = 2.0 Hz, 1H), 7.46 - 7.42 (m, 2H), 7.39 (d, J = 8.4 Hz, 1H), 7.29 (dd, J = 8.4, 2.1 Hz, 1H), 7.04 (d, J = 16.2 Hz, 1H), 6.93 - 6.88 (m, 2H), 6.85 (d, J = 16.3 Hz, 1H), 3.84 (s, 3H); 13 C NMR (101 MHz, CDCl3) δ 159.75, 137.86, 132.72, 130.58, 130.49, 130.12, 129.33, 127.96, 127.77, 125.37, 123.98, 114.24, 55.35;EIMS m / z 279 ([M] + ).

[0172] Example 6: Preparation of (E)-1-methoxy-4-(4-(trifluoromethyl)styryl)benzene (C46) [ka] Diethyl 4-methoxybenzylphosphonate (8.89 g, 34.0 mmol) in N,N-dimethylform To a stirred solution of amide (30 mL) was added sodium methoxide powder (1.86 g, 34.0 mmol). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was cooled to 0°C, and 4-(trifluoromethyl)benzaldehyde (5.00 g, 28.0 mmol) in N,N-dimethylformamide (30 mL) was added dropwise. The reaction mixture was stirred at 60°C for 2 hours. The reaction mixture was poured into ice-cold water. , filtered and dried to give the title compound as an off-white solid (3.60 g, 80%) : 1H NMR (300 MHz, CDCl3) δ 7.61 - 7.52 (m, 4H), 7.47 (d, J = 9.0 Hz, 2H), 7.14 (d, J = 16.5 Hz, 1H), 6.97 (d, J = 16.5 Hz, 1H), 6.91 (d, J = 9.0 Hz, 2H), 3.84 (s, 3H); ESIMS m / z 279 ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 6:

[0173] (E)-1-(4-methoxystyryl)-3-(trifluoromethyl)benzene (C47) [ka] Isolated as an off-white solid (4.0 g, 85%): 1 H NMR (400 MHz, CDCl3) δ 7.72 (s, 1H), 7.64 (d, J = 6.8 Hz, 1H), 7.50 - 7.44 (m, 4H), 7.12 (d, J = 16.0 Hz, 1H), 6.98 (d, J = 16.0 Hz, 1H), 6.91 (d, J = 8.8 Hz, 2H), 3.84 (s, 3H);ESIMS m / z 279 ([M+H] + ).

[0174] (E)-2-chloro-4-(4-methoxystyryl)-1-(trifluoromethoxy)benzene (C48) [ka] Isolated: ESIMS m / z 329 ([M+H] + ).

[0175] (E)-1-(4-methoxystyryl)-3,5-bis(trifluoromethyl)benzene (C49) [ka] Isolated as an off-white solid (4.0 g, 56%): 1 H NMR (300 MHz, CDCl3) δ 7.88 (s, 2H), 7.70 (s, 1H), 7.49 (d, J = 8.4 Hz, 2H), 7.19 (d, J = 16.5 Hz, 1H), 6.99 (d, J = 16.5 Hz, 1H), 6.92 (d, J = 8.4 Hz, 2H), 3.84 (m, 3H);ESIMS m / z 347 ([M+H] + ).

[0176] (E)-1,3-Dibromo-5-(4-methoxystyryl)benzene (C50) [ka] Isolated as an off-white solid (2.2 g, 54%): 1 H NMR (300 MHz, CDCl3) δ 7.53 (s, 1H), 7.50 (s, 2H), 7.43 (d, J = 9.0 Hz, 2H), 7.05 (d, J = 16.2 Hz, 1H), 6.90 (d, J = 9.0 Hz, 2H), 6.79 (d, J = 16.2 Hz, 1H), 3.80 (s, 3H); ESIMS m / z 367 ([M+H] + ).

[0177] (E)-1-chloro-3-(4-methoxystyryl)-5-(trifluoromethyl)benzene (C51) [ka] Isolated as an off-white solid (4.3 g, 58%): 1H NMR (300MHz, CDCl3) δ 7.62 (s, 1H), 7.58 (s, 1H), 7.48 - 7.42 (m, 3H), 7.12 (d, J = 16.2 Hz, 1H), 6.95 - 6.85(m, 3H), 3.84 (s, 3H);ESIMS m / z 313 ([M+H] + ).

[0178] (E)-2-Bromo-1,3-dichloro-5-(4-methoxystyryl)benzene (C52) [ka] Isolated as an off-white solid (2.8 g, 40%): 1 H NMR (300 MHz, CDCl3) δ 7.46 (s, 2H), 7.43 (d, J = 9.0 Hz, 2H), 7.07 (d, J = 13.5 Hz, 1H), 6.90 (d, J = 9.0 Hz, 1H), 6.73 (d, J = 13.5 Hz, 1H), 3.84 (s, 3H);ESIMS m / z 358 ([M+H] + ).

[0179] (E)-1-Bromo-3-chloro-5-(4-methoxystyryl)benzene (C53) [ka] Isolated as an off-white solid (4.0 g, 63%): 1 H NMR (300 MHz, CDCl3) δ 7.49 (s, 1H), 7.43 (d, J = 8.4 Hz, 2H), 7.38 (s, 1H), 7.35 (s, 1H), 7.05 (d, J = 16.5 Hz, 1H), 6.91 (d, J = 8.4 Hz, 2H), 6.80 (d, J = 16.5 Hz, 1H), 3.82 (s, 3H);ESIMS m / z 323 ([M+H]+ ).

[0180] (E)-1-chloro-3-fluoro-5-(4-methoxystyryl)benzene (C54) [ka] Isolated as an off-white solid (5.0 g, 60%): 1 H NMR (400 MHz, CDCl3) δ 7.45 (d, J = 8.4 Hz, 2H), 7.10 - 7.0 (m, 3H), 6.96 - 6.80 (m, 4H), 3.80 (s, 3H);ESIMS m / z263 ([M+H] + ).

[0181] (E)-1-chloro-2-fluoro-4-(4-methoxystyryl)benzene (C55) [ka] Isolated as an off-white solid (7.0 g, 84%): 1 H NMR (400 MHz, CDCl3) δ 7.44 (d, J = 8.0 Hz, 2H), 7.35 - 7.31 (m, 1H), 7.28 - 7.24 (m, 1H), 7.17 (dd, J = 1.6, 8.0 Hz, 1H), 7.03 (d, J = 16.0 Hz, 1H), 6.90 (d, J = 8.0 Hz, 1H), 7.49 (d, J = 8.0 Hz, 1H), 6.86 (d, J = 16.0 Hz, 1H), 3.82 (s, 3H);ESIMS m / z 263 ([M+H] + ).

[0182] (E)-2-chloro-1-fluoro-4-(4-methoxystyryl)benzene (C56) [ka] Isolated as an off-white solid (6.0 g, 72%): ESIMS m / z 263 ([M+H] + ).

[0183] (E)-1-chloro-3-(4-methoxystyryl)-5-methylbenzene (C57) [ka] Isolated as an off-white solid (5.0 g, 60%): 1 H NMR (300 MHz, CDCl3) δ 7.44 (d, J = 8.4 Hz, 2H), 7.28 (s, 1H), 7.15 (s, 1H), 7.05 - 7.00 (m, 2H), 6.91 - 6.83 (m, 3H), 3.83 (s, 3H), 2.24 (s, 3H);ESIMS m / z 259 ([M+H] + ).

[0184] (E)-1-Methoxy-4-(4-(perfluoroethyl)styryl)benzene (C58) [ka] Isolated as an off-white solid (0.5 g, 42%): 1 H NMR (400 MHz, CDCl3) δ 7.60 - 7.50 (m, 4H), 7.47 (d, J = 8.8 Hz, 2H),7.15 (d, J = 16.8 Hz, 1H), 6.98 (d, J = 16.8 Hz, 1H), 6.92 (d, J = 8.8 Hz, 2H), 3.82 (s, 3H);ESIMS m / z 329 ([M+H] + ).

[0185] (E)-1,2-bis(4-ethoxyphenyl)ethene (C59) [ka] Isolated as an off-white solid (1.7 g, 34%): 1 H NMR (300 MHz, CDCl3) δ 7.40 (d, J = 9.0 Hz, 4H), 6.91 (s, 2H), 6.87 (d, J = 9.0 Hz, 4H), 4.05 (q, J = 6.9 Hz, 4H), 1.42 (t, J = 6.9 Hz, 6H), + ).

[0186] Example 7: Preparation of (E)-1,3-dichloro-2-fluoro-5-(4-methoxystyryl)benzene (C60) [ka] A stirred mixture of 5-bromo-1,3-dichloro-2-fluorobenzene (2.00 g, 8.20 mmol), 1-methoxy-4-vinylbenzene (1.32 g, 9.80 mmol), and triethylamine (20 mL) was degassed under argon for 5 minutes. Palladium(II) acetate (0.0368 g, 0.164 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (0.181 g, 0.328 mmol) were added, and the reaction was heated to 90° C. for 16 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography afforded the title compound as an off-white solid (1.60 g, 67%): 1 H NMR (300 MHz, CDCl3) δ 7.41 (d, J = 8.8 Hz, 2H), 7.31 (s, 1H), 7.37 (s, 1H), 6.96 (d, J = 16.0 Hz, 1H), 6.89 (d, J = 8.8 Hz, 2H), 6.76 (d, J = 16.0 Hz, 1H), 3.84 (s, 3H); ESIMS m / z 297 ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 7:

[0187] (E)-1,3-Dichloro-5-(4-methoxystyryl)-2-methylbenzene (C61) [ka] Isolated as an off-white solid (2.5 g, 67%): 1 H NMR (300 MHz, CDCl3) δ 7.43 (d, J = 8.7 Hz, 2H), 7.38 (s, 2H), 7.02 (d, J = 16.5 Hz, 1H), 6.90 (d, J = 8.7 Hz, 2H), 6.79 (d, J = 16.5 Hz, 1H), 3.82 (s, 3H), 2.42 (s, 3H);ESIMS m / z 293 ([M+H] + ).

[0188] (E)-1,2-Dichloro-5-(4-methoxystyryl)-3-methylbenzene (C62) [ka] Isolated as an off-white solid (3.0 g, 55%): 1 H NMR (300 MHz, CDCl3) δ 7.50 - 7.40 (m, 3H), 7.24 (s, 1H), 7.02 (d, J = 15.9 Hz, 1H), 6.90 (d, J = 9.0 Hz, 2H), 6.81 (d, J = 15.9 Hz, 1H), 3.83 (s, 3H), 2.42 (s, 3H);ESIMS m / z 293 ([M+H] + ).

[0189] Example 8: Preparation of (E)-1,2,4-trichloro-5-(4-methoxystyryl)benzene (C63) [ka] 1-Bromo-2,4,5-trichlorobenzene (3.0 g, 12 mmol) and 1,2-dimethoxyethane: water (10:1, 30 mL) and (E)-2-(4-methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxide. Xaborolane (C64) (3.7 g, 14 mmol) and potassium carbonate (3.2 g, 24 mmol) were placed in a sealed tube. The reaction mixture was degassed with argon for 10 minutes, and then tetrakis(triphenylphosphine) (fin)palladium(0) (0.55 g, 0.48 mmol) was added. The reaction mixture was degassed for 10 minutes. The mixture was then heated at 90° C. for 16 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave the title compound as an off-white solid (3.0 g, 80%). Ta: 1 H NMR (400 MHz, CDCl3) δ 7.73 (s, 1H), 7.50 - 7.45 (m, 3H), 7.20 (d, J = 16.0 Hz, 1H), 7.02 (d, J = 16 Hz, 1H), 6.92 (d, J = 8.0 Hz, 2H), 3.84 (m, 3H);ESIMS m / z 313 ([M+H] + ).

[0190] Example 9: (E)-2-(4-methoxystyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Preparation of (C64) [ka] 1-ethynyl-4-methoxybenzene (4.0 g, 30 mmol), 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.3 g, 36 mmol), zirconocene hydrochloride (1.2 g, 4.0 mmol), Triethylamine (2.8 mL, 15 mmol) was added to a 50 mL round-bottom flask at 0°C. The reaction mixture was stirred at 65°C for 16 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography afforded the title compound as an off-white semi-solid (3.0 g, 38%): 1 H NMR (400 MHz, CDCl3) δ 7.43 (d, J = 8.8 Hz, 2H), 7.35 (d, J = 18.0 Hz, 1H), 6.86 (d, J = 8.8 Hz, 2H), 6.01 (d, J = 18.0 Hz, 1H), 3.81 (s, 3H), 1.30 (s, 12H).

[0191] Example 10: Preparation of 3,4,5-trichlorobenzaldehyde (C65) [ka] In an oven-dried, nitrogen-flushed 500 mL round-bottom flask equipped with a pressure-equalizing addition funnel, add 5-bromo Mo-1,2,3-trichlorobenzene (10.0 g, 38.4 mmol) was dissolved in tetrahydrofuran (100 mL), and the resulting solution was cooled in an ice bath under nitrogen. Isopropylmagnesium chloride (2 M in tetrahydrofuran, 21.1 mL, 42.3 mmol) was added and stirred thoroughly for 15 minutes. The solution was added dropwise via an addition funnel while stirring. After 0.5 h, N,N-dimethylformamide (3.72 mL, 48.0 mmol) was added to the dark solution with stirring. After an additional 0.5 h, hydrochloric acid (1 N, 100 mL) was added with stirring. The layers were separated and the organic layer was washed with brine. The combined aqueous layer was Extraction with ether, drying of the combined organic layers over sodium sulfate, filtration and concentration gave the title compound as a white solid (title compound:1,2,3-trichlorobenzene 10:1 mixture, 7.96 g, 99% yield). ) was obtained. 1H NMR (CDCl3) δ 9.91 (s, 1H), 7.88 (s, 2H); EIMS m / z 209 ([M] + ) .

[0192] Example 11: Preparation of 1-bromo-4-(perfluoroethyl)benzene (C66) [ka] To a stirred solution of 1-(4-bromophenyl)-2,2,2-trifluoroethanone (5.00 g, 19.7 mmol) in dichloromethane under argon, 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride (2.90 g, 11.8 mmol) and hydrogen fluoride pyridine complex (0.190 g, 9.80 mmol) were added at 0°C. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography afforded the title compound as a colorless liquid (1.00 g, 20%): 1 H NMR (300 MHz, CDCl3) δ 7.65 (d, J = 9.0 Hz, 2H), 7.47 (d, J = 9.0 Hz, 2H); EIMS m / z 274 ([M] + ).

[0193] Example 12: Preparation of trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarboxamido)benzoic acid (C67) [ka] trans-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarbonate stirred at 0°C To a solution of carboxylic acid (C1) (0.300 g, 1.00 mmol) in dichloromethane (5.00 mL), Add 1 drop of methylformamide, then add 0.131 mL of oxalyl chloride (1.50 mmol) over 2 min. The ice batch was removed and the reaction was allowed to warm to room temperature over 90 minutes. The reaction mixture was then concentrated to give an orange-yellow semi-solid. The semi-solid was dissolved in dichloromethane (3.5 mL), and the solution was added with 5-amino-2-chlorobenzoic acid (0.206 g, 1.20 mmol) and trichlorobenzoic acid (0.416 g, 1.20 mmol). Slowly add ethylamine (0.209 mL, 1.50 mmol) to a cooled solution of dichloromethane (7 mL). The ice bath was removed and the reaction was allowed to warm to room temperature over 90 minutes. The reaction was diluted with dichloromethane (10 mL) and washed with hydrochloric acid (0.1 N). The resulting slurry was filtered and the solid was washed with water. The precipitated solid was dried in a vacuum oven at 40°C to give the title compound as a light brown solid (0.421 g, 93%): mp 234-236°C; 1 H NMR (400 MHz, DMSO-d6) δ 13.47 (s, 1H), 10.90 (s, 1H), 8.16 (d, J= 2.3 Hz, 1H), 7.78 (dd, J = 8.7, 2.4 Hz, 1H), 7.59 (m, 4H), 3.56 (dd, J = 49.8, 8.5 Hz, 2H), 1.09 (m, 1H); 13 C NMR (101 MHz, DMSO-d6) δ 166.26, 165.77, 162.61, 137.57, 137.27, 134.04, 132.18, 131.44, 131.22, 127.88, 127.66, 126.40, 125.92, 122.88, 121.17, 102.37, 62.11, 38.41, 36.83;ESIMS m / z 454 ([M+H] + ).

[0194] Example 13: Preparation of trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (F1) [ka] 5-Amino-2-chloro-N-(4-fluorophenyl)benzamide (C69) (0.174 g, 0.656 mmol) and 4-dimethylaminopyridine (0.087 g, 0.711 mmol) were added sequentially to a stirred mixture of trans-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarboxylic acid (C1) (0.164 g, 0.547 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.157 g, 0.820 mmol) in 1,2-dichloroethane (5.5 mL) at room temperature. The reaction was stirred at room temperature for 20 hours. The reaction was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate (2x). The residue was washed with 1 N hydrochloric acid (2×). The organic phase was dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography using 0% to 100% ethyl acetate / hexanes as eluent afforded the title compound as a white foam (0.138 g, 46%). The following compounds were prepared in a manner similar to the procedure outlined in Example 13:

[0195] trans-3-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (F2) [ka] Isolated as a brown solid (0.106 g, 79%).

[0196] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-(trifluoromethyl)benzamide (F3) [ka] Isolated as a yellow solid (0.074 g, 34%).

[0197] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-iodobenzamide (F4) [ka] Isolated as a brown solid (0.078 g, 50%).

[0198] trans-2-chloro-N-(4-cyanophenyl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl) Cyclopropane-1-carboxamido)benzamide (F5) [ka] Isolated as a yellow solid (0.081 g, 39%).

[0199] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-(trifluoromethyl)phenyl)benzamide (F6) [ka] Isolated as a yellow solid (0.082 g, 49%).

[0200] trans-2-chloro-N-(4-chlorophenyl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl) Cyclopropane-1-carboxamido)benzamide (F7) [ka] Isolated as a yellow solid (0.083 g, 47%).

[0201] trans-2-chloro-N-(2-chloro-4-fluorophenyl)-5-(2,2-dichloro-3-(3,5-dichloro)phenyl)- (phenyl)cyclopropane-1-carboxamido)benzamide (F8) [ka] Isolated as a yellow solid (0.075 g, 42%).

[0202] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido-N-(o-tolyl)benzamide (F9) [ka] Isolated as a brown solid (0.104 g, 54%).

[0203] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-methylbenzamide (F10) [ka] Isolated as a white solid (0.095 g, 50%).

[0204] trans-2-bromo-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido-N-(4-fluorophenyl)benzamide (F11) [ka] Isolated as a red solid (0.085 g, 51%).

[0205] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)benzamide (F12) [ka] Isolated as a brown solid (0.103 g, 60%).

[0206] trans-2-chloro-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1- Carboxamido)-N-(4-fluorophenyl)benzamide (F13) [ka] Isolated as a white powder (0.090 g, 79%).

[0207] trans-2-chloro-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)benzamide (F14) [ka] Isolated as an off-white powder (0.155 g, 77%).

[0208] trans-3-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-(4-fluorophenyl)benzamide (F15) [ka] Isolated as a yellow oil (0.025 g, 18%).

[0209] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido-N-phenylbenzamide (F16) [ka] Isolated as a white solid (0.092 g, 66%).

[0210] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido-N-(2-fluorophenyl)benzamide (F17) [ka] Isolated as a white solid (0.030 g, 21%).

[0211] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2,4-difluorophenyl)benzamide (F18) [ka] Isolated as a white solid (0.108 g, 72%).

[0212] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F19) [ka] Isolated as a white solid (0.137 g, 92%).

[0213] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(3-fluorophenyl)benzamide (F20) [ka] Isolated as a pink solid (0.115 g, 79%).

[0214] trans-2-chloro-N-(3-cyanophenyl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl) Cyclopropane-1-carboxamido)benzamide (F21) [ka] Isolated as a white solid (0.113 g, 76%).

[0215] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2,3-difluorophenyl)benzamide (F22) [ka] Isolated as a white solid (0.120 g, 79%).

[0216] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(3,4-difluorophenyl)benzamide (F23) [ka] Isolated as a white solid (0.121 g, 80%).

[0217] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2,4,6-trifluorophenyl)benzamide (F24) [ka] Isolated as a pale pink solid (0.109 g, 70%).

[0218] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2,6-difluorophenyl)benzamide (F25) [ka] Isolated as a pale pink solid (0.092 g, 61%).

[0219] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido-N-(pyridin-4-yl)benzamide (F26) [ka] Isolated as a white solid (0.112 g, 64%).

[0220] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido-N-(pyridin-3-yl)benzamide (F27) [ka] Isolated as a white solid (0.138 g, 78%).

[0221] trans-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-(4-fluorophenyl)benzamide (F28) [ka] Isolated as a white solid (0.130 g, 92%).

[0222] trans-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-(4-fluorophenyl)benzamide (F29) [ka] Isolated as a white solid (0.121 g, 90%).

[0223] trans-3-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide )-N-(4-fluorophenyl)-2-methoxybenzamide (F30) [ka] Isolated as a yellow solid (0.069 g, 47%).

[0224] trans-2-chloro-N-(2-chloropyridin-3-yl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl)- (phenyl)cyclopropane-1-carboxamido)benzamide (F31) [ka] Isolated as a white solid (0.126 g, 67%).

[0225] trans-2-chloro-N-(6-chloropyridin-3-yl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl)- (phenyl)cyclopropane-1-carboxamido)benzamide (F32) [ka] Isolated as a white solid (0.131 g, 70%).

[0226] trans-2-chloro-N-(6-cyanopyridin-3-yl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl)- (phenyl)cyclopropane-1-carboxamido)benzamide (F33) [ka] Isolated as a white solid (0.094 g, 51%).

[0227] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(3-fluorophenyl)-N-methylbenzamide (F34) [ka] Isolated as a white solid (0.119 g, 80%).

[0228] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2-fluorophenyl)-N-methylbenzamide (F35) [ka] Isolated as a white solid (0.123 g, 82%).

[0229] trans-2-chloro-N-(4-cyano-2-methylphenyl)-5-(2,2-dichloro-3-(3,5-dichloro) Phenyl)cyclopropane-1-carboxamido)benzamide (F36) [ka] Isolated as a white solid (0.103 g, 68%).

[0230] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluoro-2-methylphenyl)benzamide (F37) [ka] Isolated as a white solid (0.112 g, 75%).

[0231] trans-2-chloro-N-(2-chlorophenyl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl) Cyclopropane-1-carboxamido)benzamide (F38) [ka] Isolated as a white foam (0.101 g, 77%).

[0232] trans-2-chloro-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2,4-difluorophenyl)benzamide (F39) [ka] Isolated as a white foam (0.096 g, 68%).

[0233] trans-2-chloro-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1- Carboxamido)-N-(2,4-difluorophenyl)benzamide (F40) [ka] Isolated as a white solid (0.104 g, 77%).

[0234] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2-isopropylphenyl)benzamide (F41) [ka] Isolated as a white solid (0.104 g, 78%).

[0235] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2-ethyl-6-methylphenyl)benzamide (F42) [ka] Isolated as a white solid (0.103 g, 77%).

[0236] trans-2-chloro-N-(3-chlorophenyl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl) Cyclopropane-1-carboxamido)benzamide (F43) [ka] Isolated as a white solid (0.029 g, 22%).

[0237] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2,4-difluorophenyl)-N-methylbenzamide (F44) [ka] Isolated as a white foam (0.082 g, 57%).

[0238] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-(4-fluorophenyl)-N-methylbenzamide (F45) [ka] Isolated as a white solid (0.077 g, 57%).

[0239] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-(3-fluorophenyl)-N-methylbenzamide (F46) [ka] Isolated as a white solid (0.096 g, 70%).

[0240] trans-3-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-(4-fluorophenyl)-N-methylbenzamide (F47) [ka] Isolated as a yellow glass (0.106 g, 78%).

[0241] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-4-fluoro-N-(4-fluorophenyl)benzamide (F48) [ka] Isolated as a yellow foam (0.083 g, 59%).

[0242] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2,4-difluoro-N-(4-fluorophenyl)benzamide (F49) [ka] Isolated as a white solid (0.061 g, 45%).

[0243] trans-2-chloro-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1- Carboxamido)-N-(3-fluorophenyl)benzamide (F50) [ka] Isolated as a white solid (0.108 g, 83%).

[0244] trans-2-chloro-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-chlor Voxamido-N-(3-fluorophenyl)benzamide (F51) [ka] Isolated as a white solid (0.104 g, 76%).

[0245] trans-2-chloro-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1- Carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F52) [ka] Isolated as a white solid (0.113 g, 85%).

[0246] trans-2-chloro-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F53) [ka] Isolated as a white solid (0.094 g, 67%).

[0247] trans-2-chloro-N-(4-cyano-2-methylphenyl)-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)- (chlorophenyl)cyclopropane-1-carboxamido)benzamide (F54) [ka] Isolated as a white solid (0.085 g, 63%).

[0248] trans-2-chloro-N-(4-cyano-2-methylphenyl)-5-(2,2-dichloro-3-(3,4-dichloro)phenyl)- Phenyl)cyclopropane-1-carboxamido)benzamide (F55) [ka] Isolated as a white solid (0.088 g, 62%).

[0249] trans-2-chloro-5-(2,2-dichloro-3-(3-(trifluoromethyl)phenyl)cyclopropane) N-(4-fluorophenyl)benzamide (F56) [ka] Isolated as a white solid (0.120 g, 78%).

[0250] trans-2-chloro-5-(2,2-dichloro-3-(3-(trifluoromethyl)phenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F57) [ka] Isolated as a white solid (0.102 g, 61%).

[0251] trans-2-chloro-5-(2,2-dichloro-3-(3-(trifluoromethyl)phenyl)cyclopropane-1-carboxamido)-N-(2,6-difluorophenyl)benzamide (F58) [ka] Isolated as a white solid (0.066 g, 42%).

[0252] trans-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-(4-fluorophenyl)-N-methylbenzamide (F59) [ka] Isolated as a white solid (0.117 g, 86%).

[0253] trans-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-(4-fluorophenyl)-N-methylbenzamide (F60) [ka] Isolated as a white solid (0.027 g, 21%).

[0254] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(2,4-difluorophenyl)-2-fluorobenzamide (F61) [ka] Isolated as a white solid (0.120 g, 73%).

[0255] trans-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)-N-(2,4-difluorophenyl)-2-fluorobenzamide (F62) [ka] Isolated as a white solid (0.102 g, 62%).

[0256] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(2,4-difluorophenyl)-2-fluoro-N-methylbenzamide (F63) [ka] Isolated as a white solid (0.123 g, 73%).

[0257] trans-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamide )-N-(2,4-difluorophenyl)-2-fluoro-N-methylbenzamide (F64) [ka] Isolated as a white foam (0.110 g, 65%).

[0258] trans-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamido)-N-(2,4-difluorophenyl)-2-fluoro-N-methylbenzamide (F65) [ka] Isolated as a white solid (0.098 g, 55%).

[0259] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-methyl-N-phenylbenzamide (F66) [ka] Isolated as a white foam (0.123 g, 78%).

[0260] trans-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-methyl-N-phenylbenzamide (F67) [ka] Isolated as a white foam (0.124 g, 79%).

[0261] trans-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamide (mido)-2-fluoro-N-methyl-N-phenylbenzamide (F68) [ka] Isolated as a white solid (0.122 g, 72%).

[0262] trans-3-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-methyl-N-phenylbenzamide (F69) [ka] Isolated as a yellow foam (0.101 g, 64%).

[0263] trans-3-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-methyl-N-phenylbenzamide (F70) [ka] Isolated as a pale yellow foam (0.107 g, 68%).

[0264] trans-3-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-methyl-N-phenylbenzamide (F71) [ka] Isolated as a pale yellow foam (0.114 g, 68%).

[0265] trans-5-(3-(4-bromo-3,5-dichlorophenyl)-2,2-dichlorocyclopropane-1-chlor Voxamido)-2-chloro-N-(4-fluorophenyl)benzamide (F72) [ka] Isolated as a white solid (0.030 g, 22%).

[0266] trans-2-chloro-5-(2,2-dichloro-3-(2,4,5-trichlorophenyl)cyclopropane-1- Carboxamido)-N-(4-fluorophenyl)benzamide (F73) [ka] Isolated as a white solid (0.047 g, 32%).

[0267] trans-2-chloro-5-(2,2-dichloro-3-(2,4,5-trichlorophenyl)cyclopropane-1- Carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F74) [ka] Isolated as a white solid (0.109 g, 73%).

[0268] trans-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamide)-N-(2,4-difluorophenyl)-2-fluorobenzamide (F75) [ka] Isolated as a white solid (0.098 g, 56%).

[0269] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(5-fluoropyridin-2-yl)benzamide (F76) [ka] Isolated as a white solid (0.029 g, 23%).

[0270] trans-5-(2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)benzamido)-N-methylpicolinamide (F77) [ka] Isolated as a white solid (0.039 g, 25%).

[0271] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(pyridin-2-yl)benzamide (F78) [ka] Isolated as a white solid (0.071 g, 51%).

[0272] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-4-(trifluoromethoxy)phenyl) Cyclopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (F79) [ka] Isolated as a white solid (0.082 g, 57%).

[0273] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-4-(trifluoromethoxy)phenyl) Cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F80) [ka] Isolated as a white solid (0.111 g, 75%).

[0274] trans-2-chloro-5-(2,2-dichloro-3-(4-(trifluoromethyl)phenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (F81) [ka] Isolated as a white solid (0.123 g, 80%).

[0275] trans-2-chloro-5-(2,2-dichloro-3-(4-(trifluoromethyl)phenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F82) [ka] Isolated as a white solid (0.130 g, 82%).

[0276] trans-2-chloro-5-(2,2-dichloro-3-(4-(trifluoromethyl)phenyl)cyclopropane-1-carboxamido)-N-(2,6-difluorophenyl)benzamide (F83) [ka] Isolated as a white solid (0.082 g, 52%).

[0277] trans-5-(3-(3,5-bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamido)-2-chloro-N-(4-fluorophenyl)benzamide (F84) [ka] Isolated as a white solid (0.042 g, 30%).

[0278] trans-5-(3-(3,5-bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamido)-2-chloro-N-(4-fluorophenyl)-N-methylbenzamide (F85) [ka] Isolated as a white solid (0.092 g, 64%).

[0279] trans-5-(3-(3,5-bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamido)-2-chloro-N-(2,6-difluorophenyl)benzamide (F86) [ka] Isolated as a white solid (0.038 g, 26%).

[0280] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-5-(trifluoromethyl)phenyl)phenyl) Chlopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (F87) [ka] Isolated as a white solid (0.055 g, 38%).

[0281] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-5-(trifluoromethyl)phenyl)phenyl) Chlopropane-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F88 ) [ka] Isolated as a white solid (0.095 g, 63%).

[0282] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-5-(trifluoromethyl)phenyl)phenyl) Chlopropane-1-carboxamido)-N-(2,6-difluorophenyl)benzamide (F89) [ka] Isolated as a white solid (0.032 g, 21%).

[0283] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dibromophenyl)cyclopropane-1-chlor Voxamido-N-(4-fluorophenyl)benzamide (F90) [ka] Isolated as a white solid (0.023 g, 16%).

[0284] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dibromophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F91) [ka] Isolated as a white solid (0.066 g, 47%).

[0285] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dibromophenyl)cyclopropane-1-chlor Voxamido)-N-(2,6-difluorophenyl)benzamide (F92) [ka] Isolated as a white solid (0.020 g, 14%).

[0286] trans-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluorobenzamide (F93) [ka] Isolated as a white solid (0.108 g, 78%).

[0287] trans-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluorobenzamide (F94) [ka] Isolated as a white solid (0.122 g, 88%).

[0288] trans-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamido)-2-fluorobenzamide (F95) [ka] Isolated as a white solid (0.013 g, 10%).

[0289] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichloro-4-fluorophenyl)cyclopropane) Pan-1-carboxamido)-N-(4-fluorophenyl)benzamide (F96) [ka] Isolated as a white solid (0.017 g, 11%).

[0290] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichloro-4-fluorophenyl)cyclopropane) Pan-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F97) [ka] Isolated as a white solid (0.063 g, 41%).

[0291] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichloro-4-fluorophenyl)cyclopropane) Pan-1-carboxamido)-N-(2,6-difluorophenyl)benzamide (F98) [ka] Isolated as a white solid (0.025 g, 16%).

[0292] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-ethyl-N-(4-fluorophenyl)benzamide (F99) [ka] Isolated as a white solid (0.087 g, 60%).

[0293] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)-N-(2,2,2-trifluoroethyl)benzamide (F100) [ka] Isolated as a white solid (0.095 g, 60%).

[0294] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)-N-propylbenzamide (F101) [ka] Isolated as a yellow foam (0.090 g, 61%).

[0295] trans-N-allyl-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane) N-(4-fluorophenyl)benzamide (F102) [ka] Isolated as an orange foam (0.047 g, 32%).

[0296] trans-2-chloro-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,4-dichloro)phenyl)- (phenyl)cyclopropane-1-carboxamido)benzamide (F103) [ka] Isolated as a colorless oil (0.032 g, 22%).

[0297] trans-2-chloro-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)-trans Chlorophenyl)cyclopropane-1-carboxamido)benzamide (F104) [ka] Isolated as a white foam (0.016 g, 11%).

[0298] trans-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-methylbenzamide (F105) [ka] Isolated as a white foam (0.020 g, 20%).

[0299] trans-2-chloro-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,5-dichloro) (triphenyl)cyclopropane-1-carboxamido)-N-methylbenzamide (F106) [ka] Isolated as a colorless oil (0.041 g, 28%).

[0300] trans-2-chloro-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,4-dichloro)phenyl)- (triphenyl)cyclopropane-1-carboxamido)-N-methylbenzamide (F107) [ka] Isolated as a white foam (0.034 g, 23%).

[0301] trans-2-chloro-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)-trans Chlorophenyl)cyclopropane-1-carboxamido)-N-methylbenzamide (F108) [ka] Isolated as a colorless oil (0.039 g, 25%).

[0302] trans-2-chloro-5-(2,2-dichloro-3-phenylcyclopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (F109) [ka] Isolated as a yellow film (0.011 g, 6%).

[0303] trans-2-chloro-5-(2,2-dichloro-3-phenylcyclopropane-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F110) [ka] Isolated as a yellow solid (0.044 g, 25%).

[0304] trans-2-chloro-5-(2,2-dichloro-3-phenylcyclopropane-1-carboxamido)-N-(2,6-difluorophenyl)benzamide (F111) [ka] Isolated as a yellow film (0.011 g, 6%).

[0305] trans-2,2-dichloro-N-(4-chloro-3-((4-fluorophenyl)(methyl)carbamothione (phenyl)-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide (F112) [ka] Isolated as a yellow solid (0.024 g, 25%).

[0306] trans-2,2-dichloro-N-(4-chloro-3-((4-fluorophenyl)carbamothioyl)phenyl)-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide (F113) [ka] Isolated as a yellow solid (0.027 g, 13%).

[0307] trans-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-methylbenzamide (F114) [ka] Isolated as a colorless glass (0.004 g, 4%).

[0308] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-(methylthio)benzamide (F115) [ka] Isolated as a white solid (0.173 g, 28%).

[0309] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-5-methylphenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (F116) [ka] Isolated as a white solid (0.083 g, 59%).

[0310] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-5-methylphenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (F117) [ka] Isolated as a white foam (0.100 g, 69%).

[0311] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-5-methylphenyl)cyclopropane-1-carboxamido)-N-(2,6-difluorophenyl)benzamide (F118) [ka] Isolated as a white foam (0.066 g, 45%).

[0312] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichloro-4-methylphenyl)cyclopropane N-(4-fluorophenyl)benzamide (F119) [ka] Isolated as a white foam (0.028 g, 21%).

[0313] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichloro-4-methylphenyl)cyclopropane N-(4-fluorophenyl)-N-methylbenzamide (F120) [ka] Isolated as a white solid (0.077 g, 56%).

[0314] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichloro-4-methylphenyl)cyclopropane N-(2,6-difluorophenyl)benzamide (F121) [ka] Isolated as a white foam (0.025 g, 18%).

[0315] trans-2-chloro-5-(2,2-dibromo-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)benzamide (F122) [ka] Isolated as an off-white solid (0.075 g, 45%).

[0316] trans-2-chloro-5-(2,2-dichloro-3-(3,4-dichloro-5-methylphenyl)cyclopropane N-(4-fluorophenyl)benzamide (F123) [ka] Isolated as a white foam (0.102 g, 76%).

[0317] trans-2-chloro-5-(2,2-dichloro-3-(3,4-dichloro-5-methylphenyl)cyclopropane N-(4-fluorophenyl)-N-methylbenzamide (F124) [ka] Isolated as a white foam (0.071 g, 52%).

[0318] trans-2-chloro-5-(2,2-dichloro-3-(3,4-dichloro-5-methylphenyl)cyclopropane N-(2,6-difluorophenyl)benzamide (F125) [ka] Isolated as a white foam (0.094 g, 68%).

[0319] Example 14: Preparation of trans-4-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)picolinamide (F126) [ka] To a solution of trans-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarboxylic acid (C1) (0.100 g, 0.333 mmol) in dichloromethane (3.33 mL) at 0 °C, N,N-dimethylformamide was added. The amide (1 drop) and oxalyl chloride (0.0440 mL, 0.500 mmol) were added dropwise. The cold bath was removed and the reaction was stirred at room temperature for 1 hour. The reaction was cooled again to 0°C and N-methylmorpholine (0.110 mL, 1.000 mmol) was added followed by 4-amino-N-(4-fluorophenyl)picolinamide (C81) (0.154 g, 0.667 mmol). The reaction was stirred at room temperature for 1 hour. The reaction was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate (2x) and hydrochloric acid (1 N) (2 The organic phase was dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography using 0% to 100% ethyl acetate / hexanes as eluent afforded the title compound as a clear glassy solid (0.0800 g, 44%). The following compounds were prepared in a manner similar to the procedure outlined in Example 14:

[0320] trans-2-chloro-3-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)benzamide (F127) [ka] Isolated as a white solid (0.102 g, 67%).

[0321] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-methoxybenzamide (F128) [ka] Isolated as a white solid (0.040 g, 26%).

[0322] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-fluoro-N-(4-fluorophenyl)benzamide (F129) [ka] Isolated as a white solid (0.081 g, 58%).

[0323] trans-4-chloro-3-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)benzamide (F130) [ka] Isolated as an off-white solid (0.099 g, 65%).

[0324] trans-3-chloro-6-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido-N-(4-fluorophenyl)picolinamide (F131) [ka] Isolated as a pale yellow solid (0.116 g, 75%).

[0325] trans-2-cyano-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide Voxamido)-N-(4-fluorophenyl)benzamide (F132) [ka] Isolated as a yellow film (0.043 g, 38%).

[0326] trans-6-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)picolinamide (F133) [ka] Isolated as a clear glassy solid (0.033 g, 40%).

[0327] trans-3-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-4-methylbenzamide (F134) [ka] Isolated as an off-white solid (0.039 g, 35%).

[0328] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-(trifluoromethoxy)benzamide (F135) [ka] Isolated as a white solid (0.108 g, 65%).

[0329] trans-3-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)benzamide (F136) [ka] Isolated as a clear glassy solid (0.078 g, 51%).

[0330] Example 15: Preparation of trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-nitrophenyl)benzamide (F137) [ka] To a solution of 4-nitroaniline (0.0270 g, 0.198 mmol) in dichloromethane (2 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.0480 g, 0.248 mmol), 4-dimethylaminopyridine (0.0240 g, 0.198 mmol), and trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarboxamido)benzoic acid (C67) (0.0750 g, 0.165 mmol) sequentially. The reaction was stirred at room temperature for 16 hours. The reaction was filtered and the eluate was filtered off. The eluate was then filtered and the eluate was then ... The column was loaded onto a column (registered trademark) and flash-filtered using 0% to 25% ethyl acetate / hexanes as the eluent. Purification by column chromatography gave the title compound as a yellow solid (0.0131 g, 14%). The following compounds were prepared in a manner similar to the procedure outlined in Example 15:

[0331] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(1,2,3-thiadiazol-5-yl)benzamide (F138) [ka] Isolated as a white solid (0.024 g, 27%).

[0332] Example 16: trans-3-(2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane)-2-yl)cyclopropane Preparation of propane-1-carboxamido)benzamido)pyridine 1-oxide (F139) [ka] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxylate To a solution of N-(pyridin-3-yl)benzamide (F27) (0.0930 g, 0.176 mmol) in dichloromethane (4 mL) was added meta-chloroperbenzoic acid (0.0404 g, 0.176 mmol). The reaction was stirred at room temperature for 14 hours. Celite® was added to the reaction and the solvent was concentrated. The residue was purified by flash column chromatography using 0% to 10% methanol / dichloromethane as the eluent. Purification by chromatography gave the title compound as a white solid (0.0813 g, 85%). Got it. The following compounds were prepared in a manner similar to the procedure outlined in Example 16:

[0333] trans-4-(2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)benzamide)pyridine 1-oxide (F140) [ka] Isolated as a white solid (0.035 g, 34%).

[0334] trans-4-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-2-((4-fluorophenyl)carbamoyl)pyridine 1-oxide (F141) [ka] Isolated as a pale yellow solid (0.038 g, 58%).

[0335] Example 17: Preparation of trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(6-fluoropyridin-3-yl)benzamide (F142) [ka] 6-Fluoropyridin-3-amine (0.0290 g, 0.254 mmol) in dichloromethane (2 mL) The solution was cooled in an ice bath. Triethylamine (0.0440 mL, 0.318 mmol) was added. trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)benzoyl chloride (C68) (0.100 g, 0.212 mmol) was dissolved in dichloromethane (2 mL) and the solution was added to the reaction mixture. The ice bath was removed and the reaction was stirred at room temperature overnight. The reaction was loaded onto Celite® and washed with 0% to 40% ethyl acetate / hexanes. Purification by flash column chromatography using hexanes as eluent afforded the title compound as a white solid (0.0339 g, 29%). The following compounds were prepared in a manner similar to the procedure outlined in Example 17:

[0336] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-(methylsulfonyl)phenyl)benzamide (F143) [ka] Isolated as a white solid (0.040 g, 30%).

[0337] trans-2-chloro-N-(4-cyano-2-fluorophenyl)-5-(2,2-dichloro-3-(3,5-dichloro) (phenyl)cyclopropane-1-carboxamido)benzamide (F144) [ka] Isolated as a white solid (0.028 g, 23%).

[0338] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(oxazol-2-yl)benzamide (F145) [ka] Isolated as a light brown solid (0.021 g, 19%).

[0339] Example 18: Preparation of trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-methoxyphenyl)benzamide (F146) [ka] A solution of trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarboxamido)benzoic acid (C67) (0.100 g, 0.212 mmol) in dichloromethane (0.1 mL) N,N-dimethylformamide (1 drop) was added and the reaction was cooled in an ice bath. Oxalyl chloride (0.0438 mL, 0.254 mmol) was added slowly over approximately 5 minutes. The reaction was removed from the ice bath and cooled. The reaction mixture was then allowed to warm to room temperature over 90 minutes. The reaction mixture was then concentrated. The residue was redissolved in dichloromethane (0.1 mL). This solution was added to a cooled (ice bath) separate dichloromethane of 4-methoxyaniline (0.0310 g, 0.254 mmol) and triethylamine (0.0440 mL, 0.318 mmol). The reaction mixture was added to a solution of methane (0.5 mL). The reaction mixture was removed from the ice bath and stirred at room temperature for 14 hours. The reaction mixture was adsorbed directly onto Celite® and purified by flash column chromatography using ethyl acetate / hexanes as the eluent, followed by trituration with dichloromethane / hexanes to give the title compound as a white solid (0.0666 g, 56%). The following compounds were prepared in a manner similar to the procedure outlined in Example 18:

[0340] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-(trifluoromethoxy)phenyl)benzamide (F147) [ka] Isolated as a yellow solid (0.078 g, 60%).

[0341] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-(difluoromethoxy)phenyl)benzamide (F148) [ka] Isolated as a light brown solid (0.089 g, 70%).

[0342] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-(methylthio)phenyl)benzamide (F149) [ka] Isolated as a light brown solid (0.068 g, 56%).

[0343] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2-fluoro-4-methoxyphenyl)benzamide (F150) [ka] Isolated as a beige solid (0.060 g, 49%).

[0344] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2-fluoro-4-methylphenyl)benzamide (F151) [ka] Isolated as a white solid (0.057 g, 48%).

[0345] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-(methylcarbamoyl)phenyl)benzamide (F152) [ka] Isolated as a white solid (0.062 g, 50%).

[0346] trans-N-(4-acetamidophenyl)-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)benzamide (F153) [ka] Isolated as a white solid (0.096 g, 77%).

[0347] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(3,5-difluorophenyl)benzamide (F154) [ka] Isolated as a white solid (0.044 g, 37%).

[0348] trans-2,2-dichloro-N-(4-chloro-3-(5-fluoroindoline-1-carbonyl)phenyl)-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide (F155) [ka] Isolated as a white foam (0.052 g, 41%).

[0349] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2-fluoropyridin-3-yl)benzamide (F156) [ka] Isolated as a white solid (0.058 g, 48%).

[0350] Example 19: Preparation of trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-(methylsulfonyl)benzamide (F157) Made [ka] To a solution of trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-(methylthio)benzamide (F115) (0.049 g, 0.088 mmol) in dichloromethane (0.878 mL) was added meta-chloroperbenzoic acid (0.049 g, 0.22 mmol). The reaction was stirred at room temperature for 3 hours. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over magnesium sulfate, filtered, and concentrated. Fractional distillation was performed using 0% to 15% methanol / dichloromethane as eluent. Purification by wash column chromatography gave the title compound as a white solid (0.042 g, 73%).

[0351] Example 20: trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-(methylsulfinyl)benzamide (F158) preparation [ka] To a solution of trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-2-(methylthio)benzamide (F115) (0.051 g, 0.091 mmol) in dichloromethane (0.9 mL) was added meta-chloroperbenzoic acid (0.021 g, 0.096 mmol). The reaction was stirred at room temperature for 1 hour. Saturated aqueous sodium bicarbonate was added and the mixture was stirred. The residue was extracted with ethyl acetate. The combined organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by wash column chromatography gave the title compound as a white solid (0.036 g, 65%). The following compounds were prepared in a manner similar to the procedure outlined in Example 20:

[0352] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-(methylsulfinyl)phenyl)benzamide (F159) [ka] Isolated as a white solid (0.013 g, 24%).

[0353] Example 21: Preparation of trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)benzoyl chloride (C68) [ka] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclohexyl)-2 ... Isopropylcarboxamidobenzoic acid (C67) (0.200 g, 0.441 mmol) in dichloromethane To a solution of 2.2 mL of N,N-dimethylformamide (1 drop) was added, followed by the addition of oxalyl chloride (0.0579 mL, 0.661 mmol) over 2 minutes. The ice batch was removed and the reaction was allowed to warm to room temperature over 90 minutes. The reaction was then concentrated to give the title compound as a cream-colored foam (0.211 g, quant), which was used without further purification or characterization.

[0354] Example 22: 5-amino-2-chloro-N-(4-fluorophenyl)benzamide (C69) and 3-amino- Preparation of N-(4-fluorophenyl)benzamide (C70) [ka] Palladium on alumina (5%, 0.0065 g, 0.061 mmol) was dissolved in 2-chloro-N-(4-fluorophenyl)-5-nitrobenzamide (C143) (0.18 g, 0.61 mmol) and ethyl acetate (6 mL) to prepare a solubility-enriched ... The mixture was purged with nitrogen and the reaction was stirred under a hydrogen balloon at room temperature for 3 min. Palladium on carbon (10%, 0.0070 g) was added and the reaction was heated under a hydrogen balloon. The reaction was stirred overnight. The reaction was diluted with dichloromethane and washed with hydrochloric acid (1 N). The aqueous layer was saturated. Neutralize with aqueous sodium bicarbonate and extract with dichloromethane to give (C69) as a yellow oil. The compound (0.028 g, 16%) was obtained as: 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.65 - 7.51 (m, 2H), 7.17 (d, J = 8.6 Hz, 1H), 7.08 - 7.00 (m, 3H), 6.68 (dd, J = 8.6, 2.9 Hz, 1H), 3.85 (s, 2H);IR (thin film) 3349, 1654 cm -1 ESIMS m / z 265 ([M+H] + The organic layer was concentrated to give a yellow solid that was suspended in degassed methanol (6 mL). Palladium on carbon (10%, 0.010 g) was added and the reaction was stirred overnight under a hydrogen balloon. The reaction was diluted with ethyl acetate and extracted with hydrochloric acid (1 N). The aqueous layer was made basic with saturated aqueous sodium bicarbonate. The resulting solution was extracted with dichloromethane and concentrated to give (C70) as a yellow solid (0.060 g, 38%). And got: 1 H NMR (400 MHz, CDCl3) δ 7.85 (s, 1H), 7.58 (dd, J = 9.0, 4.8 Hz, 2H), 7.25 - 7.20 (m, 1H), 7.20 - 7.15 (m, 1H), 7.04 (t, J = 8.7 Hz, 2H), 6.83 (ddd, J = 7.9, 2.4, 0.9 Hz, 1H), 3.83 (s, 2H);IR (thin film) 3328, 1648 cm -1 ESIMS m / z 231 ([M+H] + ).

[0355] Example 23: Preparation of 5-amino-2-chloro-N-(4-fluorophenyl)benzamide (C69) [ka] To a solution of 2-chloro-N-(4-fluorophenyl)-5-nitrobenzamide (C143) (3.57 g, 12.1 mmol) in methanol (81 mL) and water (40.4 mL) was added iron powder (3.38 g, 60.6 mmol) and ammonium chloride (1.94 g, 36.3 mmol). The reaction was heated at 60° C. for 2 hours. The reaction was filtered through Celite®. The filtrate was diluted with ethyl acetate and washed with brine. The organic phase was extracted with hydrochloric acid (1 N). The combined aqueous phase was washed with saturated aqueous sodium bicarbonate. The mixture was neutralized with HCl and extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated to give the title compound as a white solid (1.75 g, 54%). The following compounds were prepared in a manner similar to the procedure outlined in Example 23:

[0356] 5-Amino-N-(4-fluorophenyl)-2-(trifluoromethyl)benzamide (C71) [ka] Isolated as a brown solid (0.182 g, 63%): 1 H NMR (400 MHz, DMSO-d6) δ 10.47 EIMS m / z 298 ([M] + ).

[0357] 5-Amino-N-(4-fluorophenyl)-2-iodobenzamide (C72) [ka] Isolated as a brown solid (0.205 g, 84%): 1 H NMR (400 MHz, DMSO-d6) δ 10.34 (s, 1H), 7.78 - 7.66 (m, 2H), 7.45 (d, J = 8.5 Hz, 1H), 7.24 - 7.10 (m, 2H), 6.67 (d, J = 2.7 Hz, 1H), 6.45 (dd, J = 8.5, 2.7 Hz, 1H), 5.50 (s, 2H);IR (thin film) 3247, 1650 cm -1 ESIMS m / z 357 ([M+H] + ).

[0358] 5-Amino-2-chloro-N-(4-cyanophenyl)benzamide (C73) [ka] Isolated as a yellow solid (0.119 g, 52%): 1 H NMR (400 MHz, DMSO-d6) δ 10.83 (s, 1H), 7.90 (d, J = 8.7 Hz, 2H), 7.81 (d, J = 8.8 Hz, 2H), 7.15 (d, J = 8.6 Hz, 1H), 6.71 (d, J = 2.7 Hz, 1H), 6.67 (dd, J = 8.6, 2.7 Hz, 1H), 5.51 (s, 2H);IR (thin film) 3365, 3100, 2223, 1670 cm -1 ESIMS m / z 273 ([M+H] + ).

[0359] 5-Amino-2-chloro-N-(4-(trifluoromethyl)phenyl)benzamide (C74) [ka] Isolated as a yellow solid (0.253 g, 79%): 1 H NMR (400 MHz, DMSO-d6) δ 10.76 (s, 1H), 7.93 (d, J = 8.5 Hz, 2H), 7.72 (d, J = 8.6 Hz, 2H), 7.15 (d, J = 8.6 Hz, 1H), 6.72 (d, J = 2.7 Hz, 1H), 6.67 (dd, J = 8.6, 2.7 Hz, 1H), 5.51 (s, 2H);IR (thin film) 3230, 3039, 1666 cm -1 ESIMS m / z 316 ([M+H] + ).

[0360] 5-Amino-2-chloro-N-(4-chlorophenyl)benzamide (C75) [ka] Isolated as a yellow solid (0.290 g, 90%): 1 H NMR (400 MHz, DMSO-d6) δ 10.51 (s, 1H), 7.80 - 7.68 (m, 2H), 7.44 - 7.32 (m, 2H), 7.13 (d, J = 8.6 Hz, 1H), 6.69 (d, J = 2.7 Hz, 1H), 6.65 (dd, J = 8.6, 2.8 Hz, 1H), 5.48 (s, 2H);IR (thin film) 3375, 3212, 1660 cm -1 ESIMS m / z 282 ([M+H] + ).

[0361] 5-amino-2-chloro-N-(2-chloro-4-fluorophenyl)benzamide (C76) [ka] Isolated as a white solid (0.092 g, 68%): IR (thin film) 3377, 3157, 1659 cm -1 ESIMS m / z 300 ([M+H] + ).

[0362] 5-Amino-2-chloro-N-(4-chlorophenyl)benzamide (C77) [ka] Isolated as a red solid (0.185 g, 84%): 1 H NMR (400 MHz, DMSO-d6) δ 9.82 (s, 1H), 7.35 (d, J = 7.5 Hz, 1H), 7.26 - 7.10 (m, 4H), 6.75 (d, J = 2.7 Hz, 1H), 6.63 (dd, J = 8.6, 2.7 Hz, 1H), 5.46 (s, 2H), 2.27 (s, 3H);IR (thin film) 3351, 3228, 1654 cm -1 ESIMS m / z 262 ([M+H] + ).

[0363] 5-Amino-N-(4-fluorophenyl)-2-methylbenzamide (C78) [ka] Isolated as a brown solid (0.390 g, 83%): 1 H NMR (400 MHz, DMSO-d6) δ 10.23 (s, 1H), 7.82 - 7.68 (m, 2H), 7.23 - 7.08 (m, 2H), 6.92 (d, J = 8.2 Hz, 1H), 6.65 (d, J = 2.4 Hz, 1H), 6.58 (dd, J = 8.1, 2.4 Hz, 1H), 5.07 (s, 2H), 2.18 (s, 3H);IR (thin film) 3422, 3339, 3256, 1649 cm -1 ESIMS m / z 245 ([M+H] + ).

[0364] 5-Amino-2-bromo-N-(4-fluorophenyl)benzamide (C79) [ka] Isolated as a brown solid (0.308 g, 87%): 1 H NMR (400 MHz, DMSO-d6) δ 10.40 (s, 1H), 7.76 - 7.66 (m, 2H), 7.26 (d, J = 8.6 Hz, 1H), 7.21 - 7.11 (m, 2H), 6. 68 (d, J = 2.7 Hz, 1H), 6.58 (dd, J = 8.6, 2.8 Hz, 1H), 5.50 (s, 2H);IR (thin film) 3382, 3236, 1645 cm -1 ESIMS m / z 310 ([M+H] + ).

[0365] 5-amino-N-(4-fluorophenyl)-2-(1H-1,2,4-triazol-1-yl)benzamide (C80) [ka] Isolated as a beige solid (0.182 g, 54%): 1 H NMR (400 MHz, DMSO-d6) δ 10.32 (s, 1H), 8.63 (s, 1H), 7.99 (s, 1H), 7.59 7.51 (m, 2H), 7.24 (d, J = 8.5 Hz, 1H), 7.15 - 7.08 (m, 2H), 6.81 (d, J = 2.5 Hz, 1H), 6.74 (dd, J = 8.5, 2.5 Hz, 1H), 5.75 (s, 2H);IR (thin film) 3344, 3227, 3051, 1659 cm -1 ESIMS m / z 298 ([M+H] + ).

[0366] 4-Amino-N-(4-fluorophenyl)picolinamide (C81) [ka] Isolated as a brown solid (0.321 g, 57%): 1 H NMR (400 MHz, DMSO-d6) δ 10.53 (s, 1H), 8.11 (d, J = 5.5 Hz, 1H), 7.91 (dd, J = 9.0, 5.0 Hz, 2H), 7.32 (d, J = 2.1 Hz, 1H), 7.18 (t, J = 8.9 Hz, 2H), 6.66 (dd, J = 5.5, 2.2 Hz, 1H), 6.44 (s, 2H);IR (thin film) 3484, 3359, 3321, 3234, 1642 cm -1 ESIMS m / z 232 ([M+H] + ).

[0367] 3-Amino-2-chloro-N-(4-fluorophenyl)benzamide (C82) [ka] Isolated as a yellow solid (0.332 g, 65%): 1 H NMR (400 MHz, DMSO-d6) δ 10.42 (s, 1H), 7.81 - 7.65 (m, 2H), 7.25 7.13 (m, 2H), 7.10 (t, J = 7.7 Hz, 1H), 6.88 (dd, J = 8.1, 1.3 Hz, 1H), 6.67 (dd, J = 7.3, 1.3 Hz, 1H), 5.57 (s, 2H);IR (thin film) 3372, 3237, 3011, 1655 cm -1 ESIMS m / z 265 ([M+H] + ).

[0368] 5-Amino-N-(4-fluorophenyl)-2-methoxybenzamide (C83) [ka] Isolated as a light brown solid (0.356 g, 61%): 1 H NMR (400 MHz, DMSO-d6) δ 10.12 (s, 1H), 7.80 - 7.69 (m, 2H), 7.21 7.11 (m, 2H), 6.96 (d, J = 2.9 Hz, 1H), 6.90 (d, J = 8.8 Hz, 1H), 6.71 (dd, J = 8.7, 2.9 Hz, 1H), 4.89 (s, 2H), 3.79 (s, 3H);IR (thin film) 3338, 1662 cm -1 ESIMS m / z 261 ([M+H] + ).

[0369] 5-Amino-2-chloro-N-phenylbenzamide (C84) [ka] Isolated as a white foam (1.28 g, 96%): 1 H NMR (400 MHz, CDCl3) δ 7.97 (s, 1H), 7.68 - 7.60 (m, 2H), 7.43 - 7.34 (m, 2H), 7.22 - 7.13 (m, 2H), 7.10 (d, J = 2.9 Hz, 1H), 6.71 (dd, J = 8.5, 2.9 Hz, 1H), 3.83 (s, 2H); 13 C NMR (101 MHz, CDCl3) δ 164.43, 145.71, 137.61, 135.33, 131.12, 129.12, 124.77, 120.12, 118.92, 118.22, 116.55;ESIMS m / z 247 ([M+H] + ).

[0370] 5-Amino-2-chloro-N-(2-fluorophenyl)benzamide (C85) [ka] Isolated as a white solid (1.24 g, quant): 1 H NMR (400 MHz, CDCl3) δ 8.48 (td, J = 8.1, 1.6 Hz, 1H), 8.34 (s, 1H), 7.23 - 7.08 (m, 5H), 6.72 (dd, J= 8.5, 2.9 Hz, 1H), 3.85 (s, 2H), 3.48 (s, 1H); 19 F NMR (376 MHz, CDCl3) δ -130.65;ESIMS m / z 265 ([M+H] + ).

[0371] 5-Amino-2-chloro-N-(2,4-difluorophenyl)benzamide (C86) [ka] Isolated as a purple solid (0.37 g, 28%): 1 H NMR (400 MHz, CDCl3) δ 8.42 (tdd, J = 9.7, 6.0, 3.6 Hz, 1H), 8.25 (s, 1H), 7.21 (d, J = 8.5 Hz, 1H), 7.13 (d, J = 2.9 Hz, 1H), 6.97 - 6.88 (m, 2H), 6.73 (dd, J = 8.5, 2.9 Hz, 1H), 3.84 (s, 2H); 19 F NMR (376 MHz, CDCl3) δ -114.57 (d, J = 4.6 Hz), -125.78 (d, J = 4.6 Hz) ESIMS m / z 283 ([M+H] + ).

[0372] 5-Amino-2-chloro-N-(4-fluorophenyl)-N-methylbenzamide (C87) [ka] Isolated as a white solid (0.81 g, 60%): 1H NMR (400 MHz, CDCl3) δ 7.17 - 7.07 (m, 2H), 6.96 - 6.83 (m, 3H), 6.49 - 6.40 (m, 2H), 3.60 (s, 2H), 3.45 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -114.12;ESIMS m / z279 ([M+H] + ).

[0373] 5-Amino-2-chloro-N-(3-fluorophenyl)benzamide (C88) [ka] Isolated as a white solid (1.18 g, 95%): 1 H NMR (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.63 (dt, J = 10.9, 2.2 Hz, 1H), 7.31 (td, J = 8.1, 6.2 Hz, 1H), 7.26 - 7.22 (m, 1H), 7.20 (d, J = 8.5 Hz, 1H), 7.09 (d, J = 3.0 Hz, 1H), 6.86 (tdd, J = 8.3, 2.5, 1.1 Hz, 1H), 6.71 (dd, J = 8.6, 2.9 Hz, 1H), 3.84 (s, 2H); 19 F NMR (376 MHz, CDCl3) δ -111.22;ESIMS m / z 265 ([M+H] + ).

[0374] 5-Amino-2-chloro-N-(3-cyanophenyl)benzamide (C89) [ka] Isolated as a white solid (0.89 g, 70%): 1 H NMR (400 MHz, DMSO-d6) δ 10.75 (s, 1H), 8.23 ​​- 8.14 (m, 1H), 7.95 (td, J = 4.7, 2.2 Hz, 1H), 7.66 - 7.50 (m, 2H), 7.15 (d, J = 8.6 Hz, 1H), 6.76 - 6.60 (m, 2H), 5.52 (s, 2H); 13 C NMR (101 MHz, DMSO-d6) δ 165.98, 147.85, 139.77, 136.41, 130.29, 129.99, 127.17, 123.96, 121.98, 118.63, 116.18, 115.03, 113.32, 111.60;ESIMS m / z 272 ([M+H] + ).

[0375] 5-Amino-2-chloro-N-(2,3-difluorophenyl)benzamide (C90) [ka] Isolated as a white solid (1.11 g, 99%): 1 H NMR (400 MHz, CDCl3) δ 8.38 (s, 1H), 8.29 - 8.20 (m, 1H), 7.22 (d, J = 8.6 Hz, 1H), 7.17 - 7.06 (m, 2H), 6.95 (dddd, J= 9.9, 8.6, 7.6, 1.5 Hz, 1H), 6.73 (dd, J= 8.6, 2.9 Hz, 1H), 3.85 (s, 2H); 19 F NMR (376 MHz, CDCl3) δ -137.88 (d, J = 20.5 Hz), -154.65 (d, J = 20.4 Hz);ESIMS m / z 283 ([M+H] + ).

[0376] 5-Amino-2-chloro-N-(3,4-difluorophenyl)benzamide (C91) [ka] Isolated as a grey solid (1.26 g, 93%): 1 H NMR (400 MHz, CDCl3) δ 8.03 (s, 1H), 7.76 (ddd, J = 12.1, 7.2, 2.3 Hz, 1H), 7.23 - 7.08 (m, 4H), 6.72 (dd, J = 8.6, 2.9 Hz, 1H), 3.85 (s, 2H); 19 F NMR (376 MHz, CDCl3) δ -135.39 (d, J = 21.6 Hz), -141.93 (d, J = 21.7 Hz);ESIMS m / z 283 ([M+H] + ).

[0377] 5-Amino-2-chloro-N-(2,4,6-trifluorophenyl)benzamide (C92) [ka] Isolated as a light brown solid (1.20 g, 73%): 1 H NMR (400 MHz, DMSO-d6) δ 10.08 (s, 1H), 7.38 - 7.27 (m, 2H), 7.14 (d, J = 8.6 Hz, 1H), 6.74 (d, J= 2.7 Hz, 1H), 6.65 (dd, J = 8.6, 2.8 Hz, 1H), 5.52 (s, 2H); 19 F NMR (376 MHz, DMSO-d6) δ -109.56 (t, J = 5.5 Hz), -114.48 (d, J = 5.5 Hz);ESIMS m / z 301 ([M+H] + ).

[0378] 5-Amino-2-chloro-N-(2,6-difluorophenyl)benzamide (C93) [ka] Isolated as a light brown solid (0.93 g, 98%): 1H NMR (400 MHz, DMSO-d6) δ 10.09 (s, 1H), 7.40 (tt, J = 8.4, 6.3 Hz, 1H), 7.26 - 7.10 (m, 3H), 6.75 (d, J = 2.7 Hz, 1H), 6.65 (dd, J = 8.6, 2.8 Hz, 1H), 5.51 (s, 2H); 19 F NMR (376 MHz, DMSO-d6) δ -117.62;ESIMS m / z283 ([M+H] + ).

[0379] 3-amino-4-chloro-N-(4-fluorophenyl)benzamide (C94) [ka] Isolated as a white solid (0.147 g, 23%): 1 H NMR (400 MHz, DMSO-d6) δ 10.21 IR (thin film) 3472, 3379, 1659 cm -1 ESIMS m / z 265 ([M+H] + ).

[0380] 5-Amino-2-chloro-N-(pyridin-4-yl)benzamide (C95) [ka] Isolated as a yellow solid (0.385 g, 89%): 1H NMR (400 MHz, CD3OD) δ 8.44 (dt, J = 5.0, 1.3 Hz, 2H), 7.78 - 7.71 (m, 2H), 7.17 (dd, J = 8.6, 1.2 Hz, 1H), 6.83 (dd, J = 2.8, 1.1 Hz, 1H), 6.77 (ddd, J = 8.6, 2.8, 1.1 Hz, 1H); 13 C NMR (101 MHz, CDCl3) δ 171.98, 153.55, 153.30, 151.33, 150.57, 140.02, 134.02, 121.26, 117.90;ESIMS m / z 248 ([M+H] + ).

[0381] 5-Amino-2-chloro-N-(pyridin-3-yl)benzamide (C96) [ka] Isolated as a yellow solid (0.341 g, 80%): 1 H NMR (400 MHz, CD3OD) δ 8.82 (d , J = 2.5 Hz, 1H), 8.31 (dt, J = 4.9, 1.2 Hz, 1H), 8.23 ​​(ddt, J = 8.4, 2.6, 1.2 Hz, 1H), 7.45 (dd, J = 8.4, 4.9 Hz, 1H), 7.17 (dd, J = 8.6, 1.0 Hz, 1H), 6.85 (dd, J = 2.7, 1.0 Hz, 1H), 6.77 (ddd, J = 8.7, 2.8, 1.0 Hz, 1H); 13 C NMR (126 MHz, CD3OD) δ 167.78, 147.36, 144.18, 140.67, 136.19, 135.99, 130.06, 127.82, 123.97, 117.41, 117.22, 114.04;ESIMS m / z 248 ([M+H] + ).

[0382] 3-Amino-N-(4-fluorophenyl)-2-methoxybenzamide (C97) [ka] Isolated as a yellow oil (0.541 g, quant): 1 H NMR (400 MHz, CDCl3) δ 9.61 (s, 1H), 7.69 - 7.61 (m, 2H), 7.50 (dd, J = 7.8, 1.6 Hz, 1H), 7.13 - 7.02 (m, 3H), 6.92 (dd, J= 7.8, 1.6 Hz, 1H), 3.93 (s, 2H), 3.87 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -118.16;ESIMS m / z 261 ([M+H] + ).

[0383] 5-Amino-2-chloro-N-(2-chloropyridin-3-yl)benzamide (C98) [ka] Isolated as a yellow solid (0.269 g, 83%): 1 H NMR (400 MHz, DMSO-d6) δ 10.25 (s, 1H), 8.30 (dd, J = 4.7, 1.8 Hz, 1H), 8.09 (d, J = 8.1 Hz, 1H), 7.49 (dd, J = 7.9, 4.7 Hz, 1H), 7.14 (d, J = 8.6 Hz, 1H), 6.79 (d, J = 2.8 Hz, 1H), 6.66 (dd, J = 8.6, 2.7 Hz, 1H), 5.51 (s, 2H); 13 C NMR (101 MHz, DMSO-d6) δ 165.98, 147.76, 146.42, 145.29, 135.89, 135.82, 131.61, 129.99, 123.44, 116.25, 115.23, 113.61;ESIMS m / z 282 ([M+H]+ ).

[0384] 5-Amino-2-chloro-N-(6-chloropyridin-3-yl)benzamide (C99) [ka] Isolated as a yellow solid (0.560 g, 69%): 1 H NMR (400 MHz, DMSO-d6) δ 10.77 (s, 1H), 8.72 (d, J = 2.7 Hz, 1H), 8.19 (dd, J = 8.7, 2.7 Hz, 1H), 7.52 (d, J = 8.7 Hz, 1H), 7.16 (d, J = 8.6 Hz, 1H), 6.73 (d, J = 2.7 Hz, 1H), 6.68 (dd, J = 8.6, 2.8 Hz, 1H), 5.52 (s, 2H); 13 C NMR (101 MHz, DMSO-d6) δ 165.95, 147.84, 143.95, 140.56, 136.17, 135.28, 130.02, 129.94, 124.27, 116.25, 115.04, 113.36;ESIMS m / z 282 ([M+H] + ).

[0385] 5-Amino-2-chloro-N-(6-cyanopyridin-3-yl)benzamide (C100) [ka] Isolated as a yellow solid (0.292 g, 45%): 1 H NMR (400 MHz, DMSO-d6) δ 11.10 (s, 1H), 8.98 (d, J = 2.5 Hz, 1H), 8.38 (dd, J = 8.6, 2.6 Hz, 1H), 8.03 (d, J = 8.7 Hz, 1H), 7.17 (d, J = 8.6 Hz, 1H), 6.74 (d, J = 2.7 Hz, 1H), 6.69 (dd, J = 8.6, 2.8 Hz, 1H), 5.54 (d, J = 9.0 Hz, 2H); 13 C NMR (101 MHz, DMSO-d6) δ 166.45, 147.89, 142.08, 138.85, 135.78, 130.11, 129.70, 126.37, 126.12, 117.64, 116.48, 114.98, 113.33;ESIMS m / z273 ([M+H] + ).

[0386] 5-Amino-2-chloro-N-(3-fluorophenyl)-N-methylbenzamide (C101) [ka] Isolated as a yellow oil (0.446 g, 99%): 1 H NMR (400 MHz, CDCl3) δ 7.16 (d, J = 7.9 Hz, 2H), 7.03 - 6.77 (m, 4H), 6.47 (s, 2H), 3.61 (s, 2H), 3.47 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -111.45;ESIMS m / z 279 ([M+H] + ).

[0387] 5-Amino-2-chloro-N-(2-fluorophenyl)-N-methylbenzamide (C102) [ka] Isolated as a red-orange oil (0.542 g, quant): 1H NMR (400 MHz, CDCl3) δ 7.26 - 7.13 (m, 2H), 7.04 - 6.94 (m, 2H), 6.91 (d, J = 8.6 Hz, 1H), 6.52 (dd, J = 2.8, 1.4 Hz, 1H), 6.41 (dd, J = 8.6, 2.8 Hz, 1H), 3.59 (s, 2H), 3.42 (d, J = 0.6 Hz, 3H); 19 F NMR (376 MHz, CDCl3) δ -120.54;ESIMS m / z 279 ([M+H] + ).

[0388] 5-Amino-2-chloro-N-(4-cyano-2-methylphenyl)benzamide (C103) [ka] Isolated as a white solid (0.390 g, 86%): 1 H NMR (400 MHz, CDCl3) δ 8.43 (d , J = 8.6 Hz, 1H), 8.23 ​​(s, 1H), 7.57 (dd, J = 8.5, 2.0 Hz, 1H), 7.50 (d, J = 1.9 Hz, 1H), 7.22 (d, J= 8.6 Hz, 1H), 7.19 (d, J = 2.9 Hz, 1H), 6.75 (dd, J = 8.6, 2.9 Hz, 1H), 3.88 (s, 2H), 2.38 (s, 3H); 13 C NMR (101 MHz, CDCl3) δ 145.97, 140.12, 134.26, 134.01, 131.35, 131.27, 128.18, 121.64, 118.89, 118.76, 118.44, 117.09, 107.72, 17.93;ESIMS m / z 286 ([M+H] + ).

[0389] 5-Amino-2-chloro-N-(4-fluoro-2-methylphenyl)benzamide (C104) [ka] Isolated as a red solid (0.430 g, 95%): 1 H NMR (400 MHz, DMSO-d6) δ 9.84 (s, 1H), 7.34 (dd, J = 8.8, 5.7 Hz, 1H), 7.12 (dd, J = 9.0, 2.4 Hz, 2H), 7.04 (td, J = 8.6, 3.0 Hz, 1H), 6.74 (d, J = 2.7 Hz, 1H), 6.63 (dd, J = 8.6, 2.8 Hz, 1H), 5.46 (s, 2H), 2.27 (s, 3H); 19 F NMR (376 MHz, DMSO-d6) δ -117.12;ESIMS m / z279 ([M+H] + ).

[0390] 6-Amino-N-(4-fluorophenyl)picolinamide (C105) [ka] Isolated as a green film (0.072 g, 15%): 1 H NMR (400 MHz, CDCl3) δ 9.82 (s, 1H), 7.70 (dd, J = 7.2, 4.8 Hz, 2H), 7.67 - 7.52 (m, 2H), 7.05 (t, J = 8.3 Hz, 2H), 6.67 (d, J = 7.6 Hz, 1H), 4.63 (s, 2H);IR (thin film) 3333, 1671, 1608 cm -1 ESIMS m / z 232 ([M+H] + ).

[0391] 3-Amino-N-(4-fluorophenyl)-4-methylbenzamide (C106) [ka] Isolated as a pale yellow solid (0.102 g, 15%):1 H NMR (400 MHz, DMSO-d6) δ 10.05 (s, 1H), 7.82 - 7.71 (m, 2H), 7.20 - 7.11 (m, 3H), 7.09 - 7.01 (m, 2H), 5.07 (s, 2H), 2.11 (s, 3H);IR (thin film) 3366, 2924, 1655 cm -1 ESIMS m / z 245 ([M+H] + ).

[0392] 5-Amino-N-(4-fluorophenyl)-2-(trifluoromethoxy)benzamide (C107) [ka] Isolated as a white solid (0.448 g, 81%): mp 115°C-117°C; 1 H NMR (400 MHz, DMSO-d6) δ 10.39 (s, 1H), 7.76 - 7.64 (m, 2H), 7.23 - 7.15 (m, 2H), 7.10 (d, J ESIMS m / z 315 ([M+H] + ).

[0393] 3-Amino-5-chloro-N-(4-fluorophenyl)benzamide (C108) [ka] Isolated as a light brown solid (0.497 g, 81%): mp 133°C-136°C; 1H NMR (400 MHz, DMSO-d6) δ 10.23 (d, J = 8.3 Hz, 1H), 7.82 - 7.68 (m, 2H), 7.25 - 7.12 (m, 2H), 7.10 - 7.00 (m, 2H), 6.76 (t, J = 2.0 Hz, 1H), 5.69 (s, 2H);ESIMS m / z 265 ([M] + ).

[0394] 5-Amino-2-chloro-N-(2-chlorophenyl)benzamide (C109) [ka] Isolated as a red oil (0.391 g, 69%): 1 H NMR (400 MHz, CDCl3) δ 8.60 - 8.53 (m, 2H), 7.41 (dd, J = 8.0, 1.5 Hz, 1H), 7.33 (td, J = 8.0, 1.6 Hz, 1H), 7.22 (d, J = 8.5 Hz, 1H), 7.13 (dd, J = 6.1, 2.2 Hz, 1H), 7.09 (td, J = 7.8, 1.6 Hz, 1H), 6.73 (dd, J = 8.6, 2.9 Hz, 1H), 3.85 (s, 2H); 13 C NMR (101 MHz, CDCl3) δ 145.70, 134.98, 131.82, 131.30, 129.17, 127.77, 126.29, 125.00, 122.04, 121.82, 118.45, 116.57;ESIMS m / z 281 ([M+H] + ).

[0395] 5-Amino-2-chloro-N-(2-isopropylphenyl)benzamide (C110) [ka] Isolated as a red oil (0.461 g, 81%): 1H NMR (400 MHz, CDCl3) δ 7.92 (s, 1H), 7.85 (dd, J = 7.5, 1.9 Hz, 1H), 7.34 (dd, J = 7.2, 2.2 Hz, 1H), 7.29 - 7.18 (m, 3H), 7.17 (d, J = 2.9 Hz, 1H), 6.71 (dd, J = 8.6, 2.9 Hz, 1H), 3.84 (s, 2H), 3.16 (hept, J = 6.9 Hz, 1H), 1.27 (d, J = 6.8 Hz, 6H); 13 C NMR (101 MHz, CDCl3) δ 162.79, 145.76, 140.95, 133.86, 131.14, 126.46, 126.40, 125.71, 124.85, 118.20, 116.87, 28.04, 23.22;ESIMS m / z 289 ([M+H] + ).

[0396] 5-アミノ-2-クロロ-N-(2-エチル-6-メチルフェニル)ベンズアミド(C111)

change

[0397] 5-Amino-2-chloro-N-(3-chlorophenyl)benzamide (C112) [ka] Isolated as an orange solid (0.470 g, 62%): 1 H NMR (400 MHz, CDCl3) δ 8.02 (d, J = 8.1 Hz, 1H), 7.76 (dt, J = 3.8, 2.1 Hz, 1H), 7.53 - 7.43 (m, 1H), 7.34 - 7.28 (m, 1H), 7.19 (d, J = ESIMS m / z 281 ([M+H] + ).

[0398] 5-Amino-2-chloro-N-(2,4-difluorophenyl)-N-methylbenzamide (C113) [ka] Isolated as a yellow foam (0.495 g, 91%): 1 H NMR (300 MHz, CDCl3) δ 6.93 (d, J = 8.6 Hz, 1H), 6.82 - 6.64 (m, 3H), 6.52 (d, J = 2.6 Hz, 1H), 6.44 (dd, J = 8.6, 2.8 Hz, 1H), 3.62 (s, 2H), 3.39 (s, 3H);IR (thin film) 3355, 1645, 1510 cm -1 ESIMS m / z 297 ([M+H] + ).

[0399] 5-amino-2-chloro-4-fluoro-N-(4-fluorophenyl)benzamide (C114) [ka] Isolated as a yellow foam (0.442 g, 95%): 1 H NMR (300 MHz, DMSO-d6) δ 10.44 ESIMS m / z 283 ([M+H] + ).

[0400] 5-Amino-2-chloro-N-(5-fluoropyridin-2-yl)benzamide (C115) [ka] Isolated as a yellow solid (0.073 g, 90%): 1 H NMR (400 MHz, DMSO-d6) δ 10.96 (s, 1H), 8.35 (d, J = 3.1 Hz, 1H), 8.26 - 8.15 (m, 1H), 7.79 (td, J = 8.7, 3.0 Hz, 1H), 7.18 (d, J = 8.8 Hz, 1H), 6.89 - 6.73 (m, 2H), 5.44 (s, 2H); 19 F NMR (376 MHz, DMSO-d6) δ -132.77;ESIMS m / z 266 ([M+H] + ).

[0401] 5-(5-amino-2-chlorobenzamido)-N-methylpicolinamide (C116) [ka] Isolated as a yellow foam (0.187 g, quant): 1H NMR (400 MHz, DMSO-d6) δ 10.86 (s, 1H), 8.92 (dd, J = 5.0, 2.4 Hz, 1H), 8.66 (d, J = 5.0 Hz, 1H), 8.30 (dt, J = 8.6, 2.3 Hz, 1H), 8.03 (dd, J = 8.6, 2.5 Hz, 1H), 7.16 (d, J = 8.6 Hz, 1H), 6.74 (d, J = 2.7 Hz, 1H), 6.68 (dd, J = 8.6, 2.7 Hz, 1H), 5.52 (s, 2H), 2.81 (d, J = 4.8 Hz, 3H);ESIMS m / z 305 ([M+H] + ).

[0402] 5-Amino-2-chloro-N-(pyridin-2-yl)benzamide (C117) [ka] Isolated as a yellow foam (0.152 g, 49%): 1 H NMR (400 MHz, DMSO-d6) δ 11.25 (s, 1H), 8.74 (d, J = 2.7 Hz, 1H), 8.46 (d, J = 2.8 Hz, 1H), 8.41 - 8.35 (m, 1H), 8.32 (dd, J= 8.9, 2.8 Hz, 1H), 8.25 (dd, J= 8.8, 2.7 Hz, 1H), 8.20 (d, J= 8.4 Hz, 1H), 7.92 - 7.78 (m, 3H), 7.21 (ddd, J = 7.4, 4.9, 1.0 Hz, 1H);EIMS m / z 248 ([M+H] + ).

[0403] N-Allyl-5-amino-2-chloro-N-(4-fluorophenyl)benzamide (C118) [ka] Isolated as an orange solid (0.269 g, 60%): ESIMS m / z 305 ([M+H] + ).

[0404] Example 24: Preparation of 5-amino-2-fluoro-N-(4-fluorophenyl)benzamide (C119) [ka] To a solution of 2-fluoro-N-(4-fluorophenyl)-5-nitrobenzamide (C183) (1.06 g, 3.81 mmol) in ethyl acetate (15 mL) under a nitrogen blanket was added palladium on carbon (0.120 g, 0.0560 mmol). The reaction flask was placed on a Parr shaker under hydrogen (45 psi) at room temperature for 16 hours. The reaction was filtered through Celite® and the ethyl acetate was removed. After washing with water and concentrating, the title product was obtained as a white solid (0.955 g, quant.) 1 H NMR (400 MHz, CDCl3) δ 8.46 (d, J = 17.1 Hz, 1H), 7.65 - 7.58 (m, 2H), 7.42 (dd, J = 6.5, 3.1 Hz, 1H), 7.11 - 7.03 (m, 2H), 6.98 (dd, J = 11.8, 8.8 Hz, 1H), 6.78 (ddd, J = 8.7, 4.1, 3.1 Hz, 1H), 3.74 (s, 2H); 19 F NMR (376 MHz, CDCl3) δ -11 7.55, -126.58;EIMS m / z 249 ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 24:

[0405] 3-Amino-2-fluoro-N-(4-fluorophenyl)benzamide (C120) [ka] Isolated as a white solid (1.05 g, 96%): 1 H NMR (400 MHz, CDCl3) δ 8.28 (d, J = 13.9 Hz, 1H), 7.66 - 7.57 (m, 2H), 7.43 (ddd, J = 7.8, 7.0, 1.7 Hz, 1H), 7.12 - 7.03 (m, 3H), 6.95 (ddd, J = 8.7, 7.9, 1.7 Hz, 1H), 3.87 (s, 2H); 19 F NMR (376 MHz, CDCl3) δ -117.54, -136.71;EIMS m / z 249 ([M+H] + ).

[0406] 5-Amino-2-fluoro-N-(4-fluorophenyl)-N-methylbenzamide (C121) [ka] Isolated as a white foam (0.618 g, 98%): 1 H NMR (300 MHz, CDCl3) δ 7.12 - 7.01 (m, 2H), 6.96 - 6.83 (m, 2H), 6.67 - 6.44 (m, 3H), 3.54 (br s, 2H), 3.44 (s, 3H);IR (thin film) 3351, 2922, 1638, 1509cm -1 ESIMS m / z 263 ([M+H] + ).

[0407] 5-Amino-2-fluoro-N-(3-fluorophenyl)-N-methylbenzamide (C122) [ka] Isolated as a white foam (0.595 g, quant): EIMS m / z 263 ([M+H] + ).

[0408] 3-amino-2-fluoro-N-(4-fluorophenyl)-N-methylbenzamide (C123) [ka] Isolated as a green solid (0.595 g, quant): 1 H NMR (300 MHz, CDCl3) δ 7.05 (s, 2H), 6.89 (t, J = 8.3 Hz, 2H), 6.77 (t, J = 7.7 Hz, 1H), 6.59 (dt, J = 13.9, 7.6 Hz, 2H), 3.62 (s, 2H), 3.45 (s, 3H);EIMS m / z 263 ([M+H] + ).

[0409] 5-Amino-2,4-difluoro-N-(4-fluorophenyl)benzamide (C124) [ka] Isolated as a white foam (0.436 g, 87%): 1 H NMR (300 MHz, CDCl3) δ 8.37 (d, J = 16.6 Hz, 1H), 7.66 - 7.53 (m, 3H), 7.11 - 7.02 (m, 2H), 6.89 (dd, J = 11.6, 10.2 Hz, 1H), 3.79 (s, 2H);EIMS m / z 267 ([M+H] + ).

[0410] 5-Amino-N-(2,4-difluorophenyl)-2-fluorobenzamide (C125) [ka] Isolated as a white solid (0.90 g, quant): 1H NMR (400 MHz, CDCl3) δ 8.71 (d, J = 17.8 Hz, 1H), 8.43 (td, J = 9.1, 6.0 Hz, 1H), 7.42 (dd, J = 6.4, 3.1 Hz, 1H), 6.99 (dd, J = 11.7, 8.7 Hz, 1H), 6.96 - 6.86 (m, 2H), 6.80 (ddd, J = 8.7, 4.1, 3.1 Hz, 1H), 3.82 (s, 2H); 19 F NMR (376 MHz, CDCl3) δ -114.82 (d, J= 4.6 Hz), -125.88 (d, J = 4.6 Hz), -126.34 (d, J = 1.4 Hz);EIMS m / z 267 ([M+H] + ).

[0411] 5-Amino-N-(2,4-difluorophenyl)-2-fluoro-N-methylbenzamide (C126) [ka] Isolated as a brown oil (0.54 g, 57%): 1 H NMR (400 MHz, DMSO-d6) δ 7.40 - 7.21 (m, 2H), 7.00 (t, J= 8.6 Hz, 1H), 6.63 (t, J = 9.1 Hz, 1H), 6.50 - 6.37 (m, 2H), 5.01 (s, 2H), 3.25 (s, 3H); 19 F NMR (376 MHz, DMSO-d6) δ -109.77 (d, J = EIMS m / z 281 ([M+H] + ).

[0412] 5-Amino-2-fluoro-N-methyl-N-phenylbenzamide (C127) [ka] Isolated as a white solid (0.92 g, 71%): 1 H NMR (400 MHz, DMSO-d6) δ 7.40 - 7.05 (m, 5H), 6.63 (s, 1H), 6.43 (s, 2H), 4.97 (s, 2H), 3.32 (s, 3H); 19 F NMR (376 MHz, DMSO-d6) δ -131.23;EIMS m / z 245 ([M+H] + ).

[0413] 3-Amino-2-fluoro-N-methyl-N-phenylbenzamide (C128) [ka] Isolated as a white solid (1.07 g, 87%): 1 H NMR (400 MHz, DMSO-d6) δ 7.41 - 7.00 (m, 5H), 6.64 (d, J= 39.8 Hz, 2H), 6.35 (s, 1H), 5.07 (s, 2H), 3.32 (s, 3H); 19 F NMR (376 MHz, DMSO-d6) δ -137.79;EIMS m / z 245 ([M+H] + ).

[0414] 5-Amino-N-(4-cyano-2-fluorophenyl)-2-fluorobenzamide (C129) [ka] Isolated as a yellow solid (0.447 g, 95%): 1 H NMR (400 MHz, DMSO-d6) δ 10.32 - 10.14 (m, 1H), 8.17 (t, J= 8.1 Hz, 1H), 7.95 (dd, J = 10.8, 1.8 Hz, 1H), 7.72 (dt, J = 8.4, 1.2 Hz, 1H), 7.01 (dd, J = 10.5, 8.8 Hz, 1H), 6.89 (dd, J= 6.0, 2.9 Hz, 1H), 6.73 (ddd, J= 8.8, 4.2, 2.9 Hz, 1H), 5.25 (s, 2H); 19 F NMR (376 MHz, DMSO-d6) δ -120.96, -130.61;EIMS m / z 274 ([M+H] + ).

[0415] 5-Amino-2-chloro-N-ethyl-N-(4-fluorophenyl)benzamide (C130) [ka] Isolated as a white solid (0.201 g, 98%): EIMS m / z 293 ([M+H] + ).

[0416] 5-amino-2-chloro-N-(4-fluorophenyl)-N-(2,2,2-trifluoroethyl)benzamide Do (C131) [ka] Isolated as a white solid (0.125 g, 97%): EIMS m / z 347 ([M+H] + ).

[0417] 5-Amino-2-chloro-N-(4-fluorophenyl)-N-propylbenzamide (C132) [ka] Isolated as a white solid (0.267 g, 99%): EIMS m / z 307 ([M+H] + ).

[0418] 5-Amino-N-(4-cyano-2-fluorophenyl)-2-fluoro-N-methylbenzamide (C133) [ka] Isolated as an orange solid (0.120 g, 22%): 1 H NMR (400 MHz, CDCl3) δ 7.45 - 7.17 (m, 4H), 6.70 (dd, J = 5.4, 2.8 Hz, 1H), 6.68 - 6.52 (m, 1H), 3.63 (s, 2H), 3.40 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -116.04, -126.81;EIMS m / z 288 ([M+H] + ).

[0419] 5-Amino-2-chloro-N-(4-cyano-2-fluorophenyl)-N-methylbenzamide (C134) [ka] Isolated as a red-orange solid (0.248 g, 33%): EIMS m / z 304 ([M+H] + ).

[0420] Example 25: Preparation of 6-amino-3-chloro-N-(4-fluorophenyl)picolinamide (C135) [ka]

[0421] Step 1 6-[bis(tert-butoxycarbonyl)amino]-3-chloro-pyridine-2-carboxone Acid (C136) and 6-(tert-butoxycarbonylamino)-3-chloro-pyridine-2-carboxylic acid (C137): [ka] To a solution of methyl 6-[bis(tert-butoxycarbonyl)amino]-3-chloro-pyridine-2-carboxylate (C211) (0.500 g, 1.29 mmol) in tetrahydrofuran (6.5 mL) and water (1.4 mL) was added lithium hydroxide (0.0930 g, 3.88 mmol). After 3 h, the reaction was diluted with hydrochloric acid (0.5 N The mixture was acidified with HCl, and the reaction mixture was extracted with ethyl acetate. The combined organic phases were washed with water, dried over magnesium sulfate, and concentrated to give a 3:1 mixture of (C136):(C137) (0.308 g).

[0422] Step 2. tert-Butyl N-tert-butoxycarbonyl-N-[5-chloro-6-[(4-fluorophenyl)amino]methyl] tert-butyl N-[5-chloro-6-[(4-fluorophenyl)carbamoyl]-2-pyridyl]carbamate (C138) and tert-butyl N-[5-chloro-6-[(4-fluorophenyl)carbamoyl]-2-pyridyl]carbamate (C139): [ka] 6-[Bis(tert-butoxycarbonyl)amino]-3-chloro-pyridine-2-carboxylic acid (C136) and 6-(tert-butoxycarbonylamino)-3-chloro-pyridine-2-carboxylic acid (C137) (0.308 g) were dissolved in 1,2-dichloroethane (3.5 mL), and 4-dimethylaminopyridine (0.165 g, 1.35 mmol), 4-fluoroaniline (0.118 mL, 1.24 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.298 g, 1.56 mmol) were added at room temperature. The reaction was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate, followed by hydrochloric acid (1 N) to give a 3:1 mixture of (C138):(C139) (0.537 g) was obtained.

[0423] Step 3 6-Amino-3-chloro-N-(4-fluorophenyl)picolinamide (C135): A mixture of (C138) and (C139) (0.537 g) was dissolved in dichloromethane (2.4 mL) and trifluoroacetic acid (2.4 mL) was added. After 30 min, the reaction was poured into a separatory funnel and carefully quenched with saturated aqueous sodium bicarbonate. The mixture was extracted with dichloromethane. The combined organic phase was dried over magnesium sulfate and concentrated to give the title compound as a white solid (0.223 g, 0.797 mmol). ) obtained as: 1 H NMR (400 MHz, DMSO-d6) δ 10.49 (s, 1H), 7.79 - 7.66 (m, 2H), 7.54 (d, J = 8.8 Hz, 1H), 7.24 - 7.14 (m, 2H), 6.58 (d, J = 8.8 Hz, 1H), 6.44 (s, 2H);IR (thin film) 3476, 3339, 1685 cm -1 EIMS m / z 266 ([M] + ).

[0424] Example 26: Preparation of 5-amino-2-chloro-N-(4-fluorophenyl)-N-methylbenzothioamide (C140) [ka] A solution of 5-amino-2-chloro-N-(4-fluorophenyl)benzamide (C69) (0.300 g, 1.13 mmol) in tetrahydrofuran (4 mL) was dissolved in 1,1,1,3,3,3-hexamethyldisiloxane (1.21 HCl (0.529 g, 2.38 mmol) was added in one portion, followed by phosphorus pentasulfide (0.529 g, 2.38 mmol). The reaction was warmed to 60° C. for 3 h, cooled to room temperature, and filtered through a pad of Celite®. Filtration The solution was partitioned between ethyl acetate and water. Brine was added until the phases separated. The phases were separated and the organic layer was absorbed onto several tablespoons of Celite®. Purification by flash column chromatography gave the title compound as a yellow solid (0.108 g, 34%): ESIMS m / z 295 ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 26:

[0425] 5-Amino-2-chloro-N-(4-fluorophenyl)benzothioamide (C141) [ka] Isolated as a yellow solid (0.108 g, 34%): ESIMS m / z 281 ([M+H] + ).

[0426] Example 27: Preparation of 5-amino-2-cyano-N-(4-fluorophenyl)benzamide (C142) [ka] To a solution of 5-amino-2-bromo-N-(4-fluorophenyl)benzamide (C79) (0.460 g, 1.49 mmol) in N,N-dimethylformamide (4.25 mL) was added copper(I) cyanide (0.666 g, 7.44 mmol). The reaction was degassed under reduced pressure, backfilled with nitrogen, sealed in a 25-mL vial, and heated in a Biotage Initiator® microwave reactor at 160° C. for 20 minutes, with the temperature monitored via an external infrared sensor on the side of the vessel. The reaction was diluted with ethyl acetate under vigorous stirring, filtered through Celite®, and washed with ethyl acetate. The filtrate was washed with brine. The organic phase was dried over magnesium sulfate, filtered, and concentrated to give the title compound as a yellow solid (0.106 g, 24%): 1H NMR (400 MHz, DMSO-d6) δ 9.53 (s, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.48 - 7.42 (m, 2H), 7.37 - 7.29 (m, 2H), 6.94 (s, 1H), 6.89 (d, J = 9.0 Hz, 1H), 6.21 (s, 2H);ESIMS m / z 256 ([M+H] + ).

[0427] Example 28: Preparation of 2-chloro-N-(4-fluorophenyl)-5-nitrobenzamide (C143) [ka] 2-Chloro-5-nitrobenzoic acid (0.250 g, 1.24 mmol) and 4-dimethylaminopyridine (0.197 g, 1.61 mmol) were reacted with 4-fluoroaniline (0.141 ml, 1.49 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.357 g, 1.86 mmol) to form a 1,2-dichlorobenzoate. Cholesterol (12.4 mL) was then added to the stirred mixture at room temperature, and the reaction was stirred at room temperature for 20 hours. The reaction mixture was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate solution followed by hydrochloric acid (1 N) to give the title compound as a light brown solid (0.188 g, 49%): 1 H NMR (400 MHz, CDCl3) δ 8.59 (d, J = 2.7 Hz, 1H), 8.26 (dd, J = 8.8, 2.8 Hz, 1H), 7.90 (s, 1H), 7.66 (d, J = 8.8 Hz, 1H), 7.64 - 7.57 (m, 2H), 7.15 - 7.05 (m, 2H); 19 F NMR (376 MHz, CDCl3) δ -116.03;ESIMS m / z 295 ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 28:

[0428] N-(4-fluorophenyl)-5-nitro-2-(trifluoromethyl)benzamide (C144) [ka] Isolated as a light brown solid (0.299 g, 41%): 1 H NMR (400 MHz, CDCl3) δ 8.52 (d, J = 2.1 Hz, 1H), 8.44 (dd, J = 8.7, 1.4 Hz, 1H), 7.99 (d, J = 8.6 Hz, 1H), 7.61 - 7.52 (m, 2H), 7.47 (s, 1H), 7.15 - 7.06 (m, 2H);EIMS m / z328 ([M] + ).

[0429] N-(4-fluorophenyl)-2-iodo-5-nitrobenzamide (C145) [ka] Isolated as a brown solid (0.258 g, 37%): 1 H NMR (400 MHz, DMSO-d6) δ 10.68 (s, 1H), 8.29 (d, J = 2.7 Hz, 1H), 8.26 (d, J = 8.6 Hz, 1H), 8.03 (dd, J = 8.6, 2.7 Hz, 1H), 7.77 - 7.67 (m, 2H), 7.30 - 7.19 (m, 2H);IR thin film) 3219, 3069, 1651 cm -1 ESIMS m / z 387 ([M+H] + ).

[0430] 2-chloro-N-(4-cyanophenyl)-5-nitrobenzamide (C146) [ka] Isolated as a yellow solid (0.252 g, 30%): 1 H NMR (400 MHz, DMSO-d6) δ 11.15 IR (thin film) 3275, 3100, 2222, 1667 cm -1 ESIMS m / z 303 ([M+H] + ).

[0431] 2-Chloro-5-nitro-N-(4-(trifluoromethyl)phenyl)benzamide (C147) [ka] Isolated as a yellow solid (0.316 g, 35%): 1 H NMR (400 MHz, CDCl3) δ 8.63 (d, J = 2.7 Hz, 1H), 8.30 (dd, J = 8.8, 2.7 Hz, 1H), 8.00 (s, 1H), 7.79 (d, J = 8.5 Hz, 2H), 7.72 - 7.63 (m, 3H);IR (thin film) 3255, 3078, 1663 cm -1 ESIMS m / z 346 ([M+H] + ).

[0432] 2-chloro-N-(4-chlorophenyl)-5-nitrobenzamide (C148) [ka] Isolated as a yellow solid (0.339 g, 42%): 1H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 2.7 Hz, 1H), 8.28 (dd, J = 8.8, 2.7 Hz, 1H), 7.84 (s, 1H), 7.67 (d, J = 8.8 Hz, 1H), 7.60 (d, J = 8.8 Hz, 2H), 7.38 (d, J = 8.8 Hz, 2H);IR (thin film) 3246, 3105, 1657 cm -1 ESIMS m / z 312 ([M+H] + ).

[0433] 2-chloro-N-(2-chloro-4-fluorophenyl)-5-nitrobenzamide (C149) [ka] Isolated as a yellow solid (0.135 g, 13%): 1 H NMR (400 MHz, CDCl3) δ 8.70 (d, J = 2.7 Hz, 1H), 8.49 (dd, J = 9.2, 5.6 Hz, 1H), 8.37 (s, 1H), 8.31 (dd, J = 8.8, 2.7 Hz, 1H), 7.70 (d, J = IR (thin film) 3237, 3104, 1660 cm -1 ESIMS m / z 330 ([M+H] + ).

[0434] 2-Chloro-5-nitro-N-(o-tolyl)benzamide (C150) [ka] Isolated as a pale red solid (0.221 g, 28%): 1H NMR (400 MHz, CDCl3) δ 8.68 (d, J = 2.7 Hz, 1H), 8.28 (dd, J = 8.8, 2.7 Hz, 1H), 7.94 (d, J = 8.0 Hz, 1H), 7.74 (s, 1H), 7.68 (d, J = 8.8 Hz, 1H), 7.33 - 7.26 (m, 2H), 7.18 (t, J = 7.0 Hz, 1H), 2.36 (s, 3H);IR (thin film) 3239, 3103, 1656 cm -1 ESIMS m / z 290 ([M-H] - ).

[0435] N-(4-fluorophenyl)-2-methyl-5-nitrobenzamide (C151) [ka] Isolated as a light brown solid (0.504 g, 63%): 1 H NMR (400 MHz, CDCl3) δ 8.36 (s, 1H), 8.23 ​​(d, J = 8.4 Hz, 1H), 7.67 - 7.56 (m, 2H), 7.53 (s, 1H), 7.47 (d, J = 8.5 Hz, 1H), 7.10 (t, J = 8.2 Hz, 2H), 2.62 (s, 3H);IR (thin film) 3264, 3074, 1648 cm -1 ESIMS m / z 275 ([M+H] + ).

[0436] 2-Bromo-N-(4-fluorophenyl)-5-nitrobenzamide (C152) [ka] Isolated as a light brown solid (0.370 g, 51%): 1H NMR (400 MHz, CDCl3) δ 8.48 (d, J = 2.6 Hz, 1H), 8.17 (dd, J = 8.8, 2.7 Hz, 1H), 7.86 (d, J = 8.8 Hz, 1H), 7.66 (s, 1H), 7.64 - 7.56 (m, 2H), 7.15 - 7.06 (m, 2H);IR (thin film) 3241, 3097, 1657 cm -1 ESIMS m / z 340 ([M+H] + ).

[0437] N-(4-fluorophenyl)-5-nitro-2-(1H-1,2,4-triazol-1-yl)benzamide (C153) [ka] Isolated as a brown solid (0.367 g, 47%): 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J = 2.5 Hz, 1H), 8.59 (s, 1H), 8.49 (dd, J = 8.7, 2.6 Hz, 1H), 8.19 (s, 1H), 7.90 (s, 1H), 7.79 (d, J = 8.8 Hz, 1H), 7.50 - 7.42 (m, 2H), 7.10 - 7.03 (m, 2H) ;IR (thin film) 3135, 3013, 1673 cm -1 ESIMS m / z 328 ([M+H] + ).

[0438] N-(4-fluorophenyl)-4-nitropicolinamide (C154) [ka] Isolated as a yellow solid (0.602 g, 74%): 1H NMR (400 MHz, CDCl3) δ 9.84 (s, 1H), 8.99 (dd, J = 2.2, 0.6 Hz, 1H), 8.94 (dd, J = 5.3, 0.6 Hz, 1H), 8.24 (dd, J = 5.3, 2.2 Hz, 1H), 7.80 - 7.70 (m, 2H), 7.16 - 7.07 (m, 2H);IR (thin film) 3309, 3076, 1680 cm -1 ESIMS m / z 262 ([M+H] + ).

[0439] 2-chloro-N-(4-fluorophenyl)-3-nitrobenzamide (C155) [ka] Isolated as a yellow solid (0.544 g, 71%): 1 H NMR (400 MHz, CDCl3) δ 7.87 (ddd, J = 12.8, 7.9, 1.6 Hz, 2H), 7.65 (s, 1H), 7.62 - 7.57 (m, 2H), 7.54 (t, J= 7.9 Hz, 1H), 7.14 - 7.06 (m, 2H);IR (thin film) 3263, 3079, 1654 cm -1 ESIMS m / z 296 ([M+H] + ).

[0440] N-(4-fluorophenyl)-2-methoxy-5-nitrobenzamide (C156) [ka] Isolated as a light brown solid (0.624 g, 81%): 1H NMR (400 MHz, CDCl3) δ 9.46 (s, 1H), 9.15 (d, J = 2.9 Hz, 1H), 8.38 (dd, J = 9.1, 3.0 Hz, 1H), 7.66 - 7.58 (m, 2H), 7.16 (d, J = 9.1 Hz, 1H), 7.11 - 7.04 (m, 2H), 4.20 (s, 3H);IR (thin film) 3350, 2082, 1658 cm -1 ESIMS m / z 291 ([M+H] + ).

[0441] 2-Chloro-5-nitro-N-phenylbenzamide (C157) [ka] Isolated as a white solid (1.51 g, 73%): 1 H NMR (400 MHz, CDCl3) δ 8.61 (d, J = 2.7 Hz, 1H), 8.26 (dd, J = 8.8, 2.7 Hz, 1H), 7.85 (s, 1H), 7.70 - 7.59 (m, 3H), 7.46 - 7.36 (m, 2H), 7.25 - 7.18 (m, 1H); 13 C NMR (101 MHz, CDCl3) δ 162.10, 137.49, 136.87, 136.54, 131.63, 129.30, 126.00, 125.55, 125.37, 120.33, 99.98;ESIMS m / z 277 ([M+H] + ).

[0442] 2-chloro-N-(2-fluorophenyl)-5-nitrobenzamide (C158) [ka] Isolated as a white solid (1.38 g, 63%): 1 H NMR (400 MHz, CDCl3) δ 8.68 (d, J = 2.7 Hz, 1H), 8.50 - 8.40 (m, 1H), 8.29 (dd, J = 8.8, 2.8 Hz, 1H), 8.19 (s, 1H), 7.68 (d, J = 8.8 Hz, 1H), 7.26 - 7.20 (m, 1H), 7.20 - 7.12 (m, 2H); 19 F NMR (376 MHz, CDCl3) δ -130.45;ESIMS m / z 295 ([M+H] + ).

[0443] 2-chloro-N-(2,4-difluorophenyl)-5-nitrobenzamide (C159) [ka] Isolated as a pale purple solid (1.48 g, 64%): 1 H NMR (400 MHz, CDCl3) δ 8.68 (d, J = 2.7 Hz, 1H), 8.40 (td, J = 9.1, 6.7 Hz, 1H), 8.30 (dd, J = 8.8, 2.7 Hz, 1H), 8.09 (s, 1H), 7.69 (d, J = 8.8 Hz, 1H), 7.04 - 6.89 (m, 2H); 19 F NMR (376 MHz, CDCl3) δ -113.04 (d, J = 5.0 Hz), -125.45 (d, J = 5.1 Hz);ESIMS m / z 313 ([M+H] + ).

[0444] 2-chloro-N-(4-fluorophenyl)-N-methyl-5-nitrobenzamide (C160) [ka] Isolated as a green solid (1.80 g, 78%): 1H NMR (400 MHz, CDCl3) δ 8.04 - 7.97 (m, 2H), 7.40 (dd, J = 8.5, 0.7 Hz, 1H), 7.19 - 7.11 (m, 2H), 6.96 - 6.88 (m, 2H), 3.50 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -112.30;ESIMS m / z 309 ([M+H] + ).

[0445] 2-chloro-N-(3-fluorophenyl)-5-nitrobenzamide (C161) [ka] Isolated as a white solid (1.38 g, 63%): 1 H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 2.8 Hz, 1H), 8.28 (dd, J = 8.8, 2.7 Hz, 1H), 7.90 (s, 1H), 7.67 (d, J = 8.8 Hz, 1H), 7.61 (dt, J = 10.5, 2.3 Hz, 1H), 7.36 (td, J = 8.2, 6.2 Hz, 1H), 7.30 - 7.27 (m, 1H), 6.93 (tdd, J = 8.2, 2.5, 1.0 Hz, 1H); 19 F NMR (376 MHz, CDCl3) δ -110.61;ESIMS m / z 295 ([M+H] + ).

[0446] 2-chloro-N-(3-cyanophenyl)-5-nitrobenzamide (C162) [ka] Isolated as a light solid (1.41 g, 63%): ESIMS m / z 302 ([M+H] + ).

[0447] 2-chloro-N-(2,3-difluorophenyl)-5-nitrobenzamide (C163) [ka] Isolated as a white solid (1.24 g, 53%): 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J = 2.8 Hz, 1H), 8.31 (dd, J = 8.8, 2.7 Hz, 1H), 8.23 ​​(t, J = 7.3 Hz, 2H), 7.70 (d, J= 8.8 Hz, 1H), 7.22 - 7.11 (m, 1H), 7.09 - 6.96 (m, 1H); 19 F NMR (376 MHz, CDCl3) δ -137.23 (d, J = 20.2 Hz), -154.19 (d, J = 20.3 Hz);ESIMS m / z 313 ([M+H] + ).

[0448] 2-chloro-N-(3,4-difluorophenyl)-5-nitrobenzamide (C164) [ka] Isolated as a dark solid (1.50 g, 65%): 1 H NMR (400 MHz, DMSO-d6) δ 10.95 (s, 1H), 8.51 (d, J = 2.8 Hz, 1H), 8.36 (dd, J = 8.8, 2.8 Hz, 1H), 7.91 (d, J = 8.9 Hz, 1H), 7.89 - 7.83 (m, 1H), 7.54 - 7.37 (m, 2H); 19 F NMR (376 MHz, DMSO-d6) δ -136.87 (d, J = 23.1 Hz), -143.43 (d, J = 23.0 Hz);ESIMS m / z 313 ([M+H] + ) .

[0449] 2-Chloro-5-nitro-N-(2,4,6-trifluorophenyl)benzamide (C165) [ka] Isolated as a white solid (1.80 g, 73%): 1 H NMR (400 MHz, DMSO-d6) δ 10.59 (s, 1H), 8.43 - 8.30 (m, 2H), 7.93 (d, J = 8.7 Hz, 1H), 7.44 - 7.30 (m, 2H); 19 F NMR (376 MHz, DMSO-d6) δ -108.89 (d, J = 5.8 Hz), -114.25 (d, J = 5.7 Hz);ESIMS m / z 331 ([M+H] + ).

[0450] 2-chloro-N-(2,6-difluorophenyl)-5-nitrobenzamide (C166) [ka] Isolated as a white solid (1.06 g, 46%): 1 H NMR (400 MHz, DMSO-d6) δ 10.61 (s, 1H), 8.51 - 8.21 (m, 2H), 7.93 (d, J = 8.7 Hz, 1H), 7.60 - 7.36 (m, 1H), 7.25 (t, J = 8.2 Hz, 2H); 19 F NMR (376 MHz, DMSO-d6) δ -117.43;ESIMS m / z 313 ([M+H] + ).

[0451] 4-chloro-N-(4-fluorophenyl)-3-nitrobenzamide (C167) [ka] Isolated as a yellow solid (0.679 g, 88%):1 H NMR (400 MHz, CDCl3) δ 8.36 (d, J = 2.1 Hz, 1H), 8.04 (dd, J = 8.4, 2.1 Hz, 1H), 7.95 (s, 1H), 7.69 (d, J = 8.4 Hz, 1H), 7.62 - 7.54 (m, 2H), 7.13 - 7.04 (m, 2H);IR (thin film) 3342, 3075, 1651 cm -1 ESIMS m / z 295 ([M+H] + ).

[0452] N-(4-fluorophenyl)-2-methoxy-3-nitrobenzamide (C168) [ka] Isolated as a yellow solid (0.600 g, 65%): 1 H NMR (400 MHz, DMSO-d6) δ 10.60 (s, 1H), 8.04 (dd, J = 8.1, 1.7 Hz, 1H), 7.85 (dd, J = 7.7, 1.7 Hz, 1H), 7.78 - 7.68 (m, 2H), 7.44 (t, J = 7.9 Hz, 1H), 7.23 (dt, J = 11.5, 8.9 Hz, 2H), 3.88 (s, 3H); 13 C NMR (101 MHz, DMSO-d6) δ 163.36, 149.49, 143.90, 135.07, 133.51, 133.03, 126.15, 124.42, 121.53 (d, J CF = 7.8 Hz), 115.43 (d, J CF = 22.3 Hz), 99.49, 63.30;ESIMS m / z291 ([M+H] + ).

[0453] 2-chloro-N-(3-fluorophenyl)-N-methyl-5-nitrobenzamide (C169) [ka] Isolated as a yellow solid (1.46 g, 64%): 1 H NMR (400 MHz, CDCl3) δ 8.02 (d, J = 8.3 Hz, 2H), 7.42 (d, J= 8.5 Hz, 1H), 7.19 (td, J = 8.7, 6.6 Hz, 1H), 6.96 - 6.86 (m, 3H), 3.52 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -110.00;ESIMS m / z309 ([M+H] + ).

[0454] 2-chloro-N-(2-fluorophenyl)-N-methyl-5-nitrobenzamide (C170) [ka] Isolated as a light brown solid (0.61 g, 27%): 1 H NMR (400 MHz, CDCl3) δ 8.13 (dd, J = 2.7, 1.3 Hz, 1H), 7.99 (dd, J = 8.8, 2.7 Hz, 1H), 7.38 (d, J = 8.8 Hz, 1H), 7.25 - 7.15 (m, 2H), 7.05 - 6.97 (m, 2H), 3.48 (d, J= 0.5 Hz, 3H).

[0455] 2-chloro-N-(4-cyano-2-methylphenyl)-5-nitrobenzamide (C171) [ka] Isolated as a white solid (1.14 g, 49%): 1 H NMR (400 MHz, DMSO-d6) δ 10.43 (s, 1H), 8.56 (d, J = 2.8 Hz, 1H), 8.35 (dd, J = 8.8, 2.8 Hz, 1H), 7.89 (dd, J = 14.0, 8.6 Hz, 2H), 7.79 (d, J = 1.9 Hz, 1H), 7.77 - 7.69 (m, 1H), 2.34 (s, 3H) ; 13 C NMR (101 MHz, DMSO-d6) δ 163.33, 146.15, 140.02, 137.41, 137.00, 134.26, 133.14, 131.25, 130.22, 125.78, 125.48, 124.03, 118.76, 107.91, 17.62; + ).

[0456] 2-chloro-N-(4-fluoro-2-methylphenyl)-5-nitrobenzamide (C172) [ka] Isolated as a pale purple solid (1.45 g, 63%): 1 H NMR (400 MHz, DMSO-d6) δ 10.20 (s, 1H), 8.50 (d, J = 2.8 Hz, 1H), 8.34 (dd, J = 8.8, 2.8 Hz, 1H), 7.90 (d, J = 8.9 Hz, 1H), 7.51 (dd, J = 8.8, 5.6 Hz, 1H), 7.16 (dd, J = 9.8, 3.0 Hz, 1H), 7.09 (td, J = 8.6, 3.0 Hz, 1H), 2.30 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -116.56;ESIMS m / z 309 ([M+H] + ).

[0457] N-(4-fluorophenyl)-6-nitropicolinamide (C173) [ka] Isolated as a light brown solid (0.511 g, 49%): mp 169°C-170°C; 1H NMR (400 MHz, DMSO-d6) δ 10.62 (s, 1H), 8.68 - 8.29 (m, 3H), 7.92 - 7.80 (m, 2H), 7.29 - 7.15 (m, 2H);ESIMS m / z 262 ([M+H] + ).

[0458] N-(4-fluorophenyl)-4-methyl-3-nitrobenzamide (C174) [ka] Isolated as an off-white solid (0.711 g, 89%): mp 136°C-138°C; 1 H NMR (400 MHz, DMSO-d6) δ 10.52 (s, 1H), 8.57 (d, J = 1.8 Hz, 1H), 8.21 (dd, J = 8.0, 1.8 Hz, 1H), 7.83 - 7.74 (m, 2H), 7.69 (d, J = 8.1 Hz, 1H), 7.28 - 7.16 (m, 2H), 2.60 (s, 3H);ESIMS m / z 275 ([M+H] + ).

[0459] N-(4-fluorophenyl)-5-nitro-2-(trifluoromethoxy)benzamide (C175) [ka] Isolated as a yellow solid (0.544 g, 75%): mp 175°C-177°C; 1 H NMR (400 MHz, CDCl3) δ 8.97 (d, J = 2.9 Hz, 1H), 8.43 (dd, J = 9.0, 2.9 Hz, 1H), 8.24 (s, 1H), 7.63 - 7.57 (m, 2H), 7.57 - 7.52 (m, 1H), 7.15 - 7.07 (m, 2H);ESIMS m / z 345 ([M+H] + ).

[0460] 3-chloro-N-(4-fluorophenyl)-5-nitrobenzamide (C176) [ka] Isolated as a yellow solid (0.645 g, 84%): mp 209°C-210°C; 1 H NMR (400 MHz, DMSO-d6) δ 10.68 (s, 1H), 8.74 - 8.68 (m, 1H), 8.51 (t, J = 2.0 Hz, 1H), 8.47 (t, J = 1.7 Hz, 1H), 7.84 - 7.74 (m, 2H), 7.30 - 7.17 (m, 2H);ESIMS m / z 295 ([MH] - ).

[0461] 2-chloro-N-(2-chlorophenyl)-5-nitrobenzamide (C177) [ka] Isolated as a yellow solid (1.14 g, 49%): 1 H NMR (400 MHz, CDCl3) δ 8.69 (d, J = 2.7 Hz, 1H), 8.53 (dd, J = 8.2, 1.5 Hz, 1H), 8.48 (s, 1H), 8.30 (dd, J = 8.8, 2.7 Hz, 1H), 7.69 (d, J = 8.8 Hz, 1H), 7.45 (dd, J = 8.0, 1.5 Hz, 1H), 7.42 - 7.32 (m, 1H), 7.20 - 7.10 (m, 1H); 13 C NMR (101 MHz, CDCl3) δ 161.91, 146.79, 137.41, 136.03, 133.91, 131.81, 129.29, 127.97, 126.28, 125.87, 125.79, 123.41, 122.01;ESIMS m / z 311 ([M+H] + ).

[0462] 2-chloro-N-(2-isopropylphenyl)-5-nitrobenzamide (C178) [ka] Isolated as a white solid (1.79 g, 75%): 1 H NMR (400 MHz, DMSO-d6) δ 10.21 (s, 1H), 8.45 (d, J = 2.7 Hz, 1H), 8.34 (dd, J = 8.8, 2.8 Hz, 1H), 7.89 (d, J = 8.8 Hz, 1H), 7.41 (ddd, J = 19.3, 7.6, 1.7 Hz, 2H), 7.27 (dtd, J = 18.7, 7.3, 1.6 Hz, 2H), 3.34 - 3.24 (m, 1H), 1.19 (d, J = 6.9 Hz, 6H); 13 C NMR (101 MHz, DMSO-d6) δ 163.78, 146.11, 143.95, 138.02, 136.97, 133.74, 131.29, 127.35, 127.05, 125.90, 125.71, 125.50, 123.70, 27.19, 23.25;ESIMS m / z 319 ([M+H] + ).

[0463] 2-chloro-N-(2-ethyl-6-methylphenyl)-5-nitrobenzamide (C179) [ka] Isolated as a white solid (1.31 g, 55%): 1H NMR (400 MHz, DMSO-d6) δ 10.14 (s, 1H), 8.36 (dd, J = 8.8, 2.8 Hz, 1H), 8.31 (d, J = 2.7 Hz, 1H), 7.92 (d, J = 8.8 Hz, 1H), 7.24 - 7.13 (m, 3H), 2.66 (q, J= 7.5 Hz, 2H), 2.30 (s, 3H), 1.17 (t, J= 7.5 Hz, 3H); 13 C NMR (101 MHz, DMSO-d6) δ 163.25, 146.11, 141.22, 137.80, 136.96, 135.68, 133.26, 131.56, 127.89, 127.40, 126.30, 125.65, 123.36, 24.41, 18.24, 14.77;ESIMS m / z 319 ([M+H] + ).

[0464] 2-chloro-N-(3-chlorophenyl)-5-nitrobenzamide (C180) [ka] Isolated as an off-white solid (1.46 g, 63%): 1 H NMR (400 MHz, DMSO-d6) δ 10.90 (s, 1H), 8.51 (d, J = 2.7 Hz, 1H), 8.36 (dd, J = 8.8, 2.8 Hz, 1H), 7.99 - 7.84 (m, 2H), 7.57 (ddd, J = 8.2, 2.0, 1.0 Hz, 1H), 7.42 (t, J = 8.1 Hz, 1H), 7.22 (ddd, J = 8.0, 2.1, 1.0 Hz, 1H); 13 C NMR (101 MHz, DMSO-d6) δ 162.99, 146.13, 139.85, 137.29, 137.02, 133.13, 131.36, 130.60, 125.88, 123.95, 123.93, 119.24, 118.19;ESIMS m / z 311 ([M+H]+ ).

[0465] 2-chloro-N-(2,4-difluorophenyl)-N-methyl-5-nitrobenzamide (C181) [ka] Isolated as a green solid (0.72 g, 36%): 1 H NMR (300 MHz, CDCl3) δ 8.13 (dd, J = 2.7, 1.4 Hz, 1H), 8.03 (dd, J = 8.8, 2.7 Hz, 1H), 7.40 (dd, J = 8.8, 0.4 Hz, 1H), 7.24 (td, J = 8.9, 5.9 Hz, 1H), 6.84 - 6.71 (m, 2H), 3.45 (d, J = 0.5 Hz, 3H);IR (thin film) 3074, 1654, 1527, 1607 cm -1 ESIMS m / z 327 ([M+H] + ).

[0466] 2-chloro-N-(4-cyano-2-fluorophenyl)-5-nitrobenzamide (C182) [ka] Isolated as a tan solid (0.642 g, 41%): 1 H NMR (400 MHz, DMSO-d6) δ 11.01 (s, 1H), 8.53 (d, J = 2.8 Hz, 1H), 8.41 - 8.24 (m, 2H), 7.98 (dd, J = 10.8, 1.9 Hz, 1H), 7.89 (d, J = 8.8 Hz, 1H), 7.77 (ddd, J = 8.5, 1.9, 0.9 Hz, 1H); 19 F NMR (376 MHz, DMSO-d6) δ -121.17;ESIMS m / z320 ([M+H] + ).

[0467] Example 29: Preparation of 2-fluoro-N-(4-fluorophenyl)-5-nitrobenzamide (C183) [ka] A solution of 2-fluoro-5-nitrobenzoic acid (1.0 g, 5.40 mmol) in thionyl chloride (7.0 mL, 96 mmol) was heated to reflux for 4 hours. The reaction mixture was then concentrated. Anhydrous toluene (1.0 mL) was added. The residue was added twice and concentrated to remove any remaining thionyl chloride. was dissolved in anhydrous dichloromethane (20 mL), and pyridine (0.87 mL, 11 mmol) was added. The solution was cooled in an ice bath and added with 4-fluoroaniline (0.60 mL) dissolved in dichloromethane (5.0 mL). g, 5.4 mmol) was added over 20 minutes. The reaction was stirred in an ice bath for 45 minutes. The reaction was washed with hydrochloric acid (1 M) (2 x 20 mL) followed by saturated aqueous sodium bicarbonate (2 x 20 mL). The organic layer was poured into a phase separator and concentrated to give the title compound as a white solid (1.2 g, 71%): 1 H NMR (400 MHz, CDCl3) δ 9.07 (dd, J = 6.6, 3.0 Hz, 1H), 8.42 (ddd, J = 9.0, 4.3, 3.0 Hz, 1H), 8.32 (d, J = 13.8 Hz, 1H), 7.68 - 7.59 (m, 2H), 7.40 (dd, J= 10.7, 9.0 Hz, 1H), 7.16 - 7.06 (m, 2H); 19 F NMR (376 MHz, CDCl3) δ -104.29, -116.18; ESIMS m / z 279. ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 29:

[0468] 2-Fluoro-N-(4-fluorophenyl)-3-nitrobenzamide (C184) [ka] Isolated as a white solid (1.22 g, 81%): 1 H NMR (400 MHz, CDCl3) δ 8.44 (ddd, J = 8.3, 6.6, 1.9 Hz, 1H), 8.27 (s, 1H), 8.22 (ddd, J = 8.1, 7.3, 1.9 Hz, 1H), 7.68 - 7.57 (m, 2H), 7.49 (td, J = 8.0, 1.0 Hz, 1H), 7.16 - 7.05 (m, 2H); 19 F NMR (376 MHz, CDCl3) δ -116.17, -121.77;EIMS m / z 279 ([M] + ).

[0469] Example 30: Preparation of 2-chloro-5-nitro-N-(pyridin-4-yl)benzamide (C185) [ka] 2-Chloro-5-nitrobenzoic acid (0.500 g, 2.48 mmol) in dichloromethane (8.3 mL) To the mixture was slowly added oxalyl chloride (0.239 mL, 2.73 mmol), followed by N,N-dimethylformamide. The amide (1 drop) was added. The reaction was stirred at room temperature for 2 hours. To the solution was added triethylamine (0.691 mL, 4.96 mmol), followed by pyridin-4-amine (0.467 g, 4.96 mmol) in dichloromethane (1 mL). The reaction was stirred at room temperature for 16 hours. Purification by flash column chromatography using 0% to 100% ethyl acetate / hexanes as eluent afforded the title compound as a tan solid (0.401 g, 58%): 1H NMR (400 MHz, DMSO-d6) δ 11.10 (s, 1H), 8.64 - 8.45 (m, 3H), 8.37 (dd, J = 8.9, 2.8 Hz, 1H), 7.92 (d, J = 8.8 Hz, 1H), 7.73 - 7.61 (m, 2H); 13 C NMR (101 MHz, DMSO-d6) δ 163.67, 150.56, 146.14, 145.04, 136.95, 131.40, 126.06, 124.00, 113.68;ESIMS m / z 278 ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 30:

[0470] 2-Chloro-5-nitro-N-(pyridin-3-yl)benzamide (C186) [ka] Isolated as a white solid (0.480 g, 70%): 1 H NMR (400 MHz, DMSO-d6) δ 10.95 (s, 1H), 8.85 (dd, J = 2.6, 0.7 Hz, 1H), 8.54 (d, J = 2.8 Hz, 1H), 8.42 - 8.31 (m, 2H), 8.15 (ddd, J = 8.3, 2.6, 1.5 Hz, 1H), 7.92 (d, J = 8.8 Hz, 1H), 7.44 (ddd, J = 8.3, 4.7, 0.8 Hz, 1H); 13 C NMR (101 MHz, DMSO-d6) δ 163.19, 146.13, 145.14, 141.29, 137.17, 137.04, 135.17, 131.38, 126.78, 125.92, 123.99, 123.76;ESIMS m / z 278 ([M+H] + ).

[0471] 2-Chloro-N-(2-chloropyridin-3-yl)-5-nitrobenzamide (C187) [ka] Isolated as a white solid (0.364 g, 47%): 1 H NMR (400 MHz, DMSO-d6) δ 10.67 (s, 1H), 8.53 (d, J = 2.8 Hz, 1H), 8.40 - 8.31 (m, 2H), 8.26 (ddt, J = 6.1, 4.5, 2.4 Hz, 1H), 7.91 (d, J = 8.9 Hz, 1H), 7.55 (dd, J = 7.9, 4.7 Hz, 1H); 13 C NMR (101 MHz, DMSO-d6) δ 146.77, 146.02, 144.78, 137.16, 136.84, 135.87, 131.34, 131.11, 125.95, 124.13, 123.50;ESIMS m / z 312 ([M+H] + ).

[0472] 2-Chloro-N-(6-chloropyridin-3-yl)-5-nitrobenzamide (C188) [ka] Isolated as a white solid (0.639 g, 83%): 1 H NMR (400 MHz, DMSO-d6) δ 11.10 (s, 1H), 8.71 (d, J = 2.7 Hz, 1H), 8.56 (d, J = 2.7 Hz, 1H), 8.37 (dd, J = 8.8, 2.8 Hz, 1H), 8.19 (dd, J = 8.7, 2.8 Hz, 1H), 7.92 (d, J = 8.8 Hz, 1H), 7.57 (d, J = 8.7 Hz, 1H); 13C NMR (101 MHz, DMSO-d6) δ 163.20, 146.12, 144.54, 140.93, 137.05, 136.85, 134.79, 131.43, 130.44, 126.08, 124.39, 124.07;ESIMS m / z 312 ([M+H] + ).

[0473] 2-chloro-N-(6-cyanopyridin-3-yl)-5-nitrobenzamide (C189) [ka] Isolated as a white foam (0.433 g, 58%): ESIMS m / z 303 ([M+H] + ).

[0474] 2-chloro-N-(5-fluoropyridin-2-yl)-5-nitrobenzamide (C190) [ka] Isolated as a pale yellow foam (0.094 g, 21%): 1 H NMR (300 MHz, acetone-d6) δ 10.29 (s, 1H), 8.56 (d, J = 2.7 Hz, 1H), 8.46 - 8.34 (m, 2H), 8.27 (d, J = 3.0 Hz, 1H), 7.91 - 7.81 (m, 1H), 7.82 - 7.70 (m, 1H);IR (thin film) 3112, 1688, 1610, 1576, 1522 cm -1 ESIMS m / z 296 ([M+H] + ).

[0475] 5-(2-chloro-5-nitrobenzamido)-N-methylpicolinamide (C191) [ka] Isolated as a light brown foam (0.330 g, 66%): 1H NMR (400 MHz, DMSO-d6) δ11.16 (s, 1H), 8.90 (d, J = 2.4 Hz, 1H), 8.66 (q, J = 4.8 Hz, 1H), 8.58 (d, J = 2.8 Hz, 1H), 8.37 (dd, J = 8.9, 2.8 Hz, 1H), 8.30 (dd, J = 8.5, 2.4 Hz, 1H), 8.07 (d, J = 8.5 Hz, 1H), 7.92 (d, J = 8.8 Hz, 1H), 2.82 (d, J = 4.8 Hz, 3H); 13 C NMR (101 MHz, DMSO-d6) δ 163.92, 163.34, 146.15, 145.63, 139.52, 137.32, 137.06, 136.89, 131.43, 127.28, 126.07, 124.09, 122.28, 25.90;ESIMS m / z 335 ([M+H] + ).

[0476] 2-Chloro-5-nitro-N-(pyridin-4-yl)benzamide (C192) [ka] Isolated as a tan solid (0.401 g, 58%): 1 H NMR (400 MHz, DMSO-d6) δ 11.10 (s, 1H), 8.64 - 8.45 (m, 3H), 8.37 (dd, J = 8.9, 2.8 Hz, 1H), 7.92 (d, J = 8.8 Hz, 1H), 7.73 - 7.61 (m, 2H); 13 C NMR (101 MHz, DMSO-d6) δ 163.67, 150.56, 146.14, 145.04, 136.95, 131.40, 126.06, 124.00, 113.68;ESIMS m / z 278 ([M+H] + ).

[0477] Example 31: 2-Fluoro-N-(4-fluorophenyl)-N-methyl-5-nitrobenzamide (C193 Preparation of [ka] To a solution of 2-fluoro-5-nitrobenzoic acid (0.500 g, 2.70 mmol) in dichloromethane (10 mL), oxalyl chloride (0.355 mL, 4.05 mmol) was slowly added, followed by N,N-dimethylformamide. The amide (1 drop) was added. The reaction was stirred at room temperature for 90 minutes. The reaction mixture was concentrated and the residue was dissolved in dichloromethane. To the solution was added pyridine (0.437 mL, 5.40 mmol) and the solution was cooled to 0°C. To the cooled solution was added 4-fluoro-2-methyl-2-propanol dissolved in dichloromethane (5 mL). 1H-N-methylaniline (0.338 g, 2.70 mmol) was added over 20 minutes. After 45 minutes, the mixture was cooled to room temperature and cooled to room temperature. The solvent was removed and the reaction was stirred at room temperature for 16 hours. The reaction was diluted with dichloromethane and washed with hydrochloric acid (1 M) (2 x 20 mL). The organic layer was poured into a phase separator and concentrated to give the title compound as a white solid. as a colored solid (0.804 g, 92%): 1 H NMR (300 MHz, CDCl3) δ 8.23 ​​(dd, J = 5.5, 2.8 Hz, 1H), 8.13 (ddd, J = 9.1, 4.4, 2.8 Hz, 1H), 7.14 - 7.05 (m, 2H), 7.05 - 6.87 (m, 3H), 3.49 (s, 3H);IR (thin film) 3039, 1647, 1627, 1506 cm -1 ESIMS m / z 293 ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 31:

[0478] 2-Fluoro-N-(3-fluorophenyl)-N-methyl-5-nitrobenzamide (C194) [ka] Isolated as a white solid (0.740 g, 94%): 1 H NMR (300 MHz, CDCl3) δ 8.26 (s, 1H), 8.22 - 8.07 (m, 1H), 7.27 - 7.13 (m, 1H), 7.03 (t, J= 8.6 Hz, 1H), 6.99 - 6.73 (m, 3H), 3.51 (s, 3H);IR (thin film) 3080, 1659, 1629, 1587 cm -1 .

[0479] 2-Fluoro-N-(4-fluorophenyl)-N-methyl-3-nitrobenzamide (C195) [ka] Isolated as a yellow solid (0.675 g, 86%): 1 H NMR (300 MHz, CDCl3) δ 7.93 (ddd, J = 8.6, 7.1, 1.8 Hz, 1H), 7.56 (ddd, J = 7.4, 5.3, 1.8 Hz, 1H), 7.19 (td, J IR (thin film) 3086, 1653, 1614, 1536 cm -1 ESIMS m / z 293 ([M+H] + ).

[0480] 2-chloro-4-fluoro-N-(4-fluorophenyl)-5-nitrobenzamide (C196) [ka] Isolated as a yellow solid (0.532 g, 75%): 1IR (thin film) 3265, 3072, 1614, 1530cm -1 ESIMS m / z 313 ([M+H] + ).

[0481] 2,4-Difluoro-N-(4-fluorophenyl)-5-nitrobenzamide (C197) [ka] Isolated as a green solid (0.576 g, 79%): 1 H NMR (300 MHz, CDCl3) δ 9.00 (t, J = 8.2 Hz, 1H), 8.23 ​​(d, J= 13.4 Hz, 1H), 7.67 - 7.53 (m, 2H), 7.21 (dd, J = 10.9, 9.7 Hz, 1H), 7.15 - 7.06 (m, 2H);IR (thin film) 3080, 1687, 1614, 1590 cm -1 ESIMS m / z 297 ([M+H] + ).

[0482] N-(2,4-difluorophenyl)-2-fluoro-5-nitrobenzamide (C198) [ka] Isolated as a grey solid (3.1 g, 97%): 1 H NMR (400 MHz, CDCl3) δ 9.08 (dd, 7.41 (dd, J = 10.6, 9.1 Hz, 1H), 6.95 (tdd, J = 11.1, 7.0, 3.2Hz, 2H) ; 19 F NMR (376 MHz, CDCl3) δ -104.13 , -113.26 (d, J = 5.0 Hz), -125.68 (d, J= 5.2 Hz);ESIMS m / z297 ([M+H] + ).

[0483] 2-Fluoro-N-methyl-5-nitro-N-phenylbenzamide (C199) [ka] Isolated as a brown oil (1.45 g, 98%): 1 H NMR (400 MHz, CDCl3) δ 8.21 (dd, J = 5.6, 2.8 Hz, 1H), 8.15 - 8.05 (m, 1H), 7.26 - 7.14 (m, 3H), 7.09 (d, J= 7.7 Hz, 2H), 6.98 (t, J = 8.6 Hz, 1H), 3.52 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -102.19;ESIMS m / z 275 ([M+H] + ).

[0484] 2-Fluoro-N-methyl-3-nitro-N-phenylbenzamide (C200) [ka] Isolated as a light brown solid (1.38 g, 93%): 1 H NMR (400 MHz, CDCl3) δ 7.94 - 7.85 (m, 1H), 7.55 (ddd, J = 7.5, 5.4, 1.8 Hz, 1H), 7.26 - 7.12 (m, 4H), 7.08 (d, J = 7.6 Hz, 2H), 3.51 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -118.54;ESIMS m / z 275 ([M+H] + ).

[0485] N-(4-cyano-2-fluorophenyl)-2-fluoro-5-nitrobenzamide (C201) [ka] Isolated as a light brown solid (1.1 g, 84%): 1 H NMR (400 MHz, DMSO-d6) δ 10.89 (s, 1H), 8.59 (dd, J = 5.8, 2.9 Hz, 1H), 8.49 (ddd, J= 9.1, 4.3, 3.0 Hz, 1H), 8.24 (t, J= 8.1 Hz, 1H), 7.99 (dd, J = 10.8, 1.8 Hz, 1H), 7.77 (ddd, J= 8.4, 1.9, 0.9 Hz, 1H), 7.69 (t, J= 9.2 Hz, 1H); 19 F NMR (376 MHz, DMSO-d6) δ -103.66, -120.88;ESIMS m / z 304 ([M+H] + ).

[0486] Example 32: Preparation of N-(2,4-difluorophenyl)-2-fluoro-N-methyl-5-nitrobenzamide (C202) [ka] To a solution of N-(2,4-difluorophenyl)-2-fluoro-5-nitrobenzamide (C198) (1.00 g, 3.38 mmol) in anhydrous N,N-dimethylformamide (15 mL) cooled in an ice bath was added sodium hydride (60% oil immersion, 0.162 g, 4.05 mmol). The resulting slurry was stirred for 30 minutes. Iodomethane (0.422 mL, 6.75 mmol) was added. The reaction was stirred for 2 hours. An additional amount of sodium hydride (0.0400 g) was added. An additional amount of iodomethane (0.100 mL) was added. The reaction was left stirring for 16 hours. The reaction was quenched by the slow addition of water (15 mL). The mixture was diluted with ethyl acetate (25 mL). The phases were separated and the organic layer was washed with 1:1 brine / water (3×20 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to give the title compound. Obtained as a brown oil (1.05 g, quant): 1 H NMR (400 MHz, CDCl3) δ 8.32 - 8.24 (m, 1H), 8.15 (ddd, J= 9.1, 4.3, 2.8 Hz, 1H), 7.23 - 7.12 (m, 1H), 7.02 (dd, J = 9.1, 8.2 Hz, 1H), 6.85 - 6.71 (m, 2H), 3.44 (s, 3H); 19 F NMR (376 MHz, CDCl3) δ -102.79 (d, J = 5.6 Hz), -107.11 (d, J = 8.2 Hz), -115.48 (dd, J = 8.3, 5.6 Hz);ESIMS m / z 311 ([M+H] + ). The following compounds were prepared in a manner similar to the procedure outlined in Example 32:

[0487] 2-chloro-N-ethyl-N-(4-fluorophenyl)-5-nitrobenzamide (C203) [ka] Isolated with iodoethane as a tan solid (0.225 g, quant): 1 H NMR (400 MHz, CDCl3) δ 8.02 - 7.94 (m, 2H), 7.42 - 7.35 (m, 1H), 7.18 - 7.11 (m, 2H), 6.98 - 6.86 (m, 2H), 3.97 (q, J = 7.2 Hz, 2H), 1.27 (t, J = 7.2 Hz, 4H); 19 F NMR (376 MHz, CDCl3) δ -112.13;ESIMS m / z323 ([M+H] + ).

[0488] 2-chloro-N-(4-fluorophenyl)-5-nitro-N-(2,2,2-trifluoroethyl)benzamide Do(C204) [ka] Isolated as a white solid using 2,2,2-trifluoroethyl methanesulfonate (0.147 g, 58%): 1 H NMR (400 MHz, CDCl3) δ 8.03 (dd, J = 8.7, 2.7 Hz, 1H), 8.00 (d, J = 2.5 Hz, 1H), 7.42 (dd, J = 8.8, 0.5 Hz, 1H), 7.25 - 7.19 (m, 2H), 6.99 - 6.91 (m, 2H), 4.55 (q, J = 8.6 Hz, 2H); 19 F NMR (376 MHz, CDCl3) δ -68.62, -110.49;ESIMS m / z 377 ([M+H] + ).

[0489] 2-chloro-N-(4-fluorophenyl)-5-nitro-N-propylbenzamide (C205) [ka] Isolated using iodopropane as a tan solid (0.296 g, quant): 1 H NMR ( 400 MHz, DMSO-d6) δ 8.32 (d, J = 2.8 Hz, 1H), 8.05 (dd, J = 8.8, 2.8 Hz, 1H), 7.62 (d, J = 8.8 Hz, 1H), 7.42 - 7.34 (m, 2H), 7.15 - 7.06 (m, 2H), 3.81 (t, J = 7.4 Hz, 2H), 1.55 (h, J= 7.4 Hz, 2H), 0.93 (t, J = 7.4 Hz, 3H); 19 F NMR (376 MHz, DMSO-d6) δ -113.51;ESIMS m / z337 ([M+H] + ).

[0490] N-Allyl-2-chloro-N-(4-fluorophenyl)-5-nitrobenzamide (C206) [ka] Isolated with 3-bromoprop-1-ene as a white solid (0.269 g, 91%): 1 H NMR (400 MHz, DMSO-d6) δ 8.40 (d, J = 2.8 Hz, 1H), 8.06 (dd, J = 8.9, 2.8 Hz, 1H), 7.62 (d, J = 8.9 Hz, 1H), 7.43 - 7.30 (m, 2H), 7.17 - 7.02 (m, 2H), 5.93 (ddt, J = 17.2, 10.2, 6.0 Hz, 1H), 5.31 - 5.11 (m, 2H), 4.47 (d, J = 6.0 Hz, 2H); 19 F NMR (376 MHz, DMSO-d6) δ -113.49;ESIMS m / z 335 ([M+H] + ).

[0491] N-(4-cyano-2-methylphenyl)-2-fluoro-N-methyl-5-nitrobenzamide (C207) [ka] Isolated as a tan solid (0.595 g, 94%): 1 H NMR (400 MHz, DMSO-d6) δ 8.52 - 8.17 (m, 2H), 7.94 (d, J= 10.1 Hz, 1H), 7.84 - 7.60 (m, 2H), 7.44 (s, 1H), 3.36 (s, 3H); 19 F NMR (376 MHz, DMSO-d6) δ -104.90 , -118.40;ESIMS m / z 318 ([M+H] + ).

[0492] 2-chloro-N-(4-cyano-2-fluorophenyl)-N-methyl-5-nitrobenzamide (C208) [ka] Isolated as a white solid (0.826 g, 95%): ESIMS m / z 334 ([M+H] + ).

[0493] Example 33: Preparation of 5-nitro-2-(1H-1,2,4-triazol-1-yl)benzoic acid (C209) [ka] To a solution of methyl 5-nitro-2-(1H-1,2,4-triazol-1-yl)benzoate (C210) (1.24 g, 5.00 mmol) in tetrahydrofuran (25 mL) and water (5.0 mL) was added lithium hydroxide (0.359 g, 15.0 mmol). The reaction was stirred at room temperature for 2.5 hours. The reaction was acidified with hydrochloric acid (1 N). The reaction mixture was then acidified and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated to give the title compound as a pale yellow solid (1.14 g, 93%). And got: 1 IR (thin film) 3169, 3097, 1713cm -1 ESIMS m / z 235 ([M+H] + ).

[0494] Example 34: Preparation of methyl 5-nitro-2-(1H-1,2,4-triazol-1-yl)benzoate (C210) [ka] To a solution of methyl 2-chloro-5-nitrobenzoate (2.00 g, 9.28 mmol) in N,N-dimethylformamide (18.5 mL) was added 1H-1,2,4-triazole (0.673 g, 9.74 mmol). The reaction was stirred at 50 °C for 2 h, stirred at room temperature overnight, and heated at 80 °C for 2 h. Water was added, and the mixture was extracted with diethyl ether. The combined organic layers were washed with brine (2x) and concentrated with magnesium sulfate. Drying, filtration and concentration gave the title compound as a pale yellow solid (1.25 g, 51%): 1 H NMR (400 MHz, DMSO-d6) δ 9.21 (s, 1H), 8.62 - 8.57 (m, 2H), 8.31 (s, 1H), 8.09 - 8.03 (m, 1H), 3.75 (s, 3H);ESIMS m / z249 ([M+H] + ).

[0495] Example 35: Preparation of methyl 6-[bis(tert-butoxycarbonyl)amino]-3-chloro-pyridine-2-carboxylate (C211) [ka] To a solution of methyl 6-amino-3-chloropicolinate (2.00 g, 10.7 mmol) in tert-butanol (21 mL) and acetone (6.0 mL) was added 4-dimethylaminopyridine (0.0200 g, 0.161 mmol) and di-tert-butyl dicarbonate (8.21 mL, 35.4 mmol). The reaction was stirred at room temperature for 2 h. The reaction mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate, and Filtration and concentration were followed by purification by flash column chromatography using 0% to 100% ethyl acetate / hexanes as eluent to give the title compound as a white solid (2.45 g, 56%). 1 H NMR (400 MHz, CDCl3) δ 7.81 (d, J = 8.6 Hz, 1H), 7.40 (d, J = 8.6 Hz, 1H), 3.97 (s, 3H), 1.46 (s, 18H);IR (thin film) 2978, 1778, 1742 cm -1 ;EIMS m / z 387 ([M] + ). The following molecules in Table 1 may be prepared according to the procedures disclosed above.

[0496] Table P1: Possible molecular structures and preparation methods [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4] [Table 2-5] [Table 2-6]

Table 2-7

Table 2-8

Table 2-9

Table 2-10

Table 2-11

Table 2-12

Table 2-13

Table 2-14

Table 2-15

Table 2-16

Table 2-17

Table 2-18

Table 2-19

Table 2-20

Table 2-21

Table 2-22

Table 2-23

[0497] trans-2,2-dichloro-3-(4-methoxyphenyl)cyclopropane-1-carboxylic acid (C212) [ka] Isolated as white crystals (0.090 g, 27%): 1 H NMR (400 MHz, CDCl3) δ 11.33 (s, 1H), 7.22 - 7.15 (m, 2H), 6.94 - 6.86 (m, 2H), 3.82 (s, 3H), 3.44 (d, J = 8.3 Hz, 1H), 2.83 (d, J= 8.4 Hz, 1H); 13 C NMR (101 MHz, CDCl3) δ 172.23, 159.52, 129.77, 124.17, 114.00, 62.40, 55.31, 40.37, 36.97;ESIMS m / z 260 ([MH] - ).

[0498] trans-3-(4-bromo-3-chlorophenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (C213) [ka] Isolated as a brown solid (0.186 g, 60%): 1 H NMR (400 MHz, CDCl3) δ 7.63 (d, J = 8.3 Hz, 1H), 7.40 - 7.32 (m, 1H), 7.04 (ddd, J = 8.3, 2.2, 0.7 Hz, 1H), 3.42 (d, J = 8.3 Hz, 1H), 2.86 (d, J = 8.3 Hz, 1H); 13 C NMR (101 MHz, CDCl3) δ 171.39, 134.91, 133.89, 133.08, 130.54, 128.16, 122.61, 61.39, 39.70, 37.14;ESIMS m / z 342.8 ([MH] - ).

[0499] trans-3-(3-bromo-4-chlorophenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (C214) [ka] Isolated as a tan solid (0.7577 g, 71%): 1 H NMR (400 MHz, CDCl3) δ 7.53 (d, J = J = 2.1 Hz, 1H), 7.47 (d, J = 8.3 Hz, 1H), 7.17 (dd, J = 8.3, 2.1 Hz, 1H), 3.44 (d, J = 8.3 Hz, 1H), 2.86 (d, J = 8.3 Hz, 1H); 13 C NMR (101 MHz, CDCl3) δ 171.40, 134.73, 133.87, 132.39, 130.43, 128.70, 122.74, 61.50, 39.53, 37.14 ESIMS m / z 342.7 ([M-H] - ).

[0500] trans-3-(3-bromo-5-chlorophenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (C215) [ka] Isolated as a tan solid (0.9102 mg, 40%): 1 H NMR (400 MHz, acetone-d6) δ 7.67 (d, J= 1.6 Hz, 1H), 7.63 (s, 1H), 7.57 (d, J= 1.8 Hz, 1H), 3.53 (d, J = 8.5 Hz, 1H), 3.38 (d, J = 8.5 Hz, 1H); 13 C NMR (101 MHz, acetone-d6) δ 166.92 138.16, 135.69, 131.59, 131.55, 129.10, 123.23, 62.52, 39.41, 37.85;ESIMS m / z 342.7 ([MH] - )].

[0501] trans-2,2-dichloro-3-(3-chloro-5-(difluoromethyl)phenyl)cyclopropane-1-carboxylic acid (C216) [ka] Isolated as an off-white solid (2.6 g, 63%): 1 H NMR (300 MHz, CDCl3) showed no COOH signal, δ 7.49 (s, 1H), 7.38 (s, 1H), 7.30 (s, 1H), 6.63 (t, J = 56.0 Hz, 1H), 3.50 (d, J = 8.4 Hz, 1H), 2.91 (d, J = 8.0 Hz, 1H); 19 F NMR (282.2 MHz, CDCl3) δ -112.04;ESIMS m / z313 ([MH] - ).

[0502] trans-2,2-dichloro-3-(4-chloro-3-(difluoromethyl)phenyl)cyclopropane-1-carboxylic acid (C217) [ka] Isolated as an off-white solid (6.2 g, 69%): 1 H NMR (400 MHz, CDCl3) δ 10.5 (br s, 1H), 7.55 (s, 1H), 7.46 (d, J= 8.0 Hz, 1H), 7.34 (d, J = 8.4 Hz, 1H), 6.95 (t, J = 54.8 Hz, 1H), 3.50 (d, J = 8.4 Hz, 1H), 2.91 (d, J = 8.4 Hz, 1H); 19 F NMR (376.2 MHz, CDCl3) δ -115.52;ESIMS m / z313 ([MH] - ).

[0503] trans-2,2-dichloro-3-(3-(difluoromethyl)-5-fluorophenyl)cyclopropane-1-carboxylic acid (C218) [ka] Isolated as an off-white solid (5 g, 38%): 1 H NMR (400 MHz, CDCl3)COOH No signal was observed, and the peaks were δ 7.23 - 7.21 (m, 2H), 7.11 (d, J = 8.8 Hz, 1H), 6.64 (t, J = 55.6 Hz, 1H), 3.51 (d, J = 8.4 Hz, 1H), 2.91 (d, J = 8.0 Hz, 1H); 19 F NMR (376.2 MHz, CDCl3) δ -110.37;ESIMS m / z 297.19 ([MH] - ).

[0504] trans-2,2-dichloro-3-(3-(difluoromethyl)-4-fluorophenyl)cyclopropane-1-carboxylic acid (C219) [ka] Isolated as an off-white solid (6.0 g, 77%): 1 H NMR (400 MHz, CDCl3) showed no COOH signal and δ 7.49 (d, J = 6.0 Hz, 1H), 7.40 (br s, 1H), 7.17 (t, J = 9.2 Hz, 1H), 6.90 (t, J = 54.8 Hz, 1H), 3.49 (d, J = 8.0 Hz, 1H), 2.89 (d, J = 8.4 Hz, 1H); 19 F NMR (376.2 MHz, CDCl3) δ -114.47, -119.69;ESIMS m / z 297 ([MH] - ).

[0505] trans-2,2-dichloro-3-(3-chloro-4-(difluoromethyl)phenyl)cyclopropane-1-carboxylic acid (C220) [ka] Isolated as an off-white solid (3.5 g, 42%): 1 H NMR (400 MHz, CDCl3) showed no COOH signal, δ 7.68 (d, J = 7.6 Hz, 1H), 7.35 (s, 1H), 7.29 (d, J = 8.4 Hz, 1H), 6.94 (t, J = 54.8 Hz, 1H), 3.48 (d, J = 8.4 Hz, 1H), 2.91 (d, J = 8.4 Hz, 1H); 19 F NMR (376.2 MHz, CDCl3) δ -115.46;ESIMS m / z 313 ([MH] - ).

[0506] trans-2,2-dichloro-3-(4-(difluoromethyl)-3-fluorophenyl)cyclopropane-1-carboxylic acid (C221) [ka] Isolated as an off-white solid (4.4 g, 77%): 1 H NMR (400 MHz, CDCl3) δ 7.62 (t, J = 7.6 Hz, 1H), 7.18 (d, J = 7.6 Hz, 1H), 7.06 (d, J = 10.0 Hz, 1H), 6.89 (t, J = 54.8 Hz, 1H), 3.50 (d, J = 8.4 Hz, 1H), 2.90 (d, J = 8.4 Hz, 1H); 19 F NMR (376.2 MHz, CDCl3) δ -114.42, -118.63;ESIMS m / z297.15 ([MH] - ).

[0507] trans-2,2-dichloro-3-(3-(difluoromethyl)phenyl)cyclopropane-1-carvone Acid (C222) [ka] Isolated as an off-white solid (6.2 g, 53%): 1 H NMR (300 MHz, CDCl3) δ 7.49 (br s, 2H), 7.41 (br s, 2H), 6.66 (t, J = 56.0 Hz, 1H), 3.53 (d, J = 8.4 Hz, 1H), 2.92 (d, J = 8.0 Hz, 1H); 19 F NMR (282.2 MHz, CDCl3) δ -111.20;ESIMS m / z 279.20 ([MH] - ).

[0508] trans-2,2-dichloro-3-(4-(difluoromethyl)phenyl)cyclopropane-1-carvone Acid (C223) [ka] Isolated as an off-white solid (7 g, 61%): 1 H NMR (300 MHz, CDCl3) δ 7.53 (d, J = 8.0 Hz, 2H), 7.37 (d, J = 8.0 Hz, 2H), 6.66 (t, J = 56.4 Hz, 1H), 3.52 (d, J = 8.4 Hz, 1H), 2.92 (d,J = 8.0Hz, 1H); 19 F NMR (282.2 MHz, CDCl3) δ -112.20;ESIMS m / z 279.30 ([MH] - ).

[0509] trans-3-(4-bromo-3,5-difluorophenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (C224) [ka] Isolated as a white solid (2.13 g, 72%): mp 178.3°C-188.6°C; 1 H NMR (400 MHz, CDCl3) δ 6.90 (d, J = 7.1 Hz, 2H), 3.43 (d, J= 8.2 Hz, 1H), 2.86 (d, J = 8.2 Hz, 1H); 19 F NMR (376 MHz, CDCl3) δ -103.87;ESIMS m / z 344.7 ([MH] - ).

[0510] trans-3-(4-bromo-3-fluoro-5-methoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (C225) [ka] Isolated as an oily solid (0.43 g, 37%): 1 H NMR (400 MHz, CDCl3) δ 6.70 - 6.64 (m, 1H), 6.61 (d, J = 1.6 Hz, 1H), 3.95 (s, 3H), 3.44 (d, J = 8.3 Hz, 1H), 2.86 (d, J = 8.3 Hz, 1H); 19 F NMR (376 MHz, CDCl3) δ -104.22;ESIMS m / z 356.7 ([MH] - ).

[0511] trans-3-(3-bromo-5-fluoro-4-methoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (C226) [ka] Isolated as a brown oil (0.24 g, 65%): 1 H NMR (400 MHz, CDCl3) δ 7.24 (d, J = 7.9 Hz, 1H), 6.87 (d, J= 11.3 Hz, 1H), 3.91 (d, J = 3.8 Hz, 3H), 3.44 (d, J = 8.3 Hz, 1H), 2.80 (d, J = 8.3 Hz, 1H); 19 F NMR (376 MHz, CDCl3) δ -135.11;ESIMS m / z 356.7 ([MH] - ).

[0512] trans-2,2-dichloro-3-(3,5-difluoro-4-methoxyphenyl)cyclopropane-1-carboxylic acid (C227) [ka] Isolated as a tan solid (0.440 g, 53%): 1H NMR (400 MHz, CDCl3) δ 10.72 (s, 1H), 6.89 - 6.77 (m, 2H), 4.02 (t, J = 1.2 Hz, 3H), 3.39 (d, J = 8.3 Hz, 1H), 2.80 (d, J = 8.3 Hz, 1H); 19 F NMR (376 MHz, CDCl3) δ -127.43, -127.43, -127.44;ESIMS m / z 296 ([MH] - ).

[0513] Cis / trans-2,2-dichloro-3-(3,4,5-trifluorophenyl)cyclopropane-1-carboxylic acid (C228) [ka] Isolated as a white solid (0.411 g, 53%): 1 H NMR (400 MHz, CDCl3) δ 7.72 (s, 1H), 7.06 - 6.74 (m, 2H), 3.46 - 3.23 (m, 1H), 3.01 - 2.74 (m, 1H); 19 F NMR (376 MHz, CDCl3) δ -132.88, -132.94, -133.81, -133.87, -159.60, -159.65, -159.71, -160.34, -160.39, -160.45;ESIMS m / z 284 ([MH] - ). The following compounds were prepared in a manner similar to the procedure outlined in Example 3:

[0514] trans-2-chloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)thiophene N (C229) [ka] Isolated as a deep orange oil (0.455 g, 68%): 1H NMR (400 MHz, CDCl3) δ 7.25 (d, J = 9.5 Hz, 2H), 6.92 (d, J= 8.8 Hz, 2H), 6.83 (d, J = 3.8 Hz, 1H), 6.80 (d, J = 3.5 Hz, 1H), 3.83 (s, 3H), 3.10 (s, 2H); 13 C NMR (101 MHz, CDCl3) δ 159.40, 136.68, 129.87, 129.36, 126.30, 126.04, 125.59, 113.96, 65.28, 55.32, 41.23, 34.95.

[0515] trans-2-((2,2-dichloro-3-methyl-3-(4-(trifluoromethoxy)phenyl)cyclopropane) (propyl)methoxy)tetrahydro-2H-pyran (C230) [ka] Isolated as a pale yellow liquid (3.3 g, 77%): 1 H NMR (400 MHz, CDCl3) δ 7.38 - 7.32 (m, 2H), 7.22 - 7.16 (d, J = 8.4 Hz, 2H), 4.72 (dt, J = 17.0, 3.3 Hz, 1H), 4.13 (dd, J = 11.2, 6.6 Hz, 0.5H), 4.00 - 3.82 (m, 2H), 3.63 (dd, J = 11.3, 7.4 Hz, 0.5H), 3.60 - 3.52 (m, 1H), 2.20 (dt, J = 11.6, 4.5 Hz, 1H), 1.94 - 1.82 (m, 1H), 1.82 - 1.71 (m, 1H), 1.71 - 1.55 (m, 4H), 1.52 (d, J= 5.9 Hz, 3H); 19 F NMR (376 MHz, CDCl3) δ -57.85; 13C NMR (101 MHz, CDCl3) δ 148.26, 141.31, 130.14, 124.32, 121.77, 120.89, 119.21, 116.65, 99.17, 99.08, 67.92, 63.87, 63.77, 62.41, 37.91, 37.83, 36.92, 36.82, 30.74, 25.45, 19.93, 19.88, 19.48, 19.44;ESIMS m / z 441.4 (M + CH3CN) ;IR (thin film) 1257, 1222, 1208, 1163 cm -1 .

[0516] trans-1-chloro-3-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-5-(difluoromethyl) (fluoromethyl)benzene (C231) [ka] Isolated as a yellow liquid (11.5 g, 69%): 1 H NMR (300 MHz, CDCl3): δ 7.47 (s, 2H), 7.39 (s, 1H), 7.28 (d, J = 8.7 Hz, 2H), 6.93 (d, J = 8.7 Hz, 2H), 6.64 (t, J = 56.1 Hz, 1H), 3.83 (s, 3H), 3.16 (q, J= 8.7 Hz, 2H).

[0517] trans-1-chloro-4-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-2-(difluoromethyl) (fluoromethyl)benzene (C232) [ka] Isolated as an off-white solid (10.7 g, 83%): 1H NMR (400 MHz, CDCl3) δ 7.65 (s, 1H), 7.46 - 7.41 (m, 2H), 7.28 (d, J = 8.4 Hz, 2H), 7.10 - 6.83 (m, 3H), 3.83 (s, 3H), 3.18- 3.13 (m, 2H).

[0518] trans-1-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-3-(difluoromethyl)-5-fluorobenzene (C233) [ka] Isolated as an off-white solid (16.5 g, 64%): 1 H NMR (400 MHz, CDCl3) δ 7.29 (d, J = 8.8 Hz, 2H), 7.20 (d, J = 8.8 Hz, 2H), 6.93 (d, J = 8.8 Hz, 2H), 6.65 (t,J = 56.0 Hz, 2H), 3.83 (s, 3H), 3.16 (s, 2H).

[0519] trans-4-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-2-(difluoromethyl) (C234)-1-fluorobenzene [ka] Isolated as an off-white solid (10.0 g, 55%): ESIMS m / z 374 ([M+H] + ).

[0520] trans-2-chloro-4-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-1-(difluoromethyl) (fluoromethyl)benzene (C235) [ka] Isolated as an off-white solid (10.0 g, 34%): 1 H NMR (400 MHz, CDCl3) δ 7.68 (d, J = 8.0 Hz, 1H), 7.43 (s, 1H), 7.38 (d, J = 8.4 Hz, 1H), 7.28 - 7.25 (m, 2H), 7.09 - 6.92 (m, 3H), 3.83 (s, 3H), 3.15 (q, J = 12.0 Hz, 2H);ESIMS m / z376 ([M+H] + ).

[0521] trans-2-fluoro-4-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-1-(di Fluoromethyl)benzene (C236) [ka] Isolated as a pale yellow liquid (6.9 g, 58%): 1 H NMR (400 MHz, CDCl3) δ 7.31 (t, J = 7.6 Hz, 1H), 7.27 (d, J = 9.2 Hz, 2H), 7.14 (d,J = 10.8 Hz, 1H), 7.04 - 6.76 (m, 4H), 3.83 (s, 3H), 3.16 (t, J = 8.8 Hz, 2H); 19 F NMR (376.2 MHz, CDCl3) δ -114.14, -114.32, -119.30.

[0522] trans-1-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropyl)-3-(difluoromethyl)benzene (C237) [ka] Isolated as an off-white solid (6.3 g, 95%): 1H NMR (400 MHz, CDCl3) δ 7.50 (br s, 4H), 7.29 (d, J = 8.8 Hz, 2H), 6.93 (d, J = 8.0 Hz, 2H), 6.67 (t, 1H), 3.83 (s, 3H), 3.19 (s, 2H); 19 F NMR (376.2 MHz, CDCl3) δ -110.87, -111.02.

[0523] trans-1-(2,2-dichloro-3-(4-(difluoromethyl)phenyl)cyclopropyl)-4-meth C238 Benzene [ka] Isolated as a white solid (14 g, 69%): 1 H NMR (400 MHz, CDCl3) δ 7.54 (d, J = 8.0 Hz, 2H), 7.46 (d, J = 8.0 Hz, 2H), 7.28 (t, J = 8.4 Hz, 2H), 6.93 (d, J = 8.0 Hz, 2H), 6.67 (t, J = 56.8 Hz, 1H), 3.83 (s, 3H), 3.18 (s, 2H). The following compounds were prepared in a manner similar to the procedure outlined in Example 12:

[0524] 2-chloro-5-((1R,3R)-2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)benzoic acid (C239) [ka] Isolated as a grey solid (3.80 g, 96%): 1H NMR (300 MHz, DMSO-d6) δ 13.48 (s, 1H), 10.90 (s, 1H), 8.15 (d, J = 2.6 Hz, 1H), 7.78 (dd, J = 8.8, 2.7 Hz, 1H), 7.63 (t, J = 1.9 Hz, 1H), 7.57 - 7.50 (m, 3H), 3.62 (d, J = 8.5 Hz, 1H), 3.49 (d, J = 8.5 Hz, 1H);ESIMS m / z 454 ([M+H] + ).

[0525] 2-chloro-5-((1R,3R)-2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-carboxamido)benzoic acid (C240) [ka] Isolated as a grey solid (3.70 g, 98%): 1 H NMR (300 MHz, DMSO-d6) δ 13.47 (s, 1H), 10.95 (s, 1H), 8.16 (d, J = 2.7 Hz, 1H), 7.82 - 7.73 (m, 2H), 7.69 (d, J = 8.3 Hz, 1H), 7.53 (d, J = 8.7 Hz, 1H); 7.43 (dd, J = 8.5, 2.1 Hz, 1H), 3.60 (d, J = 8.5 Hz, 1H), 3.45 (d, J = 8.5 Hz, 1H) + ).

[0526] 2-Chloro-5-((1R,3R)-2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamido)benzoic acid (C241) [ka] Isolated as a grey solid (3.60 g, 99%): 1H NMR (400 MHz, DMSO-d6) δ 13.44 (s, 1H), 10.91 (s, 1H), 8.16 (d, J = 2.7 Hz, 1H), 7.80 - 7.76 (m, 3H), 7.54 (d, J = 8.7 Hz, 1H), 3.63 (dt, J = 8.5, 0.7 Hz, 1H), 3.52 (d, J = 8.5 Hz, 1H);ESIMS m / z 488 ([M+H] + ).

[0527] 2-chloro-5-((1R,3R)-2,2-dichloro-3-(3-chloro-4-fluorophenyl)cyclopropane-1-carboxamido)benzoic acid (C242) [ka] Isolated as a grey solid (3.80 g, 99%): 1 H NMR (400 MHz, DMSO-d6) δ 13.48 (s, 1H), 10.93 (s, 1H), 8.16 (d, J = 2.6 Hz, 1H), 7.78 (dd, J = 8.8, 2.7 Hz, 1H), 7.71 (dd, J = 7.2, 2.0 Hz, 1H), 7.53 (d, J = 8.7 Hz, 1H), 7.50 - 7.42 (m, 2H), 3.58 (d, J = 8.4 Hz, 1H), 3.42 (d, J = 8.5 Hz, 1H); 19 F NMR (376 MHz, DMSO-d6) δ -117.29;ESIMS m / z438 ([M+H] + ).

[0528] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichloro-4-methoxyphenyl)cyclopropane Pan-1-carboxamido)benzoic acid (C243) [ka] Isolated as a cream-colored solid (1.565 g, 90%): mp 227°C-231°C; 1 H NMR (400 MHz, DMSO-d6) δ 13.48 (s, 1H), 10.89 (s, 1H), 8.16 (d, J = 2.4 Hz, 1H), 7.78 (dd, J = 8.7, 2.4 Hz, 1H), 7.61 (s, 2H), 7.53 (d, J = 8.7 Hz, 1H), 3.84 (s, 3H), 3.57 (d, J= 8.4 Hz, 1H), 3.45 (d, J = 8.5 Hz, 1H); 13 C NMR (101 MHz, DMSO-d6) δ 166.27, 162.66, 151.18, 137.58, 131.44, 131.42, 131.22, 129.72, 128.18, 125.90, 122.87, 121.16, 62.19, 60.64, 38.51, 36.44;HRMS-ESI (m / z) [M+] + C 18 H 12 Calculated for Cl5NO4: 480.9209; Found: 480.9216.

[0529] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-4-fluorophenyl)cyclopropane-1-carboxamido)benzoic acid (C244) [ka] Isolated as a white solid (6.589 g, 93%): 207°C-210°C; 1 H NMR (400 MHz, DMSO-d6) δ 13.50 (s, 1H), 10.95 (s, 1H), 8.18 (d, J = 2.5 Hz, 1H), 7.80 (dd, J = 8.7, 2.5 Hz, 1H), 7.71 (d, J = 7.2 Hz, 1H), 7.51 (dd, J = 28.2, 8.8 Hz, 3H), 3.59 (d, J = 8.4 Hz, 1H), 3.43 (d, J = 8.5 Hz, 1H); 13 C NMR (101 MHz, DMSO-d6) δ 166.22, 162.68, 158.01, 155.55, 137.53, 131.37, 131.17, 131.00, 130.95, 130.91, 129.74, 129.67, 125.86, 122.82, 121.12, 119.49, 119.32, 116.91, 116.70, 62.21, 38.49, 36.58; 19 F NMR (376 MHz, DMSO-d6) δ -117.26;ESIMS m / z 438 ([M+H] + ).

[0530] trans-2,3-dichloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1- Carboxamido)benzoic acid (C245) [ka] Isolated as a tan solid (1.685 g, 79%): mp 231°C-235°C; 1 H NMR (400 MH z, DMSO-d6) 13.82 (s, 1H), 11.05 (s, 1H), 8.13 (d, J = 2.4 Hz, 1H), 7.97 (d, J = 2.4 Hz, 1H), 7.63 (s, 1H), 7.56 (s, 2H), 3.63 (d, J= 8.5 Hz, 1H), 3.50 (d, J = 8.5 Hz, 1H); 13 C NMR (101 MHz, DMSO-d6) δ 165.84, 162.96, 138.00, 137.09, 134.14, 133.98, 133.01, 127.83, 127.64, 123.41, 122.15, 119.27, 61.94, 38.37, 36.78;HRMS-ESI (m / z) [M+] + C 17Calculated value for H9Cl6NO3: 484.8714; found: 484.8711.

[0531] trans-2,4-dichloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1- Carboxamido)benzoic acid (C246) [ka] Isolated as a pale yellow solid (0.855 g, 42%): mp 263°C-266°C; 1 H NMR (500 MHz, DMSO-d6) δ 13.67 (s, 1H), 10.37 (s, 1H), 8.37 (s, 1H), 7.85 (s, 1H), 7.63 (s, 1H), 7.53 (d, J = 1.6 Hz, 2H), 3.82 (d, J = 8.6 Hz, 1H), 3.63 (d, J = 8.5 Hz, 1H); 13 C NMR (126 MHz, DMSO-d6) δ 165.41, 163.35, 137.17, 133.95, 133.66, 131.17, 129.96, 128.80, 128.24, 127.74, 127.60, 126.63, 62.37, 37.24, 37.09;HRMS-ESI (m / z) [M+] + C 17 Calculated value for H9Cl6NO3: 484.8714; found: 484.8715. The following compounds were prepared in a manner similar to the procedure outlined in Example 13:

[0532] trans-2-chloro-5-(2,2-dibromo-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2,6-difluorophenyl)benzamide (F162) [ka] Isolated as an off-white solid (0.045 g, 38%).

[0533] trans-N-(4-(1H-1,2,3-triazol-1-yl)phenyl)-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamide)benzamide (F217) [ka] Isolated as an off-white solid (0.062 g, 44%)

[0534] trans-tert-butyl(4-(3-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamido)benzamido)-3-methylphenyl)carbamate (F262) [ka] Isolated as a yellow foam (0.043 g, 27%)

[0535] trans-tert-butyl(4-(3-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-carboxamido)benzamido)-3-methylphenyl)carbamate (F263) [ka] Isolated as a pale yellow foam (0.043 g, 27.2%).

[0536] trans-N-(4-(1H-pyrazol-1-yl)phenyl)-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarboxamide)benzamide (F440) [ka] Isolated as a cream solid (0.310 g, 63%).

[0537] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-(oxazol-2-yl)phenyl)benzamide (F446) [ka] Isolated as an off-white solid (0.203 g, 58.4%).

[0538] trans-2-chloro-5-(2,2-dibromo-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluorophenyl)-N-methylbenzamide (PF7) [ka] Isolated as an off-white glass (0.050 g, 29.6%).

[0539] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(5-(trifluoromethyl)-1H-pyrazol-3-yl)benzamide (PF138) [ka] Isolated as an off-white solid (0.092 g, 45.1%).

[0540] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)benzamide (PF139) [ka] Isolated as a colorless glass (0.008 g, 6.37%).

[0541] trans-2-chloro-N-(4-chloropyridin-2-yl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl)- (phenyl)cyclopropane-1-carboxamido)benzamide (PF140) [ka] Isolated as a colorless glass (0.008 g, 6.37%).

[0542] trans-2-chloro-N-(6-chloropyridazin-3-yl)-5-(2,2-dichloro-3-(3,5-dichloro) Phenyl)cyclopropane-1-carboxamido)benzamide (PF148) [ka] Isolated as a deep red glass (0.0177 g, 14%).

[0543] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-5-fluorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (PF1) [ka] Isolated as a pale yellow oil (0.076 g, 51%).

[0544] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-5-fluorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (PF2) [ka] Isolated as a white foam (0.118 g, 77%).

[0545] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-4-fluorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (PF4) [ka] Isolated as a white foam (0.094 g, 67%).

[0546] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-4-fluorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (PF5) [ka] Isolated as a pale yellow oil (0.097 g, 63%).

[0547] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarboxamido)-2-ethyl-N-(4-fluorophenyl)benzamide (PF8) [ka] Isolated as a clear film (0.103 g, 54.9%).

[0548] trans-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropanecarboxamide)-N -(4-Fluorophenyl)-2-vinylbenzamide (PF9) [ka] Isolated as a pale yellow film (0.051 g, 20%).

[0549] trans-2-chloro-5-(2,2-dichloro-3-methyl-3-(4-(trifluoromethoxy)phenyl) Cyclopropanecarboxamido)-N-(4-fluorophenyl)benzamide (PF32) [ka] Isolated as a white solid (0.017 g, 42%).

[0550] trans-2-chloro-5-(2,2-dichloro-3-(4-chloro-3-fluorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)benzamide (PF34) [ka] Isolated as a pale yellow oil (0.134 g, 95%).

[0551] trans-2-chloro-5-(2,2-dichloro-3-(4-chloro-3-fluorophenyl)cyclopropane-1-carboxamido)-N-(4-fluorophenyl)-N-methylbenzamide (PF35) [ka] Isolated as a white foam (0.101 g, 70%).

[0552] trans-5-(3-(3-bromo-5-chlorophenyl)-2,2-dichlorocyclopropane-1-carboxamide 2-chloro-N-(4-fluorophenyl)-N-methylbenzamide (PF38) [ka] Isolated as a colorless oil (0.067 g, 64%).

[0553] trans-N-(4-acetamido-2-fluorophenyl)-2-chloro-5-(2,2-dichloro-3-(3,5- Dichlorophenyl)cyclopropane-1-carboxamido)benzamide (PF40) [ka] Isolated as a pale yellow solid (0.043 g, 31%).

[0554] trans-N-(4-acetamido-2-fluorophenyl)-2-chloro-5-(2,2-dichloro-3-(3,4- Dichlorophenyl)cyclopropane-1-carboxamido)benzamide (PF41) [ka] Isolated as a light brown solid (0.078 g, 55%).

[0555] trans-N-(4-acetamido-2-fluorophenyl)-2-chloro-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1-carboxamide)benzamide (PF42) [ka] Isolated as a white solid (0.085 g, 63%).

[0556] trans-2-chloro-5-(2,2-dichloro-3-(3,4-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluoro-2-methylphenyl)benzamide (PF46) [ka] Isolated as a white solid (0.092 g, 78%).

[0557] trans-2-chloro-5-(2,2-dichloro-3-(3,4,5-trichlorophenyl)cyclopropane-1- Carboxamido)-N-(4-fluoro-2-methylphenyl)benzamide (PF47) [ka] Isolated as a white solid (0.094 g, 75%).

[0558] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-4-fluorophenyl)cyclopropane-1-carboxamido)-N-(4-fluoro-2-methylphenyl)benzamide (PF48) [ka] Isolated as a white solid (0.077 g, 68%).

[0559] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-fluoro-2-methylphenyl)-N-methylbenzamide (PF49) [ka] Isolated as a white solid (0.084 g, 69%).

[0560] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-4-fluorophenyl)cyclopropane-1-carboxamido)-N-(4-fluoro-2-methylphenyl)-N-methylbenzamide (PF50) [ka] Isolated as a pale yellow glass (0.087 g, 73%).

[0561] trans-2-chloro-5-(2,2-dichloro-3-(4-methoxyphenyl)cyclopropane-1-carbohydrate oxamido)-N-(4-fluorophenyl)benzamide (PF65) [ka] Isolated as a white solid (0.052 g, 35.3%).

[0562] trans-2-chloro-5-(2,2-dichloro-3-(4-isopropylphenyl)cyclopropanecarboxamide)-N-(4-fluorophenyl)benzamide (PF66) [ka] Isolated as a white solid (0.051 g, 31.8%).

[0563] trans-2-chloro-N-(2-cyano-4-fluorophenyl)-5-(2,2-dichloro-3-(3,5-dichloro)phenyl)- (phenyl)cyclopropane-1-carboxamido)benzamide (PF67) [ka] Isolated as a white foam (0.114 g, 85%).

[0564] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(2,3,4-trifluorophenyl)benzamide (PF68) [ka] Isolated as a white solid (0.118 g, 87%).

[0565] trans-2-chloro-N-(2-cyanophenyl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl) Cyclopropane-1-carboxamido)benzamide (PF72) [ka] Isolated as a white solid (0.104 g, 80%).

[0566] trans-2-chloro-5-(2,2-dichloro-3-(3,5-dichlorophenyl)cyclopropane-1-chlor Voxamido)-N-(4-(trifluoromethyl)thiazol-2-yl)benzamide (PF134) [ka] Isolated as a white foam (0.096 g, 48%).

[0567] trans-2-chloro-N-(5-chloropyridin-2-yl)-5-(2,2-dichloro-3-(3,5-dichlorophenyl)- (phenyl)cyclopropane-1-carboxamido)benzamide (PF141) [ka] Isolated as a yellow foam (0.068 g, 43%).

[0568] trans-N-(4-acetamido-2-methylphenyl)-2-chloro-5-(2,2-dichloro-3-(3,5-di Chlorophenyl)cyclopropane-1-carboxamido)benzamide (PF158) [ka] Isolated as a white solid (0.051 g, 37%).

[0569] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-5-fluorophenyl)cyclopropane-1-carboxamido)-N-(2,6-difluorophenyl)benzamide (F160) [ka] Isolated as a white foam (0.064 g, 41%).

[0570] trans-2-chloro-5-(2,2-dichloro-3-(3-chloro-4-fluorophenyl)cyclopropane-1-carboxamido)-N-(2,6-difluorophenyl)benzamide (F161) [ka] Isolated as a white foam (0.031 g, 20%).

[0571] trans-2-chloro-5-(2,2-dichloro-3-(4-chloro-3-fluorophenyl)cyclopropane-1-carboxamido)-N-(2,6-difluorophenyl)benzamide (F163) [ka] Isolated as a white foam (0.052 g, 36%).

[0572] trans-5-(3-(3-bromo-5-chlorophenyl)-2,2-dichlorocyclopropane-1-carboxamide N-(2,6-difluorophenyl)-2-chloro-N-(2,6-difluorophenyl)benzamide (F164) [ka] Isolated as a white solid (0.018 g, 17%).

[0573] trans-2-chloro-N-(2-cyano-4-fluorophenyl)-5-(2,2-dichloro-3-(3,4-dichloro)phenyl)- (triphenyl)cyclopropane-1-carboxamido)benzamide (F190) [ka] ...

Claims

1. The table below 【change】 【change】 【change】 【change】 【change】 and a carrier and / or an active ingredient, an active ingredient selected from a miticide, algicide, antifeedant, birdcide, bactericide, bird repellent, chemosterilant, fungicide, herbicide safener, herbicide, insect attractant, insect repellent, insecticide, mammalian repellent, mating disruptant, molluscicide, nematicide, plant activator, plant growth regulator, rodenticide, synergist, and antiviral; or an active ingredient selected from AIGA, AI-1, AI-2, or AIGA-2; or further comprising lotilaner, a molecule selected from Table A, or a biopesticide; Here, AIGA collectively refers to the following substances: (1) (3-ethoxypropyl)mercury bromide, 1,2-dibromoethane, 1,2-dichloroethane Benzene, 1,2-dichloropropane, 1,3-dichloropropene, 1-MCP, 1-methylcyclopropene, 1-naphthol, 2-(octylthio)ethanol, 2,3,3-TPA, 2,3,5-triiodobenzoic acid, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4,5-TP, 2,4-D, 2,4-DB, 2,4-DEB, 2,4-DEP, 2,4-DES, 2,4-DP, 2,4-MCPA, 2,4-MCPB, 2iP, 2-methoxyethylmercury chloride, 2-phenylphenone alcohol, 3,4-DA, 3,4-DB, 3,4-DP, 3,6-dichloropicolinic acid, 4-aminopyridine, 4-CPA, 4-CPB, 4-CPP, 4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate , 8-phenylmercuryoxyquinoline, abamectin, abamectin-aminomethyl, abscisic acid, ACC, acephate, acequinocyl, acetamiprid, acetione (acethion), acetochlor, acetophenate, acetophenone Acetophos, acetoprole, acibenzolar, acifluorfen, aclonifen, ACN, acrep, ac Linatrin, acrolein, acrylonitrile, acypetacs, afidopyropen, afoxolaner, alachlor, alanap, alanycarb, albendazo aldicarb, aldicarb sulfone, aldimorph, aldoxy Carb, Aldrin, Allethrin, Allicin, Allidochlor, Allosamiji , alloxydim, allyl alcohol, alixycarb, arorac, alpha-cypermethrin, alpha-endosulfan, alphamethrin, altretamine, aluminum phosphide, aluminum phosphide, ametoctrazine, ametridione, ametryn, ametryne, amivudine, amicarbazone, a Micarthiazol, amidithione, amidoflumet, amidosulfuron, aminocarb, aminocyclopyrachlor, aminopyralid, amino Triazole, amiprofos-methyl, amiprophos ), amiprophos-methyl, amisulbrom, amiton, amitraz, amitrole, ammonium sulfamate , Ambam, amorphous silica gel, amorphous silicon dioxide, ampropylfos, AMS, anabasine, ancymidol, anilazine, anilo Anilofos, anisuron, anthraquinone, antu, apholate, alamite, alprocarb, arsenous acid, asomate (asomate), aspirin, ashram, athidathion, atraton, atrazine, aureofungin, avermectin B1, AVG, Aviglycine, azaconazole, azadirachtin, azafenidin, azamethiphos, azidithiophene azidithion, azimsulfuron, azinphos ethyl, azinphos-ethyl, azinphos methyl, azinphos-methyl, adiprothrin, adiprothrin, aziprotryne, azithiram, azobenzene, azocyclotin, azothoate, azoxystrobin, bachmedesh, barban, barbanate, barium hexafluorosilicate, Barium polysulfide, barium silicofluoride, Bartholin, basic copper carbonate, basic copper chloride, basic copper sulfate, BCPC, beflubutamide, benalaxyl, benalaxyl-M, benazolin, bencarbazone, benclothiaz, bendaqingbingzhi, bendiocarb, bendioxide, benefin, benfluralin, benfuracarb, benfuresate, benmifa Benmihuangcaoan, benodanil, benomyl, benoxacor, benoxafos, benquinox, bensulfuron, bensulide, bensultap, bentaluron, bentazon, bentazon, bentazon, benthazone, benthiavalicarb, benthiazole, bentiocarb, benthiocarb, Bentranil, benzadox, benzalkonium chloride, benzamacril, benzamizole, benzamorph, benzene hexachloride, benzfendizone, benzimine, benzipram, benzobicyclon, benzoepin, benzofenap, benzofluo benzofluor, benzohydroxamic acid, benzomate, benzophosph benzophosphate, benzothiadiazole, benzovindiflupyr, benzoximate, benzoylprop, benzthiazuron, benzocaotong, benzyl benzoate, benzyladenine, berberine, beta-cyfluthrin, beta-cypermethrin, bethoxazin, BHC, bialaphos, bicyclopyrone, bifenazate, bifenox, bifenol Entrin, bifujunzhi, bilanafos, binapacryl, Bingqingxiao, bioallethrin, bioethanomethrin, biopermethrin, bioresmetry phenanthrene, biphenyl, bisazir, bismerthiazol, bismerthiazol-copper, bisphenylmercury methylenedi(x-naphthalene-y-sulphonate), bispyribac, bistrifluron, bisultap, bitertanol, bithionol, bixafen, blasticidin-S, borax Lux, Bordeaux mixture, boric acid, boscalid, BPPS, brassinolide, brassinolide-ethyl, brevicomin, brodifacoum, brofenprox, brofenvalerate, broflanilide, brofluthrinate, bro Romacil, bromadiolone, bromchlophos, bromethalin, bromethrin, bromfenvinphos, bromoacetamide, bromobonil, bromobutide, bromociclen, bromocyclen, bromo-DDT, bromofenoxim, bromophos, bromomethane, bromophos, bromophos-ethyl, bromopropylate, bromothalonil, brom Lomoxynil, brompyrazone, bromuconazole, Bronopol, BRP, BTH, bucarpolate, bufencarb, buminafos, bupirimate, buprofezin, bulga Ndi mixture, busulfan, busulphan, butacarb, butachlor, butafenacil, butam, butamifos, butane-fipronil, butathiofos , butenachlor, butene-fipronil, butethrin, Buthidazole, buthibate, buthiuron, butifos, butocarboxim, butonate , butopyronoxyl, butoxycarboxim, Butralin, butrizol, butroxydim, buturon, butylamine, butyrate, butylchlorophos, butylene-fipronil, cacodylic acid, cadusafos, cafenstrole, calcife roll, calcium arsenate, calcium chlorate, calcium cyanamide, calcium cyanide, calcium polysulfide, calvinphos , cambendichlor, camphechlor, camphor, captafol, captan, carbam, carbamorph, carbanolate, carbaryl, carbaryl ), carbasulam, carbathion, carbendazim, carbendazol, carbetamide, carbophenothion, carbofuran, carbon disulfide, carbon tetrachloride, carbonyl sulfide, carbophen Notion, carbophos, carbosulfan, carboxazole, carboxide, carboxin, carfentrazone, carpropami Do, cartap, carvacrol, carvone, CAVP, CDAA, CDEA, CDEC, Cellocidin, CEPC, ceralure, cerenox, Cevadilla, Cheshunt mixture, chinalphos, quinalphos-methyl, chinomethionat, chinomethionate, chiralaxyl, chitosan, chlobenthiazone, chlomethoxyfen, chloralose, chloramben, chloramine phosphorus, chlor Ramphenicol (chloramphenicol), chloraniformethan (chloraniformethan), chloranil, chloranocryl (chloranocryl), chlorantraniliprole (chlorantraniliprole), chlorazifop (chlorazifop), chlorazine (chlorazine), chlorbeneside, chlorbenzuron (chlorbenzuron), chlorbicyclen (chlorbicyclen), chlorbromuron (chlorbromuron), chlorbufam (chlorbufam), chlordane (chlordane), chlordecone (chlordecone), chlordimeform (chlordimeform), chlorenpentrin (chlorempenthrin), chloretazate (chloretazate), chlorethephon (chlorethephon), chlorethoxyfos (chlorethoxyfos), chloreturon (chloreturon), Chlorfenac, chlorfenapyr, chlorfenazole, chlorfenethol, chlorfenidim, chlorfenprop, chlorfenson, chlorphen Sulfide (chlorfensulphide), chlorfenvinphos, chlor Fenvinphos-methyl, chlorfluazuron, chlorflurazole (chlorflurazole), chlorflurecol, chlorfluren, chlorflurenol, chloridazon, chlorimuron, chlorinate, chlor-IPC, chlormephos, Lormequat, chlormesulone, chlormethoxynil, chlornidine, chlornitrofen, chloroacetic acid, chlorobenzilate, chlorodinitronaphthalenes, chlorophenizon, chloroform, chloromebuform, chloromethicone, Thiuron (chloromethiuron), chloroneb (chloroneb), chlorophacinone (chloroph acinone), chlorophos, chloropicrin, chloropon, chloropropylate, chlorothalonil, chlorotoluron, chloroxy Phenizim (chloroxifenidim), chloroxuron, chloroxynil, chlorphonium, chlorphoxim, chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos, chlorpyrifos-methyl, chlorquinox, chlorsulfuron, chlorthal, chlorthiamid, chlorthiophos, chlortoluron, chlorzoli chlorzolinate, chltosan, cholecalciferol, choline chloride, chromafenozide, cycloheximide, cicloheximide Cimectacarb, cimetacarb, cinerine I, cinerine II, cinerines, cinidon-ethyl, cinmethylin, cinosulfuron, cintofen, ciobutide, cisanilide, cismethrin, clacyfos, clefoxydim, clenpirin, clenpyrin, clethodim, climbazole, cliodinate, clodinafop, cloethocarb, Clofencet, clofenotan, clofentezine, clofenvinphos, clofibric acid, clofop, clomazone, clomeprop, clonitralid, cloprop, cloproxydim, clopyralid, cloquintocet, cloransulam, closantel, clothianidin, clotrimazole, cloxid Cloxyfonac, cloxylacon, clozylacon, CMA, CMMP, CMP, CMU, codlelure, cholecalciferol, colophonate, copper 8-quinolinolate ), copper acetate, copper arsenite acetate, copper arsenate, copper carbonate (basic), copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper silicate, copper sulfate, copper sulfate (basic), copper zinc chromate, coumachlor, coumafene, coumafos, coumafuryl (coumafuryl), coumaphos, coumatetralyl, coumethoxystrobin, coumithoate, coumoxystrobin, CPMC, CPMF, CPPC, credazine, cresol, cresylic acid, crimidine, crotamiton, crotoxyfos ), crotoxyphos, crufomate, cryolite, cue-lure, cufraneb, cumyleron, cumyluron, cuprobam, cuprous oxide, curcumenol, CVMP, cyanamide, cyanatrin, cyanazine, cyanofenphos, cyanogen, cyanophos, cyanthoate, cyan Cyanantraniliprole, cyanuric acid, cyazofamid, sibutryne, cyclafuramid, cyclanilide, cyclaniliprole, cyclethrin, cycloate, cycloheximide, cycloprate, cycloprothrin, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyclo Enopyrafen, cyflufenamid, cyflumetofen, cyfluthrin, cyhalofop, cyha Cyhalothrin, cyhexatin, cymiazole, Cymoxanil, cyometrinil, cypendazole, cypermethrin, cyperquat, cyphenothrin, cyprazine, cyprazole, cyproco cyproconazole, cyprodinil, cyprofuram ), cypromid, cyprosulfamide, cyromazine, cythioate, cytrex, dymron, dara Pon, daminozide, dayoutong, dazomet, DBCP, d-camphor, DCB, DCIP, DCPA, DCPTA, DCU, DDD, DDPP, DDT, DDVP, Debacarb, decafentin, and decamethrin , decarbofuran, DEET, dehydroacetic acid, diquat , delachlor, delnav, deltamethrin , demephion, demephion-O, demephion-S, demeton, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methylsulphone, demeton-S-methylsulphon, DEP, depallethrine, derris, desmedipham, desmetryn, desmetryne, d-fanshiluquebingjuzhi, diafenthiuron , dialifol, dialifos, diallate, diamidafos, dianat, diatomaceous earth, diatomite, diazinon, dibrom, dibutyl phthalate, dibutyl succinate, dicamba ), dicapton (dicapthon), dichlobenil (dichlobenil), diclofenthion (dichlofenthion), dichlofluanid (dichlofluanid), diclone (dichlone), diclo Dichloralurea, dichlorbenzuron, dichlorfenidim, dichlorflurecol, dichlorflu Lenol (dichlorflurenol), dichlormate (dichlormate), dichlormid (dichlormid), dichloromethane, dichloromezotiaz (dicloromezotiaz), dichlorophen (dichlorophen), dichlorprop (dichlorprop), dichlorprop-P, dichlorvos, dichlozolin (dichlozolin), dichlozolin (dichlozoline), diclobutrazol (diclobutrazol), diclocymet (diclocymet), diclofop (diclofop), diclomezine (diclomezine), dicloran (dicloran), diclosulam (diclosulam), dicofol (dicofol), dicophane, dicoumarol, dicresyl, dicrotophos, dicryl, dicoumarol, dicycla Dicyclanil, dicyclonon, dieldrin, dienochlor, diethamquat, diethathyl, diethion, diethion, diethofencarb ), dietholate, diethon, diethyl pyrocarbonate, diethyl Toluamide, difenacoum, difenoconazole, difenopenten, difenoxuron, difenzocor difenzoquat, difethialone, diflovidazin ), diflubenzuron, diflufenican, diflu Diflufenicanil, diflufenzopyr, diflumet Diflumetorim, dikegulac, dilor, dimatif, dimefluthrin, dimefox, dimefuron, dimehypo, dimepiperate, dimethachlone, dimethane, dimethacarb, dimethachlone, dimethachlor, dimethametryn, di Methenamid, dimethenamid-P, dimethipin, dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl carbate, dimethyl disulfide Fido, dimethyl phthalate, dimethylvinphos, dimetilan, dimexano, dimidazon, dimoxystrobin, dimpylate, dimuron, dinex, dingjunezuo, diniconazole, diniconazole Lu-M, dinitramine, dinitrophenols, dino Dinobuton, dinocap, dinocap-4, dinocap-6, dinocton, dinophenate, dinopenton, dinoprop, dinosam, dinoseb, dinosulfon, dinotefuran, dinoterb, dinoterbone, diofenolan nolan), dioxabenzofos, dioxacarb, dioxathion, dioxation, diphacin, diphacinone, diphenadione, diphenamid, diphenamide, diphenyl sulfone, diphenylamine, diphenyl sulfide, diprogulic acid , dipropalin, dipropetryn, dipterex, dipymetitrone, dipyrithione, diquat, disodium tetraborate, disosultap, disparlure, disugran, disul, disulfiram, disulfoto disulfoton, ditalimfos, dithianon, dithichloro Dithicrofos, dithioether, dithiometon , dithiopyr, diuron, dixanthogen, d-limonene, DMDS, DMPA, DNOC, dodemorph, dodicin, dodine, dofenapine, doguadine, dominicalure, doramectin, DPC, drazoxolone, DSMA, d-trans-allethrin, d-trans-resmethrin, dufulin, dymron, EBEP, EBP, ebufos, ecdysterone, echlomezol, EDB, EDC, EDDP, edifenphos, eglinazine, emamectin, EMPC, empenthrin ), enadenine, endosulfan, endothal, endo Endothall, endothion, endrin, enestroburin, enilconazole, enoxastrobin, ephirsulfonate, EPN, epocholeone, epofenonane, epoxiconazole, eprinomectin, epronaz naz), EPTC, erbon, ergocalciferol, erlujixiancaoan, esdepallethrine, esfenvalerate, ESP, esprocarb, etacelasil, etaconazole, etaphos, etem, ethaboxam, ethachlor, etha Ethifluralin, ethametsulfuron, ethaprochlor, ethephon, ethidimuron, ethifluralin ... Fencarb, ethiolate, ethion, ethiozin, ethiprole, ethirimol, ethoate-methyl, etobenzanid, ethofumesate, ethohexadiol, ethoprop, ethoprophos, ethoxyfen, ethoxyquin, ethoxysulfuron, ethychlozate, ethyl formate, ethyl pyrophosphate, ethylan, ethyl-DDD, ethylene, ethylene dibromide, ethylene Ethylene dichloride, ethylene oxide, ethylicin, ethylmercury 2,3-dichloride Hydroxypropyl mercaptide, ethylmercury acetate, ethylmercury bromide, ethylmercury chloride, ethylmercury phosphate, etinofen, ETM, etonipromy etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimphos (etrimfos), etrimphos, eugenol, EXD, famoxadone, famphur, fenac, fenamidone , fenaminosulf, phenaminestrobin, fenamiphos, fenapanil, fenarimol, fenasulam, fenazaflor, fenazaquin ), fenbuconazole, fenbutatin oxide, fenchlorazole, fenchlorphos, fenclofos, fenclorim, fenthacarb, fenfluthrin, fenfuram, fenhexamid, phenidin, fenitropan, fenitrothion, Thione, Fenizon, Fenjuntong, Fenobucarb (fenobucarb), fenolovo, fenoprop, fenothione Fenothiocarb, fenoxacrim, fenoxanil, fenoxaprop, fenoxaprop-P, fenoxasulfo fenoxasulfone, fenoxycarb, fenpiclonil, fenpirithrin, fenpropathrin, Fenpropidin, fenpropimorph, fenpyrazamine, fenpyroximate, fenquinotrione, fenridazon, fenson, fensulfothion, fenteracol, fentiapro Fenthiaprop, fenthion, fenthion-ethyl, fentiaprop, fentin, fentrazamide, fentrifanil, fenuron, fenuron-TCA, fenvalerate, ferbam, ferimzone, ferric phosphate, ferrous sulfate, fipronil, flamprop, flamprop-M, flazasulfuron, flocumafen, flometoquin, flonicamid, florasulam, fluacrypyrim, fluazifop, fluazifop-P, fluazinam, fluazolate, fluazuron, flubendiamide, flubenzimine, flubrocythrinate, flucarbazone, flucetosulfuron , fluchloralin, flucofuron, flucycloxuron, flucythrinate, fludioxonil, fluenethyl, fluenetil, fluensulfone, flufenacet, flufenerim, flufenican, flufenoxuron, flufenoxystrobin, flufenprox, flufenpyr, flufenzine, flufiprole, Fluhexafon, flumethrin, flumetober, flumetralin, flumetsulam, flumezin, flumiclorac, flumioxazin, flumipropyn, flumorph, fluometuron, fluopicolide, fluopyram, fluorbenside, fluoridamide, fluoroacetamide, fluoroacetic acid, fluorochloridone, fluorodifen, flu Oroglycofen, fluoroimide, fluoromide, fluoromidine, fluoronitrofen, fluroxypyr, fluothiuron, fluotrimazole, fluoxastrobin, flupoxam, flupropacil, flupropadine, flupropanate, flupyradifurone, flupyrsulfuron, fluquinconazole, fluralaner, fluralaner, Flurazole, flurecol, flurenol, flu Fluridone, flurochloridone, fluromidine, fluroxypyr, flurprimidol, flurus Flursulamid, flurtamone, flusilazole, flusulfamide, flutenzine, fluthiacet, fluthiamide, flutianil, flutolanil, flutriafol, fluvalinate , fluxapyroxad, fluxofenim, folpel, folpet, fomesafen, fonofos, foramsulfuron, forchlorfenuron, formaldehyde, formetanate, formothion, formo Paranate, fosamine, fosetyl, fosmethicone fosmethilan, fospirate, fosthiazate, Fostietan, frontalin, fthalide, Fuberidazole, Fukaojing, Fukaomi, Fujunmanzhi, Fulumi, Fumarin, Funaihecaoling, Fuphenthiourea, Furalane, Furalaxyl, Furamethrin, Furametpyr, Furantebufenozide tebufenozide), furathiocarb, furcarbanil, furconazole, fluconazole-cis, furethrin, furfural, furilazole, furmecyclox, furophanate, furyloxyfen, gamma-BHC, gamma-cyhalothrin, gamma-HCH, Genit, gibberellic acid, gibberellin A3, gibberellins, gliftor, glitor, glucochloralose, glufosinate glufosinate, glufosinate-P, gliodin, glyoxime, glyphosate, glyphosine, gossyplure, grandlure, griseofulvin, guanoctine, Azatine, halacrinate, halauxifen, halfenprox, halofenozide, halosafen, halosulfuron, haloxydine , haloxyfop, haloxyfop-P, haloxyfop-R, HCA, HCB, HCH, hemel, hempa, HEOD, heptachlor, heptafluthrin, heptenophos, heptopargil, Herbima Herbimycin, herbimycin A, heterophos, hexachlor, hexachloran, hexachloroacetone, hexachlorobe benzene, hexachlorobutadiene, hexachlorophene, hexaconazole, hexaflumuron, hexafluoramine, Hexaflurate, hexalure, hexamide, Hexazinone, hexylthiofos, hexythiazox, HHDN, holosulf, homobrassinolide, huancaiwo, huanchongjing, Huan Huangcaoling, Huanjunzuo, Hydramethylnon, Hydrargaphen, Slaked lime, Hydrogen cyanamide, Hydrogen cyanide, Hydroprene, Hydroxyisoxazole, Hymexazol, Hyquincarb ), IAA, IBA, IBP, icaridin, imazalil, imazamethabe Imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, imibenconazole, imicyaphos (imicyafos), imidacloprid, imidaclothiz , iminoctadine, imiprothrin, inabenfide (inabenfide), indanofan, indaziflam, in Doxacarb, inezin, infusoria earth, iodobonil ), iodocarb, iodofenphos, iodomethane, iodine Iodosulfuron, iofensulfuron, ioxy Ioxynil, Ipazine, IPC, Ipconazole, Ipfu Ipfencarbazone, iprobenfos, iprodione, iprovalicarb, iprimidam, ipsdienol, ipsenol, IPSP, IPX, isamidofos, isazofos, isobenzan, isocarbamid, isocarbamide, isocarbophos, isocyanamide ... isocil, isodrin, isofenphos, isofenphos s-methyl, isofetamide, isolane, isomethiozin, isonoruron, isopamphos, isopamphos, isoporine isopolinate, isoprocarb, isoprocil, isopropalin, isopropazol, isoprothiolane, isoproturon, isopyrazam, Sopyrimol, isothioate, isotianil, isouron, isovaledione, isoxaben, isoxachlortole, isoxadifen, isoxaflutole, isoxapyrifop, isoxathion, isuron, ivermectin, ixoxaben, isopamfos, isopamphos, japonilure, japothrins, jasmolin I, jasmolin II, jasmonic acid, jiahuangchongzong, diazizenguxia Olin (jiajizengxiaolin), Jiaxiangjunzhi (jiaxiangjunzhi), Jiecaowan (jiecaowan), Jiecaoxi (jiecaoxi), Jinganmycin A (jinganmycin A), Iodofenphos, juvenile hormone I, juvenile hormone II, juvenile hormone III, kadethrin, kappa-bifenthrin, kappa-tef Lutrin (kappa-tefluthrin), karbutilate, karetazan, kasugamycin, kejunlin, kelevan, ketospira Ketospiradox, diatomaceous earth, kinetin, kinoprene, chiralaxyl, kresoxim-methyl, quicaoxy (kuicaoxi), lactofen, lambda-cyhalothrin, latilure, lead arsenate, lenacil, lepimectin, leptophos, lianbenjingzhi, lime sulfur, lindane, lineatin, linuron, lirimfos, litir Litlure, Looplure, Lufenuron, Luxiancaolin, Lvdingjunzhi, Lvfumijvzhi, Lvxiancaolin, Lythidathion, M-74, M-81, MAA, Magnesium phosphide, Malathion, Maldison ), maleic hydrazide, malonoben, maltodextrin, MAMA, ma Mancopper, mancozeb, mandestrobin ), mandipropamid, maneb, matrine, ma Didox, MCC, MCP, MCPA, MCPA-thioethyl, MCPB, MCPP, mebenil, mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop-P, medimeform , medinoterb, medlure, mefenacet, mefenoxam, mefenpyr, mefluidide ), megatomoic acid, melissyl alcohol, melitoxin, MEMC, menasone, MEP, mepanipyrim, meperfluthrin, mephenate, mephosfolan, mepiquat, mepronil, meptyldinocap, mercaptodimethur, mercaptophos, mercaptophos thiol, mercaptothion, mercuric chloride, oxidized Mercuric chloride, mercurous chloride, merphos, merphos oxide, mesoprazine, mesosulfuron, mesotrione, mesulfen, mesulfenphos, mesulfen, metacresol, metaflumizone, metalaxyl, metalaxyl-M, metaldehyde, metam, metamifop, metamitron, metaphos, metaxon, metazachlor, metazosulfuron, metazoxolone (metazoxolon), metconazole (metconazole), metepa (metepa), metofluran (metflurazon), methabenzthiazuron (methabenzthiazuron), methacrifos (methacrifos), methalpropalin (methalpropalin), metham (metham), methamidophos (methamidophos), methasulfocarb (methasulfocarb), methazole (methazole), metofuroxam (methfuroxam), methybenzuron (methibenzuron), methidathion (methidathion), methiobencarb (methiobencarb), methiocarb (methiocarb), methio Pyrisulfuron, methiotepa, methiozolin, methiuron, methocrotophos, metolcarb, methometon, methomyl, methoprene, metoprothrin, methoprotryne, methoquin-butyl, methothrin, methoxychlor, methoxyphen Methoxyfenozide, methoxyphenone, methyl afolate (methyl apholate), methyl bromide, methyl eugenol, methyl iodide, methyl isothiocyanate ocyanate, methyl parathion, methylacetophos, methylchloride methyldithiocarbamic acid, methyldichloroform Methyldymron, methylene chloride, methyl-isofenphos, methylmercaptophos, methylmercaptophos oxide, methylmercaptophos thiol, methylmercury benzoate, methylmercury dicyandiamide, methylmercury pentachlorophenoxide, methylneodecanamide, methyl Methylnitrophos, methyltriazothion, methiozolin, metiram, metiram zinc, metiram-zinc, methiram benzuron (metobenzuron), metobromuron (metobromuron), metofluthrin (metofluthrin), metolachlor (metolachlor), metolcarb (metolcarb), metometuron (metometuron), metominostrobin (metominostrobin), metosulam ), metoxadiazone, metoxuron, metrafenone, metriam, metribuzin, metrifonate, metriphonate, metsulfovax, metsulfuron, mevinphos, mexacarbate, mieshuwei, mieshuan, miewenjuzhi, milbemectin, milbemycin oxime oxime), milneb, mima2nan, mipafox, MIPC, mirex, MNAF, moguchun, molinate, molosultap, momfluorothrin, Monalide, monisouron, monoamitraz , monochloroacetic acid, monocrotophos, monolinuron, monomehypo, monosulfiram, monosulfuron, monosultap, monuron, monuron-TCA, Morfamquat, moroxydine, morphothion, morzid, moxidectin, MPMC, MSMA, MTMC, Muscalure, myclobutanil, myclozolin ), myricyl alcohol, N-(ethylmercury)-p-toluenesulfonanilide, NAA, NAAm, nabam, naphthalofos, naled, naphthalene, naphthaleneacetamide, naphthalic anhydride, naphthalophos, naphthoxyacetic acid , naphthylacetic acid, naphthylindan-1,3-diones, naphthyloxyacetic acid, naphthylaniline naproanilide, napropamide, napropamide-M, naptalam, natamycin, NBPOS, neburea, neburon, nendrin, neonicotine, nichlorfos, niclofen, niclosamide, nicobifen, nicosulfuron n), nicotine, nicotine sulfate, nifluridide, nikkomycins, NIP, nipyraclofen, nipyralofen, nitenpyram, nithiazine, nitralin, nitrapyrin, nitrilacarb, nitrofen, nitrofluorfen, Trostyrene, nitrothal-isopropyl, nobormide, nonanol, norbormide, norea, norflurazon, nornicotine, noruron, novaluron, noviflumuron, NPA, nuarimol, nurano Nuranone, OCH, octachlorodipropyl ether, octhilinone, o-dichlorobenzene, ofurace, omethoate, o-phenylphenol, orbencarb, orfralure, orthobencarb, ortho-dichlorobenzene, orthosulfamuron, orictalure, orysastrobin, oryzalin, osthol, osthole, ostramone, ovatron, ovex, oxabetrinil, oxadiargyl, oxadiazon, oxadixyl (oxadixyl), oxamate, oxamyl, oxapyrazon, oxapyrazone, oxasulfuron, ox Oxathiapiprolin, oxaziclomefone, oxine-copper, oxine-Cu, oxolinic acid, oxpoconazole, oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton, oxyenadenine, oxyfluorfen, oxymatrine, oxytetracycline, oxythioquinox, PAC, paclobutrazol, paichongding, pallethrine, PAP, para-dichlorobenzene, parafluron, paraquat, parathion, parathion-methyl, parinol, Paris green, PCNB, PCP, PCP-Na, p-dichlorobenzene, PDJ, peb pebulate, pedinex, pefurazoate, pelargonic acid, penconazole, pencycuron, pendimethicone Pendimethalin, penfenate, penflufen ), penfluron, penoxalin, penoxsulam, pentachlorophenol, pentachlorophenyl laurate, pentanochlor, penthiopyrad, pentomethrin, Pentoxazone, perchlordecone, perfluid perfluidone, permethrin, pethoxamid, PHC, phenamacril, fenamacryl-ethyl, phenaminosulf, phenazine oxide, fenetacarb, Phenisopham, phenkapton, phenmedipham Phenmedipham, phenmedipham-ethyl, fenobenzuron, phenothiol, fenothrin, phenproxide, phenthoate, phenylmercuriurea, phenylmercuric acetate, phenylmercuric chloride, phenylmercuric derivatives of pyrocatechol, phenylmercuric nitrate, phenylmercuric salicylate, phorate, phosacetim , phosalone, phosametine, phosazetim, phosazetin, phoscyclotin, phosdiphen, fosetyl, phosfolan, phospholan-methyl, phosglyc Phosglycin, phosmet, phosnichlor, phosphamide, phosphamidon, phosphine, phosphinotri Phosphinothricin, phosphocarb, phosphorus, phostin, phoxim, phoxim-methyl, phthalide, phthalophos, phthalthrin, picarbutrazox, picarbutrazox, picarbutrazox, picarbutrazox, picarbutrazox, picarbutrazox, picarbutrazox, picarbutrazox, picarbutrazox, picarbutrazox, picarbutrazox, phthal ... Picaridin, picloram, picolinafen, picoxystrobin, pimaricin, pindone, pinoxaden, piperaline, piperazine, piperonyl butoxide, piperonyl cyclonene, piperophos, piproctanly, piproctanyl, piprotal, pyrimethane Pirimetaphos, pirimicarb, piriminil, piri Pirimioxyphos, pirimiphos-ethyl, pirimiphos-methyl, pival, pivaldione, plifenate, PMA, PMP, polyb Tenths, polycarbamates, polychlorcamphene, polyethoxy Polyethoxyquinoline, polyoxin D, polyoxins, polyoxol Polyoxorim, polythialan, potassium arsenite, potassium azide, Potassium cyanate, potassium ethylxanthate, potassium naphthenate, potassium polysulfide, potassium thiocyanate, pp'-DDT, prallethrin, precocene I, precocene II, precocene III, pretilachlor , primidophos, primisulfuron, probenazole, prochloraz, proclonol, procyazine, procymidone, prodiamine, Profenofos, profluazol, profluralin, profluthrin, profoxydim, profurite-aminium, proglinadin, prohexadione, prohydrojasmon, promacyl, promecarb, prometon, prometryn, prometryne, promurit, pronamide, propachlor, propafos, propamidine, propamocarb, propanil, propaphos, propaquizafop, propargite, propa Lutrin (proparthrin), propazine (propazine), propetamphos (propetamphos), propham (propham), propiconazole (propiconazole), propidine (propidine), propineb (propineb), propisochlor (propisochlor), propoxur (propoxur), propoxycarbazone (propoxycarbazone), propyl isome (propyl isome) ), propyrisulfuron, propyzamide, proquinazid, prosuler, prosulfalin, prosulfocarb, prosulfuron, prothidathion prothidathion, prothiocarb, prothioconazole, prothifos, prothoate, protrifenb Protrifenbute, Proxan, Prymidophos, Prinac prynachlor, psoralen, psoralene, pydanon, pyflubumide, pymetrozine, pyracarbolid, pyraclofos, pyraclonil, pyraclostrobin, pyraflufen, pyrafluprole, pyramat, pyrametostrobin, pyraoxystrobin, pyrasulfotole, pyrazid Flumid (pyraziflumid), pyrazolate (pyrazolate), pyrazolinate (pyrazolynate), pyrazon (pyrazon), pyrazophos (pyrazophos), pyrazosulfuron (pyrazosulfuron), pyrazothion (pyrazothion), pyrazoxyfen (pyrazoxyfen), pyrethme pyrethrin, pyrethrin I, pyrethrin II, pyrethrins, pyribambenz-isopropyl, pyribambenz-propyl, pyribencarb, pyribenzoxim, pyributicarb , pyriclor, pyridaben, pyridafol, pyridalyl, pyridaphenthion, pyridaphenthione, pyridate, pyridinitril, pyrifenox, pyrifluquinazon, pyriftalid, pyrimetaphos aphos), pyrimethanil, pirimicarb, pyrimidifen, pyriminobac, pyriminostrobin, pirimiphos-ethyl, pirimiphos-methyl, pyrimisulfan, pyrimitate, pyrinuron, pyriophenone, pyriprole, pyripropano pyripropanol, pyriproxyfen, pyrisoxazole, pyrithiobac, pyrrolan, pyroquilon, pyroxasulfone, pyroxsulam, pyroxsulam, pyrithiobac, pyrithiobac, pyrithiobac, pyrithiobac, pyrithiobac pyroxychlor, pyroxyfur, qincaosuan, qingkuling, quassia, quinacetol, quinalphos, quinalphos-methyl, quinazamid, quinclorac, quinconazole, quinmerac, quinoclamine, quinomethionate, quinonami quinonamid, quinothion, quinoxyfen, quintiofos, quintozene, quizalofop, quizalofop-P, quwenzhi, quyingding, rabenzazole, rafoxanide, R-diniconazole, rebemide, reglone, renriduron, rescalure ), resmethrin, rhodetanil, rhodojaponin-III, ribavirin, rimsulfuron, rizazo R-metalaxyl, rizazole, rodetanil, ronnel (ronnel), rotenone, ryania, sabadilla, sa Flufenacil, Saijunmao, Saisentong, salicylanilide, salifluofen, sanguinarine, santonin, S-bioallethrin, Schradan, scilliroside, sebuthylazine, sec Secbumeton, sedaxane, selamectin, semiamitraz, sesamex, sesamolin, Sesone, sethoxydim, sevin, shuangjian Kaolin (shuangjiaancaolin), Shuangjianankaolin (shuangjianancaolin) , S-hydroprene, siduron, sifumijvzhi, siglure, silafluofen, silatrane ), silica aerogel, silica gel, silthiofam, silthiopham, silthiophan, silvex, simazine ( simazine), simeconazole, simeton, simetryn, simetryne, sintophen, S-kinoprene, hydrated lime, SMA, S-methoprene, S-metolachlor, sodium arsenite sodium, sodium azide, sodium chlorate, sodium cyanide, sodium fluoride, sodium fluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodium o-phenylphenoxide, sodium orthophenylphenoxide, sodium pentachlorophenate, sodium pentachlorophenoxide, sodium polysulfide, sodium silicofluoride, sodium tetrathiocarbonate, sodium thiocyanate, solan, sophamide, spinetoram, spinosad, spirodiclofen, spiromesifen, Spirotetramat, spiroxamine, stirofos, streptomycin, strychnine, sulcatol, sulcofuron, sulcotrione, sulfalate , sulfentrazone, sulfiram, sulfluramide sulfuramid, sulfodiazole, sulfometuron ), sulfosate, sulfosulfuron, sulfotep, sulfotepp, sulfoxaflor, sulfoxide, sulfoxime, sulfur, sulfuric acid, sulfuryl fluoride, sulglycapin, sulfosate, sulprofos, sultropen, swep, tau-fluvalinate, tavron, tazimcarb, TBTO, TBZ, TCA, TCBA, TCMTB , TCNB, TDE, tebuconazole, tebufenozide, te bufenpyrad, tebufloquin, tebupirimfos, tebutam, tebuthiuron, tecloftalam, tecnazene, tecoram, tedion, teflubenzuron, tefluthrin, and tefurtrio tefuryltrione, tembotrione, temefos, temefos Temephos, Tepa, TEPP, Tepraloxydim, Teproloxydim, Terallethrin, Terbacil, Terbucarb, Terbuchlor, Terbufos, Te Lubumeton (terbumeton), terbuthylazine (terbuthylazine), terbutol (terbutol), terbutryn (terbutryne), teraclor (terraclor), terramycin (terramicin), terramycin (terramycin), tetcyclacis (tetcyclacis), tetrachloroethane, tetrachlorvinphos, tetraconazole (tetraconazole), tetradifon (tetradifon), tetradisul (tetradisul), tetrafluron (tetrafluron), tetramethrin (tetramethrin), tetramethylfluthrin (tetramethylfluthrin), tetramine (tetramine), tetranactin (tetranactin), tetraniliprole (tetraniliprole), tetrapion (tetrapion), tetrasul (tetrasul ), thallium sulfate, thallous sulfate, thenylchlor, theta-cypermethrin, thiabendazole, thiacloprid, thiadiazine, thiadifluor, thiamethoxam, thiameturon, thiapronil, thiazafluron, thiazfluron ), thiazone, thiazopyr, cyclophos, thicyofen, thidiazimin, thidiazuron , thiencarbazone, thifensulfuron, thifluzamide, thimerosal, thimet, thiobencarb, thiocarboxime, thiochlorfenphim, thiochlorphenphime, thiocyanatodinitrobenzenes, thiocyclam, thiodan, thiodiazole-copper, thio Thiodicarb, thiofanocarb, thiofanox, thiofluoximate, thiohempa, thiomersal, thiometon, thionazin, thiophanate, thiophanate-ethyl, thiophanate-methyl, thiophos (thiophos), thioquinox, thiosemicarbazide, thiosultap, thiotepa, thioxamyl, thiram, thiuram, thuringiensin, thiabendazole, tiadinil, tiafenacil, tiaojiean ), TIBA, tifatol, thiocarbazil, thioclorim, tioxazafen, tioximid, tirpar tirpate, TMTD, tolclofos-methyl, tolfenpyrad, tolprocarb, tolpyralate, tolyfluanid, tolylfluanid, tolylmercury acetate To, tomarin, topramezone, toxaphene , TPN, tralkoxydim, tralocythrin, tralomethrin, tralopyril, transfluthrin, transpermethrin, tretamine, tri Acontanol, triadimefon, triadimenol (triadimenol), triafamone, triallate, tri- Tri-allate, triamiphos, triapenthenol, triarathene, triarimol, triasulf triasulfuron, triazamate, triazbutil, triaziflam, triazophos, triazothion, triazoxide, tribasic copper chloride, tribasic copper sulfate, tribenuro tribenuron, tribufos, tributyltin oxide, tricamba, trichlamide, triclopyr, trichlorfo trichlorfon, trichlormetaphos-3, trichloronate (trichloronat), trichloronate, trichlorotrinitrobenzene Trichlorphon, triclopyr, and triclopyrica Triclopyricarb, tricresol, tricyclazole, tricyclohexyltin hydroxide, tridemorph, tridiphane, trietazine, trifenmorph, tripenofos, trifloxystrobin, trifloxy Sulfuron (trifloxysulfuron), trifludimoxazin, triflu Triflumezopyrim, triflumizole, triflumuro triflumuron, trifluralin, triflusulfuron, trifop, trifopsime, triforine ), trihydroxytriazine, trimedlure, trimethacarb, trimeturon, trinexapac, triphenyltin, triprene, tripropindan, triptolide, tritac, trithialan, triticonazole, tritosulfuron, trunc-call, tuoyelin, uniconazole, uniconazole-P, urbacide, uredepa, valerate, validamay Syn, validamycin A, valifenalate, valone, vami Vamidothion, Vanguard, Vaniliprole, Vernolate, vinclozolin, vitamin D3, warfarin, xiaochongliulin, xinjunan, xiwojunan, xiwojunzhi, XMC, xin Xylachlor, xylenols, xylylcarb, xymiazo xymiazole, yishijing, zalilamid, zeatin, zengxiaoan, zengxiaolin, zeta-cypermethrin, zinc naphthenate, zinc phosphide, zinc thiazole, zinc thiozole, zinc trichlorophenate, zinc trichlorophenoxide, zineb, ziram, zolaprofos, zoocoumarin, zoxamide, zuoanjunzhi, zuocaoan, zuo Junchi (zuojunzhi), Zuomihuanglong (zuomihuanglong), α-chlorohydrin, α-ecdysone, α-multistriatin, α-naphthaleneacetic acid, and β-ecdysone; (2) The molecule shown below (a) N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide (hereinafter referred to as "AI-1") 【Chemical 1】 (b) (3S,6S,7R,8R)-8-benzyl-3-(3-((isobutyryloxy)methoxy)-4-methoxypicolinamido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate (hereinafter referred to as "AI-2") 【Chemistry 2】 (3) A molecule known as Lotilaner, which has the following structure: 【Chemistry 3】 (4) The following molecules listed in Table A: Table A - Structure of M# - Active Ingredients 【Table 1-1】 【Table 1-2】 AI-1 is N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)thio)propanamide; AI-2 is (3S,6S,7R,8R)-8-benzyl-3-(3-(isobutyryloxy)methox-1-yl)isobutyrate. (iii)-4-Methoxypicolinamido)-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl the law of nature, AIGA-2 is 1,3-dichloropropene, chlorpyrifos, hexaflumuron, methoxyfenozide, noviflumuron, spinetoram, spinosad, and sulfoxaflor; The molecules listed in Table A are as follows: Table A 【change】 【change】 composition.

2. The table below and a carrier and / or an active ingredient, Acetylcholinesterase (AChE) inhibitors, GABA-gated chloride channel antagonists, sodium channel modulators, nicotinic acetylcholine receptor (nAChR) agonists, nicotinic acetylcholine receptor (nACh) allosteric activators, chloride channel activators, juvenile hormone mimetics, multispecies nonspecific (multisite) inhibitors, chordotonal organ modulators, mite growth inhibitors, microbial disruptors of insect midgut membranes, mitochondrial ATP synthase inhibitors, uncouplers of oxidative phosphorylation via proton gradient disruption, nicotinic acid and further comprising an active ingredient from group UN, a tin acetylcholine receptor (nACh) channel blocker, a chitin biosynthesis inhibitor type 0, a chitin biosynthesis inhibitor type 1, a Diptera molting disruptor, an ecdysone receptor agonist; an octopamine receptor agonist, a mitochondrial complex III electron transport inhibitor, a mitochondrial complex I electron transport inhibitor, a voltage-dependent sodium channel blocker, an acetyl CoA carboxylase inhibitor, a mitochondrial complex IV electron transport inhibitor, a mitochondrial complex II electron transport inhibitor, a ryanodine receptor modulator, or an active ingredient from group UN, wherein the group UN is azadirachtin, benzoximate, bifenazate, bromopropylate, chinomethionate, cryolite, dicofol, pyridalyl, and pyrifluquinazone; composition.

3. 10. A process for controlling pests comprising applying to an area a pesticidally effective amount of the composition of claim 1 or 2.

4. 4. The process of claim 3, wherein the pest is selected from the group consisting of ants, aphids, bedbugs, beetles, silverfish, caterpillars, cockroaches, crickets, earwigs, fleas, flies, grasshoppers, grubs, leafhoppers, lice, locusts, maggots, mites, nematodes, planthoppers, psyllids, sawflies, scale insects, silverfish, slugs, snails, spiders, springtails, stink bugs, symphytes, termites, thrips, mites, digger wasps, whiteflies, and wireworms.

5. The pest is a sap-feeding or chewing pest, or the pest is selected from the group consisting of aphids, leafhoppers, moths, scale insects, thrips, psyllids, mealybugs, stink bugs, and whiteflies, or the group consisting of caterpillars, beetles, grasshoppers, and locusts, or the pest is selected from the group consisting of Phthiraptera and Hemiptera, or the group consisting of Coleoptera and Lepidoptera, or the pest is selected from the group consisting of Auracasspis spp., Afroaphids, 4. The process of claim 3, wherein the genus is selected from the group consisting of Phora spp., Aphis spp., Bemisia spp., Cox spp., Eusistus spp., Rhygus spp., Macrosihum spp., Nezara spp., and Rhopalosihum spp., or the group consisting of Antonomus spp., Cerotomus spp., Chaetocnema spp., Collaspis spp., Cyclocephala spp., Diablotica spp., Hypera spp., Phyllophaga spp., Phylotreta spp., Sphenophorus spp., and Sitophilus spp.

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